NP-MRD: Showing NP-Card for (rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+ (NP0025654)

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Record Information

Version

1.0

Created at

2021-06-19 17:43:31 UTC

Updated at

2021-06-29 23:50:44 UTC

NP-MRD ID

NP0025654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+

Provided By

JEOL Database JEOL Logo

Description

(rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+ is found in Vitex rotundifolia. It was first documented in 2001 (Ono, M., et al.). Based on a literature review very few articles have been published on (5S,6R,8R,9R,10S,13R,16S)-6-Acetoxy-9,13-epoxy-16-hydroxy-16-methoxylabdane-15-oic acid 15,16-lactone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119433D          

 65 68  0  0  0  0            999 V2000
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    0.1368    0.5973   -3.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271    0.6309   -2.8423 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2453    1.6189   -3.4631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182    2.8009   -2.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638    3.8746   -3.1924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1770    2.5920   -1.5965 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3298    1.0965   -1.3825 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5764    0.7603   -0.5691 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0417    0.6280    0.8402 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.4493   -1.4013    0.7750 C   0  0  2  0  0  0  0  0  0  0  0  0
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 28 11  1  0  0  0  0
  3  4  1  0  0  0  0
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M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    0.1807    0.0303   -4.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192119433D          

 65 68  0  0  0  0            999 V2000
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    0.1368    0.5973   -3.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271    0.6309   -2.8423 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2453    1.6189   -3.4631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182    2.8009   -2.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5802    0.1633    0.6767 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.4493   -1.4013    0.7750 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3570   -2.2001   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9977   -1.8587    0.5181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0130   -1.2127    1.4632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7905   -1.6840    2.8031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456   -2.8830    3.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -3.2164    4.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0073   -3.5933    2.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067    0.3324    1.4061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1074    1.0985    2.0981 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3349    0.7824    3.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4390    0.7333    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256    2.6253    1.9147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5450    3.1284    2.2998 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4620    2.4102    1.5004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4380    0.8643    1.7064 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0701    0.6005    3.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5404   -1.0023   -4.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9003   -0.3545   -2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0182   -0.1852   -0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6419   -0.0492    1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7330   -1.7141    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4129   -2.0537    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1877   -1.9366   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1669   -3.2751   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2789   -1.6357   -0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0475   -2.9493    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0117   -1.5164    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4334   -2.4502    5.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -4.1788    4.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396   -3.2935    4.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571    0.5671    0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4890    1.0371    4.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5801   -0.2704    3.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870    1.3556    3.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2592    1.3739    1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7403   -0.3006    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3595    0.8624    0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1018    2.8891    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812    3.1739    2.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3802    3.0248    3.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4879    4.2029    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004    2.8592    1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    2.6403    0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744    1.0151    3.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423    1.0724    3.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397   -0.4578    3.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 11  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  0  0  0  0
 21 16  1  0  0  0  0
 28 29  1  1  0  0  0
 16 15  1  0  0  0  0
 16 17  1  0  0  0  0
 15 13  1  0  0  0  0
  8  3  1  0  0  0  0
 11 13  1  0  0  0  0
 22 23  1  1  0  0  0
 22 21  1  0  0  0  0
 22 24  1  0  0  0  0
 28 27  1  0  0  0  0
 21 50  1  6  0  0  0
 28 21  1  0  0  0  0
 13 14  1  0  0  0  0
 11 12  1  6  0  0  0
 11 10  1  0  0  0  0
 17 18  1  0  0  0  0
  8  9  1  0  0  0  0
 18 19  1  0  0  0  0
  9 10  1  0  0  0  0
 18 20  2  0  0  0  0
  8 12  1  1  0  0  0
 26 25  1  0  0  0  0
  5  6  2  0  0  0  0
 26 27  1  0  0  0  0
  3  2  1  0  0  0  0
 25 22  1  0  0  0  0
  2  1  1  0  0  0  0
 26 59  1  0  0  0  0
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 27 61  1  0  0  0  0
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  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  0  0  0  0
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  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
 29 63  1  0  0  0  0
 29 64  1  0  0  0  0
 29 65  1  0  0  0  0
  3 33  1  1  0  0  0
 23 51  1  0  0  0  0
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 23 53  1  0  0  0  0
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  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])O[C@@]1([H])OC(=O)C([H])([H])[C@@]11O[C@]2(C([H])([H])C1([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]21C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H36O6/c1-14-12-16(27-15(2)24)18-20(3,4)8-7-9-21(18,5)23(14)11-10-22(29-23)13-17(25)28-19(22)26-6/h14,16,18-19H,7-13H2,1-6H3/t14-,16-,18+,19+,21+,22-,23-/m1/s1

> <INCHI_KEY>
SFOHMBBFSBTGGN-TUBJXHARSA-N

> <FORMULA>
C23H36O6

> <MOLECULAR_WEIGHT>
408.535

> <EXACT_MASS>
408.251188879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
44.487769265623605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,2''S,4R,4aS,5'R,8aS)-2''-methoxy-2,5,5,8a-tetramethyl-5''-oxo-octahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
3.7449935059999984

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.983388650485861

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
105.4397

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,2''S,4R,4aS,5'R,8aS)-2''-methoxy-2,5,5,8a-tetramethyl-5''-oxo-hexahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    0.1807    0.0303   -4.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1368    0.5973   -3.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271    0.6309   -2.8423 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2453    1.6189   -3.4631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182    2.8009   -2.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638    3.8746   -3.1924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1770    2.5920   -1.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3298    1.0965   -1.3825 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5764    0.7603   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417    0.6280    0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    0.1633    0.6767 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2115    0.5439   -0.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4493   -1.4013    0.7750 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3570   -2.2001   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9977   -1.8587    0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0130   -1.2127    1.4632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7905   -1.6840    2.8031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456   -2.8830    3.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -3.2164    4.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0073   -3.5933    2.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067    0.3324    1.4061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1074    1.0985    2.0981 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3349    0.7824    3.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4390    0.7333    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256    2.6253    1.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5450    3.1284    2.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4620    2.4102    1.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    0.8643    1.7064 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0701    0.6005    3.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5404   -1.0023   -4.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9003   -0.3545   -2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    2.8830   -1.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5620    3.1796   -0.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3698    1.5119   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -0.1852   -0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114    1.6115    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6419   -0.0492    1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7330   -1.7141    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4129   -2.0537    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1877   -1.9366   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1669   -3.2751   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2789   -1.6357   -0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0475   -2.9493    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0117   -1.5164    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4334   -2.4502    5.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -4.1788    4.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396   -3.2935    4.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571    0.5671    0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4890    1.0371    4.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5801   -0.2704    3.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870    1.3556    3.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2592    1.3739    1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7403   -0.3006    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1018    2.8891    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812    3.1739    2.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3802    3.0248    3.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4879    4.2029    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004    2.8592    1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    2.6403    0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744    1.0151    3.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423    1.0724    3.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397   -0.4578    3.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 11  1  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  8  7  1  0
 21 16  1  0
 28 29  1  1
 16 15  1  0
 16 17  1  0
 15 13  1  0
  8  3  1  0
 11 13  1  0
 22 23  1  1
 22 21  1  0
 22 24  1  0
 28 27  1  0
 21 50  1  6
 28 21  1  0
 13 14  1  0
 11 12  1  6
 11 10  1  0
 17 18  1  0
  8  9  1  0
 18 19  1  0
  9 10  1  0
 18 20  2  0
  8 12  1  1
 26 25  1  0
  5  6  2  0
 26 27  1  0
  3  2  1  0
 25 22  1  0
  2  1  1  0
 26 59  1  0
 26 60  1  0
 25 57  1  0
 25 58  1  0
 27 61  1  0
 27 62  1  0
 16 46  1  6
 15 44  1  0
 15 45  1  0
 13 40  1  1
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  9 37  1  0
 10 38  1  0
 10 39  1  0
  7 34  1  0
  7 35  1  0
 29 63  1  0
 29 64  1  0
 29 65  1  0
  3 33  1  1
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
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 14 43  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.181   0.030  -4.758  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.137   0.597  -3.456  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.427   0.631  -2.842  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.245   1.619  -3.463  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.018   2.801  -2.820  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.464   3.875  -3.192  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.177   2.592  -1.597  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.330   1.097  -1.383  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.576   0.760  -0.569  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.042   0.628   0.840  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.580   0.163   0.677  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.212   0.544  -0.673  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.449  -1.401   0.775  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.357  -2.200  -0.171  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.998  -1.859   0.518  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.013  -1.213   1.463  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.791  -1.684   2.803  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.346  -2.883   3.131  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.022  -3.216   4.555  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.007  -3.593   2.389  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.907   0.332   1.406  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.107   1.099   2.098  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.335   0.782   3.588  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.439   0.733   1.384  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.926   2.625   1.915  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.545   3.128   2.300  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.462   2.410   1.500  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.438   0.864   1.706  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.070   0.601   3.148  0.00  0.00           C+0
HETATM   30  H   UNK     0       0.540  -1.002  -4.715  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.834   0.027  -5.165  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.817   0.625  -5.420  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.900  -0.355  -2.919  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.144   2.883  -1.809  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.562   3.180  -0.759  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.370   1.512  -0.640  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.018  -0.185  -0.896  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.111   1.611   1.312  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.642  -0.049   1.457  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.733  -1.714   1.787  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.413  -2.054   0.071  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.188  -1.937  -1.218  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.167  -3.275  -0.070  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.279  -1.636  -0.519  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.048  -2.949   0.626  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.012  -1.516   1.132  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.433  -2.450   5.217  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.473  -4.179   4.813  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.940  -3.293   4.681  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.057   0.567   0.339  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.489   1.037   4.222  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.580  -0.270   3.751  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.187   1.356   3.975  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.259   1.374   1.730  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.740  -0.301   1.580  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.359   0.862   0.299  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.102   2.889   0.863  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.681   3.174   2.491  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.380   3.025   3.376  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.488   4.203   2.087  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.500   2.859   1.766  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.633   2.640   0.444  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.074   1.015   3.291  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.542   1.072   3.913  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.140  -0.458   3.401  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1                                                       
CONECT    3    4    8    2   33                                             
CONECT    4    3    5                                                       
CONECT    5    4    7    6                                                  
CONECT    6    5                                                            
CONECT    7    5    8   34   35                                             
CONECT    8    7    3    9   12                                             
CONECT    9    8   10   36   37                                             
CONECT   10   11    9   38   39                                             
CONECT   11   28   13   12   10                                             
CONECT   12   11    8                                                       
CONECT   13   15   11   14   40                                             
CONECT   14   13   41   42   43                                             
CONECT   15   16   13   44   45                                             
CONECT   16   21   15   17   46                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   47   48   49                                             
CONECT   20   18                                                            
CONECT   21   16   22   50   28                                             
CONECT   22   23   21   24   25                                             
CONECT   23   22   51   52   53                                             
CONECT   24   22   54   55   56                                             
CONECT   25   26   22   57   58                                             
CONECT   26   25   27   59   60                                             
CONECT   27   28   26   61   62                                             
CONECT   28   11   29   27   21                                             
CONECT   29   28   63   64   65                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   21                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   29                                                            
CONECT   64   29                                                            
CONECT   65   29                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  136    0
END

RDKit          3D

65 68  0  0  0  0  0  0  0  0999 V2000
    0.1807    0.0303   -4.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1368    0.5973   -3.4562 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271    0.6309   -2.8423 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2453    1.6189   -3.4631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182    2.8009   -2.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638    3.8746   -3.1924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1770    2.5920   -1.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3298    1.0965   -1.3825 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5764    0.7603   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417    0.6280    0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    0.1633    0.6767 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2115    0.5439   -0.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4493   -1.4013    0.7750 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3570   -2.2001   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9977   -1.8587    0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0130   -1.2127    1.4632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7905   -1.6840    2.8031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456   -2.8830    3.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -3.2164    4.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0073   -3.5933    2.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067    0.3324    1.4061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1074    1.0985    2.0981 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3349    0.7824    3.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4390    0.7333    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256    2.6253    1.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5450    3.1284    2.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4620    2.4102    1.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    0.8643    1.7064 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0701    0.6005    3.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5404   -1.0023   -4.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8342    0.0272   -5.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8172    0.6247   -5.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9003   -0.3545   -2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    2.8830   -1.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5620    3.1796   -0.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3698    1.5119   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -0.1852   -0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114    1.6115    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6419   -0.0492    1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7330   -1.7141    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4129   -2.0537    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1877   -1.9366   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1669   -3.2751   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2789   -1.6357   -0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0475   -2.9493    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0117   -1.5164    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4334   -2.4502    5.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -4.1788    4.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9396   -3.2935    4.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571    0.5671    0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4890    1.0371    4.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5801   -0.2704    3.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870    1.3556    3.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2592    1.3739    1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7403   -0.3006    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3595    0.8624    0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1018    2.8891    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812    3.1739    2.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3802    3.0248    3.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4879    4.2029    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004    2.8592    1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    2.6403    0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744    1.0151    3.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423    1.0724    3.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397   -0.4578    3.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 11  1  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  8  7  1  0
 21 16  1  0
 28 29  1  1
 16 15  1  0
 16 17  1  0
 15 13  1  0
  8  3  1  0
 11 13  1  0
 22 23  1  1
 22 21  1  0
 22 24  1  0
 28 27  1  0
 21 50  1  6
 28 21  1  0
 13 14  1  0
 11 12  1  6
 11 10  1  0
 17 18  1  0
  8  9  1  0
 18 19  1  0
  9 10  1  0
 18 20  2  0
  8 12  1  1
 26 25  1  0
  5  6  2  0
 26 27  1  0
  3  2  1  0
 25 22  1  0
  2  1  1  0
 26 59  1  0
 26 60  1  0
 25 57  1  0
 25 58  1  0
 27 61  1  0
 27 62  1  0
 16 46  1  6
 15 44  1  0
 15 45  1  0
 13 40  1  1
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
  7 34  1  0
  7 35  1  0
 29 63  1  0
 29 64  1  0
 29 65  1  0
  3 33  1  1
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

View in JSmol

Synonyms

Value	Source
(5S,6R,8R,9R,10S,13R,16S)-6-Acetoxy-9,13-epoxy-16-hydroxy-16-methoxylabdane-15-Oate 15,16-lactone	Generator

Chemical Formula

C₂₃H₃₆O₆

Average Mass

408.5350 Da

Monoisotopic Mass

408.25119 Da

IUPAC Name

(1R,2R,2''S,4R,4aS,5'R,8aS)-2''-methoxy-2,5,5,8a-tetramethyl-5''-oxo-octahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate

Traditional Name

(1R,2R,2''S,4R,4aS,5'R,8aS)-2''-methoxy-2,5,5,8a-tetramethyl-5''-oxo-hexahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-4-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])O[C@@]1([H])OC(=O)C([H])([H])[C@@]11O[C@]2(C([H])([H])C1([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]21C([H])([H])[H]

InChI Identifier

InChI=1S/C23H36O6/c1-14-12-16(27-15(2)24)18-20(3,4)8-7-9-21(18,5)23(14)11-10-22(29-23)13-17(25)28-19(22)26-6/h14,16,18-19H,7-13H2,1-6H3/t14-,16-,18+,19+,21+,22-,23-/m1/s1

InChI Key

SFOHMBBFSBTGGN-TUBJXHARSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vitex rotundifolia	JEOL database	Ono, M., et al, Chem. Pharm. Bull. 49, 82 (2001)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.54	ALOGPS
logP	3.74	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.44 m³·mol⁻¹	ChemAxon
Polarizability	44.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8772966

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10597593

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ono, M., et al. (2001). Ono, M., et al, Chem. Pharm. Bull. 49, 82 (2001). Chem. Pharm. Bull..

Showing NP-Card for (rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+ (NP0025654)

MOL for NP0025654 ((rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+)

3D MOL for NP0025654 ((rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+)

3D SDF for NP0025654 ((rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+)

3D-SDF for NP0025654 ((rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+)

PDB for NP0025654 ((rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+)

3D PDB for NP0025654 ((rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+)

SMILES for NP0025654 ((rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+)

INCHI for NP0025654 ((rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+)

Structure for NP0025654 ((rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+)

3D Structure for NP0025654 ((rel 5S,6R,8R,9R,10S,13R,16S)-6-acetoxy-9,13-epoxy-16-metoxy-labden-15,16+)