NP-MRD: Showing NP-Card for (+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+ (NP0036340)

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Record Information

Version

1.0

Created at

2021-06-20 19:32:20 UTC

Updated at

2021-06-30 00:07:56 UTC

NP-MRD ID

NP0036340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+

Provided By

JEOL Database JEOL Logo

Description

(+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+ is found in Croton gratissimus. It was first documented in 2002 (PMID: 33651529). (4S,5E,7S,10R,13R)-4-Isopropyl-4,7-dihydroxy-10-acetoxy-7-methyl-11-methylene-14-oxabicyclo[11.2.1]Hexadecane-1(16),5-diene-15-one is a strongly basic compound (based on its pKa) (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454) (PMID: 26389451) (PMID: 26389436).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121323D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202121323D          

 60 61  0  0  0  0            999 V2000
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   -4.3813    2.6793    3.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    2.4887    4.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2016   -3.8780   -0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0134   -3.9757   -1.6179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -3.5389    0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0582   -1.8715    5.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8916   -1.2735    1.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5124   -1.6616    1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8759   -4.0333    2.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2938   -3.8320    2.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834   -4.4924    1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -5.5477    0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9936   -4.2051   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163   -3.8517   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4424   -1.8568   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1412   -0.4297   -1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1705   -2.5072   -3.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3347   -1.0058   -2.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941   -0.9388   -3.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411   -3.0801   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0466   -1.9941   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9905   -1.4537   -2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -2.6934    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4715   -1.2049    2.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4680    1.5644    2.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864    0.9706    3.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9357    2.1380    2.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0975   -0.1322    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -1.3519    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901   -0.5068    3.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931    0.6673    1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437    1.5558    3.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116    0.2267    4.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065    3.6472    3.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2578    2.0628    3.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2823    2.8477    2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
 21  2  1  0  0  0  0
 11 13  1  0  0  0  0
  2  1  2  3  0  0  0
  9 14  1  0  0  0  0
  2  3  1  0  0  0  0
 15 16  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
 14 15  2  0  0  0  0
  6 26  1  0  0  0  0
 16 19  1  0  0  0  0
  4 28  1  0  0  0  0
 28 26  1  0  0  0  0
 26 27  2  0  0  0  0
  7  6  1  0  0  0  0
 16 18  1  6  0  0  0
  9 11  1  0  0  0  0
 16 17  1  0  0  0  0
  6  5  2  0  0  0  0
  9 10  1  1  0  0  0
  8  9  1  0  0  0  0
 21 22  1  0  0  0  0
 19 20  1  0  0  0  0
 22 23  1  0  0  0  0
 11 12  1  0  0  0  0
 23 25  2  0  0  0  0
 20 21  1  0  0  0  0
 23 24  1  0  0  0  0
 15 48  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
 14 47  1  0  0  0  0
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 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
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 13 46  1  0  0  0  0
 19 53  1  0  0  0  0
 19 54  1  0  0  0  0
  5 34  1  0  0  0  0
 20 55  1  0  0  0  0
 20 56  1  0  0  0  0
 21 57  1  1  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  4 33  1  1  0  0  0
 18 52  1  0  0  0  0
 17 49  1  0  0  0  0
 17 50  1  0  0  0  0
 17 51  1  0  0  0  0
 10 39  1  0  0  0  0
 24 58  1  0  0  0  0
 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(\C([H])=C([H])/[C@](O[H])(C([H])([H])C([H])([H])C2=C([H])[C@]([H])(OC2=O)C([H])([H])C(=C([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C1([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O6/c1-14(2)22(26)9-6-17-13-18(28-20(17)24)12-15(3)19(27-16(4)23)7-8-21(5,25)10-11-22/h10-11,13-14,18-19,25-26H,3,6-9,12H2,1-2,4-5H3/b11-10-/t18-,19-,21+,22-/m1/s1

> <INCHI_KEY>
RSJMCYXPPOHMKE-SLBAXPMTSA-N

> <FORMULA>
C22H32O6

> <MOLECULAR_WEIGHT>
392.492

> <EXACT_MASS>
392.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.429247780771455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,5Z,7S,10R,13R)-4,7-dihydroxy-7-methyl-11-methylidene-15-oxo-4-(propan-2-yl)-14-oxabicyclo[11.2.1]hexadeca-1(16),5-dien-10-yl acetate

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.7388793110000007

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.148445434796997

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.43333083568604

> <JCHEM_PKA_STRONGEST_BASIC>
-2.94101568786873

> <JCHEM_POLAR_SURFACE_AREA>
93.05999999999999

> <JCHEM_REFRACTIVITY>
106.96579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5Z,7S,10R,13R)-4,7-dihydroxy-4-isopropyl-7-methyl-11-methylidene-15-oxo-14-oxabicyclo[11.2.1]hexadeca-1(16),5-dien-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
   -2.2544   -2.2372    4.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1802   -1.4214    3.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629   -1.8863    1.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857   -3.3632    1.5781 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7785   -3.7894    1.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1828   -4.0747    0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207   -4.4974    0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0188   -3.7099   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2315   -2.1906   -0.4502 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9407   -1.5734   -0.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0374   -1.4899   -1.6004 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3121   -1.4929   -2.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558   -2.0425   -1.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568   -1.9741    0.8723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035   -1.0731    1.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8582    0.1046    2.0346 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5759    1.2516    2.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    0.6255    0.7726 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -0.3655    2.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6021    0.5455    2.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    0.0524    3.5353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9815    0.8065    3.1386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1484    2.0097    3.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3813    2.6793    3.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    2.4887    4.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2016   -3.8780   -0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0134   -3.9757   -1.6179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -3.5389    0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8916   -1.2735    1.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5124   -1.6616    1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8759   -4.0333    2.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2938   -3.8320    2.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834   -4.4924    1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -5.5477    0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9936   -4.2051   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163   -3.8517   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4424   -1.8568   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1412   -0.4297   -1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1705   -2.5072   -3.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3347   -1.0058   -2.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941   -0.9388   -3.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411   -3.0801   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0466   -1.9941   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9905   -1.4537   -2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -2.6934    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4715   -1.2049    2.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4680    1.5644    2.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864    0.9706    3.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9357    2.1380    2.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0975   -0.1322    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -1.3519    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901   -0.5068    3.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931    0.6673    1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437    1.5558    3.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116    0.2267    4.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065    3.6472    3.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2578    2.0628    3.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2823    2.8477    2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 21  2  1  0
 11 13  1  0
  2  1  2  3
  9 14  1  0
  2  3  1  0
 15 16  1  0
  3  4  1  0
  4  5  1  0
 14 15  2  0
  6 26  1  0
 16 19  1  0
  4 28  1  0
 28 26  1  0
 26 27  2  0
  7  6  1  0
 16 18  1  6
  9 11  1  0
 16 17  1  0
  6  5  2  0
  9 10  1  1
  8  9  1  0
 21 22  1  0
 19 20  1  0
 22 23  1  0
 11 12  1  0
 23 25  2  0
 20 21  1  0
 23 24  1  0
 15 48  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
 14 47  1  0
 11 40  1  1
 12 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 19 53  1  0
 19 54  1  0
  5 34  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  1
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  1
 18 52  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 10 39  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.254  -2.237   4.419  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.180  -1.421   3.350  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.463  -1.886   1.928  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.186  -3.363   1.578  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.779  -3.789   1.775  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.183  -4.075   0.618  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.221  -4.497   0.359  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.019  -3.710  -0.704  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.232  -2.191  -0.450  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.941  -1.573  -0.376  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.037  -1.490  -1.600  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.312  -1.493  -2.955  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.456  -2.042  -1.802  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.957  -1.974   0.872  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.804  -1.073   1.865  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.858   0.105   2.035  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.576   1.252   2.755  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.470   0.626   0.773  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.625  -0.366   2.834  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.602   0.546   2.722  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.819   0.052   3.535  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.982   0.807   3.139  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.148   2.010   3.749  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.381   2.679   3.224  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.414   2.489   4.601  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.202  -3.878  -0.419  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.013  -3.976  -1.618  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.382  -3.539   0.167  0.00  0.00           O+0
HETATM   29  H   UNK     0      -2.536  -3.282   4.343  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.058  -1.871   5.424  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.892  -1.274   1.220  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.512  -1.662   1.695  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.876  -4.033   2.102  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.294  -3.832   2.739  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.783  -4.492   1.301  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.195  -5.548   0.040  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.994  -4.205  -0.798  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.516  -3.852  -1.667  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.442  -1.857  -1.168  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.141  -0.430  -1.327  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.171  -2.507  -3.340  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.335  -1.006  -2.892  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.894  -0.939  -3.701  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.441  -3.080  -2.149  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.047  -1.994  -0.883  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.990  -1.454  -2.556  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.763  -2.693   1.035  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.471  -1.205   2.719  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.468   1.564   2.198  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.886   0.971   3.767  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.936   2.138   2.825  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.097  -0.132   0.276  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.340  -1.352   2.458  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.890  -0.507   3.890  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.893   0.667   1.671  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.344   1.556   3.061  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.612   0.227   4.600  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.506   3.647   3.718  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.258   2.063   3.438  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.282   2.848   2.149  0.00  0.00           H+0
CONECT    1    2   29   30                                                  
CONECT    2   21    1    3                                                  
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   28   33                                             
CONECT    5    4    6   34                                                  
CONECT    6   26    7    5                                                  
CONECT    7    8    6   35   36                                             
CONECT    8    7    9   37   38                                             
CONECT    9   14   11   10    8                                             
CONECT   10    9   39                                                       
CONECT   11   13    9   12   40                                             
CONECT   12   11   41   42   43                                             
CONECT   13   11   44   45   46                                             
CONECT   14    9   15   47                                                  
CONECT   15   16   14   48                                                  
CONECT   16   15   19   18   17                                             
CONECT   17   16   49   50   51                                             
CONECT   18   16   52                                                       
CONECT   19   16   20   53   54                                             
CONECT   20   19   21   55   56                                             
CONECT   21    2   22   20   57                                             
CONECT   22   21   23                                                       
CONECT   23   22   25   24                                                  
CONECT   24   23   58   59   60                                             
CONECT   25   23                                                            
CONECT   26    6   28   27                                                  
CONECT   27   26                                                            
CONECT   28    4   26                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   20                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  122    0
END

RDKit          3D

60 61  0  0  0  0  0  0  0  0999 V2000
   -2.2544   -2.2372    4.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1802   -1.4214    3.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629   -1.8863    1.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857   -3.3632    1.5781 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7785   -3.7894    1.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1828   -4.0747    0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207   -4.4974    0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0188   -3.7099   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2315   -2.1906   -0.4502 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9407   -1.5734   -0.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0374   -1.4899   -1.6004 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3121   -1.4929   -2.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558   -2.0425   -1.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568   -1.9741    0.8723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035   -1.0731    1.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8582    0.1046    2.0346 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5759    1.2516    2.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    0.6255    0.7726 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -0.3655    2.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6021    0.5455    2.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    0.0524    3.5353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9815    0.8065    3.1386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1484    2.0097    3.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3813    2.6793    3.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    2.4887    4.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2016   -3.8780   -0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0134   -3.9757   -1.6179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -3.5389    0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5356   -3.2821    4.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0582   -1.8715    5.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8916   -1.2735    1.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5124   -1.6616    1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8759   -4.0333    2.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2938   -3.8320    2.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834   -4.4924    1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -5.5477    0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9936   -4.2051   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163   -3.8517   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4424   -1.8568   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1412   -0.4297   -1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1705   -2.5072   -3.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3347   -1.0058   -2.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941   -0.9388   -3.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411   -3.0801   -2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0466   -1.9941   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9905   -1.4537   -2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -2.6934    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4715   -1.2049    2.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4680    1.5644    2.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864    0.9706    3.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9357    2.1380    2.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0975   -0.1322    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402   -1.3519    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901   -0.5068    3.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931    0.6673    1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437    1.5558    3.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116    0.2267    4.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065    3.6472    3.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2578    2.0628    3.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2823    2.8477    2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 21  2  1  0
 11 13  1  0
  2  1  2  3
  9 14  1  0
  2  3  1  0
 15 16  1  0
  3  4  1  0
  4  5  1  0
 14 15  2  0
  6 26  1  0
 16 19  1  0
  4 28  1  0
 28 26  1  0
 26 27  2  0
  7  6  1  0
 16 18  1  6
  9 11  1  0
 16 17  1  0
  6  5  2  0
  9 10  1  1
  8  9  1  0
 21 22  1  0
 19 20  1  0
 22 23  1  0
 11 12  1  0
 23 25  2  0
 20 21  1  0
 23 24  1  0
 15 48  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
 14 47  1  0
 11 40  1  1
 12 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 19 53  1  0
 19 54  1  0
  5 34  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  1
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  1
 18 52  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 10 39  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₆

Average Mass

392.4920 Da

Monoisotopic Mass

392.21989 Da

IUPAC Name

(4S,5Z,7S,10R,13R)-4,7-dihydroxy-7-methyl-11-methylidene-15-oxo-4-(propan-2-yl)-14-oxabicyclo[11.2.1]hexadeca-1(16),5-dien-10-yl acetate

Traditional Name

(4S,5Z,7S,10R,13R)-4,7-dihydroxy-4-isopropyl-7-methyl-11-methylidene-15-oxo-14-oxabicyclo[11.2.1]hexadeca-1(16),5-dien-10-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(\C([H])=C([H])/[C@](O[H])(C([H])([H])C([H])([H])C2=C([H])[C@]([H])(OC2=O)C([H])([H])C(=C([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C1([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H32O6/c1-14(2)22(26)9-6-17-13-18(28-20(17)24)12-15(3)19(27-16(4)23)7-8-21(5,25)10-11-22/h10-11,13-14,18-19,25-26H,3,6-9,12H2,1-2,4-5H3/b11-10-/t18-,19-,21+,22-/m1/s1

InChI Key

RSJMCYXPPOHMKE-SLBAXPMTSA-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
Croton gratissimus	JEOL database	Langat, M. K., et al, J. Nat. Prod. 74, 2349 (2011)

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	2.21	ALOGPS
logP	2.74	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.43	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.97 m³·mol⁻¹	ChemAxon
Polarizability	42.43 Å³	ChemAxon
Number of Rings	2	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

58140770

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101538653

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
Authors unspecified: Cancer Prevention Overview (PDQ(R)): Health Professional Version. 2002. [PubMed:26389451 ]
Authors unspecified: Spirituality in Cancer Care (PDQ(R)): Health Professional Version. 2002. [PubMed:26389436 ]
Authors unspecified: Oral Cavity, Oropharyngeal, Hypopharyngeal, and Laryngeal Cancer Prevention (PDQ(R)): Health Professional Version. 2002. [PubMed:26389416 ]
Authors unspecified: Adjustment to Cancer: Anxiety and Distress (PDQ(R)): Health Professional Version. 2002. [PubMed:26389397 ]
Authors unspecified: Cancer Pain (PDQ(R)): Health Professional Version. 2002. [PubMed:26389387 ]
Langat, M. K., et al. (2011). Langat, M. K., et al, J. Nat. Prod. 74, 2349 (2011). J. Nat. Prod..

Showing NP-Card for (+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+ (NP0036340)

MOL for NP0036340 ((+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

3D MOL for NP0036340 ((+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

3D SDF for NP0036340 ((+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

3D-SDF for NP0036340 ((+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

PDB for NP0036340 ((+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

3D PDB for NP0036340 ((+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

SMILES for NP0036340 ((+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

INCHI for NP0036340 ((+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

Structure for NP0036340 ((+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

3D Structure for NP0036340 ((+)-(1S*,4S*,7R*,10R*)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

Showing NP-Card for (+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+ (NP0036340)

MOL for NP0036340 ((+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

3D MOL for NP0036340 ((+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

3D SDF for NP0036340 ((+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

3D-SDF for NP0036340 ((+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

PDB for NP0036340 ((+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

3D PDB for NP0036340 ((+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

SMILES for NP0036340 ((+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

INCHI for NP0036340 ((+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

Structure for NP0036340 ((+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)

3D Structure for NP0036340 ((+)-(1S,4S,7R,10R)-7-acetoxy-1,4-dihydroxycembra-2E,8(19),11Z-trien-2+)