NP-MRD: Showing NP-Card for 4-hydroxymilolide C (NP0025758)

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Record Information

Version

1.0

Created at

2021-06-19 17:47:48 UTC

Updated at

2021-06-29 23:50:54 UTC

NP-MRD ID

NP0025758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxymilolide C

Provided By

JEOL Database JEOL Logo

Description

4-hydroxymilolide C is found in Briareum stechei. It was first documented in 2001 (Kwak, J. H., et al.). Based on a literature review very few articles have been published on (1R,2R,3S,4R,6S,8S,9R,10R,12S,14S,15R,18R)-10-(acetyloxy)-14-chloro-2,12-dihydroxy-4,9,18-trimethyl-13-methylidene-17-oxo-5,16,19-trioxapentacyclo[10.6.1.0¹,¹⁵.0³,⁹.0⁴,⁶]Nonadecan-8-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119473D          

 66 70  0  0  0  0            999 V2000
    4.3979   -2.7763   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -2.2292   -1.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449   -2.6003   -3.0162 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7293   -3.7835   -3.9325 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4868   -1.3620   -3.8780 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114   -0.7220   -4.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4704    0.6073   -4.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2856    1.3886   -4.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731    0.9540   -3.9583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1116    2.2901   -3.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6982   -0.2860   -3.1205 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2025   -0.0707   -1.8029 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579   -1.1647   -0.9476 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2328   -0.5915    0.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1954   -1.7707   -0.2952 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0685   -0.8124    0.1825 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6388    0.4228    0.6498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    0.4123    1.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7934    1.7193    2.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -0.5103    2.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1374   -0.5322   -0.8189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8209   -1.9007   -1.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    0.3485   -0.0601 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6719    1.6674    0.2067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2019    2.3392    1.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5930    3.7039    1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0828    1.9203    2.0004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972    0.5238   -0.8761 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2087    1.0836   -2.2257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8811    0.1385   -3.2574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202    0.9997   -2.8256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4737    2.1071   -3.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736    0.2585   -2.1162 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1779   -0.6222   -3.0921 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3286   -0.6588   -4.4263 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364   -2.4974   -0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994   -3.5345   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7960   -3.1223   -2.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860   -1.6582   -4.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628    1.0298   -4.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523    2.5421   -2.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    3.0972   -3.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736    2.3040   -2.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0345   -0.2588   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7795   -2.5655   -0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420   -2.3009    0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4086   -1.3177    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0535    2.4201    2.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5785    1.5558    2.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    2.1317    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1396   -2.6697   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2829   -2.3098   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052   -1.8250   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4529   -0.1420    0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5264    3.6624    1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1021    4.3833    0.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6954    4.0698    2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1678    1.2207   -0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0507   -0.4168   -0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8716    1.8964   -2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189    1.8075   -4.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503    2.4399   -4.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0962    2.9712   -3.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0323    1.0620   -1.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1007   -1.6572   -2.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3006   -0.7719   -4.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  1  0  0  0  0
  9  7  1  0  0  0  0
  7  6  1  0  0  0  0
 11 34  1  0  0  0  0
 21 22  1  6  0  0  0
 16 15  1  0  0  0  0
 34 35  1  0  0  0  0
 15 13  1  0  0  0  0
  2  1  2  3  0  0  0
 13  2  1  0  0  0  0
  9 10  1  0  0  0  0
  2  3  1  0  0  0  0
 31 32  1  6  0  0  0
  3  5  1  0  0  0  0
 33 64  1  1  0  0  0
 29 31  1  0  0  0  0
 11 12  1  1  0  0  0
 29 30  1  0  0  0  0
  7  8  2  0  0  0  0
 31 30  1  0  0  0  0
 23 24  1  0  0  0  0
 33 34  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 28 23  1  0  0  0  0
 18 20  2  0  0  0  0
  5 11  1  0  0  0  0
 18 19  1  0  0  0  0
 31 33  1  0  0  0  0
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 25 27  2  0  0  0  0
 13 12  1  0  0  0  0
  3  4  1  0  0  0  0
 28 29  1  0  0  0  0
 13 14  1  1  0  0  0
  5  6  1  0  0  0  0
 28 58  1  0  0  0  0
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 23 54  1  1  0  0  0
 34 65  1  1  0  0  0
 16 47  1  1  0  0  0
 15 45  1  0  0  0  0
 15 46  1  0  0  0  0
  3 38  1  1  0  0  0
 29 60  1  6  0  0  0
  5 39  1  6  0  0  0
  9 40  1  6  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
 22 53  1  0  0  0  0
 35 66  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
 32 61  1  0  0  0  0
 32 62  1  0  0  0  0
 32 63  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
 19 50  1  0  0  0  0
 26 55  1  0  0  0  0
 26 56  1  0  0  0  0
 26 57  1  0  0  0  0
 14 44  1  0  0  0  0
M  END

     RDKit          3D

 66 70  0  0  0  0  0  0  0  0999 V2000
    4.3979   -2.7763   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -2.2292   -1.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449   -2.6003   -3.0162 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7293   -3.7835   -3.9325 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4868   -1.3620   -3.8780 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114   -0.7220   -4.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4704    0.6073   -4.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2856    1.3886   -4.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6982   -0.2860   -3.1205 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192119473D          

 66 70  0  0  0  0            999 V2000
    4.3979   -2.7763   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -2.2292   -1.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449   -2.6003   -3.0162 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7293   -3.7835   -3.9325 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4868   -1.3620   -3.8780 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114   -0.7220   -4.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4704    0.6073   -4.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2856    1.3886   -4.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731    0.9540   -3.9583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1116    2.2901   -3.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6982   -0.2860   -3.1205 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2025   -0.0707   -1.8029 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2328   -0.5915    0.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1954   -1.7707   -0.2952 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.0236   -0.5103    2.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6719    1.6674    0.2067 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1779   -0.6222   -3.0921 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.5785    1.5558    2.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655    2.1317    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0507   -0.4168   -0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8716    1.8964   -2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189    1.8075   -4.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503    2.4399   -4.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0962    2.9712   -3.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0323    1.0620   -1.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1007   -1.6572   -2.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3006   -0.7719   -4.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9  7  1  0  0  0  0
  7  6  1  0  0  0  0
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  2  1  2  3  0  0  0
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 31 32  1  6  0  0  0
  3  5  1  0  0  0  0
 33 64  1  1  0  0  0
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  7  8  2  0  0  0  0
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  3  4  1  0  0  0  0
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 14 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]2([H])[C@]3(O[C@@]3([H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]2(O[H])O[C@]11[C@]([H])(C(=O)O[C@@]1([H])[C@@]([H])(Cl)C2=C([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H31ClO10/c1-9-16(25)19-24(10(2)20(29)33-19)18(28)17-21(5,15(32-12(4)27)8-23(9,30)35-24)13(31-11(3)26)7-14-22(17,6)34-14/h10,13-19,28,30H,1,7-8H2,2-6H3/t10-,13-,14-,15+,16-,17+,18+,19-,21+,22-,23-,24+/m0/s1

> <INCHI_KEY>
MGZIJJVRXUVFHH-FXFFXEEGSA-N

> <FORMULA>
C24H31ClO10

> <MOLECULAR_WEIGHT>
514.95

> <EXACT_MASS>
514.1605749

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.285060027570616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,4R,6S,8S,9R,10R,12S,14S,15R,18R)-10-(acetyloxy)-14-chloro-2,12-dihydroxy-4,9,18-trimethyl-13-methylidene-17-oxo-5,16,19-trioxapentacyclo[10.6.1.0^{1,15}.0^{3,9}.0^{4,6}]nonadecan-8-yl acetate

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
0.7566098886666663

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.55517150291574

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.367900466049369

> <JCHEM_PKA_STRONGEST_BASIC>
-3.435373660414787

> <JCHEM_POLAR_SURFACE_AREA>
141.12

> <JCHEM_REFRACTIVITY>
116.00430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,4R,6S,8S,9R,10R,12S,14S,15R,18R)-10-(acetyloxy)-14-chloro-2,12-dihydroxy-4,9,18-trimethyl-13-methylidene-17-oxo-5,16,19-trioxapentacyclo[10.6.1.0^{1,15}.0^{3,9}.0^{4,6}]nonadecan-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 70  0  0  0  0  0  0  0  0999 V2000
    4.3979   -2.7763   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -2.2292   -1.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7449   -2.6003   -3.0162 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.2856    1.3886   -4.8781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731    0.9540   -3.9583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1116    2.2901   -3.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6982   -0.2860   -3.1205 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2025   -0.0707   -1.8029 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2328   -0.5915    0.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1779   -0.6222   -3.0921 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.1007   -1.6572   -2.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3006   -0.7719   -4.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
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 32 61  1  0
 32 62  1  0
 32 63  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 14 44  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       4.398  -2.776  -1.092  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.298  -2.229  -1.652  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.745  -2.600  -3.016  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       3.729  -3.784  -3.933  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       2.487  -1.362  -3.878  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.711  -0.722  -4.254  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.470   0.607  -4.415  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.286   1.389  -4.878  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.073   0.954  -3.958  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.112   2.290  -3.224  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.698  -0.286  -3.120  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.203  -0.071  -1.803  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.458  -1.165  -0.948  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.233  -0.592   0.102  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.195  -1.771  -0.295  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.069  -0.812   0.183  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.639   0.423   0.650  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.133   0.412   1.921  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.793   1.719   2.234  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.024  -0.510   2.717  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.137  -0.532  -0.819  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.821  -1.901  -1.131  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.207   0.349  -0.060  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.672   1.667   0.207  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.202   2.339   1.264  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.593   3.704   1.366  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.083   1.920   2.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.497   0.524  -0.876  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.209   1.084  -2.226  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.881   0.139  -3.257  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.820   1.000  -2.826  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.474   2.107  -3.779  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.674   0.259  -2.116  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.178  -0.622  -3.092  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.329  -0.659  -4.426  0.00  0.00           O+0
HETATM   36  H   UNK     0       4.736  -2.497  -0.097  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.999  -3.535  -1.584  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.796  -3.122  -2.858  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.986  -1.658  -4.809  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.463   1.030  -4.865  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.152   2.542  -2.773  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.366   3.097  -3.920  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.874   2.304  -2.436  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.035  -0.259  -0.337  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.780  -2.566  -0.914  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.542  -2.301   0.606  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.409  -1.318   1.036  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.054   2.420   2.626  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.579   1.556   2.978  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.265   2.132   1.338  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.140  -2.670  -1.496  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.283  -2.310  -0.224  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.605  -1.825  -1.886  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.453  -0.142   0.891  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.526   3.662   1.130  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.102   4.383   0.679  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.695   4.070   2.391  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.168   1.221  -0.360  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.051  -0.417  -0.963  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.872   1.896  -2.495  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.719   1.808  -4.507  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.350   2.440  -4.346  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.096   2.971  -3.224  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.032   1.062  -1.740  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.101  -1.657  -2.771  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.301  -0.772  -4.378  0.00  0.00           H+0
CONECT    1    2   36   37                                                  
CONECT    2    1   13    3                                                  
CONECT    3    2    5    4   38                                             
CONECT    4    3                                                            
CONECT    5    3   11    6   39                                             
CONECT    6    7    5                                                       
CONECT    7    9    6    8                                                  
CONECT    8    7                                                            
CONECT    9   11    7   10   40                                             
CONECT   10    9   41   42   43                                             
CONECT   11    9   34   12    5                                             
CONECT   12   11   13                                                       
CONECT   13   15    2   12   14                                             
CONECT   14   13   44                                                       
CONECT   15   16   13   45   46                                             
CONECT   16   15   17   21   47                                             
CONECT   17   16   18                                                       
CONECT   18   17   20   19                                                  
CONECT   19   18   48   49   50                                             
CONECT   20   18                                                            
CONECT   21   22   16   23   33                                             
CONECT   22   21   51   52   53                                             
CONECT   23   24   28   21   54                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   55   56   57                                             
CONECT   27   25                                                            
CONECT   28   23   29   58   59                                             
CONECT   29   31   30   28   60                                             
CONECT   30   29   31                                                       
CONECT   31   32   29   30   33                                             
CONECT   32   31   61   62   63                                             
CONECT   33   64   34   31   21                                             
CONECT   34   11   35   33   65                                             
CONECT   35   34   66                                                       
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    3                                                            
CONECT   39    5                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   32                                                            
CONECT   62   32                                                            
CONECT   63   32                                                            
CONECT   64   33                                                            
CONECT   65   34                                                            
CONECT   66   35                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  140    0
END

RDKit          3D

66 70  0  0  0  0  0  0  0  0999 V2000
    4.3979   -2.7763   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -2.2292   -1.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6982   -0.2860   -3.1205 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.7934    1.7193    2.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -0.5103    2.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1007   -1.6572   -2.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
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 11  9  1  0
  9  7  1  0
  7  6  1  0
 11 34  1  0
 21 22  1  6
 16 15  1  0
 34 35  1  0
 15 13  1  0
  2  1  2  3
 13  2  1  0
  9 10  1  0
  2  3  1  0
 31 32  1  6
  3  5  1  0
 33 64  1  1
 29 31  1  0
 11 12  1  1
 29 30  1  0
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 28 23  1  0
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 21 23  1  0
 25 26  1  0
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 25 27  2  0
 13 12  1  0
  3  4  1  0
 28 29  1  0
 13 14  1  1
  5  6  1  0
 28 58  1  0
 28 59  1  0
 23 54  1  1
 34 65  1  1
 16 47  1  1
 15 45  1  0
 15 46  1  0
  3 38  1  1
 29 60  1  6
  5 39  1  6
  9 40  1  6
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 22 52  1  0
 22 53  1  0
 35 66  1  0
  1 36  1  0
  1 37  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 32 61  1  0
 32 62  1  0
 32 63  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 14 44  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1R,2R,3S,4R,6S,8S,9R,10R,12S,14S,15R,18R)-10-(Acetyloxy)-14-chloro-2,12-dihydroxy-4,9,18-trimethyl-13-methylidene-17-oxo-5,16,19-trioxapentacyclo[10.6.1.0,.0,.0,]nonadecan-8-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₁ClO₁₀

Average Mass

514.9500 Da

Monoisotopic Mass

514.16057 Da

IUPAC Name

(1R,2R,3S,4R,6S,8S,9R,10R,12S,14S,15R,18R)-10-(acetyloxy)-14-chloro-2,12-dihydroxy-4,9,18-trimethyl-13-methylidene-17-oxo-5,16,19-trioxapentacyclo[10.6.1.0^{1,15}.0^{3,9}.0^{4,6}]nonadecan-8-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@@]2([H])[C@]3(O[C@@]3([H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]2(O[H])O[C@]11[C@]([H])(C(=O)O[C@@]1([H])[C@@]([H])(Cl)C2=C([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H31ClO10/c1-9-16(25)19-24(10(2)20(29)33-19)18(28)17-21(5,15(32-12(4)27)8-23(9,30)35-24)13(31-11(3)26)7-14-22(17,6)34-14/h10,13-19,28,30H,1,7-8H2,2-6H3/t10-,13-,14-,15+,16-,17+,18+,19-,21+,22-,23-,24+/m0/s1

InChI Key

MGZIJJVRXUVFHH-FXFFXEEGSA-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
Briareum stechei	JEOL database	Kwak, J. H., et al, J. Nat. Prod. 64, 754 (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	1.59	ALOGPS
logP	0.76	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.37	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	141.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116 m³·mol⁻¹	ChemAxon
Polarizability	49.29 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

29212987

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101117914

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kwak, J. H., et al. (2001). Kwak, J. H., et al, J. Nat. Prod. 64, 754 (2001). J. Nat. Prod..

Showing NP-Card for 4-hydroxymilolide C (NP0025758)

MOL for NP0025758 (4-hydroxymilolide C)

3D MOL for NP0025758 (4-hydroxymilolide C)

3D SDF for NP0025758 (4-hydroxymilolide C)

3D-SDF for NP0025758 (4-hydroxymilolide C)

PDB for NP0025758 (4-hydroxymilolide C)

3D PDB for NP0025758 (4-hydroxymilolide C)

SMILES for NP0025758 (4-hydroxymilolide C)

INCHI for NP0025758 (4-hydroxymilolide C)

Structure for NP0025758 (4-hydroxymilolide C)

3D Structure for NP0025758 (4-hydroxymilolide C)