NP-MRD: Showing NP-Card for fascioquinol A (NP0040305)

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Record Information

Version

2.0

Created at

2021-06-20 22:30:28 UTC

Updated at

2021-06-30 00:14:08 UTC

NP-MRD ID

NP0040305

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fascioquinol A

Provided By

JEOL Database JEOL Logo

Description

2-{[(1R,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-(sulfooxy)benzen-1-olate belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton. fascioquinol A is found in Fasciospongia sp. fascioquinol A was first documented in 2011 (Zhang, H., et al.). Based on a literature review very few articles have been published on 2-{[(1R,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-(sulfooxy)benzen-1-olate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100303D          

 69 72  0  0  0  0            999 V2000
   -2.7616    2.7508   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004    1.5019    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424    0.5047    0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6210   -0.8398    1.1449 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1122   -1.1070    0.9564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6288   -2.5325    1.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8974   -2.7218    2.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202   -3.6400    0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8518   -5.0495    0.8810 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6208   -5.1254    0.5033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5192   -4.0991    1.2374 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7541   -4.5362    2.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -4.1459    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8888   -2.6698    1.0855 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.2474   -0.1682    1.1933 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.6045    3.1855    1.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
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 13 53  1  0  0  0  0
 13 54  1  0  0  0  0
 32 69  1  0  0  0  0
M  CHG  1  28  -1
M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
   -2.7616    2.7508   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004    1.5019    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424    0.5047    0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1122   -1.1070    0.9564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6288   -2.5325    1.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8974   -2.7218    2.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202   -3.6400    0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 52  1  0
 13 53  1  0
 13 54  1  0
 32 69  1  0
M  CHG  1  28  -1
M  END


  Mrv1652306212100303D          

 69 72  0  0  0  0            999 V2000
   -2.7616    2.7508   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004    1.5019    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424    0.5047    0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6210   -0.8398    1.1449 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1122   -1.1070    0.9564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6288   -2.5325    1.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8974   -2.7218    2.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202   -3.6400    0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8518   -5.0495    0.8810 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6208   -5.1254    0.5033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5192   -4.0991    1.2374 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7541   -4.5362    2.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -4.1459    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8888   -2.6698    1.0855 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7170   -1.5303    1.7055 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2474   -0.1682    1.1933 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2604    0.1382    1.4085 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4900    0.5098    2.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    1.3787    0.4760 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0159    2.7072    0.9362 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3455    3.7125   -0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2161    5.0008   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0686    5.9628   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5662    7.1672   -0.9085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    8.4331   -1.9362 S   0  0  1  0  0  6  0  0  0  0  0  0
   -0.8918    7.9292   -3.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2804    9.4524   -1.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0062    8.7722   -1.9082 O   0  5  0  0  0  1  0  0  0  0  0  0
    0.9438    5.6427   -2.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5374    4.3799   -2.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447    3.4308   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645    2.2128   -1.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6796    3.5978    0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427    2.9777   -1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8239    2.6444   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1143    0.6390    0.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1967   -1.5882    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9300   -0.9147    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698   -1.1562   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8029   -2.2103    3.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0588   -3.7674    3.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -2.3723    3.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348   -3.4073   -0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4666   -3.6547    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9970   -5.4115    1.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -5.7366    0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9838   -6.1455    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6984   -4.9633   -0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8301   -4.7167    3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3388   -3.7950    3.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154   -5.4781    2.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485   -3.7571   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2787   -5.1748    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6575   -3.5661    1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219   -2.4854   -0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6916   -1.5527    2.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -1.6268    1.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738    0.5988    1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721   -0.1283    0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1208    1.3673    3.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5309    0.7736    3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2103   -0.2913    3.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166    1.1388   -0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6045    3.1855    1.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    2.5051    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949    5.2722    0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1871    6.3663   -2.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2284    4.1673   -2.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    2.2001   -1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 19 63  1  6  0  0  0
  9  8  1  0  0  0  0
 14 55  1  6  0  0  0
 10 11  1  0  0  0  0
 19 20  1  0  0  0  0
 11 14  1  0  0  0  0
 20 21  1  0  0  0  0
  6  8  1  0  0  0  0
 21 31  2  0  0  0  0
  6 14  1  0  0  0  0
 31 30  1  0  0  0  0
 14 15  1  0  0  0  0
 30 29  2  0  0  0  0
 15 16  1  0  0  0  0
 29 23  1  0  0  0  0
  2 19  1  0  0  0  0
 23 22  2  0  0  0  0
 22 21  1  0  0  0  0
 11 12  1  1  0  0  0
  5 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 16  1  0  0  0  0
  2  1  1  0  0  0  0
 17 19  1  0  0  0  0
 23 24  1  0  0  0  0
  5  4  1  0  0  0  0
 24 25  1  0  0  0  0
  2  3  2  0  0  0  0
 25 28  1  6  0  0  0
  6  7  1  1  0  0  0
 25 26  2  0  0  0  0
  9 10  1  0  0  0  0
 25 27  2  0  0  0  0
  3  4  1  0  0  0  0
 11 13  1  0  0  0  0
  5 39  1  6  0  0  0
 31 32  1  0  0  0  0
  9 45  1  0  0  0  0
  9 46  1  0  0  0  0
 10 47  1  0  0  0  0
 10 48  1  0  0  0  0
  8 43  1  0  0  0  0
  8 44  1  0  0  0  0
 15 56  1  0  0  0  0
 15 57  1  0  0  0  0
  3 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
 16 58  1  0  0  0  0
 16 59  1  0  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
  7 42  1  0  0  0  0
 20 64  1  0  0  0  0
 20 65  1  0  0  0  0
 30 68  1  0  0  0  0
 29 67  1  0  0  0  0
 22 66  1  0  0  0  0
 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
 12 51  1  0  0  0  0
 18 60  1  0  0  0  0
 18 61  1  0  0  0  0
 18 62  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
 13 52  1  0  0  0  0
 13 53  1  0  0  0  0
 13 54  1  0  0  0  0
 32 69  1  0  0  0  0
M  CHG  1  28  -1
M  END
> <DATABASE_ID>
NP0040305

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C([H])=C(O[S]([O-])(=O)=O)C([H])=C1[H])C([H])([H])[C@]1([H])C(=C([H])C([H])([H])[C@@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C([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])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O5S/c1-17-7-10-23-25(4,14-11-22-24(2,3)12-6-13-26(22,23)5)20(17)16-18-15-19(8-9-21(18)27)31-32(28,29)30/h7-9,15,20,22-23,27H,6,10-14,16H2,1-5H3,(H,28,29,30)/p-1/t20-,22+,23+,25+,26+/m1/s1

> <INCHI_KEY>
UMJDWJAZBYWNCO-GDWSFLSUSA-M

> <FORMULA>
C26H37O5S

> <MOLECULAR_WEIGHT>
461.64

> <EXACT_MASS>
461.236719045

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.32985981170435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(1R,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-hydroxyphenyl sulfate

> <ALOGPS_LOGP>
5.21

> <JCHEM_LOGP>
6.5178590456666665

> <ALOGPS_LOGS>
-6.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.752002466681956

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.7754844345253593

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9538847460212

> <JCHEM_POLAR_SURFACE_AREA>
86.66000000000001

> <JCHEM_REFRACTIVITY>
126.04899999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1R,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-4,4a,5,6,7,8a,9,10-octahydro-1H-phenanthren-1-yl]methyl}-4-hydroxyphenyl sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
   -2.7616    2.7508   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004    1.5019    0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424    0.5047    0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6210   -0.8398    1.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1122   -1.1070    0.9564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6288   -2.5325    1.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8974   -2.7218    2.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202   -3.6400    0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8518   -5.0495    0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208   -5.1254    0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5192   -4.0991    1.2374 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7541   -4.5362    2.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039   -4.1459    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8888   -2.6698    1.0855 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7170   -1.5303    1.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474   -0.1682    1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2604    0.1382    1.4085 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4900    0.5098    2.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    1.3787    0.4760 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0159    2.7072    0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3455    3.7125   -0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2161    5.0008   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0686    5.9628   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5662    7.1672   -0.9085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    8.4331   -1.9362 S   0  0  1  0  0  6  0  0  0  0  0  0
   -0.8918    7.9292   -3.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2804    9.4524   -1.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0062    8.7722   -1.9082 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9438    5.6427   -2.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5374    4.3799   -2.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447    3.4308   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645    2.2128   -1.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6796    3.5978    0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427    2.9777   -1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8239    2.6444   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1143    0.6390    0.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1967   -1.5882    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9300   -0.9147    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698   -1.1562   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8029   -2.2103    3.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0588   -3.7674    3.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0774   -2.3723    3.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348   -3.4073   -0.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4666   -3.6547    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9970   -5.4115    1.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -5.7366    0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9838   -6.1455    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6984   -4.9633   -0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8301   -4.7167    3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3388   -3.7950    3.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154   -5.4781    2.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485   -3.7571   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2787   -5.1748    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6575   -3.5661    1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219   -2.4854   -0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6916   -1.5527    2.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -1.6268    1.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738    0.5988    1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721   -0.1283    0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1208    1.3673    3.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5309    0.7736    3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2103   -0.2913    3.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166    1.1388   -0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6045    3.1855    1.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    2.5051    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949    5.2722    0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1871    6.3663   -2.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2284    4.1673   -2.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    2.2001   -1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
 19 63  1  6
  9  8  1  0
 14 55  1  6
 10 11  1  0
 19 20  1  0
 11 14  1  0
 20 21  1  0
  6  8  1  0
 21 31  2  0
  6 14  1  0
 31 30  1  0
 14 15  1  0
 30 29  2  0
 15 16  1  0
 29 23  1  0
  2 19  1  0
 23 22  2  0
 22 21  1  0
 11 12  1  1
  5 17  1  0
 17 18  1  1
 17 16  1  0
  2  1  1  0
 17 19  1  0
 23 24  1  0
  5  4  1  0
 24 25  1  0
  2  3  2  0
 25 28  1  6
  6  7  1  1
 25 26  2  0
  9 10  1  0
 25 27  2  0
  3  4  1  0
 11 13  1  0
  5 39  1  6
 31 32  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
  8 43  1  0
  8 44  1  0
 15 56  1  0
 15 57  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
 16 58  1  0
 16 59  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
 20 64  1  0
 20 65  1  0
 30 68  1  0
 29 67  1  0
 22 66  1  0
 12 49  1  0
 12 50  1  0
 12 51  1  0
 18 60  1  0
 18 61  1  0
 18 62  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 13 52  1  0
 13 53  1  0
 13 54  1  0
 32 69  1  0
M  CHG  1  28  -1
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.762   2.751  -0.312  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.200   1.502   0.315  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.042   0.505   0.643  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.621  -0.840   1.145  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.112  -1.107   0.956  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.629  -2.533   1.473  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.897  -2.722   2.987  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.420  -3.640   0.713  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.852  -5.050   0.881  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.621  -5.125   0.503  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.519  -4.099   1.237  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.754  -4.536   2.695  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.904  -4.146   0.539  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.889  -2.670   1.085  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.717  -1.530   1.706  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.247  -0.168   1.193  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.260   0.138   1.409  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.490   0.510   2.896  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.674   1.379   0.476  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.016   2.707   0.936  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.346   3.712  -0.150  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.216   5.001  -0.101  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.069   5.963  -1.079  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.566   7.167  -0.909  0.00  0.00           O+0
HETATM   25  S   UNK     0      -0.416   8.433  -1.936  0.00  0.00           S+0
HETATM   26  O   UNK     0      -0.892   7.929  -3.224  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.280   9.452  -1.343  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.006   8.772  -1.908  0.00  0.00           O-1
HETATM   29  C   UNK     0       0.944   5.643  -2.112  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.537   4.380  -2.163  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.245   3.431  -1.183  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.865   2.213  -1.218  0.00  0.00           O+0
HETATM   33  H   UNK     0      -2.680   3.598   0.374  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.243   2.978  -1.248  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.824   2.644  -0.560  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.114   0.639   0.510  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.197  -1.588   0.589  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.930  -0.915   2.191  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.970  -1.156  -0.137  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.803  -2.210   3.319  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.059  -3.767   3.258  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.077  -2.372   3.615  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.435  -3.407  -0.360  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.467  -3.655   1.041  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.997  -5.412   1.903  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.419  -5.737   0.241  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.984  -6.146   0.683  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.698  -4.963  -0.581  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.830  -4.717   3.243  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.339  -3.795   3.248  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.315  -5.478   2.730  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.849  -3.757  -0.484  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.279  -5.175   0.478  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.658  -3.566   1.081  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.922  -2.485  -0.002  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.692  -1.553   2.798  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.772  -1.627   1.429  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.874   0.599   1.662  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.472  -0.128   0.120  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.121   1.367   3.197  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.531   0.774   3.104  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.210  -0.291   3.578  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.317   1.139  -0.535  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.605   3.186   1.706  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.972   2.505   1.430  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.895   5.272   0.704  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.187   6.366  -2.886  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.228   4.167  -2.972  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.450   2.200  -1.992  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2   19    1    3                                                  
CONECT    3    2    4   36                                                  
CONECT    4    5    3   37   38                                             
CONECT    5    6   17    4   39                                             
CONECT    6    5    8   14    7                                             
CONECT    7    6   40   41   42                                             
CONECT    8    9    6   43   44                                             
CONECT    9    8   10   45   46                                             
CONECT   10   11    9   47   48                                             
CONECT   11   10   14   12   13                                             
CONECT   12   11   49   50   51                                             
CONECT   13   11   52   53   54                                             
CONECT   14   55   11    6   15                                             
CONECT   15   14   16   56   57                                             
CONECT   16   15   17   58   59                                             
CONECT   17    5   18   16   19                                             
CONECT   18   17   60   61   62                                             
CONECT   19   63   20    2   17                                             
CONECT   20   19   21   64   65                                             
CONECT   21   20   31   22                                                  
CONECT   22   23   21   66                                                  
CONECT   23   29   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   28   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   30   23   67                                                  
CONECT   30   31   29   68                                                  
CONECT   31   21   30   32                                                  
CONECT   32   31   69                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    7                                                            
CONECT   41    7                                                            
CONECT   42    7                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   10                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   13                                                            
CONECT   54   13                                                            
CONECT   55   14                                                            
CONECT   56   15                                                            
CONECT   57   15                                                            
CONECT   58   16                                                            
CONECT   59   16                                                            
CONECT   60   18                                                            
CONECT   61   18                                                            
CONECT   62   18                                                            
CONECT   63   19                                                            
CONECT   64   20                                                            
CONECT   65   20                                                            
CONECT   66   22                                                            
CONECT   67   29                                                            
CONECT   68   30                                                            
CONECT   69   32                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  144    0
END

RDKit          3D

69 72  0  0  0  0  0  0  0  0999 V2000
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 18 61  1  0
 18 62  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 13 52  1  0
 13 53  1  0
 13 54  1  0
 32 69  1  0
M  CHG  1  28  -1
M  END

View in JSmol

Synonyms

Value	Source
2-{[(1R,4ar,4BS,8as,10as)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-(sulfooxy)benzen-1-olic acid	Generator
2-{[(1R,4ar,4BS,8as,10as)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-(sulphooxy)benzen-1-olate	Generator
2-{[(1R,4ar,4BS,8as,10as)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-(sulphooxy)benzen-1-olic acid	Generator

Chemical Formula

C₂₆H₃₇O₅S

Average Mass

461.6400 Da

Monoisotopic Mass

461.23672 Da

IUPAC Name

3-{[(1R,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-hydroxyphenyl sulfate

Traditional Name

3-{[(1R,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-4,4a,5,6,7,8a,9,10-octahydro-1H-phenanthren-1-yl]methyl}-4-hydroxyphenyl sulfate

CAS Registry Number

Not Available

SMILES

[H]OC1=C(C([H])=C(O[S]([O-])(=O)=O)C([H])=C1[H])C([H])([H])[C@]1([H])C(=C([H])C([H])([H])[C@@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C([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])C([H])([H])[H]

InChI Identifier

InChI=1S/C26H38O5S/c1-17-7-10-23-25(4,14-11-22-24(2,3)12-6-13-26(22,23)5)20(17)16-18-15-19(8-9-21(18)27)31-32(28,29)30/h7-9,15,20,22-23,27H,6,10-14,16H2,1-5H3,(H,28,29,30)/p-1/t20-,22+,23+,25+,26+/m1/s1

InChI Key

UMJDWJAZBYWNCO-GDWSFLSUSA-M

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Fasciospongia sp.	JEOL database	Zhang, H., et al, Tetrahedron 67, 2591 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Isocopalane and spongiane diterpenoids

Alternative Parents

Substituents

Isocopalane diterpenoid
Hydrophenanthrene
Phenanthrene
Phenylsulfate
Arylsulfate
Phenoxy compound
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Organic sulfuric acid or derivatives
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Organic anion
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

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	5.21	ALOGPS
logP	6.52	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	-1.8	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.66 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.05 m³·mol⁻¹	ChemAxon
Polarizability	51.33 Å³	ChemAxon
Number of Rings	4	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

28288607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53328563

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang, H., et al. (2011). Zhang, H., et al, Tetrahedron 67, 2591 (2011). Tetrahedron.

Showing NP-Card for fascioquinol A (NP0040305)

MOL for NP0040305 (fascioquinol A)

3D MOL for NP0040305 (fascioquinol A)

3D SDF for NP0040305 (fascioquinol A)

3D-SDF for NP0040305 (fascioquinol A)

PDB for NP0040305 (fascioquinol A)

3D PDB for NP0040305 (fascioquinol A)

SMILES for NP0040305 (fascioquinol A)

INCHI for NP0040305 (fascioquinol A)

Structure for NP0040305 (fascioquinol A)

3D Structure for NP0040305 (fascioquinol A)