NP-MRD: Showing NP-Card for [(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid (NP0237383)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 20:30:31 UTC

Updated at

2022-09-06 20:30:32 UTC

NP-MRD ID

NP0237383

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid

Description

Ptilosteroid a belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Thus, ptilosteroid a is considered to be a steroid. [(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid is found in Ptilocaulis spiculifer. [(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid was first documented in 2009 (PMID: 19228002). Based on a literature review very few articles have been published on Ptilosteroid a (PMID: 35419331).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062222302D          

 30 33  0  0  1  0            999 V2000
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5486   -0.4095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7019   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8292   -2.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1623   -3.8638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8719   -2.2395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
    6.1325    0.7824   -0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0174    0.2057   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568   -0.5485   -0.2858 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2924   -0.5928    1.1910 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9088    0.5077    1.7324 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9085   -0.8025    1.8287 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5841    0.2465    2.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9934   -0.8864    0.6708 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5697   -0.4860    0.9103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0497   -1.5114    1.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5175   -1.3715    2.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1392   -1.2763    0.6055 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6110   -1.3999    0.6123 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0228   -1.3741    1.9694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802   -0.3575   -0.0970 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7291    0.6627    0.8211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7716    0.1800   -1.3443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9661    1.5587   -1.4948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7871    1.9778   -2.8510 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.7709    2.3886   -3.9084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6105    0.8968   -3.4434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6995    3.3704   -2.5361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3068   -0.0846   -1.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5740   -0.1266   -0.1840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5775    1.1802    0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246   -0.4898   -0.4333 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5397    0.3212   -1.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699   -0.1388   -1.6245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6612    0.0493   -0.3261 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7160    1.4704    0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7256    1.3141   -1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5642    0.7982    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7666    0.3060   -2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296   -1.6027   -0.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -1.4790    1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4868    0.2879    2.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258   -1.7201    2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3282    0.8683    2.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0774   -1.9076    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587    0.4727    1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4933   -1.5076    2.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507   -2.5299    1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589   -0.6043    2.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -2.3536    2.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392   -2.2075    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9678   -2.4155    0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806   -2.2675    2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3869   -0.7956   -0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2938    0.5471    1.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2665   -0.2732   -2.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7644    3.5464   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211   -1.0544   -2.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678    0.6965   -2.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6127    1.7424    0.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3596    1.8853    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6802    1.1253    1.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1317   -1.5559   -0.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556    0.0999   -2.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5385    1.4039   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9209   -1.2242   -1.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4754    0.3622   -2.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736    1.8477    0.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    2.1034   -0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0850    1.7394    0.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  1  1
 29 28  1  0
 28 27  1  0
 27 26  1  0
 26  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 23  1  0
 23 24  1  0
 24 25  1  1
 17 18  1  0
 18 19  1  0
 19 22  1  0
 19 20  2  0
 19 21  2  0
  9  8  1  0
  8  6  1  0
  6  7  1  0
  6  4  1  0
  4  5  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  8 29  1  0
  3 29  1  0
 24 26  1  0
 24 12  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
 28 60  1  0
 28 61  1  0
 27 58  1  0
 27 59  1  0
 26 57  1  6
  9 40  1  1
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  6
 13 46  1  6
 14 47  1  0
 15 48  1  6
 16 49  1  0
 17 50  1  6
 23 52  1  0
 23 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 22 51  1  0
  8 39  1  6
  6 37  1  1
  7 38  1  0
  4 35  1  6
  5 36  1  0
  3 34  1  6
  2 33  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1652309062222302D          

 30 33  0  0  1  0            999 V2000
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5486   -0.4095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7019   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8292   -2.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1623   -3.8638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8719   -2.2395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0237383

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H]3[C@@H](CC[C@H]4[C@@H](O)[C@@H](O)[C@H](C[C@]34C)OS(O)(=O)=O)[C@@H]1[C@H](O)[C@H](O)[C@@H]2C=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O8S/c1-4-11-16(22)19(25)15-10-5-6-13-17(23)18(24)14(29-30(26,27)28)9-21(13,3)12(10)7-8-20(11,15)2/h4,10-19,22-25H,1,5-9H2,2-3H3,(H,26,27,28)/t10-,11+,12+,13+,14+,15-,16-,17-,18+,19+,20-,21-/m1/s1

> <INCHI_KEY>
QRMSSNGYWMVNBN-CNBQIQBMSA-N

> <FORMULA>
C21H34O8S

> <MOLECULAR_WEIGHT>
446.56

> <EXACT_MASS>
446.197439229

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.77616900141389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,4S,5R,6R,7R,10R,11S,12S,13R,14R,15R)-14-ethenyl-5,6,12,13-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-4-yl]oxidanesulfonic acid

> <JCHEM_LOGP>
-0.9721589038162441

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.981787216594686

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.5619382581198726

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2721038308649595

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
107.8242

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,4S,5R,6R,7R,10R,11S,12S,13R,14R,15R)-14-ethenyl-5,6,12,13-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-4-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.624  -0.764   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.377  -0.716   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   19  S   UNK     0      16.832  -5.696   0.000  0.00  0.00           S+0
HETATM   20  O   UNK     0      18.348  -5.425   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      17.103  -7.212   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      16.561  -4.180   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   29                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   17   24                                                       
CONECT   24   23   12   25   26                                             
CONECT   25   24                                                            
CONECT   26   24    9   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    8    3   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₄O₈S

Average Mass

446.5600 Da

Monoisotopic Mass

446.19744 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@H]4[C@@H](O)[C@@H](O)[C@H](C[C@]34C)OS(O)(=O)=O)[C@@H]1[C@H](O)[C@H](O)[C@@H]2C=C

InChI Identifier

InChI=1S/C21H34O8S/c1-4-11-16(22)19(25)15-10-5-6-13-17(23)18(24)14(29-30(26,27)28)9-21(13,3)12(10)7-8-20(11,15)2/h4,10-19,22-25H,1,5-9H2,2-3H3,(H,26,27,28)/t10-,11+,12+,13+,14+,15-,16-,17-,18+,19+,20-,21-/m1/s1

InChI Key

QRMSSNGYWMVNBN-CNBQIQBMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ptilocaulis spiculifer	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Sulfated steroids

Direct Parent

Sulfated steroids

Alternative Parents

Substituents

Progestogin-skeleton
Sulfated steroid skeleton
Pregnane-skeleton
3-hydroxysteroid
4-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
16-beta-hydroxysteroid
16-hydroxysteroid
3-beta-hydroxysteroid
Sulfuric acid monoester
Cyclitol or derivatives
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Organic sulfuric acid or derivatives
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030212 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00047553

Chemspider ID

26374735

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42640653

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gabant M, Schmitz-Afonso I, Gallard JF, Menou JL, Laurent D, Debitus C, Al-Mourabit A: Sulfated steroids: ptilosteroids A-C and ptilosaponosides A and B from the Solomon Islands marine sponge Ptilocaulis spiculifer. J Nat Prod. 2009 Apr;72(4):760-3. doi: 10.1021/np800758c. [PubMed:19228002 ]
Cai S, Yang Y, Kong Y, Guo Q, Xu Y, Xing P, Sun Y, Qian J, Xu R, Xie L, Hu Y, Wang M, Li M, Tian Y, Mao W: Gut Bacteria Erysipelatoclostridium and Its Related Metabolite Ptilosteroid A Could Predict Radiation-Induced Intestinal Injury. Front Public Health. 2022 Mar 28;10:862598. doi: 10.3389/fpubh.2022.862598. eCollection 2022. [PubMed:35419331 ]
LOTUS database [Link]

Showing NP-Card for [(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid (NP0237383)

MOL for NP0237383 ([(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid)

3D MOL for NP0237383 ([(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid)

3D SDF for NP0237383 ([(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid)

3D-SDF for NP0237383 ([(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid)

PDB for NP0237383 ([(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid)

3D PDB for NP0237383 ([(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid)

SMILES for NP0237383 ([(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid)

INCHI for NP0237383 ([(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid)

Structure for NP0237383 ([(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid)

3D Structure for NP0237383 ([(1r,2r,3s,3as,3br,5ar,6r,7r,8s,9ar,9bs,11ar)-1-ethenyl-2,3,6,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-8-yl]oxidanesulfonic acid)