NP-MRD: Showing NP-Card for (-)-Ptilosteroid A (NP0081468)

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Record Information

Version

2.0

Created at

2022-04-29 02:28:34 UTC

Updated at

2022-04-29 02:28:34 UTC

NP-MRD ID

NP0081468

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Ptilosteroid A

Description

[(1S,2R,4S,5R,6R,7R,10R,11S,12S,13R,14R,15S)-14-ethenyl-5,6,12,13-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-4-yl]oxidanesulfonic acid belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. (-)-Ptilosteroid A is found in Ptilocaulis spiculifer. Based on a literature review very few articles have been published on [(1S,2R,4S,5R,6R,7R,10R,11S,12S,13R,14R,15S)-14-ethenyl-5,6,12,13-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-4-yl]oxidanesulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204282D          

 30 33  0  0  1  0            999 V2000
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1329   -3.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -2.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480   -0.8192    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601   -0.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5932   -0.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3028   -1.6314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0204   -3.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5060   -2.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8244   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 10 13  1  6  0  0  0
  9 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
  7 19  1  6  0  0  0
  3 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
  1 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 24 27  1  6  0  0  0
 23 28  1  6  0  0  0
 28 29  2  0  0  0  0
 21 30  1  1  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
    5.4570    2.5375   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5020    1.9560    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0150    0.6313    0.2713 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1575   -0.3935    1.3763 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2098    0.1984    2.6341 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9737   -1.3176    1.2189 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1204   -1.2542    2.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2265   -0.8511   -0.0201 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7734   -1.1616    0.0639 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4142   -2.0246   -1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0303   -2.4109   -1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -1.2817   -0.8255 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3528   -1.8003   -0.6995 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4348   -2.7786    0.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831   -0.6671   -0.4172 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0269   -0.8331    0.7493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5825    0.6743   -0.3244 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5543    1.5905    0.0051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8035    2.8053   -1.0776 S   0  0  2  0  0  6  0  0  0  0  0  0
   -5.0201    4.1503   -0.4057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0904    2.5157   -1.8058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6122    2.9061   -2.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004    0.5549    0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5144   -0.4958    0.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4418   -1.4694    1.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1331    0.0196    0.0619 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2958    1.1499    0.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7634    1.3580    0.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365    0.6126   -0.0599 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3680    1.2268   -1.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9148    2.0682   -0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8540    3.5294    0.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0856    2.4656    1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5406    0.2013   -0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1142   -0.9751    1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096    0.8983    2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2783   -2.3870    1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0165   -2.1051    2.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7324   -1.3490   -0.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6243   -1.8281    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0238   -2.9460   -1.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6831   -1.5152   -2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644   -2.6941   -2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503   -3.3467   -0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253   -0.5764   -1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6373   -2.2684   -1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6806   -3.6759   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0462   -0.5573   -1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6712   -1.5954    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643    0.9942   -1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    3.4730   -1.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0491    0.3328    1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0826    1.5709    0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000   -1.1043    2.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4255   -1.4383    2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775   -2.4984    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818    0.4043   -0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643    1.0129    1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1464    2.0954    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325    1.0686    2.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0579    2.4421    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    0.4111   -2.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    1.9849   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019    1.7603   -1.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  1  6
 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
 19 18  1  1
 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  6
  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


  Mrv1652304292204282D          

 30 33  0  0  1  0            999 V2000
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1329   -3.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -2.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480   -0.8192    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601   -0.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5932   -0.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3028   -1.6314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0204   -3.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5060   -2.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8244   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 10 13  1  6  0  0  0
  9 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
  7 19  1  6  0  0  0
  3 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
  1 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 24 27  1  6  0  0  0
 23 28  1  6  0  0  0
 28 29  2  0  0  0  0
 21 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081468

> <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-IEOVDXJYSA-N

> <FORMULA>
C21H34O8S

> <MOLECULAR_WEIGHT>
446.56

> <EXACT_MASS>
446.197439229

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.69363498627841

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

> <ALOGPS_LOGP>
-0.71

> <JCHEM_LOGP>
-0.9721589038162441

> <ALOGPS_LOGS>
-2.04

> <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>
144.51999999999998

> <JCHEM_REFRACTIVITY>
107.8242

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,4S,5R,6R,7R,10R,11S,12S,13R,14R,15S)-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                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.981  -6.510   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.967  -4.155   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.920  -1.258   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0       6.436  -1.529   0.000  0.00  0.00           S+0
HETATM   16  O   UNK     0       7.952  -1.800   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.707  -0.013   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.165  -3.045   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.771  -6.461   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.545  -4.581   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.139  -1.573   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
CONECT    1    2   22                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    2    8   19                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19    7                                                            
CONECT   20    3   21   25                                                  
CONECT   21   20   22   23   30                                             
CONECT   22   21    1                                                       
CONECT   23   21   24   28                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25                                                            
CONECT   27   24                                                            
CONECT   28   23   29                                                       
CONECT   29   28                                                            
CONECT   30   21                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
[(1S,2R,4S,5R,6R,7R,10R,11S,12S,13R,14R,15S)-14-Ethenyl-5,6,12,13-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-4-yl]oxidanesulfonate	Generator
[(1S,2R,4S,5R,6R,7R,10R,11S,12S,13R,14R,15S)-14-Ethenyl-5,6,12,13-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-4-yl]oxidanesulphonate	Generator
[(1S,2R,4S,5R,6R,7R,10R,11S,12S,13R,14R,15S)-14-Ethenyl-5,6,12,13-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-4-yl]oxidanesulphonic acid	Generator

Chemical Formula

C₂₁H₃₄O₈S

Average Mass

446.5600 Da

Monoisotopic Mass

446.19744 Da

IUPAC Name

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

Traditional Name

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

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-IEOVDXJYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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

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

Molecular Framework

Aliphatic 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	-0.71	ALOGPS
logP	-0.97	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.82 m³·mol⁻¹	ChemAxon
Polarizability	46.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163105725

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Ptilosteroid A (NP0081468)

MOL for NP0081468 ((-)-Ptilosteroid A)

3D MOL for NP0081468 ((-)-Ptilosteroid A)

3D SDF for NP0081468 ((-)-Ptilosteroid A)

3D-SDF for NP0081468 ((-)-Ptilosteroid A)

PDB for NP0081468 ((-)-Ptilosteroid A)

3D PDB for NP0081468 ((-)-Ptilosteroid A)

SMILES for NP0081468 ((-)-Ptilosteroid A)

INCHI for NP0081468 ((-)-Ptilosteroid A)

Structure for NP0081468 ((-)-Ptilosteroid A)

3D Structure for NP0081468 ((-)-Ptilosteroid A)