NP-MRD: Showing NP-Card for [(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid (NP0280844)

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Record Information

Version

2.0

Created at

2022-09-09 06:51:41 UTC

Updated at

2022-09-09 06:51:41 UTC

NP-MRD ID

NP0280844

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Halistanol disulfate B belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. [(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid was first documented in 1996 (PMID: 8786367). Based on a literature review very few articles have been published on Halistanol disulfate B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092208512D          

 36 39  0  0  1  0            999 V2000
    6.9960   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 35  1  0  0  0  0
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M  END

     RDKit          3D

 80 83  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309092208512D          

 36 39  0  0  1  0            999 V2000
    6.9960   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.7123   -3.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4574   -2.9388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9053   -3.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6504   -2.7673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0984   -3.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2914   -3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0365   -2.4242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4234   -2.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  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  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  2  0  0  0  0
 25 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 11 35  1  0  0  0  0
  8 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0280844

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H44O8S2/c1-5-6-7-8-17(2)20-11-12-21-19-10-9-18-15-23(33-35(27,28)29)24(34-36(30,31)32)16-26(18,4)22(19)13-14-25(20,21)3/h5,17-24H,1,6-16H2,2-4H3,(H,27,28,29)(H,30,31,32)/t17-,18+,19+,20-,21+,22+,23+,24+,25-,26+/m1/s1

> <INCHI_KEY>
LAZSRKWQJGJJAW-AMIYGGGRSA-N

> <FORMULA>
C26H44O8S2

> <MOLECULAR_WEIGHT>
548.75

> <EXACT_MASS>
548.247760725

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
59.978013868721014

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2S,4S,5S,7S,10R,11S,14R,15R)-14-[(2R)-hept-6-en-2-yl]-2,15-dimethyl-4-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxidanesulfonic acid

> <JCHEM_LOGP>
5.962529358333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
-1.3954418695550848

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.0401386736774496

> <JCHEM_POLAR_SURFACE_AREA>
127.2

> <JCHEM_REFRACTIVITY>
136.60709999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2S,4S,5S,7S,10R,11S,14R,15R)-14-[(2R)-hept-6-en-2-yl]-2,15-dimethyl-4-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      13.059  -3.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.393  -4.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.726  -3.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.060  -4.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.394  -3.899   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.728  -4.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.728  -6.209   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.061  -3.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.222  -2.367   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.729  -2.047   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.499  -3.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.005  -3.701   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.035  -2.556   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.542  -2.877   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.018  -4.341   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.524  -4.661   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.000  -6.126   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      31.506  -6.446   0.000  0.00  0.00           O+0
HETATM   19  S   UNK     0      32.537  -5.302   0.000  0.00  0.00           S+0
HETATM   20  O   UNK     0      33.567  -4.157   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      33.681  -6.332   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      31.392  -4.271   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      28.969  -7.271   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      29.445  -8.735   0.000  0.00  0.00           O+0
HETATM   25  S   UNK     0      28.415  -9.880   0.000  0.00  0.00           S+0
HETATM   26  O   UNK     0      27.270  -8.849   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      29.559 -10.910   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      27.384 -11.024   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      27.463  -6.950   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.987  -5.486   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.957  -6.630   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.481  -5.166   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      24.450  -6.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      22.944  -5.990   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.468  -4.525   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      21.324  -5.556   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   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   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   23   30                                                       
CONECT   30   29   15   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   12   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   11    8   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Halistanol disulfuric acid b	Generator
Halistanol disulphate b	Generator
Halistanol disulphuric acid b	Generator

Chemical Formula

C₂₆H₄₄O₈S₂

Average Mass

548.7500 Da

Monoisotopic Mass

548.24776 Da

IUPAC Name

[(1S,2S,4S,5S,7S,10R,11S,14R,15R)-14-[(2R)-hept-6-en-2-yl]-2,15-dimethyl-4-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxidanesulfonic acid

Traditional Name

[(1S,2S,4S,5S,7S,10R,11S,14R,15R)-14-[(2R)-hept-6-en-2-yl]-2,15-dimethyl-4-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H44O8S2/c1-5-6-7-8-17(2)20-11-12-21-19-10-9-18-15-23(33-35(27,28)29)24(34-36(30,31)32)16-26(18,4)22(19)13-14-25(20,21)3/h5,17-24H,1,6-16H2,2-4H3,(H,27,28,29)(H,30,31,32)/t17-,18+,19+,20-,21+,22+,23+,24+,25-,26+/m1/s1

InChI Key

LAZSRKWQJGJJAW-AMIYGGGRSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Not Available

Direct Parent

Steroids and steroid derivatives

Alternative Parents

Substituents

Cholane-skeleton
Sulfated steroid skeleton
Steroid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	5.96	ChemAxon
pKa (Strongest Acidic)	-2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.2 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.61 m³·mol⁻¹	ChemAxon
Polarizability	59.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

154387

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

177306

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Patil AD, Freyer AJ, Breen A, Carte B, Johnson RK: Halistanol disulfate B, a novel sulfated sterol from the sponge Pachastrella sp.: inhibitor of endothelin converting enzyme. J Nat Prod. 1996 Jun;59(6):606-8. doi: 10.1021/np9601770. [PubMed:8786367 ]
LOTUS database [Link]

Showing NP-Card for [(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid (NP0280844)

MOL for NP0280844 ([(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

3D MOL for NP0280844 ([(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

3D SDF for NP0280844 ([(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

3D-SDF for NP0280844 ([(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

PDB for NP0280844 ([(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

3D PDB for NP0280844 ([(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

SMILES for NP0280844 ([(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

INCHI for NP0280844 ([(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

Structure for NP0280844 ([(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

3D Structure for NP0280844 ([(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-1-[(2r)-hept-6-en-2-yl]-9a,11a-dimethyl-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)