NP-MRD: Showing NP-Card for [(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid (NP0218719)

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Record Information

Version

2.0

Created at

2022-09-05 19:28:35 UTC

Updated at

2022-09-05 19:28:35 UTC

NP-MRD ID

NP0218719

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

Description

CHEMBL1208154 belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton. Based on a literature review very few articles have been published on CHEMBL1208154.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052221282D          

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 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  2  0  0  0  0
 22 25  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 13 33  1  0  0  0  0
 10 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0218719

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC(=O)C=C(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)[C@H]4C[C@H](CC[C@]4(C)C3=CC[C@]12C)OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O6S/c1-16(2)12-18(28)13-17(3)21-6-7-22-20-15-25(29)24-14-19(33-34(30,31)32)8-10-27(24,5)23(20)9-11-26(21,22)4/h9,12,17,19-22,24-25,29H,6-8,10-11,13-15H2,1-5H3,(H,30,31,32)/t17-,19+,20+,21-,22+,24-,25+,26-,27-/m1/s1

> <INCHI_KEY>
TWWRXGPUWVXLBB-ASEFAEEDSA-N

> <FORMULA>
C27H42O6S

> <MOLECULAR_WEIGHT>
494.69

> <EXACT_MASS>
494.270210246

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.65831213202638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,5S,7S,8S,10S,11S,14R,15R)-8-hydroxy-2,15-dimethyl-14-[(2R)-6-methyl-4-oxohept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(17)-en-5-yl]oxidanesulfonic acid

> <JCHEM_LOGP>
3.2281968592539503

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.89841150679171

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.437077077120409

> <JCHEM_PKA_STRONGEST_BASIC>
-2.843256053400183

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
133.6689

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,5S,7S,8S,10S,11S,14R,15R)-8-hydroxy-2,15-dimethyl-14-[(2R)-6-methyl-4-oxohept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(17)-en-5-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.320  -5.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.892  -8.295   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   22  S   UNK     0      16.886  -1.622   0.000  0.00  0.00           S+0
HETATM   23  O   UNK     0      17.409  -0.174   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      18.334  -2.146   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      15.437  -1.099   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   33                                                  
CONECT   14   13   15   30                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   20   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   18   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   14   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   13   10   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₆S

Average Mass

494.6900 Da

Monoisotopic Mass

494.27021 Da

IUPAC Name

[(2S,5S,7S,8S,10S,11S,14R,15R)-8-hydroxy-2,15-dimethyl-14-[(2R)-6-methyl-4-oxohept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(17)-en-5-yl]oxidanesulfonic acid

Traditional Name

[(2S,5S,7S,8S,10S,11S,14R,15R)-8-hydroxy-2,15-dimethyl-14-[(2R)-6-methyl-4-oxohept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(17)-en-5-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CC(=O)C=C(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)[C@H]4C[C@H](CC[C@]4(C)C3=CC[C@]12C)OS(O)(=O)=O

InChI Identifier

InChI=1S/C27H42O6S/c1-16(2)12-18(28)13-17(3)21-6-7-22-20-15-25(29)24-14-19(33-34(30,31)32)8-10-27(24,5)23(20)9-11-26(21,22)4/h9,12,17,19-22,24-25,29H,6-8,10-11,13-15H2,1-5H3,(H,30,31,32)/t17-,19+,20+,21-,22+,24-,25+,26-,27-/m1/s1

InChI Key

TWWRXGPUWVXLBB-ASEFAEEDSA-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 cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholestane steroids

Alternative Parents

Substituents

Cholestane-skeleton
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
23-oxosteroid
Bile acid, alcohol, or derivatives
Sulfated steroid skeleton
6-hydroxysteroid
Hydroxysteroid
Oxosteroid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Acryloyl-group
Cyclic alcohol
Enone
Alpha,beta-unsaturated ketone
Organic sulfuric acid or derivatives
Ketone
Secondary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
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	3.23	ChemAxon
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.67 m³·mol⁻¹	ChemAxon
Polarizability	55.66 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	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

25064968

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15484461

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid (NP0218719)

MOL for NP0218719 ([(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

3D MOL for NP0218719 ([(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

3D SDF for NP0218719 ([(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

3D-SDF for NP0218719 ([(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

PDB for NP0218719 ([(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

3D PDB for NP0218719 ([(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

SMILES for NP0218719 ([(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

INCHI for NP0218719 ([(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

Structure for NP0218719 ([(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)

3D Structure for NP0218719 ([(1r,3as,3bs,5s,5as,7s,9as,11ar)-5-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid)