NP-MRD: Showing NP-Card for (2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid (NP0242025)

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Record Information

Version

2.0

Created at

2022-09-07 02:14:13 UTC

Updated at

2022-09-07 02:14:13 UTC

NP-MRD ID

NP0242025

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid

Description

(25R)-3alpha,7alpha-dihydroxy-5beta-cholestan-26-oic acid, also known as (25R)-3α,7α-dihydroxy-5β-cholestan-26-Oate, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. (2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid is found in Alligator mississippiensis. Based on a literature review very few articles have been published on (25R)-3alpha,7alpha-dihydroxy-5beta-cholestan-26-oic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204142D          

 31 34  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072204142D          

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 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 25 24  1  1  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  1  1  0  0  0
  2 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242025

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17-,18+,19-,20-,21+,22+,23-,24+,26+,27-/m1/s1

> <INCHI_KEY>
ITZYGDKGRKKBSN-RXDNHGQQSA-N

> <FORMULA>
C27H46O4

> <MOLECULAR_WEIGHT>
434.661

> <EXACT_MASS>
434.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.53194551425597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid

> <JCHEM_LOGP>
5.145429132000005

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296339908541825

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.82892261028387

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5356619176938756

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
123.05029999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.118  -5.411   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.118  -6.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.784  -7.721   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.451  -6.951   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.883  -7.721   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.217  -6.951   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.217  -5.411   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.550  -7.721   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.957  -7.094   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.988  -8.239   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.218  -9.572   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.694 -11.037   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.663 -12.181   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.157 -11.861   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.681 -10.397   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.711  -9.252   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.247  -8.776   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.139 -13.646   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.633 -13.326   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.108 -14.790   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.584 -16.255   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.091 -16.575   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.567 -18.040   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -7.121 -15.431   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.645 -13.966   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.676 -12.822   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.200 -11.357   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -8.230 -10.213   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.452  -7.721   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.785  -6.951   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.452  -9.261   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11    8   17                                             
CONECT   17   16                                                            
CONECT   18   13   19   20   25                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   12   28                                                  
CONECT   28   27                                                            
CONECT   29    2   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
(25R)-3a,7a-Dihydroxy-5b-cholestan-26-Oate	Generator
(25R)-3a,7a-Dihydroxy-5b-cholestan-26-Oic acid	Generator
(25R)-3alpha,7alpha-Dihydroxy-5beta-cholestan-26-Oate	Generator
(25R)-3Α,7α-dihydroxy-5β-cholestan-26-Oate	Generator
(25R)-3Α,7α-dihydroxy-5β-cholestan-26-Oic acid	Generator

Chemical Formula

C₂₇H₄₆O₄

Average Mass

434.6610 Da

Monoisotopic Mass

434.33961 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17-,18+,19-,20-,21+,22+,23-,24+,26+,27-/m1/s1

InChI Key

ITZYGDKGRKKBSN-RXDNHGQQSA-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
Alligator mississippiensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha,7alpha-dihydroxy-5beta-cholestan-26-oic acid (CHEBI:48467 )
C27 bile acids, alcohols, and derivatives (LMST04030153 )

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

Not Available

Chemspider ID

21865553

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24755560

PDB ID

Not Available

ChEBI ID

48467

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid (NP0242025)

MOL for NP0242025 ((2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

3D MOL for NP0242025 ((2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

3D SDF for NP0242025 ((2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

3D-SDF for NP0242025 ((2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

PDB for NP0242025 ((2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

3D PDB for NP0242025 ((2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

SMILES for NP0242025 ((2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

INCHI for NP0242025 ((2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

Structure for NP0242025 ((2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

3D Structure for NP0242025 ((2r,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11ar)-4,7-dihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)