NP-MRD: Showing NP-Card for (2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid (NP0171561)

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Record Information

Version

2.0

Created at

2022-09-03 08:07:37 UTC

Updated at

2022-09-03 08:07:37 UTC

NP-MRD ID

NP0171561

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(25S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oic acid, also known as (3a,5b,7a,12a,25S)-3,7,12-trihydroxycholestan-26-Oate, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. (2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-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 (25S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032210072D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032210072D          

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 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  6  0  0  0
 13 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 26 25  1  1  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  1  0  0  0
  2 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0171561

> <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]3C[C@H](O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16+,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1

> <INCHI_KEY>
CNWPIIOQKZNXBB-TVOMGIAASA-N

> <FORMULA>
C27H46O5

> <MOLECULAR_WEIGHT>
450.66

> <EXACT_MASS>
450.334524581

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.188856488607414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
3.9146180650000013

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.618758291832509

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15944064032502225

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
124.56579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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  O   UNK     0      -1.174 -10.076   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.711  -9.252   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.247  -8.776   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.139 -13.646   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.633 -13.326   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.108 -14.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.584 -16.255   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.091 -16.575   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.567 -18.040   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.121 -15.431   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.645 -13.966   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.676 -12.822   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.200 -11.357   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.230 -10.213   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.452  -7.721   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.785  -6.951   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.452  -9.261   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11    8   18                                             
CONECT   18   17                                                            
CONECT   19   13   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   12   29                                                  
CONECT   29   28                                                            
CONECT   30    2   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(3alpha,5beta,7alpha,12alpha,25S)-3,7,12-Trihydroxycholestan-26-Oic acid	ChEBI
(3a,5b,7a,12a,25S)-3,7,12-Trihydroxycholestan-26-Oate	Generator
(3a,5b,7a,12a,25S)-3,7,12-Trihydroxycholestan-26-Oic acid	Generator
(3alpha,5beta,7alpha,12alpha,25S)-3,7,12-Trihydroxycholestan-26-Oate	Generator
(3Α,5β,7α,12α,25S)-3,7,12-trihydroxycholestan-26-Oate	Generator
(3Α,5β,7α,12α,25S)-3,7,12-trihydroxycholestan-26-Oic acid	Generator
(25S)-3a,7a,12a-Trihydroxy-5b-cholestan-26-Oate	Generator
(25S)-3a,7a,12a-Trihydroxy-5b-cholestan-26-Oic acid	Generator
(25S)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-Oate	Generator
(25S)-3Α,7α,12α-trihydroxy-5β-cholestan-26-Oate	Generator
(25S)-3Α,7α,12α-trihydroxy-5β-cholestan-26-Oic acid	Generator

Chemical Formula

C₂₇H₄₆O₅

Average Mass

450.6600 Da

Monoisotopic Mass

450.33452 Da

IUPAC Name

(2S,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

Traditional Name

(2S,6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

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]3C[C@H](O)[C@]12C

InChI Identifier

InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16+,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1

InChI Key

CNWPIIOQKZNXBB-TVOMGIAASA-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 trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl 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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oic acid (CHEBI:48044 )
C27 bile acids, alcohols, and derivatives (LMST04030152 )

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	3.12	ALOGPS
logP	3.91	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	124.57 m³·mol⁻¹	ChemAxon
Polarizability	53.19 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

21865495

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23657848

PDB ID

Not Available

ChEBI ID

48044

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid (NP0171561)

MOL for NP0171561 ((2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

3D MOL for NP0171561 ((2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

3D SDF for NP0171561 ((2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

3D-SDF for NP0171561 ((2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

PDB for NP0171561 ((2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

3D PDB for NP0171561 ((2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

SMILES for NP0171561 ((2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

INCHI for NP0171561 ((2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

Structure for NP0171561 ((2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)

3D Structure for NP0171561 ((2s,6r)-6-[(1r,3as,3br,4r,5as,7r,9as,9bs,11s,11ar)-4,7,11-trihydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptanoic acid)