NP-MRD: Showing NP-Card for 3beta-Hydroxy-5-cholestenoic acid (NP0136232)

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Record Information

Version

2.0

Created at

2022-05-12 15:09:12 UTC

Updated at

2022-05-12 15:09:12 UTC

NP-MRD ID

NP0136232

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta-Hydroxy-5-cholestenoic acid

Description

3Beta-Hydroxy-5-cholestenoic acid, also known as (25R)-3b-hydroxycholest-5-en-26-Oate or 3β-hydroxy-5-cholestenoate, belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 3Beta-Hydroxy-5-cholestenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062012582D          

 34 37  0  0  0  0            999 V2000
 9998.7140 9999.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5816 9998.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4451 9996.6224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2922 9997.4538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0031 9998.6852    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7140 9997.4538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8694 9998.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1550 9997.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1550 9997.0350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.8694 9996.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0039 9999.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2896 9999.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2896 9998.2785    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.0039 9997.8661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.5787 9997.8600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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10001.648310000.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10003.077710001.4211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.3619 9999.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.789110000.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.2188 9999.7710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
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 14 20  1  0  0  0  0
 20  6  1  6  0  0  0
 11 19  1  0  0  0  0
 19  1  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304062012582D          

 34 37  0  0  0  0            999 V2000
 9998.7140 9999.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0136232

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h8,17-18,20-24,28H,5-7,9-16H2,1-4H3,(H,29,30)/t17-,18-,20+,21+,22-,23+,24+,26+,27-/m1/s1

> <INCHI_KEY>
WVXOMPRLWLXFAP-KQOPCUSDSA-N

> <FORMULA>
C27H44O3

> <MOLECULAR_WEIGHT>
416.646

> <EXACT_MASS>
416.329045277

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.552377269474334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
6.048614447666667

> <ALOGPS_LOGS>
-5.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.20428950550382

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.8289209924155

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972440282926124

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
122.30779999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.85e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    8664.2668666.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.2868664.212   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8656.2988660.362   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8661.6128661.914   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8662.9398664.212   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8664.2668661.914   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8658.9568663.442   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8657.6238662.672   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8657.6238661.132   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8658.9568660.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.9418665.763   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.6078664.993   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.6078663.453   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.9418662.683   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.2808662.672   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.2808661.132   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8661.6148660.362   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.9478661.132   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.2758664.993   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.2748663.453   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.7398662.977   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.6448664.223   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8665.7398665.469   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8665.7398667.009   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8667.0758667.779   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.4088667.009   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8669.7438667.779   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8671.0768667.009   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8672.4128667.779   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8673.7488667.009   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0    8672.4128669.319   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0    8671.0768665.469   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8664.4068667.779   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0    8667.0758666.239   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2   15                                                            
CONECT    3    9                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6   20                                                            
CONECT    7    8   15                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    3                                                  
CONECT   10    9   16                                                       
CONECT   11   12   19                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15    4                                             
CONECT   14   13   18    5   20                                             
CONECT   15   16    7    2   13                                             
CONECT   16   15   17   10                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   20   23   11    1                                             
CONECT   20   19   21   14    6                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   34   19   22                                             
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28                                                            
CONECT   33   24                                                            
CONECT   34   23                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
3b-Hydroxy-5-cholestenoate	Generator
3b-Hydroxy-5-cholestenoic acid	Generator
3beta-Hydroxy-5-cholestenoate	Generator
3Β-hydroxy-5-cholestenoate	Generator
3Β-hydroxy-5-cholestenoic acid	Generator
(25R)-3b-Hydroxycholest-5-en-26-Oate	HMDB
(25R)-3b-Hydroxycholest-5-en-26-Oic acid	HMDB
(25R)-3beta-Hydroxycholest-5-en-26-Oate	HMDB
(25R)-3Β-hydroxycholest-5-en-26-Oate	HMDB
(25R)-3Β-hydroxycholest-5-en-26-Oic acid	HMDB
5-Cholesten-3-ol-25-carboxylic acid	HMDB
(3beta)-3-Hydroxycholest-5-en-26-Oic acid	HMDB
(3beta,25R)-3-Hydroxycholest-5-en-26-Oic acid	HMDB
(3Β)-3-hydroxycholest-5-en-26-Oic acid	HMDB
(3Β,25R)-3-hydroxycholest-5-en-26-Oic acid	HMDB
3beta-Hydroxycholest-5-en-26-Oic acid	HMDB
3beta-Hydroxycholest-5-en-27-Oic acid	HMDB
3Β-hydroxycholest-5-en-26-Oic acid	HMDB
3Β-hydroxycholest-5-en-27-Oic acid	HMDB
3beta-Hydroxy-5-cholestenoic acid	HMDB

Chemical Formula

C₂₇H₄₄O₃

Average Mass

416.6460 Da

Monoisotopic Mass

416.32905 Da

IUPAC Name

(2R,6R)-6-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid

Traditional Name

(2R,6R)-6-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)C(O)=O

InChI Identifier

InChI=1S/C27H44O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h8,17-18,20-24,28H,5-7,9-16H2,1-4H3,(H,29,30)/t17-,18-,20+,21+,22-,23+,24+,26+,27-/m1/s1

InChI Key

WVXOMPRLWLXFAP-KQOPCUSDSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
Steroid acid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
Delta-5-steroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxycholest-5-en-26-oic acid (CHEBI:86378 )
C27 bile acids, alcohols, and derivatives (LMST04030072 )

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	5.57	ALOGPS
logP	6.05	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.31 m³·mol⁻¹	ChemAxon
Polarizability	51.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0012453

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

25942571

KEGG Compound ID

C17333

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

40579073

PDB ID

Not Available

ChEBI ID

86378

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3beta-Hydroxy-5-cholestenoic acid (NP0136232)

MOL for NP0136232 (3beta-Hydroxy-5-cholestenoic acid)

3D MOL for NP0136232 (3beta-Hydroxy-5-cholestenoic acid)

3D SDF for NP0136232 (3beta-Hydroxy-5-cholestenoic acid)

3D-SDF for NP0136232 (3beta-Hydroxy-5-cholestenoic acid)

PDB for NP0136232 (3beta-Hydroxy-5-cholestenoic acid)

3D PDB for NP0136232 (3beta-Hydroxy-5-cholestenoic acid)

SMILES for NP0136232 (3beta-Hydroxy-5-cholestenoic acid)

INCHI for NP0136232 (3beta-Hydroxy-5-cholestenoic acid)

Structure for NP0136232 (3beta-Hydroxy-5-cholestenoic acid)

3D Structure for NP0136232 (3beta-Hydroxy-5-cholestenoic acid)