NP-MRD: Showing NP-Card for 7alpha-Hydroxycholesterol (NP0136908)

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Record Information

Version

2.0

Created at

2022-05-12 15:26:48 UTC

Updated at

2022-05-12 15:26:48 UTC

NP-MRD ID

NP0136908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7alpha-Hydroxycholesterol

Description

7Alpha-Hydroxycholesterol, also known as cholest-5-ene-3b,7a-diol or 7ALPHAOHCHOL, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7alpha-hydroxycholesterol is considered to be a sterol lipid molecule. 7Alpha-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 7alpha-Hydroxycholesterol is found in Antipathes dichotoma, Mus musculus and Subergorgia suberosa. 7alpha-Hydroxycholesterol was first documented in 2007 (PMID: 16634125). The 7alpha-hydroxy derivative of cholesterol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304202022192D          

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M  END

     RDKit          3D

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  Mrv1652304202022192D          

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M  END
> <DATABASE_ID>
NP0136908

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1

> <INCHI_KEY>
OYXZMSRRJOYLLO-RVOWOUOISA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.663

> <EXACT_MASS>
402.349780721

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.28342350245964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

> <ALOGPS_LOGP>
5.61

> <JCHEM_LOGP>
5.960031693666668

> <ALOGPS_LOGS>
-5.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.197128213956123

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.204233421519334

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8269276784512555

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
122.05499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.76e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8666.6228668.943   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.6338666.617   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8666.6268662.754   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8658.6368662.754   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8663.9638664.313   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8665.2928666.617   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8666.6228664.313   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8661.3018665.841   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8659.9678665.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8659.9678663.531   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8661.3018662.761   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.6348663.531   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.6348665.071   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.2938668.166   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9598667.396   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.9598665.856   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.2938665.086   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.9638662.761   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.2978663.531   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.6278667.396   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.6278665.856   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.0918665.380   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.9978666.626   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.0918667.872   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.0918669.412   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8669.4278670.178   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.7608669.412   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.0958670.178   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8673.4318669.412   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8674.7648670.178   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8673.4318667.872   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8666.7598670.178   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0    8669.4278668.638   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2   13                                                            
CONECT    3   19                                                            
CONECT    4   10                                                            
CONECT    5   16                                                            
CONECT    6   17                                                            
CONECT    7   21                                                            
CONECT    8    9   13                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    4                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13    8   12    2   16                                             
CONECT   14   15   20                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17    5   13                                             
CONECT   17   16   19    6   21                                             
CONECT   18   19   12                                                       
CONECT   19   18    3   17                                                  
CONECT   20   21   24   14    1                                             
CONECT   21   20   22   17    7                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   25   33   20   23                                             
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   25                                                            
CONECT   33   24                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
7alpha-Hydroxy-cholesterol	ChEBI
Cholest-5-ene-3beta,7alpha-diol	ChEBI
7a-Hydroxy-cholesterol	Generator
7Α-hydroxy-cholesterol	Generator
Cholest-5-ene-3b,7a-diol	Generator
Cholest-5-ene-3β,7α-diol	Generator
7a-Hydroxycholesterol	Generator
7Α-hydroxycholesterol	Generator
7 alpha-Hydroxycholesterol	HMDB
Cholest-5-en-3 beta,7 alpha-diol	HMDB
(3beta,7alpha)-Cholest-5-ene-3,7-diol	HMDB
(3Β,7α)-cholest-5-ene-3,7-diol	HMDB
7alpha-Hydroxycholest-5-en-3beta-ol	HMDB
7AlphaOHChol	HMDB
7Α-hydroxycholest-5-en-3β-ol	HMDB
7ΑOHChol	HMDB
7alpha-Hydroxycholesterol	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Mass

402.6630 Da

Monoisotopic Mass

402.34978 Da

IUPAC Name

(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

Traditional Name

(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1

InChI Key

OYXZMSRRJOYLLO-RVOWOUOISA-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

Species Name	Source	Reference
Antipathes dichotoma	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Subergorgia suberosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
7-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

7alpha-hydroxy steroid (CHEBI:17500 )
oxysterol (CHEBI:17500 )
Cholesterol and derivatives (C03594 )
Cholesterol and derivatives (LMST01010013 )

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	5.61	ALOGPS
logP	5.96	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.06 m³·mol⁻¹	ChemAxon
Polarizability	51.28 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	No	ChemAxon

External Links

HMDB ID

HMDB0001496

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022655

KNApSAcK ID

Not Available

Chemspider ID

96891

KEGG Compound ID

C03594

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

7α-Hydroxycholesterol

METLIN ID

Not Available

PubChem Compound

107722

PDB ID

Not Available

ChEBI ID

17500

Good Scents ID

Not Available

References

General References

Ferderbar S, Pereira EC, Apolinario E, Bertolami MC, Faludi A, Monte O, Calliari LE, Sales JE, Gagliardi AR, Xavier HT, Abdalla DS: Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus. Diabetes Metab Res Rev. 2007 Jan;23(1):35-42. doi: 10.1002/dmrr.645. [PubMed:16634125 ]

Showing NP-Card for 7alpha-Hydroxycholesterol (NP0136908)

MOL for NP0136908 (7alpha-Hydroxycholesterol)

3D MOL for NP0136908 (7alpha-Hydroxycholesterol)

3D SDF for NP0136908 (7alpha-Hydroxycholesterol)

3D-SDF for NP0136908 (7alpha-Hydroxycholesterol)

PDB for NP0136908 (7alpha-Hydroxycholesterol)

3D PDB for NP0136908 (7alpha-Hydroxycholesterol)

SMILES for NP0136908 (7alpha-Hydroxycholesterol)

INCHI for NP0136908 (7alpha-Hydroxycholesterol)

Structure for NP0136908 (7alpha-Hydroxycholesterol)

3D Structure for NP0136908 (7alpha-Hydroxycholesterol)