NP-MRD: Showing NP-Card for 7b-Hydroxycholesterol (NP0087455)

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Record Information

Version

2.0

Created at

2022-05-11 16:50:08 UTC

Updated at

2022-05-11 16:50:08 UTC

NP-MRD ID

NP0087455

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7b-Hydroxycholesterol

Description

7Beta-Hydroxycholesterol, also known as 7β-hydroxycholest-5-en-3β-ol or cholest-5-ene-3β,7β-diol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7beta-hydroxycholesterol is considered to be a sterol lipid molecule. 7Beta-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 7Beta-Hydroxycholesterol is identified in atheromatous plaques and in plasma of atherosclerotic patients. It exhibites a specific enhancement of oxidative stress and of endonuclease G expression. 7b-Hydroxycholesterol is found in Bombyx mori, Cryptosula pallasiana, Heteroxenia ghardaqensis and Rana temporaria. 7b-Hydroxycholesterol was first documented in 2006 (PMID: 16604541). 7Beta-Hydroxycholesterol induces apoptosis in Caco-2 cells and alters Lysosomal membrane integrity (PMID: 17136497).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652310281916232D          

 33 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END

  Mrv1652310281916232D          

 33 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0087455

> <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-KGZHIOMZSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.11503121648968

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,9R,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,9R,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                                 28-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-OCT-19         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
(3beta,7beta)-Cholest-5-ene-3,7-diol	ChEBI
7-HYDROXYCHOLESTEROL	ChEBI
(3b,7b)-Cholest-5-ene-3,7-diol	Generator
(3Β,7β)-cholest-5-ene-3,7-diol	Generator
7b-Hydroxycholesterol	Generator
7Β-hydroxycholesterol	Generator
5-Cholestene-3beta,7beta-diol	HMDB
Cholest-5-ene-3beta,7beta-diol	HMDB
7 beta-Hydroxycholesterol	HMDB
Cholest-5-en-3beta,7beta-diol	HMDB
7beta-Hydroxycholest-5-en-3beta-ol	HMDB
7Β-hydroxycholest-5-en-3β-ol	HMDB
Cholest-5-ene-3β,7β-diol	HMDB
delta5-Cholestene-3beta,7beta-diol	HMDB
Δ5-cholestene-3β,7β-diol	HMDB
7beta-Hydroxycholesterol	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Mass

402.6529 Da

Monoisotopic Mass

402.34978 Da

IUPAC Name

(1S,2R,5S,9R,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,9R,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-KGZHIOMZSA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bombyx mori	LOTUS Database	35616633
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Cryptosula pallasiana	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Heteroxenia ghardaqensis	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Rana temporaria	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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-alpha-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

oxysterol (CHEBI:42989 )
7beta-hydroxy steroid (CHEBI:42989 )
Cholesterol and derivatives (LMST01010047 )

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	51.12 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

HMDB0006119

DrugBank ID

DB04706

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023832

KNApSAcK ID

Not Available

Chemspider ID

415508

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

473141

PDB ID

HCR

ChEBI ID

42989

Good Scents ID

Not Available

References

General References

Prunet C, Montange T, Vejux A, Laubriet A, Rohmer JF, Riedinger JM, Athias A, Lemaire-Ewing S, Neel D, Petit JM, Steinmetz E, Brenot R, Gambert P, Lizard G: Multiplexed flow cytometric analyses of pro- and anti-inflammatory cytokines in the culture media of oxysterol-treated human monocytic cells and in the sera of atherosclerotic patients. Cytometry A. 2006 May;69(5):359-73. doi: 10.1002/cyto.a.20272. [PubMed:16604541 ]
Roussi S, Gosse F, Aoude-Werner D, Zhang X, Marchioni E, Geoffroy P, Miesch M, Raul F: Mitochondrial perturbation, oxidative stress and lysosomal destabilization are involved in 7beta-hydroxysitosterol and 7beta-hydroxycholesterol triggered apoptosis in human colon cancer cells. Apoptosis. 2007 Jan;12(1):87-96. doi: 10.1007/s10495-006-0485-y. [PubMed:17136497 ]

Showing NP-Card for 7b-Hydroxycholesterol (NP0087455)

MOL for NP0087455 (7b-Hydroxycholesterol)

3D MOL for NP0087455 (7b-Hydroxycholesterol)

3D SDF for NP0087455 (7b-Hydroxycholesterol)

3D-SDF for NP0087455 (7b-Hydroxycholesterol)

PDB for NP0087455 (7b-Hydroxycholesterol)

3D PDB for NP0087455 (7b-Hydroxycholesterol)

SMILES for NP0087455 (7b-Hydroxycholesterol)

INCHI for NP0087455 (7b-Hydroxycholesterol)

Structure for NP0087455 (7b-Hydroxycholesterol)

3D Structure for NP0087455 (7b-Hydroxycholesterol)