U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H46O
Molecular Weight 386.6535
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHOLESTEROL

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)CCCC(C)C

InChI

InChIKey=HVYWMOMLDIMFJA-DPAQBDIFSA-N
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

HIDE SMILES / InChI
Molecular Formula C27H46O
Molecular Weight 386.6535
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:21:21 UTC 2023
Edited
by admin
on Fri Dec 15 15:21:21 UTC 2023
Record UNII
97C5T2UQ7J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHOLESTEROL
EP   HSDB   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
CHOLESTEROL [MI]
Common Name English
CHOLESTEROL [IARC]
Common Name English
CHOLESTEROL [USP-RS]
Common Name English
Cholesterol [WHO-DD]
Common Name English
NSC-8798
Code English
CHOLESTEROL [VANDF]
Common Name English
CHOLESTEROL [JAN]
Common Name English
CHOLESTEROL [MART.]
Common Name English
PROVITAMIN-D
Common Name English
LIDINITE
Common Name English
DYTHOL
Common Name English
CHOLESTEROL [II]
Common Name English
ALF component cholesterol
Common Name English
Army Liposome Formulation component cholesterol
Common Name English
CHOLESTEROL [INCI]
Common Name English
Cholest-5-en-3β-ol
Systematic Name English
CHOLESTERINUM
HPUS  
Common Name English
CHOLESTEROL [EP MONOGRAPH]
Common Name English
CHOLESTERINUM [HPUS]
Common Name English
LIDINIT
Common Name English
CHOLEST-5-EN-3-OL (3.BETA.)-
Common Name English
CHOLESTEROL [HSDB]
Common Name English
ALFQ component cholesterol
Common Name English
Classification Tree Code System Code
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CFR 21 CFR 862.1175
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IARC Cholesterol
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NCI_THESAURUS C68342
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Code System Code Type Description
ECHA (EC/EINECS)
200-353-2
Created by admin on Fri Dec 15 15:21:21 UTC 2023 , Edited by admin on Fri Dec 15 15:21:21 UTC 2023
PRIMARY
HSDB
7106
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PRIMARY
CHEBI
16113
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PRIMARY
WIKIPEDIA
CHOLESTEROL
Created by admin on Fri Dec 15 15:21:21 UTC 2023 , Edited by admin on Fri Dec 15 15:21:21 UTC 2023
PRIMARY
DAILYMED
97C5T2UQ7J
Created by admin on Fri Dec 15 15:21:21 UTC 2023 , Edited by admin on Fri Dec 15 15:21:21 UTC 2023
PRIMARY
NSC
8798
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PRIMARY
DRUG BANK
DB04540
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PRIMARY
SMS_ID
100000078528
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PRIMARY
MERCK INDEX
m3478
Created by admin on Fri Dec 15 15:21:21 UTC 2023 , Edited by admin on Fri Dec 15 15:21:21 UTC 2023
PRIMARY Merck Index
CAS
57-88-5
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PRIMARY
ChEMBL
CHEMBL112570
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PRIMARY
NCI_THESAURUS
C369
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PRIMARY
PUBCHEM
5997
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PRIMARY
EPA CompTox
DTXSID3022401
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PRIMARY
FDA UNII
97C5T2UQ7J
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PRIMARY
MESH
D002784
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PRIMARY
EVMPD
SUB12480MIG
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PRIMARY
RS_ITEM_NUM
1131960
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PRIMARY
RXCUI
2438
Created by admin on Fri Dec 15 15:21:21 UTC 2023 , Edited by admin on Fri Dec 15 15:21:21 UTC 2023
PRIMARY RxNorm
Related Record Type Details
CHOLESTEROL 24-HYDROXYLASE
METABOLIC ENZYME -> SUBSTRATE
CALENDULA OFFICINALIS FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER terpenoid
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 1
TRANSPORTER -> SUBSTRATE
CYTOCHROME P450 27A1
METABOLIC ENZYME -> SUBSTRATE
Structure of CHOLESTEROL, H-3
LABELED -> NON-LABELED
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Structure of PAMAQUESIDE
INHIBITOR OF ABSORPTION->TARGET
ATP-BINDING CASSETTE SUB-FAMILY A MEMBER 1
TRANSPORTER -> SUBSTRATE
CHOLESTEROL SIDE-CHAIN CLEAVAGE ENZYME, MITOCHONDRIAL
METABOLIC ENZYME -> SUBSTRATE
CHOLESTEROL 7-ALPHA-MONOOXYGENASE
METABOLIC ENZYME -> SUBSTRATE
CHOLESTEROL 7-ALPHA-MONOOXYGENASE
METABOLIC ENZYME -> SUBSTRATE
Structure of TIQUESIDE
INHIBITOR OF ABSORPTION->TARGET
Structure of HYZETIMIBE
INHIBITOR OF ABSORPTION->TARGET
Structure of Ezetimibe
INHIBITOR OF ABSORPTION->TARGET
Related Record Type Details
Structure of COPROSTANONE
METABOLITE -> PARENT
Structure of 24-HYDROXYCHOLESTEROL
METABOLITE -> PARENT
In human brain
Structure of CHOLEST-5-ENE-3.BETA.,26-DIOL, (25R)-
METABOLITE -> PARENT
PREDOMINANTLY METABOLIZED IN MACROPHAGES
MAJOR
Structure of Pregnenolone
METABOLITE -> PARENT
In steroidogenic tissues
Structure of 25-HYDROXYCHOLESTEROL
METABOLITE -> PARENT
25-HYDROXYCHOLESTEROL activates the ER-localized enzyme ACAT to induce internalization of accessible cholesterol on the plasma membrane and restricts SARS-CoV-2 S protein-mediated fusion which inhibits virus replication
Structure of 4.BETA.-HYDROXYCHOLESTEROL
METABOLITE -> PARENT
Structure of 7.ALPHA.-HYDROXYCHOLESTEROL
METABOLITE -> PARENT
Related Record Type Details
Structure of CHOLESTEROL
ACTIVE MOIETY
ALLOSTERIC ACTIVATOR
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