7alpha-hydroxycholesterol (CHEBI:17500)

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CHEBI:17500 - 7α-hydroxycholesterol

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ChEBI Name	7α-hydroxycholesterol

ChEBI ID	CHEBI:17500

ChEBI ASCII Name	7alpha-hydroxycholesterol

Definition	The 7α-hydroxy derivative of cholesterol.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:20801, CHEBI:12263, CHEBI:2293, CHEBI:89281, CHEBI:13980, CHEBI:58167

Supplier Information	ZINC000016343212

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

5JK - Ideal conformer

Mrv1927 01202215153D

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Time for openFile(5JK - Ideal conformer

Mrv1927 01202215153D

75 78 0 0 0 0 999 V2000

0.7170 0.6760 0.8750 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6580 0.0440 -0.5170 C 0 0 2 0 0 0 0 0 0 0 0 0

0.0110 1.0090 -1.4930 C 0 0 1 0 0 0 0 0 0 0 0 0

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-3.5310 0.6350 0.0180 C 0 0 1 0 0 0 0 0 0 0 0 0

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-4.4570 1.2720 -1.0220 C 0 0 1 0 0 0 0 0 0 0 0 0

-5.7640 1.6940 -0.3460 C 0 0 1 0 0 0 0 0 0 0 0 0

-6.4830 0.4600 0.2010 C 0 0 2 0 0 0 0 0 0 0 0 0

-7.7420 0.8480 0.7530 O 0 0 0 0 0 0 0 0 0 0 0 0

-5.6250 -0.1880 1.2920 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.2520 -0.4820 0.7120 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.7690 -1.6820 0.8500 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4290 -2.0910 0.3130 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.5890 -2.6630 -0.9860 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.5230 -0.8570 0.2220 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.2300 -1.2290 -0.4810 C 0 0 2 0 0 0 0 0 0 0 0 0

0.6740 -2.2160 0.2660 C 0 0 1 0 0 0 0 0 0 0 0 0

2.0730 -1.9420 -0.3520 C 0 0 1 0 0 0 0 0 0 0 0 0

2.0330 -0.4910 -0.9020 C 0 0 2 0 0 0 0 0 0 0 0 0

3.1380 0.3500 -0.2600 C 0 0 2 0 0 0 0 0 0 0 0 0

3.0600 1.7840 -0.7870 C 0 0 0 0 0 0 0 0 0 0 0 0

4.5030 -0.2480 -0.6090 C 0 0 1 0 0 0 0 0 0 0 0 0

5.6000 0.5170 0.1330 C 0 0 1 0 0 0 0 0 0 0 0 0

6.9640 -0.0810 -0.2160 C 0 0 1 0 0 0 0 0 0 0 0 0

8.0620 0.6830 0.5270 C 0 0 1 0 0 0 0 0 0 0 0 0

7.9010 0.4720 2.0330 C 0 0 0 0 0 0 0 0 0 0 0 0

9.4320 0.1680 0.0830 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2940 0.8950 1.2180 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1930 -0.0180 1.5690 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2940 1.5990 0.8310 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6390 1.8920 -1.6130 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1330 0.5220 -2.4570 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1830 1.9360 0.0420 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8570 2.0790 -1.5940 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4740 -0.2640 -1.6000 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7130 2.5450 0.5880 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1130 2.0260 1.5570 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5230 1.2680 1.8140 H 0 0 0 0 0 0 0 0 0 0 0 0

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-5.5440 2.3780 0.4730 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.4030 2.1930 -1.0740 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.6450 -0.2550 -0.6060 H 0 0 0 0 0 0 0 0 0 0 0 0

-8.3380 1.2670 0.1170 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.5290 0.4940 2.1370 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.0910 -1.1170 1.6210 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.3600 -2.4180 1.3750 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9780 -2.8250 0.9810 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1550 -3.4470 -1.0040 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3130 -0.4690 1.2180 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4350 -1.5780 -1.4930 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6770 -2.0040 1.3350 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3630 -3.2430 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8430 -2.0270 0.4140 H 0 0 0 0 0 0 0 0 0 0 0 0

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2.1430 -0.4950 -1.9870 H 0 0 0 0 0 0 0 0 0 0 0 0

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2.0880 2.2100 -0.5380 H 0 0 0 0 0 0 0 0 0 0 0 0

3.8480 2.3830 -0.3290 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1890 1.7810 -1.8690 H 0 0 0 0 0 0 0 0 0 0 0 0

4.5260 -1.2970 -0.3130 H 0 0 0 0 0 0 0 0 0 0 0 0

4.6690 -0.1700 -1.6840 H 0 0 0 0 0 0 0 0 0 0 0 0

5.5760 1.5650 -0.1630 H 0 0 0 0 0 0 0 0 0 0 0 0

5.4340 0.4390 1.2080 H 0 0 0 0 0 0 0 0 0 0 0 0

6.9880 -1.1300 0.0800 H 0 0 0 0 0 0 0 0 0 0 0 0

7.1310 -0.0040 -1.2910 H 0 0 0 0 0 0 0 0 0 0 0 0

7.9820 1.7460 0.2990 H 0 0 0 0 0 0 0 0 0 0 0 0

6.9250 0.8390 2.3500 H 0 0 0 0 0 0 0 0 0 0 0 0

7.9810 -0.5910 2.2610 H 0 0 0 0 0 0 0 0 0 0 0 0

8.6830 1.0160 2.5620 H 0 0 0 0 0 0 0 0 0 0 0 0

9.5470 0.3190 -0.9910 H 0 0 0 0 0 0 0 0 0 0 0 0

10.2140 0.7130 0.6120 H 0 0 0 0 0 0 0 0 0 0 0 0

9.5120 -0.8950 0.3100 H 0 0 0 0 0 0 0 0 0 0 0 0

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11 10 1 0 0 0 0

12 10 1 0 0 0 0

12 13 1 0 0 0 0

14 15 1 0 0 0 0

14 13 2 0 0 0 0

15 17 1 0 0 0 0

10 9 1 0 0 0 0

13 6 1 0 0 0 0

19 18 1 0 0 0 0

19 20 1 0 0 0 0

17 18 1 0 0 0 0

17 5 1 0 0 0 0

18 2 1 0 0 0 0

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5 6 1 0 0 0 0

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4 3 1 0 0 0 0

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28 27 1 0 0 0 0

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27 29 1 0 0 0 0

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4 36 1 0 0 0 0

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7 39 1 0 0 0 0

7 40 1 0 0 0 0

8 41 1 0 0 0 0

8 42 1 0 0 0 0

9 43 1 0 0 0 0

9 44 1 0 0 0 0

10 45 1 6 0 0 0

11 46 1 0 0 0 0

12 47 1 0 0 0 0

12 48 1 0 0 0 0

14 49 1 0 0 0 0

15 50 1 1 0 0 0

16 51 1 0 0 0 0

17 52 1 1 0 0 0

18 53 1 6 0 0 0

19 54 1 0 0 0 0

19 55 1 0 0 0 0

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20 57 1 0 0 0 0

21 58 1 6 0 0 0

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23 60 1 0 0 0 0

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28 70 1 0 0 0 0

28 71 1 0 0 0 0

28 72 1 0 0 0 0

29 73 1 0 0 0 0

29 74 1 0 0 0 0

29 75 1 0 0 0 0

M END): 23 ms

reading 75 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

75 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License

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Formula

C27H46O2

Net Charge

Average Mass

402.663

Monoisotopic Mass

402.34978

InChI

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

InChIKey

OYXZMSRRJOYLLO-RVOWOUOISA-N

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in cerebrospinal fluid (UBERON:0001359). See: PubMed

Roles Classification
Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	7α-hydroxycholesterol (CHEBI:17500) has functional parent cholesterol (CHEBI:16113) 7α-hydroxycholesterol (CHEBI:17500) has role mouse metabolite (CHEBI:75771) 7α-hydroxycholesterol (CHEBI:17500) is a 3β-hydroxy-Δ⁵-steroid (CHEBI:1722) 7α-hydroxycholesterol (CHEBI:17500) is a 7α-hydroxy steroid (CHEBI:36843) 7α-hydroxycholesterol (CHEBI:17500) is a oxysterol (CHEBI:53030)

IUPAC Name

cholest-5-ene-3β,7α-diol

Synonyms	Sources
(3β,7α)-cholest-5-ene-3,7-diol	ChemIDplus
5-cholesten-3β,7α-diol	MetaCyc
7-alpha-hydroxycholesterol	ChemIDplus
7α-hydroxy-cholesterol	LIPID MAPS
7alpha-Hydroxycholesterol	KEGG COMPOUND
7α-hydroxycholesterol	UniProt
cholest-5-en-3β,7α-diol	ChemIDplus
Cholest-5-ene-3beta,7alpha-diol	KEGG COMPOUND

Manual Xrefs	Databases
5JK	PDBeChem
7%CE%B1-Hydroxycholesterol	Wikipedia
96891	ChemSpider
C03594	KEGG COMPOUND
CPD-266	MetaCyc
FDB022655	FooDB
HMDB0001496	HMDB
LMST01010013	LIPID MAPS
View more database links

Registry Number	Type	Source
566-26-7	CAS Registry Number	ChemIDplus

Citations	Types	Sources
10529092	PubMed citation	Europe PMC
14571793	PubMed citation	Europe PMC
15576852	PubMed citation	Europe PMC
16376175	PubMed citation	Europe PMC
16455124	PubMed citation	Europe PMC
16634125	PubMed citation	Europe PMC
17364953	PubMed citation	Europe PMC
17386651	PubMed citation	Europe PMC
24370436	PubMed citation	Europe PMC
27075612	PubMed citation	Europe PMC
27268273	PubMed citation	Europe PMC
31781930	PubMed citation	Europe PMC
7557870	PubMed citation	Europe PMC
8558093	PubMed citation	Europe PMC
9632680	PubMed citation	Europe PMC
9882415	PubMed citation	Europe PMC

Last Modified

20 January 2022

CHEBI:17500 - 7α-hydroxycholesterol

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