1D-chiro-inositol (CHEBI:27372)

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CHEBI:27372 - 1D-chiro-inositol

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ChEBI Name	*1D-chiro-inositol*

ChEBI ID	CHEBI:27372

ChEBI ASCII Name	1D-chiro-inositol

Definition	Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.

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

Submitter	Bijay

Secondary ChEBI IDs	CHEBI:19183, CHEBI:52772, CHEBI:4200

Supplier Information	ChemicalBook:CB1426829, ChemicalBook:CB62130237

Download	Molfile XML SDF

more structures >>

Molfile

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The Resolver thinks Mol

CBU - Ideal conformer

Mrv1927 10072116293D

starting HoverWatcher_5

Time for openFile(CBU - Ideal conformer

Mrv1927 10072116293D

24 24 0 0 0 0 999 V2000

0.7300 -1.0610 -0.1390 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.7710 -1.0400 0.1540 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.3940 0.2120 -0.4660 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.7400 1.4580 0.1340 C 0 0 2 0 0 0 0 0 0 0 0 0

0.7620 1.4370 -0.1590 C 0 0 1 0 0 0 0 0 0 0 0 0

1.3850 0.1850 0.4610 C 0 0 2 0 0 0 0 0 0 0 0 0

1.3120 -2.2310 0.4400 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.3820 -2.2040 -0.4070 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.7970 0.2320 -0.1930 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.9500 1.4720 1.5470 O 0 0 0 0 0 0 0 0 0 0 0 0

2.7870 0.1650 0.1880 O 0 0 0 0 0 0 0 0 0 0 0 0

0.9710 1.4230 -1.5730 O 0 0 0 0 0 0 0 0 0 0 0 0

0.8900 -1.0720 -1.2170 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9310 -1.0300 1.2320 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2250 0.1950 1.5390 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2650 -2.3100 0.2940 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2350 0.2010 -1.5450 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3360 -2.2570 -0.2590 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1840 2.3500 -0.3080 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.2580 0.9990 -0.5570 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2280 2.3250 0.2680 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5610 2.2360 1.9950 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9020 1.4090 -1.8320 H 0 0 0 0 0 0 0 0 0 0 0 0

3.2670 0.9270 0.5390 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 6 1 0 0 0 0

1 7 1 0 0 0 0

2 3 1 0 0 0 0

2 8 1 0 0 0 0

3 4 1 0 0 0 0

3 9 1 0 0 0 0

4 5 1 0 0 0 0

4 10 1 0 0 0 0

5 6 1 0 0 0 0

5 12 1 0 0 0 0

6 11 1 0 0 0 0

1 13 1 6 0 0 0

2 14 1 1 0 0 0

6 15 1 1 0 0 0

7 16 1 0 0 0 0

3 17 1 6 0 0 0

8 18 1 0 0 0 0

4 19 1 6 0 0 0

9 20 1 0 0 0 0

5 21 1 1 0 0 0

10 22 1 0 0 0 0

12 23 1 0 0 0 0

11 24 1 0 0 0 0

M END): 16 ms

reading 24 atoms

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

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24 atoms created

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Molfile expand

Wikipedia	License
1D-chiro-Inositol or D-chiro-inositol (often abbreviated DCI) is a chemical substance with formula C6H12O6, one of the nine isomers of cyclohexane-1,2,3,4,5,6-hexol (which may be collectively called "inositol"). The molecule has a ring of six carbon atoms, each bound to one hydrogen atom and one hydroxyl (OH) group. The hydroxyls on atoms 1, 2, and 4, in counterclockwise order, lie above the plane of the ring. The molecule being distinct from its mirror image, the compound is chiral, hence its name. Its enantiomer (mirror compound) is 1L-chiro-inositol. Compared to its more common isomer myo-inositol, DCI seems to have relatively minor roles in biochemistry and medicine, mostly connected to the biochemistry of insulin and other hormones.
Read full article at Wikipedia

Formula

C6H12O6

Net Charge

Average Mass

180.156

Monoisotopic Mass

180.06339

InChI

InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m0/s1

InChIKey

CDAISMWEOUEBRE-LKPKBOIGSA-N

SMILES

O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O

Roles Classification
Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	1D-chiro-inositol (CHEBI:27372) has role geroprotector (CHEBI:176497) 1D-chiro-inositol (CHEBI:27372) is a chiro-inositol (CHEBI:23098) 1D-chiro-inositol (CHEBI:27372) is enantiomer of 1L-chiro-inositol (CHEBI:27374)

Incoming	1D-5-O-methyl-chiro-inositol (CHEBI:18173) has functional parent 1D-chiro-inositol (CHEBI:27372) 2D-2,3,5/4,6-pentahydroxycyclohexanone (CHEBI:50920) has functional parent 1D-chiro-inositol (CHEBI:27372) D-pinitol (CHEBI:28548) has functional parent 1D-chiro-inositol (CHEBI:27372) fagopyritol A1 (CHEBI:156276) has functional parent 1D-chiro-inositol (CHEBI:27372) fagopyritol B1 (CHEBI:133330) has functional parent 1D-chiro-inositol (CHEBI:27372) validamine (CHEBI:30449) has functional parent 1D-chiro-inositol (CHEBI:27372) 1L-chiro-inositol (CHEBI:27374) is enantiomer of 1D-chiro-inositol (CHEBI:27372)

IUPAC Name

1D-chiro-inositol

Synonyms	Sources
(+)-chiro-inositol	ChEBI
(+)-Inositol	KEGG COMPOUND
(1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol	IUPAC
1,2,4/3,5,6-cyclohexanehexol	IUPAC
1D-chiro-inositol	UniProt
cis-1,2,4-trans-3,5,6-Cyclohexanehexol	SUBMITTER
D-(+)-chiro-inositol	ChemIDplus
D-chiro-inositol	ChemIDplus
D-inositol	KEGG COMPOUND
DCI	SUBMITTER

Manual Xrefs	Databases
10254647	ChemSpider
1D-chiro-Inositol	Wikipedia
C00053119	KNApSAcK
C19891	KEGG COMPOUND
CBU	PDBeChem
DB15350	DrugBank
FDB001138	FooDB
HMDB0240209	HMDB
View more database links

Registry Number	Type	Source
643-12-9	CAS Registry Number	ChemIDplus

Citations	Types	Sources
18783340	PubMed citation	Europe PMC
22843669	PubMed citation	Europe PMC
25315464	PubMed citation	Europe PMC
31382802	PubMed citation	Europe PMC
33188584	PubMed citation	Europe PMC
33506934	PubMed citation	Europe PMC
33755975	PubMed citation	Europe PMC
33859622	PubMed citation	Europe PMC
34073634	PubMed citation	Europe PMC
34078260	PubMed citation	Europe PMC
34335474	PubMed citation	Europe PMC
37111094	PubMed citation	Europe PMC
38005597	PubMed citation	Europe PMC
38117862	PubMed citation	Europe PMC
38568465	PubMed citation	Europe PMC

Last Modified

28 May 2024

CHEBI:27372 - 1D-chiro-inositol

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