Calcitroic Acid
Basic information
- CAS
71204-89-2- Standard SMILES
C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)CC(=O)O)CC[C@@H]23)C[C@@H](O)C[C@@H]1O- InChIKey
MBLYZRMZFUWLOZ-ZTIKAOTBSA-N- Molecular formula
- C23H34O4
- Average molar mass
- 374.5 g/mol
- Monoisotopic mass
- 374.24570956
Overview
Calcitroic acid is a hydroxycalciol that is calcidiol in which the pro-S hydrogen of calcidiol is replaced by a hydroxy group and the C-23/C-27 unit is replaced by a carboxy group. It is a conjugate acid of a calcitroate.
Names & identifiers
- Preferred name
- Calcitroic Acid
- IUPAC
- (3R)-3-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butanoic acid
- English name
- 1,3-dihydroxy-(1a,3b,5Z,7E)- 24-nor-9,10-secochola-5,7,10(19)-trien-23-oic acid
- Molecular formula
- C23H34O4
- Molecular weight
- 374.51
Names & synonyms
Calcitroic acid71204-89-2F7KIE52YT0CHEBI:478281alpha-Hydroxy-23-carboxytetranorvitamin DDTXSID609040301alpha-hydroxy-24,25,26,27-tetranorvitamin D3 23-carboxylic acid1alpha,3beta-Dihydroxy-24-nor-9,10-seco-5,7,10(19)-cholatrien-23-oic acid(1S,3R,5Z,7E)-1,3-dihydroxy-24-nor-9,10-secochola-5,7,10(19)-trien-23-oic acid24-Nor-9,10-secochola-5,7,10(19)-trien-23-oic acid, 1,3-dihydroxy-, (1alpha,3beta,5Z,7E)-RefChem:917868DTXCID901331952
Show more names
1α-HydroxycalcioiCalcitroic acid (D3)Vitamin D8 Injection(1α,3β,5Z,7E)-1,3-Dihydroxy-24-nor-9,10-secochola-5,7,10(19)-trien-23-oic Acid1,3-dihydroxy-(1a,3b,5Z,7E)- 24-nor-9,10-secochola-5,7,10(19)-trien-23-oic acid(βR,1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-Dihydroxy-2-Methylenecyclohexylidene]ethylidene]octahydro-β,7a-diMethyl-1H-indene-1-propanoic Acid1H-Indene-1-propanoic acid, 4-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene]ethylidene]octahydro-β,7a-dimethyl-, (βR,1R,3aS,4E,7aR)-
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 661
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Secosteroids [ST03] -> Vitamin D3 and derivatives [ST0302]
Physicochemical properties
- Boiling point
- 572.5 · 572.5±50.0 °C(Predicted)
- Density
- 1.15 · 1.15±0.1 g/cm3(Predicted)
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 4.71 · 4.71±0.10(Predicted)
- form
- Solid
- color
- White to Off-White
- Stability
- Light Sensitive
- FDA UNII
- 7 KIE52YT0 · F7KIE52YT0
Chemistry & industry
Applications
UsesCalcitroic Acid is a major metabolite of Calcitriol (C144500).
Additional notes
DefinitionChEBI: A hydroxycalciol that is calcidiol in which the pro-S hydrogen of calcidiol is replaced by a hydroxy group and the C-23/C-27 unit is replaced by a carboxy group.
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