Calcitroic acid

Calcitroic acid
Names

IUPAC name (3R)-3-[(1R,3aR,4E,7aR)- 4-[(2Z)-2-[(3R,5R)-3,5- Dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoic acid
Identifiers
CAS Number	71204-89-2
3D model (Jmol)	Interactive image
ChemSpider	4947800
PubChem	6443842
InChI InChI=1/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7-/t14-,18+,19-,20+,21-,23-/m1/s1 Key: MBLYZRMZFUWLOZ-FEUSBDLHBT
SMILES O=C(O)C[C@@H](C)[C@H]3CC[C@H]2C(=C\C=C1/C(=C)[C@H](O)C[C@@H](O)C1)\CCC[C@@]23C
Properties
Chemical formula	C₂₃H₃₄O₄
Molar mass	374.514
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Calcitroic acid (1α-hydroxy-23-carboxy-24,25,26,27-tetranorvitamin D₃) is a metabolite of 1α,25-dihydroxyvitamin D₃ (calcitriol). Its formation is catalyzed by the enzyme calcitriol 24-hydroxylase.^[1] Calcitroic acid is soluble in water and excreted in bile.^[2]

References

↑ Sakaki T, Kagawa N, Yamamoto K, Inouye K (January 2005). "Metabolism of vitamin D₃ by cytochromes P450". Front. Biosci. 10: 119–34. doi:10.2741/1514. PMID 15574355.
↑ Ross AC, Caballero B, Cousins RJ, Tucker KL, Ziegler TR. Modern nutrition in health and disease. 11. ed, Baltimore: Lippincott Williams & Wilkins 2014.

A	α-Carotene β-Carotene Retinol^# Tretinoin

D	D₂ Ergosterol Ergocalciferol^# D₃ 7-Dehydrocholesterol Previtamin D₃ Cholecalciferol 25-hydroxycholecalciferol Calcitriol (1,25-dihydroxycholecalciferol) Calcitroic acid D₄ Dihydroergocalciferol D₅ D analogues Alfacalcidol Dihydrotachysterol Calcipotriol Tacalcitol Paricalcitol

E	Tocopherol Alpha Beta Gamma Delta Tocotrienol Alpha Beta Gamma Delta Tocofersolan

K	Naphthoquinone Phylloquinone (K₁) Menaquinones (K₂) Menadione (K₃)‡ Menadiol (K₄)

B	B₁ Thiamine^# B₁ analogues Acefurtiamine Allithiamine Benfotiamine Fursultiamine Octotiamine Prosultiamine Sulbutiamine B₂ Riboflavin^# B₃ Niacin Nicotinamide^# B₅ Pantothenic acid Dexpanthenol Pantethine B₆ Pyridoxine^#, Pyridoxal phosphate Pyridoxamine Pyritinol B₇ Biotin B₉ Folic acid Dihydrofolic acid Folinic acid Levomefolic acid B₁₂ Adenosylcobalamin Cyanocobalamin Hydroxocobalamin Methylcobalamin Choline

C	Ascorbic acid^# Dehydroascorbic acid

Combinations

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