Diosgenin

HCID 99474CAS 512-04-9

基本情報

標準SMILES: C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C
InChIKey: WQLVFSAGQJTQCK-VKROHFNGSA-N
分子式: C27H42O3
平均分子量: 414.6 g/mol
単同位体質量: 414.3133952

概要

Diosgenin is a sapogenin that is spirostan which is substituted by a hydroxy group at the 3beta position, contains a double bond at the 5-6 position, and has R- configuration at position 25. A natural product found in Dioscorea (wild yam) species, it is used as the starting point for the commercial synthesis of a number of steroids, including cortisone, pregnenolone and progesterone. It has a role as an antiviral agent, a metabolite, an antineoplastic agent and an apoptosis inducer. It is a sapogenin, a 3beta-sterol, a hexacyclic triterpenoid and a spiroketal. It derives from a hydride of a spirostan.

名称と識別子

優先名称: Diosgenin
IUPAC: (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-ol

名称と別名

DIOSGENIN512-04-9Nitogenin(3beta,25R)-spirost-5-en-3-olK49P2K8WLXCHEBI:4629DTXSID00895074(25R)-spirost-5-en-3beta-diolSpirost-5-en-3-ol, (3beta,25R)-NSC-33396(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icos-18-ene-6,2'-oxane)-16-ol(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-ol

名称をさらに表示

RefChem:5766DTXCID301324626208-134-3DiosgenineMFCD00016887DISOGENIN(25R)-Spirost-5-en-3beta-ol(2'R,4S,5'R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5',6a,8a,9-Tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-ol

データベース識別子

CAS: 512-04-9
PubChem CID: 99474
DTXSID: DTXSID00895074
ChEMBL: CHEMBL412437
ChEBI: CHEBI:4629
UNII: K49P2K8WLX
EC Number: 208-134-3
Nikkaji: J6.272C

物性

構造計算による物性

XLogP: 5.7
極性表面積: 38.7 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 0
重原子数: 30
形式電荷: 0
複雑度: 746

実験および物理化学的性質

LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Spirostanols and derivatives [ST0108]

SpringerMaterials PropertiesCrystal structure

Endocrine DisruptorsPotential endocrine disrupting compound

Collision Cross Section · 2 件

200.92 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

208.4 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 42.9% (3 of 7) of reports.

Warning

H315 (28.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 7 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.