基本情報
- CAS
30220-46-3- 標準SMILES
CC1=C[C@]23C(=O)[C@@H](C=C(CO)[C@@H](O)[C@]2(O)[C@H]1O)[C@H]1[C@@H](C[C@H]3C)C1(C)C- InChIKey
VEBVPUXQAPLADL-POYOOMFHSA-N- 分子式
- C20H28O5
- 平均分子量
- 348.4 g/mol
概要
Ingenol is a tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by methyl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R,5aR,6S,8aS,9R,10aR diastereomer). It is a cyclic terpene ketone and a tetracyclic diterpenoid.
名称と識別子
- 優先名称
- Ingenol
- IUPAC
- (1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
- 現地名
- インゲノール
- 英語名
- Ingenol
- 分子式
- C20H28O5
- 分子量
- 348.43
名称と別名
ingenol30220-46-3IC77UZI9G8(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-oneCHEBI:5922(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-11-ONE, 1A,2,5,5A,6,9,10,10A-OCTAHYDRO-5,5A,6-TRIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-, (1AR,2S,5R,5AR,6S,8AS,9R,10AR)-(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta(a)cyclopropa(e)(10)annulen-11-one(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo(7.5.1.01,5.010,12)pentadeca-2,7-dien-15-oneRefChem:1482871a alpha,2 alpha,5 beta,5a beta,6 beta,beta,9 alpha, 10,10a alpha-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8a alpha-methano cyclopenta(a)cyclopropa(e)cyclodecen-11-one636-889-2
物性
構造計算による物性
- XLogP
- 0.2
- 極性表面積
- 98 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 5
- 回転可能結合数
- 1
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 707
物理化学的性質
- 融点
- 153 °C · 153 °C
- 沸点
- 523.8 · 523.8±50.0 °C(Predicted)
- 比重(密度)
- 1.33 · 1.33±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- 溶解性
- DMSO：可溶
- 外見
- 映画
- 酸解離定数(Pka)
- 12.06 · 12.06±0.70(Predicted)
- 色
- 無色
- InChIKey
- VEBVPUXQAPLADL-POYOOMFHSA-N
- SMILES
- [C@@]12(O)[C@@H](O)C(C)=C[C@@]31C(=O)[C@@]([H])(C=C(CO)[C@H]2O)[C@]1([H])C(C)(C)[C@]1([H])C[C@H]3C
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P354+P338, P317, P321, P332+P317, and P362+P364 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
安全データ
- wgk
- 3
- hs_code
- 2914409000
- risk_code
- 38-41
- hazard_code
- Xi
- safety_code
- 26-36
化学と産業
応用分野
説明Ingenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus. It is a protein kinase C activator that displays a Ki value of 30 μM and an ED50 value of 27 μM in vitro. Most ingenol esters are tumor-promoting. However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis.
使用Ingenol, is the analogue of Ingenol 3-Angelate (I655800), which has anti-tumor activity when used topically for the treatment of actinic keratosis.
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