基本情報
- CAS
482-46-2- 標準SMILES
CC(C)=CCC/C(C)=C/COc1c2ccoc2cc2oc(=O)ccc12- InChIKey
DBMJZOMNXBSRED-OQLLNIDSSA-N- 分子式
- C21H22O4
- 平均分子量
- 338.4 g/mol
- 単同位体質量
- 338.15180918
概要
Bergomottin is a furanocoumarin. It has a role as a metabolite.
名称と識別子
- 優先名称
- Bergamottin
- IUPAC
- 4-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one
名称と別名
名称をさらに表示
データベース識別子
- CAS
482-46-2、7380-40-7- PubChem CID
- 5471349
- DTXSID
DTXSID50897528- ChEMBL
CHEMBL1078442- ChEBI
CHEBI:70476- UNII
- JMU611YFRB
- EC Number
- 639-137-1、866-344-6
- Nikkaji
- J15.428H
物性
構造計算による物性
- XLogP
- 5.6
- 極性表面積
- 48.7 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 4
- 回転可能結合数
- 6
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 570
実験および物理化学的性質
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 2.2% (2 of 92) of reports.
Warning
H317 (97.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 92 reports by companies from 2 notifications to the ECHA C&L Inventory.
Not Classified
危険有害性情報
Hazard Classes and Categories
Skin Sens. 1 (97.8%)
Not Classified
毒性情報
Health Effects
The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (A15105). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions. (L2157) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs.
Toxicity Summary
Bergamottin is a potent chemopreventive agent against aflatoxin B1-inducible cyotoxicity in H4IIE cells with a bifunctional effects on glutathione S-transferase and CYP1A. Potent inhibitor and inactivator of cytochrome P450 1A1-mediated monooxygenase in both murine hepatic microsomes and in a reconstituted system using purified human P450 1A1 (L579). The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. (L579)
Carcinogen Classification
Not listed by IARC. IARC has assessed other furocoumarins, classifying 8-methoxypsoralen as carcinogenic to humans (Group 1), 5-methoxypsoralen as possibly carcinogenic to humans (Group 2A), and certain other furocoumarins as not being classifiable as to their carcinogenicity to humans (Group 3). (L135)
関連反応
化合物ノート
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