Bergamottin

HCID 5471349

기본 정보

CAS
482-46-2
표준 SMILES
CC(C)=CCC/C(C)=C/COc1c2ccoc2cc2oc(=O)ccc12
InChIKey
DBMJZOMNXBSRED-OQLLNIDSSA-N
분자식
C21H22O4
평균 분자량
338.4 g/mol
단동위원소 질량
338.15180918

개요

Bergomottin is a furanocoumarin. It has a role as a metabolite.

이름 및 식별자

우선 이름
Bergamottin
IUPAC
4-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one

이름 및 동의어

Bergamottin7380-40-7BergamotineBergaptin5-GeranoxypsoralenBergamotin4-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-oneJMU611YFRBDTXSID508975284-{[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one7H-furo(3,2-g)(1)benzopyran-7-one, 4-(((2E)-3,7-dimethyl-2,6-octadien-1-yl)oxy)-4-((2E)-3,7-dimethylocta-2,6-dienoxy)furo(3,2-g)chromen-7-one
이름 더 보기
4-(((2E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-7H-furo(3,2-g)chromen-7-one7H-Furo[3,2-g][1]benzopyran-7-one, 4-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-RefChem:297175-(((2Z)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-2H-furo(3,2-g)chromen-2-oneDTXCID601326883866-344-65-GeranyloxypsoralenBergomottin

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
5.6
극성 표면적
48.7 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
6
무거운 원자 수
25

실험 및 물리화학적 성질

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Other Flavonoids [PK1216]
SpringerMaterials PropertiesChemical shift

안전 및 규제

GHS 분류

GHS Classification · 6건

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

유해성 정보

Hazard Classes and Categories · 2건

Skin Sens. 1 (97.8%)

Not Classified

독성 정보

Health Effects · 1건

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 · 1건

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 · 1건

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)

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1건

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