기본 정보
- 표준 SMILES
COc1cc(O)c(CC=C(C)C)c(O)c1C(=O)/C=C/c1ccc(O)cc1- InChIKey
ORXQGKIUCDPEAJ-YRNVUSSQSA-N- 분자식
- C21H22O5
- 평균 분자량
- 354.4 g/mol
- 단동위원소 질량
- 354.1467238
개요
Xanthohumol is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells. It has a role as an antiviral agent, a metabolite, an antineoplastic agent, an EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor, an anti-HIV-1 agent and an apoptosis inducer. It is a member of chalcones, a polyphenol and an aromatic ether. It is a conjugate acid of a xanthohumol(1-).
이름 및 식별자
- 우선 이름
- Xanthohumol
- IUPAC
- (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
- 현지명
- 잔토휴몰
- 영어명
- Xanthohumol
- 분자식
- C21H22O5
- 분자량
- 354.4
이름 및 동의어
Xanthohumol6754-58-1Xantho-flav(E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-oneDTXSID00893171T4467YT1NT(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-oneCHEBI:663311-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one2-Propen-1-one, 1-(2,4-hydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-, (E)-(2E)-1-(2,4-DIHYDROXY-6-METHOXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE(E)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
이름 더 보기
잔토휴몰prop-2-en-1-oneXanthohuMoXanthohumol-RMXantho Flav-PureXanthohumol, >99%Xanthohumol 99.8%Xanthohumol StandardXanthohumol (6CI, 7CI)
XanthoFlav(2E)-1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-oneRefChem:195131DTXCID6013231103'-(3,3-Dimethyl allyl)-2',4',4-trihydroxy-6'-methoxychalcone614-078-4(E/Z)-XanthohumolMFCD00210576
데이터베이스 식별자
- CAS
6754-58-1- PubChem CID
- 639665
- DTXSID
DTXSID00893171- ChEMBL
CHEMBL253896- ChEBI
CHEBI:66331- UNII
- T4467YT1NT
- EC Number
- 614-078-4
- Nikkaji
- J1.438.271B、J17.881K
물성
구조 계산 물성
- XLogP
- 5.1
- 극성 표면적
- 87 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 5
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 26
- 형식 전하
- 0
- 복잡도
- 514
실험 및 물리화학적 성질
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]
Melting Point172 °C
Physical DescriptionSolid
물리화학적 성질
- 녹는점
- 157 · 157-159℃
- 끓는 점
- 576.5 · 576.5±50.0 °C(Predicted)
- 밀도
- 1.244 · 1.244
- 저장 조건
- 2 · 2-8°C
- 용해도
- 10 mg/mL · 에탄올: 용해성10mg/mL
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 7.59 · 7.59±0.45(Predicted)
- 색상
- 노란색
- 생물학적 소스
- plant (Humulus lupulus)
- 안정성
- 2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°C에서 최대 1개월 동안 보관할 수 있습니다.
- 화장품 원료 기능
- 피부 컨디셔닝
- InChI
- InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
- InChIKey
- ORXQGKIUCDPEAJ-YRNVUSSQSA-N
- SMILES
- C(C1=C(OC)C=C(O)C(C/C=C(/C)\C)=C1O)(=O)/C=C/C1=CC=C(O)C=C1
- LogP
- 5.172 · 5.172 (est)
화학적 성질
Xanthohumol is a Light yellow to Brown powder to crystal. It can dissolve in ethanol. This compound is a natural prenylated chalcone isolated from the hop plant, H. lupulus. Xanthohumol and its metabolites induce protective detoxification enzymes, at least in part via the nuclear factor erythroid-2-related factor 2 pathway.
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 4.2% (4 of 96) of reports.
Warning
H317 (95.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 96 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Hazard Classes and CategoriesSkin Sens. 1 (95.8%)
안전 데이터
- wgk
- 3
- rtecs
- UD5574117
- ridadr
- UN 3077 9/PG 3
- HS 번호
- 29145090
- risk_code
- 50/53-43
- hazard_code
- N,Xi
- safety_code
- 60-61-45-22
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents and endogenous substances that antagonize or inhibit the development of new blood vessels.
Cellular LocationsMembrane
응용 분야
개요Xanthohumol(XH, 6754-58-1) binds to the N-terminal domain of valosin-containing protein (VCP), an essential protein for autophagosome maturation. Xanthohumol inhibits the function of VCP thereby impairing autophagosome maturation and resulting in accumulation of the microtubule-associated protein 1 light chain 3-II (LC3-II) Impairs prostate cancer cell growth and proliferation Cell permeable.
용도Xanthohumol from hop (Humulus lupulus) has been used:to treat glioblastoma cells to test its effect on inducing apoptosisto test its protective effect in renal ischemia/reperfusion (I/R) injuryas a component of Dulbecco′s modified Eagle medium (DMEM) to test its antiviral activity in Huh7.5 cells infected with hepatitis C virus cell culture (HCVcc) system
일반 설명Xanthohumol (XN), a prenylated chalcone present in Hop (Humulus lupulus), has been found to possess prominent activities against aging, diabetes, inflammation, microbial infection, and cancer.
공급사50 곳
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추가 설명
정의ChEBI: Xanthohumol is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells. It has a role as a metabolite, an apoptosis inducer, an antineoplastic agent, an antiviral agent, an EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor and an anti-HIV-1 agent. It is a member of chalcones, a polyphenol and an aromatic ether. It is a conjugate acid of a xanthohumol(1-).
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