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Helenalin

HCID 23205
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
6754-13-8
표준 SMILES
C=C1C(=O)O[C@@H]2C[C@@H](C)[C@@H]3C=CC(=O)[C@@]3(C)[C@@H](O)[C@H]12
InChIKey
ZVLOPMNVFLSSAA-XEPQRQSNSA-N
분자식
C15H18O4
평균 분자량
262.3 g/mol
단동위원소 질량
262.12050905

개요

Helenalin is a sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer). It has a role as a metabolite, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is an organic heterotricyclic compound, a secondary alcohol, a gamma-lactone, a sesquiterpene lactone and a cyclic ketone.

이름 및 식별자

우선 이름
Helenalin
IUPAC
(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
영어명
HELENALIN
분자식
C15H18O4
분자량
262.3

이름 및 동의어

HELENALIN6754-13-8Helenalin APF 564GUY9L896TNSC-852366alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactoneCHEBI:5635(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dioneDTXSID50217868Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
이름 더 보기
CB1492352HelelinHELENALIN(SH)HELENALIN USP/EP/BPHelenalin (NSC 85236)Helenalin, NF-kappaB inhibitorHelenalin, A. chamissonis ssp. foliosaa-dimethyl-3-methyleneazuleno[6,5-b]-furan-2,5-dione
Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno(6,7-b)furan-2,8-dione(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno(6,7-b)furan-2,8-dioneRefChem:145455DTXCID00140359HSDB 3490NSC85236NSC 85236

물성

구조 계산 물성

XLogP
1.4
극성 표면적
63.6 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
4
회전 가능 결합 수
0
무거운 원자 수
19
형식 전하
0
복잡도
506

실험 및 물리화학적 성질

Chemical ClassesBiological Agents -> Plant Toxins
LogP0.87
TasteBITTER
Color/FormSTERNUTATIVE CRYSTALS FROM BENZENE
SolubilitySLIGHTLY SOL IN WATER; SOL IN ALCOHOL, CHLOROFORM, HOT BENZENE
Melting Point167-168 °C
Optical RotationMAX ABSORPTION: 223 NM (E= 11,900); SPECIFIC OPTICAL ROTATION (C= 3.64 IN 95% ETHANOL): -102.8 DEG @ 25 °C/D
Physical DescriptionSolid; [Merck Index] White solid; [MSDSonline]

물리화학적 성질

녹는점
167 · 167-168°
끓는 점
325.55 °C · 325.55°C (rough estimate)
밀도
1.0772 · 1.0772 (rough estimate)
굴절률
1.43 · 1.4300 (estimate)
저장 조건
-20 ° · -20°

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

유해성 정보

Hazards Summary · 1건

Causes seizures at lethal doses in mice; Intraperitoneal LD50 (mouse) = 10 mg/kg; [RTECS] Especially toxic in flowering stage; may cause paralysis of voluntary and cardiac musculature and fatal gastroenteritis; Emergency treatment: Plants- sesquiterpene lactones; Sesquiterpene lactones are in many plants. They cause toxicity mainly in livestock that eat the plants. Human poisoning cases are extremely rare. Possible symptoms after ingestion include irritation of mucous membranes, dyspnea, pulmonary hemorrhage, tremors, seizures, abdominal pain, and liver injury. [HSDB] Sesquiterpene lactones are a common cause of allergic dermatitis in florists. See Sesquiterpene lactones.

Hazard Classes and CategoriesAcute Tox. 3 (100%)

독성 정보

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Natural Pollution SourcesHELENIUM MICROCEPHALUM (SMALLHEAD SNEEZEWEED) IS...VERY TOXIC, PARTICULARLY IN THE FLOWERING STAGE. THE TOXIC PRINCIPLE IS NOW BELIEVED TO BE A SESQUITERPENE, HELENALIN.
Human Toxicity Excerpts · 2건

INTENSELY POISONOUS, CAPABLE OF CAUSING PARALYSIS OF VOLUNTARY & CARDIAC MUSCULATURE & FATAL GASTROENTERITIS.

HELENIUM MICROCEPHALUM (SMALLHEAD SNEEZEWEED) IS...VERY TOXIC, PARTICULARLY IN THE FLOWERING STAGE. THE TOXIC PRINCIPLE IS NOW BELIEVED TO BE A SESQUITERPENE, HELENALIN.

화학 및 산업

약리 정보

Mechanism of Action · 3건

DOGS TOLERATED RAPID IV INJECTIONS OF 0.3% HELENALIN OR CRUDE 50% ETHANOL EXTRACT OF HELENIUM MICROCEPHALUM AT A MAXIMUM CUMULATIVE DOSE OF 90 MG HELENALIN/KG OR A MAXIMUM OF 10 G PLANT/KG. THE PHARMACODYNAMIC RESPONSES WERE AN INITIAL CHOLINERGIC EFFECT, A NICOTINIC EFFECT, STIMULATION OF THE RESPIRATORY & CENTRAL NERVOUS SYSTEMS, & PROGRESSIVE CARDIAC FAILURE.

THE MODE OF ACTION OF HELENALIN AS A PROTEIN SYNTHESIS INHIBITOR IN P-388 LYMPHOCYTIC LEUKEMIA CELLS WAS INVESTIGATED IN CRUDE LYSATES OF THE CELLS. THERE WAS A 4-MIN LAG AFTER THE ADDITION OF DRUG BEFORE INHIBITION OF PROTEIN SYNTHESIS OCCURRED. BOTH DRUGS ALLOWED RUN-OFF OF PREFORMED POLYSOMES BUT DID INHIBIT THE FORMATION OF 80 S INITIATION COMPLEX, SUGGESTING A PREFERENTIAL INHIBITION OF GREATER THAN OR EQUAL TO INITIATION REACTIONS.

HELENALIN WAS CAPABLE OF ALKYLATING THE THIOL GROUP OF REDUCED GLUTATHIONE & L-CYSTEINE IN VITRO. HELENALIN WAS ACTIVE AGAINST EHRLICH ASCITES & WALDER 256 ASCITES CARCINOSARCOMA IN VIVO & HAD CYTOTOXIC ACTIVITY AGAINST H.EP-2 TUMOR CELLS IN VITRO.

MeSH Pharmacological Classification · 4건

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

용도 및 제조

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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

데이터베이스 식별자

CAS
6754-13-8
PubChem CID
23205
DTXSID
DTXSID50217868
ChEMBL
CHEMBL338474
ChEBI
CHEBI:5635
UNII
4GUY9L896T
EC Number
111-092-8
Nikkaji
J21.229F
용해도
DMSO(최대 20mg/ml) 또는 에탄올(최대 10mg/ml)에 용해됩니다.
물리적 상태
흰색 내지 회백색 고체.
산도 계수 (pKa)
13.29 · 13.29±0.60(Predicted)
색상
하얀색
안정성
2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°에서 최대 1개월 동안 보관할 수 있습니다.
InChI
1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1
InChIKey
ZVLOPMNVFLSSAA-XEPQRQSNSA-N
SMILES
O1[C@H]2[C@H]([C@@H]([C@]3([C@H]([C@@H](C2)C)C=CC3=O)C)O)C(=C)C1=O
LogP
0.87 · 0.870
Non-Human Toxicity Excerpts · 2건

ADMIN OF HELENALIN TO MICE AT 20 MG/KG/DAY LOWERED SERUM CHOLESTEROL BY APPROX 30% & OF SERUM TRIGLYCERIDES BY APPROX 25%.

THE ORAL LD50 OF HELENALIN FOR 5 MAMMALIAN SPECIES (SHEEP, HAMSTERS, RABBITS, RATS, MICE) WAS BETWEEN 85-150 MG/KG.

안전 데이터

wgk
WGK 3
ridadr
2811
독성
LD50 in mice, rats (mg/kg): 150, 125 orally (Witzel)
포장분류
III
위험 등급
6.1(b)
Hazard Classifications
Acute Tox. 3 Oral
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
유해 물질 데이터
6754-13-8(Hazardous Substances Data)
UsesExtremely toxic sesquiterpene lactone found in Helenium microcephalum (smallhead sneezeweed); [HSDB]
Methods of ManufacturingPSEUDOGUAIANOLIDE SESQUITERPENOID LACTONE FROM HELENIUM AUTUMNALE L, H AMARUM (RAF) H ROCH, H MICROCEPHALUM DC, COMPOSITAE. ISOLATION: CLARK, J AM CHEM SOC 58, 1982 (1936); ADAMS, HORZ, J AM CHEM SOC 71, 2546 (1949).
응용 분야 · 1건

용도Helenalin is a highly toxic compound, with hepatic and lymphatic tissues particularly vulnerable to its effects. It is believed to be responsible for the toxicity and skin irritation associated with Arnica. If enough of the plant is ingested, the helenalin produces severe gastroenteritis and internal bleeding of the digestive tract.

공급사30 곳

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