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Acurea

HCID 3662
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
11079-53-1
Standard SMILES
CC(C)=CCCC1(C)C(CC=C(C)C)CC2(CC=C(C)C)C(=O)C1(C(=O)C(C)C)C(=O)C(CC=C(C)C)=C2O
InChIKey
KGSZHKRKHXOAMG-UHFFFAOYSA-N
Molecular formula
C35H52O4
Average molar mass
536.8 g/mol
Monoisotopic mass
536.38656014

Names & identifiers

Preferred name
Acurea
IUPAC
4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione
English name
HYPERFORIN
Molecular formula
C35H52O4
Molecular weight
536.78

Names & synonyms

AcureaRefChem:1076155tetrahydrohyperforinSCHEMBL8168239KGSZHKRKHXOAMG-UHFFFAOYSA-NDB-050097Q27461275HYPERFORINHYPERFORIN MIXHYPERFORIN MIX(P)HYPERFORIN USP/EP/BPHyperforin (solution in Ethanol)
Show more names
Hyperforin - solution in methanolBicyclo[3.3.1]non-3-ene-2,9-dione, 4-hydroxy-6-Hyperforin dicyclohexylammonium salt, active constituent of St. John#39s wortmethyl-1,3,7-tris(3-methyl-2-buten-1-yl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-penten-1-yl)-,(1R,5S,6R,7S)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione

Database identifiers

CAS
11079-53-1
PubChem CID
3662

Properties

Computed structural properties

XLogP
9.6
Topological polar surface area
71.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
11
Heavy atoms
39
Formal charge
0
Complexity
1,140

Experimental & physicochemical properties

Melting Point79 - 80 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
79 · 79–80 °C (174–176 °F)
alpha
18 · D18 +41° (in ethanol)
Boiling point
616.8 · 616.8±55.0 °C(Predicted)
Density
1.01 · 1.010±0.06 g/cm3 (20 ºC 760 Torr)
Flash point
9.7 °C · 9.7 °C - closed cup
storage temp.
-20 °C · -20°C
form
solution
pka
4.8 · 4.8 (50% aq ethanol)
InChIKey
IWBJJCOKGLUQIZ-HQKKAZOISA-N
SMILES
CC(C)C(=O)[C@@]12C(O)=C(C\C=C(\C)C)C(=O)[C@@](C\C=C(/C)C)(C[C@H](C\C=C(\C)C)[C@@]1(C)CC\C=C(\C)C)C2=O
CAS DataBase Reference
11079 · 11079-53-1
FDA UNII
741 E34FP · RM741E34FP
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
2 · GHS02,GHS06,GHS08
Signal word
Danger
Hazard statements
225 · H225-H301+H311+H331-H370
Precautionary statements
210 · P210-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
target organs
Eyes
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
F,T
Risk Statements
11 · 11-23/24/25-39/23/24/25
Safety Statements
7 · 7-16-36/37-45
RIDADR
1230 · UN1230 - class 3 - PG 2 - Methanol
WGK Germany
3 · 3
HS Code
29144000 · 29144000
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Hazardous Substances Data
11079 · 11079-53-1(Hazardous Substances Data)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
ridadr
UN1230 - class 3 - PG 2 - Methanol
hs_code
29144000
risk_code
11-23/24/25-39/23/24/25
Signal word
Danger
Symbol(GHS)
GHS02,GHS06,GHS08
hazard_code
F,T
safety_code
7-16-36/37-45
Storage Class
3 - Flammable liquids
target organs
Eyes
Hazard statements
H225-H301+H311+H331-H370
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Precautionary statements
P210-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
Hazardous Substances Data
11079-53-1(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular
Applications · 3 items

UsesSt. John’s wort is a widely consumed herbal preparation which has been claimed to have a number of medicinal properties. It contains a number of known lipid signalling mediators, including chlorogenic acid, hypericin, hyperforin, and I3,II8-biapigenin. Hyperforin exhibits two activities which may alter the action of other concurrent medications. It inhibits the activity of several CYP450 enzymes, with CYP2D6 being the most sensitive with an IC50 of about 10 μg/ml. Hyperforin is also a ligand for the steroid X receptor (SXR). Since one activity of this receptor is the induction of CYP450 expression, the exact nature of hyperforin’s drug-drug interactions must be evaluated on a case-by-case basis. However, these interactions certainly complicate its use as a human therapeutic.[Cayman Chemical]

UsesHyperforin may be used:as a reference standard for calibration curve generation in high-perfornamce liquid chromatography (HPLC) analysisto test its cytotoxic effect and apoptosis induction in mouse embryonic cellsas a pregnane X receptor (PXR) in porcine brain capillary endothelial cells for transport assay

General DescriptionHyperforin is a phloroglucinol component of St. John′s wort and a pregnane X receptor ligand.

Suppliers68 total

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
銘瑞集團有限公司17318633522 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
上海纯优生物科技有限公司15921393123 18302135232 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]
河南闰霖化工有限公司+86-18738066252; +86-18738066252 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
上海纽雀客生物科技有限公司13916276291 · [email protected]
成都普睿法药物研发有限公司82633860 18982077548 · [email protected]
湖北丹鼎医药科技有限公司18917019315(微信同号) 17701422019 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
怀化市冰峰化工有限公司0745-2866851 17711757908 · [email protected]
武汉市皇臻生物化工有限公司13795480948 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
Stanford Chemicals Company+1 (949) 468-0555 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
武汉卡诺斯科技有限公司153-37111468 15337111468 · [email protected]
金瓯生物医药(南京)有限公司13000000000 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
上海萄普生物医药技术有限公司15900573766 18018507602 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
武汉福鑫化工有限公司+86-2759207851; +86-18007136271 · [email protected]
风咏生物(AbMole)021-10000000 13000000000 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
湖北阡陌生物科技有限公司0711-3812399 18062309155 · [email protected]
陕西萃程生物医药科技有限公司13186333400 · [email protected]
深圳市创鑫生物科技有限公司13417589054 · [email protected]
湖北鸿鑫瑞宇精细化工有限公司027-65526929 15102793023 · [email protected]
凯立德生物医药技术(上海)有限公司021-58180488 · [email protected]
Mensura Group Limited18780014153 · [email protected]
南京本草益康生物科技有限公司025-69790911 18362932668 · [email protected]
济南药研药物化学有限公司[email protected]
career henan chemical co+86-0371-86658258 · [email protected]
郑州艾克姆化工有限公司037163312495 13303845143 · [email protected]
北京沃凯生物科技有限公司010-62971590 18548936886 · [email protected]
湖北鸿鑫瑞宇精细化工有限公司027-65385071 17771822910 · [email protected]
成都普瑞法科技开发有限公司+86-28-82633860; +86-18080483897 · [email protected]

Additional notes

DefinitionChEBI: A cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum.

Related reactions

2 records
New reaction record
HRID 1097123 reaction equation
HRID 1097123As productuspto-grants-2012_03
HRID 2213938 reaction equation
HRID 2213938As productuspto-grants-2006_09

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes