Cyclomorusin
Completing data — refresh the page later to see the latest
Basic information
- CAS
62596-34-3- Standard SMILES
CC(C)=CC1Oc2cc(O)ccc2-c2oc3c4c(cc(O)c3c(=O)c21)OC(C)(C)C=C4- InChIKey
GDQXJMLXEYSICD-UHFFFAOYSA-N- Molecular formula
- C25H22O6
- Average molar mass
- 418.4 g/mol
- Monoisotopic mass
- 418.14163842
Overview
Cyclomorusin A is an extended flavonoid that is cyclomulberrin in which the hydroxy group at position 10 has undergone oxidative cyclisation to position 3 of the 3-methylbut-2-en-1-yl substituent, with migration of the double bond into conjugation with the aromatic ring. It is a moderate inhibitor of acetylcholinesterase (IC50 = 16.2 - 36.6 M), and a strong inhibitor of platelet-activating factor (PAF; 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine) induced platelet aggregation. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a platelet aggregation inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor and a plant metabolite. It is a polyphenol, an organic heteropentacyclic compound, a cyclic ketone and an extended flavonoid. It is functionally related to a cyclomulberrin.
Names & identifiers
- Preferred name
- Cyclomorusin
- IUPAC
- 11,19-dihydroxy-7,7-dimethyl-15-(2-methylprop-1-enyl)-2,8,16-trioxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one
- English name
- Cyclomulberrochromene
- Molecular formula
- C25H22O6
- Molecular weight
- 418.44
Names & synonyms
Cyclomorusin62596-34-3CyclomulberrochromeneCyclomorusin A11,19-dihydroxy-7,7-dimethyl-15-(2-methylprop-1-enyl)-2,8,16-trioxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-oneCHEBI:1328686,11-dihydroxy-3,3-dimethyl-8-(2-methylprop-1-en-1-yl)-3H,7H,8H-chromeno[4,3-b]pyrano[2,3-h]chromen-7-one6,11-Dihydroxy-3,3-dimethyl-8-(2-methyl-1-propenyl)-3H,7H,8H-bis[1]benzopyrano[4,3-b:6',5'-e]pyran-7-one6,11-Dihydroxy-3,3-dimethyl-8-(2-methyl-1-propenyl)-3H,7H,8H-bis[1]benzopyrano[4,3-b:6',5'-e]pyran-7-one, 9CI6,11-Dihydroxy-3,3-dimethyl-8-(2-methyl-propenyl)-3H,8H-bis(1)benzopyrano(4,3-b:6',5'-e)pyran-7-one11,19-dihydroxy-7,7-dimethyl-15-(2-methylprop-1-enyl)-2,8,16-trioxapentacyclo(12.8.0.03,12.04,9.017,22)docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one6,11-Dihydroxy-3,3-dimethyl-8-(2-methyl-1-propenyl)-3H,7H,8H-bis(1)benzopyrano(4,3-b:6',5'-e)pyran-7-one
Show more names
3H,7H,8H-Bis[1]benzopyrano[4,3-b:6',5'-e]pyran-7-one, 6,11-dihydroxy-3,3-dimethyl-8-(2-methylpropen-1-yl)-
Properties
Computed structural propertiesFilling in
- XLogP
- 5.2
- Topological polar surface area
- 85.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 850
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Melting Point256 - 257 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 233 · 233-234 °C
- Boiling point
- 659.9 · 659.9±55.0 °C(Predicted)
- Density
- 1.42 · 1.42±0.1 g/cm3(Predicted)
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- powder
- pka
- 6.96 · 6.96±0.60(Predicted)
- color
- Yellow
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesCyclomorusin (Cyclomorusin A; Cyclomulberrochromene) is a prenylflavonoid with antiplatelet activity. Cyclomorusin also inhibits markedly collagen-induced platelet aggregation[1].
Additional notes
DefinitionChEBI: An extended flavonoid that is cyclomulberrin in which the hydroxy group at position 10 has undergone oxidative cyclisation to position 3 of the 3-methylbut-2-en-1-yl substituent, with migration of the double bond into conjugation with the aromatic ring. It is a moderate inhibitor of acetylcholinesterase (IC50 = 16.2 - 36.6 muM), and a strong inhibitor of platelet-activating factor (PAF; 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine) induce platelet aggregation.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…