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Verbenalin

PubChem CID: 73467

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Compound Synonyms Verbenalin, 548-37-8, Cornin, Verbenaloside, Cornin (glycoside), cornin iridoid, Verbenalol, beta-D-glucopyranoside, Glucopyranoside, verbenalol, beta-D-, NSC 118055, UNII-71B68181Z6, VERBENALIN [MI], CHEBI:9954, 71B68181Z6, NSC-118055, Cyclopenta(c)pyran-4-carboxylic acid, 1,4a,5,6,7,7a-hexahydro-1-(beta-D-glucopyranosyloxy)-7-methyl-5-oxo-, methyl ester, (1S-(1-alpha,4a-alpha,7-alapha,7a-alpha))-, Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-5-oxo-, methyl ester, (1S-(1alpha,4aalpha,7alpha,7aalpha))-, methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-7-METHYL-5-OXO-, METHYL ESTER, (1S,4AS,7S,7AR)-, C17H24O10, Verbenalin (6CI,7CI,8CI), NSC118055, Cyclopenta[c]pyran-4-carboxylic acid, 1-(.beta.-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-5-oxo-, methyl ester, (1S,4aS,7S,7aR)-, methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta(c)pyran-4-carboxylate, MFCD00017414, Cornin, verbenaloside, Verbenalin (Standard), MLS002473076, SCHEMBL306538, Cornin, >=98% (HPLC), CHEMBL1080178, HY-N2014R, DTXSID50970143, HLXRWTJXGMHOFN-XJSNKYLASA-N, HMS2198M18, HY-N2014, s9301, AKOS015920253, CCG-268497, LMPR0102070016, MV45062, AC-34497, DA-62463, methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate, SMR001397179, CS-0018334, C09802, Q18559312, Verbenalin, European Pharmacopoeia (EP) Reference Standard, CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(BETA-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-7-METHYL-5-OXO-, METHYL ESTER, (1S,4AS,7S,7AR)-, Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-5-oxo-, methyl ester, (1S-(1alpha,4aalpha,7alpha,7aalpha))-(9CI), Methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Ghose Rule False
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 152.0
Hydrogen Bond Donor Count 4.0
Pfizer 3 75 Rule True
Scaffold Graph Level CC1CCC2C(CC3CCCCC3)CCCC12
Np Classifier Class Iridoids monoterpenoids
Deep Smiles OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6[C@@H]C)CC5=O))))))C=O)OC))))))))[C@@H][C@H][C@@H]6O))O))O
Heavy Atom Count 27.0
Classyfire Class Prenol lipids
Description Verbenalin, also known as cornin (glycoside) or cornin iridoid, is a member of the class of compounds known as iridoid o-glycosides. Iridoid o-glycosides are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Thus, verbenalin is considered to be an isoprenoid lipid molecule. Verbenalin is soluble (in water) and a very weakly acidic compound (based on its pKa). Verbenalin is a bitter tasting compound found in common verbena, which makes verbenalin a potential biomarker for the consumption of this food product. Verbenalin is a chemical compound, classified as an iridoid glucoside, that is found in Verbena officinalis. It is one of the sleep-promoting (soporific) components in Verbena officinalis .
Scaffold Graph Node Level OC1CCC2C(OC3CCCCO3)OCCC12
Classyfire Subclass Terpene glycosides
Isotope Atom Count 0.0
Molecular Complexity 619.0
Database Name cmaup_ingredients;fooddb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 9.0
Uniprot Id Q96QE3, P84022
Iupac Name methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
Prediction Hob 0.0
Veber Rule False
Classyfire Superclass Lipids and lipid-like molecules
Xlogp -1.5
Gsk 4 400 Rule True
Molecular Formula C17H24O10
Scaffold Graph Node Bond Level O=C1CCC2C(OC3CCCCO3)OC=CC12
Prediction Swissadme 0.0
Inchi Key HLXRWTJXGMHOFN-XJSNKYLASA-N
Silicos It Class Soluble
Fcsp3 0.7647058823529411
Logs -1.386
Rotatable Bond Count 5.0
Logd -0.497
Synonyms cornin, verbenalin, verbenaloside
Esol Class Very soluble
Functional Groups CC(C)=O, CO, COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1
Compound Name Verbenalin
Prediction Hob Swissadme 0.0
Exact Mass 388.137
Formal Charge 0.0
Monoisotopic Mass 388.137
Hydrogen Bond Acceptor Count 10.0
Molecular Weight 388.4
Gi Absorption False
Covalent Unit Count 1.0
Total Atom Stereocenter Count 9.0
Total Bond Stereocenter Count 0.0
Lipinski Rule Of 5 True
Esol -0.9728878000000005
Inchi InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1
Smiles C[C@H]1CC(=O)[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
Nring 3.0
Np Classifier Biosynthetic Pathway Terpenoids
Defined Bond Stereocenter Count 0.0
Egan Rule False
Np Classifier Superclass Monoterpenoids

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