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Vebenaline
- Family: Plantae - Verbenaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Iridoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@@H](C)CC3=O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| 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 |
| InChIKey | HLXRWTJXGMHOFN-XJSNKYLASA-N |
| Formula | C17H24O10 |
| HBA | 10 |
| HBD | 4 |
| MW | 388.37 |
| Rotatable Bonds | 4 |
| TPSA | 151.98 |
| LogP | -1.94 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.76 |
| Exact Mass | 388.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Verbena officinalis | Verbenaceae | Plantae | 79772 |
Showing of synonyms
Vebenaline
Verbenalin
548-37-8
Verbenaloside
Cornin (glycoside)
Cornin iridoid
Verbenalol, beta-D-glucopyranoside
Glucopyranoside, verbenalol, beta-D-
NSC 118055
UNII-71B68181Z6
VERBENALIN [MI]
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)-
Verbenalin (6CI,7CI,8CI)
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
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)
Cornin
CHEBI:9954
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
C17H24O10
NSC118055
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
Pubchem:
73467
Cas:
548-37-8
Gnps:
CCMSLIB00006470947
Zinc:
ZINC000004098356
Kegg Ligand:
C09802
Chebi:
9954
Chembl:
CHEMBL1080178
No compound-protein relationship available.
SMILES: O=C1CCC(C12)C(OC=C2)OC3CCCCO3
Level: 1
Mol. Weight: 388.37 g/mol
SMILES: O=C1CCC(C12)COC=C2
Level: 0
Mol. Weight: 388.37 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 388.37 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.41
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.950
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.83
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.520
- Plasma Protein Binding
- 54.34
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.940
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.990
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.950
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.540
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -10.400
- Rat (Acute)
- 2.970
- Rat (Chronic Oral)
- 3.370
- Fathead Minnow
- 3.890
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 440.190
- Hydration Free Energy
- -13.150
- Log(D) at pH=7.4
- -0.060
- Log(P)
- -1.31
- Log S
- -1.01
- Log(Vapor Pressure)
- -11.29
- Melting Point
- 165.07
- pKa Acid
- 4.41
- pKa Basic
- 3.8
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7717 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7717 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7663 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7663 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7143 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7143 |
| Periplasmic pH-dependent serine endoprotease DegQ | P39099 | DEGQ_ECOLI | Escherichia coli | 3 | 0.7097 |
| Periplasmic pH-dependent serine endoprotease DegQ | P39099 | DEGQ_ECOLI | Escherichia coli | 3 | 0.7097 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7022 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7022 |