Verbenalin

Details

• Internal ID: 20abf33e-1144-4f14-a966-48581f647862
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• 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
• SMILES (Canonical): CC1CC(=O)C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): 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
• 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
• InChI Key: HLXRWTJXGMHOFN-XJSNKYLASA-N
• Popularity: 107 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.13694696 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.94
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• 548-37-8
• Cornin
• Verbenaloside
• Cornin (glycoside)
• Verbenalol, beta-D-glucopyranoside
• Glucopyranoside, verbenalol, beta-D-
• NSC 118055
• CHEBI:9954
• UNII-71B68181Z6
• 71B68181Z6
• cornin iridoid
• 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))-
• NSC118055
• NSC-118055
• 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,4aS,7S,7aR)-
• Verbenalol glucoside
• C17H24O10
• VERBENALIN [MI]
• MLS002473076
• SCHEMBL306538
• Verbenalol b-D-glucopyranoside
• Verbenalin (6CI,7CI,8CI)
• Cornin, >=98% (HPLC)
• CHEMBL1080178
• DTXSID50970143
• HMS2198M18
• HY-N2014
• MFCD00017414
• s9301
• AKOS015920253
• CCG-268497
• LMPR0102070016
• AC-34497
• LS-58152
• 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
• Q-100935
• Q18559312
• Verbenalin, European Pharmacopoeia (EP) Reference Standard
• Methyl (1S,4aS,7S,7aR)-1-(beta-D-glucopyranosyloxy)-7-methyl-5-oxo-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5750	57.50%
Caco-2	-	0.8447	84.47%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6790	67.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7617	76.17%
OATP1B3 inhibitior	+	0.9560	95.60%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8014	80.14%
P-glycoprotein inhibitior	-	0.8190	81.90%
P-glycoprotein substrate	-	0.7778	77.78%
CYP3A4 substrate	+	0.6024	60.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8839	88.39%
CYP3A4 inhibition	-	0.8624	86.24%
CYP2C9 inhibition	-	0.8842	88.42%
CYP2C19 inhibition	-	0.8817	88.17%
CYP2D6 inhibition	-	0.9132	91.32%
CYP1A2 inhibition	-	0.9029	90.29%
CYP2C8 inhibition	-	0.7162	71.62%
CYP inhibitory promiscuity	-	0.8266	82.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6743	67.43%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9538	95.38%
Skin irritation	-	0.7740	77.40%
Skin corrosion	-	0.9551	95.51%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5445	54.45%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8851	88.51%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6476	64.76%
Acute Oral Toxicity (c)	III	0.5022	50.22%
Estrogen receptor binding	+	0.6011	60.11%
Androgen receptor binding	-	0.4938	49.38%
Thyroid receptor binding	-	0.6070	60.70%
Glucocorticoid receptor binding	-	0.6276	62.76%
Aromatase binding	-	0.7367	73.67%
PPAR gamma	-	0.6463	64.63%
Honey bee toxicity	-	0.8417	84.17%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.7220	72.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	199.5 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.94%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.14%	85.14%
CHEMBL2581	P07339	Cathepsin D	91.13%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.01%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.92%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.90%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	84.99%	92.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.31%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.21%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.07%	89.00%

Plants that contains it

• Cornus capitata
• Cornus florida
• Cornus kousa
• Cornus officinalis
• Penstemon grandiflorus
• Penstemon nitidus
• Penstemon secundiflorus
• Symplocos glauca
• Verbena hastata
• Verbena litoralis
• Verbena officinalis
• Verbena officinalis var. officinalis
• Verbena stricta
• Viscum album
• Viscum coloratum

Cross-Links

• PubChem: 73467
• NPASS: NPC106668
• ChEMBL: CHEMBL1080178
• LOTUS: LTS0101316
• wikiData: Q18559312