Verbenalin



Compound IDCDAMM00419
Common nameVerbenalin
IUPAC namemethyl (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
Molecular formulaC17H24O10

Experimental data

Retention time5.85
Adduct[M+H]+
Actual mz389.141
Theoretical mz389.144
Error9.56
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.48

Identifiers and class information

Inchi keyHLXRWTJXGMHOFN-FGBKZHRTNA-N
SmilesC[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
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)0
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)8
Number of reactive functional groups (#rtvFG)4
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)388.371
Computed dipole moment(dipole)6.78
Total solvent accessible surface area (SASA)647.772
Hydrophobic component of SASA (FOSA)352.772
Hydrophilic component of SASA (FISA)256.615
Pie component of the SASA (PISA)38.385
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1158.9
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)15.9
Free energy of solvation of dipole (dip^2/V)0.0396669
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0490913
Globularity descriptor (glob)0.823707
Predicted polarizability in cubic angstroms (QPpolrz)35.455
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.967
Predicted octanol/gas partition coefficient (QPlogPoct)26.697
Predicted water/gas partition coefficient (QPlogPw)23.04
Predicted octanol/water partition coefficient (QPlogPo/w)-1.641
Predicted aqueous solubility (QPlogS)-2.166
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.382
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.568
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)36.511
Predicted brain/blood partition coefficient (QPlogBB)-2.44
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)13.82
Predicted skin permeability, log Kp (QPlogKp)-5.346
PM3 calculated ionization potential (IP(ev))9.817
PM3 calculated electron affinity (EA(eV))0.101
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-1.22
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)45.304
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)0
Van der Waals surface area (PSA)172.082
Number of nitrogen and oxygen atoms (#NandO)10
Number of violations of Lipinski’s rule of five (RuleOfFive)0
Number of violations of Jorgensen’s rule of three (RuleOfThree)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction and SEA
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction and SEA
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction and SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
Q9BZP6CHIAAcidic mammalian chitinase (by homology)T51597SEA
P24941CDK2Cyclin-dependent kinase 2T70176SwissTargetPrediction
P00813ADAAdenosine deaminaseT03661SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SwissTargetPrediction
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
P25101EDNRAEndothelin receptor ET-AT23499SwissTargetPrediction
P52789HK2Hexokinase type IIT96685SwissTargetPrediction
P11021HSPA578 kDa glucose-regulated proteinT77594SwissTargetPrediction
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction
Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P17931LGALS3Galectin-3T72038SwissTargetPrediction and SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
P20916MAGMyelin-associated glycoprotein (by homology)T95286SEA
O00142TK2Thymidine kinase, mitochondrialT22976SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q15391P2RY14Purinergic receptor P2Y14T16555SEA
Q99417MYCBPMYCBP messenger RNAT37298SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
T70176DI0060Brain cancer[ICD-11: 2A00]P24941CDK2
T70176DI0062Breast cancer[ICD-11: 2C60-2C6Y]P24941CDK2
T70176DI0238Lung cancer[ICD-11: 2C25]P24941CDK2
T70176DI0241Lymphoma[ICD-11: 2A80-2A86]P24941CDK2
T70176DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P24941CDK2
T70176DI0303Non-small-cell lung cancer[ICD-11: 2C25]P24941CDK2
T70176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P24941CDK2
T70176DI0406Thymoma[ICD-11: 2C27]P24941CDK2
T03661DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P00813ADA
T03661DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00813ADA
T03661DI0249Mature B-cell leukaemia[ICD-11: 2A82]P00813ADA
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
T39321DI0279Muscular atrophy[ICD-11: 8B61]P04406GAPDH
T39321DI0280Muscular dystrophy[ICD-11: 8C70]P04406GAPDH
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
T77594DI0252Melanoma[ICD-11: 2C30]P11021HSPA5
T77594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11021HSPA5
T22583DI0009Acute diabete complication[ICD-11: 5A2Y]Q9NY91SLC5A4
T22583DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NY91SLC5A4
T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T95286DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P20916MAG
T22976DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]O00142TK2
T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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