6-epi-beta-Verbesinol coumarate



Compound IDCDAMM01164
Common name6-epi-beta-Verbesinol coumarate
IUPAC name(4a-methyl-8-methylidene-2-propan-2-yl-1,2,3,4,5,6,7,8a-octahydronaphthalen-1-yl) 3-(4-hydroxyphenyl)prop-2-enoate
Molecular formulaC24H32O3

Experimental data

Retention time12.25
Adduct[M+K]+
Actual mz407.195
Theoretical mz407.198
Error7.76
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.4181

Identifiers and class information

Inchi keyIIZXOWSEQGPRRJ-KIZDUEJFNA-N
SmilesO=C(OC1C2C(=C)CCCC2(C)CCC1C(C)C)C=CC3=CC=C(O)C=C3
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)6
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)368.515
Computed dipole moment(dipole)3.329
Total solvent accessible surface area (SASA)687.015
Hydrophobic component of SASA (FOSA)421.314
Hydrophilic component of SASA (FISA)70.504
Pie component of the SASA (PISA)195.196
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1264.92
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)2.75
Free energy of solvation of dipole (dip^2/V)0.0087608
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0040028
Globularity descriptor (glob)0.823329
Predicted polarizability in cubic angstroms (QPpolrz)42.479
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.068
Predicted octanol/gas partition coefficient (QPlogPoct)16.704
Predicted water/gas partition coefficient (QPlogPw)6.03
Predicted octanol/water partition coefficient (QPlogPo/w)5.826
Predicted aqueous solubility (QPlogS)-6.818
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.976
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.322
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)2124.75
Predicted brain/blood partition coefficient (QPlogBB)-0.492
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1117.2
Predicted skin permeability, log Kp (QPlogKp)-1.555
PM3 calculated ionization potential (IP(ev))9.099
PM3 calculated electron affinity (EA(eV))0.705
Number of likely metabolic reactions (#metab)3
Prediction of binding to human serum albumin (QPlogKhsa)1.288
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
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)53.066
Number of nitrogen and oxygen atoms (#NandO)3
Number of violations of Lipinski’s rule of five (RuleOfFive)1
Number of violations of Jorgensen’s rule of three (RuleOfThree)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P43681CHRNA4Neuronal acetylcholine receptor; alpha4/beta2T70967SwissTargetPrediction
P36544CHRNA7Neuronal acetylcholine receptor protein alpha-7 subunitT34429SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
Q05586GRIN1Glutamate NMDA receptor; GRIN1/GRIN2BT62276SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P43235CTSKCathepsin KT11388SwissTargetPrediction
P42330AKR1C3Aldo-keto-reductase family 1 member C3T60857SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SEA
P04150NR3C1Glucocorticoid receptorT40016SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P06746POLBDNA polymerase beta (by homology)T06958SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction
P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction
P52732KIF11Kinesin-like protein 1T28484SwissTargetPrediction
P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
Q9P1W9PIM2Serine/threonine-protein kinase PIM2T07279SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
O75874IDH1Isocitrate dehydrogenase [NADP] cytoplasmicT69563SwissTargetPrediction
P41143OPRD1Delta opioid receptorT58992SwissTargetPrediction
O00767SCDAcyl-CoA desaturaseT10897SwissTargetPrediction
Q08499PDE4DPhosphodiesterase 4DT02001SwissTargetPrediction
O75116ROCK2Rho-associated protein kinase 2T06093SwissTargetPrediction
Q13418ILKSerine/threonine-protein kinase ILK-1T13616SwissTargetPrediction
P31749AKT1Serine/threonine-protein kinase AKTT67619SwissTargetPrediction
Q15858SCN9ASodium channel protein type IX alpha subunitT12119SwissTargetPrediction
P49810PSEN2Gamma-secretaseT99204SwissTargetPrediction
P08842STSSteryl-sulfataseT33489SwissTargetPrediction
P49286MTNR1BMelatonin receptor 1BT48268SwissTargetPrediction
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction
P34995PTGER1Prostanoid EP1 receptorT15497SwissTargetPrediction
P25101EDNRAEndothelin receptor ET-AT23499SwissTargetPrediction
P11597CETPCholesteryl ester transfer proteinT15334SwissTargetPrediction
P19793RXRARetinoid X receptor alpha (by homology)T13726SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P21453S1PR1Sphingosine 1-phosphate receptor Edg-1T13852SwissTargetPrediction
O75908SOAT2Acyl coenzyme A:cholesterol acyltransferase 2T14463SwissTargetPrediction
P30536TSPOTranslocator protein (by homology)T75440SwissTargetPrediction
P35557GCKHexokinase type IVT87166SwissTargetPrediction
Q07973CYP24A1Cytochrome P450 24A1T92458SwissTargetPrediction
P22460KCNA5Voltage-gated potassium channel subunit Kv1.5T17569SwissTargetPrediction
Q13464ROCK1Rho-associated protein kinase 1T51282SwissTargetPrediction
Q05513PRKCZProtein kinase C (PKC)T59190SwissTargetPrediction
O76083PDE9APhosphodiesterase 9AT17852SwissTargetPrediction
Q99500S1PR3Sphingosine 1-phosphate receptor Edg-3T11241SwissTargetPrediction
Q01064PDE1BPhosphodiesterase 1BT77613SwissTargetPrediction
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T70967DI0029Aneurysm/dissection[ICD-11: BD50]P43681CHRNA4
T70967DI0191Hypertensive crisis[ICD-11: BA03]P43681CHRNA4
T70967DI0196Hypotension[ICD-11: BA20-BA21]P43681CHRNA4
T34429DI0101Corneal disease[ICD-11: 9A76-9A78]P36544CHRNA7
T34429DI0370Schizophrenia[ICD-11: 6A20]P36544CHRNA7
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
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
T62276DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q05586GRIN1
T62276DI0182HIV-infected patients with tuberculosis[ICD-11: 1B10-1B14]Q05586GRIN1
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
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
T11388DI0237Low bone mass disorder[ICD-11: FB83]P43235CTSK
T60857DI0145Female pelvic pain[ICD-11: GA34]P42330AKR1C3
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T40016DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P04150NR3C1
T40016DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P04150NR3C1
T40016DI0037Asthma[ICD-11: CA23]P04150NR3C1
T40016DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P04150NR3C1
T40016DI0108Cushing syndrome[ICD-11: 5A70]P04150NR3C1
T40016DI0280Muscular dystrophy[ICD-11: 8C70]P04150NR3C1
T40016DI0314Oesophagitis[ICD-11: DA24]P04150NR3C1
T40016DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P04150NR3C1
T40016DI0366Rheumatoid arthritis[ICD-11: FA20]P04150NR3C1
T40016DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04150NR3C1
T40016DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]P04150NR3C1
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T06958DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06746POLB
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
T28484DI0012Acute myeloid leukaemia[ICD-11: 2A60]P52732KIF11
T28484DI0172Head and neck cancer[ICD-11: 2D42]P52732KIF11
T28484DI0241Lymphoma[ICD-11: 2A80-2A86]P52732KIF11
T28484DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P52732KIF11
T28484DI0274Multiple myeloma[ICD-11: 2A83]P52732KIF11
T28484DI0321Ovarian cancer[ICD-11: 2C73]P52732KIF11
T28484DI0361Renal cell carcinoma[ICD-11: 2C90]P52732KIF11
T28484DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P52732KIF11
T50594DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11309PIM1
T50594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11309PIM1
T07279DI0274Multiple myeloma[ICD-11: 2A83]Q9P1W9PIM2
T07279DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9P1W9PIM2
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T69563DI0012Acute myeloid leukaemia[ICD-11: 2A60]O75874IDH1
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
T10897DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O00767SCD
T02001DI0411Tonus and reflex abnormality[ICD-11: MB47]Q08499PDE4D
T06093DI0168Graft-versus-host disease[ICD-11: 4B24]O75116ROCK2
T13616DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q13418ILK
T67619DI0062Breast cancer[ICD-11: 2C60-2C6Y]P31749AKT1
T12119DI0051Bipolar disorder[ICD-11: 6A60]Q15858SCN9A
T12119DI0087Chronic pain[ICD-11: MG30]Q15858SCN9A
T12119DI0140Extremities vasodilatation[ICD-11: EG00]Q15858SCN9A
T12119DI0163General pain disorder[ICD-11: 8E43]Q15858SCN9A
T12119DI0320Osteoarthritis[ICD-11: FA00-FA05]Q15858SCN9A
T12119DI0324Pain[ICD-11: MG30-MG3Z]Q15858SCN9A
T12119DI0358Radiculopathy[ICD-11: 8B93]Q15858SCN9A
T12119DI0415Trigeminal nerve disorder[ICD-11: 8B82]Q15858SCN9A
T99204DI0320Osteoarthritis[ICD-11: FA00-FA05]P49810PSEN2
T99204DI0380Shoulder lesion[ICD-11: FB53]P49810PSEN2
T99204DI0390Soft tissue disorder[ICD-11: FB56]P49810PSEN2
T33489DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P08842STS
T48268DI0214Insomnia[ICD-11: 7A00-7A0Z]P49286MTNR1B
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T15497DI0405Thrombosis[ICD-11: DB61-GB90]P34995PTGER1
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T15334DI0035Arterial occlusive disease[ICD-11: BD40]P11597CETP
T15334DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P11597CETP
T15334DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P11597CETP
T15334DI0287Myocardial infarction[ICD-11: BA41-BA43]P11597CETP
T13726DI0225Kaposi sarcoma[ICD-11: 2B57]P19793RXRA
T13726DI0283Mycosis fungoides[ICD-11: 2B01]P19793RXRA
T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
T13852DI0275Multiple sclerosis[ICD-11: 8A40]P21453S1PR1
T13852DI0419Ulcerative colitis[ICD-11: DD71]P21453S1PR1
T14463DI0017Adrenal cancer[ICD-11: 2D11]O75908SOAT2
T75440DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P30536TSPO
T75440DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P30536TSPO
T75440DI0214Insomnia[ICD-11: 7A00-7A0Z]P30536TSPO
T75440DI0216Intentional self-harm[ICD-11: PC91]P30536TSPO
T75440DI0271Mood/affect symptom[ICD-11: MB24]P30536TSPO
T75440DI0411Tonus and reflex abnormality[ICD-11: MB47]P30536TSPO
T87166DI0009Acute diabete complication[ICD-11: 5A2Y]P35557GCK
T87166DI0120Diabetes mellitus[ICD-11: 5A10]P35557GCK
T87166DI0308Obesity[ICD-11: 5B80-5B81]P35557GCK
T87166DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P35557GCK
T92458DI0351Psoriasis[ICD-11: EA90]Q07973CYP24A1
T17569DI0030Angina pectoris[ICD-11: BA40]P22460KCNA5
T51282DI0166Glaucoma[ICD-11: 9C61]Q13464ROCK1
T59190DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q05513PRKCZ
T17852DI0025Alzheimer disease[ICD-11: 8A20]O76083PDE9A
T17852DI0115Dementia[ICD-11: 6D80-6D8Z]O76083PDE9A
T17852DI0165Genitourinary disease[ICD-11: GA0Z-GC8Z]O76083PDE9A
T17852DI0175Heart failure[ICD-11: BD10-BD1Z]O76083PDE9A
T17852DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]O76083PDE9A
T17852DI0331Parkinsonism[ICD-11: 8A00]O76083PDE9A
T17852DI0370Schizophrenia[ICD-11: 6A20]O76083PDE9A
T17852DI0381Sickle-cell disorder[ICD-11: 3A51]O76083PDE9A
T11241DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q99500S1PR3
T77613DI0265Mild neurocognitive disorder[ICD-11: 6D71]Q01064PDE1B

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