(R)-3,4-Dihydro-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol



Compound IDCDAMM01566
Common name(R)-3,4-Dihydro-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol
IUPAC name2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydro-2H-chromen-6-ol
Molecular formulaC25H36O2

Experimental data

Retention time12.94
Adduct[M+H]+
Actual mz369.274
Theoretical mz369.279
Error13.2
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7215

Identifiers and class information

Inchi keyWSTGHGHPTQPFAP-YARIIHNNNA-N
SmilesOC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)CCC2=C1
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Pharmacokinetic properties

Number of descriptor values(#stars)7
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)10
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)368.558
Computed dipole moment(dipole)0.998
Total solvent accessible surface area (SASA)758.024
Hydrophobic component of SASA (FOSA)559.674
Hydrophilic component of SASA (FISA)54.691
Pie component of the SASA (PISA)143.659
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1376.96
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)1.5
Free energy of solvation of dipole (dip^2/V)0.0007232
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0019788
Globularity descriptor (glob)0.78964
Predicted polarizability in cubic angstroms (QPpolrz)43.903
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.721
Predicted octanol/gas partition coefficient (QPlogPoct)16.01
Predicted water/gas partition coefficient (QPlogPw)3.629
Predicted octanol/water partition coefficient (QPlogPo/w)7.125
Predicted aqueous solubility (QPlogS)-7.965
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.503
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.621
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)3001.02
Predicted brain/blood partition coefficient (QPlogBB)-0.624
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1622.63
Predicted skin permeability, log Kp (QPlogKp)-1.061
PM3 calculated ionization potential (IP(ev))8.7
PM3 calculated electron affinity (EA(eV))-0.191
Number of likely metabolic reactions (#metab)11
Prediction of binding to human serum albumin (QPlogKhsa)1.69
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)30.28
Number of nitrogen and oxygen atoms (#NandO)2
Number of violations of Lipinski’s rule of five (RuleOfFive)1
Number of violations of Jorgensen’s rule of three (RuleOfThree)2

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P12821ACEAngiotensin-converting enzymeT98311SwissTargetPrediction
P06239LCKTyrosine-protein kinase LCKT12499SwissTargetPrediction
P48449LSSLanosterol synthaseT56175SEA
P21554CNR1Cannabinoid receptor 1 (by homology)T76685SwissTargetPrediction
Q05586GRIN1Glutamate NMDA receptor; GRIN1/GRIN2BT62276SwissTargetPrediction
P43235CTSKCathepsin KT11388SwissTargetPrediction
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
P35968KDRVascular endothelial growth factor receptor 2T80975SwissTargetPrediction
O00519FAAHAnandamide amidohydrolaseT11754SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction
P14174MIFMacrophage migration inhibitory factorT39977SwissTargetPrediction
P17655CAPN2Calpain 2T86837SwissTargetPrediction
Q14534SQLESqualene monooxygenase (by homology)T93344SEA
P21918DRD5Dopamine D5 receptorT46828SEA
P52732KIF11Kinesin-like protein 1T28484SwissTargetPrediction
Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
P49327FASNFatty acid synthaseT16514SwissTargetPrediction
P37288AVPR1AVasopressin V1a receptor (by homology)T79232SwissTargetPrediction
P62942FKBP1AFK506-binding protein 1AT76059SwissTargetPrediction
O75116ROCK2Rho-associated protein kinase 2T06093SwissTargetPrediction
Q13418ILKSerine/threonine-protein kinase ILK-1T13616SwissTargetPrediction
P31749AKT1Serine/threonine-protein kinase AKTT67619SwissTargetPrediction
P53779MAPK10c-Jun N-terminal kinase 3T85421SwissTargetPrediction
P25774CTSSCathepsin ST68290SwissTargetPrediction
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction
P09619PDGFRBPlatelet-derived growth factor receptor betaT59102SwissTargetPrediction
P23415GLRA1Glycine receptor subunit alpha-1T50269SwissTargetPrediction
P34998CRHR1Corticotropin releasing factor receptor 1 (by homology)T45262SwissTargetPrediction
O43174CYP26A1Cytochrome P450 26A1T84634SwissTargetPrediction
Q00987MDM2p53-binding protein Mdm-2T00176SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P04049RAF1Serine/threonine-protein kinase RAFT51883SwissTargetPrediction
P15056BRAFSerine/threonine-protein kinase B-rafT99089SwissTargetPrediction
O60760HPGDSHematopoietic prostaglandin D synthaseT19433SwissTargetPrediction
P25116F2RProteinase-activated receptor 1T36483SwissTargetPrediction
P22460KCNA5Voltage-gated potassium channel subunit Kv1.5T17569SwissTargetPrediction
O00408PDE2APhosphodiesterase 2AT77400SwissTargetPrediction
P01130LDLRLDL receptorT94692SwissTargetPrediction
P29371TACR3Neurokinin 3 receptorT29683SwissTargetPrediction
Q13464ROCK1Rho-associated protein kinase 1T51282SwissTargetPrediction
Q15759MAPK11MAP kinase p38 betaT55729SwissTargetPrediction
Q14330GPR18N-arachidonyl glycine receptorT72267SwissTargetPrediction
O95749GGPS1GeranyltranstransferaseT86528SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T98311DI0175Heart failure[ICD-11: BD10-BD1Z]P12821ACE
T98311DI0190Hypertension[ICD-11: BA00-BA04]P12821ACE
T12499DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P06239LCK
T56175DI0035Arterial occlusive disease[ICD-11: BD40]P48449LSS
T76685DI0031Anorexia nervosa[ICD-11: 6B80]P21554CNR1
T76685DI0214Insomnia[ICD-11: 7A00-7A0Z]P21554CNR1
T76685DI0308Obesity[ICD-11: 5B80-5B81]P21554CNR1
T62276DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q05586GRIN1
T62276DI0182HIV-infected patients with tuberculosis[ICD-11: 1B10-1B14]Q05586GRIN1
T11388DI0237Low bone mass disorder[ICD-11: FB83]P43235CTSK
T66665DI0087Chronic pain[ICD-11: MG30]P35354PTGS2
T66665DI0145Female pelvic pain[ICD-11: GA34]P35354PTGS2
T66665DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P35354PTGS2
T66665DI0207Indeterminate colitis[ICD-11: DD72]P35354PTGS2
T66665DI0227Knee osteoarthritis[ICD-11: FA01]P35354PTGS2
T66665DI0320Osteoarthritis[ICD-11: FA00-FA05]P35354PTGS2
T66665DI0324Pain[ICD-11: MG30-MG3Z]P35354PTGS2
T66665DI0366Rheumatoid arthritis[ICD-11: FA20]P35354PTGS2
T66665DI0416Tuberculosis[ICD-11: 1B10-1B12]P35354PTGS2
T80896DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q92731ESR2
T80896DI0108Cushing syndrome[ICD-11: 5A70]Q92731ESR2
T80896DI0254Menopausal disorder[ICD-11: GA30]Q92731ESR2
T80896DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q92731ESR2
T80975DI0062Breast cancer[ICD-11: 2C60-2C6Y]P35968KDR
T80975DI0095Colorectal cancer[ICD-11: 2B91]P35968KDR
T80975DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P35968KDR
T80975DI0244Malignant digestive organ neoplasm[ICD-11: 2C11]P35968KDR
T80975DI0361Renal cell carcinoma[ICD-11: 2C90]P35968KDR
T80975DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35968KDR
T80975DI0395Stomach cancer[ICD-11: 2B72]P35968KDR
T80975DI0403Thrombocytopenia[ICD-11: 3B64]P35968KDR
T80975DI0407Thyroid cancer[ICD-11: 2D10]P35968KDR
T11754DI0101Corneal disease[ICD-11: 9A76-9A78]O00519FAAH
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
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T39977DI0403Thrombocytopenia[ICD-11: 3B64]P14174MIF
T86837DI0106COVID-19[ICD-11: 1D6Y]P17655CAPN2
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T46828DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21918DRD5
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
T65864DI0102Coronary atherosclerosis[ICD-11: BA52]Q16539MAPK14
T65864DI0287Myocardial infarction[ICD-11: BA41-BA43]Q16539MAPK14
T65864DI0366Rheumatoid arthritis[ICD-11: FA20]Q16539MAPK14
T65864DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]Q16539MAPK14
T16514DI0096concerning food/fluid intake symptom[ICD-11: MG43]P49327FASN
T79232DI0009Acute diabete complication[ICD-11: 5A2Y]P37288AVPR1A
T79232DI0041Autism spectrum disorder[ICD-11: 6A02]P37288AVPR1A
T79232DI0190Hypertension[ICD-11: BA00-BA04]P37288AVPR1A
T79232DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P37288AVPR1A
T79232DI0236Localisation[ICD-11: N.A.]P37288AVPR1A
T76059DI0331Parkinsonism[ICD-11: 8A00]P62942FKBP1A
T76059DI0349Pruritus[ICD-11: EC90]P62942FKBP1A
T76059DI0413Transplant rejection[ICD-11: NE84]P62942FKBP1A
T06093DI0168Graft-versus-host disease[ICD-11: 4B24]O75116ROCK2
T13616DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q13418ILK
T67619DI0062Breast cancer[ICD-11: 2C60-2C6Y]P31749AKT1
T85421DI0125Dissociative neurological symptom disorder[ICD-11: 6B60]P53779MAPK10
T68290DI0042Autoimmune disease[ICD-11: 4A40-4A45]P25774CTSS
T68290DI0092Coeliac disease[ICD-11: DA95]P25774CTSS
T68290DI0107Crohn disease[ICD-11: DD70]P25774CTSS
T68290DI0120Diabetes mellitus[ICD-11: 5A10]P25774CTSS
T68290DI0163General pain disorder[ICD-11: 8E43]P25774CTSS
T68290DI0324Pain[ICD-11: MG30-MG3Z]P25774CTSS
T68290DI0382Sjogren syndrome[ICD-11: 4A43]P25774CTSS
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T59102DI0009Acute diabete complication[ICD-11: 5A2Y]P09619PDGFRB
T59102DI0361Renal cell carcinoma[ICD-11: 2C90]P09619PDGFRB
T59102DI0403Thrombocytopenia[ICD-11: 3B64]P09619PDGFRB
T50269DI0411Tonus and reflex abnormality[ICD-11: MB47]P23415GLRA1
T45262DI0394Staphylococcal/streptococcal disease[ICD-11: 1B5Y]P34998CRHR1
T84634DI0314Oesophagitis[ICD-11: DA24]O43174CYP26A1
T00176DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q00987MDM2
T00176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q00987MDM2
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
T51883DI0252Melanoma[ICD-11: 2C30]P04049RAF1
T51883DI0303Non-small-cell lung cancer[ICD-11: 2C25]P04049RAF1
T51883DI0321Ovarian cancer[ICD-11: 2C73]P04049RAF1
T51883DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04049RAF1
T99089DI0252Melanoma[ICD-11: 2C30]P15056BRAF
T19433DI0148Flatworm infection[ICD-11: 1F70-1F86]O60760HPGDS
T36483DI0287Myocardial infarction[ICD-11: BA41-BA43]P25116F2R
T17569DI0030Angina pectoris[ICD-11: BA40]P22460KCNA5
T77400DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]O00408PDE2A
T77400DI0207Indeterminate colitis[ICD-11: DD72]O00408PDE2A
T77400DI0218Irritable bowel syndrome[ICD-11: DD91]O00408PDE2A
T77400DI0270Mood disorder[ICD-11: 6A60-6E23]O00408PDE2A
T94692DI0238Lung cancer[ICD-11: 2C25]P01130LDLR
T29683DI0254Menopausal disorder[ICD-11: GA30]P29371TACR3
T51282DI0166Glaucoma[ICD-11: 9C61]Q13464ROCK1
T55729DI0025Alzheimer disease[ICD-11: 8A20]Q15759MAPK11
T55729DI0366Rheumatoid arthritis[ICD-11: FA20]Q15759MAPK11
T86528DI0057Bone paget disease[ICD-11: FB85]O95749GGPS1
T86528DI0237Low bone mass disorder[ICD-11: FB83]O95749GGPS1
T86528DI0267Mineral excesses[ICD-11: 5B91]O95749GGPS1
T86528DI0281Musculoskeletal disorder[ICD-11: FA00-FC0Z]O95749GGPS1

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