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



Compound IDCDAMM01565
Common name(R)-3,4-Dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol
IUPAC name2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol
Molecular formulaC26H38O2

Experimental data

Retention time18.53
Adduct[M+H]+
Actual mz383.291
Theoretical mz383.294
Error8.55
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.4041

Identifiers and class information

Inchi keyGJJVAFUKOBZPCB-ZGRPYONQNA-N
SmilesOC1=CC=C2OC(C)(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)6
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)382.585
Computed dipole moment(dipole)2.545
Total solvent accessible surface area (SASA)832.319
Hydrophobic component of SASA (FOSA)625.148
Hydrophilic component of SASA (FISA)54.685
Pie component of the SASA (PISA)152.486
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1471.92
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)1.5
Free energy of solvation of dipole (dip^2/V)0.0043998
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0018022
Globularity descriptor (glob)0.751848
Predicted polarizability in cubic angstroms (QPpolrz)47.787
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.912
Predicted octanol/gas partition coefficient (QPlogPoct)17.271
Predicted water/gas partition coefficient (QPlogPw)3.868
Predicted octanol/water partition coefficient (QPlogPo/w)7.748
Predicted aqueous solubility (QPlogS)-9.355
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.797
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.275
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)3001.39
Predicted brain/blood partition coefficient (QPlogBB)-0.684
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1622.85
Predicted skin permeability, log Kp (QPlogKp)-1.03
PM3 calculated ionization potential (IP(ev))8.634
PM3 calculated electron affinity (EA(eV))-0.229
Number of likely metabolic reactions (#metab)11
Prediction of binding to human serum albumin (QPlogKhsa)1.958
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)29.141
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
P54289CACNA2D1Voltage-gated calcium channel alpha2/delta subunit 1 (by homology)T84316SwissTargetPrediction
P06239LCKTyrosine-protein kinase LCKT12499SwissTargetPrediction
P48449LSSLanosterol synthaseT56175SEA
P21554CNR1Cannabinoid receptor 1 (by homology)T76685SwissTargetPrediction
Q05586GRIN1Glutamate NMDA receptor; GRIN1/GRIN2BT62276SwissTargetPrediction
P43235CTSKCathepsin KT11388SwissTargetPrediction
P15538CYP11B1Cytochrome P450 11B1T84621SwissTargetPrediction
Q99705MCHR1Melanin-concentrating hormone receptor 1T09572SwissTargetPrediction
P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
P35968KDRVascular endothelial growth factor receptor 2T80975SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
Q8TDU6GPBAR1G-protein coupled bile acid receptor 1T86273SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction
P17655CAPN2Calpain 2T86837SwissTargetPrediction
Q14534SQLESqualene monooxygenase (by homology)T93344SEA
P21731TBXA2RThromboxane A2 receptorT76198SwissTargetPrediction
P52732KIF11Kinesin-like protein 1T28484SwissTargetPrediction
Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
P30291WEE1Serine/threonine-protein kinase WEE1T69991SwissTargetPrediction
Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
Q16769QPCTGlutaminyl-peptide cyclotransferaseT46245SwissTargetPrediction
P62942FKBP1AFK506-binding protein 1AT76059SwissTargetPrediction
P05093CYP17A1Cytochrome P450 17A1T89041SwissTargetPrediction
P20701ITGALIntercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2T35640SwissTargetPrediction
Q13418ILKSerine/threonine-protein kinase ILK-1T13616SwissTargetPrediction
P31749AKT1Serine/threonine-protein kinase AKTT67619SwissTargetPrediction
Q99685MGLLMonoglyceride lipaseT18664SwissTargetPrediction
P25774CTSSCathepsin ST68290SwissTargetPrediction
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction
P28482MAPK1MAP kinase ERK2T58970SwissTargetPrediction
P23415GLRA1Glycine receptor subunit alpha-1T50269SwissTargetPrediction
Q92793CREBBPCREB-binding protein/p53T03634SwissTargetPrediction
P34998CRHR1Corticotropin releasing factor receptor 1 (by homology)T45262SwissTargetPrediction
Q99835SMOSmoothened homologT66505SwissTargetPrediction
O43174CYP26A1Cytochrome P450 26A1T84634SwissTargetPrediction
P32239CCKBRCholecystokinin B receptor (by homology)T05849SwissTargetPrediction
Q00987MDM2p53-binding protein Mdm-2T00176SwissTargetPrediction
P02753RBP4Plasma retinol-binding proteinT55703SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P08151GLI1Zinc finger protein GLI1T40890SwissTargetPrediction
P04049RAF1Serine/threonine-protein kinase RAFT51883SwissTargetPrediction
P15056BRAFSerine/threonine-protein kinase B-rafT99089SwissTargetPrediction
O75908SOAT2Acyl coenzyme A:cholesterol acyltransferase 2T14463SwissTargetPrediction
P30536TSPOTranslocator protein (by homology)T75440SwissTargetPrediction
P42226STAT6Signal transducer and activator of transcription 6T20585SwissTargetPrediction
Q15759MAPK11MAP kinase p38 betaT55729SwissTargetPrediction
Q14330GPR18N-arachidonyl glycine receptorT72267SwissTargetPrediction
P53582METAP1Methionine aminopeptidase 1T42337SwissTargetPrediction
O95749GGPS1GeranyltranstransferaseT86528SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T84316DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P54289CACNA2D1
T84316DI0190Hypertension[ICD-11: BA00-BA04]P54289CACNA2D1
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
T84621DI0062Breast cancer[ICD-11: 2C60-2C6Y]P15538CYP11B1
T84621DI0108Cushing syndrome[ICD-11: 5A70]P15538CYP11B1
T09572DI0308Obesity[ICD-11: 5B80-5B81]Q99705MCHR1
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
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
T86273DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q8TDU6GPBAR1
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T86837DI0106COVID-19[ICD-11: 1D6Y]P17655CAPN2
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T76198DI0102Coronary atherosclerosis[ICD-11: BA52]P21731TBXA2R
T76198DI0121Diabetic foot ulcer[ICD-11: BD54]P21731TBXA2R
T76198DI0287Myocardial infarction[ICD-11: BA41-BA43]P21731TBXA2R
T76198DI0378Sexual dysfunction[ICD-11: HA00-HA01]P21731TBXA2R
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
T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
T69991DI0321Ovarian cancer[ICD-11: 2C73]P30291WEE1
T69991DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P30291WEE1
T69991DI0429Uterine ligament/parametrium/uterine adnexa neoplasm[ICD-11: 2C72]P30291WEE1
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
T46245DI0115Dementia[ICD-11: 6D80-6D8Z]Q16769QPCT
T76059DI0331Parkinsonism[ICD-11: 8A00]P62942FKBP1A
T76059DI0349Pruritus[ICD-11: EC90]P62942FKBP1A
T76059DI0413Transplant rejection[ICD-11: NE84]P62942FKBP1A
T89041DI0346Prostate cancer[ICD-11: 2C82]P05093CYP17A1
T35640DI0351Psoriasis[ICD-11: EA90]P20701ITGAL
T35640DI0436Visual system disease[ICD-11: 9E1Z]P20701ITGAL
T13616DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q13418ILK
T67619DI0062Breast cancer[ICD-11: 2C60-2C6Y]P31749AKT1
T18664DI0163General pain disorder[ICD-11: 8E43]Q99685MGLL
T18664DI0409Tic disorder[ICD-11: 8A05]Q99685MGLL
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
T58970DI0036Arteries/arterioles disorder[ICD-11: BD52]P28482MAPK1
T58970DI0252Melanoma[ICD-11: 2C30]P28482MAPK1
T58970DI0326Pancreatic cancer[ICD-11: 2C10]P28482MAPK1
T58970DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28482MAPK1
T50269DI0411Tonus and reflex abnormality[ICD-11: MB47]P23415GLRA1
T03634DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q92793CREBBP
T03634DI0346Prostate cancer[ICD-11: 2C82]Q92793CREBBP
T03634DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92793CREBBP
T03634DI0399Systemic sclerosis[ICD-11: 4A42]Q92793CREBBP
T45262DI0394Staphylococcal/streptococcal disease[ICD-11: 1B5Y]P34998CRHR1
T66505DI0047Basal cell carcinoma[ICD-11: 2C32]Q99835SMO
T66505DI0085Chronic myelomonocytic leukaemia[ICD-11: 2A40]Q99835SMO
T66505DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q99835SMO
T84634DI0314Oesophagitis[ICD-11: DA24]O43174CYP26A1
T05849DI0122Diagnostic imaging[ICD-11: N.A.]P32239CCKBR
T05849DI0327Pancreatic internal secretion disorder[ICD-11: 5A4Y]P32239CCKBR
T00176DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q00987MDM2
T00176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q00987MDM2
T55703DI0212Inherited retinal dystrophy[ICD-11: 9B70]P02753RBP4
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
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
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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