Dronabinol



Compound IDCDAMM01369
Common nameDronabinol
IUPAC name6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
Molecular formulaC21H30O2

Experimental data

Retention time18.99
Adduct[M+H]+
Actual mz315.231
Theoretical mz315.232
Error3.73
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score8.5607

Identifiers and class information

Inchi keyCYQFCXCEBYINGO-IAGOWNOFSA-N
SmilesOC=1C=C(C=C2OC(C)(C)C3CCC(=CC3C12)C)CCCCC
SuperclassOrganoheterocyclic compounds
ClassBenzopyrans

Pharmacokinetic properties

Number of descriptor values(#stars)3
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)5
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)314.467
Computed dipole moment(dipole)1.208
Total solvent accessible surface area (SASA)649.471
Hydrophobic component of SASA (FOSA)527.559
Hydrophilic component of SASA (FISA)37.877
Pie component of the SASA (PISA)84.036
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1150.61
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)1.5
Free energy of solvation of dipole (dip^2/V)0.0012681
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0023096
Globularity descriptor (glob)0.817633
Predicted polarizability in cubic angstroms (QPpolrz)37.486
Predicted hexadecane/gas partition coefficient (QPlogPC16)9.987
Predicted octanol/gas partition coefficient (QPlogPoct)13.809
Predicted water/gas partition coefficient (QPlogPw)3.951
Predicted octanol/water partition coefficient (QPlogPo/w)5.71
Predicted aqueous solubility (QPlogS)-6.755
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.482
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.884
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)4332.29
Predicted brain/blood partition coefficient (QPlogBB)-0.116
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2413.05
Predicted skin permeability, log Kp (QPlogKp)-1.441
PM3 calculated ionization potential (IP(ev))8.965
PM3 calculated electron affinity (EA(eV))-0.277
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)1.26
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)26.606
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)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
P41594GRM5Metabotropic glutamate receptor 5T99347SwissTargetPrediction
P21397MAOAMonoamine oxidase AT83875SwissTargetPrediction
P16083NQO2Quinone reductase 2T75498SwissTargetPrediction
P21554CNR1Cannabinoid receptor 1 (by homology)T76685SwissTargetPrediction and SEA
P34913EPHX2Epoxide hydrataseT35734SwissTargetPrediction
P28335HTR2CSerotonin 2c (5-HT2c) receptorT83813SwissTargetPrediction
P41595HTR2BSerotonin 2b (5-HT2b) receptorT31204SwissTargetPrediction
Q92769HDAC2Histone deacetylase 2T51191SwissTargetPrediction
P35968KDRVascular endothelial growth factor receptor 2T80975SwissTargetPrediction
P07339CTSDCathepsin DT67102SwissTargetPrediction
P21731TBXA2RThromboxane A2 receptorT76198SwissTargetPrediction
P52732KIF11Kinesin-like protein 1T28484SwissTargetPrediction
Q9Y233PDE10APhosphodiesterase 10A (by homology)T84133SwissTargetPrediction
P32245MC4RMelanocortin receptor 4T72458SwissTargetPrediction
Q13418ILKSerine/threonine-protein kinase ILK-1T13616SwissTargetPrediction
P47871GCGRGlucagon receptorT60182SwissTargetPrediction
P30556AGTR1Type-1 angiotensin II receptorT74456SwissTargetPrediction
P40763STAT3Signal transducer and activator of transcription 3T29130SwissTargetPrediction
P34972CNR2Cannabinoid receptor 2T37693SwissTargetPrediction and SEA
P34995PTGER1Prostanoid EP1 receptorT15497SwissTargetPrediction
P23415GLRA1Glycine receptor subunit alpha-1T50269SwissTargetPrediction and SEA
P34998CRHR1Corticotropin releasing factor receptor 1 (by homology)T45262SwissTargetPrediction
P48067SLC6A9Glycine transporter 1T69685SwissTargetPrediction
P41180CASRCalcium sensing receptorT92076SwissTargetPrediction
P56373P2RX3P2X purinoceptor 3T17140SwissTargetPrediction
P30536TSPOTranslocator protein (by homology)T75440SwissTargetPrediction
P22460KCNA5Voltage-gated potassium channel subunit Kv1.5T17569SwissTargetPrediction
Q9Y2T6GPR55G-protein coupled receptor 55T87670SwissTargetPrediction
P51608MECP2Methyl-CpG-binding protein 2T59686SwissTargetPrediction
P13569CFTRCystic fibrosis transmembrane conductance regulatorT55654SwissTargetPrediction
Q9NPH5NOX4NADPH oxidase 4T29741SwissTargetPrediction
Q05513PRKCZProtein kinase C (PKC)T59190SwissTargetPrediction
Q13822ENPP2AutotaxinT63512SwissTargetPrediction
P50336PPOXProtoporphyrinogen oxidaseT34239SwissTargetPrediction
Q14330GPR18N-arachidonyl glycine receptorT72267SwissTargetPrediction and SEA
Q9Y256RCE1Prenyl protein specific proteaseT10756SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T02703DI0083Chronic kidney disease[ICD-11: GB61]P35228NOS2
T02703DI0320Osteoarthritis[ICD-11: FA00-FA05]P35228NOS2
T02703DI0375Sepsis[ICD-11: 1G40-1G41]P35228NOS2
T02703DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35228NOS2
T99347DI0152Fragile X chromosome[ICD-11: LD55]P41594GRM5
T99347DI0331Parkinsonism[ICD-11: 8A00]P41594GRM5
T83875DI0117Depression[ICD-11: 6A70-6A7Z]P21397MAOA
T83875DI0331Parkinsonism[ICD-11: 8A00]P21397MAOA
T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
T76685DI0031Anorexia nervosa[ICD-11: 6B80]P21554CNR1
T76685DI0214Insomnia[ICD-11: 7A00-7A0Z]P21554CNR1
T76685DI0308Obesity[ICD-11: 5B80-5B81]P21554CNR1
T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
T83813DI0117Depression[ICD-11: 6A70-6A7Z]P28335HTR2C
T83813DI0264Migraine[ICD-11: 8A80]P28335HTR2C
T83813DI0308Obesity[ICD-11: 5B80-5B81]P28335HTR2C
T83813DI0324Pain[ICD-11: MG30-MG3Z]P28335HTR2C
T83813DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28335HTR2C
T31204DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P41595HTR2B
T31204DI0117Depression[ICD-11: 6A70-6A7Z]P41595HTR2B
T31204DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P41595HTR2B
T31204DI0354Psychotic disorder[ICD-11: 6A20-6A25]P41595HTR2B
T51191DI0241Lymphoma[ICD-11: 2A80-2A86]Q92769HDAC2
T51191DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92769HDAC2
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
T67102DI0275Multiple sclerosis[ICD-11: 8A40]P07339CTSD
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
T84133DI0079Choreiform disorder[ICD-11: 8A01]Q9Y233PDE10A
T84133DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q9Y233PDE10A
T84133DI0218Irritable bowel syndrome[ICD-11: DD91]Q9Y233PDE10A
T84133DI0370Schizophrenia[ICD-11: 6A20]Q9Y233PDE10A
T84133DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9Y233PDE10A
T72458DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]P32245MC4R
T72458DI0228Large intestine motility disorder[ICD-11: DB32]P32245MC4R
T72458DI0308Obesity[ICD-11: 5B80-5B81]P32245MC4R
T13616DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q13418ILK
T60182DI0193Hypo-glycaemia[ICD-11: 5A41]P47871GCGR
T74456DI0137Essential hypertension[ICD-11: BA00]P30556AGTR1
T74456DI0190Hypertension[ICD-11: BA00-BA04]P30556AGTR1
T74456DI0373Secondary hypertension[ICD-11: BA04]P30556AGTR1
T74456DI0425Urinary system clinical symptom[ICD-11: MF8Y]P30556AGTR1
T29130DI0351Psoriasis[ICD-11: EA90]P40763STAT3
T37693DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P34972CNR2
T37693DI0214Insomnia[ICD-11: 7A00-7A0Z]P34972CNR2
T15497DI0405Thrombosis[ICD-11: DB61-GB90]P34995PTGER1
T50269DI0411Tonus and reflex abnormality[ICD-11: MB47]P23415GLRA1
T45262DI0394Staphylococcal/streptococcal disease[ICD-11: 1B5Y]P34998CRHR1
T69685DI0370Schizophrenia[ICD-11: 6A20]P48067SLC6A9
T92076DI0189Hyper-parathyroidism[ICD-11: 5A51]P41180CASR
T17140DI0105Cough[ICD-11: MD12]P56373P2RX3
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
T17569DI0030Angina pectoris[ICD-11: BA40]P22460KCNA5
T87670DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]Q9Y2T6GPR55
T59686DI0215Intellectual development disorder[ICD-11: LD90]P51608MECP2
T55654DI0110Cystic fibrosis[ICD-11: CA25]P13569CFTR
T55654DI0217Intrathoracic organs injury[ICD-11: NB32]P13569CFTR
T55654DI0435Viral intestinal infection[ICD-11: 1A2Z]P13569CFTR
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T59190DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q05513PRKCZ
T63512DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q13822ENPP2
T34239DI0133Epidermal dysplasias[ICD-11: EK90]P50336PPOX

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