Heudelotinone



Compound IDCDAMM00857
Common nameHeudelotinone
IUPAC name14-hydroxy-7,7,13-trimethyltricyclo[9.4.0.03,8]pentadeca-1(11),2,4,12,14-pentaen-6-one
Molecular formulaC18H20O2

Experimental data

Retention time16.13
Adduct[M+H]+
Actual mz269.154
Theoretical mz269.153
Error1.58
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2349

Identifiers and class information

Inchi keyCGDLYSDMNSOBAM-GGYSOQFKNA-N
SmilesO=C1C=CC2=CC=3C=C(O)C(=CC3CCC2C1(C)C)C
SuperclassBenzenoids
ClassPhenols

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)1
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)268.355
Computed dipole moment(dipole)3.914
Total solvent accessible surface area (SASA)527.214
Hydrophobic component of SASA (FOSA)294.549
Hydrophilic component of SASA (FISA)85.656
Pie component of the SASA (PISA)147.009
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)921.05
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)2.75
Free energy of solvation of dipole (dip^2/V)0.0166353
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0052161
Globularity descriptor (glob)0.86836
Predicted polarizability in cubic angstroms (QPpolrz)31.468
Predicted hexadecane/gas partition coefficient (QPlogPC16)8.68
Predicted octanol/gas partition coefficient (QPlogPoct)13.172
Predicted water/gas partition coefficient (QPlogPw)6.523
Predicted octanol/water partition coefficient (QPlogPo/w)3.476
Predicted aqueous solubility (QPlogS)-4.808
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.002
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.363
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1526.26
Predicted brain/blood partition coefficient (QPlogBB)-0.254
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)781.32
Predicted skin permeability, log Kp (QPlogKp)-2.484
PM3 calculated ionization potential (IP(ev))8.893
PM3 calculated electron affinity (EA(eV))0.877
Number of likely metabolic reactions (#metab)4
Prediction of binding to human serum albumin (QPlogKhsa)0.555
Predicted qualitative human oral absorption (HumanOralAbsorption)3
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)46.186
Number of nitrogen and oxygen atoms (#NandO)2
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
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P09874PARP1Poly [ADP-ribose] polymerase-1T06273SwissTargetPrediction
P21917DRD4Dopamine D4 receptorT24983SwissTargetPrediction
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P16083NQO2Quinone reductase 2T75498SwissTargetPrediction
P14555PLA2G2APhospholipase A2 group IIAT19160SwissTargetPrediction
P34913EPHX2Epoxide hydrataseT35734SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
P41595HTR2BSerotonin 2b (5-HT2b) receptorT31204SwissTargetPrediction
P07949RETKinesin-1 heavy chain/ Tyrosine-protein kinase receptor RETT60631SwissTargetPrediction
P08913ADRA2AAlpha-2a adrenergic receptorT11448SwissTargetPrediction
Q14416GRM2Metabotropic glutamate receptor 2T62820SwissTargetPrediction
P43235CTSKCathepsin KT11388SwissTargetPrediction
Q9UBN7HDAC6Histone deacetylase 6T22274SwissTargetPrediction
P10275ARAndrogen ReceptorT11211SwissTargetPrediction
Q92731ESR2Estrogen receptor betaT80896SwissTargetPrediction
Q8NER1TRPV1Vanilloid receptorT83193SwissTargetPrediction
P04150NR3C1Glucocorticoid receptorT40016SwissTargetPrediction
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
P03372ESR1Estrogen receptor alphaT02506SwissTargetPrediction
P14174MIFMacrophage migration inhibitory factorT39977SwissTargetPrediction
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
Q9BY41HDAC8Histone deacetylase 8T28887SwissTargetPrediction
P35462DRD3Dopamine D3 receptorT02551SwissTargetPrediction
P21728DRD1Dopamine D1 receptorT22118SwissTargetPrediction
P21918DRD5Dopamine D5 receptorT46828SwissTargetPrediction
P52732KIF11Kinesin-like protein 1T28484SwissTargetPrediction
P14061HSD17B1Estradiol 17-beta-dehydrogenase 1T44011SwissTargetPrediction
P24941CDK2Cyclin-dependent kinase 2T70176SwissTargetPrediction
P16050ALOX15Arachidonate 15-lipoxygenaseT16042SwissTargetPrediction
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SwissTargetPrediction
P05093CYP17A1Cytochrome P450 17A1T89041SwissTargetPrediction
O75116ROCK2Rho-associated protein kinase 2T06093SwissTargetPrediction
Q99685MGLLMonoglyceride lipaseT18664SwissTargetPrediction
P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
P08238HSP90AB1Heat shock protein HSP 90-betaT96623SwissTargetPrediction
P49810PSEN2Gamma-secretaseT99204SwissTargetPrediction
Q15078CDK5R1Cyclin-dependent kinase 5/CDK5 activator 1T09513SwissTargetPrediction
Q13627DYRK1ADual-specificity tyrosine-phosphorylation regulated kinase 1AT92803SwissTargetPrediction
P08842STSSteryl-sulfataseT33489SwissTargetPrediction
P06493CDK1Cyclin-dependent kinase 1/cyclin B1T49898SwissTargetPrediction
P49840GSK3AGlycogen synthase kinase-3 alphaT76910SwissTargetPrediction
Q00535CDK5Cyclin-dependent kinase 5/CDK5 activator 1T20973SwissTargetPrediction
P11597CETPCholesteryl ester transfer proteinT15334SwissTargetPrediction
P19793RXRARetinoid X receptor alpha (by homology)T13726SwissTargetPrediction
P02753RBP4Plasma retinol-binding proteinT55703SwissTargetPrediction
Q13976PRKG1cGMP-dependent protein kinase 1 betaT78543SwissTargetPrediction
Q04759PRKCQProtein kinase C thetaT23995SwissTargetPrediction
Q96GD4AURKBSerine/threonine-protein kinase Aurora-BT46781SwissTargetPrediction
P13569CFTRCystic fibrosis transmembrane conductance regulatorT55654SwissTargetPrediction
Q15746MYLKMyosin light chain kinase, smooth muscleT97141SwissTargetPrediction
P22607FGFR3Fibroblast growth factor receptor 3T91331SwissTargetPrediction
P55055NR1H2LXR-betaT13714SwissTargetPrediction
Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SwissTargetPrediction
Q99814EPAS1Endothelial PAS domain-containing protein 1T21123SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T06273DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P09874PARP1
T06273DI0143Fallopian tube cancer[ICD-11: 2C74]P09874PARP1
T06273DI0321Ovarian cancer[ICD-11: 2C73]P09874PARP1
T06273DI0334Peritoneal cancer[ICD-11: 2C51]P09874PARP1
T24983DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21917DRD4
T24983DI0370Schizophrenia[ICD-11: 6A20]P21917DRD4
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
T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
T19160DI0062Breast cancer[ICD-11: 2C60-2C6Y]P14555PLA2G2A
T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
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
T60631DI0095Colorectal cancer[ICD-11: 2B91]P07949RET
T60631DI0238Lung cancer[ICD-11: 2C25]P07949RET
T60631DI0250Mature B-cell lymphoma[ICD-11: 2A85]P07949RET
T60631DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P07949RET
T60631DI0403Thrombocytopenia[ICD-11: 3B64]P07949RET
T60631DI0407Thyroid cancer[ICD-11: 2D10]P07949RET
T11448DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P08913ADRA2A
T11448DI0317Opioid use disorder[ICD-11: 6C43]P08913ADRA2A
T11448DI0396Substance abuse[ICD-11: 6C40]P08913ADRA2A
T62820DI0025Alzheimer disease[ICD-11: 8A20]Q14416GRM2
T62820DI0051Bipolar disorder[ICD-11: 6A60]Q14416GRM2
T62820DI0116Dengue fever[ICD-11: 1D2Z]Q14416GRM2
T62820DI0117Depression[ICD-11: 6A70-6A7Z]Q14416GRM2
T62820DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]Q14416GRM2
T62820DI0256Mental/behavioural/neurodevelopmental disorder[ICD-11: 6E20-6E8Z]Q14416GRM2
T62820DI0308Obesity[ICD-11: 5B80-5B81]Q14416GRM2
T62820DI0354Psychotic disorder[ICD-11: 6A20-6A25]Q14416GRM2
T62820DI0370Schizophrenia[ICD-11: 6A20]Q14416GRM2
T11388DI0237Low bone mass disorder[ICD-11: FB83]P43235CTSK
T22274DI0274Multiple myeloma[ICD-11: 2A83]Q9UBN7HDAC6
T22274DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UBN7HDAC6
T11211DI0005Acne vulgaris[ICD-11: ED80]P10275AR
T11211DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10275AR
T11211DI0021Alcoholic liver disease[ICD-11: DB94]P10275AR
T11211DI0062Breast cancer[ICD-11: 2C60-2C6Y]P10275AR
T11211DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P10275AR
T11211DI0145Female pelvic pain[ICD-11: GA34]P10275AR
T11211DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P10275AR
T11211DI0237Low bone mass disorder[ICD-11: FB83]P10275AR
T11211DI0247Mammary tumour[ICD-11: 2C60-2C6Z]P10275AR
T11211DI0346Prostate cancer[ICD-11: 2C82]P10275AR
T11211DI0401Testicular dysfunction[ICD-11: 5A81]P10275AR
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
T83193DI0163General pain disorder[ICD-11: 8E43]Q8NER1TRPV1
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
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
T39977DI0403Thrombocytopenia[ICD-11: 3B64]P14174MIF
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T28887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9BY41HDAC8
T02551DI0051Bipolar disorder[ICD-11: 6A60]P35462DRD3
T02551DI0331Parkinsonism[ICD-11: 8A00]P35462DRD3
T22118DI0003Abortion[ICD-11: JA00]P21728DRD1
T22118DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P21728DRD1
T22118DI0190Hypertension[ICD-11: BA00-BA04]P21728DRD1
T22118DI0331Parkinsonism[ICD-11: 8A00]P21728DRD1
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
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
T89041DI0346Prostate cancer[ICD-11: 2C82]P05093CYP17A1
T06093DI0168Graft-versus-host disease[ICD-11: 4B24]O75116ROCK2
T18664DI0163General pain disorder[ICD-11: 8E43]Q99685MGLL
T18664DI0409Tic disorder[ICD-11: 8A05]Q99685MGLL
T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
T96623DI0062Breast cancer[ICD-11: 2C60-2C6Y]P08238HSP90AB1
T96623DI0238Lung cancer[ICD-11: 2C25]P08238HSP90AB1
T96623DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P08238HSP90AB1
T96623DI0249Mature B-cell leukaemia[ICD-11: 2A82]P08238HSP90AB1
T96623DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P08238HSP90AB1
T96623DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P08238HSP90AB1
T96623DI0395Stomach cancer[ICD-11: 2B72]P08238HSP90AB1
T99204DI0320Osteoarthritis[ICD-11: FA00-FA05]P49810PSEN2
T99204DI0380Shoulder lesion[ICD-11: FB53]P49810PSEN2
T99204DI0390Soft tissue disorder[ICD-11: FB56]P49810PSEN2
T92803DI0113Cytomegaloviral disease[ICD-11: 1D82]Q13627DYRK1A
T33489DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P08842STS
T49898DI0062Breast cancer[ICD-11: 2C60-2C6Y]P06493CDK1
T49898DI0238Lung cancer[ICD-11: 2C25]P06493CDK1
T49898DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P06493CDK1
T49898DI0250Mature B-cell lymphoma[ICD-11: 2A85]P06493CDK1
T49898DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06493CDK1
T76910DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P49840GSK3A
T20973DI0308Obesity[ICD-11: 5B80-5B81]Q00535CDK5
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
T55703DI0212Inherited retinal dystrophy[ICD-11: 9B70]P02753RBP4
T23995DI0413Transplant rejection[ICD-11: NE84]Q04759PRKCQ
T46781DI0009Acute diabete complication[ICD-11: 5A2Y]Q96GD4AURKB
T46781DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q96GD4AURKB
T55654DI0110Cystic fibrosis[ICD-11: CA25]P13569CFTR
T55654DI0217Intrathoracic organs injury[ICD-11: NB32]P13569CFTR
T55654DI0435Viral intestinal infection[ICD-11: 1A2Z]P13569CFTR
T97141DI0127Duodenal ulcer[ICD-11: DA63]Q15746MYLK
T91331DI0102Coronary atherosclerosis[ICD-11: BA52]P22607FGFR3
T91331DI0235Liver cancer[ICD-11: 2C12]P22607FGFR3
T91331DI0287Myocardial infarction[ICD-11: BA41-BA43]P22607FGFR3
T13714DI0039Atopic eczema[ICD-11: EA80]P55055NR1H2
T21123DI0019Adrenomedullary hyperfunction[ICD-11: 5A75]Q99814EPAS1

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