(+)-9-O-Demethylhomolycorine



Compound IDCDAMM00556
Common name(+)-9-O-Demethylhomolycorine
IUPAC name9-hydroxy-10-methoxy-1-methyl-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-7-one
Molecular formulaC17H19NO4

Experimental data

Retention time8.06
Adduct[2M+Na]+
Actual mz625.248
Theoretical mz625.251
Error5.47
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.7618

Identifiers and class information

Inchi keyVLDOBKJPRUQEEC-HLRBPWBTNA-N
SmilesO=C1OC2CC=C3CCN(C)C3C2C4=CC(OC)=C(O)C=C14
SuperclassAlkaloids and derivatives
ClassAmaryllidaceae alkaloids

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)1
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)2
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)1
Molecular weight (mol_MW)301.341
Computed dipole moment(dipole)6.635
Total solvent accessible surface area (SASA)513.942
Hydrophobic component of SASA (FOSA)306.29
Hydrophilic component of SASA (FISA)116.451
Pie component of the SASA (PISA)91.202
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)924.674
Number of hydrogen bond donors (donorHB)1
Number of hydrogen bond acceptors (accptHB)6.5
Free energy of solvation of dipole (dip^2/V)0.0476139
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0126473
Globularity descriptor (glob)0.89312
Predicted polarizability in cubic angstroms (QPpolrz)30.438
Predicted hexadecane/gas partition coefficient (QPlogPC16)8.663
Predicted octanol/gas partition coefficient (QPlogPoct)15.363
Predicted water/gas partition coefficient (QPlogPw)9.794
Predicted octanol/water partition coefficient (QPlogPo/w)1.197
Predicted aqueous solubility (QPlogS)-1.871
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.363
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.423
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)194.31
Predicted brain/blood partition coefficient (QPlogBB)-0.132
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)93.149
Predicted skin permeability, log Kp (QPlogKp)-5.215
PM3 calculated ionization potential (IP(ev))9.109
PM3 calculated electron affinity (EA(eV))0.524
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-0.157
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)74.915
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)74.332
Number of nitrogen and oxygen atoms (#NandO)5
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
Q9Y5N1HRH3Histamine H3 receptorT64765SwissTargetPrediction
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
Q12809KCNH2HERGT20251SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
P09874PARP1Poly [ADP-ribose] polymerase-1T06273SwissTargetPrediction
P21917DRD4Dopamine D4 receptorT24983SwissTargetPrediction
P16083NQO2Quinone reductase 2T75498SwissTargetPrediction
P27487DPP4Dipeptidyl peptidase IVT31391SwissTargetPrediction
P27338MAOBMonoamine oxidase BT83011SwissTargetPrediction
P28223HTR2ASerotonin 2a (5-HT2a) receptorT32060SwissTargetPrediction
P41595HTR2BSerotonin 2b (5-HT2b) receptorT31204SwissTargetPrediction
P32297CHRNA3Neuronal acetylcholine receptor; alpha3/beta4T74166SwissTargetPrediction
P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SwissTargetPrediction
P28566HTR1ESerotonin 1e (5-HT1e) receptorT84117SwissTargetPrediction
P80404ABATGamma-amino-N-butyrate transaminaseT59045SwissTargetPrediction
O60885BRD4Bromodomain-containing protein 4T00407SwissTargetPrediction
Q9H3N8HRH4Histamine H4 receptorT26500SwissTargetPrediction
P35367HRH1Histamine H1 receptorT77913SwissTargetPrediction
P21728DRD1Dopamine D1 receptorT22118SEA
P21918DRD5Dopamine D5 receptorT46828SwissTargetPrediction
Q13639HTR4Serotonin 4 (5-HT4) receptorT59679SwissTargetPrediction
P18825ADRA2CAdrenergic receptor alpha-2T01777SwissTargetPrediction
P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
O14757CHEK1Serine/threonine-protein kinase Chk1T62449SwissTargetPrediction
O60674JAK2Tyrosine-protein kinase JAK2T08391SwissTargetPrediction
Q9P1W9PIM2Serine/threonine-protein kinase PIM2T07279SwissTargetPrediction
Q86V86PIM3Serine/threonine-protein kinase PIM3T16596SwissTargetPrediction
P32245MC4RMelanocortin receptor 4T72458SwissTargetPrediction
Q13490BIRC2Baculoviral IAP repeat-containing protein 2T84780SwissTargetPrediction
O14746TERTTelomerase reverse transcriptaseT86052SwissTargetPrediction
P48147PREPProlyl endopeptidaseT86161SwissTargetPrediction
Q9UHL4DPP7Dipeptidyl peptidase IIT50773SwissTargetPrediction
O75116ROCK2Rho-associated protein kinase 2T06093SwissTargetPrediction
P23458JAK1Tyrosine-protein kinase JAK1T62460SwissTargetPrediction
P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
O96017CHEK2Serine/threonine-protein kinase Chk2T28713SwissTargetPrediction
Q12884FAPFibroblast activation protein alpha (by homology)T53764SwissTargetPrediction
P52333JAK3Tyrosine-protein kinase JAK3T23172SwissTargetPrediction
P47898HTR5ASerotonin 5a (5-HT5a) receptorT15571SwissTargetPrediction
P06493CDK1Cyclin-dependent kinase 1/cyclin B1T49898SwissTargetPrediction
P42574CASP3Caspase-3T57943SwissTargetPrediction
P46098HTR3ASerotonin 3a (5-HT3a) receptorT64591SwissTargetPrediction
P31391SSTR4Somatostatin receptor 4T62974SwissTargetPrediction
Q13976PRKG1cGMP-dependent protein kinase 1 betaT78543SwissTargetPrediction
Q04759PRKCQProtein kinase C thetaT23995SwissTargetPrediction
P68400CSNK2A1Casein kinase II alphaT51565SwissTargetPrediction
Q6V1X1DPP8Dipeptidyl peptidase VIIIT15855SwissTargetPrediction
Q86TI2DPP9Dipeptidyl peptidase IXT66252SwissTargetPrediction
P19784CSNK2A2Casein kinase II alpha (prime)T80526SwissTargetPrediction
P30307CDC25CDual specificity phosphatase Cdc25CT40569SwissTargetPrediction
Q96KB5PBKPDZ-binding kinaseT98642SwissTargetPrediction
P15559NQO1Quinone reductase 1T52389SwissTargetPrediction
P30939HTR1FSerotonin 1f (5-HT1f) receptorT78656SwissTargetPrediction
Q92952KCNN1Small conductance calcium-activated potassium channel protein 1T11911SEA
Q9UGI6KCNN3Small conductance calcium-activated potassium channel protein 3T04388SEA
P51512MMP16Matrix metalloproteinase 16T35824SEA
P51511MMP15Matrix metalloproteinase 15T81658SEA
P53634CTSCDipeptidyl peptidase IT70490SwissTargetPrediction
P48048KCNJ1ATP-sensitive inward rectifier potassium channel 1T78710SwissTargetPrediction
P05231IL6Interleukin-6T32578SEA
Q9H2S1KCNN2Small conductance calcium-activated potassium channel protein 2T86271SEA

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
T64765DI0392Somnolence[ICD-11: MG42]Q9Y5N1HRH3
T30082DI0025Alzheimer disease[ICD-11: 8A20]P22303ACHE
T30082DI0166Glaucoma[ICD-11: 9C61]P22303ACHE
T30082DI0282Myasthenia gravis[ICD-11: 8C6Y]P22303ACHE
T30082DI0313Oesophageal/gastroduodenal disorder[ICD-11: DD90]P22303ACHE
T30082DI0332Pediculosis[ICD-11: 1G00]P22303ACHE
T30082DI0421Unspecific substance harmful effect[ICD-11: NE6Z]P22303ACHE
T20251DI0175Heart failure[ICD-11: BD10-BD1Z]Q12809KCNH2
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
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
T75498DI0214Insomnia[ICD-11: 7A00-7A0Z]P16083NQO2
T31391DI0009Acute diabete complication[ICD-11: 5A2Y]P27487DPP4
T31391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P27487DPP4
T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
T32060DI0009Acute diabete complication[ICD-11: 5A2Y]P28223HTR2A
T32060DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P28223HTR2A
T32060DI0073Cerebral ischaemia[ICD-11: 8B1Z]P28223HTR2A
T32060DI0270Mood disorder[ICD-11: 6A60-6E23]P28223HTR2A
T32060DI0331Parkinsonism[ICD-11: 8A00]P28223HTR2A
T32060DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28223HTR2A
T32060DI0370Schizophrenia[ICD-11: 6A20]P28223HTR2A
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
T74166DI0105Cough[ICD-11: MD12]P32297CHRNA3
T78709DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P08908HTR1A
T78709DI0117Depression[ICD-11: 6A70-6A7Z]P08908HTR1A
T78709DI0190Hypertension[ICD-11: BA00-BA04]P08908HTR1A
T78709DI0264Migraine[ICD-11: 8A80]P08908HTR1A
T78709DI0270Mood disorder[ICD-11: 6A60-6E23]P08908HTR1A
T84117DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P28566HTR1E
T59045DI0060Brain cancer[ICD-11: 2A00]P80404ABAT
T59045DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P80404ABAT
T59045DI0135Epileptic encephalopathy[ICD-11: 8A62]P80404ABAT
T59045DI0266Mineral deficiency[ICD-11: 5B5K]P80404ABAT
T59045DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P80404ABAT
T26500DI0037Asthma[ICD-11: CA23]Q9H3N8HRH4
T26500DI0039Atopic eczema[ICD-11: EA80]Q9H3N8HRH4
T26500DI0351Psoriasis[ICD-11: EA90]Q9H3N8HRH4
T26500DI0366Rheumatoid arthritis[ICD-11: FA20]Q9H3N8HRH4
T26500DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q9H3N8HRH4
T77913DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P35367HRH1
T77913DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P35367HRH1
T77913DI0063Breathing abnormality[ICD-11: MD11]P35367HRH1
T77913DI0099Conjunctiva disorder[ICD-11: 9A60]P35367HRH1
T77913DI0105Cough[ICD-11: MD12]P35367HRH1
T77913DI0117Depression[ICD-11: 6A70-6A7Z]P35367HRH1
T77913DI0136Episodic vestibular syndrome[ICD-11: AB31]P35367HRH1
T77913DI0173Headache[ICD-11: 8A80-8A84]P35367HRH1
T77913DI0214Insomnia[ICD-11: 7A00-7A0Z]P35367HRH1
T77913DI0272Morning sickness disorder[ICD-11: SC00]P35367HRH1
T77913DI0292Nasopharyngitis[ICD-11: CA00]P35367HRH1
T77913DI0293Nausea/vomiting[ICD-11: MD90]P35367HRH1
T77913DI0331Parkinsonism[ICD-11: 8A00]P35367HRH1
T77913DI0349Pruritus[ICD-11: EC90]P35367HRH1
T77913DI0366Rheumatoid arthritis[ICD-11: FA20]P35367HRH1
T77913DI0388Sleep-wake disorder[ICD-11: 7A00-7B2Z]P35367HRH1
T77913DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]P35367HRH1
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
T59679DI0161Gastro-oesophageal reflux disease[ICD-11: DA22]Q13639HTR4
T59679DI0218Irritable bowel syndrome[ICD-11: DD91]Q13639HTR4
T01777DI0166Glaucoma[ICD-11: 9C61]P18825ADRA2C
T01777DI0190Hypertension[ICD-11: BA00-BA04]P18825ADRA2C
T01777DI0196Hypotension[ICD-11: BA20-BA21]P18825ADRA2C
T01777DI0308Obesity[ICD-11: 5B80-5B81]P18825ADRA2C
T01777DI0310Ocular disease[ICD-11: N.A.]P18825ADRA2C
T01777DI0396Substance abuse[ICD-11: 6C40]P18825ADRA2C
T50594DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11309PIM1
T50594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11309PIM1
T62449DI0027Anal cancer[ICD-11: 2C00]O14757CHEK1
T62449DI0172Head and neck cancer[ICD-11: 2D42]O14757CHEK1
T62449DI0183Hodgkin lymphoma[ICD-11: 2B30]O14757CHEK1
T62449DI0238Lung cancer[ICD-11: 2C25]O14757CHEK1
T62449DI0241Lymphoma[ICD-11: 2A80-2A86]O14757CHEK1
T62449DI0321Ovarian cancer[ICD-11: 2C73]O14757CHEK1
T62449DI0326Pancreatic cancer[ICD-11: 2C10]O14757CHEK1
T62449DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14757CHEK1
T08391DI0039Atopic eczema[ICD-11: EA80]O60674JAK2
T08391DI0286Myeloproliferative neoplasm[ICD-11: 2A20]O60674JAK2
T08391DI0366Rheumatoid arthritis[ICD-11: FA20]O60674JAK2
T08391DI0404Thrombocytosis[ICD-11: 3B63]O60674JAK2
T07279DI0274Multiple myeloma[ICD-11: 2A83]Q9P1W9PIM2
T07279DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9P1W9PIM2
T72458DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]P32245MC4R
T72458DI0228Large intestine motility disorder[ICD-11: DB32]P32245MC4R
T72458DI0308Obesity[ICD-11: 5B80-5B81]P32245MC4R
T84780DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]Q13490BIRC2
T86052DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]O14746TERT
T86052DI0284Myelodysplastic syndrome[ICD-11: 2A37]O14746TERT
T86052DI0326Pancreatic cancer[ICD-11: 2C10]O14746TERT
T86161DI0092Coeliac disease[ICD-11: DA95]P48147PREP
T86161DI0210Influenza[ICD-11: 1E30-1E32]P48147PREP
T86161DI0238Lung cancer[ICD-11: 2C25]P48147PREP
T86161DI0265Mild neurocognitive disorder[ICD-11: 6D71]P48147PREP
T06093DI0168Graft-versus-host disease[ICD-11: 4B24]O75116ROCK2
T62460DI0039Atopic eczema[ICD-11: EA80]P23458JAK1
T62460DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P23458JAK1
T62460DI0366Rheumatoid arthritis[ICD-11: FA20]P23458JAK1
T62460DI0404Thrombocytosis[ICD-11: 3B63]P23458JAK1
T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
T28713DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O96017CHEK2
T53764DI0300Neutropenia[ICD-11: 4B00]Q12884FAP
T23172DI0023Alopecia[ICD-11: ED70]P52333JAK3
T23172DI0039Atopic eczema[ICD-11: EA80]P52333JAK3
T23172DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P52333JAK3
T23172DI0366Rheumatoid arthritis[ICD-11: FA20]P52333JAK3
T15571DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P47898HTR5A
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
T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
T64591DI0087Chronic pain[ICD-11: MG30]P46098HTR3A
T64591DI0101Corneal disease[ICD-11: 9A76-9A78]P46098HTR3A
T64591DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P46098HTR3A
T64591DI0218Irritable bowel syndrome[ICD-11: DD91]P46098HTR3A
T64591DI0293Nausea/vomiting[ICD-11: MD90]P46098HTR3A
T62974DI0087Chronic pain[ICD-11: MG30]P31391SSTR4
T62974DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P31391SSTR4
T23995DI0413Transplant rejection[ICD-11: NE84]Q04759PRKCQ
T51565DI0104Coronavirus infection[ICD-11: 1D92]P68400CSNK2A1
T51565DI0235Liver cancer[ICD-11: 2C12]P68400CSNK2A1
T51565DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P68400CSNK2A1
T15855DI0300Neutropenia[ICD-11: 4B00]Q6V1X1DPP8
T66252DI0300Neutropenia[ICD-11: 4B00]Q86TI2DPP9
T98642DI0291Nasopharyngeal cancer[ICD-11: 2B6B]Q96KB5PBK
T52389DI0079Choreiform disorder[ICD-11: 8A01]P15559NQO1
T52389DI0090CNS anomalies syndrome[ICD-11: LD20]P15559NQO1
T52389DI0202Inborn energy metabolism error[ICD-11: 5C53]P15559NQO1
T52389DI0215Intellectual development disorder[ICD-11: LD90]P15559NQO1
T52389DI0326Pancreatic cancer[ICD-11: 2C10]P15559NQO1
T52389DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P15559NQO1
T78656DI0264Migraine[ICD-11: 8A80]P30939HTR1F
T78656DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30939HTR1F
T11911DI0285Myelopathy[ICD-11: 8B42]Q92952KCNN1
T04388DI0285Myelopathy[ICD-11: 8B42]Q9UGI6KCNN3
T70490DI0064Bronchiectasis[ICD-11: CA24]P53634CTSC
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T86271DI0285Myelopathy[ICD-11: 8B42]Q9H2S1KCNN2

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