Discarine K



Compound IDCDAMM00396
Common nameDiscarine K
IUPAC name2-(dimethylamino)-N-[11-hydroxy-7-(1H-indol-3-ylmethyl)-5,8-dioxo-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),12,15-trien-4-yl]-3-methylpentanamide
Molecular formulaC33H45N5O5

Experimental data

Retention time42.98
Adduct[M+H]+
Actual mz592.354
Theoretical mz592.349
Error8.53
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.93

Identifiers and class information

Inchi keyMMMSPIBCDFEOIH-UHFFFAOYNA-N
SmilesO=C1NCC(O)C2=CC=C(OC(C(NC(=O)C(N(C)C)C(C)CC)C(=O)NC1CC3=CNC=4C=CC=CC43)C(C)C)C=C2
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

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)3
Number of rotatable bonds (#rotor)9
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)0
Molecular weight (mol_MW)591.749
Computed dipole moment(dipole)3.061
Total solvent accessible surface area (SASA)811.064
Hydrophobic component of SASA (FOSA)462.933
Hydrophilic component of SASA (FISA)104.255
Pie component of the SASA (PISA)243.876
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1707.18
Number of hydrogen bond donors (donorHB)3.5
Number of hydrogen bond acceptors (accptHB)10.45
Free energy of solvation of dipole (dip^2/V)0.005487
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0241043
Globularity descriptor (glob)0.85172
Predicted polarizability in cubic angstroms (QPpolrz)58.718
Predicted hexadecane/gas partition coefficient (QPlogPC16)16.939
Predicted octanol/gas partition coefficient (QPlogPoct)30.62
Predicted water/gas partition coefficient (QPlogPw)19.898
Predicted octanol/water partition coefficient (QPlogPo/w)2.523
Predicted aqueous solubility (QPlogS)-3.35
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.487
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-1.697
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)139.097
Predicted brain/blood partition coefficient (QPlogBB)-0.539
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)124.219
Predicted skin permeability, log Kp (QPlogKp)-3.78
PM3 calculated ionization potential (IP(ev))8.156
PM3 calculated electron affinity (EA(eV))-0.106
Number of likely metabolic reactions (#metab)6
Prediction of binding to human serum albumin (QPlogKhsa)-0.17
Predicted qualitative human oral absorption (HumanOralAbsorption)3
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)67.124
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)32.768
Van der Waals surface area (PSA)128.353
Number of nitrogen and oxygen atoms (#NandO)10
Number of violations of Lipinski’s rule of five (RuleOfFive)1
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
P00797RENReninT61622SwissTargetPrediction
O15379HDAC3Histone deacetylase 3T05090SEA
P08253MMP2Matrix metalloproteinase 2T68251SEA
P22894MMP8Matrix metalloproteinase 8T08856SEA
P14780MMP9Matrix metalloproteinase 9T54156SEA
P35372OPRM1Mu opioid receptorT47768SwissTargetPrediction
P35270SPRSubstance-P receptorT47094SwissTargetPrediction and SEA
P07711CTSLCathepsin LT98691SEA
P32245MC4RMelanocortin receptor 4T72458SEA
P07858CTSBCathepsin (B and K)T61746SEA
Q92847GHSRGhrelin receptorT59604SEA
Q01726MC1RMelanocortin receptor 1T35842SEA
P41968MC3RMelanocortin receptor 3T76846SEA
P42892ECE1Endothelin-converting enzyme 1T50970SEA
P25101EDNRAEndothelin receptor ET-AT23499SEA
P21730C5AR1C5a anaphylatoxin chemotactic receptorT15439SEA
P35346SSTR5Somatostatin receptor 5T64830SEA
P30874SSTR2Somatostatin receptor 2T53024SEA
P31391SSTR4Somatostatin receptor 4T62974SEA
P30872SSTR1Somatostatin receptor 1T16633SEA
P32745SSTR3Somatostatin receptor 3T13644SEA
P32239CCKBRCholecystokinin B receptor (by homology)T05849SEA
P24530EDNRBEndothelin receptor ET-BT92828SEA
P21452TACR2Neurokinin 2 receptorT52790SwissTargetPrediction and SEA
P28065PSMB9Proteasome subunit beta type-9T06792SEA
P51511MMP15Matrix metalloproteinase 15T81658SEA
P28336NMBRNeuromedin B receptorT68887SEA
P33032MC5RMelanocortin receptor 5T95302SEA
P28336NMBRNeuromedin B receptorT68887SEA
P30550GRPRGastrin releasing peptide receptorT99816SEA
Q9H2K8TAOK3Serine/threonine-protein kinase TAO3T63682SEA
P23284PPIBCyclophilin BT25847SEA
Q9BY41HDAC8Histone deacetylase 8T28887SEA
O95622ADCY5Adenylate cyclase type 5T19531SEA
Q9ULZ9MMP17Matrix metalloproteinase-17T55616SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T61622DI0190Hypertension[ICD-11: BA00-BA04]P00797REN
T05090DI0241Lymphoma[ICD-11: 2A80-2A86]O15379HDAC3
T05090DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O15379HDAC3
T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
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
T47768DI0013Acute pain[ICD-11: MG31]P35372OPRM1
T47768DI0059Bowel habit change[ICD-11: ME05]P35372OPRM1
T47768DI0087Chronic pain[ICD-11: MG30]P35372OPRM1
T47768DI0101Corneal disease[ICD-11: 9A76-9A78]P35372OPRM1
T47768DI0105Cough[ICD-11: MD12]P35372OPRM1
T47768DI0117Depression[ICD-11: 6A70-6A7Z]P35372OPRM1
T47768DI0124Digestive system disease[ICD-11: DE2Z]P35372OPRM1
T47768DI0218Irritable bowel syndrome[ICD-11: DD91]P35372OPRM1
T47768DI0228Large intestine motility disorder[ICD-11: DB32]P35372OPRM1
T47768DI0317Opioid use disorder[ICD-11: 6C43]P35372OPRM1
T47768DI0324Pain[ICD-11: MG30-MG3Z]P35372OPRM1
T47768DI0349Pruritus[ICD-11: EC90]P35372OPRM1
T47768DI0374Sensation disturbance[ICD-11: MB40]P35372OPRM1
T47094DI0117Depression[ICD-11: 6A70-6A7Z]P35270SPR
T47094DI0293Nausea/vomiting[ICD-11: MD90]P35270SPR
T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
T72458DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]P32245MC4R
T72458DI0228Large intestine motility disorder[ICD-11: DB32]P32245MC4R
T72458DI0308Obesity[ICD-11: 5B80-5B81]P32245MC4R
T61746DI0023Alopecia[ICD-11: ED70]P07858CTSB
T61746DI0025Alzheimer disease[ICD-11: 8A20]P07858CTSB
T61746DI0037Asthma[ICD-11: CA23]P07858CTSB
T61746DI0055Bone cancer[ICD-11: 2B5Z]P07858CTSB
T61746DI0060Brain cancer[ICD-11: 2A00]P07858CTSB
T61746DI0067Cardiac arrest[ICD-11: MC82]P07858CTSB
T61746DI0074Cerebral ischaemic stroke[ICD-11: 8B11]P07858CTSB
T61746DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P07858CTSB
T61746DI0087Chronic pain[ICD-11: MG30]P07858CTSB
T61746DI0110Cystic fibrosis[ICD-11: CA25]P07858CTSB
T61746DI0124Digestive system disease[ICD-11: DE2Z]P07858CTSB
T61746DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P07858CTSB
T61746DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P07858CTSB
T61746DI0253Meningioma[ICD-11: 2A01]P07858CTSB
T61746DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]P07858CTSB
T61746DI0275Multiple sclerosis[ICD-11: 8A40]P07858CTSB
T61746DI0296Neurodegenerative disorder[ICD-11: 8A20-8A23]P07858CTSB
T61746DI0320Osteoarthritis[ICD-11: FA00-FA05]P07858CTSB
T61746DI0351Psoriasis[ICD-11: EA90]P07858CTSB
T61746DI0366Rheumatoid arthritis[ICD-11: FA20]P07858CTSB
T59604DI0087Chronic pain[ICD-11: MG30]Q92847GHSR
T59604DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]Q92847GHSR
T35842DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]Q01726MC1R
T35842DI0205Inborn porphyrin/heme metabolism error[ICD-11: 5C58]Q01726MC1R
T76846DI0308Obesity[ICD-11: 5B80-5B81]P41968MC3R
T76846DI0378Sexual dysfunction[ICD-11: HA00-HA01]P41968MC3R
T76846DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P41968MC3R
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T15439DI0431Vasculitis[ICD-11: 4A44]P21730C5AR1
T64830DI0108Cushing syndrome[ICD-11: 5A70]P35346SSTR5
T53024DI0108Cushing syndrome[ICD-11: 5A70]P30874SSTR2
T53024DI0122Diagnostic imaging[ICD-11: N.A.]P30874SSTR2
T53024DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30874SSTR2
T62974DI0087Chronic pain[ICD-11: MG30]P31391SSTR4
T62974DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P31391SSTR4
T16633DI0108Cushing syndrome[ICD-11: 5A70]P30872SSTR1
T16633DI0395Stomach cancer[ICD-11: 2B72]P30872SSTR1
T13644DI0108Cushing syndrome[ICD-11: 5A70]P32745SSTR3
T05849DI0122Diagnostic imaging[ICD-11: N.A.]P32239CCKBR
T05849DI0327Pancreatic internal secretion disorder[ICD-11: 5A4Y]P32239CCKBR
T92828DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P24530EDNRB
T92828DI0356Pulmonary hypertension[ICD-11: BB01]P24530EDNRB
T52790DI0218Irritable bowel syndrome[ICD-11: DD91]P21452TACR2
T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
T95302DI0005Acne vulgaris[ICD-11: ED80]P33032MC5R
T95302DI0371Sebaceous gland disorder[ICD-11: ED91]P33032MC5R
T68887DI0062Breast cancer[ICD-11: 2C60-2C6Y]P28336NMBR
T68887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28336NMBR
T99816DI0062Breast cancer[ICD-11: 2C60-2C6Y]P30550GRPR
T99816DI0218Irritable bowel syndrome[ICD-11: DD91]P30550GRPR
T99816DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P30550GRPR
T25847DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P23284PPIB
T28887DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9BY41HDAC8

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