Lyciumin C



Compound IDCDAMM02034
Common nameLyciumin C
IUPAC name8-benzyl-11-(hydroxymethyl)-2-[[3-(4-hydroxyphenyl)-2-[[1-(5-oxopyrrolidine-2-carbonyl)pyrrolidine-2-carbonyl]amino]propanoyl]amino]-3,6,9,12-tetraoxo-5-propan-2-yl-1,4,7,10,13-pentazatricyclo[14.6.1.017,22]tricosa-16(23),17,19,21-tetraene-14-carboxylic acid
Molecular formulaC49H57N9O12

Experimental data

Retention time16.65
Adduct[M+H]+
Actual mz964.413
Theoretical mz964.42
Error7.54
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.3895

Identifiers and class information

Inchi keyJJVYOOBAXDVVNT-UHFFFAOYNA-N
SmilesO=C(O)C1NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C2N(C(=O)C3NC(=O)CC3)CCC2)CC4=CC=C(O)C=C4)N5C=C(C=6C=CC=CC65)C1)C(C)C)CC=7C=CC=CC7)CO
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)13
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)1
Number of non-conjugated amide groups (#amide)8
Number of rotatable bonds (#rotor)25
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)964.042
Computed dipole moment(dipole)14.479
Total solvent accessible surface area (SASA)1195.43
Hydrophobic component of SASA (FOSA)434.175
Hydrophilic component of SASA (FISA)371.872
Pie component of the SASA (PISA)389.384
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)2578.98
Number of hydrogen bond donors (donorHB)3.75
Number of hydrogen bond acceptors (accptHB)18.7
Free energy of solvation of dipole (dip^2/V)0.0812936
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0302923
Globularity descriptor (glob)0.760803
Predicted polarizability in cubic angstroms (QPpolrz)84.723
Predicted hexadecane/gas partition coefficient (QPlogPC16)27.847
Predicted octanol/gas partition coefficient (QPlogPoct)46.583
Predicted water/gas partition coefficient (QPlogPw)37.944
Predicted octanol/water partition coefficient (QPlogPo/w)0.626
Predicted aqueous solubility (QPlogS)-1.266
Conformation-independent predicted aqueous solubility (CIQPlogS)-7.299
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)5.543
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.04
Predicted brain/blood partition coefficient (QPlogBB)-5.226
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.262
Predicted skin permeability, log Kp (QPlogKp)-4.601
PM3 calculated ionization potential (IP(ev))8.741
PM3 calculated electron affinity (EA(eV))0.387
Number of likely metabolic reactions (#metab)14
Prediction of binding to human serum albumin (QPlogKhsa)-2.073
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)159.086
Van der Waals surface area (PSA)348.03
Number of nitrogen and oxygen atoms (#NandO)21
Number of violations of Lipinski’s rule of five (RuleOfFive)3
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
P00797RENReninT61622SEA
P15144ANPEPAminopeptidase NT67272SEA
P00734F2ThrombinT94033SEA
P98170XIAPInhibitor of apoptosis protein 3T16769SEA
P12955PEPDXaa-Pro dipeptidaseT94823SEA
P35372OPRM1Mu opioid receptorT47768SEA
P35270SPRSubstance-P receptorT47094SEA
P30559OXTROxytocin receptor (by homology)T84486SEA
P37288AVPR1AVasopressin V1a receptor (by homology)T79232SEA
P34981TRHRThyrotropin-releasing hormone receptorT77796SEA
P30518AVPR2Vasopressin V2 receptor (by homology)T66237SEA
P32245MC4RMelanocortin receptor 4T72458SEA
P41143OPRD1Delta opioid receptorT58992SEA
Q01726MC1RMelanocortin receptor 1T35842SEA
P41968MC3RMelanocortin receptor 3T76846SEA
P23946CMA1ChymaseT05114SEA
Q13489BIRC3Baculoviral IAP repeat-containing protein 3T35173SEA
O43193MLNRMotilin receptorT62306SEA
P04035HMGCRHMG-CoA reductaseT53585SEA
P04439HLA-AHLA class I histocompatibility antigen A-3T08985SEA
P05556ITGB1Integrin alpha2/beta1T01851SEA
P21730C5AR1C5a anaphylatoxin chemotactic receptorT15439SEA
P35346SSTR5Somatostatin receptor 5T64830SEA
P30874SSTR2Somatostatin receptor 2T53024SEA
P31391SSTR4Somatostatin receptor 4T62974SEA
P30872SSTR1Somatostatin receptor 1T16633SEA
Q99895CTRCChymotrypsin CT10118SEA
P50052AGTR2Angiotensin II receptorT09909SEA
P30989NTSR1Neurotensin receptor 1T02728SEA
Q16581C3AR1C3a anaphylatoxin chemotactic receptorT30219SEA
P26010ITGB7Integrin alpha-4/beta-7T07403SEA
Q9UKP6UTS2RUrotensin II receptorT49072SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P42226STAT6Signal transducer and activator of transcription 6T20585SEA
Q9UIQ6LNPEPCystinyl aminopeptidaseT97537SEA
Q9UNI1CELA1Elastase 1T22839SEA
P62937PPIACyclophilin AT47081SEA
Q96DB2HDAC11Histone deacetylase 11T97903SEA
P47901AVPR1BVasopressin V1b receptorT59881SEA
Q13451FKBP5Peptidyl-prolyl cis-trans isomerase FKBP5T98337SEA
Q969S8HDAC10Histone deacetylase 10T94324SEA
P13612ITGA4Integrin alpha-4T97587SEA
Q9Y337KLK5Kallikrein 5T11808SEA
P08311CTSGCathepsin GT86385SEA
P15169CPN1Carboxypeptidase N, catalytic subunitT34471SEA
O43895XPNPEP2Xaa-Pro aminopeptidase 2T68320SEA
O60235TMPRSS11DTransmembrane protease serine 11DT00302SEA
P22735TGM1Protein-glutamine gamma-glutamyltransferase KT63217SEA
Q9GZQ6NPFFR1Neuropeptide FF receptor 1T79780SEA
Q9Y5X5NPFFR2Neuropeptide FF receptor 2T90818SEA
O95665NTSR2Neurotensin receptor type 2T95605SEA
Q9HB89NMUR1Neuromedin-U receptor 1T83382SEA
Q9UHJ5PRLRProlactin receptorT26226SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T61622DI0190Hypertension[ICD-11: BA00-BA04]P00797REN
T67272DI0351Psoriasis[ICD-11: EA90]P15144ANPEP
T94033DI0052Bleeding disorder[ICD-11: GA20-GA21]P00734F2
T94033DI0091Coagulation defect[ICD-11: 3B10]P00734F2
T94033DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P00734F2
T94033DI0275Multiple sclerosis[ICD-11: 8A40]P00734F2
T94033DI0287Myocardial infarction[ICD-11: BA41-BA43]P00734F2
T94033DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P00734F2
T94033DI0403Thrombocytopenia[ICD-11: 3B64]P00734F2
T94033DI0405Thrombosis[ICD-11: DB61-GB90]P00734F2
T16769DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]P98170XIAP
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
T84486DI0009Acute diabete complication[ICD-11: 5A2Y]P30559OXTR
T84486DI0041Autism spectrum disorder[ICD-11: 6A02]P30559OXTR
T84486DI0340Postpartum haemorrhage[ICD-11: JA43]P30559OXTR
T79232DI0009Acute diabete complication[ICD-11: 5A2Y]P37288AVPR1A
T79232DI0041Autism spectrum disorder[ICD-11: 6A02]P37288AVPR1A
T79232DI0190Hypertension[ICD-11: BA00-BA04]P37288AVPR1A
T79232DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P37288AVPR1A
T79232DI0236Localisation[ICD-11: N.A.]P37288AVPR1A
T77796DI0072Central nervous system disease[ICD-11: 8A04-8D87]P34981TRHR
T66237DI0009Acute diabete complication[ICD-11: 5A2Y]P30518AVPR2
T66237DI0041Autism spectrum disorder[ICD-11: 6A02]P30518AVPR2
T66237DI0131Enuresis[ICD-11: 6C00]P30518AVPR2
T66237DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P30518AVPR2
T66237DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30518AVPR2
T66237DI0338Polyuria[ICD-11: MF55]P30518AVPR2
T72458DI0192Hypoactive sexual desire dysfunction[ICD-11: HA00]P32245MC4R
T72458DI0228Large intestine motility disorder[ICD-11: DB32]P32245MC4R
T72458DI0308Obesity[ICD-11: 5B80-5B81]P32245MC4R
T58992DI0059Bowel habit change[ICD-11: ME05]P41143OPRD1
T58992DI0218Irritable bowel syndrome[ICD-11: DD91]P41143OPRD1
T58992DI0324Pain[ICD-11: MG30-MG3Z]P41143OPRD1
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
T05114DI0039Atopic eczema[ICD-11: EA80]P23946CMA1
T05114DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P23946CMA1
T05114DI0169Gram-positive bacterial infection[ICD-11: 1B74-1F40]P23946CMA1
T05114DI0175Heart failure[ICD-11: BD10-BD1Z]P23946CMA1
T05114DI0229Left ventricular failure[ICD-11: BD11]P23946CMA1
T05114DI0287Myocardial infarction[ICD-11: BA41-BA43]P23946CMA1
T35173DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]Q13489BIRC3
T62306DI0124Digestive system disease[ICD-11: DE2Z]O43193MLNR
T62306DI0159Gastroduodenal motor/secretory disorder[ICD-11: DA41]O43193MLNR
T62306DI0161Gastro-oesophageal reflux disease[ICD-11: DA22]O43193MLNR
T62306DI0218Irritable bowel syndrome[ICD-11: DD91]O43193MLNR
T62306DI0324Pain[ICD-11: MG30-MG3Z]O43193MLNR
T53585DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P04035HMGCR
T53585DI0102Coronary atherosclerosis[ICD-11: BA52]P04035HMGCR
T53585DI0128Dyslipidemia[ICD-11: 5C80-5C81]P04035HMGCR
T53585DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P04035HMGCR
T53585DI0275Multiple sclerosis[ICD-11: 8A40]P04035HMGCR
T53585DI0287Myocardial infarction[ICD-11: BA41-BA43]P04035HMGCR
T53585DI0324Pain[ICD-11: MG30-MG3Z]P04035HMGCR
T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
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
T09909DI0190Hypertension[ICD-11: BA00-BA04]P50052AGTR2
T09909DI0373Secondary hypertension[ICD-11: BA04]P50052AGTR2
T02728DI0207Indeterminate colitis[ICD-11: DD72]P30989NTSR1
T07403DI0107Crohn disease[ICD-11: DD70]P26010ITGB7
T49072DI0037Asthma[ICD-11: CA23]Q9UKP6UTS2R
T22839DI0024Alpha-1-antitrypsin deficiency[ICD-11: 5C5A]Q9UNI1CELA1
T22839DI0065Bronchitis[ICD-11: CA20]Q9UNI1CELA1
T47081DI0306Nutritional deficiency[ICD-11: 5B50-5B71]P62937PPIA
T59881DI0009Acute diabete complication[ICD-11: 5A2Y]P47901AVPR1B
T59881DI0041Autism spectrum disorder[ICD-11: 6A02]P47901AVPR1B
T59881DI0194Hypo-osmolality/hyponatraemia[ICD-11: 5C72]P47901AVPR1B
T94324DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q969S8HDAC10
T97587DI0107Crohn disease[ICD-11: DD70]P13612ITGA4
T97587DI0275Multiple sclerosis[ICD-11: 8A40]P13612ITGA4
T97587DI0419Ulcerative colitis[ICD-11: DD71]P13612ITGA4
T86385DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P08311CTSG
T63217DI0045Autosomal Recessive Ichthyosis[ICD-11: EC20]P22735TGM1
T26226DI0143Fallopian tube cancer[ICD-11: 2C74]Q9UHJ5PRLR
T26226DI0321Ovarian cancer[ICD-11: 2C73]Q9UHJ5PRLR
T26226DI0334Peritoneal cancer[ICD-11: 2C51]Q9UHJ5PRLR
T26226DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UHJ5PRLR

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