C16 phytosphingosine



Compound IDCDAMM00355
Common nameC16 phytosphingosine
IUPAC name(2S,3S,4R)-2-aminohexadecane-1,3,4-triol
Molecular formulaC16H35NO3

Experimental data

Retention time55.722
Adduct[M+H]+
Actual mz290.272
Theoretical mz290.269
Error11.36
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.51

Identifiers and class information

Inchi keyOCHZTELGZBWSJD-YUWMZDKKNA-N
SmilesOCC(N)C(O)C(O)CCCCCCCCCCCC
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds

Pharmacokinetic properties

Number of descriptor values(#stars)2
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)18
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)289.457
Computed dipole moment(dipole)5.328
Total solvent accessible surface area (SASA)691.447
Hydrophobic component of SASA (FOSA)521.817
Hydrophilic component of SASA (FISA)169.63
Pie component of the SASA (PISA)0
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1177.97
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)6.1
Free energy of solvation of dipole (dip^2/V)0.0241011
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0197268
Globularity descriptor (glob)0.780121
Predicted polarizability in cubic angstroms (QPpolrz)29.43
Predicted hexadecane/gas partition coefficient (QPlogPC16)11.545
Predicted octanol/gas partition coefficient (QPlogPoct)19.534
Predicted water/gas partition coefficient (QPlogPw)11.898
Predicted octanol/water partition coefficient (QPlogPo/w)1.684
Predicted aqueous solubility (QPlogS)-1.94
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.468
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.816
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)60.841
Predicted brain/blood partition coefficient (QPlogBB)-1.981
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)26.552
Predicted skin permeability, log Kp (QPlogKp)-4.98
PM3 calculated ionization potential (IP(ev))9.102
PM3 calculated electron affinity (EA(eV))-2.328
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)-0.427
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)68.739
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)88.806
Number of nitrogen and oxygen atoms (#NandO)4
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
P43681CHRNA4Neuronal acetylcholine receptor; alpha4/beta2T70967SwissTargetPrediction
Q9Y5N1HRH3Histamine H3 receptorT64765SwissTargetPrediction
P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
P22303ACHEAcetylcholinesteraseT30082SwissTargetPrediction
Q12809KCNH2HERGT20251SwissTargetPrediction
P07327ADH1AAlcohol dehydrogenase alpha chainT65570SEA
P29475NOS1Nitric-oxide synthase, brainT16117SwissTargetPrediction
P09874PARP1Poly [ADP-ribose] polymerase-1T06273SwissTargetPrediction
P14416DRD2Dopamine D2 receptorT67162SwissTargetPrediction
O43451MGAMMaltase-glucoamylaseT92777SwissTargetPrediction
P10253GAALysosomal alpha-glucosidase (by homology)T31514SwissTargetPrediction
P27487DPP4Dipeptidyl peptidase IVT31391SwissTargetPrediction
P28223HTR2ASerotonin 2a (5-HT2a) receptorT32060SwissTargetPrediction
P31645SLC6A4Serotonin transporter (by homology)T27812SwissTargetPrediction
P08588ADRB1Beta-1 adrenergic receptorT44068SwissTargetPrediction
P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SwissTargetPrediction
P50406HTR6Serotonin 6 (5-HT6) receptorT16691SwissTargetPrediction
P43235CTSKCathepsin KT11388SwissTargetPrediction
Q9NYA1SPHK1Sphingosine kinase 1T86014SwissTargetPrediction
Q6QHF9PAOXPolyamine oxidaseT88699SwissTargetPrediction
P35462DRD3Dopamine D3 receptorT02551SwissTargetPrediction
P07550ADRB2Adrenergic receptor betaT52522SwissTargetPrediction
P13945ADRB3Beta-3 adrenergic receptorT51408SwissTargetPrediction
Q13639HTR4Serotonin 4 (5-HT4) receptorT59679SwissTargetPrediction
P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
O14757CHEK1Serine/threonine-protein kinase Chk1T62449SwissTargetPrediction
Q9P1W9PIM2Serine/threonine-protein kinase PIM2T07279SwissTargetPrediction
Q86V86PIM3Serine/threonine-protein kinase PIM3T16596SwissTargetPrediction
O14965AURKASerine/threonine-protein kinase Aurora-AT87675SwissTargetPrediction
O75116ROCK2Rho-associated protein kinase 2T06093SwissTargetPrediction
P41743PRKCIProtein kinase C iotaT83174SwissTargetPrediction
P12931SRCTyrosine-protein kinase SRCT85943SwissTargetPrediction
P00813ADAAdenosine deaminaseT03661SEA
P0DJD9PGA5Pepsin AT17863SEA
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
P23443RPS6KB1Ribosomal protein S6 kinase 1T94479SwissTargetPrediction
P50750CDK9Cyclin-dependent kinase 9T44458SwissTargetPrediction
P46098HTR3ASerotonin 3a (5-HT3a) receptorT64591SwissTargetPrediction
Q9H228S1PR5Sphingosine 1-phosphate receptor Edg-8T50089SwissTargetPrediction
P21453S1PR1Sphingosine 1-phosphate receptor Edg-1T13852SwissTargetPrediction
P41240CSKTyrosine-protein kinase CSKT08741SwissTargetPrediction
Q9NRA0SPHK2Sphingosine kinase 2T31989SwissTargetPrediction and SEA
Q9HBW0LPAR2Lysophosphatidic acid receptor Edg-4T39380SwissTargetPrediction
Q99500S1PR3Sphingosine 1-phosphate receptor Edg-3T11241SwissTargetPrediction and SEA
P53634CTSCDipeptidyl peptidase IT70490SwissTargetPrediction
O95136S1PR2Sphingosine 1-phosphate receptor Edg-5T47888SwissTargetPrediction and SEA
P48048KCNJ1ATP-sensitive inward rectifier potassium channel 1T78710SwissTargetPrediction
O95977S1PR4Sphingosine 1-phosphate receptor Edg-6T17523SwissTargetPrediction and SEA
Q8IWU9TPH2Tryptophan hydroxylaseT51593SwissTargetPrediction
O14786NRP1Neuropilin-1 (by homology)T15023SwissTargetPrediction
O95749GGPS1GeranyltranstransferaseT86528SEA

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
T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
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
T65570DI0139Exposure to noxious substances harmful effect[ICD-11: NE61]P07327ADH1A
T16117DI0173Headache[ICD-11: 8A80-8A84]P29475NOS1
T16117DI0264Migraine[ICD-11: 8A80]P29475NOS1
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
T67162DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P14416DRD2
T67162DI0025Alzheimer disease[ICD-11: 8A20]P14416DRD2
T67162DI0037Asthma[ICD-11: CA23]P14416DRD2
T67162DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P14416DRD2
T67162DI0051Bipolar disorder[ICD-11: 6A60]P14416DRD2
T67162DI0063Breathing abnormality[ICD-11: MD11]P14416DRD2
T67162DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P14416DRD2
T67162DI0073Cerebral ischaemia[ICD-11: 8B1Z]P14416DRD2
T67162DI0117Depression[ICD-11: 6A70-6A7Z]P14416DRD2
T67162DI0124Digestive system disease[ICD-11: DE2Z]P14416DRD2
T67162DI0137Essential hypertension[ICD-11: BA00]P14416DRD2
T67162DI0142Faecal incontinence[ICD-11: ME07]P14416DRD2
T67162DI0156Gangrene[ICD-11: MC85]P14416DRD2
T67162DI0166Glaucoma[ICD-11: 9C61]P14416DRD2
T67162DI0175Heart failure[ICD-11: BD10-BD1Z]P14416DRD2
T67162DI0185Hyperaemia[ICD-11: 9A61-9B7Y]P14416DRD2
T67162DI0190Hypertension[ICD-11: BA00-BA04]P14416DRD2
T67162DI0196Hypotension[ICD-11: BA20-BA21]P14416DRD2
T67162DI0205Inborn porphyrin/heme metabolism error[ICD-11: 5C58]P14416DRD2
T67162DI0214Insomnia[ICD-11: 7A00-7A0Z]P14416DRD2
T67162DI0222Itching[ICD-11: 1F28-1G07]P14416DRD2
T67162DI0264Migraine[ICD-11: 8A80]P14416DRD2
T67162DI0293Nausea/vomiting[ICD-11: MD90]P14416DRD2
T67162DI0324Pain[ICD-11: MG30-MG3Z]P14416DRD2
T67162DI0331Parkinsonism[ICD-11: 8A00]P14416DRD2
T67162DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P14416DRD2
T67162DI0340Postpartum haemorrhage[ICD-11: JA43]P14416DRD2
T67162DI0354Psychotic disorder[ICD-11: 6A20-6A25]P14416DRD2
T67162DI0356Pulmonary hypertension[ICD-11: BB01]P14416DRD2
T67162DI0370Schizophrenia[ICD-11: 6A20]P14416DRD2
T67162DI0396Substance abuse[ICD-11: 6C40]P14416DRD2
T67162DI0408Thyrotoxicosis[ICD-11: 5A02]P14416DRD2
T67162DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P14416DRD2
T92777DI0009Acute diabete complication[ICD-11: 5A2Y]O43451MGAM
T92777DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]O43451MGAM
T31514DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]P10253GAA
T31391DI0009Acute diabete complication[ICD-11: 5A2Y]P27487DPP4
T31391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P27487DPP4
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
T27812DI0033Anxiety disorder[ICD-11: 6B00-6B0Z]P31645SLC6A4
T27812DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P31645SLC6A4
T27812DI0087Chronic pain[ICD-11: MG30]P31645SLC6A4
T27812DI0096concerning food/fluid intake symptom[ICD-11: MG43]P31645SLC6A4
T27812DI0101Corneal disease[ICD-11: 9A76-9A78]P31645SLC6A4
T27812DI0105Cough[ICD-11: MD12]P31645SLC6A4
T27812DI0117Depression[ICD-11: 6A70-6A7Z]P31645SLC6A4
T27812DI0264Migraine[ICD-11: 8A80]P31645SLC6A4
T27812DI0301Nicotine use disorder[ICD-11: 6C4A]P31645SLC6A4
T27812DI0308Obesity[ICD-11: 5B80-5B81]P31645SLC6A4
T27812DI0324Pain[ICD-11: MG30-MG3Z]P31645SLC6A4
T44068DI0022Allergic/hypersensitivity disorder[ICD-11: 4A80-4A8Z]P08588ADRB1
T44068DI0037Asthma[ICD-11: CA23]P08588ADRB1
T44068DI0068Cardiac arrhythmia[ICD-11: BC9Z]P08588ADRB1
T44068DI0071Central and peripheral nervous disease[ICD-11: 8A04-8E7Z]P08588ADRB1
T44068DI0088Circulatory system disease[ICD-11: BE2Z]P08588ADRB1
T44068DI0097Conduction disorder[ICD-11: BC63]P08588ADRB1
T44068DI0102Coronary atherosclerosis[ICD-11: BA52]P08588ADRB1
T44068DI0137Essential hypertension[ICD-11: BA00]P08588ADRB1
T44068DI0166Glaucoma[ICD-11: 9C61]P08588ADRB1
T44068DI0175Heart failure[ICD-11: BD10-BD1Z]P08588ADRB1
T44068DI0190Hypertension[ICD-11: BA00-BA04]P08588ADRB1
T44068DI0264Migraine[ICD-11: 8A80]P08588ADRB1
T44068DI0375Sepsis[ICD-11: 1G40-1G41]P08588ADRB1
T44068DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P08588ADRB1
T44068DI0434Ventricular tachyarrhythmia[ICD-11: BC71]P08588ADRB1
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
T16691DI0025Alzheimer disease[ICD-11: 8A20]P50406HTR6
T16691DI0370Schizophrenia[ICD-11: 6A20]P50406HTR6
T11388DI0237Low bone mass disorder[ICD-11: FB83]P43235CTSK
T86014DI0321Ovarian cancer[ICD-11: 2C73]Q9NYA1SPHK1
T86014DI0353Psychoactive substances use disorder[ICD-11: 6C4G]Q9NYA1SPHK1
T02551DI0051Bipolar disorder[ICD-11: 6A60]P35462DRD3
T02551DI0331Parkinsonism[ICD-11: 8A00]P35462DRD3
T52522DI0037Asthma[ICD-11: CA23]P07550ADRB2
T52522DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P07550ADRB2
T52522DI0097Conduction disorder[ICD-11: BC63]P07550ADRB2
T52522DI0344Preterm labour/delivery[ICD-11: JB00]P07550ADRB2
T52522DI0387Sleep-related breathing disorder[ICD-11: 7A4Z]P07550ADRB2
T51408DI0030Angina pectoris[ICD-11: BA40]P13945ADRB3
T51408DI0037Asthma[ICD-11: CA23]P13945ADRB3
T51408DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P13945ADRB3
T51408DI0129Dystonic disorder[ICD-11: 8A02]P13945ADRB3
T51408DI0154Functional bladder disorder[ICD-11: GC50]P13945ADRB3
T51408DI0190Hypertension[ICD-11: BA00-BA04]P13945ADRB3
T51408DI0331Parkinsonism[ICD-11: 8A00]P13945ADRB3
T59679DI0161Gastro-oesophageal reflux disease[ICD-11: DA22]Q13639HTR4
T59679DI0218Irritable bowel syndrome[ICD-11: DD91]Q13639HTR4
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
T07279DI0274Multiple myeloma[ICD-11: 2A83]Q9P1W9PIM2
T07279DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9P1W9PIM2
T87675DI0009Acute diabete complication[ICD-11: 5A2Y]O14965AURKA
T87675DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O14965AURKA
T06093DI0168Graft-versus-host disease[ICD-11: 4B24]O75116ROCK2
T83174DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P41743PRKCI
T85943DI0062Breast cancer[ICD-11: 2C60-2C6Y]P12931SRC
T85943DI0220Ischemia[ICD-11: 8B10-8B11]P12931SRC
T85943DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P12931SRC
T85943DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P12931SRC
T03661DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P00813ADA
T03661DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00813ADA
T03661DI0249Mature B-cell leukaemia[ICD-11: 2A82]P00813ADA
T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
T94479DI0025Alzheimer disease[ICD-11: 8A20]P23443RPS6KB1
T94479DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P23443RPS6KB1
T94479DI0419Ulcerative colitis[ICD-11: DD71]P23443RPS6KB1
T44458DI0012Acute myeloid leukaemia[ICD-11: 2A60]P50750CDK9
T44458DI0241Lymphoma[ICD-11: 2A80-2A86]P50750CDK9
T44458DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P50750CDK9
T44458DI0249Mature B-cell leukaemia[ICD-11: 2A82]P50750CDK9
T44458DI0250Mature B-cell lymphoma[ICD-11: 2A85]P50750CDK9
T44458DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P50750CDK9
T44458DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P50750CDK9
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
T50089DI0275Multiple sclerosis[ICD-11: 8A40]Q9H228S1PR5
T13852DI0275Multiple sclerosis[ICD-11: 8A40]P21453S1PR1
T13852DI0419Ulcerative colitis[ICD-11: DD71]P21453S1PR1
T31989DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9NRA0SPHK2
T11241DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q99500S1PR3
T70490DI0064Bronchiectasis[ICD-11: CA24]P53634CTSC
T47888DI0419Ulcerative colitis[ICD-11: DD71]O95136S1PR2
T51593DI0066Carcinoid syndrome[ICD-11: 5B10]Q8IWU9TPH2
T51593DI0389Small intestine developmental anomaly[ICD-11: DA90]Q8IWU9TPH2
T15023DI0365Retinopathy[ICD-11: 9B71]O14786NRP1
T86528DI0057Bone paget disease[ICD-11: FB85]O95749GGPS1
T86528DI0237Low bone mass disorder[ICD-11: FB83]O95749GGPS1
T86528DI0267Mineral excesses[ICD-11: 5B91]O95749GGPS1
T86528DI0281Musculoskeletal disorder[ICD-11: FA00-FC0Z]O95749GGPS1

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