Dehydrophytosphingosine



Compound IDCDAMM00265
Common nameDehydrophytosphingosine
IUPAC name(E,2S,3S,4R)-2-aminooctadec-8-ene-1,3,4-triol
Molecular formulaC18H37NO3

Experimental data

Retention time56.422
Adduct[M+H]+
Actual mz316.287
Theoretical mz316.285
Error7.2
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.45

Identifiers and class information

Inchi keySKOLRLSBMUGVOY-GBJTYRQASA-N
SmilesCCCCCCCCCC=CCCCC(C(C(CO)N)O)O
SuperclassAlkaloids and derivatives
ClassLupin alkaloids

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)19
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)315.495
Computed dipole moment(dipole)5.123
Total solvent accessible surface area (SASA)744.577
Hydrophobic component of SASA (FOSA)559.863
Hydrophilic component of SASA (FISA)171.242
Pie component of the SASA (PISA)13.471
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1282.4
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)6.1
Free energy of solvation of dipole (dip^2/V)0.0204652
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0183192
Globularity descriptor (glob)0.766664
Predicted polarizability in cubic angstroms (QPpolrz)33.097
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.731
Predicted octanol/gas partition coefficient (QPlogPoct)20.725
Predicted water/gas partition coefficient (QPlogPw)11.908
Predicted octanol/water partition coefficient (QPlogPo/w)2.308
Predicted aqueous solubility (QPlogS)-2.643
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.926
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.098
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)58.737
Predicted brain/blood partition coefficient (QPlogBB)-2.125
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)25.56
Predicted skin permeability, log Kp (QPlogKp)-4.866
PM3 calculated ionization potential (IP(ev))9.116
PM3 calculated electron affinity (EA(eV))-0.854
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-0.227
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)72.117
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)89.223
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)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P34913EPHX2Epoxide hydrataseT35734SEA
P08908HTR1ASerotonin 1a (5-HT1a) receptorT78709SwissTargetPrediction
O00519FAAHAnandamide amidohydrolaseT11754SEA
Q9NYA1SPHK1Sphingosine kinase 1T86014SwissTargetPrediction
P07550ADRB2Adrenergic receptor betaT52522SwissTargetPrediction
P05093CYP17A1Cytochrome P450 17A1T89041SwissTargetPrediction
P00813ADAAdenosine deaminaseT03661SEA
Q8TDS5OXER1Oxoeicosanoid receptor 1T68834SEA
Q9H228S1PR5Sphingosine 1-phosphate receptor Edg-8T50089SwissTargetPrediction
P21453S1PR1Sphingosine 1-phosphate receptor Edg-1T13852SwissTargetPrediction
P32418SLC8A1Sodium/calcium exchanger 1T07775SwissTargetPrediction
Q9NRA0SPHK2Sphingosine kinase 2T31989SEA
Q9HBW0LPAR2Lysophosphatidic acid receptor Edg-4T39380SwissTargetPrediction and SEA
Q99500S1PR3Sphingosine 1-phosphate receptor Edg-3T11241SwissTargetPrediction
P43657LPAR6Lysophosphatidic acid receptor 6T13484SEA
O95136S1PR2Sphingosine 1-phosphate receptor Edg-5T47888SwissTargetPrediction and SEA
O95977S1PR4Sphingosine 1-phosphate receptor Edg-6T17523SwissTargetPrediction and SEA
Q9UPC5GPR34Probable G-protein coupled receptor 34T73859SEA
O00398P2RY10Putative P2Y purinoceptor 10T00488SEA
Q9BXC1GPR174Probable G-protein coupled receptor 174T87661SEA
Q9UBY5LPAR3Lysophosphatidic acid receptor Edg-7T95923SEA
Q92633LPAR1Lysophosphatidic acid receptor Edg-2T92640SEA
Q99677LPAR4Lysophosphatidic acid receptor 4T58130SEA
O95470SGPL1Sphingosine-1-phosphate lyase 1T01575SwissTargetPrediction
Q9UP65PLA2G4CCytosolic phospholipase A2 gammaT91113SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
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
T11754DI0101Corneal disease[ICD-11: 9A76-9A78]O00519FAAH
T86014DI0321Ovarian cancer[ICD-11: 2C73]Q9NYA1SPHK1
T86014DI0353Psychoactive substances use disorder[ICD-11: 6C4G]Q9NYA1SPHK1
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
T89041DI0346Prostate cancer[ICD-11: 2C82]P05093CYP17A1
T03661DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P00813ADA
T03661DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00813ADA
T03661DI0249Mature B-cell leukaemia[ICD-11: 2A82]P00813ADA
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
T47888DI0419Ulcerative colitis[ICD-11: DD71]O95136S1PR2
T95923DI0146Fibrosis[ICD-11: GA14-GC01]Q9UBY5LPAR3
T95923DI0399Systemic sclerosis[ICD-11: 4A42]Q9UBY5LPAR3
T92640DI0146Fibrosis[ICD-11: GA14-GC01]Q92633LPAR1
T92640DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]Q92633LPAR1
T92640DI0351Psoriasis[ICD-11: EA90]Q92633LPAR1
T92640DI0399Systemic sclerosis[ICD-11: 4A42]Q92633LPAR1
T01575DI0098Congenital ichthyosis[ICD-11: EC20]O95470SGPL1
T01575DI0366Rheumatoid arthritis[ICD-11: FA20]O95470SGPL1

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