Natural Product (NP) Details

General Information of the NP (ID: NP9846)
Name
Phytosphingosine
Synonyms
phytosphingosine; 554-62-1; (2S,3S,4R)-2-aminooctadecane-1,3,4-triol; 4-D-Hydroxysphinganine; D-Ribo-phytosphingosine; C18-Phytosphingosine; UNII-GIN46U9Q2Q; 4R-hydroxysphinganine; GIN46U9Q2Q; 1,3,4-Octadecanetriol, 2-amino-, (2S,3S,4R)-; (+)-D-ribo-Phytosphingosine; 4-R-hydroxyoctadecasphinganine; CHEBI:46961; 4-hydroxysphinganine; D-Ribo-1,3,4-trihydroxy-2-aminooctadecane; Phytosphingosin; C18H39NO3; DS-phytosphingosine; phytosphingosine group; 4D-Hydroxysphinganine; 4-D-hydroxy-Sphinganine; EC 439-210-6; SCHEMBL20110; C18-PHS; CHEMBL236036; DTXSID80203951; ZINC8437018; 5544AE; ANW-32318; LMSP01030001; MFCD02259274; AKOS015949172; AKOS016015084; CCG-208251; CS-W012019; DB14119; FS-5977; HY-W011303; D-ribo-2-amino-1,3,4-Octadecanetriol; SMP2_000142; NCGC00163609-01; P1765; (2S,3S,4R)-2-Amino-1,3,4-octadecanetriol; C12144; SR-05000002328; J-501034; Q3746193; SR-05000002328-2; (2S,3S,4R)-2-Amino-1,3,4-octadecanetriol, AldrichCPR; [2S-(2R*,3R*,4S*)]-2-amino-1,3,4-Octadecanetriol; 1,3,4-Octadecanetriol, 2-amino-, (2S-(2R*,3R*,4S*))-; D-ribo-Phytosphingosine, 4-hydroxysphinganine (Saccharomyces Cerevisiae), powder
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Species Origin Patiria pectinifera ...     Click to Show/Hide
Patiria pectinifera
Kingdom: Metazoa
Phylum: Echinodermata
Class: Asteroidea
Order: Valvatida
Family: Asterinidae
Genus: Patiria
Species: Patiria pectinifera
Disease Skin inflammation [ICD-11: ME66] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.12
 
MDCK Permeability
 -4.818
 
PAMPA
 - -
 
HIA
 - -
 
Distribution
VDss
 0.723
 
PPB
 97.6%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 ++
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 +++
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 - - -
 
Excretion
CLplasma
 4.581
 
T1/2
 0.975
Toxicity
DILI
 - - -
 
Rat Oral Acute Toxicity
 - -
 
FDAMDD
 - - -
 
Respiratory
 ++
 
Human Hepatotoxicity
 +
 
Ototoxicity
 ++
 
Drug-induced Nephrotoxicity
 -
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - -
 
Genotoxicity
 - - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C18H39NO3
PubChem CID
122121
Canonical SMILES
CCCCCCCCCCCCCCC(C(C(CO)N)O)O
InChI
1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1
InChIKey
AERBNCYCJBRYDG-KSZLIROESA-N
CAS Number
CAS 554-62-1
ChEBI ID
CHEBI:46961
Herb ID
HBIN039807
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Gamma-ray irradiation      Brain metastases     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression PARP1  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Induction AIF nuclear translocation
Induction Bax mitochondrial relocalization
Induction ROS accumulation
                    In-vitro Model Jurkat CVCL_0065 T acute lymphoblastic leukemia Homo sapiens
                    Experimental
                    Result(s)		 Enhancement of cell death of radiation-resistant cancer cells by phytosphingosine treatment in combination with gamma-radiation is mediated by nuclear translocation of AIF, which is in turn mediated both by ROS-dependent Bax relocalization and ROS-independent PARP-1 activation.
          TNF-related apoptosis inducing ligand      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression TRAIL-R1  Molecule Info 
Pathway MAP
Up-regulation Expression TRAIL-R2  Molecule Info 
Pathway MAP
                    In-vitro Model Jurkat CVCL_0065 T acute lymphoblastic leukemia Homo sapiens
                    Experimental
                    Result(s)		 Phytosphingosine sensitizes cancer cells to TRAIL through the synergistic up-regulation of DR4 and DR5 in an NF-kappaB-dependent fashion resulting in caspase-8 activation and subsequent mitochondrial dysfunction.
References
Reference 1 Phytosphingosine derivatives ameliorate skin inflammation by inhibiting NF-KappaB and JAK/STAT signaling in keratinocytes and mice. J Invest Dermatol. 2014 Apr;134(4):1023-1032.
Reference 2 Phytosphingosine in combination with ionizing radiation enhances apoptotic cell death in radiation-resistant cancer cells through ROS-dependent and -independent AIF release. Blood. 2005 Feb 15;105(4):1724-33.
Reference 3 Phytosphingosine in combination with TRAIL sensitizes cancer cells to TRAIL through synergistic up-regulation of DR4 and DR5. Oncol Rep. 2007 Jan;17(1):175-84.
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