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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
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2D MOL

3D MOL

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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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Cite NPCDR
Visitor Map
Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China