D-ribo-Phytosphingosine - ≥98% , CAS No.554-62-1

CAS: 554-62-1 Cat. No.: D136389 Molecular Weight: 317.51 Beilstein Registry Number: 4(4)1906 EC Number: 439-210-6

GRADE & PURITY ≥98%

Synonyms

4-D-Hydroxysphinganine | 4-D-hydroxy-Sphinganine | D-Ribo-1,3,4-trihydroxy-2-aminooctadecane | Hidroc Clora | 1,3,4-OCTADECANETRIOL, 2-AMINO-, D-RIBO- | PHYTOSPHINGOSINE [INCI] | SCHEMBL20110 | SR-05000002328-2 | UNII-GIN46U9Q2Q | D-ribo-Phytosphingosine,

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

4-D-Hydroxysphinganine | 4-D-hydroxy-Sphinganine | D-Ribo-1, 3, 4-trihydroxy-2-aminooctadecane | Hidroc Clora | 1, 3, 4-OCTADECANETRIOL, 2-AMINO-, D-RIBO- | PHYTOSPHINGOSINE [INCI] | SCHEMBL20110 | SR-05000002328-2 | UNII-GIN46U9Q2Q | D-ribo-Phytosphingosine,

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Phytosphingosine is a long chain sphingoid base that occurs broadly in yeast, plants and animals including mammals. In yeast it is involved in mediating the heat stress response, perhaps through activation of the AGC-type protein kinases, Pkh1, Pkh2, Ypk1

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488187666
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187666
• Canonical Smiles: CCCCCCCCCCCCCCC(C(C(CO)N)O)O
• IUPAC Name: (2S,3S,4R)-2-aminooctadecane-1,3,4-triol
• InChIKey: AERBNCYCJBRYDG-KSZLIROESA-N
• 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
• Isomeric SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)N)O)O
• Molecular Weight: 317.51
• Beilstein: 4(4)1906
• Reaxy-Rn: 1725300
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1725300&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines
        • Level5 Alkanolamines
          • Level6 1,3-aminoalcohols

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Alkanolamines
• Direct Parent: 1,3-aminoalcohols
• Alternative Parents: Secondary alcohols 1,2-aminoalcohols Polyols Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: 1,3-aminoalcohol - Secondary alcohol - 1,2-aminoalcohol - Polyol - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Primary alcohol - Organooxygen compound - Primary aliphatic amine - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1,3-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C3 atom.
• External Descriptors: 4-Hydroxysphinganines (Phytosphingosines)

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

VDR Tclin Vitamin D receptor (26531 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

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Jurkat (10389 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

Discover Target: POLK

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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Candida albicans (78123 Activities)

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Nakaseomyces glabratus (9108 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

Discover Target: ffp

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Endoglycoceramidase II (93 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO (Slightly, Heated), Methanol (Slightly), Pyridine (Slightly)
• Specific Rotation[α]: 9° (C=1,Pyridine)
• Melt Point(°C): 102°C(lit.)
• Molecular Weight: 317.500 g/mol
• XLogP3: 4.600
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 16
• Exact Mass: 317.293 Da
• Monoisotopic Mass: 317.293 Da
• Topological Polar Surface Area: 86.700 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 226.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yang Zhang, Xiaowen Liu, Guojing Yu, Hongzhe Gui, Jingteng Chi, Shuhan Liu, Liang Fang, Mingzhe Liu.  (2023)  Innovative insight into the mechanism of enantioselective skin permeation for chiral drugs.  Expert Opinion on Drug Delivery,      [PMID:38112192] [10.1080/17425247.2023.2294877]

2. Li Lingru, Li Tianxing, Liang Xue, Zhu Linghui, Fang Yini, Dong Ling, Zheng Yi, Xu Xiaoxue, Li Mingrui, Cai Tianqi, Zhao Fufangyu, Xin Meiling, Shao Mingyan, Guan Yuanyuan, Liu Meiyi, Li Fangli, Zhang Chenhong, Wang Qi, Sun Wenlong, Zheng Yanfei.  (2025)  A decrease in Flavonifractor plautii and its product, phytosphingosine, predisposes individuals with phlegm-dampness constitution to metabolic disorders.  Cell Discovery,  11  (1): (1-21).  [PMID:40097405] [10.1038/s41421-025-00789-x]