PHYTOSPHINGOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H39NO3
Molecular Weight	317.5072
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO

InChI

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

HIDE SMILES / InChI

Molecular Formula	C18H39NO3
Molecular Weight	317.5072
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15723652 | https://www.truthinaging.com/ingredients/phytosphingosine | https://www.ncbi.nlm.nih.gov/pubmed/28390782 | https://www.ncbi.nlm.nih.gov/pubmed/18489348 | https://www.ncbi.nlm.nih.gov/pubmed/20179727 | https://www.ncbi.nlm.nih.gov/pubmed/14522966

Phytosphingosine is structural analog of sphingolipids and is classified as long-chain sphingoid base. Phytosphingosine significantly induced chromatin DNA fragmentation. Phytosphingosine caused strong induction of caspase-8 activity and caspase-independent Bax translocation to the mitochondria. It shows excellent clinical results in the context of skin care in acne, based on both anti-inflammatory and anti-microbial activity. Phytosphingosine is currently seen in a variety of products as a skin and hair conditioning agent. Phytosphingosine might serve as an effective melanogenesis inhibitor in melanocytes via the regulation of the MITF signaling pathways. Dietary supplementation of phytosphingosine decreases plasma cholesterol levels and enhances insulin sensitivity in men with the metabolic syndrome.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
MITF signaling pathway 3 Target ID: MITF signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/28390782	Modulator 828
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14522966 \| https://www.ncbi.nlm.nih.gov/pubmed/15723652	Activator 1430
apoptotic DNA fragmentation 5 Target ID: GO:0006309 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15723652	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Metabolic syndrome 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20179727	Primary	Phase II 1132	Unknown Approved Use Unknown
Acne vulgaris 34 Sources: https://www.truthinaging.com/ingredients/phytosphingosine https://www.ncbi.nlm.nih.gov/pubmed/18489348	Primary	Phase II 1132	Unknown Approved Use Unknown
Hyperpigmentation 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28390782	Primary	Basic research	Unknown Approved Use Unknown
Skin Care 16 Sources: https://www.drugs.com/otc/130001/white-petrolatum.html	Inactive ingredient	Approved 8429	CheryLee MD TrueLipids Relieve and Protect Ointment Approved Use Uses: helps relieve, prevent and temporarily protect chafed, chapped, cracked or windburned skin and lips temporarily protects minor: cuts scrapes burns helps protect from the drying effects of wind and cold weather

PubMed

Title	Date	PubMed
Comparative analysis of glycosylinositol phosphorylceramides from fungi by electrospray tandem mass spectrometry with low-energy collision-induced dissociation of Li(+) adduct ions.	2001	11746891
Functional characterization of sphingolipid C4-hydroxylase genes from Arabidopsis thaliana.	2001 Apr 6	11297741
Occurrence of ceramides and neutral glycolipids with unusual long-chain base composition in purified rat liver mitochondria.	2001 Jan 19	11163764
Dependence of the sphingoid bases concentration on growth phase and temperature in the yeast Yarrowia lipolytica.	2002	11925759
Isolation and characterization of the genes encoding delta(8)-sphingolipid desaturase from Saccharomyces kluyveri and Kluyveromyces lactis.	2002 Dec	12402089
Deficiency of epidermal protein-bound omega-hydroxyceramides in atopic dermatitis.	2002 Jul	12164940
Sphingolipid functions in Saccharomyces cerevisiae.	2002 Jun 13	12069845
Mutant analysis reveals complex regulation of sphingolipid long chain base phosphates and long chain bases during heat stress in yeast.	2002 May	11967828
Isolation and structure of monomethylated GM3-type ganglioside molecular species from the starfish Luidia maculata.	2002 Oct	12372870
The emerging role for sphingolipids in the eukaryotic heat shock response.	2003 Apr	12785717
Phytosphingosine induces apoptotic cell death via caspase 8 activation and Bax translocation in human cancer cells.	2003 Feb	12576463
Tetraacetyl phytosphingosine-induced caspase activation and apoptosis occur through G2 arrest in human keratinocyte HaCaT cells.	2003 Nov	14708616
Isolation and structure of a GD3-Type ganglioside molecular species possessing neuritogenic activity from the starfish Luidia maculata.	2004 Aug	15305002
Acylceramide head group architecture affects lipid organization in synthetic ceramide mixtures.	2004 Nov	15482479
Molecular species of ceramides from the ascomycete truffle Tuber indicum.	2004 Sep	15351272
Inositol phosphoceramide synthase is a regulator of intracellular levels of diacylglycerol and ceramide during the G1 to S transition in Saccharomyces cerevisiae.	2005 May 15	15560753
Identification of mouse sphingomyelin synthase 1 as a suppressor of Bax-mediated cell death in yeast.	2006 Aug	16879426
Rapid demonstration of diversity of sulfatide molecular species from biological materials by MALDI-TOF MS.	2006 Aug	16670104
Structural organisation and phase behaviour of a stratum corneum lipid analogue: ceramide 3A.	2006 May 21	16688309
Phytosphingosine in combination with TRAIL sensitizes cancer cells to TRAIL through synergistic up-regulation of DR4 and DR5.	2007 Jan	17143496

Patents

Sample Use Guides

In Vivo Use Guide

500 mg twice daily for a 4 weeks

Route of Administration: Oral

In Vitro Use Guide

Jurkat and NCI-H460 cells were treated with 5 or 10 ug/ml phytosphingosine, respectively, for the 2, 5, 10, 30, 60, 120 min. phytosphingosine treatment led to a dramatic down-regulation of phosphorylated ERK1/2. The phosphorylated ERK started to diminish within 2 min of the phytosphingosine treatment.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:03:47 UTC 2023` Edited by `admin` on `Fri Dec 15 20:03:47 UTC 2023`
Record UNII	GIN46U9Q2Q
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PHYTOSPHINGOSINE

Official Name

English

D-RIBO-1,3,4-TRIHYDROXY-2-AMINOOCTADECANE

Common Name

English

1,3,4-OCTADECANETRIOL, 2-AMINO-, (2S-(2R*,3R*,4S*))-

Common Name

English

1,3,4-OCTADECANETRIOL, 2-AMINO-, D-RIBO-

Common Name

English

D-RIBO-PHYTOSPHINGOSINE

Common Name

English

DS-PHYTOSPHINGOSINE

Brand Name

English

1,3,4-OCTADECANETRIOL, 2-AMINO-, (2S,3S,4R)-

Systematic Name

English

(+)-D-RIBO-PHYTOSPHINGOSINE

Common Name

English

C18-PHYTOSPHINGOSINE

Common Name

English

CYTOMIDE PGS

Brand Name

English

BIOMIDE PS

Brand Name

English

SPHINGANINE, 4-D-HYDROXY

Common Name

English

PHYTOSPHINGOSINE [INCI]

Common Name

English

Phytosphingosine [WHO-DD]

Common Name

English

4-D-HYDROXYSPHINGANINE

Common Name

English

Code System Code Type Description

DRUG BANK

DB14119