Phytosphingosine

Details

• Internal ID: 145a3e68-1ac6-4e43-8734-e4c3ce2a3608
• Taxonomy: Organic nitrogen compounds > Organonitrogen compounds > Amines > Alkanolamines > 1,3-aminoalcohols
• IUPAC Name: (2S,3S,4R)-2-aminooctadecane-1,3,4-triol
• InChI: 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
• InChI Key: AERBNCYCJBRYDG-KSZLIROESA-N
• Popularity: 1,219 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₉NO₃
• Molecular Weight: 317.50 g/mol
• Exact Mass: 317.29299411 g/mol
• Topological Polar Surface Area (TPSA): 86.70 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 3.12
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 16

Synonyms

• 554-62-1
• (2S,3S,4R)-2-aminooctadecane-1,3,4-triol
• 4-D-Hydroxysphinganine
• D-Ribo-phytosphingosine
• C18-Phytosphingosine
• DS-phytosphingosine
• (+)-D-ribo-Phytosphingosine
• 388566-94-7
• UNII-GIN46U9Q2Q
• 1,3,4-Octadecanetriol, 2-amino-, (2S,3S,4R)-
• GIN46U9Q2Q
• 4-R-hydroxyoctadecasphinganine
• 4R-hydroxysphinganine
• CHEBI:46961
• CYTOMIDE PGS
• BIOMIDE PS
• N-Dodecanoyl-NBD-phytosphingosine
• D-Ribo-1,3,4-trihydroxy-2-aminooctadecane
• SPHINGANINE, 4-D-HYDROXY
• DTXSID80203951
• EC 439-210-6
• 4-hydroxysphinganine
• 1,3,4-Octadecanetriol, 2-amino-, (2S-(2R*,3R*,4S*))-
• 4R-hydroxasphinganine
• 1,3,4-OCTADECANETRIOL, 2-AMINO-, D-RIBO-
• phytosphingosine (C18)
• 4R-hydroxysphinganine (C18)
• D-ribo-4-hydroxysphinganine (C18)
• t18:0
• C18H39NO3
• Phytosphingosin
• 4D-Hydroxysphinganine
• 4-D-hydroxy-Sphinganine
• SCHEMBL20110
• C18-PHS
• PHYTOSPHINGOSINE [INCI]
• CHEMBL236036
• DTXCID10126442
• PHYTOSPHINGOSINE [WHO-DD]
• 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
• A870186
• 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
• D-ribo-Phytosphingosine, 4-hydroxysphinganine (Saccharomyces Cerevisiae), powder

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9158	91.58%
Caco-2	-	0.7645	76.45%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Lysosomes	0.7066	70.66%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.9520	95.20%
OATP1B3 inhibitior	+	0.9124	91.24%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8791	87.91%
BSEP inhibitior	-	0.8603	86.03%
P-glycoprotein inhibitior	-	0.9108	91.08%
P-glycoprotein substrate	-	0.8223	82.23%
CYP3A4 substrate	-	0.6251	62.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3912	39.12%
CYP3A4 inhibition	-	0.9328	93.28%
CYP2C9 inhibition	-	0.8923	89.23%
CYP2C19 inhibition	-	0.8904	89.04%
CYP2D6 inhibition	+	0.6463	64.63%
CYP1A2 inhibition	+	0.6410	64.10%
CYP2C8 inhibition	-	0.9468	94.68%
CYP inhibitory promiscuity	-	0.9129	91.29%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6978	69.78%
Eye corrosion	-	0.8647	86.47%
Eye irritation	-	0.8906	89.06%
Skin irritation	-	0.8722	87.22%
Skin corrosion	-	0.9639	96.39%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5150	51.50%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.5609	56.09%
skin sensitisation	-	0.8550	85.50%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.7531	75.31%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.5881	58.81%
Acute Oral Toxicity (c)	IV	0.4990	49.90%
Estrogen receptor binding	-	0.6537	65.37%
Androgen receptor binding	-	0.6848	68.48%
Thyroid receptor binding	+	0.6133	61.33%
Glucocorticoid receptor binding	+	0.6328	63.28%
Aromatase binding	-	0.6859	68.59%
PPAR gamma	-	0.5961	59.61%
Honey bee toxicity	-	0.9915	99.15%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5436	54.36%
Fish aquatic toxicity	-	0.8432	84.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	98.41%	97.29%
CHEMBL4040	P28482	MAP kinase ERK2	97.38%	83.82%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.99%	92.86%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.83%	96.09%
CHEMBL2885	P07451	Carbonic anhydrase III	94.51%	87.45%
CHEMBL2581	P07339	Cathepsin D	92.90%	98.95%
CHEMBL230	P35354	Cyclooxygenase-2	91.41%	89.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.47%	99.17%
CHEMBL1907	P15144	Aminopeptidase N	90.03%	93.31%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	88.84%	92.08%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.14%	100.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	83.63%	85.94%
CHEMBL4581	P52732	Kinesin-like protein 1	83.29%	93.18%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.88%	93.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.46%	96.95%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.27%	91.81%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 122121
• LOTUS: LTS0147154
• wikiData: Q3746193