N,N-dimethylsphingosine

Details

• Internal ID: ec608299-0ce9-4190-a8b7-96bc14475861
• Taxonomy: Organic nitrogen compounds > Organonitrogen compounds > Amines > Alkanolamines > 1,2-aminoalcohols
• IUPAC Name: (E,2S,3R)-2-(dimethylamino)octadec-4-ene-1,3-diol
• SMILES (Canonical): CCCCCCCCCCCCCC=CC(C(CO)N(C)C)O
• SMILES (Isomeric): CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N(C)C)O
• InChI: InChI=1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m0/s1
• InChI Key: YRXOQXUDKDCXME-YIVRLKKSSA-N
• Popularity: 180 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₄₁NO₂
• Molecular Weight: 327.50 g/mol
• Exact Mass: 327.313729551 g/mol
• Topological Polar Surface Area (TPSA): 43.70 Ų
• XlogP: 6.30
• Atomic LogP (AlogP): 4.53
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 16

Synonyms

• 119567-63-4
• D-erythro-N,N-dimethylsphingosine
• DIMETHYLSPINGOSINE
• N,N-Dimethylsphing-4-enine
• N,N-Dimethylsphingenine
• N,N-dimethyl-D-erythro-sphingosine
• N,N-Dimethylspingosine
• N,N-Dimethyl-D-erythrosphingenine
• (E,2S,3R)-2-(dimethylamino)octadec-4-ene-1,3-diol
• CHEMBL322333
• CHEBI:78759
• 4-Octadecene-1,3-diol, 2-(dimethylamino)-, (2S,3R,4E)-
• 4-Octadecene-1,3-diol, 2-(dimethylamino)-, (R-(R*,S*-(E)))-
• N,N-dimethyl-erythro-sphingosine
• N-dimethylsphingosine
• BSPBio_001420
• SCHEMBL121927
• BML3-C12
• SCHEMBL5493697
• C20H41NO2
• YRXOQXUDKDCXME-YIVRLKKSSA-N
• HMS1361G22
• HMS1791G22
• HMS1989G22
• HMS3402G22
• HMS3649E19
• BDBM50240721
• HB0237
• LMSP01070001
• N,N-Dimethyl-D-erythro-sphingosine]
• SL-105
• AKOS024458272
• IDI1_033890
• SMP2_000223
• NCGC00161359-01
• NCGC00161359-02
• NCGC00161359-03
• NCGC00161359-04
• N,N-Dimethylsphingosine, >=98% (HPLC)
• HY-108491
• CS-0028981
• 2S-(Dimethylamino)-4E-octadecene-1,3R-diol
• SR-01000946568
• J-004152
• SR-01000946568-1
• Q27147941
• (2S,3R,4E)-2-(Dimethylamino)-4-octadecene-1,3-diol
• (2S,3R,4E)-2-(dimethylamino)octadec-4-ene-1,3-diol
• (E)-(2S,3R)-2-Dimethylamino-octadec-4-ene-1,3-diol
• (S-(R,S-(E)))-2-(dimethylamino)-4-Octadecene-1,3-diol
• DMS, SK Inhibitor III, Sphingosine Kinase Inhibitor III
• Dimethyl Sphingosine (d18:1), N,N-dimethyl-D-erythro-sphingosine, chloroform

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9214	92.14%
Caco-2	+	0.5541	55.41%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Lysosomes	0.4912	49.12%
OATP2B1 inhibitior	-	0.8524	85.24%
OATP1B1 inhibitior	+	0.8483	84.83%
OATP1B3 inhibitior	+	0.9325	93.25%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6815	68.15%
P-glycoprotein inhibitior	-	0.7970	79.70%
P-glycoprotein substrate	-	0.8897	88.97%
CYP3A4 substrate	-	0.5653	56.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4436	44.36%
CYP3A4 inhibition	-	0.8646	86.46%
CYP2C9 inhibition	-	0.8253	82.53%
CYP2C19 inhibition	-	0.8723	87.23%
CYP2D6 inhibition	-	0.6447	64.47%
CYP1A2 inhibition	-	0.5952	59.52%
CYP2C8 inhibition	-	0.9339	93.39%
CYP inhibitory promiscuity	-	0.8392	83.92%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7600	76.00%
Carcinogenicity (trinary)	Non-required	0.6135	61.35%
Eye corrosion	-	0.7740	77.40%
Eye irritation	-	0.8621	86.21%
Skin irritation	-	0.6634	66.34%
Skin corrosion	-	0.5613	56.13%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3953	39.53%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.5611	56.11%
skin sensitisation	-	0.7706	77.06%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	-	0.9222	92.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6881	68.81%
Acute Oral Toxicity (c)	III	0.6504	65.04%
Estrogen receptor binding	-	0.5234	52.34%
Androgen receptor binding	-	0.7562	75.62%
Thyroid receptor binding	+	0.6046	60.46%
Glucocorticoid receptor binding	-	0.5075	50.75%
Aromatase binding	-	0.7160	71.60%
PPAR gamma	+	0.5707	57.07%
Honey bee toxicity	-	0.9621	96.21%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5028	50.28%
Fish aquatic toxicity	-	0.5917	59.17%

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	97.10%	97.29%
CHEMBL2581	P07339	Cathepsin D	96.80%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.99%	99.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.86%	92.08%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	94.58%	92.86%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.14%	96.09%
CHEMBL2885	P07451	Carbonic anhydrase III	92.88%	87.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.23%	93.56%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	88.09%	91.81%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	88.00%	85.94%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.72%	100.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.96%	90.08%
CHEMBL2664	P23526	Adenosylhomocysteinase	83.38%	86.67%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.08%	96.95%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.20%	82.50%
CHEMBL230	P35354	Cyclooxygenase-2	81.00%	89.63%
CHEMBL221	P23219	Cyclooxygenase-1	80.78%	90.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.19%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5282309
• LOTUS: LTS0122375
• wikiData: Q27147941