2S,3R-4E,8E-2-(octadecanoylamino)-octadeca-4,8-diene-1,3-diol - Compound Card

2S,3R-4E,8E-2-(octadecanoylamino)-octadeca-4,8-diene-1,3-diol

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2S,3R-4E,8E-2-(octadecanoylamino)-octadeca-4,8-diene-1,3-diol

Structure
Zoomed Structure
  • Family: Animalia - Xeniidae
  • Kingdom: Animalia
  • Class: Ceramide
Canonical Smiles CCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CC/C=C/CCCCCCCCC)O)CO
InChI InChI=1S/C36H69NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h21,23,29,31,34-35,38-39H,3-20,22,24-28,30,32-33H2,1-2H3,(H,37,40)/b23-21+,31-29+/t34-,35+/m0/s1
InChIKey WNPWDGNHTKGEDS-JZISHWLJSA-N
Formula C36H69NO3
HBA 3
HBD 3
MW 563.95
Rotatable Bonds 31
TPSA 69.56
LogP 10.12
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 563.53
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Heteroxenia ghardaqensis Alcyoniidae Animalia 859395
2 Heteroxenia ghardaqensis Xeniidae Animalia 859395

Showing of synonyms

  • Abdel-Razik AF, Nassar MI, et al. (2015). A new cytotoxic ceramide from Heteroxenia ghardaqensis and protective effect of chloroform extract against cadmium toxicity in rats. Arabian Journal of Chemistry,2015,in press. [View]
Pubchem: 90657626
Nmrshiftdb2: 60020260

No compound-protein relationship available.

No scaffolds available.

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.21
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.38
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.19

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
2.07
Plasma Protein Binding
65.92
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.62
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
4.35
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2119.05
Rat (Acute)
2.14
Rat (Chronic Oral)
3.34
Fathead Minnow
10.91
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
459.54
Hydration Free Energy
-2.9
Log(D) at pH=7.4
6.09
Log(P)
12.93
Log S
-6.55
Log(Vapor Pressure)
-10.46
Melting Point
69.36
pKa Acid
10.82
pKa Basic
5.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.9647
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.9647
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9641
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9641
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9443
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9443
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9398
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9398
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9381
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9381
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.8978
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.8978
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8897
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8897
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8605
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8605
Xylose isomerase P12070 XYLA_ARTS7 Arthrobacter sp 3 0.7695
Xylose isomerase P12070 XYLA_ARTS7 Arthrobacter sp 3 0.7695
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7582
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7582
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7566
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7566
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7332
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7332
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 3 0.7258
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 3 0.7258
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7235
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7235
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7227
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7227
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7223
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7223
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7216
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7216
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7181
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7181
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7138
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7138
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7126
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7126
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7115
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7115

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