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

2S,3R-4E,8E-2-(hexadecanoylamino)-docosa-4,8-diene-1,3-diol

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2S,3R-4E,8E-2-(hexadecanoylamino)-docosa-4,8-diene-1,3-diol

Structure
Zoomed Structure
  • Family: Animalia - Xeniidae
  • Kingdom: Animalia
  • Class: Ceramide
Canonical Smiles CCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](/C=C/CC/C=C/CCCCCCCCCCCCC)O)CO
InChI InChI=1S/C38H73NO3/c1-3-5-7-9-11-13-15-17-18-19-20-22-23-25-27-29-31-33-37(41)36(35-40)39-38(42)34-32-30-28-26-24-21-16-14-12-10-8-6-4-2/h23,25,31,33,36-37,40-41H,3-22,24,26-30,32,34-35H2,1-2H3,(H,39,42)/b25-23+,33-31+/t36-,37+/m0/s1
InChIKey BAXNUBOEQRHLSD-HBFBPLQUSA-N
Formula C38H73NO3
HBA 3
HBD 3
MW 592.01
Rotatable Bonds 33
TPSA 69.56
LogP 10.9
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 591.56
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: 134720246
Nmrshiftdb2: 60020263

No compound-protein relationship available.

No scaffolds available.

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.19
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
2.15
Plasma Protein Binding
67.23
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
Inhibitor

Excretion

Clearance
0.36
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.12
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.59
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
-5625.34
Rat (Acute)
2.15
Rat (Chronic Oral)
3.45
Fathead Minnow
17.82
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
363.41
Hydration Free Energy
-2.87
Log(D) at pH=7.4
6.49
Log(P)
13.96
Log S
-6.68
Log(Vapor Pressure)
-10.72
Melting Point
73.26
pKa Acid
11.0
pKa Basic
5.18
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 0.9847
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.9847
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9800
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9800
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9620
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9620
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9478
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9478
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9350
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9350
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9206
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9206
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.9101
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.9101
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9012
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9012
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8857
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8857
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8694
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8694
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.8539
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.8539
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7822
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7822
Xylose isomerase P12070 XYLA_ARTS7 Arthrobacter sp 3 0.7722
Xylose isomerase P12070 XYLA_ARTS7 Arthrobacter sp 3 0.7722
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7590
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7590
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7486
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7486
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7334
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7334
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7273
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7273
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7255
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7255
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 3 0.7215
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 3 0.7215
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7181
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7181
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7176
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7176
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 4 0.7159
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 4 0.7159
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7126
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7126
Actin, alpha skeletal muscle P68134 ACTS_MOUSE Mus musculus 3 0.7035
Actin, alpha skeletal muscle P68134 ACTS_MOUSE Mus musculus 3 0.7035

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