Rel-(2S,3S,4R,16E)-2[(20R)-20-hydroxynonadecanoylamino]-heneicosadec-16-ene-1,3,4-triol - Compound Card

Rel-(2S,3S,4R,16E)-2[(20R)-20-hydroxynonadecanoylamino]-heneicosadec-16-ene-1,3,4-triol

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Rel-(2S,3S,4R,16E)-2[(20R)-20-hydroxynonadecanoylamino]-heneicosadec-16-ene-1,3,4-triol

Structure
Zoomed Structure
  • Family: Plantae - Caesalpinioideae
  • Kingdom: Plantae
  • Class: Lipid
    • Subclass: Ceramide
Canonical Smiles CCCCCCCCCCCCCCCCC[C@H](C(=O)N[C@H]([C@@H]([C@@H](CCCCCCCCCCC/C=C/CCCC)O)O)CO)O
InChI InChI=1S/C40H79NO5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-37(43)39(45)36(35-42)41-40(46)38(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h9,11,36-39,42-45H,3-8,10,12-35H2,1-2H3,(H,41,46)/b11-9+/t36-,37+,38+,39-/m0/s1
InChIKey VQIZWSRUDAHJGQ-NRHDGBMMSA-N
Formula C40H79NO5
HBA 5
HBD 5
MW 654.07
Rotatable Bonds 36
TPSA 110.02
LogP 9.85
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 46
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 653.6
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Gilbertiodendron dewevrei Caesalpinioideae Plantae 162777

Showing of synonyms

  • Stephanie DM, Stéphane FFY, et al. (2022). Dewerin and gilbertionol two new secondary metabolites from the stem bark of Gilbertiodendron dewevrei (De Wild) J. Leonard.. Natural product research,2022, 36(1), 214-222. [View] [PubMed]
Pubchem: 163056530
Nmrshiftdb2: 70111540

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.45
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.89
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
15.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.77
Plasma Protein Binding
79.0
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
-0.49
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.64
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.14
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.2
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
-33806.74
Rat (Acute)
2.03
Rat (Chronic Oral)
3.85
Fathead Minnow
60.68
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
1383.54
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.42
Log(P)
13.67
Log S
-6.75
Log(Vapor Pressure)
-26.45
Melting Point
85.54
pKa Acid
8.42
pKa Basic
5.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8661
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8550
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8511
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8401
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.8207
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7884
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7783
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.7706
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7693
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7671
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7666
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7648
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7520
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7509
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7434
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7384
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7346
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7081

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