1-O-beta-D-glucopyranosyl-(2S,3R,8E)-2-[(2'R)-2-hydroxylpalmitoylamino]-8-octadecene-1,3-diol - Compound Card

1-O-beta-D-glucopyranosyl-(2S,3R,8E)-2-[(2'R)-2-hydroxylpalmitoylamino]-8-octadecene-1,3-diol

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1-O-beta-D-glucopyranosyl-(2S,3R,8E)-2-[(2'R)-2-hydroxylpalmitoylamino]-8-octadecene-1,3-diol

Structure
Zoomed Structure
  • Family: Plantae - Achariaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles CCCCCCCCCCCCCC[C@H](C(=O)N[C@H]([C@@H](CCCC/C=C/CCCCCCCCC)O)CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O
InChI InChI=1S/C40H77NO9/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-33(43)32(31-49-40-38(47)37(46)36(45)35(30-42)50-40)41-39(48)34(44)29-27-25-23-21-18-16-14-12-10-8-6-4-2/h19-20,32-38,40,42-47H,3-18,21-31H2,1-2H3,(H,41,48)/b20-19+/t32-,33+,34+,35+,36+,37-,38+,40+/m0/s1
InChIKey NJXYDZDDOCQODQ-WSEQXECZSA-N
Formula C40H77NO9
HBA 9
HBD 7
MW 716.05
Rotatable Bonds 33
TPSA 168.94
LogP 6.36
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 50
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 715.56
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Caloncoba welwitschii Achariaceae Plantae 2708920

Showing of synonyms

  • Keugwa CVT, Rosette EF, et al. (2023). Three new 30-norfriedelane and a new friedelane triterpenes from the trunk bark of Caloncoba welwitschii (Oliv.) Gilg (Achariaceae). Natural product research,2023, 37(3), 468-477. [View] [PubMed]
Pubchem: 163188328
Nmrshiftdb2: 70096366

No compound-protein relationship available.

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 716.05 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.8
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
133.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.21
Plasma Protein Binding
95.57
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
-0.47
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.9
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.18
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.52
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
-244888.06
Rat (Acute)
2.35
Rat (Chronic Oral)
4.02
Fathead Minnow
322.66
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
24115.16
Hydration Free Energy
-2.92
Log(D) at pH=7.4
4.39
Log(P)
9.78
Log S
-5.08
Log(Vapor Pressure)
-732.83
Melting Point
84.56
pKa Acid
6.24
pKa Basic
6.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.8190
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.8190
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7879
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7879
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7834
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7834
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7504
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7504
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7359
Beta-glucosidase A Q08638 BGLA_THEMA Thermotoga maritima 3 0.7359

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