Hederagenin-3-O-beta-D-glucuronopyranoside - Compound Card

Hederagenin-3-O-beta-D-glucuronopyranoside

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Hederagenin-3-O-beta-D-glucuronopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Chenopodiaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Monodesmosidic Saponin
Canonical Smiles CCO[C@@H]1[C@H](OC([C@@H]([C@H]1O)O)O[C@H]1CC[C@]2([C@H]([C@]1(C)CO)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C)C(=O)O
InChI InChI=1S/C38H60O10/c1-8-46-28-26(40)27(41)31(48-29(28)30(42)43)47-25-12-13-34(4)23(35(25,5)20-39)11-14-37(7)24(34)10-9-21-22-19-33(2,3)15-17-38(22,32(44)45)18-16-36(21,37)6/h9,22-29,31,39-41H,8,10-20H2,1-7H3,(H,42,43)(H,44,45)/t22-,23+,24+,25-,26+,27+,28-,29-,31?,34-,35-,36+,37+,38-/m0/s1
InChIKey MNXGYEJYONFZKY-LFOKCNBKSA-N
Formula C38H60O10
HBA 8
HBD 5
MW 676.89
Rotatable Bonds 7
TPSA 162.98
LogP 5.17
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 676.42
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Atriplex nummularia Chenopodiaceae Plantae 3553

Showing of synonyms

  • Christensen SB, Omar AA (1985). Atriplex nummularia, a source for the two molluscicide saponins: Hederagenin-3-O-beta-D-glucuronopyranoside and calenduloside E. Journal of Natural Products,1985,48(1),161-161. [View]
Pubchem: 163033443
Nmrshiftdb2: 70085675

No compound-protein relationship available.

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 1

Mol. Weight: 676.89 g/mol

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 676.89 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 676.89 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.95
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.36
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
57.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.13
Plasma Protein Binding
104.82
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
3.33
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.11
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.21
Micronucleos
Toxic
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
-110940.33
Rat (Acute)
2.1
Rat (Chronic Oral)
2.4
Fathead Minnow
151.89
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
9290.89
Hydration Free Energy
-2.92
Log(D) at pH=7.4
2.13
Log(P)
4.87
Log S
-4.66
Log(Vapor Pressure)
-270.39
Melting Point
280.02
pKa Acid
1.57
pKa Basic
6.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8698
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8698
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7188
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7188

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