3-O-beta-D-glucopyranosyl-(1 → 2)-beta-D-glucuronopyranosyl oleanolic acid - Compound Card

3-O-beta-D-glucopyranosyl-(1 → 2)-beta-D-glucuronopyranosyl oleanolic acid

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3-O-beta-D-glucopyranosyl-(1 → 2)-beta-D-glucuronopyranosyl oleanolic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Saponin
Canonical Smiles OCC1O[C@@H](O[C@@H]2[C@@H](OC([C@H](C2O)O)C(=O)O)O[C@H]2CC[C@]3(C(C2(C)C)CC[C@@]2(C3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O)C)C)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C42H66O14/c1-37(2)14-16-42(36(51)52)17-15-40(6)20(21(42)18-37)8-9-24-39(5)12-11-25(38(3,4)23(39)10-13-41(24,40)7)54-35-32(29(47)28(46)31(55-35)33(49)50)56-34-30(48)27(45)26(44)22(19-43)53-34/h8,21-32,34-35,43-48H,9-19H2,1-7H3,(H,49,50)(H,51,52)/t21-,22?,23?,24?,25-,26+,27?,28-,29?,30-,31?,32-,34-,35+,39-,40+,41+,42-/m0/s1
InChIKey WJQOMUVKRDJBGZ-HKIOEFLFSA-N
Formula C42H66O14
HBA 12
HBD 8
MW 794.98
Rotatable Bonds 7
TPSA 232.9
LogP 2.97
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 56
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 794.45
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Calendula stellata Asteraceae Plantae 1565984

Showing of synonyms

  • Lehbili M, Alabdul Magid A, et al. (2017). Oleanane-type triterpene saponins from Calendula stellata. Phytochemistry, 2017, 144, 33-42. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC7CCCCO7

Level: 2

Mol. Weight: 794.98 g/mol

Structure

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

Level: 1

Mol. Weight: 794.98 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 794.98 g/mol

Structure

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

Level: 0

Mol. Weight: 794.98 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 794.98 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.17
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
13.71
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2639.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.04
Plasma Protein Binding
93.0
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
0.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-65.56
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.05
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.53
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
-4790295.37
Rat (Acute)
2.64
Rat (Chronic Oral)
4.11
Fathead Minnow
6052.04
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
534949.76
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.54
Log(P)
3.75
Log S
-3.08
Log(Vapor Pressure)
-17511.62
Melting Point
250.43
pKa Acid
-88.34
pKa Basic
8.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mexicain P84346 MEX1_JACME Jacaratia mexicana 3 0.7905
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7839
Aspartate carbamoyltransferase catalytic subunit P05654 PYRB_BACSU Bacillus subtilis 3 0.7806
Ficolin-2 Q15485 FCN2_HUMAN Homo sapiens 3 0.7505
2-dehydro-3-deoxyphosphooctonate aldolase P0A715 KDSA_ECOLI Escherichia coli 3 0.7484

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