3-O-[O-alpha-l-rhamnopyranosyl-(1→3)]-O-[O-beta-d-glucopyranosyl-(1→3)]-beta-d-glucopyranosyl oleanolic acid - Compound Card

3-O-[O-alpha-l-rhamnopyranosyl-(1→3)]-O-[O-beta-d-glucopyranosyl-(1→3)]-beta-d-glucopyranosyl oleanolic acid

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3-O-[O-alpha-l-rhamnopyranosyl-(1→3)]-O-[O-beta-d-glucopyranosyl-(1→3)]-beta-d-glucopyranosyl oleanolic acid

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Triterpenoid Saponin
Canonical Smiles OCC1OC(O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O)C)C)C(C(C1O)OC1OC(CO)C(C(C1O)O)O)O[C@H]1O[C@@H](CO)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C48H78O18/c1-43(2)14-16-48(42(59)60)17-15-46(6)22(23(48)18-43)8-9-28-45(5)12-11-29(44(3,4)27(45)10-13-47(28,46)7)64-41-38(66-40-36(58)34(56)31(53)25(20-50)62-40)37(32(54)26(21-51)63-41)65-39-35(57)33(55)30(52)24(19-49)61-39/h8,23-41,49-58H,9-21H2,1-7H3,(H,59,60)/t23-,24?,25-,26?,27-,28+,29-,30?,31-,32?,33?,34+,35?,36-,37?,38?,39?,40+,41?,45-,46+,47+,48-/m0/s1
InChIKey OGKRHYLZKFTGGO-USYHZMSDSA-N
Formula C48H78O18
HBA 17
HBD 11
MW 943.13
Rotatable Bonds 10
TPSA 294.98
LogP 0.71
Number Rings 8
Number Aromatic Rings 0
Heavy Atom Count 66
Formal Charge 0
Fraction CSP3 0.94
Exact Mass 942.52
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Catunaregam nilotica Rubiaceae Plantae 353862

Showing of synonyms

  • Lemmich E, Cornett C, et al. (1995). Molluscicidal saponins from Catunaregam nilotica. Phytochemistry, 1995, 39(1), 63-8. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6OCCC(OC7CCCCO7)C6OC8CCCCO8

Level: 3

Mol. Weight: 943.13 g/mol

Structure

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

Level: 2

Mol. Weight: 943.13 g/mol

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCC6)CC6OC7CCCCO7

Level: 2

Mol. Weight: 943.13 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 943.13 g/mol

Structure

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

Level: 1

Mol. Weight: 943.13 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 943.13 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 943.13 g/mol

Structure

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

Level: 0

Mol. Weight: 943.13 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 943.13 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
2927.34
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
383446.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.9
Plasma Protein Binding
67.02
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
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
0.96
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-8911.64
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.22
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.05
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
-695934082.35
Rat (Acute)
3.39
Rat (Chronic Oral)
4.85
Fathead Minnow
878475.25
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
78268959.12
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-28.43
Log(P)
2.57
Log S
-2.64
Log(Vapor Pressure)
-2577214.39
Melting Point
228.11
pKa Acid
-18698.67
pKa Basic
-119.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7462

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