3-O-[alpha-L-rhamnopyranosyl (1→4)-beta-D-glucopyranosyl] oleanolic acid 28-O-beta-D-glucopyranosyl ester - Compound Card

3-O-[alpha-L-rhamnopyranosyl (1→4)-beta-D-glucopyranosyl] oleanolic acid 28-O-beta-D-glucopyranosyl ester

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3-O-[alpha-L-rhamnopyranosyl (1→4)-beta-D-glucopyranosyl] oleanolic acid 28-O-beta-D-glucopyranosyl ester

Structure
Zoomed Structure
  • Family: Plantae - Umbelliferae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Triterpenoid Saponin
Canonical Smiles OCC1OC(O[C@H]2CC[C@]3(C(C2(C)C)CC[C@@]2(C3CC=C3[C@]2(C)CCC2C3CC(C)(C)C[C@H]2C(=O)OC2OC(CO)C(C(C2O)O)O)C)C)C(C(C1OC1OC(C)C(C(C1O)O)O)O)O
InChI InChI=1S/C48H78O17/c1-21-31(51)33(53)36(56)41(60-21)64-39-27(20-50)62-42(38(58)35(39)55)63-30-13-14-46(6)28(45(30,4)5)12-16-48(8)29(46)10-9-25-23-17-44(2,3)18-24(22(23)11-15-47(25,48)7)40(59)65-43-37(57)34(54)32(52)26(19-49)61-43/h9,21-24,26-39,41-43,49-58H,10-20H2,1-8H3/t21?,22?,23?,24-,26?,27?,28?,29?,30+,31?,32?,33?,34?,35?,36?,37?,38?,39?,41?,42?,43?,46+,47+,48-/m1/s1
InChIKey GDDWBRXNMFYZQY-HTKBYPOOSA-N
Formula C48H78O17
HBA 17
HBD 10
MW 927.14
Rotatable Bonds 8
TPSA 274.75
LogP 1.02
Number Rings 8
Number Aromatic Rings 0
Heavy Atom Count 65
Formal Charge 0
Fraction CSP3 0.94
Exact Mass 926.52
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Bupleurum lancifolium Umbelliferae Plantae 198842

Showing of synonyms

  • Achouri A, Derbré S, et al. (2017). Two new triterpenoid saponins from the leaves of Bupleurum lancifolium (Apiaceae). Natural Product Research, 2017,31(19),2286–2292. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)C2CCCC3C2CCC(C3=4)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8CCCCO8

Level: 3

Mol. Weight: 927.14 g/mol

Structure

SMILES: O1CCCCC1OC(=O)C2CCCC3C2CCC(C3=4)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 2

Mol. Weight: 927.14 g/mol

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OC6)CCC6OC7CCCCO7

Level: 2

Mol. Weight: 927.14 g/mol

Structure

SMILES: O1CCCCC1OC(=O)C2CCCC3C2CCC(C3=4)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 927.14 g/mol

Structure

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

Level: 1

Mol. Weight: 927.14 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 927.14 g/mol

Structure

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

Level: 0

Mol. Weight: 927.14 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 927.14 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.42
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
1795.01
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
235401.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.91
Plasma Protein Binding
40.48
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.58
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-5471.51
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.93
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.14
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
-427242719.19
Rat (Acute)
3.69
Rat (Chronic Oral)
4.63
Fathead Minnow
539312.05
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
48049088.73
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-10.84
Log(P)
2.92
Log S
-3.12
Log(Vapor Pressure)
-1582115.52
Melting Point
272.57
pKa Acid
-11442.74
pKa Basic
-67.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8787
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8131
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7103

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