3-O-(beta-D-glucopyranosyl)-28-O-[alpha-L-rhamnopyranosyl-(1→3)-beta-D-xylopyranosyl-(1→4)-alpha-L-rhamnopyranosyl-(1→2)-beta-D-xylopyranosyl]protobassic acid - Compound Card

3-O-(beta-D-glucopyranosyl)-28-O-[alpha-L-rhamnopyranosyl-(1→3)-beta-D-xylopyranosyl-(1→4)-alpha-L-rhamnopyranosyl-(1→2)-beta-D-xylopyranosyl]protobassic acid

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3-O-(beta-D-glucopyranosyl)-28-O-[alpha-L-rhamnopyranosyl-(1→3)-beta-D-xylopyranosyl-(1→4)-alpha-L-rhamnopyranosyl-(1→2)-beta-D-xylopyranosyl]protobassic acid

Structure
Zoomed Structure
  • Family: Plantae - Sapotaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Triterpenoid Saponin
Canonical Smiles OCC1OC(O[C@H]2CC[C@]3(C([C@]2(C)CO)[C@H](O)C[C@@]2(C3CC=C3[C@@]2(C)CC[C@@]2(C3CC(C)(C)CC2)C(=O)OC2OC[C@H]([C@@H]([C@@H]2OC2OC(C)[C@@H](C(C2O)O)OC2OC[C@H]([C@@H]([C@@H]2O)OC2O[C@@H](C)[C@@H]([C@@H](C2O)O)O)O)O)O)C)C)[C@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C58H94O26/c1-23-33(64)36(67)39(70)48(77-23)82-44-29(63)21-75-47(42(44)73)81-43-24(2)78-49(41(72)38(43)69)83-45-34(65)28(62)20-76-51(45)84-52(74)58-15-13-53(3,4)17-26(58)25-9-10-31-54(5)12-11-32(80-50-40(71)37(68)35(66)30(19-59)79-50)55(6,22-60)46(54)27(61)18-57(31,8)56(25,7)14-16-58/h9,23-24,26-51,59-73H,10-22H2,1-8H3/t23-,24?,26?,27+,28+,29+,30?,31?,32-,33-,34-,35+,36-,37-,38?,39?,40-,41?,42-,43-,44-,45-,46?,47?,48?,49?,50?,51?,54+,55+,56+,57+,58-/m0/s1
InChIKey PJIJGDPCKCOYLX-QQVUWVTNSA-N
Formula C58H94O26
HBA 26
HBD 15
MW 1207.36
Rotatable Bonds 12
TPSA 412.82
LogP -2.93
Number Rings 10
Number Aromatic Rings 0
Heavy Atom Count 84
Formal Charge 0
Fraction CSP3 0.95
Exact Mass 1206.6
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Mimusops laurifolia Sapotaceae Plantae 1227943

Showing of synonyms

  • Eskander J, Lavaud C, et al. (2005). Saponins from the Leaves of Mimusops laurifolia.. Journal of natural products, 2005, 68(6), 832-41. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(CC2)CC(CC3)C2C(CC4)C3C(CC5)C=4C(CCCC6)C56C(=O)OC(OCCC7)C7OC(OC8)CCC8OC(OCC9)CC9OC1CCCCO1

Level: 5

Mol. Weight: 1207.36 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3C(OCCC3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)CC(CC8)OC9CCCCO9

Level: 4

Mol. Weight: 1207.36 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(OC7)CCC7OC(OCC8)CC8OC9CCCCO9

Level: 4

Mol. Weight: 1207.36 g/mol

Structure

SMILES: O1CCCCC1OC2C(OCCC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC8CCCCO8

Level: 3

Mol. Weight: 1207.36 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(OC7)CCC7OC8CCCCO8

Level: 3

Mol. Weight: 1207.36 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4CCCOC4

Level: 3

Mol. Weight: 1207.36 g/mol

Structure

SMILES: O1CCCCC1OC2C(OCCC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CCCC7

Level: 2

Mol. Weight: 1207.36 g/mol

Structure

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 2

Mol. Weight: 1207.36 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1207.36 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1207.36 g/mol

Structure

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 1207.36 g/mol

Structure

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

Level: 1

Mol. Weight: 1207.36 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1207.36 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1207.36 g/mol

Structure

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

Level: 0

Mol. Weight: 1207.36 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1207.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.56
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
738282879.51
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
96484924911.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
47.7
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
1.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-2244020586.57
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-916.75
Liver Injury II
Safe
hERG Blockers
Toxic
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
-175115481977515.1
Rat (Acute)
4.12
Rat (Chronic Oral)
375607.08
Fathead Minnow
221045967500.27
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
19695637445399.273
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-10948801.49
Log(P)
-1274.12
Log S
-2.99
Log(Vapor Pressure)
-648567458288.67
Melting Point
-193705.03
pKa Acid
-4725837699.27
pKa Basic
-38019211.08

No predicted protein targets found for this compound.

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