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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Sapotaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Triterpenoid Saponin
Canonical Smiles OCC1OC(O[C@H]2[C@@H](O)C[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)O[C@@H]2OC[C@H]([C@@H](C2OC2O[C@@H](C)[C@@H](C([C@@H]2O)O)O[C@@H]2OC[C@H]([C@@H](C2O)OC2O[C@@H](C)[C@@H](C([C@@H]2O)O)O)O[C@@H]2OC[C@H]([C@@H](C2O)O)O)O)O)C)C)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C63H102O31/c1-23-34(70)38(74)42(78)53(86-23)91-47-32(89-51-41(77)35(71)29(68)19-83-51)21-85-52(45(47)81)90-46-24(2)87-54(44(80)40(46)76)92-48-36(72)30(69)20-84-56(48)94-57(82)63-13-11-58(3,4)15-26(63)25-9-10-33-59(5)16-28(67)50(93-55-43(79)39(75)37(73)31(18-64)88-55)60(6,22-65)49(59)27(66)17-62(33,8)61(25,7)12-14-63/h9,23-24,26-56,64-81H,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-,52-,53?,54?,55?,56-,59+,60-,61+,62+,63-/m0/s1
InChIKey LXNUHBQFMKETMR-VSCAUBCMSA-N
Formula C63H102O31
HBA 31
HBD 18
MW 1355.48
Rotatable Bonds 14
TPSA 491.97
LogP -5.5
Number Rings 11
Number Aromatic Rings 0
Heavy Atom Count 94
Formal Charge 0
Fraction CSP3 0.95
Exact Mass 1354.64
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(C9)OCC(OC1CCCCO1)C9OC1CCCCO1

Level: 6

Mol. Weight: 1355.48 g/mol

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: 1355.48 g/mol

Structure

SMILES: O1CCCCC1OC(CC2)CC(CC3)C2C(CC4)C3C(CC5)C=4C(CCCC6)C56C(=O)OC(OCCC7)C7OC(OC8)CCC8OC(OC9)CCC9OC1CCCCO1

Level: 5

Mol. Weight: 1355.48 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(OC7)CCC7OC(C8)OCC(OC9CCCCO9)C8OC1CCCCO1

Level: 5

Mol. Weight: 1355.48 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: 1355.48 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: 1355.48 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(OC7)CCC7OC(OC8)CCC8OC9CCCCO9

Level: 4

Mol. Weight: 1355.48 g/mol

Structure

SMILES: O1CCCCC1OC2C(OC3CCCCO3)COC(C2)OC4CCC(OC4)OC5CCCOC5

Level: 4

Mol. Weight: 1355.48 g/mol

Structure

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

Level: 3

Mol. Weight: 1355.48 g/mol

Structure

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

Level: 3

Mol. Weight: 1355.48 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4CCCOC4

Level: 3

Mol. Weight: 1355.48 g/mol

Structure

SMILES: O1CCCCC1OC2C(OC3CCCCO3)COC(C2)OC4CCCOC4

Level: 3

Mol. Weight: 1355.48 g/mol

Structure

SMILES: C1OCCCC1OC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1355.48 g/mol

Structure

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

Level: 2

Mol. Weight: 1355.48 g/mol

Structure

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

Level: 2

Mol. Weight: 1355.48 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1355.48 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1355.48 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1355.48 g/mol

Structure

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

Level: 1

Mol. Weight: 1355.48 g/mol

Structure

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

Level: 1

Mol. Weight: 1355.48 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1355.48 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1355.48 g/mol

Structure

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

Level: 0

Mol. Weight: 1355.48 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1355.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.04
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
758182091130510.2
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
99085459954959490

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
38.17
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.48
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-2304503561285318.0
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-940956011.69
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
-179835337893234930000
Rat (Acute)
144953.43
Rat (Chronic Oral)
385731051535.63
Fathead Minnow
227003899535937950
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
20226492762223747000
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-11243911351443.367
Log(P)
-1308923937.41
Log S
-2.63
Log(Vapor Pressure)
-666048007485430000
Melting Point
-202388129589.65
pKa Acid
-4853211494583513.0
pKa Basic
-39043930281578.09

No predicted protein targets found for this compound.

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