3-O-(beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1→3)-beta-D-xylopyranosyl-(1→4)[alpha-L-rhamnopyranosyl-(1→3)]-alpha-L-rhamnopyranosyl-(1→2)-beta-D-xylopyranosyl)16alpha-hydroxyprotobassic acid - Compound Card

3-O-(beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1→3)-beta-D-xylopyranosyl-(1→4)[alpha-L-rhamnopyranosyl-(1→3)]-alpha-L-rhamnopyranosyl-(1→2)-beta-D-xylopyranosyl)16alpha-hydroxyprotobassic 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→3)]-alpha-L-rhamnopyranosyl-(1→2)-beta-D-xylopyranosyl)16alpha-hydroxyprotobassic 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)C[C@H]([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)OC2O[C@@H](C)C([C@@H](C2O)O)O)O[C@@H]2OC[C@H]([C@@H](C2O)OC2O[C@@H](C)[C@@H](C([C@@H]2O)O)O)O)O)O)O)C)C)[C@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C64H104O32/c1-22-34(72)38(76)41(79)53(87-22)92-47-30(70)20-85-52(44(47)82)91-46-24(3)89-56(45(83)48(46)93-54-42(80)39(77)35(73)23(2)88-54)94-49-36(74)29(69)19-86-57(49)96-58(84)64-13-12-59(4,5)14-26(64)25-10-11-32-60(6)15-28(68)51(95-55-43(81)40(78)37(75)31(18-65)90-55)61(7,21-66)50(60)27(67)16-63(32,9)62(25,8)17-33(64)71/h10,22-24,26-57,65-83H,11-21H2,1-9H3/t22-,23-,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?,57-,60+,61-,62+,63+,64+/m0/s1
InChIKey NQBYRFIZMHJSDT-MRGCFKDVSA-N
Formula C64H104O32
HBA 32
HBD 19
MW 1385.5
Rotatable Bonds 14
TPSA 512.2
LogP -6.14
Number Rings 11
Number Aromatic Rings 0
Heavy Atom Count 96
Formal Charge 0
Fraction CSP3 0.95
Exact Mass 1384.65
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(C8)OCC(C8OC9CCCCO9)OC(OCC1)CC1OC1CCCCO1

Level: 6

Mol. Weight: 1385.5 g/mol

Structure

SMILES: O1CCCCC1OC2C(OC3CCCCO3)COC(C2)OC4C(OCCC4)OC(=O)C56C(CCCC6)C=7C(CC5)C8C(CC7)C9C(CC8)CC(CC9)OC1CCCCO1

Level: 5

Mol. Weight: 1385.5 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: 1385.5 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(C7)OCC(C7OC8CCCCO8)OC(OCC9)CC9OC1CCCCO1

Level: 5

Mol. Weight: 1385.5 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: 1385.5 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3C(OCCC3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)CC(CC8)OC9CCCCO9

Level: 4

Mol. Weight: 1385.5 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: 1385.5 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(C7)OCC(OC8CCCCO8)C7OC9CCCCO9

Level: 4

Mol. Weight: 1385.5 g/mol

Structure

SMILES: C1OCCCC1OC(C2)OCC(C2OC3CCCCO3)OC(OCC4)CC4OC5CCCCO5

Level: 4

Mol. Weight: 1385.5 g/mol

Structure

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

Level: 3

Mol. Weight: 1385.5 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCCC6)C6OC(OCC7)CC7OC8CCCCO8

Level: 3

Mol. Weight: 1385.5 g/mol

Structure

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

Level: 3

Mol. Weight: 1385.5 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4CCCOC4

Level: 3

Mol. Weight: 1385.5 g/mol

Structure

SMILES: O1CCCCC1OC2C(OC3CCCCO3)COC(C2)OC4CCCOC4

Level: 3

Mol. Weight: 1385.5 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1385.5 g/mol

Structure

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

Level: 2

Mol. Weight: 1385.5 g/mol

Structure

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

Level: 2

Mol. Weight: 1385.5 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1385.5 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1385.5 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1385.5 g/mol

Structure

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

Level: 1

Mol. Weight: 1385.5 g/mol

Structure

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

Level: 1

Mol. Weight: 1385.5 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1385.5 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1385.5 g/mol

Structure

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

Level: 0

Mol. Weight: 1385.5 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1385.5 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
2913961397270348.0
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
380820625416750500

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
33.12
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
1.87
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-8857025174990401.0
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-3616428415.18
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
-691171066441411600000
Rat (Acute)
557321.34
Rat (Chronic Oral)
1482501850490.01
Fathead Minnow
872455822225267000
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
77737589074982400000
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-43214345078413.8
Log(P)
-5030659005.18
Log S
-2.15
Log(Vapor Pressure)
-2559859345527653000
Melting Point
-777849477965.05
pKa Acid
-18652612615538160
pKa Basic
-150059697647195.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7498

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