3-O-(beta-D-apiofuranosyl-(1→4)-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)-alpha-L-arabinopyranosyl protobassic acid - Compound Card

3-O-(beta-D-apiofuranosyl-(1→4)-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)-alpha-L-arabinopyranosyl protobassic acid

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3-O-(beta-D-apiofuranosyl-(1→4)-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)-alpha-L-arabinopyranosyl protobassic acid

Structure
Zoomed Structure
  • Family: Plantae - Sapotaceae
  • Kingdom: Plantae
  • Class: Saponin
    • Subclass: Triterpenoid Saponin
Canonical Smiles OCC1O[C@@H](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](C2O[C@@H]2OC(C)[C@@H]([C@@H](C2O)O[C@@H]2OC(C)[C@@H](C([C@@H]2O)O)O)O[C@@H]2OC[C@H]([C@@H](C2O)O[C@@H]2OC(C)[C@@H]([C@@H](C2O)O)O)O)O)O)C)C)[C@H](C([C@@H]1O[C@H]1OC[C@](C1O)(O)CO)O)O
InChI InChI=1S/C69H112O35/c1-25-36(77)39(80)42(83)56(94-25)99-48-33(76)21-91-55(45(48)86)98-47-27(3)96-59(46(87)50(47)101-57-43(84)40(81)37(78)26(2)95-57)102-51-38(79)32(75)20-92-60(51)104-62(89)68-14-12-63(4,5)16-29(68)28-10-11-35-64(6)17-31(74)54(65(7,22-71)52(64)30(73)18-67(35,9)66(28,8)13-15-68)103-58-44(85)41(82)49(34(19-70)97-58)100-61-53(88)69(90,23-72)24-93-61/h10,25-27,29-61,70-88,90H,11-24H2,1-9H3/t25?,26?,27?,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+,58+,59+,60+,61-,64-,65+,66-,67-,68+,69-/m1/s1
InChIKey UHZVMBJPPXNWAV-WJQKZPDMSA-N
Formula C69H112O35
HBA 35
HBD 20
MW 1501.62
Rotatable Bonds 17
TPSA 550.89
LogP -6.65
Number Rings 12
Number Aromatic Rings 0
Heavy Atom Count 104
Formal Charge 0
Fraction CSP3 0.96
Exact Mass 1500.7
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: O1CCCCC1OC2CC(OCC2)OC(C3OC4CCCCO4)COC(C3)OC5C(OCCC5)OC(=O)C67C(CCCC7)C=8C(CC6)C9C(CC8)C1C(CC9)CC(CC1)OC(OC1)CCC1OC1CCCO1

Level: 7

Mol. Weight: 1501.62 g/mol

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: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4C(OCCC4)OC(=O)C56C(CCCC6)C=7C(CC5)C8C(CC7)C9C(CC8)CC(CC9)OC(OC1)CCC1OC1CCCO1

Level: 6

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2C(OC3CCCCO3)COC(C2)OC4C(OCCC4)OC(=O)C56C(CCCC6)C=7C(CC5)C8C(CC7)C9C(CC8)CC(CC9)OC(OC1)CCC1OC1CCCO1

Level: 6

Mol. Weight: 1501.62 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: 1501.62 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: 1501.62 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: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3C(OCCC3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)CC(CC8)OC(OC9)CCC9OC1CCCO1

Level: 5

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3C(OCCC3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)CC(CC8)OC(OC9)CCC9OC1CCCO1

Level: 5

Mol. Weight: 1501.62 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: 1501.62 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: 1501.62 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: 1501.62 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: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2C(OCCC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC(OC8)CCC8OC9CCCO9

Level: 4

Mol. Weight: 1501.62 g/mol

Structure

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

Level: 4

Mol. Weight: 1501.62 g/mol

Structure

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

Level: 3

Mol. Weight: 1501.62 g/mol

Structure

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

Level: 3

Mol. Weight: 1501.62 g/mol

Structure

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

Level: 3

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8CCCO8

Level: 3

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4CCCOC4

Level: 3

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2C(OC3CCCCO3)COC(C2)OC4CCCOC4

Level: 3

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1501.62 g/mol

Structure

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

Level: 2

Mol. Weight: 1501.62 g/mol

Structure

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

Level: 2

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCC1OC2CCC(OC2)OC(CC3)CC(CC4)C3C(CC5)C4C(C=56)CCC7C6CCCC7

Level: 2

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1501.62 g/mol

Structure

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

Level: 1

Mol. Weight: 1501.62 g/mol

Structure

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

Level: 1

Mol. Weight: 1501.62 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1501.62 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1501.62 g/mol

Structure

SMILES: O1CCCC1OC2CCCOC2

Level: 1

Mol. Weight: 1501.62 g/mol

Structure

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

Level: 0

Mol. Weight: 1501.62 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1501.62 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 1501.62 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.04
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
166338350747081700000
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
21738467431856504000000

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.42
Plasma Protein Binding
32.69
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
1.54
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Safe
Bioconcentration Factor
-505587530052983900000
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-206437372576616.4
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
-39454265789172175000000000
Rat (Acute)
31818226959.68
Rat (Chronic Oral)
84625955340454030
Fathead Minnow
49802661380303740000000
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
4437512159323517000000000
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-2466813664107063000
Log(P)
-287166231193559.5
Log S
-2.32
Log(Vapor Pressure)
-146125014224652170000000
Melting Point
-44402147928117940
pKa Acid
-1064750904995429700000
pKa Basic
-8565889833230195000

No predicted protein targets found for this compound.

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