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Libericoside A1

Family: Plantae - Polygalaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Triterpene Saponin

Canonical Smiles	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H]([C@]2(C)C(=O)O)CC[C@@]2([C@@H]3CC=C3[C@@]2(CO)CC[C@@]2([C@@H]3CC(C)(C)CC2)C(=O)O[C@@H]2O[C@H](C)[C@@H]([C@@H]([C@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O[C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)O)O)OC(=O)/C=C/c2ccc(c(c2)OC)OC)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C69H102O30/c1-30-53(96-58-52(83)55(36(73)28-90-58)97-57-48(79)44(75)35(72)27-89-57)47(78)50(81)59(91-30)98-56-51(82)54(95-43(74)15-11-32-10-13-37(87-8)38(24-32)88-9)31(2)92-61(56)99-63(86)68-21-20-64(3,4)25-34(68)33-12-14-40-65(5)18-17-42(94-60-49(80)46(77)45(76)39(26-70)93-60)67(7,62(84)85)41(65)16-19-66(40,6)69(33,29-71)23-22-68/h10-13,15,24,30-31,34-36,39-42,44-61,70-73,75-83H,14,16-23,25-29H2,1-9H3,(H,84,85)/b15-11+/t30-,31+,34+,35-,36+,39+,40+,41+,42-,44-,45+,46-,47-,48+,49+,50+,51-,52+,53-,54-,55-,56+,57-,58-,59-,60-,61-,65+,66+,67-,68-,69-/m0/s1
InChIKey	MDXOKEWRHHZBRW-GFAVHFNVSA-N
Formula	C₆₉H₁₀₂O₃₀
HBA	29
HBD	14
MW	1411.55
Rotatable Bonds	18
TPSA	454.42
LogP	-0.56
Number Rings	11
Number Aromatic Rings	1
Heavy Atom Count	99
Formal Charge	0
Fraction CSP3	0.81
Exact Mass	1410.65
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Atroxima liberica	Polygalaceae	Plantae	174495

Showing of synonyms

Tabopda TK, Mitaine-Offer A-C, et al. (2011). Acylated Triterpene Saponins from Atroxima liberica Stapf. Helvetica Chimica Acta, 2011, 94(11), 2066–2076. [View]

Pubchem: 101549200

No compound-protein relationship available.

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4C(OCC(C4)OC(=O)C=Cc5ccccc5)OC(=O)C67C(CCCC7)C=8C(CC6)C9C(CC8)C1C(CC9)CC(CC1)OC1CCCCO1

Level: 6

Mol. Weight: 1411.55 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2)COC(C2OC(OC3)CCC3OC4CCCCO4)OC(=O)C56C(CCCC6)C=7C(CC5)C8C(CC7)C9C(CC8)CC(CC9)OC1CCCCO1

Level: 5

Mol. Weight: 1411.55 g/mol

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OC(OCC(C6)OC(=O)C=Cc7ccccc7)C6OC(OC8)CCC8OC(OCC9)CC9OC1CCCCO1

Level: 5

Mol. Weight: 1411.55 g/mol

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: 1411.55 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2)COC(C2OC3CCCCO3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)CC(CC8)OC9CCCCO9

Level: 4

Mol. Weight: 1411.55 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2)COC(C2OC(OC3)CCC3OC4CCCCO4)OC(=O)C56C(CCCC6)C=7C(CC5)C8C(CC7)C9C(CC8)CCCC9

Level: 4

Mol. Weight: 1411.55 g/mol

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

Level: 4

Mol. Weight: 1411.55 g/mol

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

Level: 4

Mol. Weight: 1411.55 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(COC2)OC(OC3)CCC3OC(OCC4)CC4OC5CCCCO5

Level: 4

Mol. Weight: 1411.55 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC8CCCCO8

Level: 3

Mol. Weight: 1411.55 g/mol

SMILES: c1ccccc1C=CC(=O)OC(C2)COC(C2OC3CCCCO3)OC(=O)C45C(CCCC5)C=6C(CC4)C7C(CC6)C8C(CC7)CCCC8

Level: 3

Mol. Weight: 1411.55 g/mol

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

Level: 3

Mol. Weight: 1411.55 g/mol

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

Level: 3

Mol. Weight: 1411.55 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(COC2)OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 1411.55 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4CCCOC4

Level: 3

Mol. Weight: 1411.55 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CCCC7

Level: 2

Mol. Weight: 1411.55 g/mol

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

Level: 2

Mol. Weight: 1411.55 g/mol

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

Level: 2

Mol. Weight: 1411.55 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(COC2)OC3CCCCO3

Level: 2

Mol. Weight: 1411.55 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1411.55 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1411.55 g/mol

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

Level: 1

Mol. Weight: 1411.55 g/mol

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

Level: 1

Mol. Weight: 1411.55 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 1411.55 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1411.55 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1411.55 g/mol

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

Level: 0

Mol. Weight: 1411.55 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1411.55 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1411.55 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -6.04
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 54377312046690136.000
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 7106479718764562000

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.910
Plasma Protein Binding: 71.02
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: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 2.120
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -165280624718547616.000
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -67486055959.140
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.050
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: -12897917250434976710656.000
Rat (Acute): 10401552.560
Rat (Chronic Oral): 27664905722647.012
Fathead Minnow: 16280860036113524736.000
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 1450658045578598940672.000
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -806421289051666.750
Log(P): -93876951795.32
Log S: -3.65
Log(Vapor Pressure): -47769441105968005000
Melting Point: -14515418558491.35
pKa Acid: -348075753660628030
pKa Basic: -2800258835236680.5

No predicted protein targets found for this compound.

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