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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)protobassic acid

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)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)C)C)[C@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C64H104O31/c1-23-34(71)38(75)41(78)53(86-23)91-47-31(70)21-84-52(44(47)81)90-46-25(3)88-56(45(82)48(46)92-54-42(79)39(76)35(72)24(2)87-54)93-49-36(73)30(69)20-85-57(49)95-58(83)64-14-12-59(4,5)16-27(64)26-10-11-33-60(6)17-29(68)51(94-55-43(80)40(77)37(74)32(19-65)89-55)61(7,22-66)50(60)28(67)18-63(33,9)62(26,8)13-15-64/h10,23-25,27-57,65-82H,11-22H2,1-9H3/t23-,24-,25-,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	ZWDKGWAENWUCPE-VIPPARIISA-N
Formula	C₆₄H₁₀₄O₃₁
HBA	31
HBD	18
MW	1369.51
Rotatable Bonds	14
TPSA	491.97
LogP	-5.11
Number Rings	11
Number Aromatic Rings	0
Heavy Atom Count	95
Formal Charge	0
Fraction CSP3	0.95
Exact Mass	1368.66
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.

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: 1369.51 g/mol

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: 1369.51 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: 1369.51 g/mol

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: 1369.51 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: 1369.51 g/mol

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

Level: 4

Mol. Weight: 1369.51 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: 1369.51 g/mol

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

Level: 4

Mol. Weight: 1369.51 g/mol

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

Level: 4

Mol. Weight: 1369.51 g/mol

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

Level: 3

Mol. Weight: 1369.51 g/mol

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

Level: 3

Mol. Weight: 1369.51 g/mol

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

Level: 3

Mol. Weight: 1369.51 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCC(OC3)OC4CCCOC4

Level: 3

Mol. Weight: 1369.51 g/mol

SMILES: O1CCCCC1OC2C(OC3CCCCO3)COC(C2)OC4CCCOC4

Level: 3

Mol. Weight: 1369.51 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC(OCC3)CC3OC4CCCCO4

Level: 3

Mol. Weight: 1369.51 g/mol

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

Level: 2

Mol. Weight: 1369.51 g/mol

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

Level: 2

Mol. Weight: 1369.51 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 1369.51 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1369.51 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1369.51 g/mol

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

Level: 1

Mol. Weight: 1369.51 g/mol

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

Level: 1

Mol. Weight: 1369.51 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1369.51 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1369.51 g/mol

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

Level: 0

Mol. Weight: 1369.51 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1369.51 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: 686435324203511.5
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 89709055635285660

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.49
Plasma Protein Binding: 35.73
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: 1.55
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -2086429648301220.8
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -851914014.5
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: -162817619032047650000
Rat (Acute): 131227.03
Rat (Chronic Oral): 349229543202.36
Fathead Minnow: 205522734525937760
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: 18312469452253362000
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -10179903263119.9
Log(P): -1185061135.33
Log S: -2.6
Log(Vapor Pressure): -603020254221694600
Melting Point: -183236238597.33
pKa Acid: -4393953107297671.5
pKa Basic: -35349230063105.79

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7843
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7543

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