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Jujuboside A

Family: Plantae - Rhamnaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Dammarane Saponin

Canonical Smiles	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@H]3[C@@H](O)CO[C@H]([C@@H]3O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]3([C@@H]4CC[C@H]4[C@@]53CO[C@]3(C5)[C@@H]4[C@@](C)(O)C[C@@H](O3)C=C(C)C)C)C)[C@@H]([C@H]([C@@H]2O)O)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C58H94O26/c1-23(2)15-25-16-56(8,72)47-26-9-10-32-54(6)13-12-33(53(4,5)31(54)11-14-55(32,7)57(26)21-58(47,84-25)76-22-57)80-51-46(83-50-43(71)38(66)34(62)24(3)77-50)44(28(61)19-74-51)81-52-45(82-49-41(69)35(63)27(60)18-73-49)40(68)37(65)30(79-52)20-75-48-42(70)39(67)36(64)29(17-59)78-48/h15,24-52,59-72H,9-14,16-22H2,1-8H3/t24-,25-,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-,54-,55+,56-,57-,58-/m0/s1
InChIKey	KVKRFLVYJLIZFD-OQVAHBRNSA-N
Formula	C₅₈H₉₄O₂₆
HBA	26
HBD	14
MW	1207.36
Rotatable Bonds	13
TPSA	393.98
LogP	-2.72
Number Rings	11
Number Aromatic Rings	0
Heavy Atom Count	84
Formal Charge	0
Fraction CSP3	0.97
Exact Mass	1206.6
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Zizyphus lotus	Rhamnaceae	Plantae	3867

Showing of synonyms

Renault J.H, Ghedira K, et al. (1997). Dammarane saponins from Zizyphus lotus. Phytochemistry, 1997, 44(7), 1321-7. [View] [PubMed]

Pubchem: 51346169

Cas: 55466-04-1

Gnps: CCMSLIB00006511397

Chebi: 177582

Nmrshiftdb2: 60028675

CPRiL: 121747

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)OC(C4OC5CCCCO5)CCOC4OC(C6)CCC7C6CCC8C7CCC(C189)C2C(C9)(OC1)OCCC2

Level: 5

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC(C3OC4CCCCO4)CCOC3OC(C5)CCC6C5CCC7C6CCC(C789)C1C(C8)(OC9)OCCC1

Level: 4

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)OC4CC(OCC4)OC(C5)CCC6C5CCC7C6CCC(C789)C1C(C8)(OC9)OCCC1

Level: 4

Mol. Weight: 1207.36 g/mol

SMILES: C1CCOC(C2)(OC3)C1C(C234)CCC5C4CCC6C5CCC(C6)OC7OCCC(C7OC8CCCCO8)OC(OCCC9)C9OC1CCCCO1

Level: 4

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)OC4C(COCC4)OC5CCCCO5

Level: 4

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CC(OCC3)OC(C4)CCC5C4CCC6C5CCC(C678)C9C(C7)(OC8)OCCC9

Level: 3

Mol. Weight: 1207.36 g/mol

SMILES: C1CCOC(C2)(OC3)C1C(C234)CCC5C4CCC6C5CCC(C6)OC7OCCC(OC8CCCCO8)C7OC9CCCCO9

Level: 3

Mol. Weight: 1207.36 g/mol

SMILES: C1CCOC(C2)(OC3)C1C(C234)CCC5C4CCC6C5CCC(C6)OC(OCC7)CC7OC(OCCC8)C8OC9CCCCO9

Level: 3

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3C(COCC3)OC4CCCCO4

Level: 3

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)OC4CCOCC4

Level: 3

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OC(COCC2)C2OC(OCCC3)C3OC4CCCCO4

Level: 3

Mol. Weight: 1207.36 g/mol

SMILES: C1CCOC(C2)(OC3)C1C(C234)CCC5C4CCC6C5CCC(C6)OC(OCCC7)C7OC8CCCCO8

Level: 2

Mol. Weight: 1207.36 g/mol

SMILES: C1CCOC(C2)(OC3)C1C(C234)CCC5C4CCC6C5CCC(C6)OC(OCC7)CC7OC8CCCCO8

Level: 2

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CCOCC3

Level: 2

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OCC2CCC(CO2)OC3CCCCO3

Level: 2

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCOCC3

Level: 2

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1207.36 g/mol

SMILES: C1CCOC(C2)(OC3)C1C(C234)CCC5C4CCC6C5CCC(C6)OC7CCCCO7

Level: 1

Mol. Weight: 1207.36 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1207.36 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1207.36 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1207.36 g/mol

SMILES: C1CCOC(C2)(OC3)C1C(C234)CCC5C4CCC6C5CCCC6

Level: 0

Mol. Weight: 1207.36 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1207.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.52
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 16961593482.760
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 2216680999190.05

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.610
Plasma Protein Binding: 68.51
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: 0.820
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -51554997129.080
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -21050.980
Liver Injury II: Safe
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: -4023169429285126.500
Rat (Acute): 4.520
Rat (Chronic Oral): 8629345.230
Fathead Minnow: 5078395984975.740
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: 452494984933164.062
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -251542068.650
Log(P): -29281.8
Log S: -2.49
Log(Vapor Pressure): -14900435763466.787
Melting Point: -4524533.62
pKa Acid: -108573140283.65
pKa Basic: -873467595.83

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7884
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7683
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7031

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