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Lotoside II

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

Canonical Smiles	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC[C@H]3[C@@]2(C)[C@@H](O)[C@]2([C@@H]3[C@@](C)(O)[C@H](O2)CC=C(C)C)O)C)C)[C@@H]([C@H]([C@@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI	InChI=1S/C48H80O19/c1-20(2)10-13-28-47(9,59)38-22-11-12-26-44(6)16-15-27(43(4,5)25(44)14-17-45(26,7)46(22,8)42(58)48(38,60)67-28)64-41-37(66-39-34(56)32(54)29(51)21(3)61-39)36(31(53)24(19-50)63-41)65-40-35(57)33(55)30(52)23(18-49)62-40/h10,21-42,49-60H,11-19H2,1-9H3/t21-,22+,23+,24+,25-,26+,27-,28+,29-,30+,31+,32+,33-,34+,35+,36-,37+,38-,39-,40-,41-,42+,44-,45+,46-,47-,48+/m0/s1
InChIKey	YTOUOWGIWWJGTJ-LDBMYNQJSA-N
Formula	C₄₈H₈₀O₁₉
HBA	19
HBD	12
MW	961.15
Rotatable Bonds	10
TPSA	307.37
LogP	-0.69
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	67
Formal Charge	0
Fraction CSP3	0.96
Exact Mass	960.53
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: 102066552

Nmrshiftdb2: 70066761

No compound-protein relationship available.

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC6OCCC(OC7CCCCO7)C6OC8CCCCO8

Level: 3

Mol. Weight: 961.15 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC7CCCCO7

Level: 2

Mol. Weight: 961.15 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC(OCC6)CC6OC7CCCCO7

Level: 2

Mol. Weight: 961.15 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 961.15 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CC(CC5)OC6CCCCO6

Level: 1

Mol. Weight: 961.15 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 961.15 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 961.15 g/mol

SMILES: C1COC2CC(C3C12)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 961.15 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 961.15 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.48
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 4238.350
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 554753.82

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.720
Plasma Protein Binding: 80.79
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: 0.780
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -12894.790
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.630
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: -1006850039.200
Rat (Acute): 4.120
Rat (Chronic Oral): 4.490
Fathead Minnow: 1270939.100
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 113238689.060
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -43.460
Log(P): 2.34
Log S: -2.63
Log(Vapor Pressure): -3728703.91
Melting Point: 227.09
pKa Acid: -27077.73
pKa Basic: -191.13

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7828
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7384
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7059
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7047

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