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Gypsogenin 3-O-beta-xylopyranosyl-(1→3)-[beta-galactopyranosyl-(1→2)]-beta-glucuronopyranoside

Family: Plantae - Caryophyllaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Triterpenoid Saponin

Canonical Smiles	OC[C@H]1OC(O[C@H]2CC[C@]3(C([C@]2(C)C=O)CC[C@@]2(C3CC=C3[C@@]2(C)CC[C@@]2(C3CC(C)(C)CC2)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)OC1OC[C@H]([C@@H]([C@H]1O)O)O)OC1OC[C@@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C46H72O17/c1-41(2)13-15-46(40(56)57)16-14-44(5)22(23(46)17-41)7-8-28-42(3)11-10-29(43(4,21-48)27(42)9-12-45(28,44)6)61-39-36(63-38-34(55)31(52)25(50)20-59-38)35(32(53)26(18-47)60-39)62-37-33(54)30(51)24(49)19-58-37/h7,21,23-39,47,49-55H,8-20H2,1-6H3,(H,56,57)/t23?,24-,25+,26-,27?,28?,29+,30+,31+,32-,33-,34-,35+,36-,37?,38?,39?,42+,43+,44-,45-,46+/m1/s1
InChIKey	UPVBOTROXSEDBF-PQBOMDDGSA-N
Formula	C₄₆H₇₂O₁₇
HBA	16
HBD	9
MW	897.07
Rotatable Bonds	9
TPSA	271.59
LogP	1.16
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	63
Formal Charge	0
Fraction CSP3	0.91
Exact Mass	896.48
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Silene cucubalus	Caryophyllaceae	Plantae	3573

Showing of synonyms

Larhsini M, Marston A, et al. (2003). Triterpenoid saponins from the roots of Silene cucubalus. Fitoterapia,2003,74(3),237-241. [View] [PubMed]

Pubchem: 162922002

No compound-protein relationship available.

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC6OCCC(OC7CCCCO7)C6OC8CCCCO8

Level: 3

Mol. Weight: 897.07 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCCC6)C6OC7CCCCO7

Level: 2

Mol. Weight: 897.07 g/mol

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(CC5)OC(OCC6)CC6OC7CCCCO7

Level: 2

Mol. Weight: 897.07 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 897.07 g/mol

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

Level: 1

Mol. Weight: 897.07 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 897.07 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 897.07 g/mol

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

Level: 0

Mol. Weight: 897.07 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 897.07 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.09
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 832.07
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 109563.06

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.8
Plasma Protein Binding: 73.55
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: 1.41
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -2544.67
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.01
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.44
Micronucleos: Safe
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: -198850847.76
Rat (Acute): 3.5
Rat (Chronic Oral): 4.45
Fathead Minnow: 251012.87
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 22361285.0
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -1.19
Log(P): 2.04
Log S: -3.07
Log(Vapor Pressure): -736207.97
Melting Point: 252.45
pKa Acid: -5294.39
pKa Basic: -7.24

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8280
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8280
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7933
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7933
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7090
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7090

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