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Gitonin

Family: Plantae - Zygophyllaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Spirostanol Saponin

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2C[C@@H]3CC[C@@H]4[C@@H]([C@]3(C[C@H]2O)C)CC[C@]2([C@H]4C[C@H]3[C@@H]2[C@@H]([C@]2(O3)CC[C@H](CO2)C)C)C)[C@@H]([C@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)O)O)O
InChI	InChI=1S/C50H82O23/c1-19-7-10-50(65-17-19)20(2)32-28(73-50)12-24-22-6-5-21-11-27(25(54)13-49(21,4)23(22)8-9-48(24,32)3)66-45-40(63)37(60)41(31(16-53)69-45)70-47-43(72-46-39(62)36(59)34(57)29(14-51)67-46)42(35(58)30(15-52)68-47)71-44-38(61)33(56)26(55)18-64-44/h19-47,51-63H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24+,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-/m1/s1
InChIKey	AULWDENWMBJIIQ-KFRXWHRXSA-N
Formula	C₅₀H₈₂O₂₃
HBA	23
HBD	13
MW	1051.18
Rotatable Bonds	11
TPSA	355.29
LogP	-3.3
Number Rings	10
Number Aromatic Rings	0
Heavy Atom Count	73
Formal Charge	0
Fraction CSP3	1.0
Exact Mass	1050.52
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tribulus parvispinus	Zygophyllaceae	Plantae	2603131

Showing of synonyms

Perrone A, Plaza A, et al. (2005). Cytotoxic furostanol saponins and a megastigmane glucoside from Tribulus parvispinus. Journal of Natural Products,2005,68(10),1549-1553. [View] [PubMed]

Pubchem: 441888

Cas: 39937-47-8

Kegg Ligand: C08900

Chebi: 5364

No compound-protein relationship available.

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8OCCC(OC9CCCCO9)C8OC1CCCCO1

Level: 4

Mol. Weight: 1051.18 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCCC8)C8OC9CCCCO9

Level: 3

Mol. Weight: 1051.18 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC(OCC8)CC8OC9CCCCO9

Level: 3

Mol. Weight: 1051.18 g/mol

SMILES: O1CCCCC1OC2C(OC3CCCCO3)CCOC2OC4CCCOC4

Level: 3

Mol. Weight: 1051.18 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(CC5)CC(CC6)OC(OC7)CCC7OC8CCCCO8

Level: 2

Mol. Weight: 1051.18 g/mol

SMILES: O1CCCCC1OC2CC(OCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1051.18 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 1051.18 g/mol

SMILES: O1CCCCC1OC2C(COCC2)OC3CCCCO3

Level: 2

Mol. Weight: 1051.18 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 1

Mol. Weight: 1051.18 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1051.18 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1051.18 g/mol

SMILES: O1CCCCC12CC3C4C(CC3O2)C5C(CC4)C6C(CC5)CCCC6

Level: 0

Mol. Weight: 1051.18 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1051.18 g/mol

Antiproliferative

Absorption

Caco-2 (logPapp): -6.61
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 251621.700
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 32884918.57

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.680
Plasma Protein Binding: 65.5
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: 0.490
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -764817.320
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.090
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: Toxic
NR-ER-LBD: Toxic
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -59684537538.510
Rat (Acute): 3.890
Rat (Chronic Oral): 127.090
Fathead Minnow: 75338993.540
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: 6712850365.540
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -3720.990
Log(P): -0.39
Log S: -1.95
Log(Vapor Pressure): -221050592.2
Melting Point: 170.57
pKa Acid: -1610612.09
pKa Basic: -12941.59

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.8024
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.8024
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7661
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7661
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7428
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7428
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7183
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7183
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7105
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7105
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7091
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7091

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