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Parvispinoside C

Family: Plantae - Zygophyllaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Megastigmane Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](OCC(/C=C/[C@@]2(O)C(=CC(=O)CC2(C)C)C)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C19H30O9/c1-10-6-12(22)7-18(2,3)19(10,26)5-4-11(21)9-27-17-16(25)15(24)14(23)13(8-20)28-17/h4-6,11,13-17,20-21,23-26H,7-9H2,1-3H3/b5-4+/t11?,13-,14-,15+,16-,17-,19-/m1/s1
InChIKey	FHVQHMSEYRELEM-LVDJNBDXSA-N
Formula	C₁₉H₃₀O₉
HBA	9
HBD	6
MW	402.44
Rotatable Bonds	6
TPSA	156.91
LogP	-1.6
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.74
Exact Mass	402.19
Number of Lipinski Rule Violations	1

#	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: 11538626

Cas: 869300-23-2

Nmrshiftdb2: 70120575

Chembl: CHEMBL463352

No compound-protein relationship available.

SMILES: O=C1C=CC(CC1)C=CCCOC2CCCCO2

Level: 1

Mol. Weight: 402.44 g/mol

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 402.44 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 402.44 g/mol

Antiproliferative

Absorption

Caco-2 (logPapp): -5.39
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.150
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.25

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.670
Plasma Protein Binding: 53.69
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 2.520
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.500
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.970
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.290
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: -8.110
Rat (Acute): 2.500
Rat (Chronic Oral): 3.230
Fathead Minnow: 3.720
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 487.100
Hydration Free Energy: -15.960
Log(D) at pH=7.4: -0.180
Log(P): -1.81
Log S: -1.06
Log(Vapor Pressure): -13.19
Melting Point: 144.04
pKa Acid: 5.33
pKa Basic: 6.35

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8540
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8540
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7839
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7839
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7836
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7836
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7735
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7735
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7664
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7664
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7549
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7549
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7308
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7308
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7204
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7204
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7133
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7133
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7114
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7114
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7015
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7015

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