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Cynarasaponin A

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Saponin

Canonical Smiles	OC[C@H]1O[C@@H](OC(=O)[C@@]23CC[C@H]([C@@H]([C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H](C2(C)C)O[C@@H]2O[C@H](C(=O)O)[C@H]([C@@H]([C@H]2O[C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C47H74O18/c1-20-10-15-47(42(59)65-40-35(56)31(52)30(51)24(18-48)61-40)17-16-45(6)22(28(47)21(20)2)8-9-26-44(5)13-12-27(43(3,4)25(44)11-14-46(26,45)7)62-41-37(33(54)32(53)36(63-41)38(57)58)64-39-34(55)29(50)23(49)19-60-39/h8,20-21,23-37,39-41,48-56H,9-19H2,1-7H3,(H,57,58)/t20-,21+,23+,24-,25+,26-,27+,28+,29+,30-,31+,32+,33+,34-,35-,36+,37-,39+,40+,41-,44+,45-,46-,47+/m1/s1
InChIKey	FQCJADRURROYGR-SYEDVUJHSA-N
Formula	C₄₇H₇₄O₁₈
HBA	17
HBD	10
MW	927.09
Rotatable Bonds	8
TPSA	291.82
LogP	0.73
Number Rings	8
Number Aromatic Rings	0
Heavy Atom Count	65
Formal Charge	0
Fraction CSP3	0.91
Exact Mass	926.49
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cynara cardunculus	Asteraceae	Plantae	4265

Showing of synonyms

Farag MA, El-Ahmady SH, et al. (2013). Metabolomics driven analysis of artichoke leaf and its commercial products via UHPLC–q-TOF-MS and chemometrics. Phytochemistry,2013,95,177-187. [View] [PubMed]

Pubchem: 101027461

Zinc: ZINC000255209708

Nmrshiftdb2: 70019513

No compound-protein relationship available.

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 927.09 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 2

Mol. Weight: 927.09 g/mol

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

Level: 2

Mol. Weight: 927.09 g/mol

SMILES: O1CCCCC1OC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 927.09 g/mol

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

Level: 1

Mol. Weight: 927.09 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 927.09 g/mol

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

Level: 0

Mol. Weight: 927.09 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 927.09 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.13
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 1961.070
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 257145.94

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.930
Plasma Protein Binding: 94.83
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: 0.840
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -5975.730
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.320
Liver Injury II: Safe
hERG Blockers: Safe
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: -466706766.270
Rat (Acute): 3.240
Rat (Chronic Oral): 4.800
Fathead Minnow: 589123.180
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: 52487147.860
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -11.570
Log(P): 2.12
Log S: -2.94
Log(Vapor Pressure): -1728217.3
Melting Point: 276.75
pKa Acid: -12514.39
pKa Basic: -72.17

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9349
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9349
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8912
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8912
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7802
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7802

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