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3-O-[beta-D-glucopyranosyl (1→2)-alpha-L-arabinopyranosyl] 27-hydroxy oleanolic acid 28-O-[beta-D-glucopyranosyl (1→6)-beta-D-glucopyranosyl] ester

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

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2[C@H](OC[C@H]([C@H]2O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(CO)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)OC[C@H]2O[C@@H](OC[C@H]3O[C@@H](O)[C@@H]([C@H]([C@@H]3O)O)O)[C@@H]([C@H]([C@@H]2O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C53H86O23/c1-48(2)13-14-52(47(68)71-21-28-35(60)38(63)40(65)44(74-28)70-20-27-34(59)36(61)39(64)43(67)72-27)15-16-53(22-55)23(24(52)17-48)7-8-30-50(5)11-10-31(49(3,4)29(50)9-12-51(30,53)6)75-46-42(32(57)25(56)19-69-46)76-45-41(66)37(62)33(58)26(18-54)73-45/h7,24-46,54-67H,8-22H2,1-6H3/t24-,25+,26+,27+,28+,29-,30+,31-,32+,33+,34+,35+,36-,37-,38-,39+,40+,41+,42-,43+,44+,45-,46+,50-,51+,52-,53-/m0/s1
InChIKey	ZENHYSQFAMFGDC-FRGLBEGHSA-N
Formula	C₅₃H₈₆O₂₃
HBA	23
HBD	14
MW	1091.25
Rotatable Bonds	12
TPSA	374.13
LogP	-2.42
Number Rings	9
Number Aromatic Rings	0
Heavy Atom Count	76
Formal Charge	0
Fraction CSP3	0.94
Exact Mass	1090.56
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fagonia cretica	Zygophyllaceae	Plantae	90528

Showing of synonyms

Abdel-Kader M, Omar A, et al. (2000). Triterpenoid saponins from Fagonia cretica. Phytochemistry,2000,54(8),853-9. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1COC(O2)CCCC2COC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC(OCCC8)C8OC9CCCCO9

Level: 4

Mol. Weight: 1091.25 g/mol

SMILES: O1CCCCC1COC(O2)CCCC2COC(=O)C34C(CCCC4)C=5C(CC3)C6C(CC5)C7C(CC6)CC(CC7)OC8CCCCO8

Level: 3

Mol. Weight: 1091.25 g/mol

SMILES: O1CCCCC1COC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8

Level: 3

Mol. Weight: 1091.25 g/mol

SMILES: C1CCCC(CC2)C1C(CC3)C2C(CC4)C=3C(CCCC5)C45C(=O)OCC6CCCC(O6)OCC7CCCCO7

Level: 2

Mol. Weight: 1091.25 g/mol

SMILES: O1CCCCC1COC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 2

Mol. Weight: 1091.25 g/mol

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

Level: 2

Mol. Weight: 1091.25 g/mol

SMILES: O1CCCCC1COC(=O)C23C(CCCC3)C=4C(CC2)C5C(CC4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 1091.25 g/mol

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

Level: 1

Mol. Weight: 1091.25 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1091.25 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1091.25 g/mol

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

Level: 0

Mol. Weight: 1091.25 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1091.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.5
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 402339.510
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 52581973.76

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.630
Plasma Protein Binding: 75.39
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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 1.320
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -1222929.540
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.160
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: -95433751788.940
Rat (Acute): 4.100
Rat (Chronic Oral): 205.000
Fathead Minnow: 120464854.410
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 10733646593.280
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -5955.110
Log(P): -1.28
Log S: -2.51
Log(Vapor Pressure): -353453344.78
Melting Point: 267.95
pKa Acid: -2575368.27
pKa Basic: -20706.11

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7730
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7239

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