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Glucofrangulin A diacetate

Family: Rhamnaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthraquinone Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc(O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3OC(=O)C)OC(=O)C)O)cc3c2C(=O)c2c(C3=O)cc(cc2O)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C31H34O16/c1-10-5-15-20(17(35)6-10)25(39)21-16(23(15)37)7-14(8-18(21)46-30-27(41)26(40)24(38)19(9-32)47-30)45-31-29(44-13(4)34)28(43-12(3)33)22(36)11(2)42-31/h5-8,11,19,22,24,26-32,35-36,38,40-41H,9H2,1-4H3/t11-,19+,22-,24+,26-,27+,28+,29+,30+,31-/m0/s1
InChIKey	NFSJRTKXBTYHAZ-RNSHHGLOSA-N
Formula	C₃₁H₃₄O₁₆
HBA	16
HBD	6
MW	662.6
Rotatable Bonds	7
TPSA	245.04
LogP	-1.0
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	47
Formal Charge	0
Fraction CSP3	0.48
Exact Mass	662.18
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rhamnus prinoides	Rhamnaceae	Plantae	280022

Showing of synonyms

Bezabih M, Abegaz BM. (1998). Glucofrangulin A diacetate from the fruits of Rhamnus prinoides. Bulletin of the Chemical Society of Ethiopia,1998,12(1),45-48. [View] [PubMed]

Pubchem: 102404309

No compound-protein relationship available.

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cc(OC4CCCCO4)cc3OC5CCCCO5

Level: 2

Mol. Weight: 408.45 g/mol

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3OC4CCCCO4

Level: 1

Mol. Weight: 308.33 g/mol

SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)OC4CCCCO4

Level: 1

Mol. Weight: 308.33 g/mol

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 208.22 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.35
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.900
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 38.02

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.700
Plasma Protein Binding: 81.81
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: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.540
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.560
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.020
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.390
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -70206.840
Rat (Acute): 3.110
Rat (Chronic Oral): 4.450
Fathead Minnow: 104.650
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 1793.410
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 0.360
Log(P): 0.95
Log S: -3.53
Log(Vapor Pressure): -100.73
Melting Point: 210.55
pKa Acid: 4.68
pKa Basic: 0.42

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9029
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9029
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8511
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8511
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8262
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8262
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.8237
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.8237
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8214
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8214
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.8200
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.8200
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8138
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8138
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8136
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8136
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8021
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8021
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7611
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7611
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7391
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7391
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7359
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7359
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7293
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7293
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7245
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7245
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7226
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7226
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7194
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7194
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7133
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7133
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7124
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7124
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7051
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7051
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7015
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7015

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