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Gluco-chrysoobtusin

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthraquinone Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2c(C)cc3c(c2OC)C(=O)c2c(C3=O)cc(c(c2OC)OC)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C25H28O12/c1-9-6-10-14(18(29)15-11(16(10)27)7-12(32-2)22(33-3)24(15)35-5)23(34-4)21(9)37-25-20(31)19(30)17(28)13(8-26)36-25/h6-7,13,17,19-20,25-26,28,30-31H,8H2,1-5H3/t13-,17-,19+,20-,25+/m1/s1
InChIKey	QBFJCZWBSLFTEE-UWBHIVAPSA-N
Formula	C₂₅H₂₈O₁₂
HBA	12
HBD	4
MW	520.49
Rotatable Bonds	7
TPSA	170.44
LogP	-0.02
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	37
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	520.16
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cassia obtusifolia	Leguminosae/Fabaceae	Plantae	346985

Showing of synonyms

Sob S, Wabo H, et al. (2010). Anthraquinones, sterols, triterpenoids and xanthones from Cassia obtusifolia. Biochemical Systematics and Ecology, 2010, 38(3), 342-345. [View]

Pubchem: 442730

Cas: 96820-54-1

Zinc: ZINC000004098656

Kegg Ligand: C10313

Chebi: 3685

Nmrshiftdb2: 60076332

Chembl: CHEMBL465439

Comptox: DTXSID20331929

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 520.49 g/mol

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

Level: 0

Mol. Weight: 520.49 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 520.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.16
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.920
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.06

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.950
Plasma Protein Binding: 83.65
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: 4.200
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.540
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.790
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.130
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: -791.610
Rat (Acute): 2.710
Rat (Chronic Oral): 4.230
Fathead Minnow: 5.000
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 541.820
Hydration Free Energy: -2.870
Log(D) at pH=7.4: 0.970
Log(P): 0.29
Log S: -3.7
Log(Vapor Pressure): -10.11
Melting Point: 191.47
pKa Acid: 5.81
pKa Basic: 1.66

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9363
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9329
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9115
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9042
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.9027
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9007
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8943
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8840
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8830
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8658
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8620
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8594
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8520
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8392
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8376
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8340
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7966
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7952
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7908
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7878
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7863
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7861
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7805
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7704
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7701
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7681
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7655
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7608
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7603
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7556
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7520
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7485
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7442
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7395
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7360
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7326
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7308
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7281
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7280
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7269
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7262
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7255
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7241
D-mycarose 3-C-methyltransferase	Q194Q4	Q194Q4_STRAA	Streptomyces argillaceus	4	0.7226
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7216
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7208
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7199
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7179
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7145
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7129
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7063
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7042
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7005
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7004

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