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Gluco-aurantioobtusin

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

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc3C(=O)c4cc(C)c(c(c4C(=O)c3c(c2OC)O)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C23H24O12/c1-7-4-8-13(22(33-3)14(7)25)17(28)12-9(15(8)26)5-10(21(32-2)18(12)29)34-23-20(31)19(30)16(27)11(6-24)35-23/h4-5,11,16,19-20,23-25,27,29-31H,6H2,1-3H3/t11-,16-,19+,20-,23-/m1/s1
InChIKey	LQYQYAJWKXDTHR-PHVGODQESA-N
Formula	C₂₃H₂₄O₁₂
HBA	12
HBD	6
MW	492.43
Rotatable Bonds	5
TPSA	192.44
LogP	-0.62
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.39
Exact Mass	492.13
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: 442725

Cas: 129025-96-3

Zinc: ZINC000004098650

Kegg Ligand: C10303

Chebi: 28268

Nmrshiftdb2: 60076331

Chembl: CHEMBL464229

Comptox: DTXSID40331926

Bindingdb: 50133039

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 492.43 g/mol

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

Level: 0

Mol. Weight: 492.43 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 492.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.46
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.160
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.32

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.820
Plasma Protein Binding: 80.19
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: 10.570
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.330
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.890
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.110
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: -273.630
Rat (Acute): 2.570
Rat (Chronic Oral): 4.180
Fathead Minnow: 4.530
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: 560.250
Hydration Free Energy: -3.040
Log(D) at pH=7.4: 0.740
Log(P): 0.71
Log S: -4.62
Log(Vapor Pressure): -10.8
Melting Point: 217.41
pKa Acid: 4.45
pKa Basic: 3.74

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.9457
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8661
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8556
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8422
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8417
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8324
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8028
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8003
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7962
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7872
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7870
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7845
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7740
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7713
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7698
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7687
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7678
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7639
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7626
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7605
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7556
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7532
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7498
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7482
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7418
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7417
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7358
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7338
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7336
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7273
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7267
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7264
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7249
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7244
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7214
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7212
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7206
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7185
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7139
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	4	0.7125
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7119
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7094
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	4	0.7087
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7084
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7078
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7077
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7074
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7043
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7036
Bifunctional F420 biosynthesis protein FbiB	P9WP79	FBIB_MYCTU	Mycobacterium tuberculosis	5	0.7032
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7019

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