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Chrysophanein

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

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc(C)cc3c2C(=O)c2c(C3=O)cccc2O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C21H20O9/c1-8-5-10-15(18(26)14-9(16(10)24)3-2-4-11(14)23)12(6-8)29-21-20(28)19(27)17(25)13(7-22)30-21/h2-6,13,17,19-23,25,27-28H,7H2,1H3/t13-,17-,19+,20-,21-/m1/s1
InChIKey	QKPDYSSHOSPOKH-JNHRPPPUSA-N
Formula	C₂₁H₂₀O₉
HBA	9
HBD	5
MW	416.38
Rotatable Bonds	3
TPSA	153.75
LogP	-0.35
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	416.11
Number of Lipinski Rule Violations	0

#	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: 6324923

Cas: 4839-60-5

Zinc: ZINC000026990660

Chebi: 191585

Nmrshiftdb2: 70003875

Chembl: CHEMBL112709

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 416.38 g/mol

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

Level: 0

Mol. Weight: 416.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 416.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.49
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.020
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.9

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.950
Plasma Protein Binding: 87.77
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: 8.700
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.640
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.910
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.810
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: -28.600
Rat (Acute): 2.770
Rat (Chronic Oral): 4.000
Fathead Minnow: 4.270
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: 519.820
Hydration Free Energy: -8.490
Log(D) at pH=7.4: 0.690
Log(P): 1.34
Log S: -3.53
Log(Vapor Pressure): -11.38
Melting Point: 193.22
pKa Acid: 4.62
pKa Basic: 4.73

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	0.9655
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.9572
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9356
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8765
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8712
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8639
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8107
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8072
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7906
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	3	0.7842
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7807
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7708
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7677
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7480
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7439
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7423
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7406
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7353
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7314
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7244
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7218
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7216
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7131
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7107
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7065
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7040

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