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Obtusifolin

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

Canonical Smiles	COc1c2c(cc(c1O)C)C(=O)c1c(C2=O)c(O)ccc1
InChI	InChI=1S/C16H12O5/c1-7-6-9-12(16(21-2)13(7)18)15(20)11-8(14(9)19)4-3-5-10(11)17/h3-6,17-18H,1-2H3
InChIKey	NYRXUBDGDSRBGB-UHFFFAOYSA-N
Formula	C₁₆H₁₂O₅
HBA	5
HBD	2
MW	284.27
Rotatable Bonds	1
TPSA	83.83
LogP	2.19
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.12
Exact Mass	284.07
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: 3083575

Cas: 477-85-0

Gnps: CCMSLIB00006460301

Zinc: ZINC000014814114

Kegg Ligand: C17039

Chebi: 80880

Nmrshiftdb2: 60072687

Chembl: CHEMBL448400

Comptox: DTXSID70197254

CPRiL: 108766

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

Level: 0

Mol. Weight: 284.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.48
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.59
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.23

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.96
Plasma Protein Binding: 63.68
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: 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: 8.17
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.14
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.03
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.55
Micronucleos: Toxic
NR-AhR: Toxic
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: 4.61
Rat (Acute): 2.51
Rat (Chronic Oral): 2.97
Fathead Minnow: 4.41
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 415.14
Hydration Free Energy: -7.61
Log(D) at pH=7.4: 2.17
Log(P): 3.43
Log S: -6.02
Log(Vapor Pressure): -7.05
Melting Point: 199.32
pKa Acid: 7.3
pKa Basic: 3.77

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	0.9733
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9396
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9129
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8892
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8859
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8839
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8671
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8608
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8542
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8419
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8414
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8413
Aklavinone 12-hydroxylase RdmE	Q54530	DNRF_STREF	Streptomyces purpurascens	4	0.8234
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8233
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8224
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8197
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	4	0.8173
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.8156
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8119
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.8045
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8002
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7943
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7942
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.7920
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7893
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7888
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7852
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	4	0.7833
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7822
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7772
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7759
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7693
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7685
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7681
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7645
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7619
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7617
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7610
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7603
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7582
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7581
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7578
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7566
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7538
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7497
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7494
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7484
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7476
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7420
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7402
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7397
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7394
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7381
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7371
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7341
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7298
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	4	0.7296
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7282
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7250
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7245
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7244
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7243
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7240
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.7219
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7211
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7205
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7199
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7189
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7189
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7179
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7135
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7131
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7128
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7125
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7122
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7119
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7117
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7104
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7099
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7097
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7090
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	2	0.7075
Scytalone dehydratase	P56221	SCYD_MAGO7	Pyricularia oryzae	3	0.7068
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7063
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7063
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7061
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7058
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7046
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7046
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7045
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7037
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7036
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7006

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