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(-)-semiglabrin

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	CC(=O)O[C@H]1[C@H]2[C@@H](OC1(C)C)Oc1c2c2oc(cc(=O)c2cc1)c1ccccc1
InChI	InChI=1S/C23H20O6/c1-12(24)26-21-19-18-16(28-22(19)29-23(21,2)3)10-9-14-15(25)11-17(27-20(14)18)13-7-5-4-6-8-13/h4-11,19,21-22H,1-3H3/t19-,21-,22+/m0/s1
InChIKey	XTIQPKJOGKMOSY-ILWGZMRPSA-N
Formula	C₂₃H₂₀O₆
HBA	6
HBD	0
MW	392.41
Rotatable Bonds	2
TPSA	74.97
LogP	4.0
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	392.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tephrosia purpurea	Leguminosae/Fabaceae	Plantae	228354

Showing of synonyms

Juma WP, Akala HM, et al. (2011). Terpurinflavone: An antiplasmodial flavone from the stem of Tephrosia Purpurea.. Phytochemistry Letters,2011,4(2),176-178. [View] [PubMed]

Pubchem: 11741220

Zinc: ZINC000005712023

Nmrshiftdb2: 80003743

Chembl: CHEMBL377111

No compound-protein relationship available.

SMILES: O1CCC2C1Oc(c23)ccc4c3oc(cc4=O)-c5ccccc5

Level: 1

Mol. Weight: 392.41 g/mol

SMILES: O1CCC2C1Oc(c23)ccc4c3occc4=O

Level: 0

Mol. Weight: 392.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 392.41 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp): -4.87
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.5
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.12

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.4
Plasma Protein Binding: 94.21
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: 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: 7.25
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.77
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.39
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.89
Micronucleos: Toxic
NR-AhR: Toxic
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: -27.06
Rat (Acute): 3.46
Rat (Chronic Oral): 1.36
Fathead Minnow: 5.02
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 481.59
Hydration Free Energy: -5.14
Log(D) at pH=7.4: 3.66
Log(P): 3.93
Log S: -5.14
Log(Vapor Pressure): -8.8
Melting Point: 179.06
pKa Acid: 8.86
pKa Basic: 3.01

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9298
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9298
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8800
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8800
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8757
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8757
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8550
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8550
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8514
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8514
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8355
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8355
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8154
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8154
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8125
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8125
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8041
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8041
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7967
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7967
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7856
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7856
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7620
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7620
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7595
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7595
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	4	0.7583
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	4	0.7583
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7519
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7519
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7484
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7484
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7482
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7482
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7444
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7444
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7398
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7398
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7383
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7383
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7352
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7352
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7328
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7328
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7320
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7320
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7204
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7204
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7192
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7192
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7187
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7187
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7184
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7184
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7181
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7181
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7154
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7154
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	4	0.7138
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	4	0.7138
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7100
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7100
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7087
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7087
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7060
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7060
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7055
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7055
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7039
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7039
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7026
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7026
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	3	0.7017
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	3	0.7017

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