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(-)-trifolirhizin

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Benzofurochromen
- Subclass: Pterocarpans

Canonical Smiles	C1C2C(c3c(O1)cc(cc3)OC1C(C(C(C(O1)CO)O)O)O)Oc1cc3c(cc21)OCO3
InChI	InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2
InChIKey	VGSYCWGXBYZLLE-UHFFFAOYSA-N
Formula	C₂₂H₂₂O₁₀
HBA	10
HBD	4
MW	446.41
Rotatable Bonds	3
TPSA	136.3
LogP	0.2
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.45
Exact Mass	446.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ononis angustissima	Leguminosae/Fabaceae	Plantae	672159

Showing of synonyms

Ghribi L, Waffo-Téguo P, et al. (2015). Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissimaL.. Bioorganic & medicinal chemistry letters, 2015, 25(18), 3825-30. [View] [PubMed]

Pubchem: 442827

Cas: 6807-83-6

Gnps: CCMSLIB00006467960

Zinc: ZINC000004098749

Kegg Ligand: C10538

Chebi: 9714

Nmrshiftdb2: 60074101

Chembl: CHEMBL454878

CPRiL: 87293

SMILES: O1COc(c2)c1cc(c23)OC4C3COc5c4ccc(c5)OC6CCCCO6

Level: 1

Mol. Weight: 446.41 g/mol

SMILES: O1COc(c2)c1cc(c23)OC4C3COc5c4cccc5

Level: 0

Mol. Weight: 446.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 446.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.13
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.61
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.61

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.3
Plasma Protein Binding: 23.47
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: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.42
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.7
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.55
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.75
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: -233.23
Rat (Acute): 2.35
Rat (Chronic Oral): 2.94
Fathead Minnow: 4.81
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: 517.38
Hydration Free Energy: -3.15
Log(D) at pH=7.4: 1.79
Log(P): 0.59
Log S: -3.26
Log(Vapor Pressure): -12.67
Melting Point: 210.76
pKa Acid: 9.51
pKa Basic: 1.83

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.9404
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9265
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9131
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8898
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8895
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8894
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8827
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8816
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8708
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8578
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8453
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.8394
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8340
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8307
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8291
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.8156
IAG-nucleoside hydrolase	Q9GPQ4	Q9GPQ4_TRYVI	Trypanosoma vivax	4	0.8130
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8086
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8009
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7918
Isoflavone 4'-O-methyltransferase	Q29U70	I4OMT_MEDTR	Medicago truncatula	4	0.7901
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7899
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7820
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.7784
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7715
Beta-glucosidase 1A	Q25BW5	BGL1A_PHACH	Phanerodontia chrysosporium	3	0.7663
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7653
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7651
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	3	0.7578
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7572
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7557
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.7506
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7489
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7489
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7482
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7478
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7459
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7402
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7385
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7372
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7367
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7341
Matrix metalloproteinase-9	P14780	MMP9_HUMAN	Homo sapiens	3	0.7305
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7286
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7285
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7283
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7274
Calmodulin-domain protein kinase 1, putative	A3FQ16	A3FQ16_CRYPI	Cryptosporidium parvum	3	0.7267
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7253
NmrA-like family domain-containing protein 1	Q9HBL8	NMRL1_HUMAN	Homo sapiens	2	0.7242
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7219
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7217
tRNA (adenine(9)-N1)-methyltransferase	Q4J894	TRM10_SULAC	Sulfolobus acidocaldarius	3	0.7206
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7205
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7182
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7178
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7177
Macrophage colony-stimulating factor 1 receptor	P07333	CSF1R_HUMAN	Homo sapiens	3	0.7169
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7155
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7150
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7142
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7142
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7104
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7085
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7076
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7070
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7057
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7043
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	3	0.7042
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7033

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