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Glabridin

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

Canonical Smiles	Oc1ccc(c(c1)O)[C@@H]1COc2c(C1)ccc1c2C=CC(O1)(C)C
InChI	InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1
InChIKey	LBQIJVLKGVZRIW-ZDUSSCGKSA-N
Formula	C₂₀H₂₀O₄
HBA	4
HBD	2
MW	324.38
Rotatable Bonds	1
TPSA	58.92
LogP	4.0
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	324.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ormocarpum sennoides	Leguminosae/Fabaceae	Plantae	77289

Showing of synonyms

Chalo DM, Kakudidi E, et al. (2021). Chemical constituents of the roots of Ormocarpum sennoides subsp. Zanzibaricum. Biochemical Systematics and Ecology, 2021, 97,104277. [View]

Pubchem: 124052

Cas: 59870-68-7

Gnps: CCMSLIB00006419674

Zinc: ZINC000004098719

Kegg Ligand: C10421

Chebi: 5369

Nmrshiftdb2: 60059489

Chembl: CHEMBL480477

Comptox: DTXSID00208589

Pdb Ligand: GBJ

Bindingdb: 50441626

CPRiL: 56282

SMILES: C1=CCOc2ccc(c3c12)CC(CO3)c4ccccc4

Level: 1

Mol. Weight: 324.38 g/mol

SMILES: O1CCCc(c1c23)ccc2OCC=C3

Level: 0

Mol. Weight: 324.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 324.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.72
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.690
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.52

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.890
Plasma Protein Binding: 75.7
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.400
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.880
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.030
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.010
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 2.320
Rat (Acute): 2.330
Rat (Chronic Oral): 2.180
Fathead Minnow: 4.520
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 436.970
Hydration Free Energy: -10.260
Log(D) at pH=7.4: 4.290
Log(P): 4.09
Log S: -4.67
Log(Vapor Pressure): -8.37
Melting Point: 191.35
pKa Acid: 10.18
pKa Basic: 6.64

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9577
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9524
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9506
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9453
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9325
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9275
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9230
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.9229
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9220
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9209
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.9140
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9129
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9108
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9074
Endochitinase B1	Q873X9	CHIB1_ASPFM	Aspergillus fumigatus	4	0.9071
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9041
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8942
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8900
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8837
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8817
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.8798
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8787
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8750
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8747
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8734
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8723
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8720
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8705
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8664
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8538
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.8538
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8402
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8402
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.8399
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8390
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8333
Dihydrofolate reductase	O30463	O30463_MYCAV	Mycobacterium avium	4	0.8331
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.8330
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.8294
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8266
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8213
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8212
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8207
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8195
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8179
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8142
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.8134
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8125
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8097
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8090
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.8089
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.8083
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8027
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8009
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	4	0.7997
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7995
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7958
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7947
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7918
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7897
Beta-elicitin cinnamomin	P15569	ELIB_PHYCI	Phytophthora cinnamomi	3	0.7895
Dihydrofolate reductase	Q83AB2	Q83AB2_COXBU	Coxiella burnetii	4	0.7892
Thymidine phosphorylase	P07650	TYPH_ECOLI	Escherichia coli	4	0.7859
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7849
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7844
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7767
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.7760
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7742
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7727
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7713
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.7691
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7666
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7651
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7643
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7592
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7589
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7584
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7580
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.7555
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7551
Dihydrofolate reductase	Q81R22	Q81R22_BACAN	Bacillus anthracis	4	0.7543
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7543
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7541
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7516
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7508
Inorganic pyrophosphatase	Q3JUV5	Q3JUV5_BURP1	Burkholderia pseudomallei	3	0.7506
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7503
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7482
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7474
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7474
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7458
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7457
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7449
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	4	0.7441
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7440
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7416
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7387
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7371
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7355
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.7350
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7344
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7313
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7313
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7303
Dihydrofolate reductase	Q81R22	Q81R22_BACAN	Bacillus anthracis	4	0.7297
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7290
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7281
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7268
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7238
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7231
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7224
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7216
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7211
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.7205
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7186
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	3	0.7180
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7179
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7178
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7174
Cholesterol side-chain cleavage enzyme, mitochondrial	P00189	CP11A_BOVIN	Bos taurus	3	0.7155
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7150
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7150
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	5	0.7149
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7140
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.7131
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q8ZMF7	ISPF_SALTY	Salmonella typhimurium	3	0.7091
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7082
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7074
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7069
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7067
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	3	0.7049
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7040
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7026
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7025
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7009
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	3	0.7004

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