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5,7-dihydroxy-4'-methoxy-2''-(2'''-hydroxyisopropyl)-dihydrofurano-[4'',5'':3',2']-isoflavanone

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

Canonical Smiles	COc1ccc(c2c1CC(O2)C(O)(C)C)[C@H]1COc2c(C1=O)c(O)cc(c2)O
InChI	InChI=1S/C21H22O7/c1-21(2,25)17-8-12-15(26-3)5-4-11(20(12)28-17)13-9-27-16-7-10(22)6-14(23)18(16)19(13)24/h4-7,13,17,22-23,25H,8-9H2,1-3H3/t13-,17?/m1/s1
InChIKey	RMTZLMXSFDXFBI-FWJOYPJLSA-N
Formula	C₂₁H₂₂O₇
HBA	7
HBD	3
MW	386.4
Rotatable Bonds	3
TPSA	105.45
LogP	2.54
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	386.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Platycelyphium voënse	Leguminosae/Fabaceae	Plantae	149667

Showing of synonyms

Gumula I, Heydenreic M, et al. (2012). Four isoflavanones from the stem bark of Platycelphium voënse.. Phytochemistry Letters,2012,5(1),150–154. [View] [PubMed]

No compound-protein relationship available.

SMILES: C1COc(c12)c(ccc2)C(C3=O)COc(c34)cccc4

Level: 1

Mol. Weight: 386.4 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 386.4 g/mol

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 386.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.99
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.830
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.67

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.120
Plasma Protein Binding: 72.65
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: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.080
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.780
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.580
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.470
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: Toxic
T. Pyriformis: -8.160
Rat (Acute): 2.170
Rat (Chronic Oral): 2.440
Fathead Minnow: 4.550
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 469.760
Hydration Free Energy: -8.220
Log(D) at pH=7.4: 2.350
Log(P): 3.17
Log S: -5.36
Log(Vapor Pressure): -8.97
Melting Point: 212.51
pKa Acid: 7.51
pKa Basic: 5.38

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9261
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9261
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9201
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9201
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.9191
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.9191
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.9075
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.9075
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8881
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8881
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8837
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8837
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8772
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8772
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8762
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8762
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8746
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8746
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8592
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8592
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	4	0.8402
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	4	0.8402
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8391
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8391
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	4	0.8302
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	4	0.8302
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8277
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8277
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7954
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7954
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7808
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7808
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7795
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7795
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7794
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7794
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7793
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7793
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7761
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7761
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7710
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7710
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7697
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7697
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7674
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7674
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7664
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7664
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7599
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7599
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7566
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7566
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7534
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7534
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7459
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7459
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7430
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7430
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7391
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7391
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7346
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7346
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7301
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7301
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7296
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7296
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7288
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7288
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7263
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7263
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7241
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7241
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7229
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7229
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7224
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7224
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7219
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7219
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7211
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7211
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7174
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7174
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7135
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7135
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7133
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7133
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7129
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7129
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7115
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7115
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7109
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7109
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7096
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7096
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	3	0.7059
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	3	0.7059

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