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Rhodimer

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

Canonical Smiles	COc1cc(OC)c(c2c1[C@@H](C[C@H](O2)c1ccccc1)c1c(O)c(CC=C(C)C)c2c(c1O)C(=O)C[C@H](O2)c1ccccc1)CC=C(C)C
InChI	InChI=1S/C42H44O7/c1-24(2)17-19-28-34(46-5)23-35(47-6)36-30(21-32(48-41(28)36)26-13-9-7-10-14-26)37-39(44)29(20-18-25(3)4)42-38(40(37)45)31(43)22-33(49-42)27-15-11-8-12-16-27/h7-18,23,30,32-33,44-45H,19-22H2,1-6H3/t30-,32+,33+/m1/s1
InChIKey	LHMWSPKXZZITTJ-JXFVGPSASA-N
Formula	C₄₂H₄₄O₇
HBA	7
HBD	2
MW	660.81
Rotatable Bonds	9
TPSA	94.45
LogP	9.49
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	49
Formal Charge	0
Fraction CSP3	0.31
Exact Mass	660.31
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tephrosia rhodesica	Leguminosae/Fabaceae	Plantae	556521

Showing of synonyms

Atilaw Y, Muiva-Mutisya L, et al. (2020). Prenylated Flavonoids from the Roots of Tephrosia rhodesica. Journal of natural products, 2020, 83(8), 2390–2398. [View]

Pubchem: 168306676

No compound-protein relationship available.

SMILES: c1ccccc1C(CC2=O)Oc(c23)ccc(c3)C4CC(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 660.81 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)ccc(c3)C4CCOc(c45)cccc5

Level: 2

Mol. Weight: 660.81 g/mol

SMILES: O=C1CCOc(c12)ccc(c2)C3CC(c4ccccc4)Oc(c35)cccc5

Level: 2

Mol. Weight: 660.81 g/mol

SMILES: O=C1CCOc(c12)ccc(c2)C3CCOc(c34)cccc4

Level: 1

Mol. Weight: 660.81 g/mol

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 660.81 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 660.81 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 660.81 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 660.81 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 660.81 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.2
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -2.970
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 259.97

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.650
Plasma Protein Binding: 97.26
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-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: Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 8.900
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.730
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.380
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.060
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: Toxic
T. Pyriformis: -473152.560
Rat (Acute): 2.620
Rat (Chronic Oral): 2.760
Fathead Minnow: 610.280
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 48448.450
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 5.190
Log(P): 10.48
Log S: -7.6
Log(Vapor Pressure): -1591.75
Melting Point: 172.29
pKa Acid: 4.1
pKa Basic: 7.94

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9838
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.9012
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8898
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8782
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8759
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8687
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8470
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8449
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8361
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8351
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8280
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8226
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.8094
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8025
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.7975
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7889
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7878
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	2	0.7875
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7867
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7853
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7819
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7780
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7759
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7757
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7750
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7663
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7658
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7637
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7603
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7584
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7584
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7569
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7561
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7561
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7555
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7552
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7535
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7533
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7531
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7497
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7489
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7477
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7457
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7456
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7439
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7417
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7385
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7364
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7357
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7342
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7342
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7341
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7338
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7335
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7327
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7323
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7322
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7319
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7312
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7307
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7294
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7284
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7278
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7271
Capsid scaffolding protein	P88911	P88911_HHV8	Human herpesvirus 8 type M	4	0.7267
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7245
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7227
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7224
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7199
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7197
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7179
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7165
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7146
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7135
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7126
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7109
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7096
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7086
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7080
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7076
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7076
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7072
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	4	0.7037
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7025
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7019
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7012
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7010
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	2	0.7007

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