Usararotenoid A - Compound Card

Usararotenoid A

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Usararotenoid A

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles O=C1c2ccc3c(c2O[C@H]2[C@@]1(O)c1cc4OCOc4cc1OC2)OCO3
InChI InChI=1S/C18H12O8/c19-17-8-1-2-10-16(25-7-22-10)15(8)26-14-5-21-11-4-13-12(23-6-24-13)3-9(11)18(14,17)20/h1-4,14,20H,5-7H2/t14-,18+/m1/s1
InChIKey JYEPVYNKUJFCHX-KDOFPFPSSA-N
Formula C18H12O8
HBA 8
HBD 1
MW 356.29
Rotatable Bonds 0
TPSA 92.68
LogP 1.37
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.28
Exact Mass 356.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia usaramensis usaramensis Leguminosae/Fabaceae Plantae 53625
2 Millettia usaramensis usaramensis Leguminosae/Fabaceae Plantae 53625
3 Millettia usaramensis usaramensis Leguminosae/Fabaceae Plantae 53625

Showing of synonyms

  • Yenesew A, Derese S, et al. (2003). Anti-plasmodial activities and X-ray crystal structures of rotenoids from Millettia usaramensis subspecies usaramensis.. Phytochemistry,2003,64(3),773-779. [View] [PubMed]
  • Yenesew A, Kiplagat JT Mushibe EK Derese S, et al. (2005). Rotenoid derivatives from Kenyan Millettia and Derris species as larvicidal agents. Natural products and drug discovery, Proceedings of the 11th NAPRECA Symposium August 9-12, 2005, Hôtel Panorama, Antananarivo, Madagascar. [View] [PubMed]
  • Yenesew A, Midiwo JO, et al. (1998). Rotenoids, isoflavones and chalcones from the stem bark of Millettia usaramensis subspecies usaramensis. Phytochemistry,1998,47(2),295-300. [View] [PubMed]
Pubchem: 73897315
Nmrshiftdb2: 70080785

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc3c2OC4C(C3=O)c5c(OC4)cc6c(c5)OCO6

Level: 0

Mol. Weight: 356.29 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.530
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.320
Plasma Protein Binding
82.43
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
Non-Inhibitor
CYP 2C9 Substrate
Non-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
12.640
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.350
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.010
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.020
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-10.570
Rat (Acute)
2.020
Rat (Chronic Oral)
1.260
Fathead Minnow
4.560
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
456.160
Hydration Free Energy
-6.420
Log(D) at pH=7.4
2.220
Log(P)
2.44
Log S
-4.56
Log(Vapor Pressure)
-10.7
Melting Point
252.06
pKa Acid
8.49
pKa Basic
0.73
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8963
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8963
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8525
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8525
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8419
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8419
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8342
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8342
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8182
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8182
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8164
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8164
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8053
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8053
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7957
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7957
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7753
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7753
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7731
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7731
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7650
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7650
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7639
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7639
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7612
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7612
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7611
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7611
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7579
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7579
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7566
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7566
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7556
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7556
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7547
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7547
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7460
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7460
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7455
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7455
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7441
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7441
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7415
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7415
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7407
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7407
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7407
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7407
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7404
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7404
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7320
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7320
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7311
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7311
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7296
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7296
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7290
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7290
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7260
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7260
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7234
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7234
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7225
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7225
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7190
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7190
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7176
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7176
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7163
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7163
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7132
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7132
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7130
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7130
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7094
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7094
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7061
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7061

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