(+)-usararotenoid-B - Compound Card

(+)-usararotenoid-B

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(+)-usararotenoid-B

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1c(OC)ccc2c1O[C@@H]1COc3c([C@]1(C2=O)O)cc1c(c3)OCO1
InChI InChI=1S/C19H16O8/c1-22-11-4-3-9-16(17(11)23-2)27-15-7-24-12-6-14-13(25-8-26-14)5-10(12)19(15,21)18(9)20/h3-6,15,21H,7-8H2,1-2H3/t15-,19+/m1/s1
InChIKey YCLLOJPGIQDROB-BEFAXECRSA-N
Formula C19H16O8
HBA 8
HBD 1
MW 372.33
Rotatable Bonds 2
TPSA 92.68
LogP 1.66
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 372.08
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: 101938910
Nmrshiftdb2: 70080788

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cc3c(c2)C4C(CO3)Oc5c(C4=O)cccc5

Level: 0

Mol. Weight: 372.33 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.570
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.220
Plasma Protein Binding
80.77
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
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
9.170
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.920
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.080
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.190
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
-11.250
Rat (Acute)
2.170
Rat (Chronic Oral)
1.760
Fathead Minnow
4.750
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
441.530
Hydration Free Energy
-7.020
Log(D) at pH=7.4
2.050
Log(P)
2.13
Log S
-3.65
Log(Vapor Pressure)
-8.31
Melting Point
209.21
pKa Acid
8.05
pKa Basic
0.13
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 0.8938
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8938
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8547
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8547
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8421
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8421
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8328
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8328
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8294
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8294
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8207
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8207
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7969
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7969
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7816
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7816
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7676
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7676
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7671
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7671
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7663
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7663
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7607
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7607
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7586
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7586
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7549
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7549
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7547
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7547
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7540
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7540
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7524
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7524
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7520
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7520
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7510
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7510
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7470
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7470
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7462
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7462
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7462
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7462
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7349
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7349
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7316
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7316
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7309
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7309
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7306
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7306
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7216
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7216
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7193
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7193
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7188
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7188
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7187
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7187
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7184
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7184
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7076
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7076
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7022
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7022
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7002
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7002

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