(6aR,12aS)-2,3-methylenedioxy-9-methoxy-8-(3,3-dimethylallyl)-12a-hydroxyrotenoid - Compound Card

(6aR,12aS)-2,3-methylenedioxy-9-methoxy-8-(3,3-dimethylallyl)-12a-hydroxyrotenoid

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(6aR,12aS)-2,3-methylenedioxy-9-methoxy-8-(3,3-dimethylallyl)-12a-hydroxyrotenoid

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles COc1ccc2c(c1CC=C(C)C)O[C@H]1[C@@](C2=O)(O)c2cc3OCOc3cc2OC1
InChI InChI=1S/C23H22O7/c1-12(2)4-5-13-16(26-3)7-6-14-21(13)30-20-10-27-17-9-19-18(28-11-29-19)8-15(17)23(20,25)22(14)24/h4,6-9,20,25H,5,10-11H2,1-3H3/t20-,23+/m1/s1
InChIKey ZFSLOJRJABHMTL-OFNKIYASSA-N
Formula C23H22O7
HBA 7
HBD 1
MW 410.42
Rotatable Bonds 3
TPSA 83.45
LogP 3.16
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 410.14
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

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]
Pubchem: 641748
Nmrshiftdb2: 20000685

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 410.42 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.610
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.360
Plasma Protein Binding
94.85
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
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
10.160
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.090
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.730
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.400
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
-51.900
Rat (Acute)
2.160
Rat (Chronic Oral)
1.730
Fathead Minnow
5.190
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
474.670
Hydration Free Energy
-4.200
Log(D) at pH=7.4
3.110
Log(P)
4.36
Log S
-4.85
Log(Vapor Pressure)
-9.5
Melting Point
176.3
pKa Acid
8.4
pKa Basic
2.88
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 0.9066
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9066
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8440
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8440
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8358
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8358
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8324
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8324
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8217
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8217
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8065
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8065
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8031
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8031
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7901
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7901
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7841
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7841
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7693
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7693
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7682
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7682
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7659
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7659
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7622
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7622
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7459
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7459
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7372
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7372
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7302
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7302
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7264
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7264
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7244
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7244
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7228
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7228
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7113
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7113
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7049
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7049

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