(+)-12-dihydrousararotenoid-A - Compound Card

(+)-12-dihydrousararotenoid-A

Select a section from the left sidebar

(+)-12-dihydrousararotenoid-A

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles O[C@@H]1c2ccc3c(c2O[C@H]2[C@@]1(O)c1cc4OCOc4cc1OC2)OCO3
InChI InChI=1S/C18H14O8/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/h1-4,14,17,19-20H,5-7H2/t14-,17-,18+/m1/s1
InChIKey DAVDZIGDWFWYRS-OLMNPRSZSA-N
Formula C18H14O8
HBA 8
HBD 2
MW 358.3
Rotatable Bonds 0
TPSA 95.84
LogP 1.22
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 358.07
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, 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: 73897316
Nmrshiftdb2: 70080782

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 358.3 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.42
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.22
Plasma Protein Binding
76.33
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
13.76
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.0
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.01
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
-11.62
Rat (Acute)
2.15
Rat (Chronic Oral)
1.18
Fathead Minnow
4.36
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
459.93
Hydration Free Energy
-6.63
Log(D) at pH=7.4
1.93
Log(P)
1.74
Log S
-3.49
Log(Vapor Pressure)
-11.3
Melting Point
228.71
pKa Acid
10.35
pKa Basic
-0.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8948
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8948
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8501
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8501
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8296
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8296
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8107
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8107
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7982
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7982
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7957
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7957
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7955
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7955
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7870
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7870
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7814
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7814
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7678
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7678
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7616
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7616
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7530
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7530
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7530
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7530
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7379
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7379
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7374
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7374
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7346
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7346
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7304
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7304
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7295
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7295
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7190
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7190
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7173
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7173
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7151
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7151
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7114
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7114
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7104
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7104
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7064
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7064
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7044
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7044
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7001
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7001

Download SDF