4-hydro-7-hydroxy-8-prenyloxyfuroquinoline - Compound Card

4-hydro-7-hydroxy-8-prenyloxyfuroquinoline

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4-hydro-7-hydroxy-8-prenyloxyfuroquinoline

Structure
Zoomed Structure
  • Family: Plantae - Umbelliferae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Quinoline Alkaloid
Canonical Smiles N1=c2c(c(ccc2=CC2C1OC=C2)O)OCC=C(C)C
InChI InChI=1S/C16H17NO3/c1-10(2)5-7-19-15-13(18)4-3-11-9-12-6-8-20-16(12)17-14(11)15/h3-6,8-9,12,16,18H,7H2,1-2H3
InChIKey JJIWIGGIUPFSSV-UHFFFAOYSA-N
Formula C16H17NO3
HBA 4
HBD 1
MW 271.32
Rotatable Bonds 3
TPSA 51.05
LogP 1.64
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 271.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ammi majus Umbelliferae Plantae 48026

Showing of synonyms

  • Mohammed M.M, El-Sharkawy E.R. (2017). Cytotoxic new furoquinoline alkaloid isolated from Ammi majus L. growing in Egypt. Natural Product Research, 2017,31(6),645–652. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1=COC(C12)N=c3c(=C2)cccc3

Level: 0

Mol. Weight: 271.32 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.440
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.970
Plasma Protein Binding
17.99
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.710
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.030
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.500
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.010
Micronucleos
Toxic
NR-AhR
Safe
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
Safe
T. Pyriformis
3.220
Rat (Acute)
2.740
Rat (Chronic Oral)
1.870
Fathead Minnow
4.500
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
363.340
Hydration Free Energy
-8.860
Log(D) at pH=7.4
1.980
Log(P)
2.93
Log S
-3.46
Log(Vapor Pressure)
-5.91
Melting Point
144.73
pKa Acid
8.03
pKa Basic
5.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8883
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8708
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8603
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8564
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8499
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8366
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8343
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8328
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8213
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.8172
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8081
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8077
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8043
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7966
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7929
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7927
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7858
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7856
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7853
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7840
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7806
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7694
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7682
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7680
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7674
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7673
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7665
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7662
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7659
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7645
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7638
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7616
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7571
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7560
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7541
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7538
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7501
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7468
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7461
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7457
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7398
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7358
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7274
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7190
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7189
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.7185
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7183
Diaminopropionate ammonia-lyase P66899 DPAL_ECOLI Escherichia coli 3 0.7176
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7109
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7104
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7070
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7037
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7020
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7019
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7007
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7005
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7005

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