5,7-dimethoxy-8-(3'-hydroxy-3'methyl-1'-butene)-coumarin - Compound Card

5,7-dimethoxy-8-(3'-hydroxy-3'methyl-1'-butene)-coumarin

Select a section from the left sidebar

5,7-dimethoxy-8-(3'-hydroxy-3'methyl-1'-butene)-coumarin

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles COc1cc(OC)c2c(c1/C=C/C(O)(C)C)oc(=O)cc2
InChI InChI=1S/C16H18O5/c1-16(2,18)8-7-11-13(20-4)9-12(19-3)10-5-6-14(17)21-15(10)11/h5-9,18H,1-4H3/b8-7+
InChIKey ADODTNKKUQGPNW-BQYQJAHWSA-N
Formula C16H18O5
HBA 5
HBD 1
MW 290.31
Rotatable Bonds 4
TPSA 68.9
LogP 2.59
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 290.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Toddalia asiatica Rutaceae Plantae 2839963

Showing of synonyms

  • Oketch-Rabah HA, Mwangi JW, et al. (2000). A new antiplasmodial coumarin from Toddalia asiatica roots. Fitoterapia,2000,71(6),636-640. [View] [PubMed]
Pubchem: 10493702

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 290.31 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.46
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.270
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.000
Plasma Protein Binding
55.45
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
2.720
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.740
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.830
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.990
Micronucleos
Safe
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)
2.560
Rat (Chronic Oral)
1.950
Fathead Minnow
4.740
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
384.540
Hydration Free Energy
-10.710
Log(D) at pH=7.4
1.820
Log(P)
2.11
Log S
-3.8
Log(Vapor Pressure)
-5.93
Melting Point
167.47
pKa Acid
8.19
pKa Basic
4.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9606
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9606
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8944
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8944
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8810
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8810
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8755
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8755
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8101
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8101
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8071
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8071
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7913
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7913
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7888
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7888
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7819
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7819
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7808
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7808
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7806
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7806
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7798
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7798
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7797
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7797
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7720
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7720
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7645
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7645
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7643
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7643
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7636
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7636
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7552
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7552
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7548
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7548
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7530
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7530
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7496
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7496
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7481
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7481
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7456
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7456
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7405
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7405
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7398
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7398
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7385
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7385
N-acetylhexosamine 1-kinase E8MF12 NAHK_BIFL2 Bifidobacterium longum subsp. longum 3 0.7359
N-acetylhexosamine 1-kinase E8MF12 NAHK_BIFL2 Bifidobacterium longum subsp. longum 3 0.7359
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7338
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7338
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7337
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7337
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7306
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7306
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7271
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7271
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7255
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7255
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7243
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7243
uroporphyrinogen-III C-methyltransferase P95417 P95417_PSEAI Pseudomonas aeruginosa 3 0.7235
uroporphyrinogen-III C-methyltransferase P95417 P95417_PSEAI Pseudomonas aeruginosa 3 0.7235
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7206
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7206
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7188
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7188
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7169
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7169
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7141
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7141
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7129
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7129
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7125
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7125
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7119
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7119
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7111
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7111
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7099
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7099
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7068
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7068
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7064
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7064
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7056
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7056
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7053
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7053
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7045
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7045
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7038
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7038

Download SDF