5,7-dimethoxy-8-(3'-methylbut-2'-enyl) coumarin - Compound Card

5,7-dimethoxy-8-(3'-methylbut-2'-enyl) coumarin

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5,7-dimethoxy-8-(3'-methylbut-2'-enyl) coumarin

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles COc1cc(OC)c2c(c1CC=C(C)C)oc(=O)cc2
InChI InChI=1S/C16H18O4/c1-10(2)5-6-11-13(18-3)9-14(19-4)12-7-8-15(17)20-16(11)12/h5,7-9H,6H2,1-4H3
InChIKey CPXPWRXPEOMRNV-UHFFFAOYSA-N
Formula C16H18O4
HBA 4
HBD 0
MW 274.32
Rotatable Bonds 4
TPSA 48.67
LogP 3.32
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 274.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Clausena anisata Rutaceae Plantae 159034

Showing of synonyms

  • Tatsimo SJN, Tamokou JDD, et al. (2015). LC-MS guided isolation of antibacterial and cytotoxic constituents from Clausena anisata. Med Chem Res, 2015, 24, 1468–1479. [View]
Pubchem: 176911
Nmrshiftdb2: 60033135
Bindingdb: 50008742

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 274.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.120
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.050
Plasma Protein Binding
56.6
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
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
4.880
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.800
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.610
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.500
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
3.570
Rat (Acute)
2.150
Rat (Chronic Oral)
1.960
Fathead Minnow
4.970
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
368.740
Hydration Free Energy
-8.650
Log(D) at pH=7.4
2.730
Log(P)
3.49
Log S
-4.83
Log(Vapor Pressure)
-5.34
Melting Point
110.74
pKa Acid
8.85
pKa Basic
5.96
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 0.9720
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9538
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9069
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8878
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8755
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8700
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8634
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8303
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7950
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7949
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7905
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7900
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7875
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7763
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7610
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7570
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7501
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7456
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7431
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7399
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7378
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7328
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7326
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7313
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7309
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7249
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7245
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7225
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7220
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7191
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7173
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7159
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7137
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7133
Alpha/beta hydrolase fold A5VAT9 A5VAT9_SPHWW Sphingomonas wittichii 2 0.7118
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7114
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7113
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7109
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7108
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7067
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7062
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7033
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7022

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