6-methoxymellein - Compound Card

6-methoxymellein

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6-methoxymellein

Structure
Zoomed Structure
  • Family: Plantae - Umbelliferae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Dihydroisocoumarin
Canonical Smiles COc1cc2C[C@@H](C)OC(=O)c2c(c1)O
InChI InChI=1S/C11H12O4/c1-6-3-7-4-8(14-2)5-9(12)10(7)11(13)15-6/h4-6,12H,3H2,1-2H3/t6-/m1/s1
InChIKey AIFNAMVERSBWPS-ZCFIWIBFSA-N
Formula C11H12O4
HBA 4
HBD 1
MW 208.21
Rotatable Bonds 1
TPSA 55.76
LogP 1.5
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 208.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Daucus virgatus Umbelliferae Plantae 1869349

Showing of synonyms

  • Snene A, Sirignano C, et al. (2017). Antiproliferative metabolites from the Northern African endemic plant Daucus virgatus (Apiaceae). Phytochemistry,2017,143,194-198. [View] [PubMed]
Pubchem: 83412
Kegg Ligand: C02381
Chebi: 2212
Nmrshiftdb2: 80003017

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CCOC2=O

Level: 0

Mol. Weight: 208.21 g/mol

Antiproliferative

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.540
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.610
Plasma Protein Binding
31.63
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
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
7.070
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.820
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.850
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.720
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
1.590
Rat (Acute)
2.040
Rat (Chronic Oral)
2.050
Fathead Minnow
3.960
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
329.450
Hydration Free Energy
-9.130
Log(D) at pH=7.4
1.890
Log(P)
2.42
Log S
-2.27
Log(Vapor Pressure)
-4.59
Melting Point
116.77
pKa Acid
8.25
pKa Basic
5.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9352
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9255
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9187
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9113
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.9070
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9020
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9014
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8995
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8987
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8842
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8745
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8694
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8668
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8649
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8398
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8380
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8367
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8348
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8310
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8302
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.8261
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8207
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8203
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8179
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8175
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8142
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8064
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8041
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7995
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7875
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7778
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7666
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7640
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7632
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7570
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7546
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7481
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7421
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7411
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7411
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7398
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7371
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7355
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7342
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7328
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7266
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7259
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7259
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7258
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7220
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7212
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7211
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7208
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7197
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7181
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7173
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7145
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7135
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7120
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7119
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7116
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7115
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7110
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7097
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7096
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7084
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7070
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7062
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7045
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7045
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7042
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7041
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7038
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7035
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7023
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7013
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7010
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7009
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7001

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