6-hydroxy-3-methoxytremetone - Compound Card

6-hydroxy-3-methoxytremetone

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6-hydroxy-3-methoxytremetone

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Benzofuran
Canonical Smiles CO[C@H]1[C@@H](Oc2c1cc(C(=O)C)c(c2)O)C(=C)C
InChI InChI=1S/C14H16O4/c1-7(2)13-14(17-4)10-5-9(8(3)15)11(16)6-12(10)18-13/h5-6,13-14,16H,1H2,2-4H3/t13-,14+/m0/s1
InChIKey PHYSEYYYFQMJGP-UONOGXRCSA-N
Formula C14H16O4
HBA 4
HBD 1
MW 248.28
Rotatable Bonds 3
TPSA 55.76
LogP 2.62
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 248.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Liatris spicata Asteraceae Plantae 886939

Showing of synonyms

  • Ezzat M.I, Ezzat S.M, et al. (2017). In vitro evaluation of cytotoxic activity of the ethanol extract and isolated compounds from the corms of Liatris spicata (L.) willd on HepG2. Natural product research,2017, 31(11), 1325-1328. [View] [PubMed]
Pubchem: 15281118
Nmrshiftdb2: 80000413

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 248.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.440
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.560
Plasma Protein Binding
51.48
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
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
10.320
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.620
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.420
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.690
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
2.190
Rat (Acute)
2.330
Rat (Chronic Oral)
2.320
Fathead Minnow
4.130
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
331.040
Hydration Free Energy
-7.880
Log(D) at pH=7.4
2.600
Log(P)
2.92
Log S
-3.49
Log(Vapor Pressure)
-5.46
Melting Point
115.28
pKa Acid
8.26
pKa Basic
4.68
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 0.9700
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9569
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9437
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9289
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8775
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.8635
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.8483
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.8369
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.8163
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8111
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8002
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7921
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7904
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7898
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7841
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7747
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7700
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7682
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7669
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7639
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7573
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7568
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7530
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7489
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7427
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7379
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7341
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7333
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7308
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7293
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7293
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7284
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7256
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7243
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7235
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7170
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7169
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7159
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7127
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7110
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7101
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7097
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7083
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7076
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7062
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7049
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7031

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