(3S)-6-hydroxy- 8-methoxy-3,5-dimethylisochroman - Compound Card

(3S)-6-hydroxy- 8-methoxy-3,5-dimethylisochroman

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(3S)-6-hydroxy- 8-methoxy-3,5-dimethylisochroman

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Monoaromatic
    • Subclass: Benzopyran Derivative
Canonical Smiles COc1cc(O)c(c2c1CO[C@H](C2)C)C
InChI InChI=1S/C12H16O3/c1-7-4-9-8(2)11(13)5-12(14-3)10(9)6-15-7/h5,7,13H,4,6H2,1-3H3/t7-/m0/s1
InChIKey WEOOJHUZRJSUAQ-ZETCQYMHSA-N
Formula C12H16O3
HBA 3
HBD 1
MW 208.26
Rotatable Bonds 1
TPSA 38.69
LogP 2.17
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 208.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Penicillium citrinum Trichocomaceae Fungi 5077
2 Penicillium sp Trichocomaceae Fungi 5081
3 Penicillium simplicissimum Trichocomaceae Fungi 69488

Showing of synonyms

  • El-Neketi M, Ebrahim W, et al. (2013). Alkaloids and polyketides from Penicillium citrinum, an endophyte isolated from the Moroccan plant Ceratonia siliqua. Journal of Natural Products,2013,76(6),1099-1104. [View] [PubMed]
  • Orfali R, Aly A, et al. (2015). Isochroman and isocoumarin derivatives from hypersaline lake sediment-derived fungus Penicillium sp. Phytochemistry Letters, 2015,13,234–238. [View]
  • Ebada S, Ebrahim W. (2020). Quinoisobutyride A, an acyclic antibacterial tetrapeptide incorporating an unprecedented heterocyclic amino acid residue from the hypersaline lakederived fungus Penicillium simplicissimum strain WSH17. Phytochemistry Letters, 2020,36,95–94. [View]
Pubchem: 14582205
Nmrshiftdb2: 70022192

No compound-protein relationship available.

Structure

SMILES: C1COCc(c12)cccc2

Level: 0

Mol. Weight: 208.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.140
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.320
Plasma Protein Binding
39.62
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.660
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.220
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.180
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.000
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
1.790
Rat (Acute)
2.170
Rat (Chronic Oral)
1.920
Fathead Minnow
3.930
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
302.500
Hydration Free Energy
-7.540
Log(D) at pH=7.4
2.020
Log(P)
2.29
Log S
-1.99
Log(Vapor Pressure)
-3.83
Melting Point
95.6
pKa Acid
10.79
pKa Basic
5.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.9217
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.9217
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9137
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9137
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8783
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8783
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8771
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8771
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8769
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8769
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8748
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8748
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.8678
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8678
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8678
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.8678
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8624
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8624
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8621
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8621
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8483
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8483
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8474
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8474
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8411
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8411
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8411
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8411
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8314
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8314
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8229
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8229
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8228
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8228
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8205
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8205
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8168
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8168
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8166
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8166
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8151
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8151
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8138
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8138
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8128
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8128
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7995
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7995
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7944
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7944
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7921
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7921
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7920
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7920
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7902
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7902
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7892
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7892
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7888
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7888
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7794
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7794
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7706
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7706
p-hydroxyphenylacetate 3-hydroxylase, oxygenase component Q6Q272 HPAH_ACIBA Acinetobacter baumannii 4 0.7686
p-hydroxyphenylacetate 3-hydroxylase, oxygenase component Q6Q272 HPAH_ACIBA Acinetobacter baumannii 4 0.7686
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7641
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7641
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7588
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7588
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7546
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7546
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7529
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7529
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7495
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7495
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7472
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7472
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7471
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7471
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7403
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7403
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7375
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7375
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7315
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7315
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7299
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7299
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7295
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7295
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7279
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7279
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7227
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7227
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7203
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7203
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7170
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7170
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7139
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7139
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7108
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7108
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7104
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7104
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7093
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7093
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7077
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7077
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7067
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7067
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7049
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7049
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7009
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7009

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