(3S)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin - Compound Card

(3S)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin

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(3S)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Coumarin
    • Subclass: Isocoumarin
Canonical Smiles COc1cc(O)cc2c1C(=O)O[C@H](C2)C
InChI InChI=1S/C11H12O4/c1-6-3-7-4-8(12)5-9(14-2)10(7)11(13)15-6/h4-6,12H,3H2,1-2H3/t6-/m0/s1
InChIKey WGUHOBJSLARYHD-LURJTMIESA-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 Penicillium sp Trichocomaceae Fungi 5081

Showing of synonyms

  • 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]
Pubchem: 38350045
Nmrshiftdb2: 80018254

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CCOC2=O

Level: 0

Mol. Weight: 208.21 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.530
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.630
Plasma Protein Binding
31.22
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
7.320
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.850
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.870
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.690
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
1.620
Rat (Acute)
2.000
Rat (Chronic Oral)
2.050
Fathead Minnow
3.970
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
330.780
Hydration Free Energy
-8.820
Log(D) at pH=7.4
1.420
Log(P)
1.73
Log S
-2.06
Log(Vapor Pressure)
-4.62
Melting Point
147.7
pKa Acid
8.51
pKa Basic
5.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9182
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9051
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8917
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8912
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8890
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.8825
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8724
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8705
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8632
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8614
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8597
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8585
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8566
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8549
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8519
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8401
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8384
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8384
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8364
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.8352
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8350
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8342
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8285
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8275
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8102
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.8096
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8066
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8020
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8018
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7996
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7930
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7872
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7832
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7813
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7694
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7692
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7608
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7566
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7565
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7564
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7556
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7534
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7530
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7425
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7422
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7416
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7406
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7380
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7379
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7357
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7331
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7329
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7317
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7305
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7284
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7263
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7248
Rac-like GTP-binding protein ARAC7 O82480 RAC7_ARATH Arabidopsis thaliana 3 0.7209
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7203
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7190
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7183
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7168
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7163
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7150
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7149
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7142
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7138
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7134
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7124
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7104
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7088
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7080
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7068
Putative N-acetyl glucosaminyl transferase Q6U8B0 Q6U8B0_RAOTE Raoultella terrigena 3 0.7059
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7028
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7027
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7006

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