(3S)-6-hydroxy-8-methoxy-3-methylisochroman - Compound Card

(3S)-6-hydroxy-8-methoxy-3-methylisochroman

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(3S)-6-hydroxy-8-methoxy-3-methylisochroman

Structure
Zoomed Structure
  • Family: Trichocomaceae
  • Kingdom: Fungi
  • Class: Benzopyran
    • Subclass: Isochroman
Canonical Smiles COc1cc(O)cc2c1C(O)O[C@H](C2)C
InChI InChI=1S/C11H14O4/c1-6-3-7-4-8(12)5-9(14-2)10(7)11(13)15-6/h4-6,11-13H,3H2,1-2H3/t6-,11?/m0/s1
InChIKey SSQRWQVPZJZCOV-OCAOPBLFSA-N
Formula C11H14O4
HBA 4
HBD 2
MW 210.23
Rotatable Bonds 1
TPSA 58.92
LogP 1.35
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 210.09
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: 122367726
Nmrshiftdb2: 80018253

No compound-protein relationship available.

Structure

SMILES: C1COCc(c12)cccc2

Level: 0

Mol. Weight: 134.18 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.170
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.460
Plasma Protein Binding
25.04
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.420
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.970
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.340
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.430
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
1.040
Rat (Acute)
2.210
Rat (Chronic Oral)
2.260
Fathead Minnow
3.910
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
308.260
Hydration Free Energy
-10.020
Log(D) at pH=7.4
0.970
Log(P)
1.11
Log S
-1.45
Log(Vapor Pressure)
-4.36
Melting Point
132.22
pKa Acid
9.55
pKa Basic
2.71
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 0.9192
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9185
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8920
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8912
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8830
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8802
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8800
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8778
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.8770
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8766
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8747
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8652
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8643
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8617
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8593
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8567
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8484
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8446
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8413
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8372
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8341
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8294
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8287
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8277
N-glycosylase/DNA lyase O15527 OGG1_HUMAN Homo sapiens 4 0.8244
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8178
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.8178
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8152
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.8071
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8017
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8004
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7993
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7987
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7917
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7904
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7901
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7828
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7827
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7752
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7747
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7702
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7697
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7694
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7638
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7592
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 3 0.7576
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7555
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7534
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7527
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7509
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7446
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7443
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7424
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7408
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7403
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7381
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7367
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7348
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7343
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7329
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7319
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7309
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7299
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7292
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7287
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7286
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7283
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7274
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7256
Purine nucleoside phosphorylase 2 P45563 XAPA_ECOLI Escherichia coli 4 0.7248
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7237
Rac-like GTP-binding protein ARAC7 O82480 RAC7_ARATH Arabidopsis thaliana 3 0.7228
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7226
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7204
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7188
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7181
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7177
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7176
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7172
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7159
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8ZMF7 ISPF_SALTY Salmonella typhimurium 3 0.7158
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7154
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7145
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7142
Acetylserotonin O-methyltransferase P46597 ASMT_HUMAN Homo sapiens 4 0.7140
Geranyl diphosphate 2-C-methyltransferase D3KYU3 GPPMT_STRLS Streptomyces lasalocidi 3 0.7114
Putative N-acetyl glucosaminyl transferase Q6U8B0 Q6U8B0_RAOTE Raoultella terrigena 3 0.7111
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7106
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7096
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7076
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7054
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7050
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7046
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7018
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7016

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