(3S,4R)-6-hydroxy-8-methoxy-3,5-dimethyl isochromanol - Compound Card

(3S,4R)-6-hydroxy-8-methoxy-3,5-dimethyl isochromanol

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(3S,4R)-6-hydroxy-8-methoxy-3,5-dimethyl isochromanol

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Benzopyran
    • Subclass: Isochroman
Canonical Smiles COc1cc(O)c(c2c1CO[C@H]([C@@H]2O)C)C
InChI InChI=1S/C12H16O4/c1-6-9(13)4-10(15-3)8-5-16-7(2)12(14)11(6)8/h4,7,12-14H,5H2,1-3H3/t7-,12-/m0/s1
InChIKey FWQJAZKWNXACKB-MADCSZMMSA-N
Formula C12H16O4
HBA 4
HBD 2
MW 224.26
Rotatable Bonds 1
TPSA 58.92
LogP 1.66
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 224.1
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: 139585712
Nmrshiftdb2: 80018255

No compound-protein relationship available.

Structure

SMILES: C1COCc(c12)cccc2

Level: 0

Mol. Weight: 224.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.230
Human Oral Bioavailability 50%
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)
0.440
Plasma Protein Binding
41.3
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.840
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.060
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.280
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.650
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
1.510
Rat (Acute)
2.280
Rat (Chronic Oral)
2.240
Fathead Minnow
3.910
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
314.030
Hydration Free Energy
-9.780
Log(D) at pH=7.4
1.100
Log(P)
1.32
Log S
-1.69
Log(Vapor Pressure)
-4.72
Melting Point
127.37
pKa Acid
10.08
pKa Basic
3.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8908
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8837
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8745
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8633
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8604
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8532
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8521
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8448
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8377
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8358
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8305
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8263
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8136
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8069
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8011
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7985
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7891
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7778
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7774
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7670
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7634
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7621
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7590
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7579
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7553
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7471
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7426
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7412
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7410
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7382
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7336
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7294
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7206
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7194
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7185
p-hydroxyphenylacetate 3-hydroxylase, oxygenase component Q6Q272 HPAH_ACIBA Acinetobacter baumannii 4 0.7173
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7170
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7131
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7096
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7082
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7028
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7020
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7002

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