(1S,3S)-1,6-dihydroxy-3,5-dimethyl-8-methoxyiso-chroman - Compound Card

(1S,3S)-1,6-dihydroxy-3,5-dimethyl-8-methoxyiso-chroman

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(1S,3S)-1,6-dihydroxy-3,5-dimethyl-8-methoxyiso-chroman

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Benzopyran
    • Subclass: Chromane
Canonical Smiles COc1cc(O)c(c2c1[C@@H](O)O[C@H](C2)C)C
InChI InChI=1S/C12H16O4/c1-6-4-8-7(2)9(13)5-10(15-3)11(8)12(14)16-6/h5-6,12-14H,4H2,1-3H3/t6-,12-/m0/s1
InChIKey CWGRMEHTZDTNRX-QTTZVWFDSA-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: 21580228

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)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.220
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.430
Plasma Protein Binding
43.17
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
9.440
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.950
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.320
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.630
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
-0.120
Rat (Acute)
2.270
Rat (Chronic Oral)
2.190
Fathead Minnow
3.920
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
313.100
Hydration Free Energy
-9.150
Log(D) at pH=7.4
1.280
Log(P)
1.73
Log S
-1.72
Log(Vapor Pressure)
-4.62
Melting Point
129.46
pKa Acid
9.58
pKa Basic
3.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8820
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8709
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8707
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8697
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8641
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8634
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8517
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8500
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8414
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8398
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8230
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8192
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8153
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8104
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8038
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7968
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7924
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7906
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7831
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7782
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7637
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7634
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7618
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7608
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 3 0.7607
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7543
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7543
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7507
N-glycosylase/DNA lyase O15527 OGG1_HUMAN Homo sapiens 4 0.7497
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7479
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7476
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7468
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7431
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7395
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7383
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7345
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7314
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7306
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 3 0.7288
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7254
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7204
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7194
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7152
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7102
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7082
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7074
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7042
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 3 0.7009
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7003
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7000

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