(3S)-4,6-dihydro-8-methoxy-3,5-dimethyl-6-oxo-3H-2-benzopyran - Compound Card

(3S)-4,6-dihydro-8-methoxy-3,5-dimethyl-6-oxo-3H-2-benzopyran

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(3S)-4,6-dihydro-8-methoxy-3,5-dimethyl-6-oxo-3H-2-benzopyran

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Benzopyran Derivative
Canonical Smiles COC1=CC(=O)C(=C2C1=CO[C@H](C2)C)C
InChI InChI=1S/C12H14O3/c1-7-4-9-8(2)11(13)5-12(14-3)10(9)6-15-7/h5-7H,4H2,1-3H3/t7-/m0/s1
InChIKey OUKVSYNLCDYHEH-ZETCQYMHSA-N
Formula C12H14O3
HBA 3
HBD 0
MW 206.24
Rotatable Bonds 1
TPSA 35.53
LogP 2.11
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 206.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Penicillium citrinum Trichocomaceae Fungi 5077

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]
Pubchem: 11333211
Nmrshiftdb2: 70022193

No compound-protein relationship available.

Structure

SMILES: C1OCCC(C=12)=CC(=O)C=C2

Level: 0

Mol. Weight: 206.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.890
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.320
Plasma Protein Binding
32.26
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.610
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.300
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.440
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.060
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
0.800
Rat (Acute)
2.380
Rat (Chronic Oral)
2.070
Fathead Minnow
4.140
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
301.910
Hydration Free Energy
-6.110
Log(D) at pH=7.4
1.430
Log(P)
1.22
Log S
-2.32
Log(Vapor Pressure)
-2.96
Melting Point
81.41
pKa Acid
9.79
pKa Basic
5.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8157
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8157
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7338
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7338
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7218
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7218
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7190
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7190
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7158
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7158
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7093
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7093
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7065
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7065
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7059
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7059
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7034
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7034
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7020
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7020
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7005
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7005

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