(4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone - Compound Card

(4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone

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(4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone

Structure
Zoomed Structure
  • Family: Fungi - Incertae sedis
  • Kingdom: Fungi
  • Class: Ketone
Canonical Smiles O[C@H]1C=C(C)C(=O)C[C@@H]1O
InChI InChI=1S/C7H10O3/c1-4-2-6(9)7(10)3-5(4)8/h2,6-7,9-10H,3H2,1H3/t6-,7-/m0/s1
InChIKey LOFGUEYYNOZLJL-BQBZGAKWSA-N
Formula C7H10O3
HBA 3
HBD 2
MW 142.15
Rotatable Bonds 0
TPSA 57.53
LogP -0.37
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 10
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 142.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Geosmithia langdonii Incertae sedis Fungi 240214

Showing of synonyms

  • Malak LG, Ibrahim MA, et al. (2014). Antileishmanial metabolites from geosmithia langdonii. Journal of Natural Products,2014,77(9),1987-1991. [View] [PubMed]
Pubchem: 70677551
Nmrshiftdb2: 60033065

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 142.15 g/mol

Anti-leishmanial

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.4
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.2
Plasma Protein Binding
15.86
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
4.54
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.62
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.58
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
2.92
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
-0.23
Rat (Acute)
1.14
Rat (Chronic Oral)
2.13
Fathead Minnow
2.85
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
279.65
Hydration Free Energy
-13.22
Log(D) at pH=7.4
-0.45
Log(P)
-0.66
Log S
0.06
Log(Vapor Pressure)
-4.63
Melting Point
118.63
pKa Acid
8.63
pKa Basic
4.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.9009
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.9009
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8161
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8161
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8079
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8079
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7688
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7688
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7486
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7486
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7473
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7473
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7300
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7300
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7179
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7179
Gibberellin receptor GID1 Q6L545 GID1_ORYSJ Oryza sativa subsp. japonica 3 0.7151
Gibberellin receptor GID1 Q6L545 GID1_ORYSJ Oryza sativa subsp. japonica 3 0.7151

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