(4R,5S)-4-hydroxy-3,3,5-trimethylcyclohexanone - Compound Card

(4R,5S)-4-hydroxy-3,3,5-trimethylcyclohexanone

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(4R,5S)-4-hydroxy-3,3,5-trimethylcyclohexanone

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Endione
    • Subclass: Cyclic Endione
Canonical Smiles O=C1C[C@H](C)[C@H](C(C1)(C)C)O
InChI InChI=1S/C9H16O2/c1-6-4-7(10)5-9(2,3)8(6)11/h6,8,11H,4-5H2,1-3H3/t6-,8+/m0/s1
InChIKey CZFNEULXUXGILY-POYBYMJQSA-N
Formula C9H16O2
HBA 2
HBD 1
MW 156.22
Rotatable Bonds 0
TPSA 37.3
LogP 1.37
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 11
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 156.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Marchantia polymorpha Marchantiaceae Plantae 3197
2 Nicotiana tabacum Solanaceae Plantae 4097

Showing of synonyms

  • Hegazy M.E, Hirata T, et al. (2008). Ketoisophorone Transformation by Marchantia polymorpha and Nicotiana tabacum Cultured Cells. Zeitschrift fur Naturforschung. C, Journal of biosciences, 2008, 63(5-6), 403-8. [View] [PubMed]
Pubchem: 135390708

No compound-protein relationship available.

Structure

SMILES: O=C1CCCCC1

Level: 0

Mol. Weight: 156.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.89
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.16
Plasma Protein Binding
27.54
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.24
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.92
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.66
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
0.82
Rat (Acute)
1.96
Rat (Chronic Oral)
1.66
Fathead Minnow
2.96
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
232.17
Hydration Free Energy
-7.29
Log(D) at pH=7.4
0.23
Log(P)
0.98
Log S
-0.51
Log(Vapor Pressure)
-1.65
Melting Point
66.4
pKa Acid
9.94
pKa Basic
6.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9453
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9148
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7972
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7940
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7884
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7847
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7815
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7795
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7758
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7731
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7714
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7683
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7679
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7678
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7641
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7619
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7595
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7563
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7544
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7530
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7507
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7504
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7462
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7441
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7429
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7417
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7402
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7402
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7384
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7371
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7369
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7355
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7353
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7293
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7289
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7272
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7232
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7225
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7205
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7200
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7184
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7165
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7154
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7126
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7111
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7103
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7101
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7094
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7087
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7048
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7043
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7041
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7040
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7034

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