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Atovaquone
- Family: Plantae - Bignoniaceae
- Kingdom: Plantae
- Class: Quinone
| Canonical Smiles | Clc1ccc(cc1)C1CCC(CC1)C1=C(O)c2c(C(=O)C1=O)cccc2 |
|---|---|
| InChI | InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,24H,5-8H2 |
| InChIKey | BSJMWHQBCZFXBR-UHFFFAOYSA-N |
| Formula | C22H19ClO3 |
| HBA | 3 |
| HBD | 1 |
| MW | 366.84 |
| Rotatable Bonds | 2 |
| TPSA | 54.37 |
| LogP | 5.35 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.27 |
| Exact Mass | 366.1 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Newbouldia leavis | Bignoniaceae | Plantae | 211924 |
Showing of synonyms
Atovaquone
95233-18-4
Acuvel
Mepron (antipneumocystic)
BW 566C
2-(TRANS-4-(4-CHLOROPHENYL)CYCLOHEXYL)-3-HYDROXY-1,4-NAPHTHALENEDIONE
Atovacuona
2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone
2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
NSC-759582
Y883P1Z2LT
DTXSID7022629
BW-566C
CHEBI:575568
1,4-Naphthalenedione, 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-, trans-
DTXCID602629
2-[trans-4-(p-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
DRG-0084
BW 566C-80
HSDB 7083
BW-566C-80
Atovaquonum
UNII-Y883P1Z2LT
Atovaquone [USAN:USP:INN:BAN]
2-(4-(4'-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone
Atovaquone Oral Suspension
ATOVAQUONE [MART.]
ATOVAQUONE [USP-RS]
BW-A566C
ATOVAQUONE [EP MONOGRAPH]
P01AX06
ATOVAQUONE [USP MONOGRAPH]
MALARONE COMPONENT ATOVAQUONE
3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxy-naphthalene-1,2-dione
Trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
1,4-Naphthalenedione, 2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-
ATOVAQUONE COMPONENT OF MALARONE
NSC 759582
MALARONE PEDIATRIC COMPONENT ATOVAQUONE
ATOVAQUONE COMPONENT OF MALARONE PEDIATRIC
Mepron
Wellvone
Cis-Atovaquone
137732-39-9
Atavaquone
94015-53-9
566C80
566C
3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
Atovaquone (Atavaquone)
F1W7QUV0KI
CIS-ATOVAQUONE (RACEMIC)
2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone
2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione
2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione
Trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
NCGC00016961-01
Atovaquone 100 microg/mL in Acetonitrile
CAS-95233-18-4
2-(cis-4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthalenedione
2-(cis-4-(4-Chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione
Cis-2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone
1,4-Naphthalenedione, 2-(cis-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-
2-((1r,4r)-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione
2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione
Mepron (TN)
BW-A 566C
SR-05000001438
CRL-8131 & Atovaquone
Atovaquona
2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
Atovaquone & Interleukin 12
2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-naphthalene-1,4-dione
Cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
Trans-2-(4-(4-chlorophenyl) cyclohexyl)-3-hydroxynaphthalene-1,4-dione
ATO & IL-12
2-[trans-4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
Cis-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
USP Atovaquone Related Compound A
Atorvastatin EP Impurity B
BW 566C80
MFCD00889188
Atovaquone (Standard)
Spectrum_001743
Starbld0018905
ATOVAQUONE [MI]
SpecPlus_000686
ATOVAQUONE [INN]
ATOVAQUONE [JAN]
Prestwick0_000534
Prestwick1_000534
Prestwick2_000534
Prestwick3_000534
Spectrum2_001665
Spectrum3_000991
Spectrum4_001117
Spectrum5_001382
UNII-F1W7QUV0KI
Atovaquone (Atavaquone)?
ATOVAQUONE [HSDB]
ATOVAQUONE [USAN]
ATOVAQUONE [VANDF]
ATOVAQUONE [WHO-DD]
SCHEMBL21694
SCHEMBL21695
Atovaquone (JAN/USP/INN)
BSPBio_000547
BSPBio_002681
KBioGR_001594
KBioSS_002223
MLS002153863
BIDD:GT0849
DivK1c_006782
SCHEMBL637069
SPECTRUM1504210
SPBio_001849
SPBio_002468
Atovaquone - Bio-X trade mark
BPBio1_000603
CHEMBL222334
CHEMBL471792
CHEMBL519462
GTPL9695
SCHEMBL1542719
SCHEMBL1649508
SCHEMBL9975142
ATOVAQUONE [ORANGE BOOK]
Atovaquone, >=98% (HPLC)
Atovaquone for system suitability
CHEBI:95346
KBio1_001726
KBio2_002223
KBio2_004791
KBio2_007359
KBio3_001901
DTXSID20916694
KUCQYCKVKVOKAY-CTYIDZIISA-N
KUCQYCKVKVOKAY-OTVXOJSOSA-N
BDBM192009
GLXC-02590
HMS1569L09
HMS1922F19
HMS2089M14
HMS2093C10
HMS2096L09
HMS2235N08
HMS3369N09
HMS3651N20
HMS3713L09
Pharmakon1600-01504210
BCP09477
MFA73239
VHD01514
Tox21_110714
CCG-39090
FD7252
HY-13832R
NSC759582
S3079
STK636160
2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-dihydronaphthalene-1,4-dione
AKOS005567953
AKOS015895691
AKOS015961933
Tox21_110714_1
BW-556C-80
CCG-220534
DB01117
FA18025
NCGC00016961-02
NCGC00016961-03
NCGC00016961-04
NCGC00016961-06
NCGC00016961-07
NCGC00016961-11
NCGC00095113-01
NCGC00095113-02
AC-30251
AS-12809
BA164228
HY-13832
SMR001233220
SBI-0052893.P002
A2545
AB00513855
NS00010018
NS00077594
SW219222-1
C06835
D00236
EN300-120639
EN300-731648
F18448
SBI-0052893.0001
AB00053222-03
AB00053222_04
AB00053222_05
Q418179
SR-05000001438-1
SR-05000001438-2
SR-05000001438-4
SR-05000001438-5
Z2588038997
2-[4-(4-chlorophenyl)cyclohexy]-3-hydroxy-1,4-naphthoquinone
2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-napthoquinone
2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1.4-naphthoquinone
3-[4-(p-chlorophenyl)cyclohexyl]-4-hydroxy-1,2-naphthoquinone
1,2-Naphthalenedione, 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxy-
1,4-Naphthalenedione, 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-
2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxynaphthoquinone, trans-
Cis -2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione
2-hydroxy-3-[(1r,4r)-4-(4-chlorophenyl)cyclohexyl]-1,4-dihydronaphthalene-1,4-dione
Atovaquone Related Compound A (USP)
Atovaquone Imp. B (EP)
296C85
GR 261266X
Pubchem:
74989
Cas:
95233-18-4
Gnps:
CCMSLIB00000078570
Zinc:
ZINC000100345537
Chebi:
95346
Chembl:
CHEMBL222334
Bindingdb:
192009
CPRiL:
65086
SMILES: c1cccc(c12)C=C(C(=O)C2=O)C3CCC(CC3)c4ccccc4
Level: 2
Mol. Weight: 366.84 g/mol
SMILES: c1cccc(c12)C=C(C(=O)C2=O)C3CCCCC3
Level: 1
Mol. Weight: 366.84 g/mol
SMILES: c1ccccc1C2CCCCC2
Level: 1
Mol. Weight: 366.84 g/mol
SMILES: c1cccc(c12)C=CC(=O)C2=O
Level: 0
Mol. Weight: 366.84 g/mol
SMILES: C1CCCCC1
Level: 0
Mol. Weight: 366.84 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 366.84 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.73
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.66
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.14
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.98
- Plasma Protein Binding
- 80.81
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.48
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.19
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.47
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.99
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- 0.16
- Rat (Acute)
- 2.81
- Rat (Chronic Oral)
- 2.58
- Fathead Minnow
- 4.86
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 454.33
- Hydration Free Energy
- -5.65
- Log(D) at pH=7.4
- 3.83
- Log(P)
- 5.48
- Log S
- -5.91
- Log(Vapor Pressure)
- -8.83
- Melting Point
- 176.03
- pKa Acid
- 6.56
- pKa Basic
- 3.65
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Dihydroorotate dehydrogenase (quinone), mitochondrial | Q63707 | PYRD_RAT | Rattus norvegicus | 3 | 0.8808 |
| Acidic phospholipase A2 3 | P60045 | PA2A3_NAJSG | Naja sagittifera | 3 | 0.8777 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.8646 |
| Beta-elicitin cinnamomin | P15569 | ELIB_PHYCI | Phytophthora cinnamomi | 3 | 0.8324 |
| Snake venom metalloproteinase atrolysin-D | P15167 | VM1AD_CROAT | Crotalus atrox | 3 | 0.8246 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8033 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7971 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 3 | 0.7959 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P00189 | CP11A_BOVIN | Bos taurus | 4 | 0.7890 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7830 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7824 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7813 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7761 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7747 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7736 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7664 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7586 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7480 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7466 |
| Stimulator of interferon genes protein | Q86WV6 | STING_HUMAN | Homo sapiens | 3 | 0.7443 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7439 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.7415 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7398 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7388 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7373 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7362 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7314 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7273 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7257 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7215 |
| Anthranilate phosphoribosyltransferase | P50384 | TRPD_SACS2 | Saccharolobus solfataricus | 2 | 0.7209 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7198 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 2 | 0.7192 |
| Anhydro-N-acetylmuramic acid kinase | Q9I5Q5 | ANMK_PSEAE | Pseudomonas aeruginosa | 2 | 0.7157 |
| Dipeptidyl peptidase 4 | P14740 | DPP4_RAT | Rattus norvegicus | 2 | 0.7116 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7096 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7089 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7049 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7013 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7002 |