Cleistenechlorohydrin B - Compound Card

Cleistenechlorohydrin B

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Cleistenechlorohydrin B

Structure
Zoomed Structure
  • Family: Annonaceae
  • Kingdom: Plantae
  • Class: Cyclohexene Derivative
    • Subclass: Polyoxygenated Cyclohexene Derivative
Canonical Smiles CC(=O)O[C@@H]1C=C[C@H]([C@@]([C@H]1O)(O)COC(=O)c1ccccc1)Cl
InChI InChI=1S/C16H17ClO6/c1-10(18)23-12-7-8-13(17)16(21,14(12)19)9-22-15(20)11-5-3-2-4-6-11/h2-8,12-14,19,21H,9H2,1H3/t12-,13-,14+,16+/m1/s1
InChIKey YEEMXVYHDPMVQJ-NYTXWWLZSA-N
Formula C16H17ClO6
HBA 6
HBD 2
MW 340.76
Rotatable Bonds 4
TPSA 93.06
LogP 1.04
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 340.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cleistochlamys kirkii Annonaceae Plantae 1237197

Showing of synonyms

  • Nyandoro SS, Munissi JJ, et al. (2017). Polyoxygenated cyclohexenes and other constituents of Cleistochlamys kirkii leaves. Journal of Natural Products,2017,80(1),114-125. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 216.28 g/mol

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 82.15 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.1
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Non-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)
0.61
Plasma Protein Binding
49.54
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
4.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.0
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.17
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.66
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
0.01
Rat (Acute)
2.65
Rat (Chronic Oral)
2.7
Fathead Minnow
4.05
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
350.4
Hydration Free Energy
-11.69
Log(D) at pH=7.4
1.4
Log(P)
1.97
Log S
-2.68
Log(Vapor Pressure)
-7.69
Melting Point
136.51
pKa Acid
7.57
pKa Basic
1.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9338
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9338
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9272
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9272
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.9079
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.9079
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8931
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8931
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8868
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8868
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8826
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8826
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8729
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8729
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8335
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8335
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8276
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8276
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8227
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8227
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.8174
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.8174
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8048
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8048
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.7855
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.7855
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7841
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7841
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7837
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7837
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7791
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7791
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7783
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7783
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7750
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7750
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7712
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7712
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7678
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7678
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7661
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7661
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7640
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7640
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7611
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7611
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 2 0.7606
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 2 0.7606
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7598
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7598
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7594
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7594
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7587
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7587
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7571
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7571
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7564
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7564
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7554
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7554
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7533
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7533
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7450
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7450
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7411
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7411
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7402
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7402
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7401
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7401
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7380
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7380
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7370
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7370
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7352
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7352
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7347
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7347
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7346
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7346
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7328
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7328
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7325
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7325
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7322
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7322
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7317
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7317
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7314
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7314
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7311
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7311
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7301
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7301
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7262
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7262
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7258
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7258
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7250
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7250
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7245
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7245
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7236
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7236
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7224
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7224
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7223
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7223
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7223
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7223
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7223
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7223
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7206
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7206
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7199
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7199
7,8-dihydroneopterin aldolase J7VEZ6 J7VEZ6_BACCE Bacillus cereus BAG3X2-1 3 0.7194
7,8-dihydroneopterin aldolase J7VEZ6 J7VEZ6_BACCE Bacillus cereus BAG3X2-1 3 0.7194
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7193
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7193
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7190
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7190
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7184
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7184
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7141
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7141
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7129
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7129
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7127
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7127
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7119
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7119
Phosphoribosylformylglycinamidine synthase subunit PurL Q9X0X3 PURL_THEMA Thermotoga maritima 3 0.7117
Phosphoribosylformylglycinamidine synthase subunit PurL Q9X0X3 PURL_THEMA Thermotoga maritima 3 0.7117
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7101
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7101
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7098
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7098
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7093
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7093
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7077
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7077
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7073
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7073
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7070
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7070
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7060
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7060
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7049
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7049
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7039
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7039
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7018
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7018
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7015
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7015

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