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(1S,4S,5S,6R)-5-[(benzyloxy)- methyl]-5,6-dihydroxycyclohex-2-ene-1,4-diyl diacetate

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Cyclohexene Derivative
- Subclass: Polyoxygenated Cyclohexene Derivative

Canonical Smiles	CC(=O)O[C@H]1C=C[C@@H]([C@H]([C@]1(O)COC(=O)c1ccccc1)O)OC(=O)C
InChI	InChI=1S/C18H20O8/c1-11(19)25-14-8-9-15(26-12(2)20)18(23,16(14)21)10-24-17(22)13-6-4-3-5-7-13/h3-9,14-16,21,23H,10H2,1-2H3/t14-,15-,16+,18-/m0/s1
InChIKey	MMESXCQWMJEGBH-CUSZFKRNSA-N
Formula	C₁₈H₂₀O₈
HBA	8
HBD	2
MW	364.35
Rotatable Bonds	5
TPSA	119.36
LogP	0.37
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.39
Exact Mass	364.12
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.

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 364.35 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 364.35 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 364.35 g/mol

Anti-plasmodial

Cytotoxic

Absorption

Caco-2 (logPapp): -5.23
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.58
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.96

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.44
Plasma Protein Binding: 60.33
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: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.47
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.33
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.64
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.1
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: -2.58
Rat (Acute): 2.08
Rat (Chronic Oral): 3.15
Fathead Minnow: 4.09
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: 368.75
Hydration Free Energy: -10.24
Log(D) at pH=7.4: 0.81
Log(P): 1.42
Log S: -2.52
Log(Vapor Pressure): -8.16
Melting Point: 144.06
pKa Acid: 6.61
pKa Basic: 1.45

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9387
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9387
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9198
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9198
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9173
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9173
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8993
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8993
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8693
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8693
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8097
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8097
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7956
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7956
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7789
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7789
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7762
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7762
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7487
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7487
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7363
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7363
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7279
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7279
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7251
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7251
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7228
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7228
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7223
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7223
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7198
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7198
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7168
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7168
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7163
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7163
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7159
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7159
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7126
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7126
Penicillin V acylase	P12256	PAC_LYSSH	Lysinibacillus sphaericus	3	0.7114
Penicillin V acylase	P12256	PAC_LYSSH	Lysinibacillus sphaericus	3	0.7114
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7105
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7105
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7100
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7100
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7081
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7081
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7075
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7075
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7061
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7061
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7055
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7055
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7051
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7051
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7038
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	2	0.7038
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7031
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7031
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7011
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7011

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