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Cleistenediol D

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-LISAXSMJSA-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]

Pubchem: 56958772

Zinc: ZINC000085881096

Nmrshiftdb2: 70087696

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

No bioactivities available.

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: -2.97

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.44
Plasma Protein Binding: 60.48
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: 5.48
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.27
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: -2.53
Rat (Acute): 2.08
Rat (Chronic Oral): 3.16
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: 369.2
Hydration Free Energy: -10.27
Log(D) at pH=7.4: 0.77
Log(P): 1.42
Log S: -2.53
Log(Vapor Pressure): -8.15
Melting Point: 144.3
pKa Acid: 6.59
pKa Basic: 1.47

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9533
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9533
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9182
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9182
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8789
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8789
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8511
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8511
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8487
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8487
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8437
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8437
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.8147
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.8147
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7878
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7878
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.7667
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.7667
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7658
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7658
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7564
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7564
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7558
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7558
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7446
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7446
Iota toxin component Ia	Q46220	Q46220_CLOPF	Clostridium perfringens	3	0.7388
Iota toxin component Ia	Q46220	Q46220_CLOPF	Clostridium perfringens	3	0.7388
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7332
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7332
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7320
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7320
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7273
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7273
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7248
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7248
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7232
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7232
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7228
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7228
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7211
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7211
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	4	0.7201
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	4	0.7201
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7178
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7178
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7163
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7163
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7154
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7154
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7145
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7145
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7139
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7139
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7137
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7137
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7124
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7124
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7124
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7124
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7107
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7107
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7095
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7095
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7084
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7084
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7071
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7071
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7066
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7066
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7062
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7062
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7053
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7053
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7037
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7037
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7009
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7009

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