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Cleistodienol A

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=C/OC(=O)c1ccccc1)OC(=O)C)O
InChI	InChI=1S/C18H18O7/c1-11(19)24-16-9-8-15(21)17(25-12(2)20)14(16)10-23-18(22)13-6-4-3-5-7-13/h3-10,15-17,21H,1-2H3/b14-10+/t15-,16+,17-/m0/s1
InChIKey	RMVXQVNGKWJVSB-MHHBOCFLSA-N
Formula	C₁₈H₁₈O₇
HBA	7
HBD	1
MW	346.34
Rotatable Bonds	4
TPSA	99.13
LogP	1.52
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.28
Exact Mass	346.11
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: 137647258

Chembl: CHEMBL4083758

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC=C2CC=CCC2

Level: 1

Mol. Weight: 346.34 g/mol

SMILES: C=C1CC=CCC1

Level: 0

Mol. Weight: 346.34 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 346.34 g/mol

Anti-plasmodial

Cytotoxic

Absorption

Caco-2 (logPapp): -4.8
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.46
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.97

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.32
Plasma Protein Binding: 53.89
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: 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: 4.9
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.64
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.32
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.05
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: -0.82
Rat (Acute): 2.49
Rat (Chronic Oral): 2.66
Fathead Minnow: 4.6
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: 360.69
Hydration Free Energy: -8.34
Log(D) at pH=7.4: 1.84
Log(P): 1.42
Log S: -3.29
Log(Vapor Pressure): -7.31
Melting Point: 120.46
pKa Acid: 6.32
pKa Basic: 0.72

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8996
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8996
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8657
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8657
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8300
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8300
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8125
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8125
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7959
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7959
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7830
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7830
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7816
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7816
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7614
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7614
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7606
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7606
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7562
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7562
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7529
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7529
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7441
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7441
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7407
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7407
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7305
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7305
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7232
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7232
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7190
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7190
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7177
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7177
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7170
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7170
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7157
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7157
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7108
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7108
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7101
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7101
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7062
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7062
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7054
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7054
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	2	0.7052
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	2	0.7052
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7014
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7014

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