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Cleistodienol B

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

Canonical Smiles	O[C@H]1C=CC=C([C@@H]1OC(=O)C)C(OC(=O)C)OC(=O)c1ccccc1
InChI	InChI=1S/C18H18O7/c1-11(19)23-16-14(9-6-10-15(16)21)18(24-12(2)20)25-17(22)13-7-4-3-5-8-13/h3-10,15-16,18,21H,1-2H3/t15-,16-,18?/m0/s1
InChIKey	YDVKAJYTMPFNCH-MZQXSQAVSA-N
Formula	C₁₈H₁₈O₇
HBA	7
HBD	1
MW	346.34
Rotatable Bonds	5
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: 137637549

Chembl: CHEMBL4062020

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2=CC=CCC2

Level: 1

Mol. Weight: 346.34 g/mol

SMILES: C1=CCCC=C1

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): -4.79
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: -3.04

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.52
Plasma Protein Binding: 46.39
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: 4.26
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.94
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.68
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.41
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: -0.96
Rat (Acute): 2.34
Rat (Chronic Oral): 2.83
Fathead Minnow: 4.37
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: 364.68
Hydration Free Energy: -8.33
Log(D) at pH=7.4: 1.85
Log(P): 1.65
Log S: -3.35
Log(Vapor Pressure): -6.99
Melting Point: 115.31
pKa Acid: 6.91
pKa Basic: 0.26

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9366
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9366
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8860
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8860
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8208
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8208
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8161
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8161
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8052
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8052
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	4	0.7801
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	4	0.7801
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7787
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7787
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7709
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7709
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7678
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7678
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7638
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7638
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7530
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7530
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7446
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7446
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7439
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7439
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7438
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7438
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7376
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7376
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7342
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7342
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7338
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7338
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7228
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7228
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7227
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7227
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7179
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7179
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7108
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7108
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7097
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7097
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7076
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7076
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7074
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7074
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7067
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7067
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7018
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7018
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7014
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7014

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