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Cleistenediol C

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

Canonical Smiles	CO[C@H]1C=C[C@@H]([C@@H]([C@@]1(O)COC(=O)c1ccccc1)OC(=O)C)OC(=O)C
InChI	InChI=1S/C19H22O8/c1-12(20)26-15-9-10-16(24-3)19(23,17(15)27-13(2)21)11-25-18(22)14-7-5-4-6-8-14/h4-10,15-17,23H,11H2,1-3H3/t15-,16-,17-,19+/m0/s1
InChIKey	WAOAOGHRRPNUAT-LSTDLKDCSA-N
Formula	C₁₉H₂₂O₈
HBA	8
HBD	1
MW	378.38
Rotatable Bonds	6
TPSA	108.36
LogP	1.02
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	378.13
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: 378.38 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 378.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 378.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.91
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.520
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.19

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.280
Plasma Protein Binding: 55.87
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: 5.390
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.460
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.530
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.290
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: -4.450
Rat (Acute): 2.530
Rat (Chronic Oral): 2.630
Fathead Minnow: 4.060
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: 350.190
Hydration Free Energy: -7.680
Log(D) at pH=7.4: 1.370
Log(P): 1.85
Log S: -2.84
Log(Vapor Pressure): -7.53
Melting Point: 114.18
pKa Acid: 7.57
pKa Basic: -0.35

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9664
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9664
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9294
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9294
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9196
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9196
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.9028
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.9028
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9021
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9021
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8377
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8377
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8193
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8193
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8090
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8090
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8078
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8078
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7992
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7992
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7915
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7915
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7816
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7816
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7804
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7804
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7605
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7605
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	4	0.7592
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	4	0.7592
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7581
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7581
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7562
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7562
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7523
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7523
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7443
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7443
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7426
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7426
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7383
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7383
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7308
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7308
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7297
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7297
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7231
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7231
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7212
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7212
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7204
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7204
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7204
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7204
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
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7170
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7170
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7169
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7169
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7164
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7164
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7157
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7157
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7127
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7127
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7075
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7075
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7070
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7070
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7063
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7063
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7062
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7062
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7059
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7059
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7050
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7050
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7049
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7049
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7045
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7045
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	2	0.7030
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	2	0.7030
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7022
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7022
Neprilysin	P08049	NEP_RABIT	Oryctolagus cuniculus	4	0.7020
Neprilysin	P08049	NEP_RABIT	Oryctolagus cuniculus	4	0.7020
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7012
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7012
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7007
Unconventional myosin-Va	Q02440	MYO5A_CHICK	Gallus gallus	2	0.7007

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