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Zeylenyl-2,6-diacetate

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Phenyl Amine

Canonical Smiles	CC(=O)O[C@H]1C=C[C@H]([C@@H]([C@@]1(O)COC(=O)c1ccccc1)OC(=O)C)OC(=O)c1ccccc1
InChI	InChI=1S/C25H24O9/c1-16(26)32-21-14-13-20(34-24(29)19-11-7-4-8-12-19)22(33-17(2)27)25(21,30)15-31-23(28)18-9-5-3-6-10-18/h3-14,20-22,30H,15H2,1-2H3/t20-,21+,22+,25-/m1/s1
InChIKey	LSMUFZCEEOVOIM-HXKBJWFLSA-N
Formula	C₂₅H₂₄O₉
HBA	9
HBD	1
MW	468.46
Rotatable Bonds	7
TPSA	125.43
LogP	2.23
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.28
Exact Mass	468.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Uvaria pandensis	Annonaceae	Plantae	673193

Showing of synonyms

Maeda G, Gilissen PJ, et al. (2021). Oxygenated Cyclohexene Derivatives from the Stem and Root Barks of Uvaria pandensis. Journal of natural products,2021, 84(12), 3080-3089. [View] [PubMed]

Pubchem: 102121374

Zinc: ZINC000238742465

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2CC=CC(C2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 468.46 g/mol

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 468.46 g/mol

SMILES: c1ccccc1C(=O)OC2C=CCCC2

Level: 1

Mol. Weight: 468.46 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 468.46 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 468.46 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: -4.53
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.56

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.58
Plasma Protein Binding: 81.5
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: 5.72
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.85
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.53
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.66
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: -163.29
Rat (Acute): 2.52
Rat (Chronic Oral): 3.16
Fathead Minnow: 4.51
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: 420.44
Hydration Free Energy: -2.47
Log(D) at pH=7.4: 2.87
Log(P): 3.41
Log S: -4.3
Log(Vapor Pressure): -9.2
Melting Point: 140.05
pKa Acid: 7.58
pKa Basic: -1.59

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.9797
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.9577
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.9409
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9131
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8909
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8878
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8745
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8699
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8686
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.8589
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8536
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8508
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8496
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8292
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8272
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8017
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7906
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7850
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7767
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7717
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7691
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7678
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7652
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7645
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7624
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7592
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7568
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7523
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7486
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7472
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7468
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7441
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7417
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7414
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7398
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7390
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7380
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	2	0.7380
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7378
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7358
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7348
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.7298
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7273
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7253
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7253
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7237
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7236
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7230
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7215
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7204
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7197
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7146
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7130
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7075
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7066
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7065
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7060

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