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Zeylenol

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Cycloalkene
- Subclass: Seco-Cyclohexene Derivative

Canonical Smiles	O=C(c1ccccc1)OC[C@@]1(O)[C@@H](O)C=C[C@H]([C@@H]1O)OC(=O)c1ccccc1
InChI	InChI=1S/C21H20O7/c22-17-12-11-16(28-20(25)15-9-5-2-6-10-15)18(23)21(17,26)13-27-19(24)14-7-3-1-4-8-14/h1-12,16-18,22-23,26H,13H2/t16-,17+,18+,21-/m1/s1
InChIKey	AWCUZBLYCWUTRL-OEMYIYORSA-N
Formula	C₂₁H₂₀O₇
HBA	7
HBD	3
MW	384.38
Rotatable Bonds	5
TPSA	113.29
LogP	1.09
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	384.12
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: 10992619

Cas: 78804-17-8

Zinc: ZINC000091297329

Nmrshiftdb2: 70130515

Chembl: CHEMBL4469789

Comptox: DTXSID70451085

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 384.38 g/mol

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 384.38 g/mol

SMILES: c1ccccc1C(=O)OC2C=CCCC2

Level: 1

Mol. Weight: 384.38 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 384.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 384.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.32
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.5
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.32

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.93
Plasma Protein Binding: 86.16
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: 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: 4.39
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.01
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.98
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.92
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: -11.66
Rat (Acute): 2.2
Rat (Chronic Oral): 3.18
Fathead Minnow: 4.15
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: 413.38
Hydration Free Energy: -8.73
Log(D) at pH=7.4: 2.33
Log(P): 2.13
Log S: -3.12
Log(Vapor Pressure): -9.47
Melting Point: 164.66
pKa Acid: 6.43
pKa Basic: 0.66

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9565
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9540
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9525
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9312
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8887
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8705
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8684
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8481
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8348
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.8166
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8121
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8102
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	4	0.8048
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7960
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7944
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7914
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7914
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7882
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7855
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7851
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7781
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7712
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	2	0.7667
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7652
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7605
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7566
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7557
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7549
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.7537
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7504
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7496
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7459
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7407
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7394
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7357
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7350
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7346
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7343
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7341
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7317
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7317
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7301
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7242
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7228
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7227
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7227
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7189
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7175
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7173
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7168
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7168
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7161
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7155
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7146
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7141
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7118
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7111
Inosine-5'-monophosphate dehydrogenase	P50097	IMDH_TRIFO	Tritrichomonas foetus	2	0.7109
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7106
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7093
Chitinase B	P11797	CHIB_SERMA	Serratia marcescens	4	0.7090
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7075
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7063
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.7052
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7048
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7035
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7028
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7027
Phenylpyruvate C(3)-methyltransferase	Q643C8	MPPJ_STRHY	Streptomyces hygroscopicus	2	0.7027
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7022
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7019

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