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Cherrevenol I

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

Canonical Smiles	O=C(c1ccccc1)OC[C@]1(O)[C@H](Cl)C=C[C@H]([C@@H]1O)OC(=O)c1ccccc1
InChI	InChI=1S/C21H19ClO6/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/h1-12,16-18,23,26H,13H2/t16-,17-,18+,21+/m1/s1
InChIKey	OZXFMXVSIMKHPG-WIRSXHRWSA-N
Formula	C₂₁H₁₉ClO₆
HBA	6
HBD	2
MW	402.83
Rotatable Bonds	5
TPSA	93.06
LogP	2.34
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	402.09
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: 26300741

Zinc: ZINC000014924133

Chembl: CHEMBL4450246

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 402.83 g/mol

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 402.83 g/mol

SMILES: c1ccccc1C(=O)OC2C=CCCC2

Level: 1

Mol. Weight: 402.83 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 402.83 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 402.83 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.02
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.7
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.6

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.0
Plasma Protein Binding: 73.02
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 2.39
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.08
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.62
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.64
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: -10.69
Rat (Acute): 2.52
Rat (Chronic Oral): 2.61
Fathead Minnow: 4.13
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: 398.84
Hydration Free Energy: -7.06
Log(D) at pH=7.4: 3.54
Log(P): 3.45
Log S: -3.96
Log(Vapor Pressure): -8.79
Melting Point: 142.66
pKa Acid: 8.09
pKa Basic: -1.16

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9257
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9224
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9215
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.9021
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8961
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8903
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8710
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8690
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8634
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8614
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8611
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8503
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8365
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.8348
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.8339
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8292
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8245
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8193
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8156
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.8096
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8080
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8064
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8045
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.8005
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7993
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7974
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7886
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7879
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7858
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7854
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7833
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7827
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7793
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7782
Genome polyprotein	Q99AU2	Q99AU2_9HEPC	Hepatitis C virus subtype 1b	3	0.7744
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7706
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7680
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7651
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7636
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7628
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7626
Pyruvate kinase PKM	P14618	KPYM_HUMAN	Homo sapiens	3	0.7626
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7606
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7595
Dipeptidyl peptidase 4	P14740	DPP4_RAT	Rattus norvegicus	2	0.7569
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7566
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7530
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7525
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7519
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7513
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7483
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7479
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7475
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7472
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7472
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7464
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7454
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7450
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7438
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7431
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7430
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7422
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7407
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7406
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7399
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7392
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7389
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7379
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7345
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7340
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7335
7,8-dihydroneopterin aldolase	J7VEZ6	J7VEZ6_BACCE	Bacillus cereus BAG3X2-1	3	0.7329
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	2	0.7317
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7314
Phenylpyruvate C(3)-methyltransferase	Q643C8	MPPJ_STRHY	Streptomyces hygroscopicus	2	0.7308
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7307
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7306
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7301
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7299
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7295
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7287
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7280
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7271
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7260
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.7258
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7251
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7241
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7236
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7227
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7224
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7216
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7212
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7207
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7193
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7191
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7190
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7182
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7178
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7168
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7166
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7154
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	2	0.7151
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7149
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7146
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7145
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7143
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7132
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7129
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7129
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7096
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7092
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7078
Inosine-5'-monophosphate dehydrogenase	P50097	IMDH_TRIFO	Tritrichomonas foetus	2	0.7073
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7061
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7055
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7054
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7053
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7046
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7046
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7042
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7034
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7033
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7025
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7018
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7015
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7013
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7004
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7001

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