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Cherrevenol H

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Cyclohexene
- Subclass: Oxygenated Cyclohexene

Canonical Smiles	CC(=O)O[C@@H]1C=C[C@H]([C@@H]([C@]1(O)COC(=O)c1ccccc1)O)OC(=O)c1ccccc1
InChI	InChI=1S/C23H22O8/c1-15(24)30-19-13-12-18(31-22(27)17-10-6-3-7-11-17)20(25)23(19,28)14-29-21(26)16-8-4-2-5-9-16/h2-13,18-20,25,28H,14H2,1H3/t18-,19-,20+,23+/m1/s1
InChIKey	WBFAMVDHSGIPNA-UGTOYMOASA-N
Formula	C₂₃H₂₂O₈
HBA	8
HBD	2
MW	426.42
Rotatable Bonds	6
TPSA	119.36
LogP	1.66
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.26
Exact Mass	426.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Monanthotaxis trichocarpa	Annonaceae	Plantae	1202425

Showing of synonyms

Maeda G, van der Wal J, et al. (2020). Oxygenated Cyclohexene Derivatives and Other Constituents from the Roots of Monanthotaxis trichocarpa. Journal of natural products,2020, 83(2), 210-215. [View] [PubMed]

Pubchem: 155556922

Chembl: CHEMBL4556140

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 426.42 g/mol

SMILES: c1ccccc1C(=O)OCC2CC=CCC2

Level: 1

Mol. Weight: 426.42 g/mol

SMILES: c1ccccc1C(=O)OC2C=CCCC2

Level: 1

Mol. Weight: 426.42 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 426.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 426.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.43
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.55
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.96

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.83
Plasma Protein Binding: 82.24
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: 4.6
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.0
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.33
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.23
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: -43.32
Rat (Acute): 2.24
Rat (Chronic Oral): 3.4
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: 414.82
Hydration Free Energy: -3.38
Log(D) at pH=7.4: 2.61
Log(P): 2.99
Log S: -3.79
Log(Vapor Pressure): -9.43
Melting Point: 158.35
pKa Acid: 7.07
pKa Basic: -0.42

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9426
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.9248
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9247
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.9242
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9242
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9187
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9165
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9144
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8877
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8798
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8731
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8678
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8358
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8348
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8221
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.8165
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.8135
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8123
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8069
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.8049
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8041
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7993
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7869
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7812
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7763
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7735
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	2	0.7731
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7707
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7704
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7679
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7659
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7650
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7647
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7644
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7642
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7623
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7622
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7616
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7604
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7595
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	4	0.7590
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7583
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7555
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7553
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7543
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7540
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7532
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7521
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7516
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7473
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7462
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7448
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7409
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7407
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7366
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7358
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7358
Beta-secretase 2	Q9Y5Z0	BACE2_HUMAN	Homo sapiens	2	0.7354
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7338
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7332
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7325
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7323
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7292
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7291
Formate--tetrahydrofolate ligase	Q2RM91	FTHS_MOOTA	Moorella thermoacetica	2	0.7276
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7274
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7220
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7211
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7210
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7193
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7182
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	4	0.7178
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7172
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7164
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7145
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	2	0.7123
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7118
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7112
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	2	0.7102
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7094
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.7081
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7077
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7045
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7042
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7036
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7034
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7029
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7024
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7000

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