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Dieporeticenin

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Acetogenin

Canonical Smiles	CCCCCCCCCC/C=C/CCC1OC1CCC1OC1CCCCCCCCCCCCC1=CC(OC1=O)C
InChI	InChI=1S/C37H64O4/c1-3-4-5-6-7-8-9-10-14-17-20-23-26-33-35(40-33)28-29-36-34(41-36)27-24-21-18-15-12-11-13-16-19-22-25-32-30-31(2)39-37(32)38/h17,20,30-31,33-36H,3-16,18-19,21-29H2,1-2H3/b20-17+
InChIKey	NHZOCAXASXRFNX-LVZFUZTISA-N
Formula	C₃₇H₆₄O₄
HBA	4
HBD	0
MW	572.92
Rotatable Bonds	28
TPSA	51.36
LogP	10.72
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.86
Exact Mass	572.48
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ophrypetalum odoratum	Annonaceae	Plantae	489344

Showing of synonyms

Sung'hwa F, Mgina CA, et al. (1999). Ophrypetalin and other annonaceous acetogenins from Ophrypetalum odoratum. Natural Product Letters,1999,13(3),195-202. [View] [PubMed]

Pubchem: 101420981

Chebi: 172069

Nmrshiftdb2: 70096332

No compound-protein relationship available.

SMILES: O1CC1CCC(O2)C2CCCCCCCCCCCCC3=CCOC3=O

Level: 2

Mol. Weight: 572.92 g/mol

SMILES: O1CC1CCCCCCCCCCCCC2=CCOC2=O

Level: 1

Mol. Weight: 572.92 g/mol

SMILES: O1CC1CCC2CO2

Level: 1

Mol. Weight: 572.92 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 572.92 g/mol

SMILES: C1CO1

Level: 0

Mol. Weight: 572.92 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.54
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 2.11
Plasma Protein Binding: 30.03
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 6.5
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.2
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.85
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 7.13
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -12291.08
Rat (Acute): 1.93
Rat (Chronic Oral): 1.8
Fathead Minnow: 32.95
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 421.39
Hydration Free Energy: -2.91
Log(D) at pH=7.4: 7.41
Log(P): 11.59
Log S: -6.84
Log(Vapor Pressure): -8.22
Melting Point: 5.14
pKa Acid: 8.37
pKa Basic: 3.61

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.9432
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.9432
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8670
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8670
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7868
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7868
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7609
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7609
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7590
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7590
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7579
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7579
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7563
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7563
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7501
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7501
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	2	0.7496
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	2	0.7496
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7473
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7473
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	2	0.7472
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	2	0.7472
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7453
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7453
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7443
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7443
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7368
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7368
Carnitine O-acetyltransferase	P47934	CACP_MOUSE	Mus musculus	2	0.7351
Carnitine O-acetyltransferase	P47934	CACP_MOUSE	Mus musculus	2	0.7351
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7311
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7311
Alanine aminotransferase	Q9P9M8	Q9P9M8_9EURY	Pyrococcus furiosus	2	0.7280
Alanine aminotransferase	Q9P9M8	Q9P9M8_9EURY	Pyrococcus furiosus	2	0.7280
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7267
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7267
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	2	0.7243
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	2	0.7243
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7203
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7203
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7194
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7194
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7124
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7124
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7106
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7106
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7079
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7079

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