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Dieporeticanin-2

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Acetogenin

Canonical Smiles	CCCCCCCCCCC1OC1CCC1OC1CCCCCCCCCCCCCCCCC1=CC(OC1=O)C
InChI	InChI=1S/C37H66O4/c1-3-4-5-6-7-17-20-23-26-33-35(40-33)28-29-36-34(41-36)27-24-21-18-15-13-11-9-8-10-12-14-16-19-22-25-32-30-31(2)39-37(32)38/h30-31,33-36H,3-29H2,1-2H3
InChIKey	LGHYYUNGHFUVQP-UHFFFAOYSA-N
Formula	C₃₇H₆₆O₄
HBA	4
HBD	0
MW	574.93
Rotatable Bonds	29
TPSA	51.36
LogP	10.95
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.92
Exact Mass	574.5
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: 102064359

Nmrshiftdb2: 70003132

No compound-protein relationship available.

SMILES: O1CC1CCC(O2)C2CCCCCCCCCCCCCCCCC3=CCOC3=O

Level: 2

Mol. Weight: 574.93 g/mol

SMILES: O1CC1CCCCCCCCCCCCCCCCC2=CCOC2=O

Level: 1

Mol. Weight: 574.93 g/mol

SMILES: O1CC1CCC2CO2

Level: 1

Mol. Weight: 574.93 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 574.93 g/mol

SMILES: C1CO1

Level: 0

Mol. Weight: 574.93 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.87
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.49
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2.35

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 2.19
Plasma Protein Binding: 28.12
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: 6.84
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.09
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.1
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.91
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: -12290.06
Rat (Acute): 1.84
Rat (Chronic Oral): 1.81
Fathead Minnow: 31.77
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 438.34
Hydration Free Energy: -2.91
Log(D) at pH=7.4: 7.84
Log(P): 12.23
Log S: -7.09
Log(Vapor Pressure): -8.04
Melting Point: 36.67
pKa Acid: 8.15
pKa Basic: 3.28

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	0.9612
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.9612
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.9058
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.9058
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8685
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8685
Regulatory protein SdiA	P07026	SDIA_ECOLI	Escherichia coli	3	0.8038
Regulatory protein SdiA	P07026	SDIA_ECOLI	Escherichia coli	3	0.8038
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7886
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7886
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7718
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7718
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7629
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7629
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7618
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7618
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7603
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7603
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7541
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7541
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	2	0.7501
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	2	0.7501
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7499
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7499
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	2	0.7485
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	2	0.7485
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7471
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7471
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7470
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7470
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7462
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7462
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7447
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7447
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7396
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7396
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	2	0.7365
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	2	0.7365
Carnitine O-acetyltransferase	P47934	CACP_MOUSE	Mus musculus	2	0.7363
Carnitine O-acetyltransferase	P47934	CACP_MOUSE	Mus musculus	2	0.7363
Alanine aminotransferase	Q9P9M8	Q9P9M8_9EURY	Pyrococcus furiosus	2	0.7357
Alanine aminotransferase	Q9P9M8	Q9P9M8_9EURY	Pyrococcus furiosus	2	0.7357
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7315
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7315
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7296
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7296
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7289
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7289
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	2	0.7246
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	2	0.7246
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7216
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7216
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7210
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7210
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7208
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7208
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7195
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7195
Alpha/beta hydrolase fold protein	D2J2T6	D2J2T6_9RHIZ	Ochrobactrum sp. T63	2	0.7182
Alpha/beta hydrolase fold protein	D2J2T6	D2J2T6_9RHIZ	Ochrobactrum sp. T63	2	0.7182
thiamine diphosphokinase	Q82ZE3	Q82ZE3_ENTFA	Enterococcus faecalis	2	0.7169
thiamine diphosphokinase	Q82ZE3	Q82ZE3_ENTFA	Enterococcus faecalis	2	0.7169
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	2	0.7149
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase	P9WNH5	HSAD_MYCTU	Mycobacterium tuberculosis	2	0.7149
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7135
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7135
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	2	0.7130
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	2	0.7130
Pyrrolysine--tRNA ligase	Q8PWY1	PYLS_METMA	Methanosarcina mazei	2	0.7036
Pyrrolysine--tRNA ligase	Q8PWY1	PYLS_METMA	Methanosarcina mazei	2	0.7036
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7027
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7027

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