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Diepoxyrollin

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Acetogenin

Canonical Smiles	CCCCCCCCCCCCCCC1OC1CCC1OC1CCCCCCCCCCCC1=CC(OC1=O)C
InChI	InChI=1S/C36H64O4/c1-3-4-5-6-7-8-9-10-13-16-19-22-25-32-34(39-32)27-28-35-33(40-35)26-23-20-17-14-11-12-15-18-21-24-31-29-30(2)38-36(31)37/h29-30,32-35H,3-28H2,1-2H3
InChIKey	XUXHBERDFQGNOB-UHFFFAOYSA-N
Formula	C₃₆H₆₄O₄
HBA	4
HBD	0
MW	560.9
Rotatable Bonds	28
TPSA	51.36
LogP	10.56
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.92
Exact Mass	560.48
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]

No compound-protein relationship available.

SMILES: O=C1OCC=C1CCCCCCCCCCCC2C(O2)CCC3CO3

Level: 2

Mol. Weight: 560.9 g/mol

SMILES: O1CC1CCCCCCCCCCCC2=CCOC2=O

Level: 1

Mol. Weight: 560.9 g/mol

SMILES: O1CC1CCC2CO2

Level: 1

Mol. Weight: 560.9 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 560.9 g/mol

SMILES: C1CO1

Level: 0

Mol. Weight: 560.9 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: -4.47
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.21

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 2.12
Plasma Protein Binding: 27.11
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: 7.03
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.07
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.07
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.95
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: -7553.4
Rat (Acute): 1.82
Rat (Chronic Oral): 1.78
Fathead Minnow: 22.81
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: 358.81
Hydration Free Energy: -2.84
Log(D) at pH=7.4: 7.66
Log(P): 11.71
Log S: -7.03
Log(Vapor Pressure): -12.27
Melting Point: 33.85
pKa Acid: 8.06
pKa Basic: 3.36

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8679
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8679
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8357
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8357
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7890
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7890
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7785
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7785
Ferrichrome outer membrane transporter/phage receptor	P06971	FHUA_ECOLI	Escherichia coli	3	0.7702
Ferrichrome outer membrane transporter/phage receptor	P06971	FHUA_ECOLI	Escherichia coli	3	0.7702
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7619
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7619
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7601
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7601
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	2	0.7503
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7503
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	2	0.7503
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7503
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	2	0.7487
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	2	0.7487
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7471
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7471
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7436
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7436
Peptidoglycan recognition protein 1	Q9GK12	PGRP1_CAMDR	Camelus dromedarius	3	0.7416
Peptidoglycan recognition protein 1	Q9GK12	PGRP1_CAMDR	Camelus dromedarius	3	0.7416
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7376
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7376
Carnitine O-acetyltransferase	P47934	CACP_MOUSE	Mus musculus	2	0.7368
Carnitine O-acetyltransferase	P47934	CACP_MOUSE	Mus musculus	2	0.7368
Alanine aminotransferase	Q9P9M8	Q9P9M8_9EURY	Pyrococcus furiosus	2	0.7364
Alanine aminotransferase	Q9P9M8	Q9P9M8_9EURY	Pyrococcus furiosus	2	0.7364
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7313
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7313
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7291
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7291
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7266
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7266
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	2	0.7245
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	2	0.7245
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7213
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7213
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7211
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	2	0.7211
thiamine diphosphokinase	Q82ZE3	Q82ZE3_ENTFA	Enterococcus faecalis	2	0.7188
thiamine diphosphokinase	Q82ZE3	Q82ZE3_ENTFA	Enterococcus faecalis	2	0.7188
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7184
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7184
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7137
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7137
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	2	0.7128
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	2	0.7128
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7115
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7115
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7048
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7048
Pyrrolysine--tRNA ligase	Q8PWY1	PYLS_METMA	Methanosarcina mazei	2	0.7036
Pyrrolysine--tRNA ligase	Q8PWY1	PYLS_METMA	Methanosarcina mazei	2	0.7036

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