Diepoxyrollin - Compound Card

Diepoxyrollin

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Diepoxyrollin

Structure
Zoomed Structure
  • Family: 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.

Structure

SMILES: O=C1OCC=C1CCCCCCCCCCCC2C(O2)CCC3CO3

Level: 2

Mol. Weight: 350.5 g/mol

Structure

SMILES: O1CC1CCCCCCCCCCCC2=CCOC2=O

Level: 1

Mol. Weight: 280.41 g/mol

Structure

SMILES: O1CC1CCC2CO2

Level: 1

Mol. Weight: 114.14 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 84.07 g/mol

Structure

SMILES: C1CO1

Level: 0

Mol. Weight: 44.05 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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