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2-[(1R,5S)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoic acid
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | CC(=O)CCC1=CC[C@@H](CC[C@@H]1C)C(=C)C(=O)O |
|---|---|
| InChI | InChI=1S/C15H22O3/c1-10-4-6-14(12(3)15(17)18)9-8-13(10)7-5-11(2)16/h8,10,14H,3-7,9H2,1-2H3,(H,17,18)/t10-,14+/m0/s1 |
| InChIKey | NIQIMYXBAQAIAT-IINYFYTJSA-N |
| Formula | C15H22O3 |
| HBA | 2 |
| HBD | 1 |
| MW | 250.34 |
| Rotatable Bonds | 5 |
| TPSA | 54.37 |
| LogP | 3.36 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 250.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Xanthium pungens | Asteraceae | Plantae | 1979456 |
Showing of synonyms
2-[(1R,5S)-5-methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl]prop-2-enoic acid
4-Oxobedfordiaic acid
68799-38-2
2-((1R,5S)-5-Methyl-4-(3-oxobutyl)cyclohept-3-en-1-yl)acrylic acid
Starbld0007367
HY-N2643
AKOS032962216
FS-8961
DA-49755
CS-0023061
(1R,5S)-5-Methyl--methylene-4-(3-oxobutyl)-3-cycloheptene-1-acetic acid
3-Cycloheptene-1-acetic acid, 5-methyl--methylene-4-(3-oxobutyl)-, (1R-cis)-
- Ahmed AA, Jakupovic J, et al. (1990). Sesquiterpene lactones from Xanthium pungens. Phytochemistry,1990,29(7),2211-2215. [View]
No compound-protein relationship available.
SMILES: C1=CCCCCC1
Level: 0
Mol. Weight: 250.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.71
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.57
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.26
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.62
- Plasma Protein Binding
- 57.76
- 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
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- 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
- 4.29
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.03
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.88
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.13
- Micronucleos
- Safe
- 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
- -0.02
- Rat (Acute)
- 2.09
- Rat (Chronic Oral)
- 2.31
- Fathead Minnow
- 3.92
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 324.2
- Hydration Free Energy
- -6.81
- Log(D) at pH=7.4
- 0.22
- Log(P)
- 2.83
- Log S
- -2.99
- Log(Vapor Pressure)
- -5.5
- Melting Point
- 90.79
- pKa Acid
- 4.86
- pKa Basic
- 8.06
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.9729 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.9729 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.9427 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.9427 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.8952 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.8952 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8782 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8782 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.8650 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.8650 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8409 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8409 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 3 | 0.8340 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 3 | 0.8340 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 3 | 0.8336 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 3 | 0.8336 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8287 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8287 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8105 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8105 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8050 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8050 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7691 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7691 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7630 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7630 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7581 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7581 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7573 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7573 |
| Lactaldehyde dehydrogenase | P25553 | ALDA_ECOLI | Escherichia coli | 3 | 0.7479 |
| Lactaldehyde dehydrogenase | P25553 | ALDA_ECOLI | Escherichia coli | 3 | 0.7479 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7445 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7445 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7426 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7426 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7425 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7425 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7416 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7416 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7409 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7409 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7383 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7383 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7373 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7373 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7338 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7338 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 2 | 0.7336 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 2 | 0.7336 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7324 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7324 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7298 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7298 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7288 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7288 |
| Avd protein | A7YYL1 | A7YYL1_XENTR | Xenopus tropicalis | 3 | 0.7259 |
| Avd protein | A7YYL1 | A7YYL1_XENTR | Xenopus tropicalis | 3 | 0.7259 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7218 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7218 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7195 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7195 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7160 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7160 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7137 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7137 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7084 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7084 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7062 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7062 |
| Geranyl diphosphate synthase large subunit | Q9SBR3 | Q9SBR3_MENPI | Mentha piperita | 3 | 0.7051 |
| Geranyl diphosphate synthase large subunit | Q9SBR3 | Q9SBR3_MENPI | Mentha piperita | 3 | 0.7051 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7047 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7047 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7027 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7027 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7023 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7023 |
| Ferrichrome outer membrane transporter/phage receptor | P06971 | FHUA_ECOLI | Escherichia coli | 3 | 0.7016 |
| Ferrichrome outer membrane transporter/phage receptor | P06971 | FHUA_ECOLI | Escherichia coli | 3 | 0.7016 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7006 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7006 |