2-((4aS,7R)-1,2,4a,5,6,7,8,8a-octahydro-4a-methyl-1-methylene-2-oxonaphthalen-7-yl)acrylic acid - Compound Card

2-((4aS,7R)-1,2,4a,5,6,7,8,8a-octahydro-4a-methyl-1-methylene-2-oxonaphthalen-7-yl)acrylic acid

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2-((4aS,7R)-1,2,4a,5,6,7,8,8a-octahydro-4a-methyl-1-methylene-2-oxonaphthalen-7-yl)acrylic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC(=O)C(=C)[C@@H]1CC[C@@]2(C(C1)C(=C)C(=O)C=C2)C
InChI InChI=1S/C15H18O3/c1-9(14(17)18)11-4-6-15(3)7-5-13(16)10(2)12(15)8-11/h5,7,11-12H,1-2,4,6,8H2,3H3,(H,17,18)/t11-,12?,15+/m1/s1
InChIKey QJVGVRZZNZSYMG-YOMIOTDVSA-N
Formula C15H18O3
HBA 2
HBD 1
MW 246.31
Rotatable Bonds 2
TPSA 54.37
LogP 2.74
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 246.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cheirolophus sempervirens Asteraceae Plantae 65000
2 Cheirolophus x hortigenus Asteraceae Plantae 41544

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem: 14466180
Nmrshiftdb2: 60072565

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)C=CC(C12)CCCC2

Level: 0

Mol. Weight: 246.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.65
Plasma Protein Binding
71.55
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.06
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.31
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.8
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
1.61
Rat (Acute)
2.55
Rat (Chronic Oral)
2.21
Fathead Minnow
3.96
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
332.77
Hydration Free Energy
-8.23
Log(D) at pH=7.4
0.23
Log(P)
2.39
Log S
-3.32
Log(Vapor Pressure)
-6.53
Melting Point
147.96
pKa Acid
4.8
pKa Basic
6.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8474
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8474
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.8025
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.8025
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7739
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7739
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7655
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7655
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7632
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7632
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7557
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7557
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7195
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7195
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7193
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7193
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7150
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7150
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7147
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7147
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7113
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7113
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7094
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7094
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7047
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7047
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7020
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7020
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7016
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7016

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