2-((2R,4aR)-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethylnaphthalen-2-yl)acrylic acid - Compound Card

2-((2R,4aR)-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethylnaphthalen-2-yl)acrylic acid

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2-((2R,4aR)-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethylnaphthalen-2-yl)acrylic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC1=CCC[C@]2(C1C[C@@H](CC2)C(=C)C(=O)O)C
InChI InChI=1S/C15H22O2/c1-10-5-4-7-15(3)8-6-12(9-13(10)15)11(2)14(16)17/h5,12-13H,2,4,6-9H2,1,3H3,(H,16,17)/t12-,13?,15-/m1/s1
InChIKey UTXMCYDEIZPGME-ILWWEHDPSA-N
Formula C15H22O2
HBA 1
HBD 1
MW 234.34
Rotatable Bonds 2
TPSA 37.3
LogP 3.79
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 234.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cheirolophus mauritanicus Asteraceae Plantae 64998

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: 89043384
Nmrshiftdb2: 60072558

No compound-protein relationship available.

Structure

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 234.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
57.62
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
4.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.41
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.22
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.22
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
0.7
Rat (Acute)
2.23
Rat (Chronic Oral)
2.19
Fathead Minnow
3.92
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
310.88
Hydration Free Energy
-5.44
Log(D) at pH=7.4
1.59
Log(P)
4.63
Log S
-4.02
Log(Vapor Pressure)
-4.89
Melting Point
110.15
pKa Acid
5.05
pKa Basic
8.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9172
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9172
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8953
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8953
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8822
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8822
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8683
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8683
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8509
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8509
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8475
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8475
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7807
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7807
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7757
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7757
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7738
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7738
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7627
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7627
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7527
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7527
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7488
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7488
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7419
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7419
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7391
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7391
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7351
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7351
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7323
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7323
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7204
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7204
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7175
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7175
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7077
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7077
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7037
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7037

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