2-((4aR,7R)-decahydro-4a-methyl-1-methylenenaphthalen-7-yl)acrylic acid - Compound Card

2-((4aR,7R)-decahydro-4a-methyl-1-methylenenaphthalen-7-yl)acrylic acid

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2-((4aR,7R)-decahydro-4a-methyl-1-methylenenaphthalen-7-yl)acrylic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C1CCC[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/h12-13H,1-2,4-9H2,3H3,(H,16,17)/t12-,13?,15-/m1/s1
InChIKey UJQGVDNQDFTTLZ-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: 91746573
Nmrshiftdb2: 60072566

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 234.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.38
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.51
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.84
Plasma Protein Binding
72.65
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
2.69
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.37
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.47
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
0.37
Rat (Acute)
2.84
Rat (Chronic Oral)
1.89
Fathead Minnow
3.93
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
307.63
Hydration Free Energy
-5.55
Log(D) at pH=7.4
1.44
Log(P)
4.61
Log S
-4.37
Log(Vapor Pressure)
-5.6
Melting Point
113.28
pKa Acid
4.99
pKa Basic
7.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9169
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9169
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9129
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9129
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9111
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.9111
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.9111
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9111
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9110
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9110
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9104
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9104
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9052
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9052
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9043
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.9043
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9007
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.9007
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8987
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8987
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8882
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8882
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8791
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8791
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8646
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8646
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8644
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8644
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8630
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8630
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8542
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8542
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8423
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8423
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8287
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8287
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8066
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8066
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8051
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8051
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7838
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7838
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7836
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7836
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7811
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7811
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7764
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7764
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7762
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7762
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7758
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7758
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7693
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7693
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7680
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7680
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7677
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7677
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7655
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7655
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7648
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7648
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7641
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7641
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7635
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7635
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7625
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7625
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7609
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7609
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7603
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7603
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7599
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7599
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7587
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7587
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7582
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7582
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7579
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7579
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7578
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7578
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7577
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7577
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7574
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7574
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7568
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7568
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7565
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7565
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7558
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7558
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7555
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7555
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7555
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7555
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7553
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7553
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7551
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7551
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7550
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7550
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7548
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7548
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7546
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7546
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7545
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7545
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7535
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7535
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7534
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7534
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7533
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7533
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7533
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7533
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7532
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7532
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7530
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7530
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7522
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7522
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7521
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7521
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7518
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7518
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7515
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7515
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7507
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7507
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7505
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7505
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7503
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7503
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7484
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7484
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7481
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7481
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7470
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7470
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7467
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7467
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.7447
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.7447
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7431
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7431
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7423
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7423
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7419
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7419
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7406
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7406
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7386
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7386
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7383
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7383
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7325
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7325
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7310
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7310
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7305
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7305
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7283
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7283
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7264
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7264
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7258
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7258
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7243
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7243
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7224
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7224
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7209
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7209
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7203
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7203
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7198
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7198
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7189
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7189
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7187
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7187
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7148
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7148
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7107
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7107
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7040
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7040

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