1S-(2E)-5-[(1R)-2,2-dimethyl-6-methylidenecyclohexyl]-3-methylpent-2-enoic acid - Compound Card

1S-(2E)-5-[(1R)-2,2-dimethyl-6-methylidenecyclohexyl]-3-methylpent-2-enoic acid

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1S-(2E)-5-[(1R)-2,2-dimethyl-6-methylidenecyclohexyl]-3-methylpent-2-enoic acid

Structure
Zoomed Structure
  • Family: Fungi - Hymenochaetaceae
  • Kingdom: Fungi
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C/C(=C\C(=O)O)/CC[C@@H]1C(=C)CCCC1(C)C
InChI InChI=1S/C15H24O2/c1-11(10-14(16)17)7-8-13-12(2)6-5-9-15(13,3)4/h10,13H,2,5-9H2,1,3-4H3,(H,16,17)/b11-10+/t13-/m1/s1
InChIKey WGEZRSYMRXPKPN-OCHBPSSRSA-N
Formula C15H24O2
HBA 1
HBD 1
MW 236.35
Rotatable Bonds 4
TPSA 37.3
LogP 4.18
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 236.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sanghuangporus sp. Hymenochaetaceae Fungi 2267874

Showing of synonyms

  • Chepkirui C, Cheng T, et al. (2018). An unprecedented spiro [furan-2,1’-indene]-3-one derivative and other nematicidal and antimicrobial metabolites from Sanghuangporus sp. (Hymenochaetaceae, Basidiomycota) collected in Kenya. Phytochemistry Letters,2018,25,141-146.. [View] [PubMed]
Pubchem: 137333517
Nmrshiftdb2: 70108078

No compound-protein relationship available.

Structure

SMILES: C=C1CCCCC1

Level: 0

Mol. Weight: 236.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.84
Plasma Protein Binding
70.77
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
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
1.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.74
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.44
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.09
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
1.6
Rat (Acute)
2.18
Rat (Chronic Oral)
1.77
Fathead Minnow
3.99
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
304.71
Hydration Free Energy
-5.69
Log(D) at pH=7.4
1.48
Log(P)
5.12
Log S
-4.11
Log(Vapor Pressure)
-5.14
Melting Point
101.85
pKa Acid
5.81
pKa Basic
7.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9304
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9304
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9213
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9213
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.9016
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.9016
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8837
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8837
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8785
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8785
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8736
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8736
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8727
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8727
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8705
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8705
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8677
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8677
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8616
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8616
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8527
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8527
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8495
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8495
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8439
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8439
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8388
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8388
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8287
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8287
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8278
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8278
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8252
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8252
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8219
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8219
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8121
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8121
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8041
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8041
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7944
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7944
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7914
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7914
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7864
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7864
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7815
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7815
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7796
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7796
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7795
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7795
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7758
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7758
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7709
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7709
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7699
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7699
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7647
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7647
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7610
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7610
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7608
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7608
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7575
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7575
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7559
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7559
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7557
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7557
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7534
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7534
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7523
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7523
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7519
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7519
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7503
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7503
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7497
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7497
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7486
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7486
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7474
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7474
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7473
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7473
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7452
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7452
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7444
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7444
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7438
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7438
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7435
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7435
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7426
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7426
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7420
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7420
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7415
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7415
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7409
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7409
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7394
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7394
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7388
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7388
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7348
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7348
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7332
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7332
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7329
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7329
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7311
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7311
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7282
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7282
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7268
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7268
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7263
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7263
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7223
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7223
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7201
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7201
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7172
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7172
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7162
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7162
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7157
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7157
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7133
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7133
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7128
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7128
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7116
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7116
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7089
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7089
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7087
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7087
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7085
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7085
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7083
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7083
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7082
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7082
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7080
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7080
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7066
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7066
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7042
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7042
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7037
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7037
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7037
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7037
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7033
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7033
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7023
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7023
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7018
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7018

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