(3R,4S,7R)-3,7-dimethyl-4,7-epoxynon-8-enoic acid - Compound Card

(3R,4S,7R)-3,7-dimethyl-4,7-epoxynon-8-enoic acid

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(3R,4S,7R)-3,7-dimethyl-4,7-epoxynon-8-enoic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Carboxylic Acid
Canonical Smiles C[C@@H]([C@@H]1CC[C@](O1)(C)C=C)CC(=O)O
InChI InChI=1S/C11H18O3/c1-4-11(3)6-5-9(14-11)8(2)7-10(12)13/h4,8-9H,1,5-7H2,2-3H3,(H,12,13)/t8-,9+,11+/m1/s1
InChIKey NAJZTTOYWJQEQW-YWVKMMECSA-N
Formula C11H18O3
HBA 2
HBD 1
MW 198.26
Rotatable Bonds 4
TPSA 46.53
LogP 2.22
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 198.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Mako JA, Sanz-Cervera JF, et al. (1994). New germacranolides and eudesmanolides from North African Artemisia herba-alba.. Journal of Natural Products,1994,57(7),939-946. [View]
Pubchem: 162966177
Nmrshiftdb2: 60074958

No compound-protein relationship available.

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 198.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.32
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.29
Plasma Protein Binding
44.17
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
3.74
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.0
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.43
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.69
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
-0.96
Rat (Acute)
2.04
Rat (Chronic Oral)
1.82
Fathead Minnow
3.72
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
275.3
Hydration Free Energy
-6.94
Log(D) at pH=7.4
-0.34
Log(P)
1.96
Log S
-1.34
Log(Vapor Pressure)
-4.08
Melting Point
44.73
pKa Acid
4.28
pKa Basic
7.45
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 0.9228
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9228
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9066
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9066
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8954
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8954
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8903
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8903
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8873
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8873
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8717
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8717
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8696
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8696
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8625
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8625
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8577
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8577
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8474
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8474
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8432
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8432
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8390
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8390
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8385
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8385
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8211
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8211
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8209
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8209
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8166
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8166
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8162
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8162
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8107
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8107
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7956
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7956
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.7935
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.7935
Gibberellin receptor GID1 Q6L545 GID1_ORYSJ Oryza sativa subsp. japonica 3 0.7885
Gibberellin receptor GID1 Q6L545 GID1_ORYSJ Oryza sativa subsp. japonica 3 0.7885
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7829
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7829
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7811
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7811
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7804
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7804
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7655
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7655
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7645
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7645
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7640
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7640
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7638
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7638
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7622
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7622
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7610
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7610
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7582
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7582
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7568
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7568
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7555
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7555
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7537
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7537
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7533
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7533
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7514
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7514
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7514
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7514
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7420
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7420
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7417
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7417
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7411
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7411
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7401
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7401
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7398
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7398
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7392
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7392
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7374
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7374
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7363
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7363
Gibberellin receptor GID1A Q9MAA7 GID1A_ARATH Arabidopsis thaliana 3 0.7343
Gibberellin receptor GID1A Q9MAA7 GID1A_ARATH Arabidopsis thaliana 3 0.7343
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7329
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7329
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7304
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7304
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7300
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7300
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7296
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7296
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7276
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7276
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7266
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7266
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7263
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7263
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7243
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7243
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7243
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7243
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7239
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7239
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7188
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7188
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7186
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7186
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7176
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7176
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7160
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7160
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7150
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7150
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7147
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7147
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7139
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7139
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7114
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7114
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7101
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7101
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7060
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7060
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7055
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7055
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7052
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7052
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7017
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7017

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