(2R,3S,6R)-2,6-dimethyl-3,6-epoxyoct-7-enoic acid - Compound Card

(2R,3S,6R)-2,6-dimethyl-3,6-epoxyoct-7-enoic acid

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(2R,3S,6R)-2,6-dimethyl-3,6-epoxyoct-7-enoic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Carboxylic Acid
Canonical Smiles C=C[C@@]1(C)CC[C@H](O1)[C@@H](C(=O)O)C
InChI InChI=1S/C10H16O3/c1-4-10(3)6-5-8(13-10)7(2)9(11)12/h4,7-8H,1,5-6H2,2-3H3,(H,11,12)/t7-,8-,10-/m0/s1
InChIKey SEGYPOKUPWNPPY-NRPADANISA-N
Formula C10H16O3
HBA 2
HBD 1
MW 184.23
Rotatable Bonds 3
TPSA 46.53
LogP 1.83
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 13
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 184.11
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: 102174448
Nmrshiftdb2: 60074971

No compound-protein relationship available.

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 184.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.22
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.28
Plasma Protein Binding
36.21
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
3.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.01
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.78
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.07
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
-1.17
Rat (Acute)
2.2
Rat (Chronic Oral)
1.88
Fathead Minnow
3.67
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
262.43
Hydration Free Energy
-7.19
Log(D) at pH=7.4
-0.82
Log(P)
2.76
Log S
-1.21
Log(Vapor Pressure)
-3.64
Melting Point
50.77
pKa Acid
4.06
pKa Basic
7.25
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9165
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9165
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8440
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8440
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8333
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8333
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8232
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8232
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8053
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8053
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7883
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7883
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7790
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7790
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.7736
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.7736
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7685
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7685
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7594
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7594
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7580
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7580
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7550
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7550
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7542
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7542
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7533
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7533
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7527
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7527
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7511
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7511
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7457
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7457
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7443
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7443
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7422
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7422
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7413
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7413
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7307
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7307
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7297
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7297
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7278
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7278
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7267
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7267
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7200
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7200
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7197
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7197
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7187
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7187
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7182
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7182
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7176
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7176
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7156
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7156
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7146
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7146
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7140
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7140
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7128
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7128
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7113
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7113
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7081
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7081
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7067
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7067
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7051
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7051
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7051
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7051
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7046
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7046
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7009
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7009

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