(S,E)-2-((2S,5R)-tetrahydro-5-methyl-5-vinylfuran-2-yl)-6-hydroperoxy-6-methylhept-4-en-3-one - Compound Card

(S,E)-2-((2S,5R)-tetrahydro-5-methyl-5-vinylfuran-2-yl)-6-hydroperoxy-6-methylhept-4-en-3-one

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(S,E)-2-((2S,5R)-tetrahydro-5-methyl-5-vinylfuran-2-yl)-6-hydroperoxy-6-methylhept-4-en-3-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OOC(/C=C/C(=O)[C@H]([C@@H]1CC[C@](O1)(C)C=C)C)(C)C
InChI InChI=1S/C15H24O4/c1-6-15(5)10-8-13(18-15)11(2)12(16)7-9-14(3,4)19-17/h6-7,9,11,13,17H,1,8,10H2,2-5H3/b9-7+/t11-,13+,15+/m1/s1
InChIKey WKCHNXVWJKIODW-BSCSQGBWSA-N
Formula C15H24O4
HBA 4
HBD 1
MW 268.35
Rotatable Bonds 6
TPSA 55.76
LogP 3.14
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 268.17
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: 12132774
Nmrshiftdb2: 60074960

No compound-protein relationship available.

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 268.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.52
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.220
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.320
Plasma Protein Binding
56.57
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.830
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.170
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.570
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.790
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
-0.130
Rat (Acute)
2.380
Rat (Chronic Oral)
1.610
Fathead Minnow
4.040
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
291.240
Hydration Free Energy
-10.110
Log(D) at pH=7.4
1.500
Log(P)
2.14
Log S
-2.34
Log(Vapor Pressure)
-4.34
Melting Point
68.08
pKa Acid
9.92
pKa Basic
4.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8098
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8098
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8073
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.8073
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8073
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.8073
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7969
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7969
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7965
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7965
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7858
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7858
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7826
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7826
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7784
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7784
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7716
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7716
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7664
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7664
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7623
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7623
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7611
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7611
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7608
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7608
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7602
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7602
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7559
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7559
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7550
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7550
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7545
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7545
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7531
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7531
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7513
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7513
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7466
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7466
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7439
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7439
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7334
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7334
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7315
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7315
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7282
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7282
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7275
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7275
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7274
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7274
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7274
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7274
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7215
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7215
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7199
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7199
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7187
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7187
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7153
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7153
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7152
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7152
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 4 0.7079
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 4 0.7079
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7057
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7057
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7043
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7043
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7018
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7018

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