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

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

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(E)-2-(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(C1CCC(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+
InChIKey WKCHNXVWJKIODW-VQHVLOKHSA-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 judaica Asteraceae Plantae 205369

Showing of synonyms

  • Metwally MA, Jakupovic J, et al. (1985). Eudesmanolides from Artemisia judaica.. Phytochemistry,1985,24(5),1103-1104. [View]
Pubchem: 13833794

No compound-protein relationship available.

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 268.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.53
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
-2.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.320
Plasma Protein Binding
29.14
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.680
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.400
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
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
5.850
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
3.470
Rat (Acute)
2.370
Rat (Chronic Oral)
1.620
Fathead Minnow
4.220
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
287.560
Hydration Free Energy
-10.080
Log(D) at pH=7.4
1.550
Log(P)
2.44
Log S
-2.25
Log(Vapor Pressure)
-4.23
Melting Point
51.09
pKa Acid
10.03
pKa Basic
4.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9363
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9363
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7848
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7848
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7756
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7756
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7735
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7735
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7714
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7714
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7698
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7698
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7695
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7695
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7684
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7684
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7648
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7648
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7629
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7629
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7541
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7541
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7476
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7476
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7475
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7475
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7313
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7313
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7279
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7279
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7277
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7277
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7255
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7255
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7235
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7235
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7228
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7228
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7220
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7220
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7209
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7209
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7187
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7187
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7167
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7167
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7135
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7135
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7122
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7122
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7118
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7118
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7082
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7082
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7068
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7068
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7062
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7062
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7015
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7015
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7012
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7012
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7009
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7009

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