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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles C=C[C@@]1(C)CC[C@H](O1)[C@@H](C(=O)/C=C/C(O)(C)C)C
InChI InChI=1S/C15H24O3/c1-6-15(5)10-8-13(18-15)11(2)12(16)7-9-14(3,4)17/h6-7,9,11,13,17H,1,8,10H2,2-5H3/b9-7+/t11-,13+,15+/m1/s1
InChIKey WQUKMIHCFQFPQG-BSCSQGBWSA-N
Formula C15H24O3
HBA 3
HBD 1
MW 252.35
Rotatable Bonds 5
TPSA 46.53
LogP 2.64
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 252.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329
2 Artemisia reptans Asteraceae Plantae 72350
3 Artemisia hugueti Asteraceae Plantae 4219
4 Artemisia ifranensis Asteraceae Plantae 1903206

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]
  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones and acetylenes from Artemisia reptans.. Phytochemistry,1994,37(4),1055-1099. [View]
  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones from North African Artemisia species.. Phytochemistry,1994,37(2),477-485. [View]
Pubchem: 12132773
Nmrshiftdb2: 60080295

No compound-protein relationship available.

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 252.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.16
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.25
Plasma Protein Binding
47.87
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
6.33
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.89
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.73
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.66
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
-0.63
Rat (Acute)
2.3
Rat (Chronic Oral)
1.51
Fathead Minnow
3.97
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
293.21
Hydration Free Energy
-6.74
Log(D) at pH=7.4
1.63
Log(P)
2.48
Log S
-2.26
Log(Vapor Pressure)
-3.91
Melting Point
62.38
pKa Acid
10.37
pKa Basic
5.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.9062
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.9062
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8862
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8862
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8761
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8761
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8568
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8568
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8504
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8504
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8374
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8374
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.8279
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.8279
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8170
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8170
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8023
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8023
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7972
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7972
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7930
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7930
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7898
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7898
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7824
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7824
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7769
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7769
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7648
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7648
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7622
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7622
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7587
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7587
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7519
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7519
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7476
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7476
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7429
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7429
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7370
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7370
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7358
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7358
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7326
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7326
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7276
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7276
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7269
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7269
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7260
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7260
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7239
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7239
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7238
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7238
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7215
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7215
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7214
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7214
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7201
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7201
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7193
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7193
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7185
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7185
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7182
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7182
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7161
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7161
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7145
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7145
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7142
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7142
Vitamin D3 receptor A Q9PTN2 VDRA_DANRE Danio rerio 3 0.7139
Vitamin D3 receptor A Q9PTN2 VDRA_DANRE Danio rerio 3 0.7139
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7137
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7137
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7104
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7104
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7090
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7090
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7079
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7079
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7070
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7070
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7053
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7053
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7044
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7044
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7040
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7040
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7036
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7036
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7034
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7034
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7023
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7023
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7020
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7020
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7019
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7019

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