(6S,7S,10R)-7,10-epoxy-3-hydroxy-2,6,10-trimethyl- dodeca-1,3,11-trien-5-one - Compound Card

(6S,7S,10R)-7,10-epoxy-3-hydroxy-2,6,10-trimethyl- dodeca-1,3,11-trien-5-one

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(6S,7S,10R)-7,10-epoxy-3-hydroxy-2,6,10-trimethyl- dodeca-1,3,11-trien-5-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C[C@@]1(C)CC[C@H](O1)[C@@H](C(=O)/C=C(/C(=C)C)\O)C
InChI InChI=1S/C15H22O3/c1-6-15(5)8-7-14(18-15)11(4)13(17)9-12(16)10(2)3/h6,9,11,14,16H,1-2,7-8H2,3-5H3/b12-9-/t11-,14+,15+/m1/s1
InChIKey AYJCMTOVQWMEDB-WHVFMQMESA-N
Formula C15H22O3
HBA 3
HBD 1
MW 250.34
Rotatable Bonds 5
TPSA 46.53
LogP 3.33
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 250.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia reptans Asteraceae Plantae 72350

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones and acetylenes from Artemisia reptans.. Phytochemistry,1994,37(4),1055-1099. [View]
Pubchem: 12132772
Nmrshiftdb2: 60080290

No compound-protein relationship available.

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 250.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.03
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)
0.36
Plasma Protein Binding
53.45
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
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
7.39
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.4
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.46
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.47
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
-0.46
Rat (Acute)
2.6
Rat (Chronic Oral)
1.67
Fathead Minnow
3.95
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
297.82
Hydration Free Energy
-7.8
Log(D) at pH=7.4
1.7
Log(P)
2.73
Log S
-2.61
Log(Vapor Pressure)
-5.21
Melting Point
60.25
pKa Acid
9.36
pKa Basic
4.9
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9224
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9224
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8687
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8687
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8561
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8561
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8269
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8269
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8248
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8248
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8009
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8009
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7821
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7821
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7650
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7650
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7645
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7645
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7629
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7629
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7590
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7590
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7403
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7403
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7394
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7394
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7387
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7387
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7353
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7353
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7289
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7289
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7252
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7252
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7243
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7243
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7201
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7201
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7197
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7197
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7170
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7170
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7108
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7108
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7103
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7103
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7095
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7095
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7056
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7056
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7048
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7048

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