Methyl-9-oxo-1(10)Z,7Z-alpha-humulene-15-oate - Compound Card

Methyl-9-oxo-1(10)Z,7Z-alpha-humulene-15-oate

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Methyl-9-oxo-1(10)Z,7Z-alpha-humulene-15-oate

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles COC(=O)/C/1=C/CC(C)(C)/C=C\C(=O)/C(=C\CC1)/C
InChI InChI=1S/C16H22O3/c1-12-6-5-7-13(15(18)19-4)8-10-16(2,3)11-9-14(12)17/h6,8-9,11H,5,7,10H2,1-4H3/b11-9-,12-6-,13-8+
InChIKey OPNKSPPKQUMBSL-ZMVLXVBASA-N
Formula C16H22O3
HBA 3
HBD 0
MW 262.35
Rotatable Bonds 1
TPSA 43.37
LogP 3.37
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 262.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Asteriscus graveolens Asteraceae-Compositae Plantae 73976

Showing of synonyms

  • El Dahmy S, Jakupovic J, et al. (1985). New humulene derivatives from Asteriscus graveolens.. Tetrahedron,1985,41(2),309-316. [View]
Pubchem: 101114181
Nmrshiftdb2: 70005333

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCCC=CCCC=C1

Level: 0

Mol. Weight: 162.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.190
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.500
Plasma Protein Binding
65.7
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-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
4.940
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.470
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.640
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.070
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
2.050
Rat (Acute)
1.960
Rat (Chronic Oral)
1.900
Fathead Minnow
4.440
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
317.850
Hydration Free Energy
-5.960
Log(D) at pH=7.4
3.030
Log(P)
3.26
Log S
-3.64
Log(Vapor Pressure)
-3.91
Melting Point
55.55
pKa Acid
10.69
pKa Basic
4.8
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 0.9214
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9214
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8783
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8783
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8702
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8702
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8394
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8394
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8313
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8313
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8154
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8154
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7759
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7759
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7508
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7508
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7504
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7504
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7340
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7340
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7300
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7300
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7258
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7258
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7233
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7233
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7164
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7164
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7103
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7103
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7038
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7038
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7033
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7033

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