Methyl-6-acetoxy-9-oxo-1(10)Z,7Z-alpha-humulene-15-oate - Compound Card

Methyl-6-acetoxy-9-oxo-1(10)Z,7Z-alpha-humulene-15-oate

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Methyl-6-acetoxy-9-oxo-1(10)Z,7Z-alpha-humulene-15-oate

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles COC(=O)/C/1=C/[C@@H](OC(=O)C)C(C)(C)/C=C\C(=O)/C(=C\CC1)/C
InChI InChI=1S/C18H24O5/c1-12-7-6-8-14(17(21)22-5)11-16(23-13(2)19)18(3,4)10-9-15(12)20/h7,9-11,16H,6,8H2,1-5H3/b10-9-,12-7-,14-11+/t16-/m1/s1
InChIKey CLNDAYOHEVNSFF-JSMVRMJPSA-N
Formula C18H24O5
HBA 5
HBD 0
MW 320.39
Rotatable Bonds 2
TPSA 69.67
LogP 2.91
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 320.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Asteriscus graveolens Asteraceae 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: 163003405

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCCC=CCCC=C1

Level: 0

Mol. Weight: 320.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.450
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.400
Plasma Protein Binding
60.21
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
5.630
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.420
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.870
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.640
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
-0.360
Rat (Acute)
2.130
Rat (Chronic Oral)
1.900
Fathead Minnow
4.450
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
345.950
Hydration Free Energy
-7.420
Log(D) at pH=7.4
2.290
Log(P)
2.76
Log S
-3.18
Log(Vapor Pressure)
-5.15
Melting Point
75.79
pKa Acid
10.55
pKa Basic
4.08
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 0.8686
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8686
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8002
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8002
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7993
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7993
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7985
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7985
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7960
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7960
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7503
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7503
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7430
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7430
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7403
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7403
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7393
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7393
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7229
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7229
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7228
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7228
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7185
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7185
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7166
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7166
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7003
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7003

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