14-acetoxy-5,6-dihydrocaryophyllen-7-one - Compound Card

14-acetoxy-5,6-dihydrocaryophyllen-7-one

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14-acetoxy-5,6-dihydrocaryophyllen-7-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC[C@@]1(C)C[C@H]2C1CC(=O)/C(=C\CCC2=C)/COC(=O)C
InChI InChI=1S/C18H26O3/c1-5-18(4)10-15-12(2)7-6-8-14(11-21-13(3)19)17(20)9-16(15)18/h8,15-16H,2,5-7,9-11H2,1,3-4H3/b14-8-/t15-,16?,18+/m1/s1
InChIKey GWGZWWJGPJAMCO-AWUINLEFSA-N
Formula C18H26O3
HBA 3
HBD 0
MW 290.4
Rotatable Bonds 3
TPSA 43.37
LogP 3.84
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 290.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria arabica Asteraceae Plantae 119185

Showing of synonyms

  • Hafez S, Sarg TM, et al. (1987). Caryophyllene derivatives from Pulicaria arabica. Phytochemistry,1987,26(12),3356-3358. [View]
Pubchem: 162816861
Nmrshiftdb2: 70015793

No compound-protein relationship available.

Structure

SMILES: C=C1CCC=CC(=O)CC(C12)CC2

Level: 0

Mol. Weight: 290.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.82
Plasma Protein Binding
66.04
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
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
11.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.57
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.27
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.52
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
-0.31
Rat (Acute)
2.25
Rat (Chronic Oral)
1.87
Fathead Minnow
4.03
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
340.81
Hydration Free Energy
-4.6
Log(D) at pH=7.4
3.2
Log(P)
3.7
Log S
-4.38
Log(Vapor Pressure)
-5.06
Melting Point
51.69
pKa Acid
11.04
pKa Basic
4.53
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 0.9107
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9107
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8409
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8409
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8038
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8038
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7817
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7817
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7800
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7800
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7627
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7627
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7547
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7547
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7412
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7412
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7352
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7352
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7348
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7348
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7342
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7342
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7324
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7324
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7312
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7312
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7158
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7158
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7128
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7128
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7074
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7074
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7050
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7050
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7027
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7027
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7016
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7016
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7014
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7014

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