12-acetoxy-5alpha-methoxy-6(14)-dehydro-5,6-dihydrocaryophyllen-7-one - Compound Card

12-acetoxy-5alpha-methoxy-6(14)-dehydro-5,6-dihydrocaryophyllen-7-one

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12-acetoxy-5alpha-methoxy-6(14)-dehydro-5,6-dihydrocaryophyllen-7-one

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CO[C@H]1CCC(=C)[C@@H]2C(CC(=O)C1=C)[C@@](C2)(C)COC(=O)C
InChI InChI=1S/C18H26O4/c1-11-6-7-17(21-5)12(2)16(20)8-15-14(11)9-18(15,4)10-22-13(3)19/h14-15,17H,1-2,6-10H2,3-5H3/t14-,15?,17+,18-/m1/s1
InChIKey DZYFVCXNJAYEPO-IOVMHBDKSA-N
Formula C18H26O4
HBA 4
HBD 0
MW 306.4
Rotatable Bonds 3
TPSA 52.6
LogP 3.07
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 306.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria arabica Asteraceae-Compositae 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: 162904298

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC(=C)C(=O)CC(C12)CC2

Level: 0

Mol. Weight: 190.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.710
Plasma Protein Binding
56.84
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
11.620
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.310
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.120
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.150
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
-2.290
Rat (Acute)
2.740
Rat (Chronic Oral)
1.700
Fathead Minnow
4.000
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
344.640
Hydration Free Energy
-5.240
Log(D) at pH=7.4
2.400
Log(P)
2.79
Log S
-3.23
Log(Vapor Pressure)
-5.24
Melting Point
72.37
pKa Acid
9.68
pKa Basic
4.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9699
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9699
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9528
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9528
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8915
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8915
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8306
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8306
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7876
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7876
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7804
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7804
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7562
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7562
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7431
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7431
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7315
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7315
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7241
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7241
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7199
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7199
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7189
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7189
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7162
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7162
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7114
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7114
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7086
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7086
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7078
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7078
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7049
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7049
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7027
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7027
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7021
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7021

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