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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • 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-SEGWNZTKSA-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 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: 162904297

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 306.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.47
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
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.700
Plasma Protein Binding
57.23
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
11.720
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.320
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.080
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.220
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
-2.020
Rat (Acute)
2.750
Rat (Chronic Oral)
1.730
Fathead Minnow
4.030
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
344.380
Hydration Free Energy
-5.150
Log(D) at pH=7.4
2.360
Log(P)
2.71
Log S
-3.27
Log(Vapor Pressure)
-5.25
Melting Point
77.48
pKa Acid
9.74
pKa Basic
4.45
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 0.8711
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8711
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8382
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8382
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7845
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7845
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7769
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7769
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7725
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7725
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7634
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7634
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7460
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7460
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7448
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7448
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7336
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7336
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7268
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7268
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7265
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7265
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7252
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7252
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7217
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7217
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7089
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7089
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7048
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7048
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7047
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7047

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