(1S,5Z,9R)-12-acetoxy-14-hydroxycaryophylla-2(15),5-dien-7-one - Compound Card

(1S,5Z,9R)-12-acetoxy-14-hydroxycaryophylla-2(15),5-dien-7-one

Select a section from the left sidebar

(1S,5Z,9R)-12-acetoxy-14-hydroxycaryophylla-2(15),5-dien-7-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC/C/1=C\CCC(=C)[C@@H]2[C@@H](CC1=O)[C@@](C2)(C)OC(=O)C
InChI InChI=1S/C16H22O4/c1-10-5-4-6-12(9-17)15(19)7-14-13(10)8-16(14,3)20-11(2)18/h6,13-14,17H,1,4-5,7-9H2,2-3H3/b12-6+/t13-,14-,16+/m1/s1
InChIKey MSICCRYOZMANMI-SUCCEKNJSA-N
Formula C16H22O4
HBA 4
HBD 1
MW 278.35
Rotatable Bonds 2
TPSA 63.6
LogP 2.17
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 278.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria vulgaris Asteraceae Plantae 119191

Showing of synonyms

  • Zardi-Bergaoui A, Znati M, et al. (2023). Caryophyllene sesquiterpenes from Pulicaria vulgaris GAERTN.:Isolation, structure determination, bioactivity and structure-activity relationship. Natural product research, 2023, 37(1), 123-129. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 278.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.45
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.57
Plasma Protein Binding
51.57
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
Non-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
8.08
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.13
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.34
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.75
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)
2.45
Rat (Chronic Oral)
1.97
Fathead Minnow
3.97
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
344.72
Hydration Free Energy
-8.15
Log(D) at pH=7.4
1.42
Log(P)
1.65
Log S
-2.45
Log(Vapor Pressure)
-5.48
Melting Point
102.14
pKa Acid
10.05
pKa Basic
4.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8528
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8517
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7981
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7487
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7390
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7381
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7274
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7224
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7133
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7070

Download SDF