(5Z)-14-hydroxycaryophyllen-7-one - Compound Card

(5Z)-14-hydroxycaryophyllen-7-one

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(5Z)-14-hydroxycaryophyllen-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)C
InChI InChI=1S/C15H22O2/c1-10-5-4-6-11(9-16)14(17)7-13-12(10)8-15(13,2)3/h6,12-13,16H,1,4-5,7-9H2,2-3H3/b11-6+/t12-,13-/m1/s1
InChIKey GVUHIWDAWNDBKR-WXYBXBMJSA-N
Formula C15H22O2
HBA 2
HBD 1
MW 234.34
Rotatable Bonds 1
TPSA 37.3
LogP 2.88
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 234.16
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]
Pubchem: 13970044

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 234.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.27
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
55.52
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.51
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.14
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.34
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
2.43
Rat (Acute)
2.02
Rat (Chronic Oral)
1.81
Fathead Minnow
4.04
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
325.91
Hydration Free Energy
-6.64
Log(D) at pH=7.4
2.09
Log(P)
2.78
Log S
-3.08
Log(Vapor Pressure)
-4.71
Melting Point
95.51
pKa Acid
10.7
pKa Basic
4.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.9279
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8608
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8492
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8154
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7755
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7077
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7063
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7049

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