(1S,6R,9S,11R)-13,14-dihdroxycaryophyll-2(15)-en-7-one - Compound Card

(1S,6R,9S,11R)-13,14-dihdroxycaryophyll-2(15)-en-7-one

Select a section from the left sidebar

(1S,6R,9S,11R)-13,14-dihdroxycaryophyll-2(15)-en-7-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC[C@H]1CCCC(=C)[C@@H]2[C@H](CC1=O)[C@](C2)(C)CO
InChI InChI=1S/C15H24O3/c1-10-4-3-5-11(8-16)14(18)6-13-12(10)7-15(13,2)9-17/h11-13,16-17H,1,3-9H2,2H3/t11-,12-,13+,15+/m1/s1
InChIKey YFBXOWRALDUHFB-CXTNEJHOSA-N
Formula C15H24O3
HBA 3
HBD 2
MW 252.35
Rotatable Bonds 2
TPSA 57.53
LogP 1.93
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 252.17
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=C1CCCCC(=O)CC(C12)CC2

Level: 0

Mol. Weight: 252.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.300
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.590
Plasma Protein Binding
49.05
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
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
11.880
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.480
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
3.930
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
-0.480
Rat (Acute)
1.980
Rat (Chronic Oral)
2.020
Fathead Minnow
3.850
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
359.800
Hydration Free Energy
-8.670
Log(D) at pH=7.4
1.070
Log(P)
1.72
Log S
-1.78
Log(Vapor Pressure)
-6.27
Melting Point
123.41
pKa Acid
10.59
pKa Basic
6.3
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 0.8580
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8236
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7925
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7859
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7705
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7559
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7493
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7307
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7268
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7163
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7092

Download SDF