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

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

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(1S,5Z,9R)-12,14-dihydroxycaryophylla-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)CO
InChI InChI=1S/C15H22O3/c1-10-4-3-5-11(8-16)14(18)6-13-12(10)7-15(13,2)9-17/h5,12-13,16-17H,1,3-4,6-9H2,2H3/b11-5+/t12-,13-,15-/m1/s1
InChIKey YFJGKPLRMWQNGT-IDMVNGPCSA-N
Formula C15H22O3
HBA 3
HBD 2
MW 250.34
Rotatable Bonds 2
TPSA 57.53
LogP 1.85
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 250.16
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]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 250.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.23
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
51.6
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
9.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.36
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.05
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.94
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
1.46
Rat (Acute)
2.11
Rat (Chronic Oral)
2.06
Fathead Minnow
3.92
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
359.54
Hydration Free Energy
-9.42
Log(D) at pH=7.4
1.09
Log(P)
1.52
Log S
-2.0
Log(Vapor Pressure)
-6.21
Melting Point
127.44
pKa Acid
10.13
pKa Basic
5.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8644
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8584
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8482
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8139
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7948
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7842
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7722
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7613
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7360
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7239
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7107
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7076
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7010

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