5-hydroxy-5,6-secocaryophyllen-6-one - Compound Card

5-hydroxy-5,6-secocaryophyllen-6-one

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5-hydroxy-5,6-secocaryophyllen-6-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OCCCC(=C)C1CC(C1CCC(=O)C)(C)C
InChI InChI=1S/C15H26O2/c1-11(6-5-9-16)13-10-15(3,4)14(13)8-7-12(2)17/h13-14,16H,1,5-10H2,2-4H3
InChIKey MAIZBVUEICRYMG-UHFFFAOYSA-N
Formula C15H26O2
HBA 2
HBD 1
MW 238.37
Rotatable Bonds 7
TPSA 37.3
LogP 3.35
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 238.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Achillea ligustica Asteraceae Plantae 282745

Showing of synonyms

  • Mahmoud AA, Al-Shihry SS, et al. (2012). A new epimeric sesquiterpene lactone from Achillea ligustica.. Records of Natural Products,2012,6(1),21-27. [View]
Pubchem: 14682847

No compound-protein relationship available.

Structure

SMILES: C1CCC1

Level: 0

Mol. Weight: 238.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.56
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.36
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.76

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.63
Plasma Protein Binding
21.53
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.91
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.42
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.26
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.61
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
2.61
Rat (Acute)
1.95
Rat (Chronic Oral)
1.55
Fathead Minnow
4.07
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
304.98
Hydration Free Energy
-4.63
Log(D) at pH=7.4
2.21
Log(P)
2.95
Log S
-3.32
Log(Vapor Pressure)
-4.39
Melting Point
29.4
pKa Acid
11.26
pKa Basic
5.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.9238
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.9238
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9025
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9025
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9022
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9022
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8872
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8872
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8727
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8727
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8226
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8226
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7736
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7736
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7595
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7595
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7525
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7525
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7406
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7406
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7380
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7380
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7325
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7325
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7279
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7279
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7192
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7192
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7177
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7177
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7148
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7148
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7028
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7028
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7020
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7020

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