2-hydroxy-5btetahoxy-6(14)-dehydro-5,6-dihydrocaryophyllen-7-one - Compound Card

2-hydroxy-5btetahoxy-6(14)-dehydro-5,6-dihydrocaryophyllen-7-one

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2-hydroxy-5btetahoxy-6(14)-dehydro-5,6-dihydrocaryophyllen-7-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CO[C@@H]1CCC(=C)[C@@H]2C(CC(=O)C1=C)[C@@](C2)(C)CO
InChI InChI=1S/C16H24O3/c1-10-5-6-15(19-4)11(2)14(18)7-13-12(10)8-16(13,3)9-17/h12-13,15,17H,1-2,5-9H2,3-4H3/t12-,13?,15-,16-/m1/s1
InChIKey KTZVYIFKRSNKFH-GCBHHIMKSA-N
Formula C16H24O3
HBA 3
HBD 1
MW 264.36
Rotatable Bonds 2
TPSA 46.53
LogP 2.5
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 264.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria arabica Asteraceae Plantae 119185

Showing of synonyms

  • Hafez S, Sarg TM, et al. (1987). Caryophyllene derivatives from Pulicaria arabica. Phytochemistry,1987,26(12),3356-3358. [View]
Pubchem: 163031362

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC(=C)C(=O)CC(C12)CC2

Level: 0

Mol. Weight: 264.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.370
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.620
Plasma Protein Binding
48.11
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
11.660
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.270
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.140
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.490
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
-1.720
Rat (Acute)
2.410
Rat (Chronic Oral)
1.820
Fathead Minnow
3.920
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
343.850
Hydration Free Energy
-6.800
Log(D) at pH=7.4
1.730
Log(P)
2.23
Log S
-2.16
Log(Vapor Pressure)
-5.2
Melting Point
97.06
pKa Acid
10.22
pKa Basic
5.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9103
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9103
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8792
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8792
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8701
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8701
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8544
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8544
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8485
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8485
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7825
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7825
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7772
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7772
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7660
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7660
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7601
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7601
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7384
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7384
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7318
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7318
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7312
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7312
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7252
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7252
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7178
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7178
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7092
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7092
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7061
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7061
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7049
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7049

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