5beta,12-dihydroxy-5,6-dihydrocaryophyllen-7-one - Compound Card

5beta,12-dihydroxy-5,6-dihydrocaryophyllen-7-one

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5beta,12-dihydroxy-5,6-dihydrocaryophyllen-7-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC[C@@]1(C)C[C@H]2C1CC(=O)C(=C)[C@@H](CCC2=C)O
InChI InChI=1S/C15H22O3/c1-9-4-5-13(17)10(2)14(18)6-12-11(9)7-15(12,3)8-16/h11-13,16-17H,1-2,4-8H2,3H3/t11-,12?,13-,15-/m1/s1
InChIKey JOPKITGVIQRWBI-HTYKBFHYSA-N
Formula C15H22O3
HBA 3
HBD 2
MW 250.34
Rotatable Bonds 1
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 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: 162929008

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 250.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.25
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)
0.57
Plasma Protein Binding
47.07
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-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
9.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.34
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.92
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
-1.96
Rat (Acute)
2.78
Rat (Chronic Oral)
1.86
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
348.22
Hydration Free Energy
-9.43
Log(D) at pH=7.4
0.99
Log(P)
1.61
Log S
-1.75
Log(Vapor Pressure)
-6.14
Melting Point
123.3
pKa Acid
9.31
pKa Basic
5.65
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 0.8672
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8672
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8550
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8550
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.8447
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.8447
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8350
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8350
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8215
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8215
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8172
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8172
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8100
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8100
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.8019
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.8019
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7760
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7760
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7647
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7647
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7641
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7641
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7541
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7541
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7416
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7416
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7385
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7385
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7259
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7259
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7208
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7208
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7204
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7204
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7189
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7189
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7165
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7165
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7116
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7116
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7089
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7089
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7072
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7072
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7025
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7025
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7009
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7009

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