4beta-hydroxy-6alpha-benzoyl-7-daucen-9-one - Compound Card

4beta-hydroxy-6alpha-benzoyl-7-daucen-9-one

Select a section from the left sidebar

4beta-hydroxy-6alpha-benzoyl-7-daucen-9-one

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Daucane Sesquiterpenoid Ester
Canonical Smiles O=C(c1ccccc1)O[C@H]1C[C@@](C)(O)C=C[C@@]2([C@@H]1[C@@](O)(CC2)C(C)C)C
InChI InChI=1S/C22H30O4/c1-15(2)22(25)13-11-20(3)10-12-21(4,24)14-17(18(20)22)26-19(23)16-8-6-5-7-9-16/h5-10,12,15,17-18,24-25H,11,13-14H2,1-4H3/t17-,18+,20-,21-,22+/m0/s1
InChIKey RLHMEXGBDMGLGZ-XRYRHKQGSA-N
Formula C22H30O4
HBA 4
HBD 2
MW 358.48
Rotatable Bonds 3
TPSA 66.76
LogP 3.73
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 358.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula hermonis Apiaceae Plantae 662815

Showing of synonyms

  • Ibraheim ZZ, Abdel-Mageed WM, et al. (2012). Antimicrobial antioxidant daucane sesquiterpenes from Ferula hermonis Boiss. Phytotherapy Research,2012,26,579-586. [View] [PubMed]
Pubchem: 162869740

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CCC=C3

Level: 1

Mol. Weight: 358.48 g/mol

Structure

SMILES: C1CCC(C12)CCCC=C2

Level: 0

Mol. Weight: 358.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 358.48 g/mol

Radical scavenging

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.41
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.6
Plasma Protein Binding
81.46
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.86
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.23
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.84
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-4.76
Rat (Acute)
3.18
Rat (Chronic Oral)
2.07
Fathead Minnow
3.97
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
372.28
Hydration Free Energy
-6.89
Log(D) at pH=7.4
3.27
Log(P)
4.09
Log S
-4.62
Log(Vapor Pressure)
-6.67
Melting Point
151.68
pKa Acid
7.9
pKa Basic
5.37
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7339
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7339
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7203
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7203

Download SDF