4beta,9alpha-dihydroxy-6alphabenzoyl-dauc-7-ene - Compound Card

4beta,9alpha-dihydroxy-6alphabenzoyl-dauc-7-ene

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4beta,9alpha-dihydroxy-6alphabenzoyl-dauc-7-ene

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Daucane Sesquiterpenoid Ester
Canonical Smiles O[C@H]1C[C@@]2(C)CC[C@@]([C@@H]2[C@H](C=C1C)OC(=O)c1ccccc1)(O)C(C)C
InChI InChI=1S/C22H30O4/c1-14(2)22(25)11-10-21(4)13-17(23)15(3)12-18(19(21)22)26-20(24)16-8-6-5-7-9-16/h5-9,12,14,17-19,23,25H,10-11,13H2,1-4H3/t17-,18-,19+,21+,22+/m0/s1
InChIKey XUBRQXOGVTUWAS-JIWOIOHBSA-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: 163054506

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2C=CCCC(C23)CCC3

Level: 1

Mol. Weight: 358.48 g/mol

Structure

SMILES: C1CCC(C12)CCC=CC2

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)
-4.56
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
83.81
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.36
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.56
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.35
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.52
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
-3.92
Rat (Acute)
3.75
Rat (Chronic Oral)
2.36
Fathead Minnow
4.01
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
381.26
Hydration Free Energy
-7.26
Log(D) at pH=7.4
3.03
Log(P)
4.21
Log S
-4.48
Log(Vapor Pressure)
-7.03
Melting Point
148.44
pKa Acid
7.81
pKa Basic
4.5
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8168
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8168
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7559
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7559
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7375
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7375
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7281
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7281
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7210
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7210
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7153
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7153
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7107
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7107

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