4beta,9alpha-dihydroxy-6alpha-p-hydroxybenzoyldauc-7-ene - Compound Card

4beta,9alpha-dihydroxy-6alpha-p-hydroxybenzoyldauc-7-ene

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4beta,9alpha-dihydroxy-6alpha-p-hydroxybenzoyldauc-7-ene

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles Oc1ccc(cc1)C(=O)O[C@H]1C=C(C)[C@H](C[C@@]2([C@@H]1[C@@](O)(CC2)C(C)C)C)O
InChI InChI=1S/C22H30O5/c1-13(2)22(26)10-9-21(4)12-17(24)14(3)11-18(19(21)22)27-20(25)15-5-7-16(23)8-6-15/h5-8,11,13,17-19,23-24,26H,9-10,12H2,1-4H3/t17-,18-,19+,21+,22+/m0/s1
InChIKey JYELHVZHUTYKGP-JIWOIOHBSA-N
Formula C22H30O5
HBA 5
HBD 3
MW 374.48
Rotatable Bonds 3
TPSA 86.99
LogP 3.43
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 374.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula sinaica Apiaceae Plantae 1514050
2 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]
  • Ahmed AA (1999). Sesquiterpene coumarins and sesquiterpenes from Ferula sinaica. Phytochemistry,1999,50(1),109-112. [View]
Pubchem: 162877927
Nmrshiftdb2: 70031034

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 374.48 g/mol

Structure

SMILES: C1CCC(C12)CCC=CC2

Level: 0

Mol. Weight: 374.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 374.48 g/mol

Radical scavenging

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.630
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.670
Plasma Protein Binding
78.7
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
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
10.460
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.420
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.340
Micronucleos
Toxic
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
Toxic
T. Pyriformis
-4.820
Rat (Acute)
3.080
Rat (Chronic Oral)
2.480
Fathead Minnow
4.030
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
406.700
Hydration Free Energy
-7.770
Log(D) at pH=7.4
3.060
Log(P)
3.72
Log S
-4.2
Log(Vapor Pressure)
-7.77
Melting Point
181.73
pKa Acid
7.06
pKa Basic
4.58
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8435
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8435
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7746
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7746
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7454
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7454
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7348
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7348
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7154
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7154
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7061
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7061

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