4beta,9alpha-dihydroxy-6alpha-(4-hydroxy-3-methoxybenzoyl)-dauc-7-ene - Compound Card

4beta,9alpha-dihydroxy-6alpha-(4-hydroxy-3-methoxybenzoyl)-dauc-7-ene

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4beta,9alpha-dihydroxy-6alpha-(4-hydroxy-3-methoxybenzoyl)-dauc-7-ene

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Daucane Sesquiterpenoid Ester
Canonical Smiles COc1cc(ccc1O)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/C23H32O6/c1-13(2)23(27)9-8-22(4)12-17(25)14(3)10-19(20(22)23)29-21(26)15-6-7-16(24)18(11-15)28-5/h6-7,10-11,13,17,19-20,24-25,27H,8-9,12H2,1-5H3/t17-,19-,20+,22+,23+/m0/s1
InChIKey YEYDMYXRNHSXFX-KZMGXOGOSA-N
Formula C23H32O6
HBA 6
HBD 3
MW 404.5
Rotatable Bonds 4
TPSA 96.22
LogP 3.44
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 404.22
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: 14466074

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 404.5 g/mol

Structure

SMILES: C1CCC(C12)CCC=CC2

Level: 0

Mol. Weight: 404.5 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 404.5 g/mol

Radical scavenging

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.710
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.710
Plasma Protein Binding
75.52
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
12.640
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.070
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.490
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.780
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-11.640
Rat (Acute)
2.770
Rat (Chronic Oral)
2.550
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
414.550
Hydration Free Energy
-6.200
Log(D) at pH=7.4
2.930
Log(P)
3.44
Log S
-4.13
Log(Vapor Pressure)
-7.72
Melting Point
171.34
pKa Acid
7.1
pKa Basic
4.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9231
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9231
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8750
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8750
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8557
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8557
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8339
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8339
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8292
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8292
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8036
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8036
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7842
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7842
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7639
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7639
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7567
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7567
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7553
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7553
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7439
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7439
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7363
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7363
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7326
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7326
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7311
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7311
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7226
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7226
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7221
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7221
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7197
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7197
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7094
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7094
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7086
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7086
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7084
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7084

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