10-angeloyloxy-6-p-methoxybenzoyl-jaeschkeanadiol - Compound Card

10-angeloyloxy-6-p-methoxybenzoyl-jaeschkeanadiol

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10-angeloyloxy-6-p-methoxybenzoyl-jaeschkeanadiol

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles COc1ccc(cc1)C(=O)O[C@H]1CC(=C[C@H]([C@@]2([C@@H]1[C@@](O)(CC2)C(C)C)C)OC(=O)/C(=C\C)/C)C
InChI InChI=1S/C28H38O6/c1-8-19(5)25(29)34-23-16-18(4)15-22(24-27(23,6)13-14-28(24,31)17(2)3)33-26(30)20-9-11-21(32-7)12-10-20/h8-12,16-17,22-24,31H,13-15H2,1-7H3/b19-8-/t22-,23+,24+,27+,28+/m0/s1
InChIKey FREVCFKUUWCACL-SHDLGAEZSA-N
Formula C28H38O6
HBA 6
HBD 1
MW 470.61
Rotatable Bonds 6
TPSA 82.06
LogP 5.25
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 470.27
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula communis var. brevifolia Apiaceae Plantae 52470
2 Ferula vesceritensis Apiaceae Plantae 1514058

Showing of synonyms

  • Lamnaouer D, Martin MT, et al. (1989). Isolation of daucane esters from Ferula communis var. Brevifolia. Phytochemistry,1989,28(10),2711-2716. [View]
  • Zellagui A, Gherraf N, et al. (2012). Phytochemical investigation and antimicrobial activity of crude extract of the roots of Ferula vesceritensis. Chemistry of Natural Compounds,2012,48(5),891-892. [View]
Pubchem: 162900718
Nmrshiftdb2: 60057525

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2CC=CCC(C23)CCC3

Level: 1

Mol. Weight: 470.61 g/mol

Structure

SMILES: C1CCC(C12)CCC=CC2

Level: 0

Mol. Weight: 470.61 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 470.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.48
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.630
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.770
Plasma Protein Binding
95.28
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
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.040
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.630
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.240
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.910
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
-129.900
Rat (Acute)
3.200
Rat (Chronic Oral)
2.170
Fathead Minnow
4.390
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
427.880
Hydration Free Energy
-2.690
Log(D) at pH=7.4
4.780
Log(P)
6.4
Log S
-5.68
Log(Vapor Pressure)
-7.73
Melting Point
141.12
pKa Acid
9.55
pKa Basic
4.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7612
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7612
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7431
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7431
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7361
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7361
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7350
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7350
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7349
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7349
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7319
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7319
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7295
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7295
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7243
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7243
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7228
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7228
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7196
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7196
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7035
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7035
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7030
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7030
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7014
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7014

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