10-oxo-jaesckeanadiol-6-anisate - Compound Card

10-oxo-jaesckeanadiol-6-anisate

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10-oxo-jaesckeanadiol-6-anisate

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpenoid
Canonical Smiles COc1ccc(cc1)C(=O)O[C@H]1CCC(=CC(=O)[C@@]2([C@@H]1[C@@](O)(CC2)C(C)C)C)C
InChI InChI=1S/C24H32O5/c1-15(2)24(27)13-12-23(4)20(25)14-16(3)6-11-19(21(23)24)29-22(26)17-7-9-18(28-5)10-8-17/h7-10,14-15,19,21,27H,6,11-13H2,1-5H3/t19-,21+,23+,24+/m0/s1
InChIKey BQXSOAYEWFDUTC-IVGWJTKZSA-N
Formula C24H32O5
HBA 5
HBD 1
MW 400.52
Rotatable Bonds 4
TPSA 72.83
LogP 4.33
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 400.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula vesceritensis Apiaceae Plantae 1514058

Showing of synonyms

  • Oughlissi-Dehak K, Lawton P, et al. (2008). Sesquiterpenes from aerial parts of Ferula vesceritensis. Phytochemistry,2008,69(9),1933-1938. [View] [PubMed]
Pubchem: 162870632

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(C(C23)CCC2)CCC=CC3=O

Level: 1

Mol. Weight: 400.52 g/mol

Structure

SMILES: C1CCC(C12)CCCC=CC2=O

Level: 0

Mol. Weight: 400.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 400.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.540
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.560
Plasma Protein Binding
89.1
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.460
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.430
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.120
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.850
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
Toxic
T. Pyriformis
-12.900
Rat (Acute)
3.300
Rat (Chronic Oral)
1.840
Fathead Minnow
3.990
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
411.540
Hydration Free Energy
-4.700
Log(D) at pH=7.4
3.840
Log(P)
4.68
Log S
-4.73
Log(Vapor Pressure)
-6.95
Melting Point
148.52
pKa Acid
8.74
pKa Basic
3.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9180
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9180
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7915
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7915
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7610
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7610
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7550
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7550
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7542
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7542
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7450
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7450
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7441
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7441
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7429
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7429
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7398
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7398
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7394
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7394
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7383
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7383
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7330
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7330
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7319
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7319
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7307
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7307
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7296
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7296
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7230
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7230
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7205
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7205
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7188
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7188
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7089
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7089
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7065
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7065
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7042
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7042
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7010
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7010
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7000
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7000

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