8alpha-hydroxy-3beta-(benzoyloxy)-1alphaH,5alphaH,6betaH,7alphaH-guai-4(15),10(14),11(13)-trien-6,12-olide - Compound Card

8alpha-hydroxy-3beta-(benzoyloxy)-1alphaH,5alphaH,6betaH,7alphaH-guai-4(15),10(14),11(13)-trien-6,12-olide

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8alpha-hydroxy-3beta-(benzoyloxy)-1alphaH,5alphaH,6betaH,7alphaH-guai-4(15),10(14),11(13)-trien-6,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C=C1C[C@H](O)[C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)OC(=O)c1ccccc1)OC(=O)C2=C
InChI InChI=1S/C22H22O5/c1-11-9-16(23)19-13(3)21(24)27-20(19)18-12(2)17(10-15(11)18)26-22(25)14-7-5-4-6-8-14/h4-8,15-20,23H,1-3,9-10H2/t15-,16-,17-,18-,19+,20+/m0/s1
InChIKey UIIZHPJVPKARSE-GFLQDLJJSA-N
Formula C22H22O5
HBA 5
HBD 1
MW 366.41
Rotatable Bonds 2
TPSA 72.83
LogP 2.82
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 366.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea scoparia Asteraceae Plantae 2072395

Showing of synonyms

  • Youssef DTA (1998). Sesquiterpene lactones from Centaurea scoparia. Phytochemistry,1998,49(6),1733-1737. [View] [PubMed]
Pubchem: 100927643
Nmrshiftdb2: 60072799

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(C2=C)CC3C(=C)CCC(C(=C)C(=O)O4)C4C23

Level: 1

Mol. Weight: 366.41 g/mol

Structure

SMILES: O=C(O1)C(=C)C(C1C23)CCC(=C)C3CCC2=C

Level: 0

Mol. Weight: 366.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 366.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.76
Plasma Protein Binding
79.53
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
Non-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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.34
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.66
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.18
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
-7.73
Rat (Acute)
3.98
Rat (Chronic Oral)
2.36
Fathead Minnow
3.99
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
408.0
Hydration Free Energy
-5.51
Log(D) at pH=7.4
2.98
Log(P)
3.47
Log S
-4.44
Log(Vapor Pressure)
-8.22
Melting Point
156.46
pKa Acid
7.66
pKa Basic
3.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9287
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9287
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9227
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9227
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9208
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9208
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9041
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9041
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9028
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9028
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8950
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8950
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8536
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8536
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8325
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8325
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8311
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8311
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8208
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8208
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.8160
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.8160
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7993
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7993
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7928
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7928
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7911
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7911
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7909
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7909
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7837
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7837
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7806
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7806
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7787
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7787
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7575
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7575
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7524
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7524
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7471
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7471
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7419
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7419
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7390
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7390
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7255
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7255
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7217
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7217
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7136
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7136
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7119
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7119
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7113
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7113
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7105
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7105
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7099
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7099
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7056
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7056
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7000
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7000

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