Antheindurolide A - Compound Card

Antheindurolide A

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Antheindurolide A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C(=C\CC1COC(=O)C1=C)/CC1CC(C(=O)O1)C
InChI InChI=1S/C15H20O4/c1-9(6-13-7-10(2)14(16)19-13)4-5-12-8-18-15(17)11(12)3/h4,10,12-13H,3,5-8H2,1-2H3/b9-4+
InChIKey KFKSQOIZZRZEFC-RUDMXATFSA-N
Formula C15H20O4
HBA 4
HBD 0
MW 264.32
Rotatable Bonds 4
TPSA 52.6
LogP 2.39
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Anthemis tigrensis Asteraceae Plantae 158234

Showing of synonyms

  • Sorsa A, Asfaw N. (2007). Phytochemical investigation on the aerial part of Anthemis tigreensis (chloroform extract). M.Sc. Thesis-3, Addis Ababa University, Ethiopia, 2007. [View] [PubMed]
Pubchem: 14733727
Nmrshiftdb2: 60080055

No compound-protein relationship available.

Structure

SMILES: O=C1CCC(O1)CC=CCC2COC(=O)C2=C

Level: 1

Mol. Weight: 264.32 g/mol

Structure

SMILES: C=C1C(=O)OCC1

Level: 0

Mol. Weight: 264.32 g/mol

Structure

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.08
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.93
Plasma Protein Binding
27.71
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.91
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.29
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.65
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.18
Rat (Acute)
2.6
Rat (Chronic Oral)
1.83
Fathead Minnow
4.68
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
347.28
Hydration Free Energy
-3.97
Log(D) at pH=7.4
1.55
Log(P)
1.51
Log S
-3.66
Log(Vapor Pressure)
-5.69
Melting Point
51.52
pKa Acid
8.23
pKa Basic
5.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9198
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9198
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9128
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9128
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8894
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8894
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8672
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8672
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8400
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8400
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8285
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8285
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8253
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8253
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8221
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8221
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7944
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7944
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7816
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7816
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7765
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7765
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7710
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7710
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7671
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7671
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7665
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7665
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7616
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7616
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7570
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7570
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7547
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7547
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7543
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7543
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7518
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7518
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7513
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7513
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7479
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7479
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7445
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7445
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7415
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7415
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7368
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7368
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7352
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7352
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7335
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7335
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7296
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7296
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7288
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7288
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7256
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7256
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7245
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7245
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7218
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7218
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7158
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7158
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7155
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7155
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7154
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7154
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7107
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7107
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7103
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7103
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7080
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7080
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7070
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7070
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7063
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7063
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7059
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7059
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7038
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7038
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7006
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7006

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