1alpha,5alpha-epoxy-1,5-dihydroxanthatin - Compound Card

1alpha,5alpha-epoxy-1,5-dihydroxanthatin

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1alpha,5alpha-epoxy-1,5-dihydroxanthatin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(CC(=O)C1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)C2=C)OC(=O)C
InChI InChI=1S/C17H22O5/c1-9-7-16-14(11(3)17(20)22-16)6-5-13(9)15(19)8-10(2)21-12(4)18/h5,9-10,14,16H,3,6-8H2,1-2,4H3/t9-,10?,14+,16-/m0/s1
InChIKey IIIVMAIJSDOODP-HONMUUDHSA-N
Formula C17H22O5
HBA 5
HBD 0
MW 306.36
Rotatable Bonds 4
TPSA 69.67
LogP 2.35
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 306.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Xanthium spinosum Asteraceae Plantae 1053410
2 Xanthium spinosum Asteraceae Plantae 1053410

Showing of synonyms

  • Abdei-Mogib M, Dawidar AM, et al. (1991). Xanthanolides from Xanthium spinosum. Phytochemistry,1991,30(10),3461-3462. [View]
  • Omar AA, Elrashidy EM, et al. (1984). Xanthanolides from Xanthium spinosum. Phytochemistry,1984,23(4),915-916. [View]
Pubchem: 15699898

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CCC=CC2

Level: 0

Mol. Weight: 306.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.63
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
54.62
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
10.33
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.01
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.56
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.08
Micronucleos
Toxic
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
1.36
Rat (Acute)
2.82
Rat (Chronic Oral)
1.97
Fathead Minnow
4.06
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
341.56
Hydration Free Energy
-5.73
Log(D) at pH=7.4
1.71
Log(P)
1.97
Log S
-3.07
Log(Vapor Pressure)
-5.63
Melting Point
70.96
pKa Acid
10.39
pKa Basic
4.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9468
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9468
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9334
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9334
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9174
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9174
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 4 0.9149
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 4 0.9149
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9108
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9108
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9062
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9062
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9054
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9054
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8964
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8964
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8899
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8899
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8883
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8883
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8800
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8800
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8774
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8774
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8659
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8659
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8586
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8586
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8570
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8570
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8482
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8482
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8414
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8414
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8391
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8391
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8367
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8367
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8355
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8355
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.8345
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.8345
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8273
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8273
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8079
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8079
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8072
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8072
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7995
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7995
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7993
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7993
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7829
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7829
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7772
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7772
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7770
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7770
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7766
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7766
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7743
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7743
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7735
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7735
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7717
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7717
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7705
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7705
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7694
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7694
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7555
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7555
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7534
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7534
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7508
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7508
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7501
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7501
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7493
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7493
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7473
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7473
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7460
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7460
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7436
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7436
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7416
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7416
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7398
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7398
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7387
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7387
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7382
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7382
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7380
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7380
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7363
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7363
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7325
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7325
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7310
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7310
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7309
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7309
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
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7159
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7159
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7123
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7123
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7116
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7116
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7060
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7060
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7054
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7054
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7032
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7032
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7012
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7012

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