Isoxanthanol - Compound Card

Isoxanthanol

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Isoxanthanol

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C[C@@H](C[C@@H](C1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)C2=C)O)OC(=O)C
InChI InChI=1S/C17H24O5/c1-9-7-16-14(11(3)17(20)22-16)6-5-13(9)15(19)8-10(2)21-12(4)18/h5,9-10,14-16,19H,3,6-8H2,1-2,4H3/t9-,10-,14+,15-,16-/m0/s1
InChIKey IQAWVYINTAIBSH-KVRZASPWSA-N
Formula C17H24O5
HBA 5
HBD 1
MW 308.37
Rotatable Bonds 4
TPSA 72.83
LogP 2.14
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 308.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria undulata Asteraceae Plantae 119186

Showing of synonyms

  • Hegazy MEF, Matsuda H, et al. (2012). Sesquiterpenes from an Egyptian herbal medicine, Pulicaria undulate, with inhibitory effects on nitric oxide production in RAW264.7 macrophage cells. Chemical and Pharmaceutical Bulletin,2012,60(3),363-370. [View] [PubMed]
Pubchem: 162867363
Nmrshiftdb2: 60061397
CPRiL: 410737
Structure

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

Level: 0

Mol. Weight: 308.37 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.76
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
-2.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
44.25
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
10.17
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.02
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.49
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.71
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
-3.18
Rat (Acute)
3.18
Rat (Chronic Oral)
1.82
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
347.09
Hydration Free Energy
-6.94
Log(D) at pH=7.4
1.48
Log(P)
1.68
Log S
-2.94
Log(Vapor Pressure)
-6.17
Melting Point
83.12
pKa Acid
10.29
pKa Basic
5.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9330
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9330
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9246
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9246
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9091
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9091
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9034
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9034
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8883
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8883
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8630
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8630
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8618
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8618
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8618
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8618
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8616
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8616
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8500
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8500
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8413
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8413
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8410
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8410
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8344
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8344
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8330
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8330
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8232
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8232
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8165
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8165
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8141
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8141
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7960
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7960
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7933
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7933
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7859
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7859
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7799
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7799
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7778
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7778
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7702
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7702
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7671
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7671
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7627
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7627
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7586
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7586
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 4 0.7560
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 4 0.7560
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7427
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7427
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7370
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7370
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7313
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7313
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7213
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7213
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7206
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7206
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7170
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7170
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7158
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7158
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7135
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7135
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7084
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7084
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7081
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7081
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7079
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7079
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7049
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7049
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7045
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7045
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7036
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7036

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