8-epi-isoxanthanol - Compound Card

8-epi-isoxanthanol

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8-epi-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-WQIYYFHDSA-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: 56969896
Nmrshiftdb2: 70093930

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 308.37 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.74
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
-2.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
44.07
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.04
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
4.69
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
-3.45
Rat (Acute)
3.17
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
347.79
Hydration Free Energy
-6.98
Log(D) at pH=7.4
1.5
Log(P)
1.62
Log S
-2.94
Log(Vapor Pressure)
-6.15
Melting Point
80.53
pKa Acid
10.24
pKa Basic
5.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9302
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9302
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9244
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9244
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9173
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9173
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9101
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9101
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9072
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9072
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8984
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8984
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8927
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8927
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8892
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8892
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8543
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8543
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8524
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8524
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8477
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8477
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8262
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8262
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8200
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8200
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8179
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8179
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.8163
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.8163
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8092
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8092
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8055
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8055
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7965
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7965
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7961
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7961
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7954
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7954
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7900
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7900
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7799
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7799
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7738
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7738
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7717
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7717
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7674
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7674
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7652
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7652
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7621
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7621
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7603
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7603
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7593
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7593
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7583
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7583
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7578
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7578
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7547
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7547
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7527
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7527
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7522
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7522
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7513
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7513
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7507
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7507
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7497
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7497
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7492
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7492
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7472
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7472
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7418
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7418
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7398
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7398
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7392
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7392
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7376
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7376
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7266
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7266
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7252
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7252
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7250
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7250
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7228
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7228
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7212
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7212
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7210
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7210
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7183
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7183
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7168
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7168
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7153
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7153
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7123
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7123
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7122
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7122
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7116
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7116
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7100
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7100
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7095
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7095
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7063
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7063

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