2-desoxo-2-hydroxy-8-epi-tomentosin - Compound Card

2-desoxo-2-hydroxy-8-epi-tomentosin

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2-desoxo-2-hydroxy-8-epi-tomentosin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(CCC1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)C2=C)O
InChI InChI=1S/C15H22O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h6,9-10,13-14,16H,3-5,7-8H2,1-2H3/t9-,10?,13+,14-/m0/s1
InChIKey KQEADOUDJYBGFC-GQIGNIDQSA-N
Formula C15H22O3
HBA 3
HBD 1
MW 250.34
Rotatable Bonds 3
TPSA 46.53
LogP 2.6
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 250.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Francoeuria crispa Asteraceae Plantae 1548540
2 Pulicaria undulata Asteraceae Plantae 119186

Showing of synonyms

  • Hegazy MEF, Nakamura S, et al. (2015). Rare hydroperoxyl guaianolide sesquiterpenes from Pulicaria undulata. Phytochemistry Letters,2015,12,177-181. [View]
  • Abdel-Mogib M, Jakupovic J, et al. (1990). Sesquiterpene lactones and kaurane glycosides from Francoeuria crispa. Phytochemistry,1990,29(8),2581-2584. [View]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 250.34 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.26
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
46.43
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.49
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.44
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.51
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.38
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
1.5
Rat (Acute)
2.21
Rat (Chronic Oral)
1.92
Fathead Minnow
3.92
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
327.21
Hydration Free Energy
-5.56
Log(D) at pH=7.4
1.98
Log(P)
2.05
Log S
-3.18
Log(Vapor Pressure)
-4.74
Melting Point
72.46
pKa Acid
10.29
pKa Basic
6.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9530
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9530
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9509
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9509
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9486
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9486
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9468
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9468
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9282
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9282
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9193
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9193
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9080
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9080
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8769
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8769
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8742
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8742
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8737
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8737
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8729
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8729
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8514
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8514
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8280
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8280
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8270
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8270
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8070
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8070
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8030
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8030
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8003
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8003
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7947
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7947
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7923
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7923
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7842
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7842
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7814
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7814
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7805
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7805
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7805
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7805
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7798
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7798
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7775
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7775
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7725
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7725
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7700
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7700
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7699
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7699
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7689
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7689
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7671
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7671
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7652
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7652
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7618
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7618
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7615
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7615
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7602
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7602
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7602
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7602
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7591
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7591
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7543
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7543
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7538
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7538
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7535
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7535
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7523
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7523
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7519
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7519
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7499
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7499
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7487
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7487
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7468
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7468
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7446
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7446
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7420
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7420
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7420
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7420
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7418
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7418
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7416
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7416
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7413
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7413
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7385
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7385
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7355
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7355
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7349
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7349
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7333
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7333
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7327
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7327
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7313
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7313
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7306
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7306
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7286
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7286
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7278
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7278
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7190
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7190
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7136
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7136
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7135
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7135
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7133
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7133
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7133
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7133
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7114
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7114
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7088
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7088
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7080
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7080
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7079
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7079
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7054
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7054
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7048
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7048
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7026
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7026
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7024
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7024
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7005
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7005
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7003
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7003

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