2-desoxo-2-acetyloxy-4-hydroxy-tomentosin - Compound Card

2-desoxo-2-acetyloxy-4-hydroxy-tomentosin

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2-desoxo-2-acetyloxy-4-hydroxy-tomentosin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(CC(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-POVWYJMBSA-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 Francoeuria crispa Asteraceae Plantae 1548540

Showing of synonyms

  • Abdel-Mogib M, Jakupovic J, et al. (1990). Sesquiterpene lactones and kaurane glycosides from Francoeuria crispa. Phytochemistry,1990,29(8),2581-2584. [View]
Pubchem: 162867362

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 308.37 g/mol

No bioactivities available.

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
-2.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
40.42
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
10.17
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.14
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
Safe
Daphnia Maga
4.74
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
0.71
Rat (Acute)
3.2
Rat (Chronic Oral)
1.82
Fathead Minnow
3.95
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
344.33
Hydration Free Energy
-6.98
Log(D) at pH=7.4
1.6
Log(P)
1.43
Log S
-2.84
Log(Vapor Pressure)
-6.04
Melting Point
71.55
pKa Acid
10.23
pKa Basic
5.55
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 0.8876
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8876
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8749
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8749
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8683
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8683
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8680
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8680
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8437
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8437
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8432
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8432
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8376
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8376
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8274
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8274
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8205
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8205
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.8195
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.8195
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8194
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8194
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8183
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8183
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8175
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8175
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8162
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8162
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8079
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8079
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.8067
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.8067
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8033
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8033
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7809
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7809
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7773
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7773
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7709
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7709
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7639
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7639
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7547
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7547
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7537
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7537
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7494
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7494
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7454
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7454
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7413
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7413
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7381
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7381
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7370
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7370
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7363
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7363
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7318
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7318
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7298
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7298
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7290
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7290
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7274
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7274
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7235
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7235
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7179
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7179
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7179
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7179
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7159
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7159
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7119
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7119
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7117
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7117
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7114
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7114
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7109
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7109
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7075
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7075
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7073
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7073
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7069
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7069
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7068
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7068
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7048
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7048
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7026
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7026
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7008
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7008
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7007
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7007

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