2-desoxo-2,4-bis(acetyloxy)tomentosin - Compound Card

2-desoxo-2,4-bis(acetyloxy)tomentosin

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2-desoxo-2,4-bis(acetyloxy)tomentosin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)OC(C1=CC[C@H]2[C@@H](C[C@@H]1C)OC(=O)C2=C)CC(OC(=O)C)C
InChI InChI=1S/C19H26O6/c1-10-8-17-16(12(3)19(22)25-17)7-6-15(10)18(24-14(5)21)9-11(2)23-13(4)20/h6,10-11,16-18H,3,7-9H2,1-2,4-5H3/t10-,11?,16+,17+,18?/m0/s1
InChIKey KFJJTDVDBCPZBQ-XNHRUCMSSA-N
Formula C19H26O6
HBA 6
HBD 0
MW 350.41
Rotatable Bonds 5
TPSA 78.9
LogP 2.71
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.63
Exact Mass 350.17
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: 162816925

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 350.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
48.59
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
11.72
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.51
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.54
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.7
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
-0.49
Rat (Acute)
2.58
Rat (Chronic Oral)
1.88
Fathead Minnow
4.19
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
355.41
Hydration Free Energy
-4.96
Log(D) at pH=7.4
2.21
Log(P)
1.93
Log S
-3.81
Log(Vapor Pressure)
-6.14
Melting Point
52.55
pKa Acid
10.96
pKa Basic
5.73
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 0.8988
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8988
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8743
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8743
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8655
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8655
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8582
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8582
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8483
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8483
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8151
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8151
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8111
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8111
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8085
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8085
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8037
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8037
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7956
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7956
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7902
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7902
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7819
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7819
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7752
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7752
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7718
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7718
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7680
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7680
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7553
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7553
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7546
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7546
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7507
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7507
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7467
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7467
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7394
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7394
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7361
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7361
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7324
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7324
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7202
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7202
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7171
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7171
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7136
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7136
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7114
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7114
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7063
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7063
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7032
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7032
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7018
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7018
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7016
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7016
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7013
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7013
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7003
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7003

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