3beta,13-diacetoxy-1beta,13-dihydroxyeudesma-4(14),7(11)-dien-6alpha,12-olide - Compound Card

3beta,13-diacetoxy-1beta,13-dihydroxyeudesma-4(14),7(11)-dien-6alpha,12-olide

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3beta,13-diacetoxy-1beta,13-dihydroxyeudesma-4(14),7(11)-dien-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)OCC1=C2CCC3[C@@H]([C@H]2OC1=O)C(=C)[C@H](C[C@H]3O)OC(=O)C
InChI InChI=1S/C18H22O7/c1-8-15(24-10(3)20)6-14(21)12-5-4-11-13(7-23-9(2)19)18(22)25-17(11)16(8)12/h12,14-17,21H,1,4-7H2,2-3H3/t12?,14-,15+,16+,17+/m1/s1
InChIKey PGITZFFJBXEEET-ITGMQTRRSA-N
Formula C18H22O7
HBA 7
HBD 1
MW 350.37
Rotatable Bonds 3
TPSA 99.13
LogP 1.05
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 350.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Achillea fragrantissima Asteraceae Plantae 282738

Showing of synonyms

  • Abdel-Mogib M, Jakupovic J, et al. (1989). Glaucolides from Achillea fragrantissima.. Phytochemistry,1989,28(12),3528-3530. [View]
Pubchem: 162817326
Nmrshiftdb2: 70069998

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC(CC2)C1C(C2=3)OC(=O)C3

Level: 0

Mol. Weight: 350.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.37
Plasma Protein Binding
38.38
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
9.6
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.35
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.09
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.65
Micronucleos
Toxic
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
-3.44
Rat (Acute)
3.41
Rat (Chronic Oral)
2.06
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
369.42
Hydration Free Energy
-7.81
Log(D) at pH=7.4
0.76
Log(P)
1.35
Log S
-2.72
Log(Vapor Pressure)
-7.22
Melting Point
143.22
pKa Acid
8.46
pKa Basic
4.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8827
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8827
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8703
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8703
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8647
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8647
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8295
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8295
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8254
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8254
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8198
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8198
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8015
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8015
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7949
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7949
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7889
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7889
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7889
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7889
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7842
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7842
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7805
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7805
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7792
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7792
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7778
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7778
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7771
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7771
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7744
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7744
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7705
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7705
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7642
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7642
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7610
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7610
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7582
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7582
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7572
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7572
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7527
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7527
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7493
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7493
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7412
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7412
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7378
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7378
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7377
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7377
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7357
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7357
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7338
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7338
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7155
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7155
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7035
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7035
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7029
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7029

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