3-deacetyl-11,13-dihydro-10,14-deoxyarctolide - Compound Card

3-deacetyl-11,13-dihydro-10,14-deoxyarctolide

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3-deacetyl-11,13-dihydro-10,14-deoxyarctolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C=C1C(O)CC2[C@@H]([C@@H]3[C@H]1CC(C3=C)O)OC(=O)[C@H]2C
InChI InChI=1S/C15H20O4/c1-6-9-4-12(17)8(3)13(9)14-10(5-11(6)16)7(2)15(18)19-14/h7,9-14,16-17H,1,3-5H2,2H3/t7-,9-,10?,11?,12?,13-,14-/m0/s1
InChIKey GLMKTMOFCGDFFQ-LAEOIKMWSA-N
Formula C15H20O4
HBA 4
HBD 2
MW 264.32
Rotatable Bonds 0
TPSA 66.76
LogP 1.04
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Venidium fastuosum Asteraceae Plantae 259861

Showing of synonyms

  • Ali AA, El-Emary NA, et al. (1992). Guaianolides from Venidium fastuosum. Phytochemistry,1992,31(8),2781-2784. [View]
Pubchem: 163053546

No compound-protein relationship available.

Structure

SMILES: C=C1CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.33
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
37.72
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
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
10.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.2
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.95
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.02
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
-0.57
Rat (Acute)
3.55
Rat (Chronic Oral)
1.99
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
350.65
Hydration Free Energy
-8.52
Log(D) at pH=7.4
-0.01
Log(P)
-0.01
Log S
-1.75
Log(Vapor Pressure)
-6.72
Melting Point
154.31
pKa Acid
7.06
pKa Basic
4.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9324
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9324
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9080
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9080
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9021
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9021
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8856
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8856
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8513
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8513
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8473
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8473
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8357
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8357
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8313
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8313
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8183
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8183
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8182
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8182
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7919
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7919
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7825
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7825
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7813
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7813
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7508
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7508
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7481
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7481
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7458
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7458
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7454
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7454
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7452
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7452
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7448
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7448
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7388
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7388
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7385
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7385
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7254
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7254
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7229
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7229
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7216
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7216
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7206
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7206
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7093
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7093
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7092
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7092

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