8beta-(2-methylbutyryloxy)-11,13-dihydroartecanin - Compound Card

8beta-(2-methylbutyryloxy)-11,13-dihydroartecanin

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8beta-(2-methylbutyryloxy)-11,13-dihydroartecanin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OOC(C(=C)CC(=O)C=C(C)C)CCC(C=C)(O)C
InChI InChI=1S/C15H24O4/c1-6-15(5,17)8-7-14(19-18)12(4)10-13(16)9-11(2)3/h6,9,14,17-18H,1,4,7-8,10H2,2-3,5H3
InChIKey WIRFHQRSPGKCFP-UHFFFAOYSA-N
Formula C15H24O4
HBA 4
HBD 2
MW 268.35
Rotatable Bonds 9
TPSA 66.76
LogP 3.04
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 268.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Otanthus maritimus Asteraceae Plantae 1155244
2 Pentzia albida Asteraceae Plantae 1721051

Showing of synonyms

  • Jakupovic J, Boeker R, et al. (1988). Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry,1988,27(4),1135-1140. [View]
  • Sabri NN, El-Salam NAA, et al. (1983). Sesquiterpene lactones of Otanthus maritimus. Phytochemistry,1983,22(1),201-202. [View]
Pubchem: 14021431

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.180
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.110
Plasma Protein Binding
15.08
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.520
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.630
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.500
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.640
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
3.040
Rat (Acute)
2.110
Rat (Chronic Oral)
1.870
Fathead Minnow
4.170
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
289.900
Hydration Free Energy
-12.240
Log(D) at pH=7.4
0.860
Log(P)
1.78
Log S
-2.05
Log(Vapor Pressure)
-5.28
Melting Point
66.44
pKa Acid
8.24
pKa Basic
3.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9339
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9339
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9212
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9212
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9088
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9088
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8851
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8851
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8787
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8787
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8663
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8663
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8622
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8622
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8548
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8548
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8392
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8392
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8389
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8389
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8228
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8228
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8116
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8116
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8022
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8022
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7839
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7839
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7829
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7829
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7827
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7827
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7746
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7746
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7733
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7733
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7718
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7718
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7717
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7717
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7664
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7664
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7637
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7637
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7572
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7572
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7486
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7486
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7398
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7398
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7396
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7396
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7392
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7392
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7377
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7377
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7347
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7347
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7320
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7320
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7300
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7300
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7256
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7256
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7219
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7219
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7194
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7194
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7178
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7178
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7168
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7168
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7124
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7124
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7101
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7101
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7099
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7099
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7066
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7066
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7040
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7040
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7021
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7021
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7018
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7018
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7007
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7007

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