1-[(3aR,7S,8aS)-7-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-6-yl]-3-hydroxybutyl acetate - Compound Card

1-[(3aR,7S,8aS)-7-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-6-yl]-3-hydroxybutyl acetate

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1-[(3aR,7S,8aS)-7-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-6-yl]-3-hydroxybutyl acetate

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)OC(=O)C)O
InChI InChI=1S/C17H24O5/c1-9-7-15-14(11(3)17(20)22-15)6-5-13(9)16(8-10(2)18)21-12(4)19/h5,9-10,14-16,18H,3,6-8H2,1-2,4H3/t9-,10?,14+,15-,16?/m0/s1
InChIKey JKIKMDJRHDXNEW-UDDXETKPSA-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 Xanthium spinosum Asteraceae Plantae 1053410

Showing of synonyms

  • Abdei-Mogib M, Dawidar AM, et al. (1991). Xanthanolides from Xanthium spinosum. Phytochemistry,1991,30(10),3461-3462. [View]
Pubchem: 13071921
Nmrshiftdb2: 60063643
Bindingdb: 233117

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)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
40.87
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
9.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.25
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.14
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.96
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
0.78
Rat (Acute)
2.78
Rat (Chronic Oral)
1.81
Fathead Minnow
3.98
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
345.86
Hydration Free Energy
-6.45
Log(D) at pH=7.4
1.3
Log(P)
1.32
Log S
-2.91
Log(Vapor Pressure)
-6.12
Melting Point
76.61
pKa Acid
10.53
pKa Basic
5.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9235
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9235
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9225
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9225
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9056
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9056
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9007
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9007
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8841
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8841
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8818
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8818
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8511
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8511
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8508
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8508
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8339
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8339
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8134
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8134
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8121
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8121
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8094
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8094
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8041
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8041
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8014
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8014
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7980
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7980
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7930
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7930
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7911
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7911
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7827
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7827
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7826
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7826
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7826
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7826
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7798
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7798
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7726
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7726
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7651
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7651
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7650
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7650
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7601
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7601
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7551
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7551
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7538
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7538
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7536
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7536
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7535
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7535
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7470
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7470
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7443
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7443
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7430
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7430
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7265
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7265
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7118
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7118
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7097
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7097
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7091
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7091
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7074
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7074
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7063
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7063
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7046
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7046
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7044
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7044
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7036
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7036

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