1,3-dioxo-7alpha,11betaH-2,3-secogermacra-4E,10(14)-dien-12,6alpha-olide - Compound Card

1,3-dioxo-7alpha,11betaH-2,3-secogermacra-4E,10(14)-dien-12,6alpha-olide

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1,3-dioxo-7alpha,11betaH-2,3-secogermacra-4E,10(14)-dien-12,6alpha-olide

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C/C(=C/[C@H]1OC(=O)[C@H]([C@@H]1CCC(=C)C(=O)C)C)/C
InChI InChI=1S/C15H20O4/c1-9(8-16)7-14-13(11(3)15(18)19-14)6-5-10(2)12(4)17/h7-8,11,13-14H,2,5-6H2,1,3-4H3/b9-7+/t11-,13-,14+/m0/s1
InChIKey YDKNYLSOYMUTBH-SJWIUKBCSA-N
Formula C15H20O4
HBA 4
HBD 0
MW 264.32
Rotatable Bonds 6
TPSA 60.44
LogP 2.23
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pyrethrum santolinoides Asteraceae-Compositae Plantae 2072400

Showing of synonyms

  • Mahmoud AA, Ahmed AA, et al. (1994). 2,3-secogermacranolides and germacranolides from Pyrethrum santolionoides. Phytochemistry,1994,36(2),393-398. [View]
Pubchem: 101663347
Nmrshiftdb2: 70087154

No compound-protein relationship available.

Structure

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 86.09 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.580
Plasma Protein Binding
51.31
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
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
6.020
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.050
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.770
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.000
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
1.880
Rat (Acute)
3.080
Rat (Chronic Oral)
1.410
Fathead Minnow
4.550
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
338.260
Hydration Free Energy
-6.450
Log(D) at pH=7.4
1.620
Log(P)
1.84
Log S
-2.4
Log(Vapor Pressure)
-5.66
Melting Point
96.45
pKa Acid
7.19
pKa Basic
4.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.9006
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.9006
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8862
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8862
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8521
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8521
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8408
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8408
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8341
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8341
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.8246
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.8246
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8234
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8234
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7925
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7925
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7595
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7595
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7553
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7553
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7512
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7512
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7430
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7430
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7424
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7424
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7301
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7301
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7285
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7285
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7025
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7025
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7021
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7021
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7012
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7012
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7007
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7007

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