6alpha-hydroxygermacra-1(10),4,11(13)-trien-8alpha,12-olide - Compound Card

6alpha-hydroxygermacra-1(10),4,11(13)-trien-8alpha,12-olide

Select a section from the left sidebar

6alpha-hydroxygermacra-1(10),4,11(13)-trien-8alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C/1=C\CC/C(=C/[C@H]([C@H]2[C@H](C1)OC(=O)C2=C)O)/C
InChI InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h6-7,12-14,16H,3-5,8H2,1-2H3/b9-7+,10-6+/t12-,13+,14+/m1/s1
InChIKey FRDLPOYYWWRSPZ-MXSOBKCTSA-N
Formula C15H20O3
HBA 3
HBD 1
MW 248.32
Rotatable Bonds 0
TPSA 46.53
LogP 2.52
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 248.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brocchia cinerea Asteraceae Plantae 282208

Showing of synonyms

  • Jakupovic J, Aal MA, et al. (1988). Further glaucolides and other sesquiterpene lactones from Brocchia cinerea.. Phytochemistry,1988,27(7),2219-2224. [View]
Pubchem: 14191561
Nmrshiftdb2: 60031077

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CC=CCCC=CC2

Level: 0

Mol. Weight: 248.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.2
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
47.1
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
7.09
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.07
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.16
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.17
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
1.59
Rat (Acute)
2.22
Rat (Chronic Oral)
1.95
Fathead Minnow
4.42
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
322.3
Hydration Free Energy
-7.13
Log(D) at pH=7.4
2.07
Log(P)
2.88
Log S
-2.96
Log(Vapor Pressure)
-5.44
Melting Point
118.27
pKa Acid
8.67
pKa Basic
5.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8216
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8216
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8132
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8132
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7853
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7853
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7830
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7830
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7788
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7788
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7608
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7608
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7561
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7561
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7508
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7508
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7405
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7405
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7224
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7224
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7187
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7187
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7161
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7161
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7147
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7147
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7096
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7096
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7038
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7038
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7009
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7009

Download SDF