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

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

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6alpha-angeloyloxygermacra-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=C(/C(=O)O[C@@H]1/C=C(\C)/CC/C=C(/C[C@H]2[C@H]1C(=C)C(=O)O2)\C)\C
InChI InChI=1S/C20H26O4/c1-6-14(4)19(21)23-16-10-12(2)8-7-9-13(3)11-17-18(16)15(5)20(22)24-17/h6,9-10,16-18H,5,7-8,11H2,1-4H3/b12-10+,13-9+,14-6+/t16-,17+,18+/m1/s1
InChIKey TVZVGKUKJBIRJK-ULWCJKCRSA-N
Formula C20H26O4
HBA 4
HBD 0
MW 330.42
Rotatable Bonds 2
TPSA 52.6
LogP 4.04
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 330.18
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: 163013634
Nmrshiftdb2: 70000147

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 330.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.64
Plasma Protein Binding
61.6
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
6.96
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.37
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.19
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.76
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
1.41
Rat (Acute)
2.1
Rat (Chronic Oral)
2.04
Fathead Minnow
5.05
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
351.55
Hydration Free Energy
-4.36
Log(D) at pH=7.4
3.66
Log(P)
4.46
Log S
-4.96
Log(Vapor Pressure)
-5.74
Melting Point
100.58
pKa Acid
10.02
pKa Basic
4.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8655
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8655
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8645
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8645
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7896
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7896
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7831
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7831
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7830
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7830
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7795
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7795
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7693
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7693
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7683
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7683
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7562
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7562
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7494
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7494
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7431
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7431
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7426
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7426
Retinoic acid receptor gamma P13631 RARG_HUMAN Homo sapiens 3 0.7357
Retinoic acid receptor gamma P13631 RARG_HUMAN Homo sapiens 3 0.7357
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7341
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7341
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7336
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7336
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7329
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7329
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7302
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7302
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7286
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7286
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7284
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7284
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7263
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7263
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7253
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7253
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7228
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7228
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7159
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7159
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7107
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7107
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7083
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7083
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7054
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7054

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