1alpha-hydroxy-6-angeloyloxygermacra-4,10(14),11(13)-trien-8alpha,12-olide - Compound Card

1alpha-hydroxy-6-angeloyloxygermacra-4,10(14),11(13)-trien-8alpha,12-olide

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1alpha-hydroxy-6-angeloyloxygermacra-4,10(14),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@@H](C(=C)C[C@H]2[C@H]1C(=C)C(=O)O2)O)\C
InChI InChI=1S/C20H26O5/c1-6-12(3)19(22)24-16-9-11(2)7-8-15(21)13(4)10-17-18(16)14(5)20(23)25-17/h6,9,15-18,21H,4-5,7-8,10H2,1-3H3/b11-9+,12-6+/t15-,16+,17-,18-/m0/s1
InChIKey UPYSSTOWRYYTEG-GNCXSGPVSA-N
Formula C20H26O5
HBA 5
HBD 1
MW 346.42
Rotatable Bonds 2
TPSA 72.83
LogP 3.01
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 346.18
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: 44588010
Nmrshiftdb2: 70031223

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 346.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
55.77
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
8.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.16
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.03
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.18
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
-1.44
Rat (Acute)
2.78
Rat (Chronic Oral)
1.95
Fathead Minnow
4.64
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
361.76
Hydration Free Energy
-7.05
Log(D) at pH=7.4
2.42
Log(P)
2.91
Log S
-3.98
Log(Vapor Pressure)
-6.75
Melting Point
131.71
pKa Acid
8.44
pKa Basic
4.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8147
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8147
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7985
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7985
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7691
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7691
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7342
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7342
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7256
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7256
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7256
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7256
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7216
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7216
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7195
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7195
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7081
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7081
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7059
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7059

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