3alpha,4alpha-epoxy-1alpha-hydroxy-9alpha-angeloyloxy-alpha-cyclocostunolide - Compound Card

3alpha,4alpha-epoxy-1alpha-hydroxy-9alpha-angeloyloxy-alpha-cyclocostunolide

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3alpha,4alpha-epoxy-1alpha-hydroxy-9alpha-angeloyloxy-alpha-cyclocostunolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C=C(\C(=O)O[C@@H]1CC2C(=C)C(=O)O[C@@H]2[C@@H]2C1(C)[C@@H](O)C[C@@H]1[C@@]2(C)O1)/C
InChI InChI=1S/C20H26O6/c1-6-9(2)17(22)24-13-7-11-10(3)18(23)25-15(11)16-19(13,4)12(21)8-14-20(16,5)26-14/h6,11-16,21H,3,7-8H2,1-2,4-5H3/b9-6-/t11?,12-,13+,14+,15-,16+,19?,20+/m0/s1
InChIKey IGYHYOUVNMWJAC-QDDCQIRESA-N
Formula C20H26O6
HBA 6
HBD 1
MW 362.42
Rotatable Bonds 2
TPSA 85.36
LogP 1.91
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 362.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pluchea dioscoridis Asteraceae Plantae —

Showing of synonyms

  • Dawidar AA, Metwally M (1985). New alpha-cyclocostunolide and isocostic acid derivatives from Pluchea dioscoridis. Chemical and Pharmaceutical Bulletin,1985,33(11),5068-5070. [View]
Pubchem: 162985747

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(CC2)C1C3C2CCC(O4)C34

Level: 0

Mol. Weight: 362.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.1
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.31
Plasma Protein Binding
34.74
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.52
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.63
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.66
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.91
Micronucleos
Toxic
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
-6.36
Rat (Acute)
4.68
Rat (Chronic Oral)
1.59
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
385.71
Hydration Free Energy
-5.94
Log(D) at pH=7.4
1.54
Log(P)
2.41
Log S
-3.06
Log(Vapor Pressure)
-6.97
Melting Point
125.91
pKa Acid
6.16
pKa Basic
3.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8791
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8791
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8548
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8548
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8493
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8493
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8316
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8316
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8065
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8065
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7529
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7529
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7442
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7442
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7362
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7362
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7226
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7226
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7167
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7167
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7157
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7157
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7139
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7139
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7134
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7134
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7131
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7131
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7123
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7123
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7113
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7113
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7090
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7090
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7065
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7065
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7055
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7055
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7055
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7055
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7039
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7039
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7025
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7025
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7014
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7014
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7010
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7010
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7007
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7007

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