(1S,3S,5R,6R,7R,8S)-8- angelyloxy-3-hydroxyguai-3(15),10(14),11(13)-trien-6,12-olide - Compound Card

(1S,3S,5R,6R,7R,8S)-8- angelyloxy-3-hydroxyguai-3(15),10(14),11(13)-trien-6,12-olide

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(1S,3S,5R,6R,7R,8S)-8- angelyloxy-3-hydroxyguai-3(15),10(14),11(13)-trien-6,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C=C(/C(=O)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)C(=C)[C@H](C2)O)\C
InChI InChI=1S/C20H24O5/c1-6-9(2)19(22)24-15-7-10(3)13-8-14(21)11(4)16(13)18-17(15)12(5)20(23)25-18/h6,13-18,21H,3-5,7-8H2,1-2H3/b9-6+/t13-,14-,15-,16-,17+,18+/m0/s1
InChIKey SDRJABGPZHYDOV-FPEITNRTSA-N
Formula C20H24O5
HBA 5
HBD 1
MW 344.41
Rotatable Bonds 2
TPSA 72.83
LogP 2.48
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 344.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea scoparia Asteraceae Plantae 2072395

Showing of synonyms

  • Helal AM, Nakamura N, et al. (1997). Guaianolides from Centaurea scoparia. Phytochemistry,1997,45(3),551-554. [View]
Pubchem: 14137169
Nmrshiftdb2: 60018802

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(C1C23)CCC(=C)C3CCC2=C

Level: 0

Mol. Weight: 344.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.58
Plasma Protein Binding
63.2
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.11
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.81
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.87
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.37
Rat (Acute)
3.58
Rat (Chronic Oral)
1.86
Fathead Minnow
4.16
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
369.3
Hydration Free Energy
-6.38
Log(D) at pH=7.4
2.3
Log(P)
2.43
Log S
-3.74
Log(Vapor Pressure)
-7.42
Melting Point
159.55
pKa Acid
7.65
pKa Basic
3.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7190
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7190
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7163
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7163

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