(1R,3S,4S,5S,6S,7R,8S)-4beta-(chloromethyl)-3beta,4alpha-dihydroxy,8alpha-(sarracenoyloxy)-1alphaH, 5alphaH,6betaH,7alphaH-guai-10(14),11(13)-dien-6,12-olide - Compound Card

(1R,3S,4S,5S,6S,7R,8S)-4beta-(chloromethyl)-3beta,4alpha-dihydroxy,8alpha-(sarracenoyloxy)-1alphaH, 5alphaH,6betaH,7alphaH-guai-10(14),11(13)-dien-6,12-olide

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(1R,3S,4S,5S,6S,7R,8S)-4beta-(chloromethyl)-3beta,4alpha-dihydroxy,8alpha-(sarracenoyloxy)-1alphaH, 5alphaH,6betaH,7alphaH-guai-10(14),11(13)-dien-6,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC/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@H](C2)O)(O)CCl
InChI InChI=1S/C20H25ClO7/c1-4-11(7-22)19(25)27-13-5-9(2)12-6-14(23)20(26,8-21)16(12)17-15(13)10(3)18(24)28-17/h4,12-17,22-23,26H,2-3,5-8H2,1H3/b11-4+/t12-,13-,14-,15+,16-,17-,20+/m0/s1
InChIKey NTJXRKLCTXJGGS-XJDQSTAGSA-N
Formula C20H25ClO7
HBA 7
HBD 3
MW 412.87
Rotatable Bonds 4
TPSA 113.29
LogP 0.86
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 412.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea scoparia Asteraceae Plantae 2072395

Showing of synonyms

  • Youssef DTA (1998). Sesquiterpene lactones from Centaurea scoparia. Phytochemistry,1998,49(6),1733-1737. [View] [PubMed]
Pubchem: 100927641

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C3C(CCC3)C(=C)CC2

Level: 0

Mol. Weight: 412.87 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.530
Plasma Protein Binding
57.26
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
7.470
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.520
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.450
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.610
Micronucleos
Toxic
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
-7.320
Rat (Acute)
4.100
Rat (Chronic Oral)
2.430
Fathead Minnow
4.030
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
441.550
Hydration Free Energy
-8.240
Log(D) at pH=7.4
1.350
Log(P)
1.01
Log S
-2.84
Log(Vapor Pressure)
-9.18
Melting Point
148.76
pKa Acid
6.81
pKa Basic
4.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8430
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8430
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7477
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7477
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7139
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7139

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