(1R,3S,4S,5S,6S,7R,8S)-4beta-(chloromethyl)- 3beta,4alpha-dihydroxy-8alpha-(3-formyl-2-methyl-propenoyloxy)-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-(3-formyl-2-methyl-propenoyloxy)-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-(3-formyl-2-methyl-propenoyloxy)-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 O=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)\C
InChI InChI=1S/C20H23ClO7/c1-9(4-5-22)18(24)27-13-6-10(2)12-7-14(23)20(26,8-21)16(12)17-15(13)11(3)19(25)28-17/h4-5,12-17,23,26H,2-3,6-8H2,1H3/b9-4+/t12-,13-,14-,15+,16-,17-,20+/m0/s1
InChIKey QFRPCGYYWUHGHK-LRJNHNEYSA-N
Formula C20H23ClO7
HBA 7
HBD 2
MW 410.85
Rotatable Bonds 4
TPSA 110.13
LogP 1.07
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 410.11
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: 100927642

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 410.85 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.95
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.540
Plasma Protein Binding
48.16
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
7.840
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.480
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.100
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.530
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
Toxic
T. Pyriformis
-5.740
Rat (Acute)
5.500
Rat (Chronic Oral)
1.820
Fathead Minnow
4.010
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
433.250
Hydration Free Energy
-7.320
Log(D) at pH=7.4
1.580
Log(P)
1.2
Log S
-2.83
Log(Vapor Pressure)
-9.08
Melting Point
138.7
pKa Acid
5.45
pKa Basic
4.03
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 0.8547
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8547
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7828
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7828
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7348
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7348
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7274
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7274
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7186
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7186
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7133
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7133

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