6alpha-hydroxyneopulchellin - Compound Card

6alpha-hydroxyneopulchellin

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6alpha-hydroxyneopulchellin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2[C@@H]([C@]2(C1[C@@H](O)C[C@H]2O)C)O
InChI InChI=1S/C15H22O5/c1-6-4-9-11(7(2)14(19)20-9)13(18)15(3)10(17)5-8(16)12(6)15/h6,8-13,16-18H,2,4-5H2,1,3H3/t6-,8+,9-,10-,11-,12?,13+,15-/m1/s1
InChIKey CHHJAEIMNOFHLW-HTUURHGYSA-N
Formula C15H22O5
HBA 5
HBD 3
MW 282.34
Rotatable Bonds 0
TPSA 86.99
LogP 0.23
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 282.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Gaillardia aristata Asteraceae Plantae 55624

Showing of synonyms

  • Salama MM, Kandil ZA and Islam WT. (2012). Cytotoxic compounds from the leaves of Gaillardia aristata Pursh. growing in Egypt. Natural Product Research,2012,26(22),2057-2062. [View] [PubMed]
Pubchem: 163080696
Nmrshiftdb2: 70069088

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CCC3C(C2)CCC3

Level: 0

Mol. Weight: 282.34 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
47.28
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
3.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.46
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.69
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.55
Rat (Acute)
3.65
Rat (Chronic Oral)
2.32
Fathead Minnow
3.7
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
373.07
Hydration Free Energy
-12.13
Log(D) at pH=7.4
0.42
Log(P)
0.3
Log S
-1.81
Log(Vapor Pressure)
-7.94
Melting Point
167.31
pKa Acid
7.24
pKa Basic
5.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8047
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8047
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7818
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7818
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7696
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7696
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7558
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7558
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7535
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7535
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7349
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7349
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7047
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7047
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7011
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7011
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7007
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7007
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7003
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7003

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