4,4'-(di-O-valinoyl)curcumin

ID: ALA455159

PubChem CID: 25111344

Max Phase: Preclinical

Molecular Formula: C31H38N2O8

Molecular Weight: 566.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(OC(=O)[C@@H](N)C(C)C)c(OC)c2)ccc1OC(=O)[C@@H](N)C(C)C

Standard InChI:  InChI=1S/C31H38N2O8/c1-18(2)28(32)30(36)40-24-13-9-20(15-26(24)38-5)7-11-22(34)17-23(35)12-8-21-10-14-25(27(16-21)39-6)41-31(37)29(33)19(3)4/h7-16,18-19,28-29H,17,32-33H2,1-6H3/b11-7+,12-8+/t28-,29-/m0/s1

Standard InChI Key:  RVFUPBDRJITFOE-ILTOYGKPSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA455159

   [4-[(1E,6E)-7-[4-[(2S)-2-amino-3-methylbutanoyl]oxy-3-methoxyphenyl]-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] (2S)-2-amino-3-methylbutanoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 566.65

Molecular Weight (Monoisotopic): 566.2628

AlogP: 3.74

#Rotatable Bonds: 14

Polar Surface Area: 157.24

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.64

CX Basic pKa: 7.61

CX LogP: 5.01

CX LogD: 4.49

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.15

Np Likeness Score: 0.40

References

1. Dubey SK, Sharma AK, Narain U, Misra K, Pati U..  (2008)  Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties.,  43  (9): [PMID:18201805] [10.1016/j.ejmech.2007.11.027]

2. Harish G, Venkateshappa C, Mythri RB, Dubey SK, Mishra K, Singh N, Vali S, Bharath MM..  (2010)  Bioconjugates of curcumin display improved protection against glutathione depletion mediated oxidative stress in a dopaminergic neuronal cell line: Implications for Parkinson's disease.,  18  (7): [PMID:20227282] [10.1016/j.bmc.2010.02.029]

3. Zhang W, Bai H, Han L, Zhang H, Xu B, Cui J, Wang X, Ge Z, Li R..  (2018)  Synthesis and biological evaluation of curcumin derivatives modified with α-amino boronic acid as proteasome inhibitors.,  28  (14): [PMID:29886021] [10.1016/j.bmcl.2018.06.004]

Source

Source(1):

• Scientific Literature