(2E,4E,12E)-13-(benzo[d][1,3]dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide

ID: ALA404184

Chembl Id: CHEMBL404184

Cas Number: 55038-30-7

PubChem CID: 6442405

Max Phase: Preclinical

Molecular Formula: C24H33NO3

Molecular Weight: 383.53

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Guineensine | Guineesine | Pipyahyine | guineensine|Guineesine|55038-30-7|Pipyahyine|(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide|(E,E,E)-Guineensine|7DK8DMU9JX|2,4,12-Tridecatrienamide, 13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (2E,4E,12E)-|2,4,12-Tridecatrienamide, 13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (E,E,E)-|UNII-7DK8DMU9JX|MLS002473215|CHEMBL404184|SCHEMBL11309623|CHEBI:181825|FPMPOFBEYSSYDQ-AUVZEZIHSA-N|DTXSID801336042|HMS2268L12|BDBM5047Show More⌵

Canonical SMILES:  CC(C)CNC(=O)/C=C/C=C/CCCCCC/C=C/c1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C24H33NO3/c1-20(2)18-25-24(26)14-12-10-8-6-4-3-5-7-9-11-13-21-15-16-22-23(17-21)28-19-27-22/h8,10-17,20H,3-7,9,18-19H2,1-2H3,(H,25,26)/b10-8+,13-11+,14-12+

Standard InChI Key:  FPMPOFBEYSSYDQ-AUVZEZIHSA-N

Alternative Forms

1. Parent:

   

   ALA404184

   GUINEENSINE

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: 383.53

Molecular Weight (Monoisotopic): 383.2460

AlogP: 5.65

#Rotatable Bonds: 12

Polar Surface Area: 47.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 6.14

CX LogD: 6.14

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.29

Np Likeness Score: 0.81

References

1. Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, Yoshikawa M..  (2008)  Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.,  18  (6): [PMID:18289853] [10.1016/j.bmcl.2008.01.101]

2. Zhang H, Matsuda H, Nakamura S, Yoshikawa M..  (2008)  Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.,  18  (11): [PMID:18477507] [10.1016/j.bmcl.2008.04.052]

3. Lee SW, Kim YK, Kim K, Lee HS, Choi JH, Lee WS, Jun CD, Park JH, Lee JM, Rho MC..  (2008)  Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.,  18  (16): [PMID:18672369] [10.1016/j.bmcl.2008.07.045]

4. Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, Yoshikawa M..  (2009)  Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.,  17  (20): [PMID:19775895] [10.1016/j.bmc.2009.08.050]

5. Lenta BN, Tantangmo F, Devkota KP, Wansi JD, Chouna JR, Soh RC, Neumann B, Stammler HG, Tsamo E, Sewald N..  (2009)  Bioactive constituents of the stem bark of Beilschmiedia zenkeri.,  72  (12): [PMID:19904919] [10.1021/np900341f]

6. PubChem BioAssay data set, 

7. Jiang ZY, Liu WF, Zhang XM, Luo J, Ma YB, Chen JJ..  (2013)  Anti-HBV active constituents from Piper longum.,  23  (7): [PMID:23434420] [10.1016/j.bmcl.2013.01.118]

8. da Silva JB, Navarro DM, da Silva AG, Santos GK, Dutra KA, Moreira DR, Ramos MN, Espíndola JW, de Oliveira AD, Brondani DJ, Leite AC, Hernandes MZ, Pereira VR, da Rocha LF, de Castro MC, de Oliveira BC, Lan Q, Merz KM..  (2015)  Thiosemicarbazones as Aedes aegypti larvicidal.,  100  [PMID:26087027] [10.1016/j.ejmech.2015.04.061]

9. Cunningham CW..  (2019)  Plant-Based Modulators of Endocannabinoid Signaling.,  82  (3): [PMID:30816712] [10.1021/acs.jnatprod.8b00874]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays