Cyclomyltaylyl-10-caffeate

ID: ALA5279047

Max Phase: Preclinical

Molecular Formula: C24H30O4

Molecular Weight: 382.50

Names and Identifiers

Canonical SMILES:  CC1(C)[C@H](OC(=O)/C=C/c2ccc(O)c(O)c2)CC[C@]2(C)[C@H]3C4C[C@@]12C[C@]43C

Standard InChI:  InChI=1S/C24H30O4/c1-21(2)18(28-19(27)8-6-14-5-7-16(25)17(26)11-14)9-10-23(4)20-15-12-24(21,23)13-22(15,20)3/h5-8,11,15,18,20,25-26H,9-10,12-13H2,1-4H3/b8-6+/t15?,18-,20+,22-,23-,24-/m1/s1

Standard InChI Key:  HYDVBLCOEZLRAU-ZEIALKAVSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   -4.0580   -0.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435   -0.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -1.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3417   -1.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0580   -1.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725   -0.1134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7725   -1.7668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -0.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2028   -0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4883   -0.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261   -0.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4883    0.7119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9406   -0.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9406    0.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6550    1.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3695    0.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3695   -0.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -0.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1735    0.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6442    0.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523   -0.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4644   -0.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1408    0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725    1.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3695    1.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3552    1.7668    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  1  7  1  0
  6  8  1  0
  3  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 14 12  1  6
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 19 18  1  0
 14 19  1  0
 17 20  1  0
 20 21  1  0
 22 21  1  0
 18 22  1  1
 18 23  1  0
 20 24  1  0
 24 23  1  0
 21 24  1  0
 24 25  1  1
 17 26  1  1
 19 27  1  0
 19 28  1  0
 20 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5279047

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 382.50

Molecular Weight (Monoisotopic): 382.2144

AlogP: 4.90

#Rotatable Bonds: 3

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.21

CX Basic pKa: ┄

CX LogP: 4.95

CX LogD: 4.94

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: 2.01

References

1. Asakawa Y, Ludwiczuk A..  (2018)  Chemical Constituents of Bryophytes: Structures and Biological Activity.,  81  (3): [PMID:29019405] [10.1021/acs.jnatprod.6b01046]

Source

Source(1):

• Scientific Literature