himeic acid A

ID: ALA2046773

PubChem CID: 11774903

Max Phase: Preclinical

Molecular Formula: C22H29NO8

Molecular Weight: 435.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Himeic Acid A | Himeic Acid A|(E)-11-[5-[[(3S)-3-carboxybutanoyl]carbamoyl]-4-oxopyran-2-yl]undec-10-enoic acid|Himeic acid A_120102|CHEMBL2046773|SCHEMBL23760360|CHEBI:214481

Canonical SMILES:  C[C@@H](CC(=O)NC(=O)c1coc(/C=C/CCCCCCCCC(=O)O)cc1=O)C(=O)O

Standard InChI:  InChI=1S/C22H29NO8/c1-15(22(29)30)12-19(25)23-21(28)17-14-31-16(13-18(17)24)10-8-6-4-2-3-5-7-9-11-20(26)27/h8,10,13-15H,2-7,9,11-12H2,1H3,(H,26,27)(H,29,30)(H,23,25,28)/b10-8+/t15-/m0/s1

Standard InChI Key:  OKGLROPOZIVCCZ-HQPKTYMTSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -0.8500  -11.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8500  -11.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1380  -12.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740  -11.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740  -11.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1380  -10.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1380   -9.7583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657  -10.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5681   -9.7646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2789  -11.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2838   -9.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2862   -8.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9970   -9.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7127   -9.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4260   -9.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1433   -9.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252  -10.5965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7151   -8.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879  -12.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2867  -13.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0006  -13.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9994  -14.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133  -14.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7121  -15.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259  -15.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4247  -16.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1386  -17.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374  -18.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8513  -18.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511  -19.2575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5674  -18.0210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  8  1  0
 15 16  1  0
 15 17  2  0
  1  6  1  0
 14 18  1  1
  8  9  1  0
  4 19  1  0
  2  3  1  0
 19 20  2  0
  8 10  2  0
 20 21  1  0
  3  4  1  0
 21 22  1  0
  9 11  1  0
 22 23  1  0
  4  5  2  0
 23 24  1  0
 11 12  2  0
 24 25  1  0
  5  6  1  0
 25 26  1  0
 11 13  1  0
 26 27  1  0
 27 28  1  0
 13 14  1  0
 28 29  1  0
  6  7  2  0
 14 15  1  0
 29 30  1  0
 29 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2046773

   HIMEIC ACID A

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: 435.47

Molecular Weight (Monoisotopic): 435.1893

AlogP: 3.23

#Rotatable Bonds: 14

Polar Surface Area: 150.98

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.80

CX Basic pKa: ┄

CX LogP: 2.93

CX LogD: -2.67

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: 0.97

References

1. Yamanokuchi R, Imada K, Miyazaki M, Kato H, Watanabe T, Fujimuro M, Saeki Y, Yoshinaga S, Terasawa H, Iwasaki N, Rotinsulu H, Losung F, Mangindaan RE, Namikoshi M, de Voogd NJ, Yokosawa H, Tsukamoto S..  (2012)  Hyrtioreticulins A-E, indole alkaloids inhibiting the ubiquitin-activating enzyme, from the marine sponge Hyrtios reticulatus.,  20  (14): [PMID:22695182] [10.1016/j.bmc.2012.05.044]

2. da Silva SR, Paiva SL, Lukkarila JL, Gunning PT..  (2013)  Exploring a new frontier in cancer treatment: targeting the ubiquitin and ubiquitin-like activating enzymes.,  56  (6): [PMID:23360215] [10.1021/jm301420b]

Source

Source(1):

• Scientific Literature