12beta-O-[deca-2Z,4E-dienoyl]-13alpha-isobutyryl-5-ene-7-oxo-4beta-phorbol

ID: ALA4538168

PubChem CID: 155549089

Max Phase: Preclinical

Molecular Formula: C34H46O9

Molecular Weight: 598.73

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCC/C=C/C=C\C(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@@H](C(=O)C(CO)=C[C@]3(O)C(=O)C(C)=C[C@@H]23)[C@@H]2C(C)(C)[C@]12OC(=O)C(C)C

Standard InChI:  InChI=1S/C34H46O9/c1-8-9-10-11-12-13-14-15-24(36)42-29-21(5)33(41)23-16-20(4)28(38)32(23,40)17-22(18-35)26(37)25(33)27-31(6,7)34(27,29)43-30(39)19(2)3/h12-17,19,21,23,25,27,29,35,40-41H,8-11,18H2,1-7H3/b13-12+,15-14-/t21-,23-,25+,27-,29-,32-,33+,34-/m1/s1

Standard InChI Key:  GOFSCWBZJWJLTF-GKOQXERBSA-N

Molfile:  

 
     RDKit          2D

 46 49  0  0  0  0  0  0  0  0999 V2000
   38.4917   -6.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7755   -6.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4796   -7.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2318   -7.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5901   -7.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8733   -8.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6903   -8.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9114   -7.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1701   -9.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9886   -9.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5271   -8.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4207   -9.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8035   -7.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3092  -10.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1205  -10.1405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4572   -9.3693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6624   -7.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3859   -7.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3312   -6.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6320   -6.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1308   -7.0121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   37.0833   -8.2865    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.9109   -6.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3055   -5.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.0546   -6.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0825   -7.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6445   -8.0227    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   37.6377   -6.0453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4325   -8.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6321   -5.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3369   -4.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0475   -5.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9216   -4.8214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3313   -3.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5854   -5.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5597   -4.2120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8908   -5.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1706   -5.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1450   -4.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4248   -3.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3992   -3.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6790   -2.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6534   -1.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9332   -1.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9076   -0.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3143   -8.8930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 17  1  0
  7  9  1  0
  9 10  2  0
 18 11  1  0
 10 11  1  0
  6 12  2  0
  5 13  1  0
 10 14  1  0
 14 15  1  0
  7 16  1  1
 17 18  1  0
 17 20  1  0
 18 26  1  0
 25 19  1  0
 19 20  1  0
  8 21  1  6
 18 22  1  1
 20 23  1  6
 19 24  1  1
 26 25  1  0
  2 26  1  0
 25  2  1  0
 26 27  1  6
 25 28  1  6
 17 29  1  6
 28 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  2  0
 31 34  1  0
 24 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 11 46  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538168

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 598.73

Molecular Weight (Monoisotopic): 598.3142

AlogP: 3.56

#Rotatable Bonds: 10

Polar Surface Area: 147.43

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.22

CX Basic pKa: ┄

CX LogP: 4.85

CX LogD: 4.85

Aromatic Rings: ┄

Heavy Atoms: 43

QED Weighted: 0.15

Np Likeness Score: 2.81

References

1. Nothias-Esposito M, Nothias LF, Da Silva RR, Retailleau P, Zhang Z, Leyssen P, Roussi F, Touboul D, Paolini J, Dorrestein PC, Litaudon M..  (2019)  Investigation of Premyrsinane and Myrsinane Esters in Euphorbia cupanii and Euphobia pithyusa with MS2LDA and Combinatorial Molecular Network Annotation Propagation.,  82  (6): [PMID:31181921] [10.1021/acs.jnatprod.8b00916]

Source

Source(1):

• Scientific Literature