3-hydroxy-7,8-dimethoxyserrulat-14-en-19-oic acid methyl ester

ID: ALA5271594

Max Phase: Preclinical

Molecular Formula: C23H34O5

Molecular Weight: 390.52

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc2c(c(OC)c1OC)[C@H](C)C[C@@H](O)[C@H]2[C@@H](C)CCC=C(C)C

Standard InChI:  InChI=1S/C23H34O5/c1-13(2)9-8-10-14(3)19-16-12-17(23(25)28-7)21(26-5)22(27-6)20(16)15(4)11-18(19)24/h9,12,14-15,18-19,24H,8,10-11H2,1-7H3/t14-,15+,18+,19-/m0/s1

Standard InChI Key:  DFSZRMLMJHCTHC-SFUIVIKGSA-N

Molfile:  

 
     RDKit          2D

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    0.3601    2.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    1.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    0.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3620    0.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543    0.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    0.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    2.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    2.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601    2.8981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    2.0721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    0.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066    0.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893   -0.4096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5066    0.4149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3546   -0.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7891   -0.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7891   -1.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -2.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -2.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3546   -3.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7891   -3.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7891    0.0007    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    3.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    2.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066    1.6610    0.0000 C   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
  6  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
  1 10  1  0
 10 11  1  1
  2 12  1  0
  3 13  1  0
  4 14  1  0
 14 15  1  0
 14 16  2  0
  8 17  1  6
  7 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
  7 26  1  1
 12 27  1  0
 13 28  1  0
 15 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5271594

   ---

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: 390.52

Molecular Weight (Monoisotopic): 390.2406

AlogP: 4.82

#Rotatable Bonds: 7

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.77

CX LogD: 4.77

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: 1.69

References

1. Zhang C, Lum KY, Taki AC, Gasser RB, Byrne JJ, Montaner LJ, Tietjen I, Avery VM, Davis RA..  (2023)  Using a Bioactive Eremophila-Derived Serrulatane Scaffold to Generate a Unique Carbamate Library for Anti-infective Evaluations.,  86  (3): [PMID:36799121] [10.1021/acs.jnatprod.2c01041]

Source

Source(1):

• Scientific Literature