Secoxyloganin

ID: ALA4862269

PubChem CID: 164623606

Max Phase: Preclinical

Molecular Formula: C17H24O11

Molecular Weight: 404.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C[C@H]1C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)O

Standard InChI:  InChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6-8,10,12-14,16-18,21-23H,1,4-5H2,2H3,(H,19,20)/t7-,8+,10-,12-,13+,14-,16?,17+/m1/s1

Standard InChI Key:  MQLSOVRLZHTATK-UTOCKHDASA-N

Molfile:  

 
     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    6.9626  -13.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9626  -13.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6720  -14.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3814  -13.9377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3814  -13.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6720  -12.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6720  -15.1676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9602  -15.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2495  -15.1638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5397  -15.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5355  -16.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2472  -16.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9631  -16.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6702  -11.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3820  -11.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9583  -11.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2514  -14.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5390  -13.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2496  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8359  -11.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0146  -11.9960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2425  -11.2808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8295  -15.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8325  -14.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2444  -17.6268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6748  -16.8076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8221  -16.8006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0938  -11.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  3  7  1  0
  8  7  1  1
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 15  1  0
 14 16  2  0
  6 14  1  0
  2 17  1  6
 17 18  2  0
  1 19  1  6
 19 20  1  0
 20 21  1  0
 20 22  2  0
 10 23  1  1
 23 24  1  0
 12 25  1  1
 13 26  1  6
 11 27  1  6
 15 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4862269

   ---

Molecule Features

Natural Product: Yes

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: 404.37

Molecular Weight (Monoisotopic): 404.1319

AlogP: -1.89

#Rotatable Bonds: 7

Polar Surface Area: 172.21

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.87

CX Basic pKa: ┄

CX LogP: -1.53

CX LogD: -4.76

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.24

Np Likeness Score: 2.57

References

1. Lee JH, Austin JR, Burdette JE, Murphy BT..  (2021)  Secoiridoids from Dogwood (Cornus officinalis) Potentiate Progesterone Signaling.,  84  (9.0): [PMID:34411479] [10.1021/acs.jnatprod.1c00516]

Source

Source(1):

• Scientific Literature