Secologanoside

ID: ALA4864856

PubChem CID: 164619212

Max Phase: Preclinical

Molecular Formula: C16H22O11

Molecular Weight: 390.34

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)O)[C@H]1CC(=O)O

Standard InChI:  InChI=1S/C16H22O11/c1-2-6-7(3-10(18)19)8(14(23)24)5-25-15(6)27-16-13(22)12(21)11(20)9(4-17)26-16/h2,5-7,9,11-13,15-17,20-22H,1,3-4H2,(H,18,19)(H,23,24)/t6-,7+,9-,11-,12+,13-,15?,16+/m1/s1

Standard InChI Key:  RGTONEMDTVVDMY-SINQKQORSA-N

Molfile:  

 
     RDKit          2D

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    5.8194   -4.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8194   -4.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288   -5.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2382   -4.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2382   -4.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288   -3.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288   -6.1372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8170   -6.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -6.1334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006   -6.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3964   -7.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081   -7.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8199   -7.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5269   -2.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2388   -2.4381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8151   -2.4381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1123   -5.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3998   -4.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1105   -3.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6927   -2.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8713   -2.9656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1034   -2.2504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -6.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934   -5.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1053   -8.5964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5315   -7.7772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6830   -7.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
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  4  5  1  0
  5  6  2  0
  3  7  1  0
  8  7  1  1
  8  9  1  0
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  9 10  1  0
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 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
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 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
M  END

Alternative Forms

1. Parent:

   

   ALA4864856

   ---

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: 390.34

Molecular Weight (Monoisotopic): 390.1162

AlogP: -1.98

#Rotatable Bonds: 7

Polar Surface Area: 183.21

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.57

CX Basic pKa: ┄

CX LogP: -1.91

CX LogD: -8.30

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.26

Np Likeness Score: 2.68

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