3-O-acetylsanguinine

ID: ALA4573785

PubChem CID: 11197829

Max Phase: Preclinical

Molecular Formula: C18H21NO4

Molecular Weight: 315.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1C=C[C@@]23CCN(C)Cc4ccc(O)c(c42)O[C@H]3C1

Standard InChI:  InChI=1S/C18H21NO4/c1-11(20)22-13-5-6-18-7-8-19(2)10-12-3-4-14(21)17(16(12)18)23-15(18)9-13/h3-6,13,15,21H,7-10H2,1-2H3/t13-,15-,18-/m0/s1

Standard InChI Key:  LBXRKDGNBSYDML-YEWWUXTCSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   31.3995   -8.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1152   -8.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8265   -8.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8265   -9.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1152   -9.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3995   -9.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7900   -9.8848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1244  -10.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9402  -10.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4270  -11.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0883  -11.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2746  -12.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7880  -11.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9618  -11.3932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2633  -11.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1803  -10.5253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5768   -9.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8895  -10.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9739  -10.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6842   -8.9220    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.1152   -7.2732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3998   -6.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3998   -6.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6845   -7.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  1  0
  1  6  1  0
  6  7  1  0
  8  7  1  0
  9  8  2  0
  5  9  1  0
  9 10  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  8 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  0
 17 16  1  0
 18 17  1  0
  5 18  1  6
 16 19  1  0
  6 20  1  6
  2 21  1  1
 21 22  1  0
 22 23  2  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4573785

   [(1S,12S,14R)-9-hydroxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-yl] acetate

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: 315.37

Molecular Weight (Monoisotopic): 315.1471

AlogP: 2.12

#Rotatable Bonds: 1

Polar Surface Area: 59.00

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.87

CX Basic pKa: 8.51

CX LogP: 1.22

CX LogD: 0.24

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: 2.41

References

1. Nair JJ, van Staden J..  (2019)  Antiprotozoal alkaloid principles of the plant family Amaryllidaceae.,  29  (20): [PMID:31515186] [10.1016/j.bmcl.2019.126642]

Source

Source(1):

• Scientific Literature