(+)-Hippeastrine

ID: ALA457606

Cas Number: 477-17-8

PubChem CID: 441594

Max Phase: Preclinical

Molecular Formula: C17H17NO5

Molecular Weight: 315.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+)-Hippeastrine | Hippeastrine|477-17-8|HIPPEASTRINE HBr|Hippeastrine hydrobromide|22352-41-6|CHEBI:5724|(2S,3S,9S,10S)-9-hydroxy-4-methyl-11,16,18-trioxa-4-azapentacyclo[11.7.0.02,10.03,7.015,19]icosa-1(20),7,13,15(19)-tetraen-12-one|(+)-Hippeastrine|Prestwick3_000675|Hippeastrine (Hydrobromide)|BSPBio_000769|BPBio1_000847|CHEMBL457606|SCHEMBL4278126|DTXSID20197244|HMS2097G11|NSC731436|NSC-731436|AB00513886|NS00094650|C08528|BRD-K71003802-001-02-9|Q27106869|Lycorenan-7-one, 5-hydroxy-1-methyl-Show More⌵

Canonical SMILES:  CN1CCC2=C[C@H](O)[C@H]3OC(=O)c4cc5c(cc4[C@H]3[C@@H]21)OCO5

Standard InChI:  InChI=1S/C17H17NO5/c1-18-3-2-8-4-11(19)16-14(15(8)18)9-5-12-13(22-7-21-12)6-10(9)17(20)23-16/h4-6,11,14-16,19H,2-3,7H2,1H3/t11-,14-,15+,16+/m0/s1

Standard InChI Key:  DGQPIOQRPAGNGB-DANNLKNASA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
    7.1886   -2.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1867   -0.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4787   -2.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4800   -1.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6951   -1.1432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2086   -1.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6929   -2.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9010   -1.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9010   -2.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3365   -1.3967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6165   -0.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3365   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6168   -2.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0432   -3.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0506   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3235   -3.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6112   -3.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9961   -4.0139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3281   -4.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1485   -4.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1931   -3.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6154   -0.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0418   -1.8121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8189   -2.8436    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8143   -3.2499    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7643   -2.2349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  8  2  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
 12 15  1  0
 13 17  1  0
 16 14  2  0
 14 15  1  0
 16 17  1  0
  6  7  1  0
  7  3  1  0
  8  9  1  0
  3  4  2  0
  3  1  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
  1  9  2  0
 18 21  1  0
 11 22  2  0
  8 11  1  0
 12 23  1  1
  9 13  1  0
 13 24  1  1
 12 10  1  0
 17 25  1  6
 10 11  1  0
 15 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA457606

   Hippeastrine

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 315.33

Molecular Weight (Monoisotopic): 315.1107

AlogP: 1.04

#Rotatable Bonds: ┄

Polar Surface Area: 68.23

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.76

CX Basic pKa: 7.62

CX LogP: 0.73

CX LogD: 0.31

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.57

Np Likeness Score: 2.28

References

1. Antoun MD, Mendoza NT, Ríos YR, Proctor GR, Wickramaratne DB, Pezzuto JM, Kinghorn AD..  (1993)  Cytotoxicity of Hymenocallis expansa alkaloids.,  56  (8): [PMID:8229020] [10.1021/np50098a030]

2. Cedrón JC, Gutiérrez D, Flores N, Ravelo ÁG, Estévez-Braun A..  (2013)  Preparation and antimalarial activity of semisynthetic lycorenine derivatives.,  63  [PMID:23567962] [10.1016/j.ejmech.2013.03.018]

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

4. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(2):

• Scientific Literature
• IMI-CARE SARS-CoV-2 Data