retrorsine

ID: ALA520570

Cas Number: 15503-87-4

PubChem CID: 5281756

Product Number: U359348, Order Now?

Max Phase: Preclinical

Molecular Formula: C18H25NO6

Molecular Weight: 351.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Retrorsine | Usaramine|15503-87-4|Mucronatine|(15E)-Retrorsine|Usaramin|CHEBI:9912|trans-Retrorsine|(+)-Ursamine|[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, (3E,5R,6S,14aR,14bR)-|(1R,4E,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione|(5R,6S,9a1R,14aR,E)-3-Ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,9a1,11,1Show More⌵

Canonical SMILES:  C/C=C1\C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

Standard InChI:  InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-/m1/s1

Standard InChI Key:  BCJMNZRQJAVDLD-FXGRWVCYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   12.8965   -3.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8815   -2.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4036   -2.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6664   -2.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6756   -3.0843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4603   -3.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9384   -2.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4454   -1.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4824   -2.8392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5341   -1.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2813   -0.8472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6196   -1.2311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9103   -0.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1937   -1.2088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9230    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2144    0.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6443    0.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3483   -0.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0696    0.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3305   -0.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0642    0.3484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3357   -0.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6487    0.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6525    1.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2270    1.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4290    1.7796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8924   -1.8674    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 12 13  1  0
  3  1  1  0
 13 14  2  0
  5  6  1  0
 13 15  1  0
  6  7  1  0
 15 16  2  0
  7  8  2  0
 15 17  1  0
  8  4  1  0
 17 18  1  0
  4  5  1  0
 18 19  1  0
  4  9  1  6
 11 20  1  0
  1  5  1  0
 20 21  2  0
 19 20  1  0
  8 10  1  0
 18 22  1  6
 19 23  1  0
 10 11  1  0
 19 24  1  1
  4  2  1  0
 16 25  1  0
  2 12  1  0
 23 26  1  0
  2 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA520570

   Usaramine

Molecule Features

Natural Product: No

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: 351.40

Molecular Weight (Monoisotopic): 351.1682

AlogP: 0.17

#Rotatable Bonds: 1

Polar Surface Area: 96.30

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.44

CX Basic pKa: 8.14

CX LogP: 0.60

CX LogD: -0.21

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.39

Np Likeness Score: 2.98

References

1. Zalkow LH, Asibal CF, Glinski JA, Bonetti SJ, Gelbaum LT, VanDerveer D, Powis G..  (1988)  Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography.,  51  (4): [PMID:3210016] [10.1021/np50058a005]

2. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

3. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

4.  (2008)  36  (3): [10.1016/jbse.2007.08.015]

5.  (2008)  36  (3): [10.1016/jbse.2007.08.015]

Source

Source(1):

• Scientific Literature