Speciociliatine

ID: ALA4546925

Cas Number: 14382-79-7

PubChem CID: 15560576

Product Number: S353356, Order Now?

Max Phase: Preclinical

Molecular Formula: C23H30N2O4

Molecular Weight: 398.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@@H]1CN2CCc3c([nH]c4cccc(OC)c34)[C@H]2C[C@@H]1/C(=C\OC)C(=O)OC

Standard InChI:  InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19-/m1/s1

Standard InChI Key:  LELBFTMXCIIKKX-MYLQJJOTSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   17.1197  -11.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6988  -10.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5750  -12.2785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5878  -13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9411  -11.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3414  -10.9330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1751  -12.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8898  -11.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8155  -11.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3538  -12.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1751  -13.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1627  -10.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5837  -11.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0991  -10.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9287  -10.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4091  -13.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5961  -14.4742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3620  -13.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8177  -12.3487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2253  -10.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0685  -12.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3968  -11.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9576  -14.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6391  -12.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8012  -10.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4824  -10.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4040  -11.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6439  -12.4147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3042   -9.8473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6392   -9.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  7  4  1  1
  5  1  1  0
  6  5  1  0
  7 10  1  0
  8  2  1  0
  9  3  1  0
 10  5  1  0
 11  4  1  0
 12  6  1  0
 13  7  1  0
 14  2  1  0
 15  6  1  0
 16  4  2  0
 17 11  2  0
 18 11  1  0
 19 16  1  0
 20  8  2  0
 21  9  2  0
 13 22  1  1
 23 18  1  0
 24 19  1  0
 25 22  1  0
 26 20  1  0
 27 21  1  0
  5 28  1  1
  8  9  1  0
 15 14  1  0
 12 13  1  0
 26 27  2  0
 20 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4546925

   Speciociliatine

Molecule Features

Natural Product: No

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: 398.50

Molecular Weight (Monoisotopic): 398.2206

AlogP: 3.83

#Rotatable Bonds: 5

Polar Surface Area: 63.79

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.04

CX LogP: 3.30

CX LogD: 3.14

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: 1.54

References

1. Obeng S, Kamble SH, Reeves ME, Restrepo LF, Patel A, Behnke M, Chear NJ, Ramanathan S, Sharma A, León F, Hiranita T, Avery BA, McMahon LR, McCurdy CR..  (2020)  Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.,  63  (1): [PMID:31834797] [10.1021/acs.jmedchem.9b01465]

2. Chear NJ, León F, Sharma A, Kanumuri SRR, Zwolinski G, Abboud KA, Singh D, Restrepo LF, Patel A, Hiranita T, Ramanathan S, Hampson AJ, McMahon LR, McCurdy CR..  (2021)  Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors.,  84  (4.0): [PMID:33635670] [10.1021/acs.jnatprod.0c01055]

3. Kamble SH, Berthold EC, King TI, Raju Kanumuri SR, Popa R, Herting JR, León F, Sharma A, McMahon LR, Avery BA, McCurdy CR..  (2021)  Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.,  84  (4.0): [PMID:33620222] [10.1021/acs.jnatprod.0c01163]

4. León F, Obeng S, Mottinelli M, Chen Y, King TI, Berthold EC, Kamble SH, Restrepo LF, Patel A, Gamez-Jimenez LR, Lopera-Londoño C, Hiranita T, Sharma A, Hampson AJ, Canal CE, McMahon LR, McCurdy CR..  (2021)  Activity of Mitragyna speciosa ("Kratom") Alkaloids at Serotonin Receptors.,  64  (18.0): [PMID:34467758] [10.1021/acs.jmedchem.1c00726]

5. Smith MT, Kong D, Kuo A, Imam MZ, Williams CM..  (2022)  Analgesic Opioid Ligand Discovery Based on Nonmorphinan Scaffolds Derived from Natural Sources.,  65  (3.0): [PMID:34995453] [10.1021/acs.jmedchem.0c01915]

6. Chakraborty S, Uprety R, Slocum ST, Irie T, Le Rouzic V, Li X, Wilson LL, Scouller B, Alder AF, Kruegel AC, Ansonoff M, Varadi A, Eans SO, Hunkele A, Allaoa A, Kalra S, Xu J, Pan YX, Pintar J, Kivell BM, Pasternak GW, Cameron MD, McLaughlin JP, Sames D, Majumdar S..  (2021)  Oxidative Metabolism as a Modulator of Kratom's Biological Actions.,  64  (22.0): [PMID:34783240] [10.1021/acs.jmedchem.1c01111]

Source

Source(1):

• Scientific Literature