1-acetyl-beta-carboline

ID: ALA1682931

Cas Number: 50892-83-6

PubChem CID: 638667

Product Number: A649865, Order Now?

Max Phase: Preclinical

Molecular Formula: C13H10N2O

Molecular Weight: 210.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1nccc2c1[nH]c1ccccc12

Standard InChI:  InChI=1S/C13H10N2O/c1-8(16)12-13-10(6-7-14-12)9-4-2-3-5-11(9)15-13/h2-7,15H,1H3

Standard InChI Key:  NXZSUJKPVSDFNF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 18  0  0  0  0  0  0  0  0999 V2000
    3.5392   -6.1333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606   -5.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -4.8633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5639   -4.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595   -4.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4960   -5.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0565   -5.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418   -4.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2122   -5.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0177   -5.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5662   -5.1816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2994   -4.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4860   -4.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2891   -6.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7406   -7.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1005   -6.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  2  1  0
  2  3  2  0
  9  1  1  0
  8  9  2  0
  3  4  1  0
  9 10  1  0
  1  2  1  0
 10 11  2  0
  4  5  2  0
 11 12  1  0
  3  8  1  0
 12 13  2  0
 13  8  1  0
  5  6  1  0
 10 14  1  0
 14 15  2  0
  6  7  2  0
 14 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1682931

   1-Acetyl-β-carboline

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: 210.24

Molecular Weight (Monoisotopic): 210.0793

AlogP: 2.92

#Rotatable Bonds: 1

Polar Surface Area: 45.75

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.00

CX Basic pKa: 3.01

CX LogP: 1.82

CX LogD: 1.82

Aromatic Rings: 3

Heavy Atoms: 16

QED Weighted: 0.63

Np Likeness Score: 0.23

References

1. Dillman RL, Cardellina JH.  (1991)  Aromatic Secondary Metabolites from the Sponge Tedania ignis,  54  (4): [10.1021/np50076a021]

2. Yang ML, Kuo PC, Hwang TL, Chiou WF, Qian K, Lai CY, Lee KH, Wu TS..  (2011)  Synthesis, in vitro anti-inflammatory and cytotoxic evaluation, and mechanism of action studies of 1-benzoyl-β-carboline and 1-benzoyl-3-carboxy-β-carboline derivatives.,  19  (5): [PMID:21316977] [10.1016/j.bmc.2011.01.034]

3. Huang H, Yao Y, He Z, Yang T, Ma J, Tian X, Li Y, Huang C, Chen X, Li W, Zhang S, Zhang C, Ju J..  (2011)  Antimalarial β-carboline and indolactam alkaloids from Marinactinospora thermotolerans, a deep sea isolate.,  74  (10): [PMID:21977916] [10.1021/np200399t]

4. Sasaki T, Li W, Higai K, Koike K..  (2015)  Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.,  25  (9): [PMID:25819098] [10.1016/j.bmcl.2015.03.014]

5. Lindberg MF, Deau E, Arfwedson J, George N, George P, Alfonso P, Corrionero A, Meijer L..  (2023)  Comparative Efficacy and Selectivity of Pharmacological Inhibitors of DYRK and CLK Protein Kinases.,  66  (6): [PMID:36876904] [10.1021/acs.jmedchem.2c02068]

Source

Source(1):

• Scientific Literature