(epi)12-(2-methyl-1-propenyl)-(5aS,12S,14aS)-2,3,5a,6,11,12,14,14a-octahydro-1H,5H-pyrrolo[1',2':4,5]pyrazino[1,2-b]b-carboline-5,14-dione

ID: ALA39346

Chembl Id: CHEMBL39346

Cas Number: 111768-16-2

PubChem CID: 10337896

Max Phase: Preclinical

Molecular Formula: C21H23N3O2

Molecular Weight: 349.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Demethoxyfumitremorgin C | demethoxyfumitremorgin C|111768-16-2|CHEBI:72767|(1S,12S,15S)-12-(2-methylprop-1-enyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4,6,8-tetraene-14,20-dione|(5aS,12S,14aS)-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione|(5aS,12S,14aS)-12-(2-Methylprop-1-en-1-yl)-1,2,3,5a,6,14a-hexahydropyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14(11H,12H)-dShow More⌵

Canonical SMILES:  CC(C)=C[C@H]1c2[nH]c3ccccc3c2C[C@H]2C(=O)N3CCC[C@H]3C(=O)N21

Standard InChI:  InChI=1S/C21H23N3O2/c1-12(2)10-17-19-14(13-6-3-4-7-15(13)22-19)11-18-20(25)23-9-5-8-16(23)21(26)24(17)18/h3-4,6-7,10,16-18,22H,5,8-9,11H2,1-2H3/t16-,17-,18-/m0/s1

Standard InChI Key:  LQXCSIKDOISJTI-BZSNNMDCSA-N

Alternative Forms

1. Parent:

   

   ALA39346

   DEMETHOXYFUMITREMORGIN C

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: 349.43

Molecular Weight (Monoisotopic): 349.1790

AlogP: 2.93

#Rotatable Bonds: 1

Polar Surface Area: 56.41

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.27

CX LogD: 2.27

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: 0.90

References

1. Wang H, Usui T, Osada H, Ganesan A..  (2000)  Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues.,  43  (8): [PMID:10780915] [10.1021/jm9905662]

2. Wang H, Usui T, Osada H, Ganesan A..  (2000)  Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues.,  43  (8): [PMID:10780915] [10.1021/jm9905662]

3. Ge HM, Yu ZG, Zhang J, Wu JH, Tan RX..  (2009)  Bioactive alkaloids from endophytic Aspergillus fumigatus.,  72  (4): [PMID:19256529] [10.1021/np800700e]

4. Motoyama T, Osada H..  (2016)  Biosynthetic approaches to creating bioactive fungal metabolites: Pathway engineering and activation of secondary metabolism.,  26  (24): [PMID:27865702] [10.1016/j.bmcl.2016.11.013]

Source

Source(1):

• Scientific Literature