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Record Information
Version1.0
Created at2020-08-20 19:32:27 UTC
Updated at2021-08-10 02:54:49 UTC
NP-MRD IDNP0001508
Secondary Accession NumbersNone
Natural Product Identification
Common Nametryptanthrin
DescriptionIndolo[2,1-b]quinazoline-6,12-dione, also known as tryptanthrine, belongs to the class of organic compounds known as indoloquinazolines. These are polycyclic aromatic compounds containing an indole fused to a quinazoline. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Quinazoline is a heterocyclic compound consisting of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring. It was first documented in 2021 (PMID: 34254701). Based on a literature review a significant number of articles have been published on Indolo[2,1-b]quinazoline-6,12-dione (PMID: 34225624) (PMID: 34135755) (PMID: 34000190) (PMID: 33951699).
Structure
Data?1628564089
Synonyms
ValueSource
TryptanthrineHMDB
6,12-Dihydro-6,12-dioxoindole(2,1-b)quinazolineHMDB
TryptanthrinHMDB
Indolo(2,1-b)quinazolin-6,12-dioneMeSH
Indolo (2, 1b) quinazoline-6, 12 dioneMeSH
Chemical FormulaC15H8N2O2
Average Mass248.2410 Da
Monoisotopic Mass248.05858 Da
IUPAC Name6H,12H-indolo[2,1-b]quinazoline-6,12-dione
Traditional Nametryptanthrin
CAS Registry NumberNot Available
SMILES
O=C1C2=NC3=CC=CC=C3C(=O)N2C2=CC=CC=C12
InChI Identifier
InChI=1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H
InChI KeyVQQVWGVXDIPORV-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500Mz MHz, CDCL3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500Mz, CDCL3, simulated)John.cort2020-08-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Calanthe aristuriferaKNApSAcK Database
Calanthe discolor LindlKNApSAcK Database
Calanthe liukiuensis SchltrKNApSAcK Database
Calanthe reflexaKNApSAcK Database
Couroupita guianensisKNApSAcK Database
Isatis indigoticaKNApSAcK Database
Isatis tinctoria LKNApSAcK Database
Polygonum tinctoriumKNApSAcK Database
Polygonum tinctorumKNApSAcK Database
Strobilanthes cusiaKNApSAcK Database
Wrightia tinctoriaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Candida albicansKNApSAcK Database
Candida lipolyticaKNApSAcK Database
Schizophyllum communeKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoloquinazolines. These are polycyclic aromatic compounds containing an indole fused to a quinazoline. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Quinazoline is a heterocyclic compound consisting of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentIndoloquinazolines
Alternative Parents
Substituents
  • Indoloquinazoline
  • Indole
  • Indole or derivatives
  • Aryl ketone
  • Pyrimidone
  • Pyrimidine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Ketone
  • Lactam
  • Azacycle
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10(1.8) g/LALOGPS
logP10(2.4) g/LChemAxon
logS10(-3.5) g/LALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area49.74 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.62 m³·mol⁻¹ChemAxon
Polarizability25.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0253473
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002200
Chemspider ID66232
KEGG Compound IDC10742
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73549
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Huang H, Li Y, Dai Y, Zhang Y, Lu Q, Xu Q, Zhang Y: Antileukemic effects of indigo naturalis constituents by "target constituent knock-out" coupled with semipreparative liquid chromatography and quadrupole time-of-flight mass spectrometry. Biomed Chromatogr. 2021 Jul 13:e5216. doi: 10.1002/bmc.5216. [PubMed:34254701 ]
  2. Swain SS, Hussain T, Pati S: Drug-Lead Anti-tuberculosis Phytochemicals: A Systematic Review. Curr Top Med Chem. 2021 Jul 5. pii: CTMC-EPUB-116467. doi: 10.2174/1568026621666210705170510. [PubMed:34225624 ]
  3. Sun Q, Leng J, Tang L, Wang L, Fu C: A Comprehensive Review of the Chemistry, Pharmacokinetics, Pharmacology, Clinical Applications, Adverse Events, and Quality Control of Indigo Naturalis. Front Pharmacol. 2021 May 31;12:664022. doi: 10.3389/fphar.2021.664022. eCollection 2021. [PubMed:34135755 ]
  4. Feng FF, Wang XQ, Sun L, Cheung CW, Nie J, Ma JA: Switching of Enantioselectivity in the Cu-Catalyzed Asymmetric Decarboxylative Aldol Reaction of Tryptanthrin with beta-Keto Acids: An Unexpected Counteranion Effect. Org Lett. 2021 Jun 4;23(11):4379-4384. doi: 10.1021/acs.orglett.1c01315. Epub 2021 May 17. [PubMed:34000190 ]
  5. Shi X, Zhang Y, Han J, Peng W, Fang Z, Qin Y, Xu X, Lin J, Xiao F, Zhao L, Lin Y: Tryptanthrin Regulates Vascular Smooth Muscle Cell Phenotypic Switching in Atherosclerosis by AMP-Activated Protein Kinase/Acetyl-CoA Carboxylase Signaling Pathway. J Cardiovasc Pharmacol. 2021 May 1;77(5):642-649. doi: 10.1097/FJC.0000000000001008. [PubMed:33951699 ]