NP-MRD: Showing NP-Card for tryptanthrin (NP0001508)

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Record Information

Version

2.0

Created at

2020-08-20 19:32:27 UTC

Updated at

2021-08-10 02:54:49 UTC

NP-MRD ID

NP0001508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tryptanthrin

Description

Indolo[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. tryptanthrin is found in Apis cerana, Calanthe discolor, Elephas maximus, Isatis indigotica , Oceanibulbus idolifex gen. nov., sp.nov., Persicaria tinctoria and Phaius mishmensis. tryptanthrin was first documented in 2021 (PMID: 34254701). Based on a literature review a small amount of articles have been published on Indolo[2,1-b]quinazoline-6,12-dione (PMID: 34225624) (PMID: 34135755) (PMID: 34000190) (PMID: 33951699).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1533004171514092D          

 19 22  0  0  0  0            999 V2000
    2.8119    1.7485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745    0.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.3944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997   -0.6780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990   -0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037   -1.6385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
  6 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  3 19  1  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001508

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
VQQVWGVXDIPORV-UHFFFAOYSA-N

> <FORMULA>
C15H8N2O2

> <MOLECULAR_WEIGHT>
248.241

> <EXACT_MASS>
248.058577506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
25.261525592272466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6H,12H-indolo[2,1-b]quinazoline-6,12-dione

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
2.3956623936666666

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.94101239979379

> <JCHEM_POLAR_SURFACE_AREA>
49.74

> <JCHEM_REFRACTIVITY>
71.61820000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tryptanthrin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       5.249   3.264   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.552   1.754   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.397   0.736   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.700  -0.774   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.159  -1.266   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.315  -0.248   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.774  -0.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.930   0.278   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.627   1.788   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.167   2.280   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.012   1.262   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.358  -1.529   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.180  -3.059   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.225  -0.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.692  -0.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.200   0.626   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.442   2.026   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.976   2.170   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.867   0.914   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2    6                                                  
CONECT   12    4   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    3   14                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    NP0001508
HETATM    1  O1  UNL     1       1.577  -2.399  -2.153  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.352  -1.509  -1.296  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.381  -0.879  -0.495  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.769  -1.022  -0.413  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.497  -0.267   0.464  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.888   0.651   1.287  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.528   0.811   1.227  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.782   0.044   0.334  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.382  -0.008   0.055  1.00  0.00           N  
HETATM   10  C8  UNL     1       0.088  -0.903  -0.893  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.185  -1.128  -1.326  1.00  0.00           N  
HETATM   12  C9  UNL     1      -2.203  -0.435  -0.796  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.520  -0.646  -1.221  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.554   0.074  -0.667  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.241   1.004   0.318  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.940   1.204   0.730  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.916   0.489   0.179  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.617   0.710   0.612  1.00  0.00           C  
HETATM   19  O2  UNL     1      -0.352   1.554   1.503  1.00  0.00           O  
HETATM   20  H1  UNL     1       4.219  -1.759  -1.080  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.588  -0.396   0.512  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.508   1.241   1.980  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.032   1.519   1.857  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.720  -1.386  -1.997  1.00  0.00           H  
HETATM   25  H6  UNL     1      -5.588  -0.073  -0.983  1.00  0.00           H  
HETATM   26  H7  UNL     1      -5.042   1.581   0.767  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.714   1.927   1.494  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4    4    8
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9
CONECT    9   10   18
CONECT   10   11   11
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   24
CONECT   14   15   15   25
CONECT   15   16   26
CONECT   16   17   17   27
CONECT   17   18
CONECT   18   19   19
END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Tryptanthrine	HMDB
6,12-Dihydro-6,12-dioxoindole(2,1-b)quinazoline	HMDB
Tryptanthrin	HMDB
Indolo(2,1-b)quinazolin-6,12-dione	MeSH
Indolo (2, 1b) quinazoline-6, 12 dione	MeSH

Chemical Formula

C₁₅H₈N₂O₂

Average Mass

248.2410 Da

Monoisotopic Mass

248.05858 Da

IUPAC Name

6H,12H-indolo[2,1-b]quinazoline-6,12-dione

Traditional Name

tryptanthrin

CAS Registry Number

Not 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 Key

VQQVWGVXDIPORV-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500Mz MHz, CDCL3, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500Mz, CDCL3, simulated)	john.cort@pnnl.gov	Not Available	Not Available	2020-08-20	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Calanthe aristurifera	KNApSAcK Database	22123792
Calanthe discolor	LOTUS Database	35616633
Calanthe discolor Lindl	KNApSAcK Database	22123792
Calanthe liukiuensis Schltr	KNApSAcK Database	22123792
Calanthe reflexa	KNApSAcK Database	22123792
Couroupita guianensis	KNApSAcK Database	22123792
Elephas maximus	-	KNApSAcK
Isatis indigotica	KNApSAcK Database	22123792
Isatis tinctoria	Plant	KNApSAcK
Isatis tinctoria L	KNApSAcK Database	22123792
Oceanibulbus idolifex gen. nov., sp.nov.	-	KNApSAcK
Persicaria tinctoria	LOTUS Database	35616633
Phaius mishmensis	LOTUS Database	35616633
Polygonum tinctorium	KNApSAcK Database	22123792
Polygonum tinctorum	KNApSAcK Database	22123792
Strobilanthes cusia	KNApSAcK Database	22123792
Wrightia tinctoria	KNApSAcK Database	22123792

Species Where Detected

Species Name	Source	Reference
Candida albicans	KNApSAcK Database	22123792
Candida lipolytica	KNApSAcK Database	22123792
Schizophyllum commune	KNApSAcK Database	22123792

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Indoloquinazolines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:9768 )
organonitrogen heterocyclic compound (CHEBI:9768 )
alkaloid antibiotic (CHEBI:9768 )
Quinazoline alkaloids (C10742 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.8	ALOGPS
logP	2.4	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.74 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.62 m³·mol⁻¹	ChemAxon
Polarizability	25.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0253473

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002200

Chemspider ID

66232

KEGG Compound ID

C10742

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73549

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
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 ]
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 ]
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 ]
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 ]

Showing NP-Card for tryptanthrin (NP0001508)

MOL for NP0001508 (tryptanthrin)

3D MOL for NP0001508 (tryptanthrin)

3D SDF for NP0001508 (tryptanthrin)

3D-SDF for NP0001508 (tryptanthrin)

PDB for NP0001508 (tryptanthrin)

3D PDB for NP0001508 (tryptanthrin)

SMILES for NP0001508 (tryptanthrin)

INCHI for NP0001508 (tryptanthrin)

Structure for NP0001508 (tryptanthrin)

3D Structure for NP0001508 (tryptanthrin)