NP-MRD: Showing NP-Card for Chaetoglobosin E (NP0058016)

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Record Information

Version

2.0

Created at

2022-04-28 03:21:09 UTC

Updated at

2022-04-28 03:21:09 UTC

NP-MRD ID

NP0058016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chaetoglobosin E

Description

(3S,6S,6aR,10S,14R,17aS,17bR)-1,6,14-trihydroxy-3-[(1H-indol-3-yl)methyl]-4,5,10,12-tetramethyl-3H,6H,6aH,9H,10H,13H,14H,15H,16H,17H,17bH-cyclotrideca[e]isoindole-13,17-dione belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Chaetoglobosin E is found in Chaetomium cochlioides, Chaetomium globosum, Chaetomium mollipilium and Chaetomium subaffine. Based on a literature review very few articles have been published on (3S,6S,6aR,10S,14R,17aS,17bR)-1,6,14-trihydroxy-3-[(1H-indol-3-yl)methyl]-4,5,10,12-tetramethyl-3H,6H,6aH,9H,10H,13H,14H,15H,16H,17H,17bH-cyclotrideca[e]isoindole-13,17-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205212D          

 39 43  0  0  1  0            999 V2000
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 20 39  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282205212D          

 39 43  0  0  1  0            999 V2000
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    0.7692   -2.8857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0290   -2.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0258   -1.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597   -1.2393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7661   -1.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6566   -2.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8240   -3.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4158   -3.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0466   -2.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8422   -1.5278    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 29 28  1  1  0  0  0
 15 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 33 32  1  1  0  0  0
 11 33  1  0  0  0  0
 15 33  1  0  0  0  0
 32 34  1  0  0  0  0
 31 35  1  0  0  0  0
 30 36  1  6  0  0  0
 25 37  1  1  0  0  0
 23 38  1  0  0  0  0
 20 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0058016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C\C=C\[C@H]2[C@H](O)C(C)=C(C)[C@H]3[C@H](CC4=CNC5=CC=CC=C45)NC(=O)[C@@]23C(=O)CC[C@@H](O)C(=O)\C(C)=C\1

> <INCHI_IDENTIFIER>
InChI=1S/C32H38N2O5/c1-17-8-7-10-23-30(38)20(4)19(3)28-25(15-21-16-33-24-11-6-5-9-22(21)24)34-31(39)32(23,28)27(36)13-12-26(35)29(37)18(2)14-17/h5-7,9-11,14,16-17,23,25-26,28,30,33,35,38H,8,12-13,15H2,1-4H3,(H,34,39)/b10-7+,18-14+/t17-,23-,25-,26+,28-,30+,32+/m0/s1

> <INCHI_KEY>
FPNAKNFLJIQADW-LACRMWCASA-N

> <FORMULA>
C32H38N2O5

> <MOLECULAR_WEIGHT>
530.665

> <EXACT_MASS>
530.278072332

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
58.30962073363638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6S,6aR,10S,14R,17aR,17bR)-6,14-dihydroxy-3-[(1H-indol-3-yl)methyl]-4,5,10,12-tetramethyl-1H,2H,3H,6H,6aH,9H,10H,13H,14H,15H,16H,17H,17bH-cyclotrideca[e]isoindole-1,13,17-trione

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
3.8786980606666672

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.0439836646668

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.279549258087869

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5588241157293954

> <JCHEM_POLAR_SURFACE_AREA>
119.49000000000001

> <JCHEM_REFRACTIVITY>
152.54600000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,6aR,10S,14R,17aR,17bR)-6,14-dihydroxy-3-(1H-indol-3-ylmethyl)-4,5,10,12-tetramethyl-2H,3H,6H,6aH,9H,10H,14H,15H,16H,17bH-cyclotrideca[e]isoindole-1,13,17-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.159   5.626   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.559   4.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.261   2.960   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.800   3.019   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.519   4.382   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.698   5.685   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.724   1.777   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.154   2.349   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.052   3.886   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.347   0.284   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.451  -0.789   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.968  -0.527   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.473  -1.847   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.211  -2.109   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.613  -2.993   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.972  -1.996   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.608  -2.729   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.349  -0.503   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.886  -0.400   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.458  -1.830   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.936  -2.639   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.234  -1.810   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.038  -4.176   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.759  -5.033   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.861  -6.569   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.581  -7.426   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.200  -6.746   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.097  -5.210   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.716  -4.530   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.436  -5.387   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.054  -4.707   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.048  -3.170   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.231  -2.313   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.430  -2.490   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.226  -5.564   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.538  -6.923   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.243  -7.249   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.420  -4.855   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.306  -2.852   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    2                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   29   33                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   39                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   38                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   37                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   15   30                                                  
CONECT   30   29   31   36                                                  
CONECT   31   30   32   35                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32   11   15                                                  
CONECT   34   32                                                            
CONECT   35   31                                                            
CONECT   36   30                                                            
CONECT   37   25                                                            
CONECT   38   23                                                            
CONECT   39   20                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₈N₂O₅

Average Mass

530.6650 Da

Monoisotopic Mass

530.27807 Da

IUPAC Name

(3S,6S,6aR,10S,14R,17aR,17bR)-6,14-dihydroxy-3-[(1H-indol-3-yl)methyl]-4,5,10,12-tetramethyl-1H,2H,3H,6H,6aH,9H,10H,13H,14H,15H,16H,17H,17bH-cyclotrideca[e]isoindole-1,13,17-trione

Traditional Name

(3S,6S,6aR,10S,14R,17aR,17bR)-6,14-dihydroxy-3-(1H-indol-3-ylmethyl)-4,5,10,12-tetramethyl-2H,3H,6H,6aH,9H,10H,14H,15H,16H,17bH-cyclotrideca[e]isoindole-1,13,17-trione

CAS Registry Number

Not Available

SMILES

C[C@H]1C\C=C\[C@H]2[C@H](O)C(C)=C(C)[C@H]3[C@H](CC4=CNC5=CC=CC=C45)NC(=O)[C@@]23C(=O)CC[C@@H](O)C(=O)\C(C)=C\1

InChI Identifier

InChI=1S/C32H38N2O5/c1-17-8-7-10-23-30(38)20(4)19(3)28-25(15-21-16-33-24-11-6-5-9-22(21)24)34-31(39)32(23,28)27(36)13-12-26(35)29(37)18(2)14-17/h5-7,9-11,14,16-17,23,25-26,28,30,33,35,38H,8,12-13,15H2,1-4H3,(H,34,39)/b10-7+,18-14+/t17-,23-,25-,26+,28-,30+,32+/m0/s1

InChI Key

FPNAKNFLJIQADW-LACRMWCASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chaetomium cochliodes	Fungi	KNApSAcK
Chaetomium globosum	Fungi	KNApSAcK
Chaetomium mollipilium	Fungi	KNApSAcK
Chaetomium subaffine	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Isoindole or derivatives
Isoindole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Cyclic carboximidic acid
Pyrroline
Pyrrole
Cyclic ketone
Secondary alcohol
Ketone
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.09	ALOGPS
logP	3.88	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.28	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	152.55 m³·mol⁻¹	ChemAxon
Polarizability	58.31 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162884111

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Chaetoglobosin E (NP0058016)

MOL for NP0058016 (Chaetoglobosin E)

3D MOL for NP0058016 (Chaetoglobosin E)

3D SDF for NP0058016 (Chaetoglobosin E)

3D-SDF for NP0058016 (Chaetoglobosin E)

PDB for NP0058016 (Chaetoglobosin E)

3D PDB for NP0058016 (Chaetoglobosin E)

SMILES for NP0058016 (Chaetoglobosin E)

INCHI for NP0058016 (Chaetoglobosin E)

Structure for NP0058016 (Chaetoglobosin E)

3D Structure for NP0058016 (Chaetoglobosin E)