NP-MRD: Showing NP-Card for Prochaetoglobosin II (NP0079266)

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Record Information

Version

2.0

Created at

2022-04-29 00:18:05 UTC

Updated at

2022-04-29 00:18:05 UTC

NP-MRD ID

NP0079266

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Prochaetoglobosin II

Description

(3S,4S,6aS,10S,17aR,17bR)-1-hydroxy-3-[(1H-indol-3-yl)methyl]-4,5,10,12-tetramethyl-3H,4H,6aH,9H,10H,13H,14H,17H,17bH-cyclotrideca[e]isoindole-14,17-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. Prochaetoglobosin II is found in Chaetomium globosum CANUN60 and Chaetomium subaffine. Based on a literature review very few articles have been published on (3S,4S,6aS,10S,17aR,17bR)-1-hydroxy-3-[(1H-indol-3-yl)methyl]-4,5,10,12-tetramethyl-3H,4H,6aH,9H,10H,13H,14H,17H,17bH-cyclotrideca[e]isoindole-14,17-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202182D          

 37 41  0  0  1  0            999 V2000
    2.7835   -2.3039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3870   -2.8664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.7577   -1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9688   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3599   -0.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3 19  1  0  0  0  0
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 13 21  1  0  0  0  0
 11 22  1  1  0  0  0
  3 23  1  6  0  0  0
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  2 26  1  0  0  0  0
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 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 29 36  2  0  0  0  0
  1 37  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292202182D          

 37 41  0  0  1  0            999 V2000
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  6  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  2  0  0  0  0
 13 21  1  0  0  0  0
 11 22  1  1  0  0  0
  3 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 32  2  0  0  0  0
 30 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 29 36  2  0  0  0  0
  1 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0079266

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CNC4=CC=CC=C34)NC(=O)[C@@]22[C@H](C=C1C)\C=C\C[C@H](C)\C=C(C)/CC(=O)\C=C\C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H36N2O3/c1-19-8-7-9-24-16-21(3)22(4)30-28(17-23-18-33-27-11-6-5-10-26(23)27)34-31(37)32(24,30)29(36)13-12-25(35)15-20(2)14-19/h5-7,9-14,16,18-19,22,24,28,30,33H,8,15,17H2,1-4H3,(H,34,37)/b9-7+,13-12+,20-14-/t19-,22+,24-,28-,30-,32+/m0/s1

> <INCHI_KEY>
ZWMGAOFPDWVLLV-CLRJEDPQSA-N

> <FORMULA>
C32H36N2O3

> <MOLECULAR_WEIGHT>
496.651

> <EXACT_MASS>
496.272593027

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.161524981048956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.77

> <JCHEM_LOGP>
5.791913415000001

> <ALOGPS_LOGS>
-5.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.065089918294507

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.383824291518572

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6219143222108974

> <JCHEM_POLAR_SURFACE_AREA>
79.03

> <JCHEM_REFRACTIVITY>
150.90009999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.69e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.196  -4.301   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.322  -5.351   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.795  -4.900   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.141  -3.399   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.014  -2.349   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.542  -2.800   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.405  -1.688   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.614  -2.949   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.960  -1.448   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.432  -0.997   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.714  -2.092   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.253  -2.118   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.704  -3.591   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.443  -4.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.993  -6.099   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.178  -7.178   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.521  -6.549   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.394  -5.499   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.357  -5.935   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.933  -7.605   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      16.243  -4.014   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.283  -2.430   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.679  -6.161   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.278  -6.784   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       7.752  -7.391   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       6.296  -6.890   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.944  -7.766   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.169  -9.308   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.067 -10.384   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.750 -11.764   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       6.274 -11.542   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       6.533 -10.024   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.896 -13.046   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.359 -12.947   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.677 -11.567   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.531 -10.285   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.576  -4.573   0.000  0.00  0.00           C+0
CONECT    1    2    6   37                                                  
CONECT    2    1    3   26                                                  
CONECT    3    2    4   19   23                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    3   20                                                  
CONECT   20   19                                                            
CONECT   21   13                                                            
CONECT   22   11                                                            
CONECT   23    3   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    2   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   28                                                       
CONECT   33   30   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   29                                                       
CONECT   37    1                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₆N₂O₃

Average Mass

496.6510 Da

Monoisotopic Mass

496.27259 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CNC4=CC=CC=C34)NC(=O)[C@@]22[C@H](C=C1C)\C=C\C[C@H](C)\C=C(C)/CC(=O)\C=C\C2=O

InChI Identifier

InChI=1S/C32H36N2O3/c1-19-8-7-9-24-16-21(3)22(4)30-28(17-23-18-33-27-11-6-5-10-26(23)27)34-31(37)32(24,30)29(36)13-12-25(35)15-20(2)14-19/h5-7,9-14,16,18-19,22,24,28,30,33H,8,15,17H2,1-4H3,(H,34,37)/b9-7+,13-12+,20-14-/t19-,22+,24-,28-,30-,32+/m0/s1

InChI Key

ZWMGAOFPDWVLLV-CLRJEDPQSA-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 globosum CANUN60	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
Ketone
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	4.77	ALOGPS
logP	5.79	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	14.38	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	150.9 m³·mol⁻¹	ChemAxon
Polarizability	55.16 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

162845039

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Prochaetoglobosin II (NP0079266)

MOL for NP0079266 (Prochaetoglobosin II)

3D MOL for NP0079266 (Prochaetoglobosin II)

3D SDF for NP0079266 (Prochaetoglobosin II)

3D-SDF for NP0079266 (Prochaetoglobosin II)

PDB for NP0079266 (Prochaetoglobosin II)

3D PDB for NP0079266 (Prochaetoglobosin II)

SMILES for NP0079266 (Prochaetoglobosin II)

INCHI for NP0079266 (Prochaetoglobosin II)

Structure for NP0079266 (Prochaetoglobosin II)

3D Structure for NP0079266 (Prochaetoglobosin II)