NP-MRD: Showing NP-Card for (3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione (NP0207634)

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Record Information

Version

2.0

Created at

2022-09-05 04:19:31 UTC

Updated at

2022-09-05 04:19:31 UTC

NP-MRD ID

NP0207634

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione

Description

Prochaetoglobosin II belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Prochaetoglobosin II is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione is found in Chaetomium subaffine. Based on a literature review very few articles have been published on prochaetoglobosin II.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206192D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052206192D          

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  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 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
 18 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 26 34  1  0  0  0  0
 29 34  1  0  0  0  0
 35 24  1  6  0  0  0
 20 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0207634

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CNC4=CC=CC=C34)N=C(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-WVXRVHBYSA-N

> <FORMULA>
C32H36N2O3

> <MOLECULAR_WEIGHT>
496.651

> <EXACT_MASS>
496.272593027

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.78176916516226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(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

> <JCHEM_LOGP>
5.393477657823285

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.05889563705606

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8567395227456998

> <JCHEM_PKA_STRONGEST_BASIC>
5.58943109164888

> <JCHEM_POLAR_SURFACE_AREA>
82.52000000000001

> <JCHEM_REFRACTIVITY>
151.42180000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.060  -0.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.531  -1.084   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.661  -0.038   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.132  -0.494   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.262   0.552   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.733   0.097   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.863   1.143   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.335   0.687   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.442   1.758   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.779  -0.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.037  -1.826   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.495  -1.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.581  -3.297   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.041  -3.319   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.501  -1.877   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.756  -4.409   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.285  -3.953   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.060  -2.267   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.074  -1.405   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.473  -1.996   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.817  -2.747   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.347  -2.565   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      10.518  -4.258   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       8.989  -4.440   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.237  -5.784   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.026  -7.107   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.559  -7.247   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      10.900  -8.749   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       9.577  -9.537   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.278 -11.048   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.820 -11.544   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.661 -10.529   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.961  -9.018   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.419  -8.522   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.343  -3.042   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.872  -2.586   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.742  -3.632   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    4   21   35                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   35                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   26   29                                                  
CONECT   35   24   20   36                                                  
CONECT   36   35    2   37                                                  
CONECT   37   36                                                            
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,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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CNC4=CC=CC=C34)N=C(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-WVXRVHBYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 subaffine	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
3-alkylindole
Indole
Indole or derivatives
Isoindole
Pyrrolidone
2-pyrrolidone
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Pyrrolidine
Cyclic ketone
Ketone
Lactam
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:68740 )
macrocycle (CHEBI:68740 )
cytochalasan alkaloid (CHEBI:68740 )

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	5.39	ChemAxon
pKa (Strongest Acidic)	2.86	ChemAxon
pKa (Strongest Basic)	5.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	151.42 m³·mol⁻¹	ChemAxon
Polarizability	54.78 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

C00043850

Chemspider ID

30785588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71768072

PDB ID

Not Available

ChEBI ID

68740

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione (NP0207634)

MOL for NP0207634 ((3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione)

3D MOL for NP0207634 ((3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione)

3D SDF for NP0207634 ((3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione)

3D-SDF for NP0207634 ((3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione)

PDB for NP0207634 ((3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione)

3D PDB for NP0207634 ((3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione)

SMILES for NP0207634 ((3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione)

INCHI for NP0207634 ((3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione)

Structure for NP0207634 ((3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione)

3D Structure for NP0207634 ((3s,3ar,4s,6as,10s,17ar)-1-hydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione)