NP-MRD: Showing NP-Card for 1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione (NP0217763)

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Record Information

Version

2.0

Created at

2022-09-05 18:12:49 UTC

Updated at

2022-09-05 18:12:49 UTC

NP-MRD ID

NP0217763

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione

Description

1,13-Dihydroxy-3-[(1H-indol-3-yl)methyl]-4,5,10,12-tetramethyl-3H,4H,6aH,9H,10H,13H,14H,15H,16H,17H,17bH-cyclotrideca[e]isoindole-14,17-dione belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. 1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione is found in Ulva intestinalis. 1,13-Dihydroxy-3-[(1H-indol-3-yl)methyl]-4,5,10,12-tetramethyl-3H,4H,6aH,9H,10H,13H,14H,15H,16H,17H,17bH-cyclotrideca[e]isoindole-14,17-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241511192D          

 38 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241511192D          

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    5.1335    3.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8190    3.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5561    3.5463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7642    2.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8588    2.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4497    1.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3950    1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2747    2.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 23  1  0  0  0  0
 18 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  6 27  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37  2  1  4  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217763

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CNC4=CC=CC=C34)NC(=O)C22C(C=C1C)C=CCC(C)C=C(C)C(O)C(=O)CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H38N2O4/c1-18-8-7-9-23-15-19(2)21(4)29-26(16-22-17-33-25-11-6-5-10-24(22)25)34-31(38)32(23,29)28(36)13-12-27(35)30(37)20(3)14-18/h5-7,9-11,14-15,17-18,21,23,26,29-30,33,37H,8,12-13,16H2,1-4H3,(H,34,38)

> <INCHI_KEY>
TYTBBVIHCPHNMB-UHFFFAOYSA-N

> <FORMULA>
C32H38N2O4

> <MOLECULAR_WEIGHT>
514.666

> <EXACT_MASS>
514.283157712

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.80007226653359

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
4.719186318333334

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.357615107738653

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.814364922001996

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4400541382062535

> <JCHEM_POLAR_SURFACE_AREA>
99.26

> <JCHEM_REFRACTIVITY>
151.16830000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.06e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       9.731   2.107   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.459   1.060   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.887  -0.370   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.350  -0.267   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.973   1.226   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.614   2.223   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.232   1.543   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.953   2.400   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.540   1.660   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.055   3.937   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.632   4.654   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.437   4.617   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.856   6.098   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.785   7.329   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.476   8.739   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.756  10.100   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.828  11.205   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       7.211  10.527   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.640  11.101   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.852  10.150   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.634   8.626   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.205   8.052   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.993   9.003   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       7.395   6.157   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       7.515   4.852   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.167   5.526   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.717   3.760   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.098   4.440   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.147   3.169   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.201   5.976   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.582   6.656   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.862   5.799   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.238   6.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.760   4.263   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.070   4.298   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      12.040   3.406   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.937   1.869   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.579   3.886   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   27                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   27                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   18                                                  
CONECT   24   13   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    6   12   28                                             
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36    2                                                       
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₈N₂O₄

Average Mass

514.6660 Da

Monoisotopic Mass

514.28316 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CNC4=CC=CC=C34)NC(=O)C22C(C=C1C)C=CCC(C)C=C(C)C(O)C(=O)CCC2=O

InChI Identifier

InChI=1S/C32H38N2O4/c1-18-8-7-9-23-15-19(2)21(4)29-26(16-22-17-33-25-11-6-5-10-24(22)25)34-31(38)32(23,29)28(36)13-12-27(35)30(37)20(3)14-18/h5-7,9-11,14-15,17-18,21,23,26,29-30,33,37H,8,12-13,16H2,1-4H3,(H,34,38)

InChI Key

TYTBBVIHCPHNMB-UHFFFAOYSA-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
Ulva intestinalis	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
Pyrrolidine
Pyrrole
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Cyclic ketone
Ketone
Lactam
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Alcohol
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	4.06	ALOGPS
logP	4.72	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.26 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	151.17 m³·mol⁻¹	ChemAxon
Polarizability	57.8 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione (NP0217763)

MOL for NP0217763 (1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione)

3D MOL for NP0217763 (1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione)

3D SDF for NP0217763 (1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione)

3D-SDF for NP0217763 (1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione)

PDB for NP0217763 (1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione)

3D PDB for NP0217763 (1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione)

SMILES for NP0217763 (1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione)

INCHI for NP0217763 (1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione)

Structure for NP0217763 (1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione)

3D Structure for NP0217763 (1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h,15h,16h-cyclotrideca[d]isoindole-14,17-dione)