NP-MRD: Showing NP-Card for 1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione (NP0329987)

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Record Information

Version

2.0

Created at

2022-09-12 14:55:04 UTC

Updated at

2022-09-12 14:55:04 UTC

NP-MRD ID

NP0329987

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione

Description

1,11-Dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3H,4H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-12,15-dione belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole. 1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione is found in Mariannaea elegans. 1,11-Dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3H,4H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-12,15-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004261516452D          

 29 31  0  0  0  0            999 V2000
    1.2511   -4.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2798   -3.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -3.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081   -3.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865   -2.2020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685   -1.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -0.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -1.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0660   -0.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6666   -1.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -2.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4009   -2.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1714   -2.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004   -2.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9507   -1.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6790   -0.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7937    0.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2726   -1.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9111   -1.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1222   -2.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9182   -3.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5492   -3.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768   -4.2332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487   -3.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873   -2.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7867   -2.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2242   -2.9618    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  5 16  1  0  0  0  0
  9 16  1  0  0  0  0
 17 10  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  4  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END


  Mrv1533004261516452D          

 29 31  0  0  0  0            999 V2000
    1.2511   -4.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2798   -3.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -3.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081   -3.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865   -2.2020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685   -1.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -0.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -1.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0660   -0.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6666   -1.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -2.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4009   -2.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1714   -2.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004   -2.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9507   -1.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6790   -0.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7937    0.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2726   -1.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9111   -1.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1222   -2.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9182   -3.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5492   -3.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768   -4.2332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487   -3.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873   -2.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7867   -2.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2242   -2.9618    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  5 16  1  0  0  0  0
  9 16  1  0  0  0  0
 17 10  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  4  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0329987

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC1NC(=O)C23C1C(C)C(C)=CC2C=C(C)CCC(O)C(=O)C=CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H33NO4/c1-13(2)10-18-22-16(5)15(4)12-17-11-14(3)6-7-19(26)20(27)8-9-21(28)24(17,22)23(29)25-18/h8-9,11-13,16-19,22,26H,6-7,10H2,1-5H3,(H,25,29)

> <INCHI_KEY>
BVKOTAZOMFVYMH-UHFFFAOYSA-N

> <FORMULA>
C24H33NO4

> <MOLECULAR_WEIGHT>
399.531

> <EXACT_MASS>
399.240958547

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.017081259129675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-hydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-1H,2H,3H,4H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-1,12,15-trione

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
3.6056345203333326

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.417755087842824

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.347482755730269

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3085438930626907

> <JCHEM_POLAR_SURFACE_AREA>
83.47

> <JCHEM_REFRACTIVITY>
115.49319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-2H,3H,4H,6aH,9H,10H,11H,15bH-cycloundeca[e]isoindole-1,12,15-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       2.335  -8.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.389  -7.321   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.083  -6.505   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.748  -6.597   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.802  -5.058   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.588  -4.110   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.115  -2.663   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.253  -1.387   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.654  -2.717   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.723  -1.609   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.844  -2.205   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.642  -3.461   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.949  -4.277   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.348  -4.196   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.787  -5.517   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.854  -3.824   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.375  -1.945   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.734  -1.221   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.948   0.304   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.842  -2.291   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.167  -3.675   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.561  -5.314   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.047  -5.718   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.492  -6.422   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.917  -7.902   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.998  -6.049   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.696  -4.774   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.202  -4.402   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.152  -5.529   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16   28                                             
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    5    9                                                  
CONECT   17   10   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    9   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₃NO₄

Average Mass

399.5310 Da

Monoisotopic Mass

399.24096 Da

IUPAC Name

11-hydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-1H,2H,3H,4H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-1,12,15-trione

Traditional Name

11-hydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-2H,3H,4H,6aH,9H,10H,11H,15bH-cycloundeca[e]isoindole-1,12,15-trione

CAS Registry Number

Not Available

SMILES

CC(C)CC1NC(=O)C23C1C(C)C(C)=CC2C=C(C)CCC(O)C(=O)C=CC3=O

InChI Identifier

InChI=1S/C24H33NO4/c1-13(2)10-18-22-16(5)15(4)12-17-11-14(3)6-7-19(26)20(27)8-9-21(28)24(17,22)23(29)25-18/h8-9,11-13,16-19,22,26H,6-7,10H2,1-5H3,(H,25,29)

InChI Key

BVKOTAZOMFVYMH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mariannaea elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindoles

Direct Parent

Isoindoles

Alternative Parents

Substituents

Isoindole
Pyrroline
Cyclic carboximidic acid
Ketone
Secondary alcohol
Cyclic ketone
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.65	ALOGPS
logP	3.61	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.35	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.47 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	115.49 m³·mol⁻¹	ChemAxon
Polarizability	45.02 Å³	ChemAxon
Number of Rings	3	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

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

72731352

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione (NP0329987)

MOL for NP0329987 (1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione)

3D MOL for NP0329987 (1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione)

3D SDF for NP0329987 (1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione)

3D-SDF for NP0329987 (1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione)

PDB for NP0329987 (1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione)

3D PDB for NP0329987 (1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione)

SMILES for NP0329987 (1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione)

INCHI for NP0329987 (1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione)

Structure for NP0329987 (1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione)

3D Structure for NP0329987 (1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,4h,6ah,9h,10h,11h-cycloundeca[d]isoindole-12,15-dione)