NP-MRD: Showing NP-Card for (3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione (NP0151564)

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Record Information

Version

2.0

Created at

2022-09-02 07:53:35 UTC

Updated at

2022-09-02 07:53:35 UTC

NP-MRD ID

NP0151564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione

Description

Aspochalasin O belongs to the class of organic compounds known as aspochalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears a 2-methylpropyl group. (3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione is found in Mariannaea elegans. Based on a literature review very few articles have been published on Aspochalasin O.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022209532D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022209532D          

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M  END
> <DATABASE_ID>
NP0151564

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]1N=C(O)[C@]23[C@H]1[C@H](C)C(C)=C[C@@H]2\C=C(C)\CC[C@@H](O)C(=O)C[C@@H](CC(C)=O)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H39NO5/c1-14(2)9-21-24-18(6)16(4)11-20-10-15(3)7-8-22(30)23(31)13-19(12-17(5)29)25(32)27(20,24)26(33)28-21/h10-11,14,18-22,24,30H,7-9,12-13H2,1-6H3,(H,28,33)/b15-10+/t18-,19-,20+,21+,22-,24+,27+/m1/s1

> <INCHI_KEY>
JUCPANRNKTTWAB-GEPXZTCASA-N

> <FORMULA>
C27H39NO5

> <MOLECULAR_WEIGHT>
457.611

> <EXACT_MASS>
457.28282336

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.0004568016394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,6aS,11R,14R,15aR,15bR)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3H,4H,6aH,9H,10H,11H,12H,13H,14H,15H,15bH-cycloundeca[e]isoindole-12,15-dione

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
4.064608712333334

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.262703418749727

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.590425513695793

> <JCHEM_PKA_STRONGEST_BASIC>
2.8225636508364222

> <JCHEM_POLAR_SURFACE_AREA>
104.02999999999999

> <JCHEM_REFRACTIVITY>
129.33689999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,6aS,11R,14R,15aR,15bR)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3H,4H,6aH,9H,10H,11H,13H,14H,15bH-cycloundeca[e]isoindole-12,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.465   1.722   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.181   0.871   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.802   1.558   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.281  -0.757   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.548  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.292  -1.168   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.804  -1.459   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.804  -0.201   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.995  -2.987   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.505  -2.308   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.220  -4.144   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.929  -5.657   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.474  -6.161   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.691  -7.748   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.310  -5.153   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.855  -5.657   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.564  -7.169   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.109  -7.674   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.714  -9.218   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.944  -6.666   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.491  -7.375   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.235  -5.153   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.306  -3.925   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.368  -4.001   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.533  -2.931   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.003  -3.392   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.198  -1.428   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       1.187  -2.662   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       2.465  -3.014   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.619  -2.079   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.690  -4.649   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.981  -3.137   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.186  -1.580   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   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   31                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   16   22   32                                             
CONECT   32   31    5   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₉NO₅

Average Mass

457.6110 Da

Monoisotopic Mass

457.28282 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1N=C(O)[C@]23[C@H]1[C@H](C)C(C)=C[C@@H]2\C=C(C)\CC[C@@H](O)C(=O)C[C@@H](CC(C)=O)C3=O

InChI Identifier

InChI=1S/C27H39NO5/c1-14(2)9-21-24-18(6)16(4)11-20-10-15(3)7-8-22(30)23(31)13-19(12-17(5)29)25(32)27(20,24)26(33)28-21/h10-11,14,18-22,24,30H,7-9,12-13H2,1-6H3,(H,28,33)/b15-10+/t18-,19-,20+,21+,22-,24+,27+/m1/s1

InChI Key

JUCPANRNKTTWAB-GEPXZTCASA-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
Mariannaea elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspochalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears a 2-methylpropyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Aspochalasins

Direct Parent

Aspochalasins

Alternative Parents

Substituents

Aspochalasin skeleton
Carbocyclic aspochalasin skeleton
Isoindolone
Isoindoline
Isoindole
Isoindole or derivatives
Pyrrolidone
2-pyrrolidone
Pyrrolidine
Secondary carboxylic acid amide
Secondary alcohol
Cyclic ketone
Carboxamide group
Lactam
Ketone
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
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	2.82	ALOGPS
logS	-4.2	ALOGPS

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

27024268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44471186

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione (NP0151564)

MOL for NP0151564 ((3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione)

3D MOL for NP0151564 ((3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione)

3D SDF for NP0151564 ((3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione)

3D-SDF for NP0151564 ((3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione)

PDB for NP0151564 ((3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione)

3D PDB for NP0151564 ((3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione)

SMILES for NP0151564 ((3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione)

INCHI for NP0151564 ((3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione)

Structure for NP0151564 ((3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione)

3D Structure for NP0151564 ((3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-14-(2-oxopropyl)-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindole-12,15-dione)