NP-MRD: Showing NP-Card for Okaramine K (NP0068846)

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Record Information

Version

2.0

Created at

2022-04-28 14:05:34 UTC

Updated at

2022-04-28 14:05:35 UTC

NP-MRD ID

NP0068846

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Okaramine K

Description

Okaramine K_120152 belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Okaramine K is found in Aspergillus aculeatus. Based on a literature review very few articles have been published on Okaramine K_120152.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216052D          

 39 44  0  0  1  0            999 V2000
    5.0403    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2884    1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3524    0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5275    0.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1008   -0.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282216052D          

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  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  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  2  0  0  0  0
 11 12  1  0  0  0  0
  7 12  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 20  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 25 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0068846

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC=CC2=C1N[C@@H]1N3[C@@H](C[C@]21O)C(=O)N\C(=C/C1=C(NC2=CC=CC=C12)C(C)(C)C=C)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H34N4O3/c1-6-31(4,5)27-21(20-11-7-8-13-23(20)33-27)16-24-29(38)36-25(28(37)34-24)17-32(39)22-12-9-10-19(15-14-18(2)3)26(22)35-30(32)36/h6-14,16,25,30,33,35,39H,1,15,17H2,2-5H3,(H,34,37)/b24-16-/t25-,30+,32-/m0/s1

> <INCHI_KEY>
JSBSVMCRQHPARV-MFWIRICFSA-N

> <FORMULA>
C32H34N4O3

> <MOLECULAR_WEIGHT>
522.649

> <EXACT_MASS>
522.263090971

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.827471305210835

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4Z,7S,9S)-9-hydroxy-14-(3-methylbut-2-en-1-yl)-4-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10(15),11,13-triene-3,6-dione

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
4.3192291030000005

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.958900969408859

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.726148774584704

> <JCHEM_PKA_STRONGEST_BASIC>
0.16322117994725627

> <JCHEM_POLAR_SURFACE_AREA>
97.46000000000001

> <JCHEM_REFRACTIVITY>
155.7717

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4Z,7S,9S)-9-hydroxy-14-(3-methylbut-2-en-1-yl)-4-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10(15),11,13-triene-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  N   UNK     0       9.409   0.265   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       9.119   1.777   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.284   2.784   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.738   2.279   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.002   3.159   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      14.230   2.229   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      13.724   0.774   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.185   0.805   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.388  -0.513   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.131  -1.861   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.671  -1.892   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.467  -0.575   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.033   4.699   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.064   6.239   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.494   4.730   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.751   6.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.573   4.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.664   2.282   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.374   3.795   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       6.499   1.275   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       6.789  -0.237   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.244  -0.742   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.533  -2.255   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.440  -0.980   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.316   0.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.971   1.467   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       3.848   2.520   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       2.499   1.777   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.788   0.265   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.624  -0.742   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.169  -0.237   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.121   1.275   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.044   2.282   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.754   3.795   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.701   4.300   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.991   5.813   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.445   6.318   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.174   6.820   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.662  -1.321   0.000  0.00  0.00           O+0
CONECT    1    2   22                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    4    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    5   14   15   17                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   13                                                            
CONECT   18    2   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21    1   23                                                  
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   29   39                                             
CONECT   26   25   20   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   25   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   25                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₄N₄O₃

Average Mass

522.6490 Da

Monoisotopic Mass

522.26309 Da

IUPAC Name

(1R,4Z,7S,9S)-9-hydroxy-14-(3-methylbut-2-en-1-yl)-4-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10(15),11,13-triene-3,6-dione

Traditional Name

(1R,4Z,7S,9S)-9-hydroxy-14-(3-methylbut-2-en-1-yl)-4-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-10(15),11,13-triene-3,6-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=CC=CC2=C1N[C@@H]1N3[C@@H](C[C@]21O)C(=O)N\C(=C/C1=C(NC2=CC=CC=C12)C(C)(C)C=C)C3=O

InChI Identifier

InChI=1S/C32H34N4O3/c1-6-31(4,5)27-21(20-11-7-8-13-23(20)33-27)16-24-29(38)36-25(28(37)34-24)17-32(39)22-12-9-10-19(15-14-18(2)3)26(22)35-30(32)36/h6-14,16,25,30,33,35,39H,1,15,17H2,2-5H3,(H,34,37)/b24-16-/t25-,30+,32-/m0/s1

InChI Key

JSBSVMCRQHPARV-MFWIRICFSA-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
Aspergillus aculeatus	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Indole
Dihydroindole
Dioxopiperazine
2,5-dioxopiperazine
Secondary aliphatic/aromatic amine
N-alkylpiperazine
1,4-diazinane
Piperazine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Tertiary alcohol
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Lactam
Secondary amine
Azacycle
Carboxylic acid derivative
Amine
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic oxide
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
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	4.95	ALOGPS
logP	4.32	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	11.73	ChemAxon
pKa (Strongest Basic)	0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	155.77 m³·mol⁻¹	ChemAxon
Polarizability	56.83 Å³	ChemAxon
Number of Rings	6	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

100990551

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Okaramine K (NP0068846)

MOL for NP0068846 (Okaramine K)

3D MOL for NP0068846 (Okaramine K)

3D SDF for NP0068846 (Okaramine K)

3D-SDF for NP0068846 (Okaramine K)

PDB for NP0068846 (Okaramine K)

3D PDB for NP0068846 (Okaramine K)

SMILES for NP0068846 (Okaramine K)

INCHI for NP0068846 (Okaramine K)

Structure for NP0068846 (Okaramine K)

3D Structure for NP0068846 (Okaramine K)