NP-MRD: Showing NP-Card for 16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0199356)

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Record Information

Version

2.0

Created at

2022-09-04 17:59:17 UTC

Updated at

2022-09-04 17:59:17 UTC

NP-MRD ID

NP0199356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

Description

16-Acetyl-6-hydroxy-4-[(1H-indol-3-yl)methyl]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-5,10,12,14-tetraen-3-one 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. 16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one is found in Penicillium simplicissimum. 16-Acetyl-6-hydroxy-4-[(1H-indol-3-yl)methyl]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-5,10,12,14-tetraen-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241515212D          

 36 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241515212D          

 36 41  0  0  0  0            999 V2000
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  4 15  1  0  0  0  0
 10 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
  7 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  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
 24 35  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0199356

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N1C2N3C(CC2(C2=CC=CC=C12)C(C)(C)C=C)C(=O)NC(CC1=CNC2=CC=CC=C12)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H30N4O3/c1-5-28(3,4)29-15-24-25(35)31-22(14-18-16-30-21-12-8-6-10-19(18)21)26(36)33(24)27(29)32(17(2)34)23-13-9-7-11-20(23)29/h5-13,16,22,24,27,30H,1,14-15H2,2-4H3,(H,31,35)

> <INCHI_KEY>
YFVVHZDKGOWDHW-UHFFFAOYSA-N

> <FORMULA>
C29H30N4O3

> <MOLECULAR_WEIGHT>
482.584

> <EXACT_MASS>
482.231790842

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.58636000806164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-acetyl-4-[(1H-indol-3-yl)methyl]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
3.2598387156666675

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.147153418763445

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.279695009584366

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888623983340925

> <JCHEM_POLAR_SURFACE_AREA>
85.50999999999999

> <JCHEM_REFRACTIVITY>
135.97140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-acetyl-4-(1H-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

> <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       3.249 -20.099   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.154 -18.853   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.528 -17.446   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.686 -19.014   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.716 -17.869   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.877 -16.338   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.384 -16.018   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.154 -17.351   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.123 -18.496   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.962 -20.027   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.993 -21.172   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.517 -22.636   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.010 -22.956   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.980 -21.812   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.456 -20.347   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.530 -19.122   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.156 -17.715   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.904 -20.529   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.937 -19.748   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.098 -21.280   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.860 -14.553   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.366 -14.233   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       7.829 -13.408   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       6.323 -13.729   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.292 -12.584   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.768 -11.120   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.863  -9.874   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       5.768  -8.628   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       7.233  -9.104   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.566  -8.334   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.900  -9.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.900 -10.644   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.566 -11.414   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.233 -10.644   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.847 -15.193   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.340 -15.513   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   15                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7   35                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5   10   16                                             
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    4   10                                                  
CONECT   16    9   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19                                                            
CONECT   21    7   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    6   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₀N₄O₃

Average Mass

482.5840 Da

Monoisotopic Mass

482.23179 Da

IUPAC Name

16-acetyl-4-[(1H-indol-3-yl)methyl]-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

Traditional Name

16-acetyl-4-(1H-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

CAS Registry Number

Not Available

SMILES

CC(=O)N1C2N3C(CC2(C2=CC=CC=C12)C(C)(C)C=C)C(=O)NC(CC1=CNC2=CC=CC=C12)C3=O

InChI Identifier

InChI=1S/C29H30N4O3/c1-5-28(3,4)29-15-24-25(35)31-22(14-18-16-30-21-12-8-6-10-19(18)21)26(36)33(24)27(29)32(17(2)34)23-13-9-7-11-20(23)29/h5-13,16,22,24,27,30H,1,14-15H2,2-4H3,(H,31,35)

InChI Key

YFVVHZDKGOWDHW-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
Penicillium simplicissimum	LOTUS Database	35616633

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
3-alkylindole
Indole
Substituted pyrrole
Benzenoid
Pyrrole
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Cyclic carboximidic acid
Acetamide
Lactam
Carboxamide group
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
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	3.42	ALOGPS
logP	3.26	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	11.28	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135.97 m³·mol⁻¹	ChemAxon
Polarizability	50.59 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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 16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0199356)

MOL for NP0199356 (16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D MOL for NP0199356 (16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D SDF for NP0199356 (16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D-SDF for NP0199356 (16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

PDB for NP0199356 (16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D PDB for NP0199356 (16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

SMILES for NP0199356 (16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

INCHI for NP0199356 (16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

Structure for NP0199356 (16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D Structure for NP0199356 (16-acetyl-6-hydroxy-4-(1h-indol-3-ylmethyl)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)