NP-MRD: Showing NP-Card for 19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione (NP0316751)

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Record Information

Version

2.0

Created at

2022-09-11 16:09:21 UTC

Updated at

2022-09-11 16:09:21 UTC

NP-MRD ID

NP0316751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione

Description

19-Hydroxy-17-[(1H-indol-3-yl)methyl]-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]Nonadeca-9,18-diene-2,5-dione belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. 19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione is found in Pseudeurotium zonatum. 19-Hydroxy-17-[(1H-indol-3-yl)methyl]-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]Nonadeca-9,18-diene-2,5-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191520592D          

 35 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004191520592D          

 35 40  0  0  0  0            999 V2000
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 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 19 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  6 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CNC4=CC=CC=C34)NC(=O)C22C(C=CCC(C)CC(=O)CCC2=O)C2OC12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H34N2O4/c1-16-7-6-9-21-26-28(3,35-26)17(2)25-23(14-18-15-30-22-10-5-4-8-20(18)22)31-27(34)29(21,25)24(33)12-11-19(32)13-16/h4-6,8-10,15-17,21,23,25-26,30H,7,11-14H2,1-3H3,(H,31,34)

> <INCHI_KEY>
YGKUXRWMCOUTAL-UHFFFAOYSA-N

> <FORMULA>
C29H34N2O4

> <MOLECULAR_WEIGHT>
474.601

> <EXACT_MASS>
474.251857583

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.52569272912869

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
17-[(1H-indol-3-yl)methyl]-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadec-9-ene-2,5,19-trione

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
3.9188937856666675

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.072626498820064

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.239949199233699

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3813586571700105

> <JCHEM_POLAR_SURFACE_AREA>
91.56

> <JCHEM_REFRACTIVITY>
133.83599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-(1H-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadec-9-ene-2,5,19-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.819   2.518   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.893   1.257   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.656   2.594   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.164   2.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.333   0.750   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.541  -0.425   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.003   0.058   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.465   0.541   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.152  -0.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.756  -1.212   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.839  -2.474   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.043  -3.544   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.377  -2.957   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.758  -4.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.587  -5.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.771  -7.035   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.348  -8.462   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.169  -9.453   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.862  -8.637   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.382  -9.062   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.274  -7.993   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.646  -6.498   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.126  -6.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.234  -7.143   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       4.225  -4.214   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       4.287  -2.905   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.548  -2.422   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.228  -1.933   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.765  -2.416   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.723  -3.806   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.616  -1.391   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.154  -1.874   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.004  -0.849   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.531  -1.313   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.317   0.659   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   28                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   19                                                  
CONECT   25   14   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    6   13   29                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄N₂O₄

Average Mass

474.6010 Da

Monoisotopic Mass

474.25186 Da

IUPAC Name

17-[(1H-indol-3-yl)methyl]-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadec-9-ene-2,5,19-trione

Traditional Name

17-(1H-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadec-9-ene-2,5,19-trione

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CNC4=CC=CC=C34)NC(=O)C22C(C=CCC(C)CC(=O)CCC2=O)C2OC12C

InChI Identifier

InChI=1S/C29H34N2O4/c1-16-7-6-9-21-26-28(3,35-26)17(2)25-23(14-18-15-30-22-10-5-4-8-20(18)22)31-27(34)29(21,25)24(33)12-11-19(32)13-16/h4-6,8-10,15-17,21,23,25-26,30H,7,11-14H2,1-3H3,(H,31,34)

InChI Key

YGKUXRWMCOUTAL-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
Pseudeurotium zonatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Isoindole or derivatives
Oxepane
Substituted pyrrole
Benzenoid
Pyrrole
Pyrroline
Heteroaromatic compound
Cyclic carboximidic acid
Ketone
Cyclic ketone
Azacycle
Oxacycle
Ether
Oxirane
Dialkyl ether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen 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	4	ALOGPS
logP	3.92	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	14.24	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.84 m³·mol⁻¹	ChemAxon
Polarizability	52.53 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

78410066

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione (NP0316751)

MOL for NP0316751 (19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

3D MOL for NP0316751 (19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

3D SDF for NP0316751 (19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

3D-SDF for NP0316751 (19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

PDB for NP0316751 (19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

3D PDB for NP0316751 (19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

SMILES for NP0316751 (19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

INCHI for NP0316751 (19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

Structure for NP0316751 (19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

3D Structure for NP0316751 (19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)