NP-MRD: Showing NP-Card for 3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one (NP0188023)

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Record Information

Version

2.0

Created at

2022-09-04 04:17:06 UTC

Updated at

2022-09-04 04:17:07 UTC

NP-MRD ID

NP0188023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one

Description

3,9-Dihydroxy-5-[(1H-indol-3-yl)methyl]-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]Henicosa-1(20),3,11,15,18-pentaen-17-one belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. 3,9-Dihydroxy-5-[(1H-indol-3-yl)methyl]-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]Henicosa-1(20),3,11,15,18-pentaen-17-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181500262D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004181500262D          

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    1.3884   -0.1724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6680   -0.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3007   -1.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4773   -1.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568   -2.2347    0.0000 C   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
  4  3  1  4  0  0  0
  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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 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
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37  2  1  4  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CNC4=CC=CC=C34)NC(=O)C22C(C=CCC(C)C=C(C)C(=O)C3=CC=C2N3)C(O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C32H35N3O3/c1-17-8-7-10-23-30(37)20(4)19(3)28-26(15-21-16-33-24-11-6-5-9-22(21)24)35-31(38)32(23,28)27-13-12-25(34-27)29(36)18(2)14-17/h5-7,9-14,16-17,19,23,26,28,30,33-34,37H,4,8,15H2,1-3H3,(H,35,38)

> <INCHI_KEY>
CYRVQOQBMLPFPT-UHFFFAOYSA-N

> <FORMULA>
C32H35N3O3

> <MOLECULAR_WEIGHT>
509.65

> <EXACT_MASS>
509.267841999

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.08280490165724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-hydroxy-5-[(1H-indol-3-yl)methyl]-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),11,15,18-tetraene-3,17-dione

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
4.342318271333334

> <ALOGPS_LOGS>
-5.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.095881300754336

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.91584769089647

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5875380984524758

> <JCHEM_POLAR_SURFACE_AREA>
97.97999999999999

> <JCHEM_REFRACTIVITY>
150.94580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-5-(1H-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),11,15,18-tetraene-3,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       2.923  -5.646   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.072  -4.363   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.535  -4.459   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.316  -3.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.369  -1.796   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.482  -0.513   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.019  -0.609   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.705  -1.988   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.871   0.674   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.408   0.579   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.185   2.053   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.036   3.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.648   2.149   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.309   3.355   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.104   4.839   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.974   5.938   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.718   7.457   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       2.084   8.170   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.183   7.091   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.720   7.187   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.572   5.904   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.886   4.525   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.349   4.429   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.498   5.712   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       1.752   2.818   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       1.618   1.485   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.893   0.322   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.203   0.866   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.740   0.961   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.819   2.061   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.198   1.375   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.129  -0.226   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       2.592  -0.322   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       4.980  -1.509   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.517  -1.414   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.295  -2.888   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.758  -2.984   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.146  -4.172   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
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                                                            
CONECT    9    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   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32   29                                                       
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36    2                                                       
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₅N₃O₃

Average Mass

509.6500 Da

Monoisotopic Mass

509.26784 Da

IUPAC Name

9-hydroxy-5-[(1H-indol-3-yl)methyl]-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),11,15,18-tetraene-3,17-dione

Traditional Name

9-hydroxy-5-(1H-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),11,15,18-tetraene-3,17-dione

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CNC4=CC=CC=C34)NC(=O)C22C(C=CCC(C)C=C(C)C(=O)C3=CC=C2N3)C(O)C1=C

InChI Identifier

InChI=1S/C32H35N3O3/c1-17-8-7-10-23-30(37)20(4)19(3)28-26(15-21-16-33-24-11-6-5-9-22(21)24)35-31(38)32(23,28)27-13-12-25(34-27)29(36)18(2)14-17/h5-7,9-14,16-17,19,23,26,28,30,33-34,37H,4,8,15H2,1-3H3,(H,35,38)

InChI Key

CYRVQOQBMLPFPT-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
Isoindolone
3-alkylindole
Indole
Indole or derivatives
Isoindoline
Isoindole or derivatives
Aryl ketone
Pyrrolidone
Benzenoid
2-pyrrolidone
Substituted pyrrole
Cyclic alcohol
Heteroaromatic compound
Pyrrole
Pyrrolidine
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Ketone
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organonitrogen compound
Organooxygen 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	4.71	ALOGPS
logP	4.34	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	12.92	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	150.95 m³·mol⁻¹	ChemAxon
Polarizability	57.08 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

73836031

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one (NP0188023)

MOL for NP0188023 (3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one)

3D MOL for NP0188023 (3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one)

3D SDF for NP0188023 (3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one)

3D-SDF for NP0188023 (3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one)

PDB for NP0188023 (3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one)

3D PDB for NP0188023 (3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one)

SMILES for NP0188023 (3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one)

INCHI for NP0188023 (3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one)

Structure for NP0188023 (3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one)

3D Structure for NP0188023 (3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,11,15,18-pentaen-17-one)