NP-MRD: Showing NP-Card for 3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one (NP0246897)

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Record Information

Version

2.0

Created at

2022-09-07 08:30:53 UTC

Updated at

2022-09-07 08:30:53 UTC

NP-MRD ID

NP0246897

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one

Description

3-Hydroxy-5-[(1H-indol-3-yl)methyl]-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]Docosa-1(22),3,12,16-tetraen-18-one 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. 3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one is found in Ulva intestinalis. 3-Hydroxy-5-[(1H-indol-3-yl)methyl]-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]Docosa-1(22),3,12,16-tetraen-18-one is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261513172D          

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M  END

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M  END


  Mrv1533004261513172D          

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    1.3200   -0.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6571   -0.9452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4778   -1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6549   -0.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9864    0.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149   -1.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -1.8672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314   -2.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5107   -2.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6685   -3.2041    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
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  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  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 31 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>
NP0246897

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CNC4=CC=CC=C34)NC(=O)C22C(C=CCC(C)C=C(C)C(=O)C3CCC2=N3)C2OC12C

> <INCHI_IDENTIFIER>
InChI=1S/C32H37N3O3/c1-17-8-7-10-22-29-31(4,38-29)19(3)27-25(15-20-16-33-23-11-6-5-9-21(20)23)35-30(37)32(22,27)26-13-12-24(34-26)28(36)18(2)14-17/h5-7,9-11,14,16-17,19,22,24-25,27,29,33H,8,12-13,15H2,1-4H3,(H,35,37)

> <INCHI_KEY>
UJPWZJUBKFMAST-UHFFFAOYSA-N

> <FORMULA>
C32H37N3O3

> <MOLECULAR_WEIGHT>
511.666

> <EXACT_MASS>
511.283492063

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
57.191058874083524

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(1H-indol-3-yl)methyl]-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),12,16-triene-3,18-dione

> <ALOGPS_LOGP>
4.91

> <JCHEM_LOGP>
5.085253821666667

> <ALOGPS_LOGS>
-5.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.165626766442674

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.322558872213257

> <JCHEM_PKA_STRONGEST_BASIC>
4.079469658446196

> <JCHEM_POLAR_SURFACE_AREA>
86.85

> <JCHEM_REFRACTIVITY>
148.6731

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(1H-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),12,16-triene-3,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       2.547  -7.071   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.917  -5.665   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.386  -5.508   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.244  -4.102   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.659  -2.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.030  -1.449   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.502  -1.291   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.034  -1.133   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.132   0.114   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.379   1.017   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.229   1.362   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.858   2.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.303   1.204   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.445   2.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.281   3.769   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.525   4.676   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.522   6.216   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.985   6.695   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       4.893   5.451   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.425   5.294   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.054   3.888   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.152   2.640   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.620   2.798   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.990   4.204   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       2.780   1.470   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       2.429   0.178   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.496  -1.179   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.932  -0.201   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.464  -0.359   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       3.093  -1.764   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       4.625  -1.922   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.956  -0.354   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.708   0.549   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.255  -3.328   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.786  -3.485   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.352  -4.575   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.820  -4.418   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.981  -5.981   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    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   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   29                                                       
CONECT   34   31   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   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₇N₃O₃

Average Mass

511.6660 Da

Monoisotopic Mass

511.28349 Da

IUPAC Name

5-[(1H-indol-3-yl)methyl]-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),12,16-triene-3,18-dione

Traditional Name

5-(1H-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),12,16-triene-3,18-dione

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CNC4=CC=CC=C34)NC(=O)C22C(C=CCC(C)C=C(C)C(=O)C3CCC2=N3)C2OC12C

InChI Identifier

InChI=1S/C32H37N3O3/c1-17-8-7-10-22-29-31(4,38-29)19(3)27-25(15-20-16-33-23-11-6-5-9-21(20)23)35-30(37)32(22,27)26-13-12-24(34-26)28(36)18(2)14-17/h5-7,9-11,14,16-17,19,22,24-25,27,29,33H,8,12-13,15H2,1-4H3,(H,35,37)

InChI Key

UJPWZJUBKFMAST-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
Ulva intestinalis	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
Ketimine
Ketone
Azacycle
Oxacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Dialkyl ether
Oxirane
Ether
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Imine
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
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	4.91	ALOGPS
logP	5.09	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	14.32	ChemAxon
pKa (Strongest Basic)	4.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.85 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	148.67 m³·mol⁻¹	ChemAxon
Polarizability	57.19 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

73837052

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one (NP0246897)

MOL for NP0246897 (3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one)

3D MOL for NP0246897 (3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one)

3D SDF for NP0246897 (3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one)

3D-SDF for NP0246897 (3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one)

PDB for NP0246897 (3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one)

3D PDB for NP0246897 (3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one)

SMILES for NP0246897 (3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one)

INCHI for NP0246897 (3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one)

Structure for NP0246897 (3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one)

3D Structure for NP0246897 (3-hydroxy-5-(1h-indol-3-ylmethyl)-7,8,15,17-tetramethyl-9-oxa-4,22-diazapentacyclo[17.2.1.0²,⁶.0²,¹¹.0⁸,¹⁰]docosa-1(22),3,12,16-tetraen-18-one)