NP-MRD: Showing NP-Card for (2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one (NP0280814)

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Record Information

Version

2.0

Created at

2022-09-09 06:48:39 UTC

Updated at

2022-09-09 06:48:39 UTC

NP-MRD ID

NP0280814

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one

Description

3'-Hydroxymarikarin belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. (2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one was first documented in 2001 (PMID: 11336261). Based on a literature review very few articles have been published on 3'-Hydroxymarikarin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092208482D          

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M  END

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M  END


  Mrv1652309092208482D          

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  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 12 20  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  2  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  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  2  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 31 37  1  0  0  0  0
 29 38  1  0  0  0  0
  7 38  1  0  0  0  0
 11 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0280814

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(O[C@]3([C@@H](C4=C(N=C5CCCN5C4=O)[C@@]23O)C2=CC=CC=C2)C2=CC=C(OC)C(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H26N2O7/c1-37-18-14-20(34)26-22(15-18)39-30(17-10-11-21(38-2)19(33)13-17)25(16-7-4-3-5-8-16)24-27(29(26,30)36)31-23-9-6-12-32(23)28(24)35/h3-5,7-8,10-11,13-15,25,33-34,36H,6,9,12H2,1-2H3/t25-,29+,30+/m1/s1

> <INCHI_KEY>
HAZNVZZZKLUVIF-CPESWEKQSA-N

> <FORMULA>
C30H26N2O7

> <MOLECULAR_WEIGHT>
526.545

> <EXACT_MASS>
526.174001185

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
54.6757264513851

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,10R,11R)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0^{2,10}.0^{3,8}.0^{14,18}]nonadeca-1(12),3,5,7,18-pentaen-13-one

> <JCHEM_LOGP>
2.6819006436666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.018853314118525

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.41724491569406

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1067522834510934

> <JCHEM_POLAR_SURFACE_AREA>
121.05

> <JCHEM_REFRACTIVITY>
141.42380000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,10R,11R)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0^{2,10}.0^{3,8}.0^{14,18}]nonadeca-1(12),3,5,7,18-pentaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.471   0.679   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -7.100  -0.815   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.621  -1.241   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.512  -0.173   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.032  -0.599   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.923   0.470   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.661  -2.093   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.770  -3.162   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.250  -2.736   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.096  -4.547   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.571  -4.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.295  -5.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.834  -5.745   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.559  -7.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.744  -8.411   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.469  -9.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.008  -9.822   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.205  -8.359   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.390  -9.666   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.481  -7.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.212  -5.059   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.001  -6.584   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.428  -7.162   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.641  -8.688   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.426  -9.634   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.001  -9.056   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.214  -7.531   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.897  -3.990   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.223  -2.605   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       1.086  -1.329   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       2.622  -1.438   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       3.296  -2.823   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.433  -4.099   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.107  -5.484   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.821  -2.611   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.090  -1.094   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.731  -0.370   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.302  -2.818   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.033  -1.302   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   38                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   21   38                                             
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12                                                       
CONECT   21   11   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   21   29   33                                                  
CONECT   29   28   30   38                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   28   34                                                  
CONECT   34   33                                                            
CONECT   35   32   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   31                                                       
CONECT   38   29    7   11   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆N₂O₇

Average Mass

526.5450 Da

Monoisotopic Mass

526.17400 Da

IUPAC Name

(2S,10R,11R)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0^{2,10}.0^{3,8}.0^{14,18}]nonadeca-1(12),3,5,7,18-pentaen-13-one

Traditional Name

(2S,10R,11R)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0^{2,10}.0^{3,8}.0^{14,18}]nonadeca-1(12),3,5,7,18-pentaen-13-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(O[C@]3([C@@H](C4=C(N=C5CCCN5C4=O)[C@@]23O)C2=CC=CC=C2)C2=CC=C(OC)C(O)=C2)=C1

InChI Identifier

InChI=1S/C30H26N2O7/c1-37-18-14-20(34)26-22(15-18)39-30(17-10-11-21(38-2)19(33)13-17)25(16-7-4-3-5-8-16)24-27(29(26,30)36)31-23-9-6-12-32(23)28(24)35/h3-5,7-8,10-11,13-15,25,33-34,36H,6,9,12H2,1-2H3/t25-,29+,30+/m1/s1

InChI Key

HAZNVZZZKLUVIF-CPESWEKQSA-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 stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Methoxyphenol
Coumaran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyrimidone
Monocyclic benzene moiety
Pyrimidine
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Lactam
Azacycle
Oxacycle
Ether
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	2.68	ChemAxon
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.42 m³·mol⁻¹	ChemAxon
Polarizability	54.68 Å³	ChemAxon
Number of Rings	7	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

101141821

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Grege H, Pache T, Brem B, Bacher M, Hofer O: Insecticidal flavaglines and other compounds from Fijian Aglaia species. Phytochemistry. 2001 May;57(1):57-64. doi: 10.1016/s0031-9422(00)00471-4. [PubMed:11336261 ]
LOTUS database [Link]

Showing NP-Card for (2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one (NP0280814)

MOL for NP0280814 ((2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one)

3D MOL for NP0280814 ((2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one)

3D SDF for NP0280814 ((2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one)

3D-SDF for NP0280814 ((2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one)

PDB for NP0280814 ((2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one)

3D PDB for NP0280814 ((2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one)

SMILES for NP0280814 ((2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one)

INCHI for NP0280814 ((2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one)

Structure for NP0280814 ((2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one)

3D Structure for NP0280814 ((2s,10r,11r)-2,4-dihydroxy-10-(3-hydroxy-4-methoxyphenyl)-6-methoxy-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0²,¹⁰.0³,⁸.0¹⁴,¹⁸]nonadeca-1(12),3,5,7,18-pentaen-13-one)