NP-MRD: Showing NP-Card for 3'-Hydroxyrocaglamide (NP0137862)

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Record Information

Version

2.0

Created at

2022-05-31 16:36:49 UTC

Updated at

2022-05-31 16:36:49 UTC

NP-MRD ID

NP0137862

Secondary Accession Numbers

NP0076282

Natural Product Identification

Common Name

3'-Hydroxyrocaglamide

Description

3'-Hydroxyrocaglamide belongs to the class of organic compounds known as flavaglines. These are heterocyclic compounds with a structure characterized by a cyclopenta[b]benzofuran skeleton. Based on a literature review very few articles have been published on 3'-Hydroxyrocaglamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223252D          

 38 42  0  0  1  0            999 V2000
    5.2568    2.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282223252D          

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 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 35  1  0  0  0  0
  9 36  1  6  0  0  0
  2 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137862

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H31NO8/c1-30(2)27(33)23-24(16-9-7-6-8-10-16)29(17-11-12-20(36-4)19(31)13-17)28(34,26(23)32)25-21(37-5)14-18(35-3)15-22(25)38-29/h6-15,23-24,26,31-32,34H,1-5H3/t23-,24-,26-,28+,29+/m1/s1

> <INCHI_KEY>
VOSHNPGEFUCUHH-IDAMAFBJSA-N

> <FORMULA>
C29H31NO8

> <MOLECULAR_WEIGHT>
521.566

> <EXACT_MASS>
521.204966962

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.62099011209882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5S,6R)-2,3-dihydroxy-6-(3-hydroxy-4-methoxyphenyl)-10,12-dimethoxy-N,N-dimethyl-5-phenyl-7-oxatricyclo[6.4.0.0^{2,6}]dodeca-1(12),8,10-triene-4-carboxamide

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
2.0849662203333326

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.64199897879384

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.764367442272203

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6801910168971674

> <JCHEM_POLAR_SURFACE_AREA>
117.92000000000002

> <JCHEM_REFRACTIVITY>
138.24240000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S,6R)-2,3-dihydroxy-6-(3-hydroxy-4-methoxyphenyl)-10,12-dimethoxy-N,N-dimethyl-5-phenyl-7-oxatricyclo[6.4.0.0^{2,6}]dodeca-1(12),8,10-triene-4-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.813   4.829   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.260   3.355   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.207   2.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.707   2.581   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.260   4.055   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.313   5.179   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.866   6.652   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.919   7.776   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.720   4.085   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.216   2.630   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.444   1.701   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.676   2.661   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.229   4.134   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.493   5.015   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.523   6.554   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.774   4.639   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.610   3.631   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       1.484   6.151   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       0.029   6.656   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.648   7.159   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.413   1.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.543   0.246   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.280  -0.635   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.114   0.019   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.245   1.554   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.018   2.434   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.711   1.175   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.199   0.885   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.694  -0.570   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.702  -1.735   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.214  -1.444   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.719   0.011   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.197  -3.190   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.205  -4.354   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.345  -1.314   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       6.225   5.540   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      11.759   3.005   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.812   4.129   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   14   36                                             
CONECT   10    9   11   12   27                                             
CONECT   11   10    4                                                       
CONECT   12   10   13   21                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   12   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   10   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   30   34                                                       
CONECT   34   33                                                            
CONECT   35   29                                                            
CONECT   36    9                                                            
CONECT   37    2   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₁NO₈

Average Mass

521.5660 Da

Monoisotopic Mass

521.20497 Da

IUPAC Name

(2S,3R,4R,5S,6R)-2,3-dihydroxy-6-(3-hydroxy-4-methoxyphenyl)-10,12-dimethoxy-N,N-dimethyl-5-phenyl-7-oxatricyclo[6.4.0.0^{2,6}]dodeca-1(12),8,10-triene-4-carboxamide

Traditional Name

(2S,3R,4R,5S,6R)-2,3-dihydroxy-6-(3-hydroxy-4-methoxyphenyl)-10,12-dimethoxy-N,N-dimethyl-5-phenyl-7-oxatricyclo[6.4.0.0^{2,6}]dodeca-1(12),8,10-triene-4-carboxamide

CAS Registry Number

189322-67-6

SMILES

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

InChI Identifier

InChI=1S/C29H31NO8/c1-30(2)27(33)23-24(16-9-7-6-8-10-16)29(17-11-12-20(36-4)19(31)13-17)28(34,26(23)32)25-21(37-5)14-18(35-3)15-22(25)38-29/h6-15,23-24,26,31-32,34H,1-5H3/t23-,24-,26-,28+,29+/m1/s1

InChI Key

VOSHNPGEFUCUHH-IDAMAFBJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 flavaglines. These are heterocyclic compounds with a structure characterized by a cyclopenta[b]benzofuran skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Flavaglines

Direct Parent

Flavaglines

Alternative Parents

Substituents

Flavagline skeleton
Stilbene
Methoxyphenol
Coumaran
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Tertiary alcohol
Cyclic alcohol
1,2-diol
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Oxacycle
Ether
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen 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	3.29	ALOGPS
logP	2.08	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	138.24 m³·mol⁻¹	ChemAxon
Polarizability	54.62 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038671

Chemspider ID

8991152

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10815847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3'-Hydroxyrocaglamide (NP0137862)

MOL for NP0137862 (3'-Hydroxyrocaglamide)

3D MOL for NP0137862 (3'-Hydroxyrocaglamide)

3D SDF for NP0137862 (3'-Hydroxyrocaglamide)

3D-SDF for NP0137862 (3'-Hydroxyrocaglamide)

PDB for NP0137862 (3'-Hydroxyrocaglamide)

3D PDB for NP0137862 (3'-Hydroxyrocaglamide)

SMILES for NP0137862 (3'-Hydroxyrocaglamide)

INCHI for NP0137862 (3'-Hydroxyrocaglamide)

Structure for NP0137862 (3'-Hydroxyrocaglamide)

3D Structure for NP0137862 (3'-Hydroxyrocaglamide)