NP-MRD: Showing NP-Card for 3'-Hydroxy rocagloic acid (NP0070759)

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Record Information

Version

2.0

Created at

2022-04-28 16:12:06 UTC

Updated at

2022-04-28 16:12:06 UTC

NP-MRD ID

NP0070759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-Hydroxy rocagloic acid

Description

3'-Hydroxyrocagloic acid belongs to the class of organic compounds known as flavaglines. These are heterocyclic compounds with a structure characterized by a cyclopenta[b]benzofuran skeleton. 3'-Hydroxy rocagloic acid is found in Aglaia cucullata and Amoora cucullata . Based on a literature review very few articles have been published on 3'-Hydroxyrocagloic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218122D          

 36 40  0  0  1  0            999 V2000
    0.7719   -1.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5324   -0.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924   -0.9561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5628   -1.7356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0950   -2.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876   -1.7193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6270   -0.9298    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9502   -0.4581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9339    0.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4065   -0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621    0.1507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0303   -1.1993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0645   -2.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9944   -3.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6713   -3.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4182   -3.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4210    1.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
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  7 10  1  1  0  0  0
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  6 13  1  6  0  0  0
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  4 19  1  6  0  0  0
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M  END

     RDKit          3D

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   -4.8418   -3.7519   -1.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282218122D          

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M  END
> <DATABASE_ID>
NP0070759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(OC)=C1)[C@]1(O)[C@H](O)[C@@H]([C@@H](C3=CC=CC=C3)[C@@]1(O2)C1=CC=C(OC)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O9/c1-33-16-12-19(35-3)23-20(13-16)36-27(15-9-10-18(34-2)17(28)11-15)22(14-7-5-4-6-8-14)21(25(30)31)24(29)26(23,27)32/h4-13,21-22,24,28-29,32H,1-3H3,(H,30,31)/t21-,22-,24-,26+,27+/m1/s1

> <INCHI_KEY>
AOUWJEQQNZVCAQ-PXIJUOARSA-N

> <FORMULA>
C27H26O9

> <MOLECULAR_WEIGHT>
494.496

> <EXACT_MASS>
494.157682417

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
49.99998085621789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <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-5-phenyl-7-oxatricyclo[6.4.0.0^{2,6}]dodeca-1(8),9,11-triene-4-carboxylic acid

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
2.4445567026666666

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.764899326730987

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.459322476837911

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5728460003165123

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
126.6268

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S,6R)-2,3-dihydroxy-6-(3-hydroxy-4-methoxyphenyl)-10,12-dimethoxy-5-phenyl-7-oxatricyclo[6.4.0.0^{2,6}]dodeca-1(8),9,11-triene-4-carboxylic acid

> <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       1.441  -3.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.994  -1.815   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.546  -1.785   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.050  -3.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.177  -4.169   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.590  -3.209   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.037  -1.736   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.774  -0.855   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.743   0.684   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.492  -1.231   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.782   0.281   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.657  -2.239   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.854  -4.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.723  -5.624   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.986  -6.505   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.381  -5.851   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.511  -4.316   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.248  -3.436   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.555  -4.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.547  -5.859   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.052  -7.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.564  -7.605   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.572  -6.440   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.068  -4.985   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.921  -7.184   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.069  -9.060   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.061 -10.224   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.041  -0.330   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.047  -0.691   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.546  -1.041   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.993  -2.515   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.941  -3.639   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.493  -2.865   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.546  -1.741   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.600   0.782   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.653   1.906   0.000  0.00  0.00           C+0
CONECT    1    2    5   32                                                  
CONECT    2    1    3   29                                                  
CONECT    3    2    4    8   28                                             
CONECT    4    3    5    6   19                                             
CONECT    5    4    1                                                       
CONECT    6    4    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    6   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    4   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26   22   27                                                       
CONECT   27   26                                                            
CONECT   28    3                                                            
CONECT   29    2   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31    1                                                       
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   29   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
3'-Hydroxyrocagloate	Generator

Chemical Formula

C₂₇H₂₆O₉

Average Mass

494.4960 Da

Monoisotopic Mass

494.15768 Da

IUPAC Name

(2S,3R,4R,5S,6R)-2,3-dihydroxy-6-(3-hydroxy-4-methoxyphenyl)-10,12-dimethoxy-5-phenyl-7-oxatricyclo[6.4.0.0^{2,6}]dodeca-1(8),9,11-triene-4-carboxylic acid

Traditional Name

(2S,3R,4R,5S,6R)-2,3-dihydroxy-6-(3-hydroxy-4-methoxyphenyl)-10,12-dimethoxy-5-phenyl-7-oxatricyclo[6.4.0.0^{2,6}]dodeca-1(8),9,11-triene-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC)=C1)[C@]1(O)[C@H](O)[C@@H]([C@@H](C3=CC=CC=C3)[C@@]1(O2)C1=CC=C(OC)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C27H26O9/c1-33-16-12-19(35-3)23-20(13-16)36-27(15-9-10-18(34-2)17(28)11-15)22(14-7-5-4-6-8-14)21(25(30)31)24(29)26(23,27)32/h4-13,21-22,24,28-29,32H,1-3H3,(H,30,31)/t21-,22-,24-,26+,27+/m1/s1

InChI Key

AOUWJEQQNZVCAQ-PXIJUOARSA-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

Species Name	Source	Reference
Aglaia cucullata	LOTUS Database	35616633
Amoora cucullata	Plant	KNApSAcK

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
Beta-hydroxy acid
Phenol
Alkyl aryl ether
Hydroxy acid
Benzenoid
Monocyclic benzene moiety
Cyclic alcohol
Tertiary alcohol
1,2-diol
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
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	3.36	ALOGPS
logP	2.44	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.63 m³·mol⁻¹	ChemAxon
Polarizability	50 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

Chemspider ID

17246891

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16088264

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3'-Hydroxy rocagloic acid (NP0070759)

MOL for NP0070759 (3'-Hydroxy rocagloic acid)

3D MOL for NP0070759 (3'-Hydroxy rocagloic acid)

3D SDF for NP0070759 (3'-Hydroxy rocagloic acid)

3D-SDF for NP0070759 (3'-Hydroxy rocagloic acid)

PDB for NP0070759 (3'-Hydroxy rocagloic acid)

3D PDB for NP0070759 (3'-Hydroxy rocagloic acid)

SMILES for NP0070759 (3'-Hydroxy rocagloic acid)

INCHI for NP0070759 (3'-Hydroxy rocagloic acid)

Structure for NP0070759 (3'-Hydroxy rocagloic acid)

3D Structure for NP0070759 (3'-Hydroxy rocagloic acid)