NP-MRD: Showing NP-Card for (+)-Yunnaneic acid C (NP0075909)

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Record Information

Version

2.0

Created at

2022-04-28 21:07:11 UTC

Updated at

2022-04-28 21:07:11 UTC

NP-MRD ID

NP0075909

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Yunnaneic acid C

Description

Yunnaneic acid C, also known as yunnaneate C, belongs to the class of organic compounds known as cyclohexylphenols. Cyclohexylphenols are compounds containing a cyclohexane lined to a phenol group. (+)-Yunnaneic acid C is found in Salvia yunnanensis. Based on a literature review very few articles have been published on Yunnaneic acid C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223072D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282223072D          

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M  END
> <DATABASE_ID>
NP0075909

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)\C=C\C1=C[C@@H]2[C@@H]([C@H]([C@H]1C(=O)C2=O)C(O)=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H22O12/c28-15-4-1-11(7-17(15)30)8-19(26(35)36)39-20(32)6-3-12-9-14-21(13-2-5-16(29)18(31)10-13)23(27(37)38)22(12)25(34)24(14)33/h1-7,9-10,14,19,21-23,28-31H,8H2,(H,35,36)(H,37,38)/b6-3+/t14-,19-,21+,22+,23-/m1/s1

> <INCHI_KEY>
LOTDZLWYGRUAKZ-BWAFDSPASA-N

> <FORMULA>
C27H22O12

> <MOLECULAR_WEIGHT>
538.461

> <EXACT_MASS>
538.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
50.35496227879586

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,4R)-6-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-3-(3,4-dihydroxyphenyl)-7,8-dioxobicyclo[2.2.2]oct-5-ene-2-carboxylic acid

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.9148581943333327

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.8019840916290595

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1533874573138547

> <JCHEM_PKA_STRONGEST_BASIC>
-6.2891616673888295

> <JCHEM_POLAR_SURFACE_AREA>
215.95999999999998

> <JCHEM_REFRACTIVITY>
132.4722

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,4R)-6-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-3-(3,4-dihydroxyphenyl)-7,8-dioxobicyclo[2.2.2]oct-5-ene-2-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      -9.124  -8.409   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.625  -6.953   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.615  -5.791   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.103  -6.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.602  -7.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.612  -8.703   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.111 -10.159   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.093  -4.922   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.581  -5.216   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.571  -4.054   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.059  -4.348   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.558  -5.804   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.049  -3.186   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.611  -1.552   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.037  -0.234   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.004   1.742   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.348   2.307   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.675   1.524   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.060   2.366   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.660  -0.016   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.006  -0.908   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.319  -0.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.586   0.251   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.595   1.278   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.065   1.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.851   2.342   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.381   2.168   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.995   0.756   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.080  -0.483   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.549  -0.309   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.694  -1.895   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.525   0.582   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.554   0.302   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.736  -1.484   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.470   1.694   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -4.080  -6.672   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.568  -6.966   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -5.090  -7.834   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -10.135  -9.571   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   36                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   24   33                                                  
CONECT   24   23   17   25                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29                                                            
CONECT   32   28                                                            
CONECT   33   23   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36    9   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
Yunnaneate C	Generator

Chemical Formula

C₂₇H₂₂O₁₂

Average Mass

538.4610 Da

Monoisotopic Mass

538.11113 Da

IUPAC Name

(1R,2R,3S,4R)-6-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-3-(3,4-dihydroxyphenyl)-7,8-dioxobicyclo[2.2.2]oct-5-ene-2-carboxylic acid

Traditional Name

(1R,2R,3S,4R)-6-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-3-(3,4-dihydroxyphenyl)-7,8-dioxobicyclo[2.2.2]oct-5-ene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)[C@@H](CC1=CC=C(O)C(O)=C1)OC(=O)\C=C\C1=C[C@@H]2[C@@H]([C@H]([C@H]1C(=O)C2=O)C(O)=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C27H22O12/c28-15-4-1-11(7-17(15)30)8-19(26(35)36)39-20(32)6-3-12-9-14-21(13-2-5-16(29)18(31)10-13)23(27(37)38)22(12)25(34)24(14)33/h1-7,9-10,14,19,21-23,28-31H,8H2,(H,35,36)(H,37,38)/b6-3+/t14-,19-,21+,22+,23-/m1/s1

InChI Key

LOTDZLWYGRUAKZ-BWAFDSPASA-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
Salvia Yunnanensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexylphenols. Cyclohexylphenols are compounds containing a cyclohexane lined to a phenol group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Cyclohexylphenols

Direct Parent

Cyclohexylphenols

Alternative Parents

Substituents

Cyclohexylphenol
3-phenylpropanoic-acid
Tricarboxylic acid or derivatives
Catechol
Cyclohexenone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Carboxylic acid
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.93	ALOGPS
logP	2.91	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	215.96 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.47 m³·mol⁻¹	ChemAxon
Polarizability	50.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

C00038029

Chemspider ID

8896476

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10721138

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Yunnaneic acid C (NP0075909)

MOL for NP0075909 ((+)-Yunnaneic acid C)

3D MOL for NP0075909 ((+)-Yunnaneic acid C)

3D SDF for NP0075909 ((+)-Yunnaneic acid C)

3D-SDF for NP0075909 ((+)-Yunnaneic acid C)

PDB for NP0075909 ((+)-Yunnaneic acid C)

3D PDB for NP0075909 ((+)-Yunnaneic acid C)

SMILES for NP0075909 ((+)-Yunnaneic acid C)

INCHI for NP0075909 ((+)-Yunnaneic acid C)

Structure for NP0075909 ((+)-Yunnaneic acid C)

3D Structure for NP0075909 ((+)-Yunnaneic acid C)