NP-MRD: Showing NP-Card for dendrocandin c (NP0322443)

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Record Information

Version

2.0

Created at

2022-09-12 01:12:32 UTC

Updated at

2022-09-12 01:12:32 UTC

NP-MRD ID

NP0322443

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dendrocandin c

Description

Dendrocandin C 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. Dendrocandin C is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. dendrocandin c is found in Dendrobium moniliforme. dendrocandin c was first documented in 2009 (PMID: 19182417). Based on a literature review very few articles have been published on dendrocandin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.3957    2.9647   -0.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1703    2.3905    0.2512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0023    1.0594    0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    0.2605   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9364   -1.0610    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0205   -1.9753   -0.3742 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4110   -1.8343    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0443   -0.5471   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8740    0.4903    0.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4323    1.7365    0.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900    1.9844   -0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593    3.2595   -0.6736 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3859    0.9809   -1.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -0.2742   -1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064   -1.8469   -1.7612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4195   -3.0259   -2.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -1.5272    1.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6557   -0.7280    1.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4101   -1.2701    2.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039    0.5846    1.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062    1.4076    2.2601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264    2.6935   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089    4.0477   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6874    2.4876   -1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5004    0.6780   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3046   -3.0125   -0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3277   -1.9524    1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280   -2.6477   -0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    0.3593    1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2996    2.5580    1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070    3.9747    0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9873    1.1988   -2.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -1.0538   -1.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4443   -2.9373   -3.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4671   -3.2490   -2.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -3.9025   -2.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6556   -2.5626    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0917   -0.8086    3.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941    1.1002    3.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  6  5  1  0
  5 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 20  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
 14  8  1  0
  4  5  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
  6 26  1  6
  7 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 17 37  1  0
 19 38  1  0
 21 39  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
M  END


  Mrv1652309122203122D          

 21 22  0  0  1  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  6 15  1  6  0  0  0
 15 16  1  0  0  0  0
  5 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322443

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H](CC1=CC=C(O)C=C1)C1=CC(O)=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O5/c1-20-14(7-10-3-5-12(17)6-4-10)11-8-13(18)16(19)15(9-11)21-2/h3-6,8-9,14,17-19H,7H2,1-2H3/t14-/m0/s1

> <INCHI_KEY>
NETURQQBHBZIMJ-AWEZNQCLSA-N

> <FORMULA>
C16H18O5

> <MOLECULAR_WEIGHT>
290.315

> <EXACT_MASS>
290.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.607863270118564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1S)-2-(4-hydroxyphenyl)-1-methoxyethyl]-3-methoxybenzene-1,2-diol

> <JCHEM_LOGP>
2.8535567139999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.239352870514871

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.33664800459975

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0853183346014985

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
79.0688

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S)-2-(4-hydroxyphenyl)-1-methoxyethyl]-3-methoxybenzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    6   16                                                       
CONECT   16   15                                                            
CONECT   17    5   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    3   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
(S)-3,4,4'-Trihydroxy-5,alpha-dimethoxybibenzyl	ChEBI
(S)-3,4,4'-Trihydroxy-5,a-dimethoxybibenzyl	Generator
(S)-3,4,4'-Trihydroxy-5,α-dimethoxybibenzyl	Generator

Chemical Formula

C₁₆H₁₈O₅

Average Mass

290.3150 Da

Monoisotopic Mass

290.11542 Da

IUPAC Name

5-[(1S)-2-(4-hydroxyphenyl)-1-methoxyethyl]-3-methoxybenzene-1,2-diol

Traditional Name

5-[(1S)-2-(4-hydroxyphenyl)-1-methoxyethyl]-3-methoxybenzene-1,2-diol

CAS Registry Number

Not Available

SMILES

CO[C@@H](CC1=CC=C(O)C=C1)C1=CC(O)=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C16H18O5/c1-20-14(7-10-3-5-12(17)6-4-10)11-8-13(18)16(19)15(9-11)21-2/h3-6,8-9,14,17-19H,7H2,1-2H3/t14-/m0/s1

InChI Key

NETURQQBHBZIMJ-AWEZNQCLSA-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
Dendrobium moniliforme	LOTUS Database	35616633

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
Benzylether
Anisole
Phenoxy compound
Catechol
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ether
Dialkyl ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:65743 )
methoxybenzene (CHEBI:65743 )
diphenylethane (CHEBI:65743 )

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	2.85	ChemAxon
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.07 m³·mol⁻¹	ChemAxon
Polarizability	30.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

28286004

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25208514

PDB ID

Not Available

ChEBI ID

65743

Good Scents ID

Not Available

References

General References

Li Y, Wang CL, Wang YJ, Guo SX, Yang JS, Chen XM, Xiao PG: Three new bibenzyl derivatives from Dendrobium candidum. Chem Pharm Bull (Tokyo). 2009 Feb;57(2):218-9. doi: 10.1248/cpb.57.218. [PubMed:19182417 ]
LOTUS database [Link]

Showing NP-Card for dendrocandin c (NP0322443)

MOL for NP0322443 (dendrocandin c)

3D MOL for NP0322443 (dendrocandin c)

3D SDF for NP0322443 (dendrocandin c)

3D-SDF for NP0322443 (dendrocandin c)

PDB for NP0322443 (dendrocandin c)

3D PDB for NP0322443 (dendrocandin c)

SMILES for NP0322443 (dendrocandin c)

INCHI for NP0322443 (dendrocandin c)

Structure for NP0322443 (dendrocandin c)

3D Structure for NP0322443 (dendrocandin c)