NP-MRD: Showing NP-Card for buddlenol b (NP0195462)

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Record Information

Version

2.0

Created at

2022-09-04 13:19:43 UTC

Updated at

2022-09-04 13:19:43 UTC

NP-MRD ID

NP0195462

Secondary Accession Numbers

None

Natural Product Identification

Common Name

buddlenol b

Description

Buddlenol B, also known as g(8-O-4)S(8-5)g, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Buddlenol B 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. buddlenol b is found in Arabidopsis thaliana, Buddleja davidii, Ehretia ovalifolia, Euonymus alatus and Populus tremula. buddlenol b was first documented in 2014 (PMID: 24660448). Based on a literature review very few articles have been published on buddlenol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215192D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042215192D          

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    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2962   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1212   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5337   -2.8414    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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 35  1  0  0  0  0
 35 36  2  0  0  0  0
 12 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
  5 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195462

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(C(CO)C2=CC(\C=C\CO)=C1)C1=CC(OC)=C(OC(CO)C(O)C2=CC=C(O)C(OC)=C2)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H36O11/c1-37-23-12-18(7-8-22(23)35)28(36)27(16-34)41-31-25(39-3)13-19(14-26(31)40-4)29-21(15-33)20-10-17(6-5-9-32)11-24(38-2)30(20)42-29/h5-8,10-14,21,27-29,32-36H,9,15-16H2,1-4H3/b6-5+

> <INCHI_KEY>
LCXGTSCVCJANHX-AATRIKPKSA-N

> <FORMULA>
C31H36O11

> <MOLECULAR_WEIGHT>
584.618

> <EXACT_MASS>
584.225761979

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
62.0705070597912

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(4-hydroxy-3-methoxyphenyl)-2-{4-[3-(hydroxymethyl)-5-[(1E)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy}propane-1,3-diol

> <JCHEM_LOGP>
1.8240016700000004

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.431653845828126

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908702583045766

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5263668573015536

> <JCHEM_POLAR_SURFACE_AREA>
156.53

> <JCHEM_REFRACTIVITY>
154.3841

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-hydroxy-3-methoxyphenyl)-2-{4-[3-(hydroxymethyl)-5-[(1E)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy}propane-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0     -12.640  -3.970   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -11.870  -2.637   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -10.330  -2.637   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.560  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.020  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.250   0.031   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.020   1.365   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.710   0.031   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.940   1.365   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.710   2.698   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.940  -1.303   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.400   1.365   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.630   2.698   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.259  -4.383   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.400  -3.970   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -4.940  -3.970   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.250  -2.637   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -8.020  -3.970   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -9.560  -3.970   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0     -10.330  -5.304   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   39                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   36                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   35                                                  
CONECT   18   17   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   31                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   25   31                                                       
CONECT   31   30   20   32                                                  
CONECT   32   31   18   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   17   36                                                       
CONECT   36   35   12   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39    5   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40    3   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
g(8-O-4)S(8-5)g	ChEBI

Chemical Formula

C₃₁H₃₆O₁₁

Average Mass

584.6180 Da

Monoisotopic Mass

584.22576 Da

IUPAC Name

1-(4-hydroxy-3-methoxyphenyl)-2-{4-[3-(hydroxymethyl)-5-[(1E)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy}propane-1,3-diol

Traditional Name

1-(4-hydroxy-3-methoxyphenyl)-2-{4-[3-(hydroxymethyl)-5-[(1E)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy}propane-1,3-diol

CAS Registry Number

Not Available

SMILES

COC1=C2OC(C(CO)C2=CC(\C=C\CO)=C1)C1=CC(OC)=C(OC(CO)C(O)C2=CC=C(O)C(OC)=C2)C(OC)=C1

InChI Identifier

InChI=1S/C31H36O11/c1-37-23-12-18(7-8-22(23)35)28(36)27(16-34)41-31-25(39-3)13-19(14-26(31)40-4)29-21(15-33)20-10-17(6-5-9-32)11-24(38-2)30(20)42-29/h5-8,10-14,21,27-29,32-36H,9,15-16H2,1-4H3/b6-5+

InChI Key

LCXGTSCVCJANHX-AATRIKPKSA-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
Arabidopsis thaliana	LOTUS Database	35616633
Buddleja davidii	LOTUS Database	35616633
Ehretia ovalifolia	LOTUS Database	35616633
Euonymus alatus	LOTUS Database	35616633
Populus tremula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Norlignan skeleton
Methoxyphenol
Cinnamyl alcohol
Dimethoxybenzene
M-dimethoxybenzene
Coumaran
Benzofuran
Phenol ether
Anisole
Phenoxy compound
Styrene
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Primary alcohol
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzofurans (CHEBI:86632 )

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	1.82	ChemAxon
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.53 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	154.38 m³·mol⁻¹	ChemAxon
Polarizability	62.07 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

C00000684

Chemspider ID

10254223

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21627696

PDB ID

Not Available

ChEBI ID

86632

Good Scents ID

Not Available

References

General References

Liu S, Yang W, Liu SB, Wang H, Guo ZK, Zeng YB, Dong WH, Mei WL, Dai HF: A new dolabellane diterpenoid and a sesquilignan from Aglaia odorata var. microphyllina. Nat Prod Commun. 2014 Jan;9(1):7-8. [PubMed:24660448 ]
LOTUS database [Link]

Showing NP-Card for buddlenol b (NP0195462)

MOL for NP0195462 (buddlenol b)

3D MOL for NP0195462 (buddlenol b)

3D SDF for NP0195462 (buddlenol b)

3D-SDF for NP0195462 (buddlenol b)

PDB for NP0195462 (buddlenol b)

3D PDB for NP0195462 (buddlenol b)

SMILES for NP0195462 (buddlenol b)

INCHI for NP0195462 (buddlenol b)

Structure for NP0195462 (buddlenol b)

3D Structure for NP0195462 (buddlenol b)