NP-MRD: Showing NP-Card for Amaronol B (NP0138705)

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Record Information

Version

2.0

Created at

2022-06-29 18:32:26 UTC

Updated at

2022-06-29 18:32:27 UTC

NP-MRD ID

NP0138705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Amaronol B

Description

Amaronol b belongs to the class of organic compounds known as auronols. These are aurone flavonoids in which the pyran ring of the aurone skeleton carries a hydroxyl group at the 2-position. Thus, amaronol b is considered to be a flavonoid lipid molecule. Amaronol B is found in Pseudolarix amabilis. Amaronol b is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    6.2443   -0.2623    0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284   -0.9091    1.2194 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412   -0.4972    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4300   -1.0626   -0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2129   -2.0525   -1.1501 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -0.6496   -1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4731    0.3366   -0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    0.7591   -1.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9800    0.0083   -0.9512 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9161   -1.3491   -1.1984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3778    0.2072    0.3654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7566    0.1016    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6699   -0.1560    1.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0270   -0.2088    1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9498   -0.4642    2.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5229   -0.0007   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6406    0.2568   -1.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0671    0.4762   -2.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2821    0.3045   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1258    0.5527   -1.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1070    1.0940   -2.8581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8801    0.9071    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0601    0.4944    1.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4912    1.0559    2.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7398   -0.0102    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0860    0.7203    0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9552   -0.9115    0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9268   -2.4776   -2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995   -1.1432   -2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0478    1.8396   -1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3503    0.6368   -2.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4595   -1.6188   -1.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002   -0.3175    2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3912    0.2329    2.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5761   -0.0299   -0.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4607    0.6637   -3.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173    1.6920    0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0127    1.7811    2.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
  7 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 20  9  1  0
 19 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 22 37  1  0
 24 38  1  0
M  END


  Mrv1533004251506082D          

 24 26  0  0  0  0            999 V2000
    0.1137    3.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268    3.0820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553    2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1684    1.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530    1.9779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9969    0.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122    0.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -1.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   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
    2.6378   -2.3479    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4009    1.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2293    2.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424    2.5721    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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 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
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
  7 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(CC2(O)OC3=CC(O)=CC(O)=C3C2=O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O8/c1-23-14-10(19)2-7(3-11(14)20)6-16(22)15(21)13-9(18)4-8(17)5-12(13)24-16/h2-5,17-20,22H,6H2,1H3

> <INCHI_KEY>
YCDTYNVODFTPCZ-UHFFFAOYSA-N

> <FORMULA>
C16H14O8

> <MOLECULAR_WEIGHT>
334.28

> <EXACT_MASS>
334.068867411

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.40358657292197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3,5-dihydroxy-4-methoxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
2.311512859333333

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.99012420127626

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.593178959706408

> <JCHEM_PKA_STRONGEST_BASIC>
-4.724805673339208

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
81.5174

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amaronol B

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       0.212   6.783   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.357   5.753   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.037   4.247   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.181   3.216   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.646   3.692   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.861   1.710   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.396   1.234   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.076  -0.272   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.076  -2.333   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.748   2.264   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.428   3.771   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.573   4.801   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   20                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19    9   21                                                  
CONECT   21   20                                                            
CONECT   22    7   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
2,4,6-Trihydroxy-2-((3',5'-dihydroxy-4'-methoxyphenyl)methyl)-3(2H)-benzofuranone	MeSH

Chemical Formula

C₁₆H₁₄O₈

Average Mass

334.2800 Da

Monoisotopic Mass

334.06887 Da

IUPAC Name

2-[(3,5-dihydroxy-4-methoxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one

Traditional Name

amaronol B

CAS Registry Number

226561-02-0

SMILES

COC1=C(O)C=C(CC2(O)OC3=CC(O)=CC(O)=C3C2=O)C=C1O

InChI Identifier

InChI=1S/C16H14O8/c1-23-14-10(19)2-7(3-11(14)20)6-16(22)15(21)13-9(18)4-8(17)5-12(13)24-16/h2-5,17-20,22H,6H2,1H3

InChI Key

YCDTYNVODFTPCZ-UHFFFAOYSA-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
Pseudolarix amabilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as auronols. These are aurone flavonoids in which the pyran ring of the aurone skeleton carries a hydroxyl group at the 2-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Auronols

Direct Parent

Auronols

Alternative Parents

Substituents

Auronol
Methoxyphenol
Benzofuran
Coumaran
Anisole
Methoxybenzene
Phenol ether
Aryl alkyl ketone
Aryl ketone
Resorcinol
Phenoxy compound
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Acyloin
Vinylogous acid
Hemiacetal
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Aurone flavonoids (LMPK12130075 )

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	1.13	ALOGPS
logP	2.31	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.59	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.52 m³·mol⁻¹	ChemAxon
Polarizability	31.4 Å³	ChemAxon
Number of Rings	3	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

485522

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Amaronol B (NP0138705)

MOL for NP0138705 (Amaronol B)

3D MOL for NP0138705 (Amaronol B)

3D SDF for NP0138705 (Amaronol B)

3D-SDF for NP0138705 (Amaronol B)

PDB for NP0138705 (Amaronol B)

3D PDB for NP0138705 (Amaronol B)

SMILES for NP0138705 (Amaronol B)

INCHI for NP0138705 (Amaronol B)

Structure for NP0138705 (Amaronol B)

3D Structure for NP0138705 (Amaronol B)