NP-MRD: Showing NP-Card for hydramacrophyllol a (NP0238551)

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Record Information

Version

2.0

Created at

2022-09-06 21:57:57 UTC

Updated at

2022-09-06 21:57:57 UTC

NP-MRD ID

NP0238551

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hydramacrophyllol a

Description

Hydramacrophyllol A belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone. Hydramacrophyllol A 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. hydramacrophyllol a is found in Scorzonera tomentosa and Hydrangea macrophylla. Based on a literature review very few articles have been published on hydramacrophyllol A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    1.2692   -0.9393   -3.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1709   -0.7563   -2.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340   -0.6435   -1.2603 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3616   -0.4495    0.0718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2730    0.7934    0.6621 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1013    1.9472    0.0141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7470    0.6045    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4578    0.7886   -0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8309    0.6090   -0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5345    0.2396    0.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9122    0.0596    0.4385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8471    0.0485    1.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4832    0.2317    1.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178   -0.4426    0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7397   -0.2923    1.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0782   -0.3355    0.9095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5633   -0.5231   -0.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6839   -0.6745   -1.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1305   -0.8659   -2.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3153   -0.6286   -1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0471   -1.3067    0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0238    0.8302    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1966    2.7105    0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289    1.0774   -1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3160    0.7754   -1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2358   -0.8791    0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3619   -0.2457    2.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9800    0.0734    2.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3118   -0.1489    2.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7883   -0.2162    1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6328   -0.5503   -0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -0.8910   -2.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 20  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 14  4  1  0
 13  7  1  0
 14 20  1  0
  6 23  1  0
  5 22  1  1
  4 21  1  1
 19 32  1  0
 17 31  1  0
 16 30  1  0
 15 29  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
M  END


  Mrv1652309062223582D          

 20 22  0  0  1  0            999 V2000
    0.8838   -2.1500    0.0000 O   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
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    1.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    1.4402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 C   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
    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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 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
 18 20  2  0  0  0  0
 14 20  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238551

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]([C@H]1OC(=O)C2=C(O)C=CC=C12)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-9-6-4-8(5-7-9)13(18)14-10-2-1-3-11(17)12(10)15(19)20-14/h1-7,13-14,16-18H/t13-,14-/m0/s1

> <INCHI_KEY>
FADYYEHFGLVECU-KBPBESRZSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.256

> <EXACT_MASS>
272.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.69802567741242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-7-hydroxy-3-[(S)-hydroxy(4-hydroxyphenyl)methyl]-1,3-dihydro-2-benzofuran-1-one

> <JCHEM_LOGP>
2.724724683333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.818337309623079

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.211642368581387

> <JCHEM_PKA_STRONGEST_BASIC>
-3.553949812303209

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
70.845

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-7-hydroxy-3-[(S)-hydroxy(4-hydroxyphenyl)methyl]-3H-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.680   2.552   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.143   1.728   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.887   0.583   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.393   0.904   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.869   2.368   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.376   2.688   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.839   3.513   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.333   3.192   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7                                                       
CONECT   14    4   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14    2                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(3S)-7-Hydroxy-3-((S)-hydroxy(4-hydroxyphenyl)methyl)- isobenzofuran-1(3H)-one	ChEBI

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2560 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

(3S)-7-hydroxy-3-[(S)-hydroxy(4-hydroxyphenyl)methyl]-1,3-dihydro-2-benzofuran-1-one

Traditional Name

(3S)-7-hydroxy-3-[(S)-hydroxy(4-hydroxyphenyl)methyl]-3H-2-benzofuran-1-one

CAS Registry Number

Not Available

SMILES

O[C@H]([C@H]1OC(=O)C2=C(O)C=CC=C12)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H12O5/c16-9-6-4-8(5-7-9)13(18)14-10-2-1-3-11(17)12(10)15(19)20-14/h1-7,13-14,16-18H/t13-,14-/m0/s1

InChI Key

FADYYEHFGLVECU-KBPBESRZSA-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
Gelasia tomentosa	LOTUS Database	35616633
Hydrangea macrophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Benzofuranones

Direct Parent

Benzofuranones

Alternative Parents

Substituents

Benzofuranone
Isobenzofuranone
Phthalide
Isocoumaran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:68136 )
phenols (CHEBI:68136 )
gamma-lactone (CHEBI:68136 )
isobenzofuranone (CHEBI:68136 )

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	2.72	ChemAxon
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.84 m³·mol⁻¹	ChemAxon
Polarizability	26.7 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

154949

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

177995

PDB ID

Not Available

ChEBI ID

68136

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for hydramacrophyllol a (NP0238551)

MOL for NP0238551 (hydramacrophyllol a)

3D MOL for NP0238551 (hydramacrophyllol a)

3D SDF for NP0238551 (hydramacrophyllol a)

3D-SDF for NP0238551 (hydramacrophyllol a)

PDB for NP0238551 (hydramacrophyllol a)

3D PDB for NP0238551 (hydramacrophyllol a)

SMILES for NP0238551 (hydramacrophyllol a)

INCHI for NP0238551 (hydramacrophyllol a)

Structure for NP0238551 (hydramacrophyllol a)

3D Structure for NP0238551 (hydramacrophyllol a)