NP-MRD: Showing NP-Card for 6alpha-Hydroxymaackiain (NP0047715)

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Record Information

Version

2.0

Created at

2022-03-17 20:44:45 UTC

Updated at

2022-03-17 20:44:46 UTC

NP-MRD ID

NP0047715

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6alpha-Hydroxymaackiain

Description

6Alpha-Hydroxymaackiain, also known as 6a-hydroxyinermin, belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, 6alpha-hydroxymaackiain is considered to be a flavonoid lipid molecule. 6Alpha-Hydroxymaackiain is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6alpha-Hydroxymaackiain has been detected, but not quantified in, several different foods, such as common pea, herbs and spices, pulses, and tea. 6alpha-Hydroxymaackiain is found in Trifolium pratense . This could make 6alpha-hydroxymaackiain a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307192D          

 22 26  0  0  0  0            999 V2000
    0.9678    2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    2.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    0.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0867    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405    1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    1.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    1.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292    1.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901    0.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582    2.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    2.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0749    1.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0663    0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    0.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5325    0.9754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5794    2.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5830    2.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  2  0  0  0  0
  9  2  1  0  0  0  0
 10  4  2  0  0  0  0
 11  3  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  2  0  0  0  0
 12 10  1  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  1  0  0  0  0
 16  6  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18 16  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
 20  7  1  0  0  0  0
 20 13  1  0  0  0  0
 21  7  1  0  0  0  0
 21 14  1  0  0  0  0
 22 12  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047715

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO2

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c17-8-1-2-9-11(3-8)19-6-16(18)10-4-13-14(21-7-20-13)5-12(10)22-15(9)16/h1-5,15,17-18H,6-7H2

> <INCHI_KEY>
GLMPLZUBQDAZEN-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.440260064556306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaene-1,16-diol

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.634947747666667

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.009343195182975

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.413307566628584

> <JCHEM_PKA_STRONGEST_BASIC>
-4.121505541933158

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
73.45270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6a-hydroxymaackiain

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.807   4.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.343   4.464   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.992   1.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.387   1.625   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.495   4.703   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.925   0.633   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.142   3.034   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.131   2.973   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.204   3.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.081   2.441   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.528   1.803   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.135   3.980   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.747   2.348   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.801   3.887   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.740   3.294   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.601   2.017   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.405   2.866   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.590   0.837   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.389   0.526   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.194   1.821   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.282   4.311   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.688   4.507   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    9                                                       
CONECT    3    8   11                                                       
CONECT    4   10   13                                                       
CONECT    5   12   14                                                       
CONECT    6   16   19                                                       
CONECT    7   20   21                                                       
CONECT    8    1    3   17                                                  
CONECT    9    2   11   15                                                  
CONECT   10    4   12   16                                                  
CONECT   11    3    9   19                                                  
CONECT   12    5   10   22                                                  
CONECT   13    4   14   20                                                  
CONECT   14    5   13   21                                                  
CONECT   15    9   16   22                                                  
CONECT   16    6   10   15   18                                             
CONECT   17    8                                                            
CONECT   18   16                                                            
CONECT   19    6   11                                                       
CONECT   20    7   13                                                       
CONECT   21    7   14                                                       
CONECT   22   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Value	Source
6a-Hydroxymaackiain	Generator
6Α-hydroxymaackiain	Generator
3,6a-Dihydroxy-8,9-methylenedioxypterocarpan	HMDB
6a-Hydroxyinermin	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2629 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaene-1,16-diol

Traditional Name

6a-hydroxymaackiain

CAS Registry Number

14602-93-8

SMILES

OC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO2

InChI Identifier

InChI=1S/C16H12O6/c17-8-1-2-9-11(3-8)19-6-16(18)10-4-13-14(21-7-20-13)5-12(10)22-15(9)16/h1-5,15,17-18H,6-7H2

InChI Key

GLMPLZUBQDAZEN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pisum sativum	FooDB	KNAPSACK
Trifolium pratense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Chromane
1-benzopyran
Benzopyran
Coumaran
Benzodioxole
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070133 )
a small molecule (CPD-3942 )

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	2.03	ALOGPS
logP	1.63	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.38 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.45 m³·mol⁻¹	ChemAxon
Polarizability	29.44 Å³	ChemAxon
Number of Rings	5	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

HMDB0033720

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011839

KNApSAcK ID

C00009677

Chemspider ID

24785132

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257487

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6alpha-Hydroxymaackiain (NP0047715)

MOL for NP0047715 (6alpha-Hydroxymaackiain)

3D MOL for NP0047715 (6alpha-Hydroxymaackiain)

3D SDF for NP0047715 (6alpha-Hydroxymaackiain)

3D-SDF for NP0047715 (6alpha-Hydroxymaackiain)

PDB for NP0047715 (6alpha-Hydroxymaackiain)

3D PDB for NP0047715 (6alpha-Hydroxymaackiain)

SMILES for NP0047715 (6alpha-Hydroxymaackiain)

INCHI for NP0047715 (6alpha-Hydroxymaackiain)

Structure for NP0047715 (6alpha-Hydroxymaackiain)

3D Structure for NP0047715 (6alpha-Hydroxymaackiain)