NP-MRD: Showing NP-Card for 4-hydroxymaackiain (NP0183891)

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Record Information

Version

2.0

Created at

2022-09-03 22:53:00 UTC

Updated at

2022-09-03 22:53:01 UTC

NP-MRD ID

NP0183891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxymaackiain

Description

4-Hydroxymaackiain 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, 4-hydroxymaackiain is considered to be a flavonoid lipid molecule. 4-hydroxymaackiain is found in Dalbergia spruceana, Psorothamnus arborescens and Sophora stenophylla. 4-Hydroxymaackiain is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 38  0  0  0  0  0  0  0  0999 V2000
    6.0129    0.7095    0.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6351    0.4992    0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259    0.4160    1.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7847    0.2110    1.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9318    0.0864    0.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4540    0.1716   -0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7794    0.3742   -0.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921    0.4580   -1.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460    0.0383   -1.4431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4446   -0.8455   -1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100   -1.0312   -0.0271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5364   -0.5947   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7037   -1.2498   -0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8984   -0.5668   -0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9107    0.7301    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7501    1.3669    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5414    0.7008    0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2242    1.0878    0.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4787   -0.1342    1.0149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2238    1.1522    0.0789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0941    0.0428   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2284   -0.9111   -0.6709 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6084    0.7963    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7968    0.5139    2.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3586    0.1417    2.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2448    0.6039   -2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3142   -0.4351   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7333   -1.8484   -1.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1141   -2.0932    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737   -2.2681   -0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7557    2.3999    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1910   -0.5055    2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4331   -0.2603    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9059    0.2433   -0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  5 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 22  1  0
 22 21  1  0
 21 20  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  3  2  1  0
 11 19  1  0
  9  6  1  0
 12 17  1  0
 20 15  1  0
  1 23  1  0
  8 26  1  0
  4 25  1  0
  3 24  1  0
 19 32  1  1
 16 31  1  0
 21 33  1  0
 21 34  1  0
 13 30  1  0
 11 29  1  1
 10 27  1  0
 10 28  1  0
M  END

  Mrv1652310051713272D          

 22 26  0  0  0  0            999 V2000
    1.7908    2.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9678    2.3341    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
    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
    3.5361    1.0807    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
    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
    1.0671    0.9086    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
    1.8901    0.9659    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
    0.7053    0.1672    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
  7  1  1  0  0  0  0
  8  3  2  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  2  1  0  0  0  0
 11  4  2  0  0  0  0
 11  8  1  0  0  0  0
 12  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  2  0  0  0  0
 15  7  1  0  0  0  0
 15  9  1  0  0  0  0
 16  7  2  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 18 14  1  0  0  0  0
 19  5  1  0  0  0  0
 19 16  1  0  0  0  0
 20  6  1  0  0  0  0
 20 12  1  0  0  0  0
 21  6  1  0  0  0  0
 21 13  1  0  0  0  0
 22 11  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183891

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(O)C2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1CO2

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

> <INCHI_KEY>
GGIPOZCJJKKBBV-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.266

> <EXACT_MASS>
300.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.531565258329472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2,4(8),9,13(18),14,16-hexaene-16,17-diol

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.9865628080000004

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.96255714437671

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.464417022855535

> <JCHEM_PKA_STRONGEST_BASIC>
-4.37111105714946

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
74.34570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2,4(8),9,13(18),14,16-hexaene-16,17-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0       3.343   4.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.806   4.357   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.387   1.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.495   4.703   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.925   0.633   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.142   3.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.204   3.187   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.081   2.441   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.601   2.017   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.131   2.973   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.135   3.980   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.747   2.348   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.801   3.887   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.992   1.696   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       3.528   1.803   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       1.317   0.312   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      12.281   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    7                                                       
CONECT    2    1   10                                                       
CONECT    3    8   12                                                       
CONECT    4   11   13                                                       
CONECT    5    9   19                                                       
CONECT    6   20   21                                                       
CONECT    7    1   15   16                                                  
CONECT    8    3    9   11                                                  
CONECT    9    5    8   15                                                  
CONECT   10    2   14   17                                                  
CONECT   11    4    8   22                                                  
CONECT   12    3   13   20                                                  
CONECT   13    4   12   21                                                  
CONECT   14   10   16   18                                                  
CONECT   15    7    9   22                                                  
CONECT   16    7   14   19                                                  
CONECT   17   10                                                            
CONECT   18   14                                                            
CONECT   19    5   16                                                       
CONECT   20    6   12                                                       
CONECT   21    6   13                                                       
CONECT   22   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Value	Source
3,4-DiOHMe-pterocarpan	MeSH
3,4-Dihydroxy-8,9-methylenedioxypterocarpan	MeSH

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2660 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2,4(8),9,13(18),14,16-hexaene-16,17-diol

Traditional Name

5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2,4(8),9,13(18),14,16-hexaene-16,17-diol

CAS Registry Number

Not Available

SMILES

OC1=C(O)C2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1CO2

InChI Identifier

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

InChI Key

GGIPOZCJJKKBBV-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
Dalbergia spruceana	LOTUS Database	35616633
Psorothamnus arborescens	LOTUS Database	35616633
Sophora stenophylla	LOTUS Database	35616633

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-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070080 )

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	2.24	ALOGPS
logP	1.99	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-4.4	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	74.35 m³·mol⁻¹	ChemAxon
Polarizability	29.53 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

HMDB0150733

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

24013844

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxymaackiain (NP0183891)

MOL for NP0183891 (4-hydroxymaackiain)

3D MOL for NP0183891 (4-hydroxymaackiain)

3D SDF for NP0183891 (4-hydroxymaackiain)

3D-SDF for NP0183891 (4-hydroxymaackiain)

PDB for NP0183891 (4-hydroxymaackiain)

3D PDB for NP0183891 (4-hydroxymaackiain)

SMILES for NP0183891 (4-hydroxymaackiain)

INCHI for NP0183891 (4-hydroxymaackiain)

Structure for NP0183891 (4-hydroxymaackiain)

3D Structure for NP0183891 (4-hydroxymaackiain)