NP-MRD: Showing NP-Card for Malibatol B (NP0082858)

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Record Information

Version

2.0

Created at

2022-04-29 03:56:20 UTC

Updated at

2022-04-29 03:56:20 UTC

NP-MRD ID

NP0082858

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Malibatol B

Description

1-(3,4-Dihydroxyphenyl)-7alpha-(4-hydroxyphenyl)-6,7-dihydro-2-oxa-2H-dibenz[cd,h]azulene-4,6beta,8,10,11-pentol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Malibatol B is found in Hopea malibato. Based on a literature review very few articles have been published on 1-(3,4-Dihydroxyphenyl)-7alpha-(4-hydroxyphenyl)-6,7-dihydro-2-oxa-2H-dibenz[cd,h]azulene-4,6beta,8,10,11-pentol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205562D          

 37 42  0  0  1  0            999 V2000
    3.8744   -0.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0699    0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5652    0.8783    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7402    0.8906    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2164    0.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880   -0.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1259   -0.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0030   -1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892   -1.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8091   -1.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0106   -0.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7910   -0.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0075    0.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292205562D          

 37 42  0  0  1  0            999 V2000
    3.8744   -0.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2627   -0.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4708   -1.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0082858

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](C2=CC=C(O)C=C2)C2=C(C3=C(OC4=CC(O)=CC1=C34)C1=CC(O)=C(O)C=C1)C(O)=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C28H20O9/c29-13-4-1-11(2-5-13)21-23-18(33)10-19(34)27(36)24(23)25-22-15(26(21)35)8-14(30)9-20(22)37-28(25)12-3-6-16(31)17(32)7-12/h1-10,21,26,29-36H/t21-,26-/m1/s1

> <INCHI_KEY>
OTJUFGKCGUDJEI-QFQXNSOFSA-N

> <FORMULA>
C28H20O9

> <MOLECULAR_WEIGHT>
500.459

> <EXACT_MASS>
500.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
50.83743718547803

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8R,9S)-16-(3,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-1(16),2(7),3,5,10(17),11,13-heptaene-3,4,6,9,12-pentol

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
4.052946420666666

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.775088617641956

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.227739063883405

> <JCHEM_PKA_STRONGEST_BASIC>
-3.274592706129005

> <JCHEM_POLAR_SURFACE_AREA>
174.98

> <JCHEM_REFRACTIVITY>
133.27760000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8R,9S)-16-(3,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-1(16),2(7),3,5,10(17),11,13-heptaene-3,4,6,9,12-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       7.232  -1.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.597   0.421   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.655   1.640   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.115   1.662   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.137   0.473   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.458  -1.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.835  -1.722   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.606  -3.245   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.087  -3.498   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.377  -2.131   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.886  -1.744   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.477  -0.259   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.557   0.838   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.014   0.128   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.703  -4.326   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.187  -3.916   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.285  -4.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.897  -6.487   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.413  -6.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.316  -5.816   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.994  -7.568   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.769  -4.587   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.468   3.060   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.344   3.017   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.495   4.302   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.184   5.680   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.721   5.772   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.570   4.487   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.881   3.109   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.410   7.149   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.075   0.853   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.189  -0.211   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.824  -1.707   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.345  -2.139   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.930  -3.564   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      10.937  -2.771   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       9.440   2.350   0.000  0.00  0.00           O+0
CONECT    1    2    7   34                                                  
CONECT    2    1    3   31                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    5                                                       
CONECT   14   12                                                            
CONECT   15    8   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   18                                                            
CONECT   22   17                                                            
CONECT   23    4                                                            
CONECT   24    3   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   27                                                            
CONECT   31    2   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33    1   35                                                  
CONECT   35   34                                                            
CONECT   36   33                                                            
CONECT   37   31                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Value	Source
1-(3,4-Dihydroxyphenyl)-7a-(4-hydroxyphenyl)-6,7-dihydro-2-oxa-2H-dibenz[CD,H]azulene-4,6b,8,10,11-pentol	Generator
1-(3,4-Dihydroxyphenyl)-7α-(4-hydroxyphenyl)-6,7-dihydro-2-oxa-2H-dibenz[CD,H]azulene-4,6β,8,10,11-pentol	Generator

Chemical Formula

C₂₈H₂₀O₉

Average Mass

500.4590 Da

Monoisotopic Mass

500.11073 Da

IUPAC Name

(8R,9S)-16-(3,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-1(16),2(7),3,5,10(17),11,13-heptaene-3,4,6,9,12-pentol

Traditional Name

(8R,9S)-16-(3,4-dihydroxyphenyl)-8-(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0^{2,7}.0^{14,17}]heptadeca-1(16),2(7),3,5,10(17),11,13-heptaene-3,4,6,9,12-pentol

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](C2=CC=C(O)C=C2)C2=C(C3=C(OC4=CC(O)=CC1=C34)C1=CC(O)=C(O)C=C1)C(O)=C(O)C=C2O

InChI Identifier

InChI=1S/C28H20O9/c29-13-4-1-11(2-5-13)21-23-18(33)10-19(34)27(36)24(23)25-22-15(26(21)35)8-14(30)9-20(22)37-28(25)12-3-6-16(31)17(32)7-12/h1-10,21,26,29-36H/t21-,26-/m1/s1

InChI Key

OTJUFGKCGUDJEI-QFQXNSOFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Hopea malibato	Plant	KNApSAcK

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
2-phenylbenzofuran
Phenylbenzofuran
Benzofuran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.24	ALOGPS
logP	4.05	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	174.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.28 m³·mol⁻¹	ChemAxon
Polarizability	50.84 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

101940878

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Malibatol B (NP0082858)

MOL for NP0082858 (Malibatol B)

3D MOL for NP0082858 (Malibatol B)

3D SDF for NP0082858 (Malibatol B)

3D-SDF for NP0082858 (Malibatol B)

PDB for NP0082858 (Malibatol B)

3D PDB for NP0082858 (Malibatol B)

SMILES for NP0082858 (Malibatol B)

INCHI for NP0082858 (Malibatol B)

Structure for NP0082858 (Malibatol B)

3D Structure for NP0082858 (Malibatol B)