NP-MRD: Showing NP-Card for Herpepentol (NP0050462)

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Record Information

Version

2.0

Created at

2022-04-27 21:44:10 UTC

Updated at

2022-04-27 21:44:10 UTC

NP-MRD ID

NP0050462

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Herpepentol

Description

4-[(2R,3R)-5-[(2S,3S)-5-[(2S,3S)-5-[(2S,3R,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Herpepentol is found in Herpetospermum caudigerum Wall. Based on a literature review very few articles have been published on 4-[(2R,3R)-5-[(2S,3S)-5-[(2S,3S)-5-[(2S,3R,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223442D          

 65 73  0  0  1  0            999 V2000
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M  END


  Mrv1652304272223442D          

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 57 62  1  0  0  0  0
 61 63  1  0  0  0  0
 63 64  1  0  0  0  0
 60 65  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050462

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC2=C1O[C@@H]([C@@H]2CO)C1=CC2=C(O[C@@H]([C@@H]2CO)C2=CC3=C(O[C@H]([C@H]3CO)C3=CC=C(O)C(OC)=C3)C(OC)=C2)C(OC)=C1)[C@H]1OC[C@@H](CC2=CC(OC)=C(O)C=C2)[C@@H]1CO

> <INCHI_IDENTIFIER>
InChI=1S/C50H54O15/c1-57-39-11-24(6-8-37(39)55)10-29-23-62-44(33(29)19-51)26-12-30-35(21-53)46(64-49(30)41(16-26)59-3)28-14-32-36(22-54)47(65-50(32)43(18-28)61-5)27-13-31-34(20-52)45(63-48(31)42(17-27)60-4)25-7-9-38(56)40(15-25)58-2/h6-9,11-18,29,33-36,44-47,51-56H,10,19-23H2,1-5H3/t29-,33+,34+,35-,36-,44-,45+,46-,47-/m1/s1

> <INCHI_KEY>
BXBQFZMPZDWGJY-IFFHWGSGSA-N

> <FORMULA>
C50H54O15

> <MOLECULAR_WEIGHT>
894.967

> <EXACT_MASS>
894.346271039

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
93.12554456943033

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2R,3R)-5-[(2S,3S)-5-[(2S,3S)-5-[(2S,3R,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol

> <ALOGPS_LOGP>
4.44

> <JCHEM_LOGP>
3.741221611999998

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.422944073392024

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.750759268904671

> <JCHEM_PKA_STRONGEST_BASIC>
-2.639332775008638

> <JCHEM_POLAR_SURFACE_AREA>
204.44999999999996

> <JCHEM_REFRACTIVITY>
237.65449999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2R,3R)-5-[(2S,3S)-5-[(2S,3S)-5-[(2S,3R,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0     -10.128  -6.235   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.461  -5.465   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.461  -3.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.128  -3.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.794  -3.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.794  -5.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.460  -3.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.054  -3.781   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.023  -2.637   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.793  -1.303   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.023   0.031   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.483   0.031   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.483  -2.637   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.605  -2.216   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.635  -3.361   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.865  -4.695   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.359  -4.374   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.167  -3.200   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.072  -4.446   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.603  -4.285   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.509  -5.531   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.882  -6.938   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.351  -7.099   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.445  -5.853   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.787  -8.183   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      14.040  -5.370   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      14.945  -6.616   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.925  -0.710   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.389  -0.234   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.864   2.547   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       0.287  -5.158   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -5.793   1.365   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -5.023   2.698   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -7.299  -1.623   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -5.733  -5.287   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -4.269  -5.763   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0     -12.795  -3.155   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0     -12.795  -1.615   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -12.606  -6.495   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0     -11.979  -7.902   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -10.448  -7.741   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -9.417  -8.885   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -7.911  -8.565   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0     -12.749  -9.236   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -11.979 -10.569   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -12.749 -11.903   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -14.289 -11.903   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -15.059 -10.569   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0     -14.289  -9.236   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0     -16.599 -10.569   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0     -17.369 -11.903   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0     -15.059 -13.237   0.000  0.00  0.00           O+0
CONECT    1    2    6   54                                                  
CONECT    2    1    3   52                                                  
CONECT    3    2    4   50                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   47                                                  
CONECT    8    7    9   48                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   47                                                  
CONECT   11   10   12   45                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16   42                                                  
CONECT   16   15   17   43                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   42                                                  
CONECT   19   18   20   40                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21   24   27                                                  
CONECT   24   23   25   38                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   23                                                       
CONECT   28   25   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   32                                                            
CONECT   36   31   37                                                       
CONECT   37   36                                                            
CONECT   38   24   39                                                       
CONECT   39   38                                                            
CONECT   40   19   41                                                       
CONECT   41   40                                                            
CONECT   42   18   15                                                       
CONECT   43   16   44                                                       
CONECT   44   43                                                            
CONECT   45   11   46                                                       
CONECT   46   45                                                            
CONECT   47   10    7                                                       
CONECT   48    8   49                                                       
CONECT   49   48                                                            
CONECT   50    3   51                                                       
CONECT   51   50                                                            
CONECT   52    2   53                                                       
CONECT   53   52   54   57                                                  
CONECT   54   53    1   55                                                  
CONECT   55   54   56                                                       
CONECT   56   55                                                            
CONECT   57   53   58   62                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61   65                                                  
CONECT   61   60   62   63                                                  
CONECT   62   61   57                                                       
CONECT   63   61   64                                                       
CONECT   64   63                                                            
CONECT   65   60                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  146    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₀H₅₄O₁₅

Average Mass

894.9670 Da

Monoisotopic Mass

894.34627 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC2=C1O[C@@H]([C@@H]2CO)C1=CC2=C(O[C@@H]([C@@H]2CO)C2=CC3=C(O[C@H]([C@H]3CO)C3=CC=C(O)C(OC)=C3)C(OC)=C2)C(OC)=C1)[C@H]1OC[C@@H](CC2=CC(OC)=C(O)C=C2)[C@@H]1CO

InChI Identifier

InChI=1S/C50H54O15/c1-57-39-11-24(6-8-37(39)55)10-29-23-62-44(33(29)19-51)26-12-30-35(21-53)46(64-49(30)41(16-26)59-3)28-14-32-36(22-54)47(65-50(32)43(18-28)61-5)27-13-31-34(20-52)45(63-48(31)42(17-27)60-4)25-7-9-38(56)40(15-25)58-2/h6-9,11-18,29,33-36,44-47,51-56H,10,19-23H2,1-5H3/t29-,33+,34+,35-,36-,44-,45+,46-,47-/m1/s1

InChI Key

BXBQFZMPZDWGJY-IFFHWGSGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Herpetospermum caudigerum Wall.	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
Furanoid lignan
7,9p-epoxylignan
Tetrahydrofuran lignan
Neolignan skeleton
Norlignan skeleton
Methoxyphenol
Coumaran
Benzofuran
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	4.44	ALOGPS
logP	3.74	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	204.45 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	237.65 m³·mol⁻¹	ChemAxon
Polarizability	93.13 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162994657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Herpepentol (NP0050462)

MOL for NP0050462 (Herpepentol)

3D MOL for NP0050462 (Herpepentol)

3D SDF for NP0050462 (Herpepentol)

3D-SDF for NP0050462 (Herpepentol)

PDB for NP0050462 (Herpepentol)

3D PDB for NP0050462 (Herpepentol)

SMILES for NP0050462 (Herpepentol)

INCHI for NP0050462 (Herpepentol)

Structure for NP0050462 (Herpepentol)

3D Structure for NP0050462 (Herpepentol)