NP-MRD: Showing NP-Card for Rivulobirin E (NP0071724)

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Record Information

Version

2.0

Created at

2022-04-28 17:04:11 UTC

Updated at

2022-04-28 17:04:11 UTC

NP-MRD ID

NP0071724

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rivulobirin E

Description

Rivulobirin E belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Rivulobirin E is found in Heracleum candicans, Heracleum candicans WALL. , Pleurospermum rivulorum and Prangos pabularia. Based on a literature review very few articles have been published on Rivulobirin E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219042D          

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M  END

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M  END


  Mrv1652304282219042D          

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   -0.0734   -5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2286   -4.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -5.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4171   -4.7528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0845   -4.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7520   -4.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9095   -7.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4970   -8.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6720   -8.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2595   -9.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2595   -7.6808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 22 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 19 31  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
  4 38  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
  1 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071724

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H](COC1=C2OC(=O)C=CC2=CC2=C1OC=C2)OC(C)(C)[C@H](O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C32H30O11/c1-31(2,36)22(16-40-30-26-20(10-12-38-26)14-18-6-8-24(35)42-28(18)30)43-32(3,4)21(33)15-39-29-25-19(9-11-37-25)13-17-5-7-23(34)41-27(17)29/h5-14,21-22,33,36H,15-16H2,1-4H3/t21-,22-/m1/s1

> <INCHI_KEY>
OIZNBPDWHFCLKY-FGZHOGPDSA-N

> <FORMULA>
C32H30O11

> <MOLECULAR_WEIGHT>
590.581

> <EXACT_MASS>
590.178811786

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
58.553539007724716

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(2R)-2-hydroxy-3-{[(2R)-3-hydroxy-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)butan-2-yl]oxy}-3-methylbutoxy]-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
3.4847565509999985

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.289498461930464

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.185853240031932

> <JCHEM_PKA_STRONGEST_BASIC>
-2.614499282285214

> <JCHEM_POLAR_SURFACE_AREA>
147.03

> <JCHEM_REFRACTIVITY>
152.81930000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-[(2R)-2-hydroxy-3-{[(2R)-3-hydroxy-3-methyl-1-({7-oxofuro[3,2-g]chromen-9-yl}oxy)butan-2-yl]oxy}-3-methylbutoxy]furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      10.588 -13.004   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.128 -13.004   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.898 -11.670   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.128 -10.337   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.588 -10.337   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.818 -11.670   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.278 -11.670   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.508 -10.337   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.968 -10.337   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.198 -11.670   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.198  -9.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.428  -7.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.531  -8.233   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.864  -9.773   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.530  -9.003   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.530  -7.463   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.197  -6.693   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.602  -4.859   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.507  -3.613   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.602  -2.367   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.531  -5.153   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.864  -5.153   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.197  -9.773   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.137 -10.543   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.427  -8.439   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.967 -11.107   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      10.112  -8.872   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      11.358  -7.967   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.604  -8.872   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.898 -14.338   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.128 -15.671   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.588 -15.671   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       9.818 -17.005   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       9.818 -14.338   0.000  0.00  0.00           O+0
CONECT    1    2    6   43                                                  
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   38                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   31                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   18   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
CONECT   27   20   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   19                                                       
CONECT   32   15   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36    5   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37    4                                                       
CONECT   39    2   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    1                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₀O₁₁

Average Mass

590.5810 Da

Monoisotopic Mass

590.17881 Da

IUPAC Name

9-[(2R)-2-hydroxy-3-{[(2R)-3-hydroxy-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)butan-2-yl]oxy}-3-methylbutoxy]-7H-furo[3,2-g]chromen-7-one

Traditional Name

9-[(2R)-2-hydroxy-3-{[(2R)-3-hydroxy-3-methyl-1-({7-oxofuro[3,2-g]chromen-9-yl}oxy)butan-2-yl]oxy}-3-methylbutoxy]furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H](COC1=C2OC(=O)C=CC2=CC2=C1OC=C2)OC(C)(C)[C@H](O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C2

InChI Identifier

InChI=1S/C32H30O11/c1-31(2,36)22(16-40-30-26-20(10-12-38-26)14-18-6-8-24(35)42-28(18)30)43-32(3,4)21(33)15-39-29-25-19(9-11-37-25)13-17-5-7-23(34)41-27(17)29/h5-14,21-22,33,36H,15-16H2,1-4H3/t21-,22-/m1/s1

InChI Key

OIZNBPDWHFCLKY-FGZHOGPDSA-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
Heracleum candicans	LOTUS Database	35616633
Heracleum candicans WALL.	Plant	KNApSAcK
Pleurospermum rivulorum	LOTUS Database	35616633
Prangos pabularia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
Benzopyran
1-benzopyran
Benzofuran
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Tertiary alcohol
Lactone
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	4.03	ALOGPS
logP	3.48	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	147.03 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	152.82 m³·mol⁻¹	ChemAxon
Polarizability	58.55 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031179

Chemspider ID

8850276

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10674926

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Rivulobirin E (NP0071724)

MOL for NP0071724 (Rivulobirin E)

3D MOL for NP0071724 (Rivulobirin E)

3D SDF for NP0071724 (Rivulobirin E)

3D-SDF for NP0071724 (Rivulobirin E)

PDB for NP0071724 (Rivulobirin E)

3D PDB for NP0071724 (Rivulobirin E)

SMILES for NP0071724 (Rivulobirin E)

INCHI for NP0071724 (Rivulobirin E)

Structure for NP0071724 (Rivulobirin E)

3D Structure for NP0071724 (Rivulobirin E)