NP-MRD: Showing NP-Card for Dahuribirin F (NP0072835)

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Record Information

Version

2.0

Created at

2022-04-28 18:07:04 UTC

Updated at

2022-04-28 18:07:04 UTC

NP-MRD ID

NP0072835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dahuribirin F

Description

9-[(2S)-2-hydroxy-3-methyl-3-{[(2S)-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)but-3-en-2-yl]oxy}butoxy]-4-methoxy-7H-furo[3,2-g]chromen-7-one belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group. Dahuribirin F is found in Angelica dahurica BENTH et HOOK.var.dahurica BENTH.et HOOK. . Based on a literature review very few articles have been published on 9-[(2S)-2-hydroxy-3-methyl-3-{[(2S)-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)but-3-en-2-yl]oxy}butoxy]-4-methoxy-7H-furo[3,2-g]chromen-7-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220072D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282220072D          

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    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
  1 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 32 38  1  0  0  0  0
 30 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 29 41  1  0  0  0  0
 20 42  1  0  0  0  0
 20 43  1  0  0  0  0
 19 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0072835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=COC2=C(OC[C@H](O)C(C)(C)O[C@H](COC2=C3OC=CC3=CC3=C2OC(=O)C=C3)C(C)=C)C2=C1C=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C33H30O11/c1-17(2)22(15-40-31-26-19(10-12-38-26)14-18-6-8-24(35)42-27(18)31)44-33(3,4)23(34)16-41-32-29-21(11-13-39-29)28(37-5)20-7-9-25(36)43-30(20)32/h6-14,22-23,34H,1,15-16H2,2-5H3/t22-,23+/m1/s1

> <INCHI_KEY>
GQNLCPKYTWCUAR-PKTZIBPZSA-N

> <FORMULA>
C33H30O11

> <MOLECULAR_WEIGHT>
602.592

> <EXACT_MASS>
602.178811786

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
61.655910776138626

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(2S)-2-hydroxy-3-methyl-3-{[(2S)-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)but-3-en-2-yl]oxy}butoxy]-4-methoxy-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
4.55

> <JCHEM_LOGP>
4.294646699333334

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.224436228721427

> <JCHEM_PKA_STRONGEST_BASIC>
-2.58406360971304

> <JCHEM_POLAR_SURFACE_AREA>
136.03000000000003

> <JCHEM_REFRACTIVITY>
157.37789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-[(2S)-2-hydroxy-3-methyl-3-{[(2S)-3-methyl-1-({7-oxofuro[3,2-g]chromen-9-yl}oxy)but-3-en-2-yl]oxy}butoxy]-4-methoxyfuro[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       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336 -13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003 -13.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669 -10.780   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.003  -8.470   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337 -10.780   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.670 -13.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.349 -15.366   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.818 -15.527   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.191 -14.120   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002 -10.780   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.208  -6.930   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.128  -6.930   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    4   13                                                       
CONECT   13   12                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2                                                       
CONECT   17    1   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   44                                                  
CONECT   20   19   21   42   43                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   41                                                  
CONECT   30   29   31   39                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   28   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   32                                                       
CONECT   39   30   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   29                                                       
CONECT   42   20                                                            
CONECT   43   20                                                            
CONECT   44   19                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₀O₁₁

Average Mass

602.5920 Da

Monoisotopic Mass

602.17881 Da

IUPAC Name

9-[(2S)-2-hydroxy-3-methyl-3-{[(2S)-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)but-3-en-2-yl]oxy}butoxy]-4-methoxy-7H-furo[3,2-g]chromen-7-one

Traditional Name

9-[(2S)-2-hydroxy-3-methyl-3-{[(2S)-3-methyl-1-({7-oxofuro[3,2-g]chromen-9-yl}oxy)but-3-en-2-yl]oxy}butoxy]-4-methoxyfuro[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

COC1=C2C=COC2=C(OC[C@H](O)C(C)(C)O[C@H](COC2=C3OC=CC3=CC3=C2OC(=O)C=C3)C(C)=C)C2=C1C=CC(=O)O2

InChI Identifier

InChI=1S/C33H30O11/c1-17(2)22(15-40-31-26-19(10-12-38-26)14-18-6-8-24(35)42-27(18)31)44-33(3,4)23(34)16-41-32-29-21(11-13-39-29)28(37-5)20-7-9-25(36)43-30(20)32/h6-14,22-23,34H,1,15-16H2,2-5H3/t22-,23+/m1/s1

InChI Key

GQNLCPKYTWCUAR-PKTZIBPZSA-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
Angelica dahurica BENTH et HOOK.var.dahurica BENTH.et HOOK.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

5-methoxypsoralens

Alternative Parents

Substituents

5-methoxypsoralen
1-benzopyran
Benzopyran
Benzofuran
Anisole
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Furan
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	4.55	ALOGPS
logP	4.29	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.22	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	136.03 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	157.38 m³·mol⁻¹	ChemAxon
Polarizability	61.66 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

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

163104179

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dahuribirin F (NP0072835)

MOL for NP0072835 (Dahuribirin F)

3D MOL for NP0072835 (Dahuribirin F)

3D SDF for NP0072835 (Dahuribirin F)

3D-SDF for NP0072835 (Dahuribirin F)

PDB for NP0072835 (Dahuribirin F)

3D PDB for NP0072835 (Dahuribirin F)

SMILES for NP0072835 (Dahuribirin F)

INCHI for NP0072835 (Dahuribirin F)

Structure for NP0072835 (Dahuribirin F)

3D Structure for NP0072835 (Dahuribirin F)