NP-MRD: Showing NP-Card for (-)-Dahuribirin A (NP0072832)

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Record Information

Version

2.0

Created at

2022-04-28 18:06:55 UTC

Updated at

2022-04-28 18:06:55 UTC

NP-MRD ID

NP0072832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Dahuribirin A

Description

Dahuribirin A 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 A is found in Angelica dahurica and Angelica dahurica BENTH et HOOK.var.dahurica BENTH.et HOOK. . Based on a literature review very few articles have been published on Dahuribirin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220062D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282220062D          

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   -3.4022    3.5981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6877    4.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9733    5.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5443    6.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1701    6.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9548    5.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4397    4.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9548    3.7557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5597   -2.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2741   -1.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1026   -0.9826    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  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  4 16  1  0  0  0  0
 14 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 18 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 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
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 29 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 27 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 26 40  1  0  0  0  0
  2 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
  1 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=COC2=C(OC[C@H]2O[C@@]3(OC2(C)C)OC2=C(C=C3)C=C3C=COC3=C2OCC=C(C)C)C2=C1C=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C33H30O10/c1-18(2)9-13-38-30-25-20(10-14-36-25)16-19-8-12-33(42-26(19)30)41-23(32(3,4)43-33)17-39-31-28-22(11-15-37-28)27(35-5)21-6-7-24(34)40-29(21)31/h6-12,14-16,23H,13,17H2,1-5H3/t23-,33-/m1/s1

> <INCHI_KEY>
HCKXEUGWKJVWHW-PVAZPRTOSA-N

> <FORMULA>
C33H30O10

> <MOLECULAR_WEIGHT>
586.593

> <EXACT_MASS>
586.183897166

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
61.62210368609991

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-{[(2S,5R)-4,4-dimethyl-9'-[(3-methylbut-2-en-1-yl)oxy]spiro[1,3-dioxolane-2,7'-furo[3,2-g]chromene]-5-yl]methoxy}-4-methoxy-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
6.120697712

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5752555417118526

> <JCHEM_POLAR_SURFACE_AREA>
107.96000000000002

> <JCHEM_REFRACTIVITY>
156.80429999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-[(2S,5R)-4,4-dimethyl-9'-[(3-methylbut-2-en-1-yl)oxy]spiro[1,3-dioxolane-2,7'-furo[3,2-g]chromene]-5-ylmethoxy]-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      -7.993  -1.673   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.367  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.835  -3.241   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.930  -1.995   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.557  -0.588   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.088  -0.427   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.714   0.980   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -9.246   1.141   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.872   2.547   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.967   3.793   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.594   5.200   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.436   3.632   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.651   0.658   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.120   0.497   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.493  -0.910   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.399  -2.156   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.596   1.961   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.350   2.867   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.104   1.961   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.580   0.497   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.061   3.095   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.406   1.657   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.350   4.407   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.016   5.177   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.016   6.717   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.318   7.487   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.318   9.027   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.016   9.797   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.350   9.027   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.350   7.487   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.683   6.717   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.017   7.487   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.351   6.717   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -5.017   9.027   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.683   9.797   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.016  11.337   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.318  12.107   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.782   9.502   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.687   8.257   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.782   7.011   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -8.511  -4.110   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -9.845  -3.340   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -9.525  -1.834   0.000  0.00  0.00           O+0
CONECT    1    2    6   43                                                  
CONECT    2    1    3   41                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15   17   20                                             
CONECT   15   14   16                                                       
CONECT   16   15    4                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21   22                                             
CONECT   20   19   14                                                       
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   40                                                  
CONECT   27   26   28   38                                                  
CONECT   28   27   29   36                                                  
CONECT   29   28   30   35                                                  
CONECT   30   29   25   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29                                                       
CONECT   36   28   37                                                       
CONECT   37   36                                                            
CONECT   38   27   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   26                                                       
CONECT   41    2   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42    1                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₀O₁₀

Average Mass

586.5930 Da

Monoisotopic Mass

586.18390 Da

IUPAC Name

9-{[(2S,5R)-4,4-dimethyl-9'-[(3-methylbut-2-en-1-yl)oxy]spiro[1,3-dioxolane-2,7'-furo[3,2-g]chromene]-5-yl]methoxy}-4-methoxy-7H-furo[3,2-g]chromen-7-one

Traditional Name

9-[(2S,5R)-4,4-dimethyl-9'-[(3-methylbut-2-en-1-yl)oxy]spiro[1,3-dioxolane-2,7'-furo[3,2-g]chromene]-5-ylmethoxy]-4-methoxyfuro[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

COC1=C2C=COC2=C(OC[C@H]2O[C@@]3(OC2(C)C)OC2=C(C=C3)C=C3C=COC3=C2OCC=C(C)C)C2=C1C=CC(=O)O2

InChI Identifier

InChI=1S/C33H30O10/c1-18(2)9-13-38-30-25-20(10-14-36-25)16-19-8-12-33(42-26(19)30)41-23(32(3,4)43-33)17-39-31-28-22(11-15-37-28)27(35-5)21-6-7-24(34)40-29(21)31/h6-12,14-16,23H,13,17H2,1-5H3/t23-,33-/m1/s1

InChI Key

HCKXEUGWKJVWHW-PVAZPRTOSA-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	LOTUS Database	35616633
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
Benzopyran
1-benzopyran
Benzofuran
Anisole
Phenol ether
Alkyl aryl ether
Carboxylic acid orthoester
Ortho ester
Pyranone
Pyran
Benzenoid
Meta-dioxolane
Furan
Heteroaromatic compound
Orthocarboxylic acid derivative
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	5.4	ALOGPS
logP	6.12	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	107.96 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	156.8 m³·mol⁻¹	ChemAxon
Polarizability	61.62 Å³	ChemAxon
Number of Rings	7	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

C00032882

Chemspider ID

9192560

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11017376

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Dahuribirin A (NP0072832)

MOL for NP0072832 ((-)-Dahuribirin A)

3D MOL for NP0072832 ((-)-Dahuribirin A)

3D SDF for NP0072832 ((-)-Dahuribirin A)

3D-SDF for NP0072832 ((-)-Dahuribirin A)

PDB for NP0072832 ((-)-Dahuribirin A)

3D PDB for NP0072832 ((-)-Dahuribirin A)

SMILES for NP0072832 ((-)-Dahuribirin A)

INCHI for NP0072832 ((-)-Dahuribirin A)

Structure for NP0072832 ((-)-Dahuribirin A)

3D Structure for NP0072832 ((-)-Dahuribirin A)