NP-MRD: Showing NP-Card for Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] (NP0141279)

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Record Information

Version

2.0

Created at

2022-06-29 22:42:41 UTC

Updated at

2022-06-29 22:42:41 UTC

NP-MRD ID

NP0141279

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside]

Description

9-(3-{[6-({[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxy-3-methylbutoxy)-7H-furo[3,2-g]chromen-7-one 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. Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] is found in Heracleum candicans. 9-(3-{[6-({[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxy-3-methylbutoxy)-7H-furo[3,2-g]chromen-7-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171507412D          

 42 46  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171507412D          

 42 46  0  0  0  0            999 V2000
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    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 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
 35 36  1  0  0  0  0
 30 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 29 42  2  0  0  0  0
 38 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141279

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(OC1OC(COC2OCC(O)(CO)C2O)C(O)C(O)C1O)C(O)COC1=C2OC=CC2=CC2=C1OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O15/c1-26(2,15(29)9-37-22-20-13(5-6-36-20)7-12-3-4-16(30)41-21(12)22)42-24-19(33)18(32)17(31)14(40-24)8-38-25-23(34)27(35,10-28)11-39-25/h3-7,14-15,17-19,23-25,28-29,31-35H,8-11H2,1-2H3

> <INCHI_KEY>
AGQARHVGJIEPHM-UHFFFAOYSA-N

> <FORMULA>
C27H34O15

> <MOLECULAR_WEIGHT>
598.554

> <EXACT_MASS>
598.189770395

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
58.327991187183656

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(3-{[6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxy-3-methylbutoxy)-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
-0.54

> <JCHEM_LOGP>
-1.8858082163333334

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.279735172507776

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.691804431424853

> <JCHEM_PKA_STRONGEST_BASIC>
-2.929380488964506

> <JCHEM_POLAR_SURFACE_AREA>
227.2

> <JCHEM_REFRACTIVITY>
137.24819999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(3-{[6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxy-3-methylbutoxy)furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.820   1.213   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.590   2.547   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.360   3.881   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.257   3.317   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.257   4.857   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.923   5.627   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.923   7.167   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.411   7.937   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.411   9.477   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.744  10.247   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.151   9.621   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.182  10.765   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.412  12.099   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.819  12.725   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.936  13.564   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.430  13.884   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.905  11.779   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.761  12.809   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.257   7.937   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.257   9.477   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.590   7.167   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924   7.937   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.590   5.627   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.924   4.857   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.258   2.547   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.925  -2.073   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.592  -2.073   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.459  -2.367   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   25                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   17                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   13   10   18                                                  
CONECT   18   17                                                            
CONECT   19    7   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    5   24                                                  
CONECT   24   23                                                            
CONECT   25    2   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   42                                                  
CONECT   30   29   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   30   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   42                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   29   38                                                  
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₅

Average Mass

598.5540 Da

Monoisotopic Mass

598.18977 Da

IUPAC Name

9-(3-{[6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxy-3-methylbutoxy)-7H-furo[3,2-g]chromen-7-one

Traditional Name

9-(3-{[6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-hydroxy-3-methylbutoxy)furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC(C)(OC1OC(COC2OCC(O)(CO)C2O)C(O)C(O)C1O)C(O)COC1=C2OC=CC2=CC2=C1OC(=O)C=C2

InChI Identifier

InChI=1S/C27H34O15/c1-26(2,15(29)9-37-22-20-13(5-6-36-20)7-12-3-4-16(30)41-21(12)22)42-24-19(33)18(32)17(31)14(40-24)8-38-25-23(34)27(35,10-28)11-39-25/h3-7,14-15,17-19,23-25,28-29,31-35H,8-11H2,1-2H3

InChI Key

AGQARHVGJIEPHM-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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

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
O-glycosyl compound
Glycosyl compound
Disaccharide
1-benzopyran
Benzopyran
Benzofuran
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Oxane
Furan
Tetrahydrofuran
Tertiary alcohol
Heteroaromatic compound
Lactone
Secondary alcohol
Acetal
Oxacycle
Ether
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
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	-0.54	ALOGPS
logP	-1.9	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	227.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	137.25 m³·mol⁻¹	ChemAxon
Polarizability	58.33 Å³	ChemAxon
Number of Rings	5	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

73088243

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] (NP0141279)

MOL for NP0141279 (Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside])

3D MOL for NP0141279 (Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside])

3D SDF for NP0141279 (Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside])

3D-SDF for NP0141279 (Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside])

PDB for NP0141279 (Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside])

3D PDB for NP0141279 (Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside])

SMILES for NP0141279 (Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside])

INCHI for NP0141279 (Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside])

Structure for NP0141279 (Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside])

3D Structure for NP0141279 (Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside])