NP-MRD: Showing NP-Card for (+)-Granatumin B (NP0081605)

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Record Information

Version

1.0

Created at

2022-04-29 02:36:55 UTC

Updated at

2022-04-29 02:36:55 UTC

NP-MRD ID

NP0081605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Granatumin B

Description

(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadeca-9,11-dien-14-yl (2S)-2-methylbutanoate belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (+)-Granatumin B is found in Xylocarpus granatum . Based on a literature review very few articles have been published on (1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadeca-9,11-dien-14-yl (2S)-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204362D          

 40 44  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292204362D          

 40 44  0  0  1  0            999 V2000
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    4.6856    4.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9906    4.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8312    5.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0505    5.3624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4525    5.6385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2931    6.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3467    2.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3958    3.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095    1.6013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428    0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7334    0.6612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0856    0.1993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8189   -0.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3617   -1.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8950    0.3587    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  1  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  0  0  0  0
 17 20  1  1  0  0  0
 16 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
  4 26  1  1  0  0  0
  3 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 32  1  0  0  0  0
  2 33  1  0  0  0  0
  1 34  1  6  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  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081605

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)O[C@@H]1[C@@H]2C=C3[C@H](CC[C@@]4(C)[C@@H](OC(=O)C=C34)C3=COC=C3)[C@](C)([C@@H](CC(=O)OC)C1(C)C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O8/c1-8-17(2)29(36)40-28-20-13-19-21(32(6,26(20)35)23(30(28,3)4)15-24(33)37-7)9-11-31(5)22(19)14-25(34)39-27(31)18-10-12-38-16-18/h10,12-14,16-17,20-21,23,27-28H,8-9,11,15H2,1-7H3/t17-,20+,21-,23-,27-,28+,31+,32+/m0/s1

> <INCHI_KEY>
JBVMJRIIFFXUFB-MDZWVGLPSA-N

> <FORMULA>
C32H40O8

> <MOLECULAR_WEIGHT>
552.664

> <EXACT_MASS>
552.272318248

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
59.474179292107614

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadeca-9,11-dien-14-yl (2S)-2-methylbutanoate

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
5.3976097733333335

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.833970092209206

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8888286851514224

> <JCHEM_POLAR_SURFACE_AREA>
109.11000000000001

> <JCHEM_REFRACTIVITY>
146.71050000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadeca-9,11-dien-14-yl (2S)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       9.831   4.149   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.515   5.529   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.023   6.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.643   7.672   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.184   7.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.500   5.800   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.992   4.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.372   3.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.009   5.630   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.191   4.643   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.963   5.702   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.279   4.322   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.742   4.224   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.059   2.844   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.889   5.506   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.573   6.886   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.110   6.984   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.794   8.364   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.331   8.462   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.257   8.266   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.720   8.168   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.181   8.232   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.234   9.715   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.048  10.568   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.256   9.612   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.747   9.208   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.183   8.001   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.885   9.512   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.428  10.010   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      12.045  10.525   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.747  12.036   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.847   4.756   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.939   6.115   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.844   2.989   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.347   1.532   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.836   1.234   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      11.360   0.372   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.862  -1.085   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.875  -2.245   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.871   0.670   0.000  0.00  0.00           C+0
CONECT    1    2    8   34                                                  
CONECT    2    1    3   32   33                                             
CONECT    3    2    4   27                                                  
CONECT    4    3    5    9   26                                             
CONECT    5    4    6   19                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    1    9                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    6   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   11   18   20                                             
CONECT   18   17   19                                                       
CONECT   19   18    5                                                       
CONECT   20   17                                                            
CONECT   21   16   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21                                                       
CONECT   26    4                                                            
CONECT   27    3   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32    2                                                            
CONECT   33    2                                                            
CONECT   34    1   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,5R,6R,13S,14R,16S)-6-(Furan-3-yl)-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0,.0,]heptadeca-9,11-dien-14-yl (2S)-2-methylbutanoic acid	Generator

Chemical Formula

C₃₂H₄₀O₈

Average Mass

552.6640 Da

Monoisotopic Mass

552.27232 Da

IUPAC Name

(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadeca-9,11-dien-14-yl (2S)-2-methylbutanoate

Traditional Name

(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadeca-9,11-dien-14-yl (2S)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)O[C@@H]1[C@@H]2C=C3[C@H](CC[C@@]4(C)[C@@H](OC(=O)C=C34)C3=COC=C3)[C@](C)([C@@H](CC(=O)OC)C1(C)C)C2=O

InChI Identifier

InChI=1S/C32H40O8/c1-8-17(2)29(36)40-28-20-13-19-21(32(6,26(20)35)23(30(28,3)4)15-24(33)37-7)9-11-31(5)22(19)14-25(34)39-27(31)18-10-12-38-16-18/h10,12-14,16-17,20-21,23,27-28H,8-9,11,15H2,1-7H3/t17-,20+,21-,23-,27-,28+,31+,32+/m0/s1

InChI Key

JBVMJRIIFFXUFB-MDZWVGLPSA-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
Xylocarpus granatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Dihydropyranone
Fatty acid ester
Cyclohexenone
Pyran
Fatty acyl
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	4.21	ALOGPS
logP	5.4	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.83	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	109.11 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	146.71 m³·mol⁻¹	ChemAxon
Polarizability	59.47 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

27024645

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44614010

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Granatumin B (NP0081605)

MOL for NP0081605 ((+)-Granatumin B)

3D MOL for NP0081605 ((+)-Granatumin B)

3D SDF for NP0081605 ((+)-Granatumin B)

3D-SDF for NP0081605 ((+)-Granatumin B)

PDB for NP0081605 ((+)-Granatumin B)

3D PDB for NP0081605 ((+)-Granatumin B)

SMILES for NP0081605 ((+)-Granatumin B)

INCHI for NP0081605 ((+)-Granatumin B)

Structure for NP0081605 ((+)-Granatumin B)

3D Structure for NP0081605 ((+)-Granatumin B)