NP-MRD: Showing NP-Card for 6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one (NP0170437)

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Record Information

Version

2.0

Created at

2022-09-03 06:36:46 UTC

Updated at

2022-09-03 06:36:47 UTC

NP-MRD ID

NP0170437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one

Description

6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one is found in Physalis peruviana.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241219212D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241219212D          

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    3.6059    2.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1762    3.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6059    0.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910   -0.1231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 21  1  0  0  0  0
  6 37  2  0  0  0  0
  7  8  1  0  0  0  0
  7 20  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 22  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 23  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 24  1  0  0  0  0
 17 33  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 32  1  0  0  0  0
 26 27  1  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 36  2  0  0  0  0
 29 30  2  0  0  0  0
 29 34  1  0  0  0  0
 30 31  1  0  0  0  0
 30 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0170437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(Cl)C4(O)C(O)C=CC(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H39ClO8/c1-14-12-21(37-22(32)15(14)2)25(5,33)27(35)11-10-26(34)17-13-18(29)28(36)20(31)7-6-19(30)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-18,20-21,31,33-36H,8-13H2,1-5H3

> <INCHI_KEY>
XCJUXWOCLLPHII-UHFFFAOYSA-N

> <FORMULA>
C28H39ClO8

> <MOLECULAR_WEIGHT>
539.057

> <EXACT_MASS>
538.233345931

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
56.20061608441555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(1-{8-chloro-6,7,11,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.967502909666666

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.854174213049646

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.209889553495492

> <JCHEM_PKA_STRONGEST_BASIC>
-3.200135689470838

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
136.1804

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(1-{8-chloro-6,7,11,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.731  -2.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.731  -4.084   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.397  -4.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.065  -4.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.065  -2.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.397  -1.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.730  -4.855   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.399  -4.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.399  -2.541   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.730  -1.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.069  -1.773   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.069  -0.238   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.399   0.528   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.730  -0.238   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.388  -2.246   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.286  -1.004   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.388   0.233   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.397  -6.398   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.065  -5.627   0.000  0.00  0.00           O+0
HETATM   20 Cl   UNK     0      -2.730  -6.398   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0      -4.065  -1.004   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.069  -3.315   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.069   1.305   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.388   1.775   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.051   2.547   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.725   2.547   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.062   1.775   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.397   2.547   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.397   4.087   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.062   4.855   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.725   4.087   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.388   3.318   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.931   0.233   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.731   4.855   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.062   6.398   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.731   1.775   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -5.397  -0.230   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5    7   19                                             
CONECT    5    4    6   10   21                                             
CONECT    6    1    5   37                                                  
CONECT    7    4    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   22                                             
CONECT   12   11   13   17   23                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   24   33                                             
CONECT   18    3                                                            
CONECT   19    4                                                            
CONECT   20    7                                                            
CONECT   21    5                                                            
CONECT   22   11                                                            
CONECT   23   12                                                            
CONECT   24   17   25   26   32                                             
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   35                                                  
CONECT   31   26   30                                                       
CONECT   32   24                                                            
CONECT   33   17                                                            
CONECT   34   29                                                            
CONECT   35   30                                                            
CONECT   36   28                                                            
CONECT   37    6                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
Cytidine 5'-triphosphoric acid	Generator
6a-chloro-4b,5,14,17b,20S-Pentahydroxy-1-oxo-5b,22R-witha-2,24-dienolide	HMDB

Chemical Formula

C₂₈H₃₉ClO₈

Average Mass

539.0570 Da

Monoisotopic Mass

538.23335 Da

IUPAC Name

6-(1-{8-chloro-6,7,11,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

Traditional Name

6-(1-{8-chloro-6,7,11,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(Cl)C4(O)C(O)C=CC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H39ClO8/c1-14-12-21(37-22(32)15(14)2)25(5,33)27(35)11-10-26(34)17-13-18(29)28(36)20(31)7-6-19(30)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-18,20-21,31,33-36H,8-13H2,1-5H3

InChI Key

XCJUXWOCLLPHII-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
Physalis peruviana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine ribonucleoside triphosphates. These are pyrimidine ribobucleotides with triphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine ribonucleotides

Direct Parent

Pyrimidine ribonucleoside triphosphates

Alternative Parents

Substituents

Pyrimidine ribonucleoside triphosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Aminopyrimidine
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Imidolactam
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Amine
Alcohol
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.53	ALOGPS
logP	1.97	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.18 m³·mol⁻¹	ChemAxon
Polarizability	56.2 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012833

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

593

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one (NP0170437)

MOL for NP0170437 (6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D MOL for NP0170437 (6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D SDF for NP0170437 (6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D-SDF for NP0170437 (6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

PDB for NP0170437 (6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D PDB for NP0170437 (6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

SMILES for NP0170437 (6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

INCHI for NP0170437 (6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

Structure for NP0170437 (6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D Structure for NP0170437 (6-(1-{5-chloro-1,3a,5a,6-tetrahydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)