NP-MRD: Showing NP-Card for Podolactone A (NP0050245)

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Record Information

Version

2.0

Created at

2022-04-27 20:49:43 UTC

Updated at

2022-04-27 20:49:43 UTC

NP-MRD ID

NP0050245

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Podolactone A

Description

(1S,2R,4S,5R,10S,12S,14R,15R,18R)-5-[(2S)-1,2-dihydroxypropan-2-yl]-10,15-dimethyl-3,6,13,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹²,¹⁴.0¹⁵,¹⁸]Octadec-8-ene-7,16-dione 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. Podolactone A is found in Podocarpus milanjianus and Podocarpus neriifolius . Based on a literature review very few articles have been published on (1S,2R,4S,5R,10S,12S,14R,15R,18R)-5-[(2S)-1,2-dihydroxypropan-2-yl]-10,15-dimethyl-3,6,13,17-tetraoxahexacyclo[8.7.1.0²,⁴.0⁴,⁹.0¹²,¹⁴.0¹⁵,¹⁸]Octadec-8-ene-7,16-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222492D          

 27 32  0  0  1  0            999 V2000
    2.9600    1.3554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2662    2.1214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7558    2.7696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9393    2.6518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6331    1.8857    0.0000 C   0  0  2  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
    0.8165    1.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6124    0.1179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165    1.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5103    2.2982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3062    2.4161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6124    3.1821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8877    3.9857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6816    3.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3205    4.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041    3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0207    2.9464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5310    3.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475    3.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3725    3.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    2.4361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269    1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247    3.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7765    1.4732    0.0000 O   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 14 19  1  6  0  0  0
 13 19  1  6  0  0  0
 12 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  6  0  0  0
 20 24  1  6  0  0  0
  5 25  1  1  0  0  0
  3 26  1  6  0  0  0
  2 27  1  1  0  0  0
  1 27  1  1  0  0  0
M  END


  Mrv1652304272222492D          

 27 32  0  0  1  0            999 V2000
    2.9600    1.3554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2662    2.1214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7558    2.7696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9393    2.6518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6331    1.8857    0.0000 C   0  0  2  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
    0.8165    1.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6124    0.1179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165    1.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5103    2.2982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3062    2.4161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6124    3.1821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8877    3.9857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6816    3.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3205    4.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041    3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0207    2.9464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5310    3.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3475    3.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3725    3.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    2.4361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269    1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247    3.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7765    1.4732    0.0000 O   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 14 19  1  6  0  0  0
 13 19  1  6  0  0  0
 12 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  6  0  0  0
 20 24  1  6  0  0  0
  5 25  1  1  0  0  0
  3 26  1  6  0  0  0
  2 27  1  1  0  0  0
  1 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050245

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@](O)(CO)[C@H]1OC(=O)C=C2[C@@]11O[C@@H]1[C@H]1OC(=O)[C@@]3(C)[C@H]4O[C@H]4C[C@@]2(C)[C@@H]13

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O8/c1-16-5-7-12(24-7)18(3)11(16)10(26-15(18)22)13-19(27-13)8(16)4-9(21)25-14(19)17(2,23)6-20/h4,7,10-14,20,23H,5-6H2,1-3H3/t7-,10-,11+,12-,13+,14+,16+,17-,18+,19-/m0/s1

> <INCHI_KEY>
UOYUIWWYLLWSMC-CBUYMQHQSA-N

> <FORMULA>
C19H22O8

> <MOLECULAR_WEIGHT>
378.377

> <EXACT_MASS>
378.131467668

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.53739906356695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4S,5R,10S,12S,14R,15R,18R)-5-[(2S)-1,2-dihydroxypropan-2-yl]-10,15-dimethyl-3,6,13,17-tetraoxahexacyclo[8.7.1.0^{2,4}.0^{4,9}.0^{12,14}.0^{15,18}]octadec-8-ene-7,16-dione

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
-0.357943804999999

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.170613248771495

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.14166598731044

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1062221996327812

> <JCHEM_POLAR_SURFACE_AREA>
114.82000000000001

> <JCHEM_REFRACTIVITY>
86.73970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,5R,10S,12S,14R,15R,18R)-5-[(2S)-1,2-dihydroxypropan-2-yl]-10,15-dimethyl-3,6,13,17-tetraoxahexacyclo[8.7.1.0^{2,4}.0^{4,9}.0^{12,14}.0^{15,18}]octadec-8-ene-7,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       5.525   2.530   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.097   3.960   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.144   5.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.620   4.950   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.048   3.520   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.524   3.300   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.953   1.870   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.572   1.650   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.143   0.220   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.524   2.860   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.953   4.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.572   4.510   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.143   5.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.524   7.440   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.006   7.021   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.198   7.995   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.381   5.720   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.905   5.500   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.858   6.710   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.382   6.490   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.695   6.453   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.115   4.547   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.477   2.090   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.580   5.728   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.049   2.750   0.000  0.00  0.00           O+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4   17   26                                             
CONECT    4    3    5   15                                                  
CONECT    5    4    6    7   25                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12    7   14   19                                             
CONECT   14   13   15   19                                                  
CONECT   15   14    4   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    3   18                                                  
CONECT   18   17                                                            
CONECT   19   14   13                                                       
CONECT   20   12   21   23   24                                             
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24   20                                                            
CONECT   25    5                                                            
CONECT   26    3                                                            
CONECT   27    2    1                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₈

Average Mass

378.3770 Da

Monoisotopic Mass

378.13147 Da

IUPAC Name

(1S,2R,4S,5R,10S,12S,14R,15R,18R)-5-[(2S)-1,2-dihydroxypropan-2-yl]-10,15-dimethyl-3,6,13,17-tetraoxahexacyclo[8.7.1.0^{2,4}.0^{4,9}.0^{12,14}.0^{15,18}]octadec-8-ene-7,16-dione

Traditional Name

(1S,2R,4S,5R,10S,12S,14R,15R,18R)-5-[(2S)-1,2-dihydroxypropan-2-yl]-10,15-dimethyl-3,6,13,17-tetraoxahexacyclo[8.7.1.0^{2,4}.0^{4,9}.0^{12,14}.0^{15,18}]octadec-8-ene-7,16-dione

CAS Registry Number

Not Available

SMILES

C[C@](O)(CO)[C@H]1OC(=O)C=C2[C@@]11O[C@@H]1[C@H]1OC(=O)[C@@]3(C)[C@H]4O[C@H]4C[C@@]2(C)[C@@H]13

InChI Identifier

InChI=1S/C19H22O8/c1-16-5-7-12(24-7)18(3)11(16)10(26-15(18)22)13-19(27-13)8(16)4-9(21)25-14(19)17(2,23)6-20/h4,7,10-14,20,23H,5-6H2,1-3H3/t7-,10-,11+,12-,13+,14+,16+,17-,18+,19-/m0/s1

InChI Key

UOYUIWWYLLWSMC-CBUYMQHQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Podocarpus milanjianus	Plant	KNApSAcK
Podocarpus neriifolius	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
Dihydropyranone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Tertiary alcohol
Carboxylic acid ester
1,2-diol
Lactone
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Primary alcohol
Alcohol
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.52	ALOGPS
logP	-0.36	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	13.14	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.74 m³·mol⁻¹	ChemAxon
Polarizability	36.54 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

101289543

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Podolactone A (NP0050245)

MOL for NP0050245 (Podolactone A)

3D MOL for NP0050245 (Podolactone A)

3D SDF for NP0050245 (Podolactone A)

3D-SDF for NP0050245 (Podolactone A)

PDB for NP0050245 (Podolactone A)

3D PDB for NP0050245 (Podolactone A)

SMILES for NP0050245 (Podolactone A)

INCHI for NP0050245 (Podolactone A)

Structure for NP0050245 (Podolactone A)

3D Structure for NP0050245 (Podolactone A)