NP-MRD: Showing NP-Card for Podocarpic acid (NP0052043)

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Record Information

Version

2.0

Created at

2022-04-27 23:13:36 UTC

Updated at

2022-04-27 23:13:36 UTC

NP-MRD ID

NP0052043

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Podocarpic acid

Description

Podocarpic acid, also known as podocarpate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Podocarpic acid is found in Dacrycarpus dacrydioides, Dacrydium cupressinum , Falcatifolium taxoides, Ferula pseudooreoselinum, Nageia wallichiana, Podocarpus cupressina, Podocarpus dacrydiodes, Podocarpus dacrydioides , Podocarpus fasciculus and Podocarpus totara . Podocarpic acid was first documented in 2010 (PMID: 21067932). Based on a literature review a significant number of articles have been published on podocarpic acid (PMID: 33826808) (PMID: 32248592) (PMID: 27773573) (PMID: 27711326) (PMID: 27617995) (PMID: 26938881).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -3.0473    0.2423    1.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1743    0.3415   -0.0191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4197    1.7112   -0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    1.8752   -1.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1384    2.8541    0.1704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6225   -0.7302   -0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004   -1.3283   -1.8160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -1.5133   -1.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138   -0.2036   -0.6228 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3542    0.8221   -1.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440   -0.3624    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5608   -0.9340   -0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8294   -1.1391   -0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8540   -1.7043   -0.9834 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0571   -0.7445    1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837   -0.1844    1.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8105    0.0136    1.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654    0.6402    2.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2759    1.2444    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653    0.1230    0.4493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1602    1.2204    1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5727   -0.4465    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0431   -0.1727    0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7210    3.2264    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4297   -0.2931   -1.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652   -1.5478   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9668   -2.3618   -2.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4990   -0.8222   -2.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4402   -1.8321   -2.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200   -2.2937   -0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026    1.8031   -1.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768    0.5399   -2.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    0.8753   -2.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702   -1.2414   -1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4896   -1.1314   -1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589   -0.9066    1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2728    0.1233    2.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3226   -0.1320    2.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461    1.4678    2.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2275    2.0469    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1426    1.6476    1.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135   -0.7933    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
  9 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
 20  2  1  0
 16 17  1  0
 11  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 20 42  1  1
 19 40  1  0
 19 41  1  0
 18 38  1  0
 18 39  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
  5 24  1  0
M  END

  Mrv1652304282201132D          

 20 22  0  0  1  0            999 V2000
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3016   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0300   -0.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2728   -1.5637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308   -1.1265    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  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  1  0  0  0  0
  4 10  1  6  0  0  0
  8 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
  7 14  1  0  0  0  0
 13 15  1  0  0  0  0
  5 16  1  6  0  0  0
  3 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  3 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0052043

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(CCC[C@@]2(C)[C@H]1CCC1=C2C=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O3/c1-16-8-3-9-17(2,15(19)20)14(16)7-5-11-4-6-12(18)10-13(11)16/h4,6,10,14,18H,3,5,7-9H2,1-2H3,(H,19,20)/t14-,16-,17+/m1/s1

> <INCHI_KEY>
VJILEYKNALCDDV-OIISXLGYSA-N

> <FORMULA>
C17H22O3

> <MOLECULAR_WEIGHT>
274.36

> <EXACT_MASS>
274.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.385568256550915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aS,10aR)-6-hydroxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
4.2001902556666675

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.749179777674003

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.446169185186437

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9284979860817595

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
77.23409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
podocarpic acid

> <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       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.030  -1.380   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.389  -0.657   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.976  -2.919   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.777  -2.103   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17   20                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   16                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    7                                                       
CONECT   15   13                                                            
CONECT   16    5                                                            
CONECT   17    3   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    3                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(1S,4AS,10ar)-1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy-1,4a-dimethylphenanthrene-1-carboxylic acid	ChEBI
(1S,4AS,10ar)-6-hydroxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid	ChEBI
(1S,4AS,10ar)-1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy-1,4a-dimethylphenanthrene-1-carboxylate	Generator
(1S,4AS,10ar)-6-hydroxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate	Generator
Podocarpate	Generator

Chemical Formula

C₁₇H₂₂O₃

Average Mass

274.3600 Da

Monoisotopic Mass

274.15689 Da

IUPAC Name

(1S,4aS,10aR)-6-hydroxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

Traditional Name

podocarpic acid

CAS Registry Number

Not Available

SMILES

C[C@@]1(CCC[C@@]2(C)[C@H]1CCC1=C2C=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C17H22O3/c1-16-8-3-9-17(2,15(19)20)14(16)7-5-11-4-6-12(18)10-13(11)16/h4,6,10,14,18H,3,5,7-9H2,1-2H3,(H,19,20)/t14-,16-,17+/m1/s1

InChI Key

VJILEYKNALCDDV-OIISXLGYSA-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
Dacrycarpus dacrydioides	LOTUS Database	35616633
Dacrydium cupressinum	Plant	KNApSAcK
Falcatifolium taxoides	Plant	KNApSAcK
Ferula sumbul	Plant	KNApSAcK
Nageia wallichiana	LOTUS Database	35616633
Podocarpus cupressina	Plant	KNApSAcK
Podocarpus dacrydiodes	Plant	KNApSAcK
Podocarpus dacrydioides	Plant	KNApSAcK
Podocarpus fasciculus	Plant	KNApSAcK
Podocarpus totara	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Phenanthrene
Hydrophenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

abietane diterpenoid (CHEBI:8277 )
Podocarpane diterpenoids (C09171 )
Podocarpanes (C09171 )
Podocarpane diterpenoids (LMPR0104120002 )

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	4.13	ALOGPS
logP	4.2	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.23 m³·mol⁻¹	ChemAxon
Polarizability	30.39 Å³	ChemAxon
Number of Rings	3	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

C00003474

Chemspider ID

83970

KEGG Compound ID

C09171

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

93017

PDB ID

Not Available

ChEBI ID

8277

Good Scents ID

Not Available

References

General References

Shahinozzaman M, Islam M, Basak B, Sultana A, Emran R, Ashrafizadeh M, Islam ATMR: A review on chemistry, source and therapeutic potential of lambertianic acid. Z Naturforsch C J Biosci. 2021 Apr 8;76(9-10):347-356. doi: 10.1515/znc-2020-0267. Print 2021 Sep 27. [PubMed:33826808 ]
He H, Zhao R, Hu K, Qiu L, Ding W, Li Y: A novel negative thermotaxis behavior in rice planthoppers is regulated by TRPA1 channel. Pest Manag Sci. 2020 Sep;76(9):3003-3011. doi: 10.1002/ps.5846. Epub 2020 Apr 27. [PubMed:32248592 ]
Chaudhuri J, Bose N, Gong J, Hall D, Rifkind A, Bhaumik D, Peiris TH, Chamoli M, Le CH, Liu J, Lithgow GJ, Ramanathan A, Xu XZS, Kapahi P: A Caenorhabditis elegans Model Elucidates a Conserved Role for TRPA1-Nrf Signaling in Reactive alpha-Dicarbonyl Detoxification. Curr Biol. 2016 Nov 21;26(22):3014-3025. doi: 10.1016/j.cub.2016.09.024. Epub 2016 Oct 20. [PubMed:27773573 ]
Li FZ, Li S, Zhang PP, Huang ZH, Zhang WB, Gong J, Yang Z: A chiral pool approach for asymmetric syntheses of (-)-antrocin, (+)-asperolide C, and (-)-trans-ozic acid. Chem Commun (Camb). 2016 Oct 13;52(84):12426-12429. doi: 10.1039/c6cc06794h. [PubMed:27711326 ]
La Bella A, Leonelli F, Migneco LM, Marini Bettolo R: (+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids dagger. Molecules. 2016 Sep 8;21(9). pii: molecules21091197. doi: 10.3390/molecules21091197. [PubMed:27617995 ]
Leonelli F, Mostarda A, De Angelis L, Lamba D, Demitri N, La Bella A, Ceccacci F, Migneco LM, Marini Bettolo R: Proof of the Structure of the Stemodia chilensis Tetracyclic Diterpenoid (+)-19-Acetoxystemodan-12-ol by Synthesis from (+)-Podocarpic Acid: X-ray Structure Determination of a Key Intermediate. J Nat Prod. 2016 Apr 22;79(4):1155-9. doi: 10.1021/acs.jnatprod.5b00834. Epub 2016 Mar 3. [PubMed:26938881 ]
Dang Z, Jung K, Zhu L, Xie H, Lee KH, Chen CH, Huang L: Phenolic diterpenoid derivatives as anti-influenza a virus agents. ACS Med Chem Lett. 2015 Jan 29;6(3):355-8. doi: 10.1021/ml500533x. eCollection 2015 Mar 12. [PubMed:25815159 ]
Leonelli F, Latini V, Trombetta A, Bartoli G, Ceccacci F, La Bella A, Sferrazza A, Lamba D, Migneco LM, Bettolo RM: Regio- and diastereoselective synthesis and X-ray structure determination of (+)-2-deoxyoryzalexin S from (+)-podocarpic acid. Structural nonidentity with its nominal natural isolated enantiomer. J Nat Prod. 2012 Nov 26;75(11):1944-50. doi: 10.1021/np300518j. Epub 2012 Oct 23. [PubMed:23088775 ]
Cui YM, Yasutomi E, Otani Y, Ido K, Yoshinaga T, Sawada K, Ohwada T: Design, synthesis, and characterization of BK channel openers based on oximation of abietane diterpene derivatives. Bioorg Med Chem. 2010 Dec 15;18(24):8642-59. doi: 10.1016/j.bmc.2010.09.072. Epub 2010 Nov 8. [PubMed:21067932 ]
Baraka HN: Microbial transformation of podocarpic acid and evaluation of transformation products for antioxidant activity. Planta Med. 2010 May;76(8):815-7. doi: 10.1055/s-0029-1240738. Epub 2010 Jan 12. [PubMed:20072957 ]

Showing NP-Card for Podocarpic acid (NP0052043)

MOL for NP0052043 (Podocarpic acid)

3D MOL for NP0052043 (Podocarpic acid)

3D SDF for NP0052043 (Podocarpic acid)

3D-SDF for NP0052043 (Podocarpic acid)

PDB for NP0052043 (Podocarpic acid)

3D PDB for NP0052043 (Podocarpic acid)

SMILES for NP0052043 (Podocarpic acid)

INCHI for NP0052043 (Podocarpic acid)

Structure for NP0052043 (Podocarpic acid)

3D Structure for NP0052043 (Podocarpic acid)