NP-MRD: Showing NP-Card for (+)-Plantagiolide D (NP0071645)

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Record Information

Version

2.0

Created at

2022-04-28 16:59:50 UTC

Updated at

2022-04-28 16:59:50 UTC

NP-MRD ID

NP0071645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Plantagiolide D

Description

Plantagiolide D belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. (+)-Plantagiolide D is found in Tacca plantaginea and Tacca plantaginea (HANCE). Based on a literature review very few articles have been published on Plantagiolide D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218592D          

 42 48  0  0  1  0            999 V2000
    4.2818    1.8551    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5062    1.0612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282218592D          

 42 48  0  0  1  0            999 V2000
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    1.0829    2.6656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8826    2.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8585    3.4595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338    4.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2094    4.8447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2335    3.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169    2.1062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6020    1.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7756    2.7919    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5988    2.7375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9633    1.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865    1.9430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2452    2.6287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8807    3.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3395    4.0545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0575    3.4232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0684    2.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7608    1.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4557    1.4606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111    3.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014    2.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6823    2.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3555   -0.1213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0815    1.6525    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
  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
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 13 15  1  1  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 16 26  1  6  0  0  0
 24 27  1  6  0  0  0
 28 27  1  1  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
 28 34  1  0  0  0  0
 31 35  1  1  0  0  0
 30 36  1  6  0  0  0
 30 37  1  1  0  0  0
 27 38  1  1  0  0  0
 17 39  1  6  0  0  0
  5 40  1  6  0  0  0
  4 41  1  1  0  0  0
  2 42  1  1  0  0  0
  1 42  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0071645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1CC[C@H]2[C@@H]3[C@@H]4O[C@@H]4[C@@]4(O)C[C@@H]5O[C@@H]5[C@H](OC(C)=O)[C@]4(C)[C@H]3C[C@H](OC(C)=O)[C@]12C)[C@H]1C[C@@](C)(O)[C@@H](C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O10/c1-13(20-11-29(5,36)14(2)28(35)41-20)17-8-9-18-23-19(10-22(30(17,18)6)38-15(3)33)31(7)26(39-16(4)34)24-21(40-24)12-32(31,37)27-25(23)42-27/h13-14,17-27,36-37H,8-12H2,1-7H3/t13-,14-,17+,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-,29+,30+,31-,32-/m0/s1

> <INCHI_KEY>
UBZJVFYBDALJKJ-VNYRJWHDSA-N

> <FORMULA>
C32H46O10

> <MOLECULAR_WEIGHT>
590.71

> <EXACT_MASS>
590.309097681

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
62.82384013829312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,5R,7S,9S,10R,11S,12S,14S,15R,16R,19S)-14-(acetyloxy)-5-hydroxy-16-[(1S)-1-[(2R,4R,5R)-4-hydroxy-4,5-dimethyl-6-oxooxan-2-yl]ethyl]-11,15-dimethyl-3,8-dioxahexacyclo[10.7.0.0^{2,4}.0^{5,11}.0^{7,9}.0^{15,19}]nonadecan-10-yl acetate

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
1.4638717413333338

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.475714923168624

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.186547598160736

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0387352090414224

> <JCHEM_POLAR_SURFACE_AREA>
141.11999999999998

> <JCHEM_REFRACTIVITY>
145.16600000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5R,7S,9S,10R,11S,12S,14S,15R,16R,19S)-14-(acetyloxy)-5-hydroxy-16-[(1S)-1-[(2R,4R,5R)-4-hydroxy-4,5-dimethyl-6-oxooxan-2-yl]ethyl]-11,15-dimethyl-3,8-dioxahexacyclo[10.7.0.0^{2,4}.0^{5,11}.0^{7,9}.0^{15,19}]nonadecan-10-yl acetate

> <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       7.993   3.463   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.412   1.981   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.338   0.877   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.845   1.255   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.426   2.737   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.500   3.841   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.081   5.323   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.155   6.427   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.736   7.909   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.648   6.049   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.933   3.116   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.859   2.012   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.278   0.530   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.771   0.152   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.697  -0.952   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.366   2.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.947   3.872   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.021   4.976   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.514   4.598   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.602   6.458   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.676   7.561   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.258   9.043   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.169   7.183   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.591   3.932   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.124   2.487   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.086   1.534   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.448   5.212   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.984   5.110   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.665   3.728   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.201   3.627   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.058   4.907   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.377   6.288   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.234   7.568   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.841   6.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -7.594   4.805   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.154   2.088   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.451   2.726   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.767   6.593   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.376   5.302   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.007   4.219   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.264  -0.226   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       9.485   3.085   0.000  0.00  0.00           O+0
CONECT    1    2    6   42                                                  
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14   41                                             
CONECT    5    4    6   11   40                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   19                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    4   15                                                  
CONECT   15   14   13                                                       
CONECT   16   12   17   26                                                  
CONECT   17   16   18   24   39                                             
CONECT   18   17   19   20                                                  
CONECT   19   18   11                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   16                                                       
CONECT   27   24   28   38                                                  
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   36   37                                             
CONECT   31   30   32   35                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   28                                                       
CONECT   35   31                                                            
CONECT   36   30                                                            
CONECT   37   30                                                            
CONECT   38   27                                                            
CONECT   39   17                                                            
CONECT   40    5                                                            
CONECT   41    4                                                            
CONECT   42    2    1                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₆O₁₀

Average Mass

590.7100 Da

Monoisotopic Mass

590.30910 Da

IUPAC Name

(1S,2S,4S,5R,7S,9S,10R,11S,12S,14S,15R,16R,19S)-14-(acetyloxy)-5-hydroxy-16-[(1S)-1-[(2R,4R,5R)-4-hydroxy-4,5-dimethyl-6-oxooxan-2-yl]ethyl]-11,15-dimethyl-3,8-dioxahexacyclo[10.7.0.0^{2,4}.0^{5,11}.0^{7,9}.0^{15,19}]nonadecan-10-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1CC[C@H]2[C@@H]3[C@@H]4O[C@@H]4[C@@]4(O)C[C@@H]5O[C@@H]5[C@H](OC(C)=O)[C@]4(C)[C@H]3C[C@H](OC(C)=O)[C@]12C)[C@H]1C[C@@](C)(O)[C@@H](C)C(=O)O1

InChI Identifier

InChI=1S/C32H46O10/c1-13(20-11-29(5,36)14(2)28(35)41-20)17-8-9-18-23-19(10-22(30(17,18)6)38-15(3)33)31(7)26(39-16(4)34)24-21(40-24)12-32(31,37)27-25(23)42-27/h13-14,17-27,36-37H,8-12H2,1-7H3/t13-,14-,17+,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-,29+,30+,31-,32-/m0/s1

InChI Key

UBZJVFYBDALJKJ-VNYRJWHDSA-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
Tacca plantaginea	LOTUS Database	35616633
Tacca plantaginea (HANCE)	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
Steroid ester
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	1.98	ALOGPS
logP	1.46	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	141.12 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	145.17 m³·mol⁻¹	ChemAxon
Polarizability	62.82 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	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

C00031050

Chemspider ID

17238896

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16079921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Plantagiolide D (NP0071645)

MOL for NP0071645 ((+)-Plantagiolide D)

3D MOL for NP0071645 ((+)-Plantagiolide D)

3D SDF for NP0071645 ((+)-Plantagiolide D)

3D-SDF for NP0071645 ((+)-Plantagiolide D)

PDB for NP0071645 ((+)-Plantagiolide D)

3D PDB for NP0071645 ((+)-Plantagiolide D)

SMILES for NP0071645 ((+)-Plantagiolide D)

INCHI for NP0071645 ((+)-Plantagiolide D)

Structure for NP0071645 ((+)-Plantagiolide D)

3D Structure for NP0071645 ((+)-Plantagiolide D)