NP-MRD: Showing NP-Card for 14-hydro-15-hydroxyajugapitin (NP0327028)

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Record Information

Version

2.0

Created at

2022-09-12 09:12:12 UTC

Updated at

2022-09-12 09:12:13 UTC

NP-MRD ID

NP0327028

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-hydro-15-hydroxyajugapitin

Description

14-Hydro-15-hydroxyajugapitin belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 14-Hydro-15-hydroxyajugapitin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 14-hydro-15-hydroxyajugapitin is found in Ajuga bracteosa and Ajuga chamaepitys. 14-hydro-15-hydroxyajugapitin was first documented in 2005 (PMID: 15688959). Based on a literature review very few articles have been published on 14-hydro-15-hydroxyajugapitin (PMID: 21539300).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122211122D          

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M  END

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M  END


  Mrv1652309122211122D          

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    5.2946   -0.3504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1006   -0.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -0.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9331   -0.7843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3776   -1.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6281   -2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4341   -2.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0726   -2.7903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.0017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5917   -0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8362   -1.1495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453   -1.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407   -2.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9898   -2.3008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766    0.1778    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7005   -0.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0906   -0.0727    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 22 21  1  1  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  6  0  0  0
 13 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 32 38  1  0  0  0  0
  8 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0327028

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)O[C@H]1[C@H](O)C[C@@H]2[C@@](C)([C@@H]3C[C@H]4CC(O)O[C@H]4O3)[C@H](C)C[C@H](OC(C)=O)[C@@]2(COC(C)=O)[C@@]11CO1

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O11/c1-7-14(2)25(34)40-24-19(32)11-20-27(6,21-9-18-10-23(33)39-26(18)38-21)15(3)8-22(37-17(5)31)28(20,12-35-16(4)30)29(24)13-36-29/h14-15,18-24,26,32-33H,7-13H2,1-6H3/t14?,15-,18+,19-,20-,21+,22+,23?,24+,26-,27+,28+,29-/m1/s1

> <INCHI_KEY>
SAENNVULKVVZSO-ZDEAQARGSA-N

> <FORMULA>
C29H44O11

> <MOLECULAR_WEIGHT>
568.66

> <EXACT_MASS>
568.288362237

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
59.76444962363297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(2S,3aS,6aR)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylbutanoate

> <JCHEM_LOGP>
1.6466170816666654

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.075915223442998

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.382630083236648

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2069665131853027

> <JCHEM_POLAR_SURFACE_AREA>
150.35000000000002

> <JCHEM_REFRACTIVITY>
137.0615

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(2S,3aS,6aR)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.685   0.508   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.181   0.179   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.856   1.318   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.389   2.785   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.361   0.989   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.828  -0.478   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.398   2.128   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.902   1.799   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.939   2.938   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.471   4.405   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.444   2.609   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.911   1.142   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.416   0.813   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.478   2.352   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.942   1.019   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.672   2.375   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.188   2.099   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.575   2.766   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.639   1.652   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.165   1.858   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.908   0.296   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.393   0.572   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.005  -0.095   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.883  -0.654   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.388  -0.983   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.846  -1.793   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.342  -1.464   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.305  -2.603   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.773  -4.070   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.277  -4.399   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.736  -5.209   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.874   0.003   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.705  -1.527   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.294  -2.146   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.125  -3.676   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.116  -5.216   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.714  -4.295   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.370   0.332   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.041  -1.173   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.902  -0.136   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   38                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12   14   15   24                                             
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22   15                                                       
CONECT   24   13   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   12   33   38                                             
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   32    8   39   40                                             
CONECT   39   38   40                                                       
CONECT   40   39   38                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
14-Hydro-2,15-dihydroxy-3beta-isobutyryloxyclerodin	ChEBI
14-Hydro-2,15-dihydroxy-3b-isobutyryloxyclerodin	Generator
14-Hydro-2,15-dihydroxy-3β-isobutyryloxyclerodin	Generator

Chemical Formula

C₂₉H₄₄O₁₁

Average Mass

568.6600 Da

Monoisotopic Mass

568.28836 Da

IUPAC Name

(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(2S,3aS,6aR)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylbutanoate

Traditional Name

(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(2S,3aS,6aR)-5-hydroxy-hexahydrofuro[2,3-b]furan-2-yl]-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)O[C@H]1[C@H](O)C[C@@H]2[C@@](C)([C@@H]3C[C@H]4CC(O)O[C@H]4O3)[C@H](C)C[C@H](OC(C)=O)[C@@]2(COC(C)=O)[C@@]11CO1

InChI Identifier

InChI=1S/C29H44O11/c1-7-14(2)25(34)40-24-19(32)11-20-27(6,21-9-18-10-23(33)39-26(18)38-21)15(3)8-22(37-17(5)31)28(20,12-35-16(4)30)29(24)13-36-29/h14-15,18-24,26,32-33H,7-13H2,1-6H3/t14?,15-,18+,19-,20-,21+,22+,23?,24+,26-,27+,28+,29-/m1/s1

InChI Key

SAENNVULKVVZSO-ZDEAQARGSA-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
Ajuga bracteosa	LOTUS Database	35616633
Ajuga chamaepitys	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Furofuran
Fatty acid ester
Fatty acyl
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Ether
Oxirane
Dialkyl ether
Acetal
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:67471 )
acetate ester (CHEBI:67471 )
diterpenoid (CHEBI:67471 )
oxaspiro compound (CHEBI:67471 )
furofuran (CHEBI:67471 )

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	1.65	ChemAxon
pKa (Strongest Acidic)	12.38	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	150.35 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	137.06 m³·mol⁻¹	ChemAxon
Polarizability	59.76 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	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

34999277

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70697927

PDB ID

Not Available

ChEBI ID

67471

Good Scents ID

Not Available

References

General References

Castro A, Coll J, Arfan M: neo-Clerodane diterpenoids from Ajuga bracteosa. J Nat Prod. 2011 May 27;74(5):1036-41. doi: 10.1021/np100929u. Epub 2011 May 3. [PubMed:21539300 ]
Coll J, Tandron Y: Isolation and identification of neo-clerodane diterpenes from Ajuga remota by high-performance liquid chromatography. Phytochem Anal. 2005 Jan-Feb;16(1):61-7. doi: 10.1002/pca.812. [PubMed:15688959 ]
LOTUS database [Link]

Showing NP-Card for 14-hydro-15-hydroxyajugapitin (NP0327028)

MOL for NP0327028 (14-hydro-15-hydroxyajugapitin)

3D MOL for NP0327028 (14-hydro-15-hydroxyajugapitin)

3D SDF for NP0327028 (14-hydro-15-hydroxyajugapitin)

3D-SDF for NP0327028 (14-hydro-15-hydroxyajugapitin)

PDB for NP0327028 (14-hydro-15-hydroxyajugapitin)

3D PDB for NP0327028 (14-hydro-15-hydroxyajugapitin)

SMILES for NP0327028 (14-hydro-15-hydroxyajugapitin)

INCHI for NP0327028 (14-hydro-15-hydroxyajugapitin)

Structure for NP0327028 (14-hydro-15-hydroxyajugapitin)

3D Structure for NP0327028 (14-hydro-15-hydroxyajugapitin)