NP-MRD: Showing NP-Card for (4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate (NP0161578)

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Record Information

Version

2.0

Created at

2022-09-02 19:47:24 UTC

Updated at

2022-09-02 19:47:24 UTC

NP-MRD ID

NP0161578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate

Description

121449-66-9 Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate is found in Ajuga nipponensis. Based on a literature review very few articles have been published on 121449-66-9.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022221472D          

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M  END

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M  END


  Mrv1652309022221472D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  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  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  2  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
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 36 25  1  1  0  0  0
  8 36  1  0  0  0  0
 14 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0161578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)O[C@@H]1CCC2(CO2)[C@]2(COC(C)=O)[C@@H](O)C[C@@H](C)[C@](C)(C[C@H](O)C3=CC(=O)OC3)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O9/c1-6-15(2)24(32)36-20-7-8-26(13-35-26)27(14-34-17(4)28)21(30)9-16(3)25(5,23(20)27)11-19(29)18-10-22(31)33-12-18/h10,15-16,19-21,23,29-30H,6-9,11-14H2,1-5H3/t15-,16+,19-,20+,21-,23+,25-,26?,27+/m0/s1

> <INCHI_KEY>
CLJVKWUXMLHMNP-UUSPLHFDSA-N

> <FORMULA>
C27H40O9

> <MOLECULAR_WEIGHT>
508.608

> <EXACT_MASS>
508.267232868

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.518542574468576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.8409877306666655

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.40309638584025

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.766976827092232

> <JCHEM_PKA_STRONGEST_BASIC>
-3.010349473667487

> <JCHEM_POLAR_SURFACE_AREA>
131.89

> <JCHEM_REFRACTIVITY>
128.5685

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.03e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.812   9.761   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.225   8.622   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.243   7.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.747   6.826   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.794   6.016   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.299   6.345   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.327   4.549   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.364   3.410   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.868   3.739   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.905   2.601   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.438   1.133   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.905   0.666   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.766  -0.371   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.933   0.805   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.103  -0.726   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.513  -1.344   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.683  -2.875   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.442  -3.787   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.093  -3.494   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.465  -0.663   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.502  -1.801   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.039  -0.991   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.076   0.147   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.581  -0.181   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.608   1.614   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.671   3.153   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.135   1.820   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.720   3.245   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.778   4.464   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.246   3.450   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.309   2.337   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.697   3.004   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -8.053   2.273   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -6.491   4.530   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.976   4.806   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.896   1.943   0.000  0.00  0.00           C+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   36                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11   13                                                       
CONECT   13   12   11                                                       
CONECT   14   11   15   20   36                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   36                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   30                                                       
CONECT   36   25    8   14                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₉

Average Mass

508.6080 Da

Monoisotopic Mass

508.26723 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)O[C@@H]1CCC2(CO2)[C@]2(COC(C)=O)[C@@H](O)C[C@@H](C)[C@](C)(C[C@H](O)C3=CC(=O)OC3)[C@@H]12

InChI Identifier

InChI=1S/C27H40O9/c1-6-15(2)24(32)36-20-7-8-26(13-35-26)27(14-34-17(4)28)21(30)9-16(3)25(5,23(20)27)11-19(29)18-10-22(31)33-12-18/h10,15-16,19-21,23,29-30H,6-9,11-14H2,1-5H3/t15-,16+,19-,20+,21-,23+,25-,26?,27+/m0/s1

InChI Key

CLJVKWUXMLHMNP-UUSPLHFDSA-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 nipponensis	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
Fatty acid ester
Fatty acyl
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.82	ALOGPS
logP	1.84	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	5.77	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	131.89 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	128.57 m³·mol⁻¹	ChemAxon
Polarizability	53.52 Å³	ChemAxon
Number of Rings	4	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

156694

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

180055

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate (NP0161578)

MOL for NP0161578 ((4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate)

3D MOL for NP0161578 ((4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate)

3D SDF for NP0161578 ((4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate)

3D-SDF for NP0161578 ((4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate)

PDB for NP0161578 ((4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate)

3D PDB for NP0161578 ((4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate)

SMILES for NP0161578 ((4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate)

INCHI for NP0161578 ((4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate)

Structure for NP0161578 ((4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate)

3D Structure for NP0161578 ((4r,4ar,5s,6r,8s,8ar)-8a-[(acetyloxy)methyl]-8-hydroxy-5-[(2s)-2-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-4-yl (2s)-2-methylbutanoate)