NP-MRD: Showing NP-Card for (1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate (NP0201869)

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Record Information

Version

2.0

Created at

2022-09-04 20:59:15 UTC

Updated at

2022-09-04 20:59:15 UTC

NP-MRD ID

NP0201869

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

153415-39-5 Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate is found in Scutellaria alpina. Based on a literature review very few articles have been published on 153415-39-5.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042222592D          

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M  END

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M  END


  Mrv1652309042222592D          

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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  1  0  0  0
 28 31  1  0  0  0  0
  8 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0201869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@H]1C[C@](C)(O)[C@](C)([C@@H](O)CC2=CC(=O)OC2)[C@H]2CCC[C@]3(CO3)[C@]12COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O9/c1-6-16(2)23(31)36-21-12-24(4,32)25(5,20(29)10-18-11-22(30)33-13-18)19-8-7-9-26(14-35-26)27(19,21)15-34-17(3)28/h6,11,19-21,29,32H,7-10,12-15H2,1-5H3/b16-6+/t19-,20+,21+,24+,25+,26+,27+/m1/s1

> <INCHI_KEY>
NBURIQQSSONYID-ZGJQKLIZSA-N

> <FORMULA>
C27H38O9

> <MOLECULAR_WEIGHT>
506.592

> <EXACT_MASS>
506.251582804

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.42569290463897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
1.9234260606666647

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.18706225496334

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.116827593368332

> <JCHEM_PKA_STRONGEST_BASIC>
-3.000715331474246

> <JCHEM_POLAR_SURFACE_AREA>
131.89000000000001

> <JCHEM_REFRACTIVITY>
129.41339999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.702  -7.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.207  -6.786   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.674  -5.319   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.637  -4.180   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.179  -4.990   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.216  -6.129   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.646  -3.523   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.609  -2.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.105  -2.713   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.068  -1.575   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.704  -0.859   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.127  -2.793   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.536  -0.107   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.009   0.098   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.473   1.431   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.775   2.255   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.109   2.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.047   3.685   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.235   4.539   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.182   6.022   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.773   7.230   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.720   6.085   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.255   4.640   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.040   0.221   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.508   1.689   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.012   2.017   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.049   0.879   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.582  -0.589   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.049  -1.056   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.910  -2.093   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.077  -0.917   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.247  -2.448   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.657  -3.066   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.827  -4.597   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.835  -6.137   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.237  -5.215   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   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   15   24                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   18                                                       
CONECT   24   13   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28   30                                                       
CONECT   30   29   28                                                       
CONECT   31   28    8   24   32                                             
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₉

Average Mass

506.5920 Da

Monoisotopic Mass

506.25158 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@H]1C[C@](C)(O)[C@](C)([C@@H](O)CC2=CC(=O)OC2)[C@H]2CCC[C@]3(CO3)[C@]12COC(C)=O

InChI Identifier

InChI=1S/C27H38O9/c1-6-16(2)23(31)36-21-12-24(4,32)25(5,20(29)10-18-11-22(30)33-13-18)19-8-7-9-26(14-35-26)27(19,21)15-34-17(3)28/h6,11,19-21,29,32H,7-10,12-15H2,1-5H3/b16-6+/t19-,20+,21+,24+,25+,26+,27+/m1/s1

InChI Key

NBURIQQSSONYID-ZGJQKLIZSA-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
Scutellaria alpina	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
2-furanone
Fatty acyl
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Dialkyl ether
Oxacycle
Oxirane
Ether
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
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	1.92	ChemAxon
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	131.89 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	129.41 m³·mol⁻¹	ChemAxon
Polarizability	53.43 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

8159265

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9983675

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate (NP0201869)

MOL for NP0201869 ((1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0201869 ((1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0201869 ((1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0201869 ((1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate)

PDB for NP0201869 ((1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0201869 ((1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0201869 ((1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0201869 ((1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate)

Structure for NP0201869 ((1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0201869 ((1r,4ar,5s,6s,8s,8ar)-8a-[(acetyloxy)methyl]-6-hydroxy-5-[(1s)-1-hydroxy-2-(5-oxo-2h-furan-3-yl)ethyl]-5,6-dimethyl-hexahydrospiro[naphthalene-1,2'-oxiran]-8-yl (2e)-2-methylbut-2-enoate)