NP-MRD: Showing NP-Card for methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate (NP0317545)

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Record Information

Version

2.0

Created at

2022-09-11 17:29:53 UTC

Updated at

2022-09-11 17:29:54 UTC

NP-MRD ID

NP0317545

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate

Description

Methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate is found in Salvia divinorum. Methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241506242D          

 37 40  0  0  0  0            999 V2000
    2.9055    4.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1540    3.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5665    2.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7225    1.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 35 37  1  0  0  0  0
 12 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241506242D          

 37 40  0  0  0  0            999 V2000
    2.9055    4.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 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
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 14 30  1  0  0  0  0
 19 30  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 16 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 12 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317545

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1OC(OC)C(O)(C1O)C1CC2(C)C(CCC3(C)C(CC(OC(C)=O)C(=O)C23)C(=O)OC)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O12/c1-11(26)35-14-9-13(19(29)32-4)23(2)8-7-12-20(30)36-15(10-24(12,3)17(23)16(14)27)25(31)18(28)21(33-5)37-22(25)34-6/h12-15,17-18,21-22,28,31H,7-10H2,1-6H3

> <INCHI_KEY>
QEBAQEQKIKWXTO-UHFFFAOYSA-N

> <FORMULA>
C25H36O12

> <MOLECULAR_WEIGHT>
528.551

> <EXACT_MASS>
528.220676599

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.504238748081676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.5266987203333311

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.88442616609617

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.070391014279478

> <JCHEM_PKA_STRONGEST_BASIC>
-3.903582849290069

> <JCHEM_POLAR_SURFACE_AREA>
164.11999999999998

> <JCHEM_REFRACTIVITY>
121.32069999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1H-naphtho[2,1-c]pyran-7-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.424   8.132   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.103   6.626   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.248   5.595   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.754   5.915   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.524   4.582   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.056   4.421   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.682   3.014   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.740   2.532   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.087   4.064   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.753   3.294   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.206   6.105   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.746  -1.897   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.564  -3.231   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.206  -4.565   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.494  -1.897   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       7.494   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10   12                                             
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   37                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   30                                             
CONECT   15   14                                                            
CONECT   16   14   17   35                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   30                                             
CONECT   20   19                                                            
CONECT   21   19   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   14   19                                                  
CONECT   31   21   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   16   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   12                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₆O₁₂

Average Mass

528.5510 Da

Monoisotopic Mass

528.22068 Da

IUPAC Name

methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate

Traditional Name

methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1H-naphtho[2,1-c]pyran-7-carboxylate

CAS Registry Number

Not Available

SMILES

COC1OC(OC)C(O)(C1O)C1CC2(C)C(CCC3(C)C(CC(OC(C)=O)C(=O)C23)C(=O)OC)C(=O)O1

InChI Identifier

InChI=1S/C25H36O12/c1-11(26)35-14-9-13(19(29)32-4)23(2)8-7-12-20(30)36-15(10-24(12,3)17(23)16(14)27)25(31)18(28)21(33-5)37-22(25)34-6/h12-15,17-18,21-22,28,31H,7-10H2,1-6H3

InChI Key

QEBAQEQKIKWXTO-UHFFFAOYSA-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
Salvia divinorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Naphthopyran
Glycosyl compound
O-glycosyl compound
Naphthalene
Pentose monosaccharide
Tricarboxylic acid or derivatives
Alpha-acyloxy ketone
Delta valerolactone
Delta_valerolactone
Monosaccharide
Oxane
Pyran
Tertiary alcohol
Tetrahydrofuran
Methyl ester
Secondary alcohol
Lactone
Ketone
1,2-diol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
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	0.66	ALOGPS
logP	0.53	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.07	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	164.12 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.32 m³·mol⁻¹	ChemAxon
Polarizability	53.5 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate (NP0317545)

MOL for NP0317545 (methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate)

3D MOL for NP0317545 (methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate)

3D SDF for NP0317545 (methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate)

3D-SDF for NP0317545 (methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate)

PDB for NP0317545 (methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate)

3D PDB for NP0317545 (methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate)

SMILES for NP0317545 (methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate)

INCHI for NP0317545 (methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate)

Structure for NP0317545 (methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate)

3D Structure for NP0317545 (methyl 9-(acetyloxy)-2-(3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl)-6a,10b-dimethyl-4,10-dioxo-octahydro-1h-naphtho[2,1-c]pyran-7-carboxylate)