NP-MRD: Showing NP-Card for 3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate (NP0314502)

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Record Information

Version

2.0

Created at

2022-09-11 12:37:55 UTC

Updated at

2022-09-11 12:37:56 UTC

NP-MRD ID

NP0314502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate

Description

3-(Acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]Heptadecan-2-yl propanoate belongs to the class of organic compounds known as grayanoids. These are diterpenoids containing a skeleton based on or derived from the ent-kaurane moiety. Grayanoids usually possess either one of the grayanane, the 2,4-seco-grayanane, the 9,10-seco-grayanane, the 1,5-seco-grayanane, the kalmane, or the leucothane skeleton. Some derivatives also include the 1,5-seco-kalmane skeleton. 3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate is found in Pieris japonica. 3-(Acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]Heptadecan-2-yl propanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171518472D          

 35 39  0  0  0  0            999 V2000
    0.0214    2.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8289    2.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792    2.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1221    1.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867    2.3987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370    1.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284    2.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6410    2.8654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9896    3.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255    3.0605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022    4.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2152    1.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004171518472D          

 35 39  0  0  0  0            999 V2000
    0.0214    2.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 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
 29 31  1  0  0  0  0
  6 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OC1C(OC(C)=O)C2(O)C(C3OC3C2(C)C)C(C)(O)C2(O)CCC3C(O)C12CC3(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O10/c1-7-13(27)34-18-19(33-11(2)26)25(32)15(14-17(35-14)20(25,3)4)22(6,30)24(31)9-8-12-16(28)23(18,24)10-21(12,5)29/h12,14-19,28-32H,7-10H2,1-6H3

> <INCHI_KEY>
MPCOOJRHDJYPMN-UHFFFAOYSA-N

> <FORMULA>
C25H38O10

> <MOLECULAR_WEIGHT>
498.569

> <EXACT_MASS>
498.246497424

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.50465582340111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
-1.128185757333332

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.256144011713012

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.664070198837159

> <JCHEM_PKA_STRONGEST_BASIC>
-2.94094344878717

> <JCHEM_POLAR_SURFACE_AREA>
166.28

> <JCHEM_REFRACTIVITY>
117.87769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       0.040   4.993   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.547   5.309   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.575   4.162   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.095   2.698   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.082   4.478   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.109   3.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.586   3.823   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.797   5.349   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.581   6.294   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.154   5.713   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.791   7.819   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.868   2.954   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.011   4.487   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.016   1.421   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.520   1.088   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.060   1.075   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.301   2.415   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.281   3.568   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.309   4.715   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.833   5.042   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.916   0.343   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.212  -0.490   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.393  -1.106   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.380   0.531   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.720  -0.971   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.789  -0.971   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.199  -1.114   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.278   0.230   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.415   1.011   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.351  -0.211   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.443   1.888   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.003   2.740   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.708   1.760   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.633   2.863   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.209   1.405   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                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   17                                                       
CONECT   17   16   15   18                                                  
CONECT   18   17   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   14   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25   26   31                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    6   24   32                                             
CONECT   32   31   33                                                       
CONECT   33   32   28   34   35                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
3-(Acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0,.0,.0,]heptadecan-2-yl propanoic acid	Generator
3-(Acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoic acid	Generator

Chemical Formula

C₂₅H₃₈O₁₀

Average Mass

498.5690 Da

Monoisotopic Mass

498.24650 Da

IUPAC Name

3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate

Traditional Name

3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)OC1C(OC(C)=O)C2(O)C(C3OC3C2(C)C)C(C)(O)C2(O)CCC3C(O)C12CC3(C)O

InChI Identifier

InChI=1S/C25H38O10/c1-7-13(27)34-18-19(33-11(2)26)25(32)15(14-17(35-14)20(25,3)4)22(6,30)24(31)9-8-12-16(28)23(18,24)10-21(12,5)29/h12,14-19,28-32H,7-10H2,1-6H3

InChI Key

MPCOOJRHDJYPMN-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
Pieris japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as grayanoids. These are diterpenoids containing a skeleton based on or derived from the ent-kaurane moiety. Grayanoids usually possess either one of the grayanane, the 2,4-seco-grayanane, the 9,10-seco-grayanane, the 1,5-seco-grayanane, the kalmane, or the leucothane skeleton. Some derivatives also include the 1,5-seco-kalmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Grayanoids

Alternative Parents

Substituents

Grayanoid
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Polyol
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
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	0.51	ALOGPS
logP	-1.1	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.66	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	166.28 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.88 m³·mol⁻¹	ChemAxon
Polarizability	50.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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 3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate (NP0314502)

MOL for NP0314502 (3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate)

3D MOL for NP0314502 (3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate)

3D SDF for NP0314502 (3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate)

3D-SDF for NP0314502 (3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate)

PDB for NP0314502 (3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate)

3D PDB for NP0314502 (3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate)

SMILES for NP0314502 (3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate)

INCHI for NP0314502 (3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate)

Structure for NP0314502 (3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate)

3D Structure for NP0314502 (3-(acetyloxy)-4,10,11,15,17-pentahydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-2-yl propanoate)