NP-MRD: Showing NP-Card for 2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate (NP0330496)

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Record Information

Version

2.0

Created at

2022-09-12 15:54:37 UTC

Updated at

2022-09-12 15:54:37 UTC

NP-MRD ID

NP0330496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate

Description

2,6,9,11,13,14-Hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]Pentadecan-12-yl benzoate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate is found in Ryania speciosa. 2,6,9,11,13,14-Hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]Pentadecan-12-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231515232D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004231515232D          

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    2.5685    0.6736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1925   -1.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226   -1.8582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4460   -0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3262   -0.0840    0.0000 C   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
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  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
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 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
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 19 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 25 34  1  0  0  0  0
 17 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  5 36  1  0  0  0  0
 22 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO)C1(O)C(OC(=O)C2=CC=CC=C2)C2(O)C3(C)CC4(O)OC5(C(O)C(C)CCC35O)C2(O)C14C

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O10/c1-14-10-11-22(31)20(3)13-23(32)21(4)24(33,15(2)12-28)19(36-18(30)16-8-6-5-7-9-16)25(20,34)27(21,35)26(22,37-23)17(14)29/h5-9,14-15,17,19,28-29,31-35H,10-13H2,1-4H3

> <INCHI_KEY>
XISJCAXTBNIGRL-UHFFFAOYSA-N

> <FORMULA>
C27H36O10

> <MOLECULAR_WEIGHT>
520.575

> <EXACT_MASS>
520.230847359

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.50849850889145

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-0.29315501833333396

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.906253768661625

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.238697679980492

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6310067761333444

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
126.25649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -2.305  -2.684   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.892  -3.295   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.714  -4.825   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.950  -5.743   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.344  -2.377   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.609  -3.256   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.107  -0.989   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.388  -0.133   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.769  -0.814   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.870  -2.351   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.050   0.041   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.431  -0.640   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.711   0.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.611   1.752   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.230   2.433   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.949   1.578   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.833  -0.837   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.783   0.290   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.220   0.571   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.274   1.694   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.369   1.740   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.477   0.682   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.044   0.437   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.068  -0.292   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.814  -1.660   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.016  -2.754   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.563  -4.226   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.583  -2.531   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.548  -3.731   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.125  -1.081   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.103   0.088   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.527  -0.259   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.795   1.257   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.226  -1.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.282  -3.469   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.833  -0.699   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.609  -0.157   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7   36                                             
CONECT    6    5                                                            
CONECT    7    5    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    7   18   19   34                                             
CONECT   18   17                                                            
CONECT   19   17   20   21   32                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24   36                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   32   34                                             
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   19   25   33                                             
CONECT   33   32                                                            
CONECT   34   25   17   35   36                                             
CONECT   35   34                                                            
CONECT   36   34    5   22   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Value	Source
2,6,9,11,13,14-Hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0,.0,.0,]pentadecan-12-yl benzoic acid	Generator
2,6,9,11,13,14-Hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoic acid	Generator

Chemical Formula

C₂₇H₃₆O₁₀

Average Mass

520.5750 Da

Monoisotopic Mass

520.23085 Da

IUPAC Name

2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate

Traditional Name

2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(CO)C1(O)C(OC(=O)C2=CC=CC=C2)C2(O)C3(C)CC4(O)OC5(C(O)C(C)CCC35O)C2(O)C14C

InChI Identifier

InChI=1S/C27H36O10/c1-14-10-11-22(31)20(3)13-23(32)21(4)24(33,15(2)12-28)19(36-18(30)16-8-6-5-7-9-16)25(20,34)27(21,35)26(22,37-23)17(14)29/h5-9,14-15,17,19,28-29,31-35H,10-13H2,1-4H3

InChI Key

XISJCAXTBNIGRL-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
Ryania speciosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Ryanodane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Oxepane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Hemiacetal
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Polyol
Organic oxygen compound
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.11	ALOGPS
logP	-0.29	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.24	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.26 m³·mol⁻¹	ChemAxon
Polarizability	52.51 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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 2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate (NP0330496)

MOL for NP0330496 (2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate)

3D MOL for NP0330496 (2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate)

3D SDF for NP0330496 (2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate)

3D-SDF for NP0330496 (2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate)

PDB for NP0330496 (2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate)

3D PDB for NP0330496 (2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate)

SMILES for NP0330496 (2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate)

INCHI for NP0330496 (2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate)

Structure for NP0330496 (2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate)

3D Structure for NP0330496 (2,6,9,11,13,14-hexahydroxy-11-(1-hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.0¹,⁶.0⁷,¹³.0¹⁰,¹⁴]pentadecan-12-yl benzoate)