NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate (NP0319797)

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Record Information

Version

2.0

Created at

2022-09-11 21:01:24 UTC

Updated at

2022-09-11 21:01:25 UTC

NP-MRD ID

NP0319797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate

Description

AC1LAU7Z belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate is found in Adenostemma lavenia. AC1LAU7Z is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201501532D          

 36 41  0  0  0  0            999 V2000
    4.1830    1.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004201501532D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  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
  6  8  1  0  0  0  0
  2  8  1  0  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
 13 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
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 22  1  0  0  0  0
  2 22  1  0  0  0  0
 11 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  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 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCCC(C)(C1CCC13CC4CC(OC4(CO)C1O)C23)C(=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H40O10/c1-23-5-3-6-24(2,22(33)35-20-18(31)17(30)16(29)14(10-27)34-20)15(23)4-7-25-9-12-8-13(19(23)25)36-26(12,11-28)21(25)32/h12-21,27-32H,3-11H2,1-2H3

> <INCHI_KEY>
WHWKRKUTKZNNOI-UHFFFAOYSA-N

> <FORMULA>
C26H40O10

> <MOLECULAR_WEIGHT>
512.596

> <EXACT_MASS>
512.262147488

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.69783794626365

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate

> <ALOGPS_LOGP>
-0.69

> <JCHEM_LOGP>
-0.5407660813333335

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.025201179571013

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.172546871024377

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981093680169468

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
122.533

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       7.808   2.452   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.436   1.046   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.327   2.301   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.861   2.157   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.502   0.757   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.611  -0.499   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.002  -1.159   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.077  -0.354   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.128  -1.615   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.573  -1.401   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.769  -0.025   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.691   1.109   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.841   2.616   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.038   3.725   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.328   2.774   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.899   2.182   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.518   1.144   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.986   0.989   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.354  -0.416   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.177  -0.338   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.467  -1.704   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.853   1.227   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.202  -1.983   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.712  -2.372   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      11.284  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.876  -4.564   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.958  -5.660   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.549  -7.145   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.631  -8.241   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.121  -7.853   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.059  -7.534   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.651  -9.019   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.977  -6.438   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.487  -6.827   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.386  -4.953   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.304  -3.857   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   23                                             
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20   22                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   13   18   20                                             
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   11   21                                                  
CONECT   21   20                                                            
CONECT   22   15    2   11                                                  
CONECT   23    6   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   26   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₀O₁₀

Average Mass

512.5960 Da

Monoisotopic Mass

512.26215 Da

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate

Traditional Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate

CAS Registry Number

Not Available

SMILES

CC12CCCC(C)(C1CCC13CC4CC(OC4(CO)C1O)C23)C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H40O10/c1-23-5-3-6-24(2,22(33)35-20-18(31)17(30)16(29)14(10-27)34-20)15(23)4-7-25-9-12-8-13(19(23)25)36-26(12,11-28)21(25)32/h12-21,27-32H,3-11H2,1-2H3

InChI Key

WHWKRKUTKZNNOI-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
Adenostemma lavenia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Kaurane diterpenoid
Naphthopyran
Hexose monosaccharide
Naphthalene
Oxepane
Monosaccharide
Pyran
Oxane
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Acetal
Carboxylic acid derivative
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	-0.69	ALOGPS
logP	-0.54	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.53 m³·mol⁻¹	ChemAxon
Polarizability	53.7 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

495063

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate (NP0319797)

MOL for NP0319797 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

3D MOL for NP0319797 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

3D SDF for NP0319797 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

3D-SDF for NP0319797 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

PDB for NP0319797 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

3D PDB for NP0319797 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

SMILES for NP0319797 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

INCHI for NP0319797 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

Structure for NP0319797 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)

3D Structure for NP0319797 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 16-hydroxy-13-(hydroxymethyl)-5,9-dimethyl-12-oxapentacyclo[11.2.1.1¹¹,¹⁴.0¹,¹⁰.0⁴,⁹]heptadecane-5-carboxylate)