NP-MRD: Showing NP-Card for 15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid (NP0319277)

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Record Information

Version

2.0

Created at

2022-09-11 20:13:40 UTC

Updated at

2022-09-11 20:13:40 UTC

NP-MRD ID

NP0319277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Description

15-Hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylic acid belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 15-Hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171512502D          

 34 38  0  0  0  0            999 V2000
    1.8257    0.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4672    2.6670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0399    0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4817   -0.5503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  7  8  1  0  0  0  0
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  2 15  1  0  0  0  0
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 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
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  6 20  1  0  0  0  0
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 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004171512502D          

 34 38  0  0  0  0            999 V2000
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 24 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
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(CC(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O9/c1-11-12-3-4-17-24(2)9-13(33-23-20(29)19(28)18(27)16(10-26)34-23)7-14(22(31)32)15(24)5-6-25(17,8-12)21(11)30/h12-21,23,26-30H,1,3-10H2,2H3,(H,31,32)

> <INCHI_KEY>
ZUDBDCBPZHGAEL-UHFFFAOYSA-N

> <FORMULA>
C25H38O9

> <MOLECULAR_WEIGHT>
482.57

> <EXACT_MASS>
482.251582804

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.215871941330626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
0.01935868266666743

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.210576033441285

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2294300398502305

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7378428184299682

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
118.3069

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <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       3.408   1.452   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.857  -0.022   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.899   1.113   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.402   0.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.863  -0.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.821  -1.826   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.318  -1.491   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.285  -2.656   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.774  -2.341   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.208  -0.872   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.322   0.124   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.752   0.996   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.296   2.224   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.874   1.924   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.328   0.347   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.466  -0.449   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.984  -0.707   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.306  -1.583   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.562  -3.102   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.282  -3.295   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.240  -4.429   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.785  -3.631   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.443   1.911   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.946   1.576   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.988   2.710   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.491   2.375   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.533   3.509   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.072   4.978   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.953   0.906   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.456   0.571   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.911  -0.228   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.372  -1.698   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.408   0.107   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.366  -1.027   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   15                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15   18                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    2   10                                                  
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10   19                                                  
CONECT   19   18                                                            
CONECT   20    6   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    4   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   24   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
15-Hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0,.0,]hexadecane-5-carboxylate	Generator
15-Hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate	Generator

Chemical Formula

C₂₅H₃₈O₉

Average Mass

482.5700 Da

Monoisotopic Mass

482.25158 Da

IUPAC Name

15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Traditional Name

15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12CC(CC(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C25H38O9/c1-11-12-3-4-17-24(2)9-13(33-23-20(29)19(28)18(27)16(10-26)34-23)7-14(22(31)32)15(24)5-6-25(17,8-12)21(11)30/h12-21,23,26-30H,1,3-10H2,2H3,(H,31,32)

InChI Key

ZUDBDCBPZHGAEL-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

Not Available

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
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acyl
Monosaccharide
Oxane
Cyclic alcohol
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid
Carboxylic acid derivative
Primary alcohol
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	-0.19	ALOGPS
logP	0.019	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	-0.74	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.31 m³·mol⁻¹	ChemAxon
Polarizability	51.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

14037431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid (NP0319277)

MOL for NP0319277 (15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D MOL for NP0319277 (15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D SDF for NP0319277 (15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D-SDF for NP0319277 (15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

PDB for NP0319277 (15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D PDB for NP0319277 (15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

SMILES for NP0319277 (15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

INCHI for NP0319277 (15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

Structure for NP0319277 (15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D Structure for NP0319277 (15-hydroxy-9-methyl-14-methylidene-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)