NP-MRD: Showing NP-Card for 6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione (NP0296843)

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Record Information

Version

2.0

Created at

2022-09-10 06:41:14 UTC

Updated at

2022-09-10 06:41:14 UTC

NP-MRD ID

NP0296843

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

Description

6,7,14-Trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]Hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione belongs to the class of organic compounds known as c20-gibberellin 6-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position. 6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione is found in Aphananthe aspera, Camptotheca acuminata, Cleidion brevipetiolatum, Dipentodon sinicus, Euphorbia sessiliflora and Phyllagathis rotundifolia. 6,7,14-Trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]Hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181503392D          

 36 40  0  0  0  0            999 V2000
    5.9664   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0164   -1.5395    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


  Mrv1533004181503392D          

 36 40  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0296843

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3C(OC(=O)C4=C3C(OC2=O)=C(OC)C(OC2OC(CO)C(O)C(O)C2O)=C4)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O13/c1-30-9-4-7-12-13-8(22(29)35-19(12)17(9)31-2)5-10(18(32-3)20(13)36-21(7)28)33-23-16(27)15(26)14(25)11(6-24)34-23/h4-5,11,14-16,23-27H,6H2,1-3H3

> <INCHI_KEY>
RKFCDGOVCBYSEW-UHFFFAOYSA-N

> <FORMULA>
C23H22O13

> <MOLECULAR_WEIGHT>
506.416

> <EXACT_MASS>
506.106040768

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
48.09872381868874

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-3,10-dione

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
-0.8144635073333337

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19604286934388

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200012612886663

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549535993

> <JCHEM_POLAR_SURFACE_AREA>
179.67

> <JCHEM_REFRACTIVITY>
116.19889999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-3,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      11.137  -0.206   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.367  -1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -4.207   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.517  -5.541   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.207  -4.207   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.127  -4.207   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.413  -4.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.183  -0.206   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.723  -0.206   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.493   1.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.033   1.127   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.803  -0.206   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.723   2.461   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.493   3.795   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.183   2.461   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.413   3.795   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.413   1.127   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.127   1.127   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.207   1.127   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.437   2.461   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.747   1.127   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.827   1.127   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.367   1.127   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   36                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
CONECT   26   13   27                                                       
CONECT   27   26   28   36                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31    3   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   31    5   36                                                  
CONECT   36   35    9   27                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₁₃

Average Mass

506.4160 Da

Monoisotopic Mass

506.10604 Da

IUPAC Name

6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-3,10-dione

Traditional Name

6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-3,10-dione

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3C(OC(=O)C4=C3C(OC2=O)=C(OC)C(OC2OC(CO)C(O)C(O)C2O)=C4)=C1OC

InChI Identifier

InChI=1S/C23H22O13/c1-30-9-4-7-12-13-8(22(29)35-19(12)17(9)31-2)5-10(18(32-3)20(13)36-21(7)28)33-23-16(27)15(26)14(25)11(6-24)34-23/h4-5,11,14-16,23-27H,6H2,1-3H3

InChI Key

RKFCDGOVCBYSEW-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
Aphananthe aspera	LOTUS Database	35616633
Camptotheca acuminata	LOTUS Database	35616633
Cleidion brevipetiolatum	LOTUS Database	35616633
Dipentodon sinicus	LOTUS Database	35616633
Euphorbia sessiliflora	LOTUS Database	35616633
Phyllagathis rotundifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c20-gibberellin 6-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C20-gibberellin 6-carboxylic acids

Alternative Parents

Substituents

Gibberellane-6-carboxylic acid
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Aldehyde
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	0.48	ALOGPS
logP	-0.81	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	179.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	116.2 m³·mol⁻¹	ChemAxon
Polarizability	48.1 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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 6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione (NP0296843)

MOL for NP0296843 (6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

3D MOL for NP0296843 (6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

3D SDF for NP0296843 (6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

3D-SDF for NP0296843 (6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

PDB for NP0296843 (6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

3D PDB for NP0296843 (6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

SMILES for NP0296843 (6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

INCHI for NP0296843 (6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

Structure for NP0296843 (6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)

3D Structure for NP0296843 (6,7,14-trimethoxy-13-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione)