NP-MRD: Showing NP-Card for 7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol (NP0327013)

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Record Information

Version

2.0

Created at

2022-09-12 09:10:37 UTC

Updated at

2022-09-12 09:10:37 UTC

NP-MRD ID

NP0327013

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol

Description

7-(Hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]Tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol is found in Isodon lophanthoides. 7-(Hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]Tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191523342D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004191523342D          

 35 39  0  0  0  0            999 V2000
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  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 15 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
 26 29  1  0  0  0  0
 13 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 10 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
  7 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327013

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC2(O)CC3=C(O)C4=C(C=C3C(O)CC12)C(C)(C)OC1C(O)C(O)C(CO)OC1O4

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O9/c1-24(2)6-5-7-26(32)10-13-12(15(28)9-17(24)26)8-14-21(18(13)29)34-23-22(35-25(14,3)4)20(31)19(30)16(11-27)33-23/h8,15-17,19-20,22-23,27-32H,5-7,9-11H2,1-4H3

> <INCHI_KEY>
MYMKTYUESXZKHY-UHFFFAOYSA-N

> <FORMULA>
C26H38O9

> <MOLECULAR_WEIGHT>
494.581

> <EXACT_MASS>
494.251582804

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.259997133458654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
1.204826722666666

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.69321412242942

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.66691026384894

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092569777436

> <JCHEM_POLAR_SURFACE_AREA>
149.07

> <JCHEM_REFRACTIVITY>
125.25150000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.180  -9.828   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.583  -9.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.963 -10.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.716  -7.922   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.384  -6.535   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.920  -6.420   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.787  -7.692   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.350  -6.259   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.289  -7.349   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.493  -8.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.826  -7.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.826  -6.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.160  -8.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.364  -7.349   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.865  -7.692   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.733  -6.420   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      14.269  -6.535   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.136  -5.262   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.468  -3.875   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.937  -7.922   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.472  -8.037   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.069  -9.195   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.737 -10.582   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.534  -9.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.865 -10.467   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.364 -10.810   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.032 -12.197   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.160 -11.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.160  -9.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.826 -10.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.493  -9.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.289 -10.810   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.631 -12.311   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.787 -10.467   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.119  -9.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   35                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   35                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   31                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   29                                                  
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   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   13   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   10   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈O₉

Average Mass

494.5810 Da

Monoisotopic Mass

494.25158 Da

IUPAC Name

7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol

Traditional Name

7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol

CAS Registry Number

Not Available

SMILES

CC1(C)CCCC2(O)CC3=C(O)C4=C(C=C3C(O)CC12)C(C)(C)OC1C(O)C(O)C(CO)OC1O4

InChI Identifier

InChI=1S/C26H38O9/c1-24(2)6-5-7-26(32)10-13-12(15(28)9-17(24)26)8-14-21(18(13)29)34-23-22(35-25(14,3)4)20(31)19(30)16(11-27)33-23/h8,15-17,19-20,22-23,27-32H,5-7,9-11H2,1-4H3

InChI Key

MYMKTYUESXZKHY-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
Isodon lophanthoides	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

Abeoabietane diterpenoid
Diterpenoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Monosaccharide
Oxane
Benzenoid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Organoheterocyclic compound
Acetal
Ether
Oxacycle
Dialkyl ether
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
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	0.84	ALOGPS
logP	1.2	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	149.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	125.25 m³·mol⁻¹	ChemAxon
Polarizability	53.26 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

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 7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol (NP0327013)

MOL for NP0327013 (7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol)

3D MOL for NP0327013 (7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol)

3D SDF for NP0327013 (7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol)

3D-SDF for NP0327013 (7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol)

PDB for NP0327013 (7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol)

3D PDB for NP0327013 (7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol)

SMILES for NP0327013 (7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol)

INCHI for NP0327013 (7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol)

Structure for NP0327013 (7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol)

3D Structure for NP0327013 (7-(hydroxymethyl)-12,12,19,19-tetramethyl-4,6,11-trioxapentacyclo[13.9.0.0³,¹³.0⁵,¹⁰.0¹⁸,²³]tetracosa-1,3(13),14-triene-2,8,9,16,23-pentol)