NP-MRD: Showing NP-Card for 7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one (NP0254794)

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Record Information

Version

2.0

Created at

2022-09-07 19:04:06 UTC

Updated at

2022-09-07 19:04:06 UTC

NP-MRD ID

NP0254794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one

Description

7,9,10,18-Tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]Octadecan-16-one belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one is found in Isodon adenolomus, Isodon rubescens and Isodon ternifolius. 7,9,10,18-Tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]Octadecan-16-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191513422D          

 26 30  0  0  0  0            999 V2000
    7.5966    1.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9076    0.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5883    1.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4889   -0.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2394   -0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4196   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7457   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8365   -0.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3992   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -1.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937   -0.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026   -0.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144   -1.1535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    0.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4673    0.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3521    1.2241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6558    0.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1131    1.5619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3588    0.6155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0615   -0.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2812   -0.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412    1.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8227    1.9682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0672    0.4189    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
  2  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
  7  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
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  2  0  0  0  0
 14 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
  7 22  1  0  0  0  0
 22 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  2 26  1  0  0  0  0
  7 26  1  0  0  0  0
M  END


  Mrv1533004191513422D          

 26 30  0  0  0  0            999 V2000
    7.5966    1.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9076    0.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5883    1.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4889   -0.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2394   -0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4196   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7457   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8365   -0.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3992   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -1.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937   -0.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026   -0.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144   -1.1535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    0.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4673    0.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3521    1.2241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834   -0.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6558    0.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1131    1.5619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3588    0.6155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0615   -0.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2812   -0.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5412    1.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8227    1.9682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0672    0.4189    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
  2  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
  7  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
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  2  0  0  0  0
 14 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
  7 22  1  0  0  0  0
 22 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  2 26  1  0  0  0  0
  7 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254794

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC23C4CCC5C(O)C4(C(O)C5=C)C(O)(OC2=O)C(O)C13

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-9-10-5-6-11-18-8-4-7-17(2,3)12(18)15(23)20(25,26-16(18)24)19(11,13(9)21)14(10)22/h10-15,21-23,25H,1,4-8H2,2-3H3

> <INCHI_KEY>
DWBNAAUVBIEEOE-UHFFFAOYSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.575611900708175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
0.8270959593333338

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.481753550875286

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.461211466227539

> <JCHEM_PKA_STRONGEST_BASIC>
-3.173422548854817

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
90.9387

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one

> <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      14.180   1.967   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.894   1.120   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.298   2.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.979  -0.004   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.514  -1.496   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.983  -1.840   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.725  -0.852   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.028  -1.270   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.212  -2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.636  -2.939   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.588  -1.729   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.912  -0.945   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.867  -2.153   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.006   0.190   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.472   0.760   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.257   2.285   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.196  -0.183   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.745   0.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.691   1.756   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.678   2.916   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.003   1.149   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.448  -0.146   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.992  -0.646   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.344   2.226   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.869   3.674   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.326   0.782   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   26                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   22   26                                             
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15   19                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17                                                            
CONECT   19   14   20   21   24                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    7   23                                                  
CONECT   23   22                                                            
CONECT   24   19   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₆

Average Mass

364.4380 Da

Monoisotopic Mass

364.18859 Da

IUPAC Name

7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one

Traditional Name

7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one

CAS Registry Number

Not Available

SMILES

CC1(C)CCCC23C4CCC5C(O)C4(C(O)C5=C)C(O)(OC2=O)C(O)C13

InChI Identifier

InChI=1S/C20H28O6/c1-9-10-5-6-11-18-8-4-7-17(2,3)12(18)15(23)20(25,26-16(18)24)19(11,13(9)21)14(10)22/h10-15,21-23,25H,1,4-8H2,2-3H3

InChI Key

DWBNAAUVBIEEOE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon adenolomus	LOTUS Database	35616633
Isodon rubescens	LOTUS Database	35616633
Isodon ternifolius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Kaurane diterpenoid
Delta valerolactone
Delta_valerolactone
Oxane
Cyclic alcohol
Carboxylic acid ester
Hemiacetal
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	0.63	ALOGPS
logP	0.83	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	10.46	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.94 m³·mol⁻¹	ChemAxon
Polarizability	37.58 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

14564527

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one (NP0254794)

MOL for NP0254794 (7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one)

3D MOL for NP0254794 (7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one)

3D SDF for NP0254794 (7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one)

3D-SDF for NP0254794 (7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one)

PDB for NP0254794 (7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one)

3D PDB for NP0254794 (7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one)

SMILES for NP0254794 (7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one)

INCHI for NP0254794 (7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one)

Structure for NP0254794 (7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one)

3D Structure for NP0254794 (7,9,10,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-16-one)