NP-MRD: Showing NP-Card for 3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one (NP0233605)

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Record Information

Version

2.0

Created at

2022-09-06 15:16:11 UTC

Updated at

2022-09-06 15:16:11 UTC

NP-MRD ID

NP0233605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

Description

3,9,10,13-Tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]Octadecan-7-one belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. 3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one is found in Isodon henryi. 3,9,10,13-Tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]Octadecan-7-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241509542D          

 26 30  0  0  0  0            999 V2000
    7.4067    1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7458    0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3086    1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3037    0.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0972    0.3403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1609   -0.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3968   -1.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7123   -0.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0752   -0.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2587    0.6033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138    0.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0777    1.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5163    1.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8471    1.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9848    0.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789    0.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9703   -0.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696   -1.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4198   -1.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775   -2.1766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7872   -0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8245   -0.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    0.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4857    0.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837    1.2805    0.0000 O   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
  4  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
  8 15  1  0  0  0  0
 11 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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  8 22  1  0  0  0  0
 16 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END


  Mrv1533004241509542D          

 26 30  0  0  0  0            999 V2000
    7.4067    1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7458    0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3086    1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3037    0.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0972    0.3403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1609   -0.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3968   -1.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7123   -0.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0752   -0.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2587    0.6033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138    0.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0777    1.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5163    1.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8471    1.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9848    0.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789    0.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9703   -0.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696   -1.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4198   -1.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775   -2.1766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7872   -0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8245   -0.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    0.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4857    0.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837    1.2805    0.0000 O   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
  4  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
  8 15  1  0  0  0  0
 11 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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  8 22  1  0  0  0  0
 16 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0233605

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(O)CCC23COC(O)(C(O)C12)C12CC(CC(O)C31)C(=C)C2=O

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

> <INCHI_KEY>
NGTJHRUNHBCVEM-UHFFFAOYSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.81718352722807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
0.3847007340000008

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.71416859134871

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.588858821717066

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8584426198548485

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
92.03129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      13.826   2.311   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.592   1.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.776   2.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.634   0.214   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      15.115   0.635   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      13.367  -1.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.941  -1.993   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.663  -1.017   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.474  -0.251   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.816   1.126   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.612   1.784   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.612   2.955   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.297   2.155   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.915   3.566   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.172   0.658   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.987   0.186   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.878  -0.952   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.545  -1.708   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.663  -2.857   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.250  -2.782   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.105  -4.063   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.936  -1.333   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.272  -0.128   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.832   0.418   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.507   0.862   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.316   2.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   15                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   15   22                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   16                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    2    8                                                  
CONECT   16   11   17   22   25                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    8   16                                                  
CONECT   23   18   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
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

3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

Traditional Name

3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

CAS Registry Number

Not Available

SMILES

CC1(C)C(O)CCC23COC(O)(C(O)C12)C12CC(CC(O)C31)C(=C)C2=O

InChI Identifier

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

InChI Key

NGTJHRUNHBCVEM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon henryi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Oxane
Cyclic alcohol
Hemiacetal
Ketone
Secondary alcohol
Oxacycle
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	-0.02	ALOGPS
logP	0.38	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	10.59	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	92.03 m³·mol⁻¹	ChemAxon
Polarizability	37.82 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

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 3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one (NP0233605)

MOL for NP0233605 (3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D MOL for NP0233605 (3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D SDF for NP0233605 (3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D-SDF for NP0233605 (3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

PDB for NP0233605 (3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D PDB for NP0233605 (3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

SMILES for NP0233605 (3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

INCHI for NP0233605 (3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

Structure for NP0233605 (3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D Structure for NP0233605 (3,9,10,13-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)