NP-MRD: Showing NP-Card for (1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione (NP0226654)

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Record Information

Version

2.0

Created at

2022-09-06 05:46:07 UTC

Updated at

2022-09-06 05:46:08 UTC

NP-MRD ID

NP0226654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione

Description

(1R,4R,9R,10R,12R,13S)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]Hexadecane-6,14-dione belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. (1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione is found in Euphorbia antiquorum. Based on a literature review very few articles have been published on (1R,4R,9R,10R,12R,13S)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]Hexadecane-6,14-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207462D          

 23 26  0  0  1  0            999 V2000
   -1.2188   -0.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025   -0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1053    0.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0445    0.6763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6102    1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4283    1.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653    0.8763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6866    0.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4669    1.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4316    1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1650    0.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9862    0.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8221   -0.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0008   -0.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224    0.1259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1825   -0.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6489    0.0356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1229   -0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753   -0.7198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5589    0.0811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3560    0.2938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445    0.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844    1.6158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  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
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  6  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0226654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2CC[C@@]34CC(=C)[C@@H](C[C@@H]3[C@]2(C)CCC1=O)[C@H](O)C4=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-11-10-20-8-5-13-18(2,3)15(21)6-7-19(13,4)14(20)9-12(11)16(22)17(20)23/h12-14,16,22H,1,5-10H2,2-4H3/t12-,13+,14-,16+,19-,20-/m1/s1

> <INCHI_KEY>
UQKJSKXVMBIKGF-BBDKCBRUSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.388055469824394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,9R,10R,12R,13S)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadecane-6,14-dione

> <JCHEM_LOGP>
3.4884592520000015

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.956551026205318

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.082763970669578

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6373990138231367

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
88.448

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,9R,10R,12R,13S)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadecane-6,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.275  -0.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.751  -0.428   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.196   0.810   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.950   1.262   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.006   2.547   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.533   2.973   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.349   1.636   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.882   1.782   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.472   3.266   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.272   2.443   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.775   0.527   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.308   0.673   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.135  -0.874   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.601  -1.020   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.708   0.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.074  -1.168   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.078   0.066   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.096  -1.242   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.514  -1.344   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.043   0.151   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.531   0.548   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.643   1.834   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.344   3.016   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17   22                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15    4   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    4   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4410 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(1R,4R,9R,10R,12R,13S)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadecane-6,14-dione

Traditional Name

(1R,4R,9R,10R,12R,13S)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadecane-6,14-dione

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H]2CC[C@@]34CC(=C)[C@@H](C[C@@H]3[C@]2(C)CCC1=O)[C@H](O)C4=O

InChI Identifier

InChI=1S/C20H28O3/c1-11-10-20-8-5-13-18(2,3)15(21)6-7-19(13,4)14(20)9-12(11)16(22)17(20)23/h12-14,16,22H,1,5-10H2,2-4H3/t12-,13+,14-,16+,19-,20-/m1/s1

InChI Key

UQKJSKXVMBIKGF-BBDKCBRUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia antiquorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Alkaloid or derivatives
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.49	ChemAxon
pKa (Strongest Acidic)	13.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.45 m³·mol⁻¹	ChemAxon
Polarizability	35.39 Å³	ChemAxon
Number of Rings	4	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

14262776

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione (NP0226654)

MOL for NP0226654 ((1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione)

3D MOL for NP0226654 ((1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione)

3D SDF for NP0226654 ((1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione)

3D-SDF for NP0226654 ((1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione)

PDB for NP0226654 ((1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione)

3D PDB for NP0226654 ((1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione)

SMILES for NP0226654 ((1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione)

INCHI for NP0226654 ((1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione)

Structure for NP0226654 ((1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione)

3D Structure for NP0226654 ((1r,4r,9r,10r,12r,13s)-13-hydroxy-5,5,9-trimethyl-16-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,14-dione)