NP-MRD: Showing NP-Card for 2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one (NP0232989)

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Record Information

Version

2.0

Created at

2022-09-06 14:24:56 UTC

Updated at

2022-09-06 14:24:56 UTC

NP-MRD ID

NP0232989

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one

Description

2,5-Dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-15-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. 2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one is found in Croton kongensis. 2,5-Dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-15-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161514032D          

 22 25  0  0  0  0            999 V2000
    3.8136   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.7400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257    0.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9506   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -1.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469   -0.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586    1.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5987   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -1.6618    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2  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
 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
  7 18  1  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0232989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(O)CCCC2(C)C3CCC4CC3(C(O)CC12)C(=O)C4=C

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O3/c1-11-12-5-6-13-17(2)7-4-8-18(3,22)14(17)9-15(20)19(13,10-12)16(11)21/h12-15,20,22H,1,4-10H2,2-3H3

> <INCHI_KEY>
DJDKYDPOZMZQLR-UHFFFAOYSA-N

> <FORMULA>
C19H28O3

> <MOLECULAR_WEIGHT>
304.43

> <EXACT_MASS>
304.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.066605171131805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.614723756

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.96116817707767

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.311606335728218

> <JCHEM_PKA_STRONGEST_BASIC>
-2.899988776287909

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
85.11389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       7.119  -2.655   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.821  -1.826   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.230  -3.248   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.863  -0.692   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.402   0.777   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.899   1.113   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.857  -0.022   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.408   1.452   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.318  -1.491   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.285  -2.656   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.774  -2.341   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.778  -3.515   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.208  -0.872   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.322   0.124   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.752   0.996   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.296   2.224   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.874   1.924   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.328   0.347   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.466  -0.449   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.984  -0.707   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.306  -1.583   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.562  -3.102   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   18                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18   21                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    7   13                                                  
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₈O₃

Average Mass

304.4300 Da

Monoisotopic Mass

304.20384 Da

IUPAC Name

2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one

Traditional Name

2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one

CAS Registry Number

Not Available

SMILES

CC1(O)CCCC2(C)C3CCC4CC3(C(O)CC12)C(=O)C4=C

InChI Identifier

InChI=1S/C19H28O3/c1-11-12-5-6-13-17(2)7-4-8-18(3,22)14(17)9-15(20)19(13,10-12)16(11)21/h12-15,20,22H,1,4-10H2,2-3H3

InChI Key

DJDKYDPOZMZQLR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Croton kongensis	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
Tertiary alcohol
Cyclic alcohol
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	2.3	ALOGPS
logP	2.61	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.31	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.11 m³·mol⁻¹	ChemAxon
Polarizability	34.07 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

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 2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one (NP0232989)

MOL for NP0232989 (2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

3D MOL for NP0232989 (2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

3D SDF for NP0232989 (2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

3D-SDF for NP0232989 (2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

PDB for NP0232989 (2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

3D PDB for NP0232989 (2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

SMILES for NP0232989 (2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

INCHI for NP0232989 (2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

Structure for NP0232989 (2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

3D Structure for NP0232989 (2,5-dihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)