NP-MRD: Showing NP-Card for (1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one (NP0217604)

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Record Information

Version

2.0

Created at

2022-09-05 18:00:32 UTC

Updated at

2022-09-05 18:00:32 UTC

NP-MRD ID

NP0217604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one

Description

CHEMBL398310 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. (1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one is found in Croton kongensis. Based on a literature review very few articles have been published on CHEMBL398310.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052220002D          

 23 26  0  0  1  0            999 V2000
   -1.5987   -0.3788    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
   -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
    0.6469   -0.4671    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1725    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  1  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  1  0  0  0  0  0  0  0  0  0
    2.0661   -0.0115    0.0000 C   0  0  2  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
    2.6242    0.5960    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
    3.6765   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.9782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8136   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -2.3952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -0.7987    0.0000 C   0  0  1  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  1  0  0  0  0  0  0  0  0  0
    0.4166   -1.8832    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  6  1  1  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  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  1  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0217604

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(CO)CCC[C@@]2(C)[C@@H]3CC[C@@H]4C[C@@]3([C@H](O)C[C@H]12)C(=O)C4=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-12-13-5-6-14-19(3)8-4-7-18(2,11-21)15(19)9-16(22)20(14,10-13)17(12)23/h13-16,21-22H,1,4-11H2,2-3H3/t13-,14+,15-,16-,18-,19+,20-/m1/s1

> <INCHI_KEY>
PHXVQRJHPRPGAN-UUTQPTAWSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.39985193335589

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4S,5S,9R,10S,13R)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-one

> <JCHEM_LOGP>
2.9492069443333344

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.592292919608486

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.502159771184644

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2274809745522703

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
89.68159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5S,9R,10S,13R)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.984  -0.707   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.466  -0.449   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.306  -1.583   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.562  -3.102   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.208  -0.872   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.322   0.124   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.752   0.996   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.296   2.224   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.874   1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.328   0.347   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.857  -0.022   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.408   1.452   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.899   1.113   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.402   0.777   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.863  -0.692   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.821  -1.826   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.119  -2.655   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.230  -3.248   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.166  -4.471   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.318  -1.491   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.285  -2.656   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.774  -2.341   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.778  -3.515   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10   22                                             
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   13   20                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   20                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   16   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    5   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

C₂₀H₃₀O₃

Average Mass

318.4570 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

(1R,2R,4S,5S,9R,10S,13R)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-one

Traditional Name

(1R,2R,4S,5S,9R,10S,13R)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-one

CAS Registry Number

Not Available

SMILES

C[C@]1(CO)CCC[C@@]2(C)[C@@H]3CC[C@@H]4C[C@@]3([C@H](O)C[C@H]12)C(=O)C4=C

InChI Identifier

InChI=1S/C20H30O3/c1-12-13-5-6-14-19(3)8-4-7-18(2,11-21)15(19)9-16(22)20(14,10-13)17(12)23/h13-16,21-22H,1,4-11H2,2-3H3/t13-,14+,15-,16-,18-,19+,20-/m1/s1

InChI Key

PHXVQRJHPRPGAN-UUTQPTAWSA-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
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
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	2.95	ChemAxon
pKa (Strongest Acidic)	14.5	ChemAxon
pKa (Strongest Basic)	-1.2	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	1	ChemAxon
Refractivity	89.68 m³·mol⁻¹	ChemAxon
Polarizability	36.4 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

23311362

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44445573

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one (NP0217604)

MOL for NP0217604 ((1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

3D MOL for NP0217604 ((1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

3D SDF for NP0217604 ((1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

3D-SDF for NP0217604 ((1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

PDB for NP0217604 ((1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

3D PDB for NP0217604 ((1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

SMILES for NP0217604 ((1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

INCHI for NP0217604 ((1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

Structure for NP0217604 ((1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)

3D Structure for NP0217604 ((1r,2r,4s,5s,9r,10s,13r)-2-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one)