NP-MRD: Showing NP-Card for (1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde (NP0223920)

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Record Information

Version

2.0

Created at

2022-09-06 02:08:47 UTC

Updated at

2022-09-06 02:08:47 UTC

NP-MRD ID

NP0223920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde

Description

CHEMBL491381 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. (1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde is found in Annona squamosa and Bruguiera gymnorhiza. Based on a literature review very few articles have been published on CHEMBL491381.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204082D          

 23 26  0  0  1  0            999 V2000
    1.8257    0.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -0.0115    0.0000 C   0  0  1  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  1  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  0  0  0  0  0  0  0  0  0  0
    0.6469   -0.4671    0.0000 C   0  0  1  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  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
   -0.7854   -0.2403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4825    0.2009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2972   -0.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.6541    0.0000 O   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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  1  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 13 18  1  0  0  0  0
  2 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 13 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223920

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-17(12-21)7-3-8-18(2)15(17)6-9-19-10-14(4-5-16(18)19)20(23,11-19)13-22/h12,14-16,22-23H,3-11,13H2,1-2H3/t14-,15-,16+,17+,18-,19+,20+/m1/s1

> <INCHI_KEY>
ACIODAKBJVREKJ-MAPHFDCTSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
36.7745676523461

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5R,9S,10R,13R,14R)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde

> <JCHEM_LOGP>
2.6347431313333347

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.309321447654249

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.685426941359836

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0757507481986748

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
89.88649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,9S,10R,13R,14R)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde

> <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       3.408   1.452   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.857  -0.022   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.899   1.113   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.402   0.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.863  -0.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.821  -1.826   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.119  -2.655   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.230  -3.248   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.166  -4.471   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.318  -1.491   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.285  -2.656   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.774  -2.341   0.000  0.00  0.00           C+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  O   UNK     0      -2.767   0.375   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.422  -1.656   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.853  -3.088   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.306  -1.583   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   10                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8                                                            
CONECT   10    6    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18   23                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13    2                                                  
CONECT   19   15   20   21   23                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   19   13                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₃

Average Mass

320.4730 Da

Monoisotopic Mass

320.23514 Da

IUPAC Name

(1S,4S,5R,9S,10R,13R,14R)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde

Traditional Name

(1S,4S,5R,9S,10R,13R,14R)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O3/c1-17(12-21)7-3-8-18(2)15(17)6-9-19-10-14(4-5-16(18)19)20(23,11-19)13-22/h12,14-16,22-23H,3-11,13H2,1-2H3/t14-,15-,16+,17+,18-,19+,20+/m1/s1

InChI Key

ACIODAKBJVREKJ-MAPHFDCTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona squamosa	LOTUS Database	35616633
Bruguiera gymnorhiza	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
1,2-diol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Aldehyde
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	2.63	ChemAxon
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	-3.1	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	2	ChemAxon
Refractivity	89.89 m³·mol⁻¹	ChemAxon
Polarizability	36.77 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

24704881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44575992

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde (NP0223920)

MOL for NP0223920 ((1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde)

3D MOL for NP0223920 ((1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde)

3D SDF for NP0223920 ((1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde)

3D-SDF for NP0223920 ((1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde)

PDB for NP0223920 ((1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde)

3D PDB for NP0223920 ((1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde)

SMILES for NP0223920 ((1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde)

INCHI for NP0223920 ((1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde)

Structure for NP0223920 ((1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde)

3D Structure for NP0223920 ((1s,4s,5r,9s,10r,13r,14r)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde)