NP-MRD: Showing NP-Card for (1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate (NP0296699)

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Record Information

Version

2.0

Created at

2022-09-10 06:26:20 UTC

Updated at

2022-09-10 06:26:21 UTC

NP-MRD ID

NP0296699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate

Description

CHEMBL500387 belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. (1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate is found in Croton ciliatoglandulifer. Based on a literature review very few articles have been published on CHEMBL500387.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102208262D          

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M  END


  Mrv1652309102208262D          

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    1.6875    0.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342   -0.0142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7271   -0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3775    0.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7555   -1.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4392   -1.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9801   -1.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725   -0.6980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7172   -0.3483    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5207   -0.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299    0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3059   -0.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  6  5  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 10 14  1  6  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17  6  1  0  0  0  0
 17 18  1  6  0  0  0
 19 17  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 33 32  1  1  0  0  0
 33 27  1  0  0  0  0
 19 33  1  0  0  0  0
 21 34  1  0  0  0  0
 34  5  1  0  0  0  0
 34 35  1  1  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296699

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H43NO7/c1-14(2)22(30(8)9)26(34)36-25-16(4)28(35)20-10-15(3)23(33)19(20)11-18(13-31)12-21(28)24-27(6,7)29(24,25)37-17(5)32/h10,12,14,16,19-22,24-25,31,35H,11,13H2,1-9H3/t16-,19-,20-,21+,22-,24-,25-,28+,29-/m1/s1

> <INCHI_KEY>
VCEYVQJHAJGATA-MBCQSGEESA-N

> <FORMULA>
C29H43NO7

> <MOLECULAR_WEIGHT>
517.663

> <EXACT_MASS>
517.303952729

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.9397932856441

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl (2R)-2-(dimethylamino)-3-methylbutanoate

> <JCHEM_LOGP>
2.3109018843333313

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.958277841421033

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.918196344247061

> <JCHEM_PKA_STRONGEST_BASIC>
6.725863328470953

> <JCHEM_POLAR_SURFACE_AREA>
113.37

> <JCHEM_REFRACTIVITY>
139.54370000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl (2R)-2-(dimethylamino)-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.733  -1.229   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.384  -2.729   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.508  -3.781   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.910  -3.176   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.786  -2.124   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.734  -3.248   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.181  -4.721   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.681  -5.071   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.733  -3.947   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.128  -6.545   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.628  -6.894   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.075  -8.368   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.680  -5.770   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -2.076  -7.669   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.576  -7.319   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.523  -9.142   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.766  -2.898   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.819  -4.023   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.214  -1.425   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.179  -2.625   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.161  -0.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.384   1.223   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.714   1.999   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.592   3.534   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.860   4.408   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.150   1.443   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.610  -0.027   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.091  -0.452   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.305   0.496   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.144  -1.991   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.420  -2.853   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.696  -2.517   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.749  -1.303   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.339  -0.650   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.839  -1.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.789   0.212   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.304  -0.527   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   34   35                                             
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    6   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   33                                             
CONECT   20   19                                                            
CONECT   21   19   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27   19                                                  
CONECT   34   21    5   35                                                  
CONECT   35   34    5   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₃NO₇

Average Mass

517.6630 Da

Monoisotopic Mass

517.30395 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](N(C)C)C(=O)O[C@@H]1[C@@H](C)[C@]2(O)[C@@H]3C=C(C)C(=O)[C@@H]3CC(CO)=C[C@H]2[C@@H]2C(C)(C)[C@]12OC(C)=O

InChI Identifier

InChI=1S/C29H43NO7/c1-14(2)22(30(8)9)26(34)36-25-16(4)28(35)20-10-15(3)23(33)19(20)11-18(13-31)12-21(28)24-27(6,7)29(24,25)37-17(5)32/h10,12,14,16,19-22,24-25,31,35H,11,13H2,1-9H3/t16-,19-,20-,21+,22-,24-,25-,28+,29-/m1/s1

InChI Key

VCEYVQJHAJGATA-MBCQSGEESA-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 ciliatoglandulifer	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Tigliane diterpenoid
Alpha-amino acid ester
Valine or derivatives
Alpha-amino acid or derivatives
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Ketone
Carboxylic acid derivative
Alcohol
Organonitrogen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
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

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

9824007

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11649268

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,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate (NP0296699)

MOL for NP0296699 ((1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate)

3D MOL for NP0296699 ((1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate)

3D SDF for NP0296699 ((1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate)

3D-SDF for NP0296699 ((1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate)

PDB for NP0296699 ((1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate)

3D PDB for NP0296699 ((1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate)

SMILES for NP0296699 ((1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate)

INCHI for NP0296699 ((1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate)

Structure for NP0296699 ((1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate)

3D Structure for NP0296699 ((1r,2r,6r,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl (2r)-2-(dimethylamino)-3-methylbutanoate)