NP-MRD: Showing NP-Card for (1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate (NP0290896)

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Record Information

Version

1.0

Created at

2022-09-09 21:46:58 UTC

Updated at

2022-09-09 21:46:58 UTC

NP-MRD ID

NP0290896

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate

Description

Glanduline 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,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate is found in Consolida glandulosa. Based on a literature review very few articles have been published on Glanduline.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092223462D          

 36 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092223462D          

 36 42  0  0  1  0            999 V2000
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    6.8394   -1.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5464   -2.0214    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  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  1  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17  2  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 12 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0290896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)O[C@@H]1C[C@@]23[C@@H]4[C@@H]5C[C@@]67CC(=C)[C@@H](C(O)[C@]6(O)[C@H]2N5C[C@@]4(C)[C@@H]1OC(C)=O)[C@@H](O)[C@@]37O

> <INCHI_IDENTIFIER>
InChI=1S/C27H37NO8/c1-6-11(2)21(32)36-15-9-25-17-14-8-24-7-12(3)16(19(31)27(24,25)34)18(30)26(24,33)22(25)28(14)10-23(17,5)20(15)35-13(4)29/h11,14-20,22,30-31,33-34H,3,6-10H2,1-2,4-5H3/t11?,14-,15+,16-,17+,18?,19+,20+,22-,23+,24-,25+,26-,27-/m0/s1

> <INCHI_KEY>
SQVLUNIFVQDZEK-KLCLLCPWSA-N

> <FORMULA>
C27H37NO8

> <MOLECULAR_WEIGHT>
503.592

> <EXACT_MASS>
503.251917155

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.20329937770959

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,4S,5S,8S,9R,11R,14R,16S,17R,18R,19R)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl 2-methylbutanoate

> <JCHEM_LOGP>
-0.6961306250000007

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.178490836417776

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.516170005715281

> <JCHEM_PKA_STRONGEST_BASIC>
8.214243597346247

> <JCHEM_POLAR_SURFACE_AREA>
136.76000000000002

> <JCHEM_REFRACTIVITY>
124.00249999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4S,5S,8S,9R,11R,14R,16S,17R,18R,19R)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl 2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.311   0.764   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.728   0.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.371   1.778   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.077   1.185   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.643   1.921   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.202   1.174   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.372  -0.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.546  -1.242   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.210  -2.713   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.164  -1.998   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.324  -0.638   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.898  -1.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.391  -0.627   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.579  -0.392   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.203  -1.750   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.982  -3.348   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.060  -0.854   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.363  -0.070   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.399   1.859   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.129   0.314   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.918  -1.554   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.794   0.287   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.483   1.113   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.119   0.778   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.981   2.141   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.539   2.333   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.058   0.883   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.529   3.501   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.048   4.964   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.103   3.173   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.130   4.321   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.997  -0.583   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.572  -1.104   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.232  -2.509   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.767  -2.638   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.353  -3.773   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13   20                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9   10   32                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12    4   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    4   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   12    7   23                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   24    8   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₇NO₈

Average Mass

503.5920 Da

Monoisotopic Mass

503.25192 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)O[C@@H]1C[C@@]23[C@@H]4[C@@H]5C[C@@]67CC(=C)[C@@H](C(O)[C@]6(O)[C@H]2N5C[C@@]4(C)[C@@H]1OC(C)=O)[C@@H](O)[C@@]37O

InChI Identifier

InChI=1S/C27H37NO8/c1-6-11(2)21(32)36-15-9-25-17-14-8-24-7-12(3)16(19(31)27(24,25)34)18(30)26(24,33)22(25)28(14)10-23(17,5)20(15)35-13(4)29/h11,14-20,22,30-31,33-34H,3,6-10H2,1-2,4-5H3/t11?,14-,15+,16-,17+,18?,19+,20+,22-,23+,24-,25+,26-,27-/m0/s1

InChI Key

SQVLUNIFVQDZEK-KLCLLCPWSA-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
Consolida glandulosa	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
Quinolizidine
Azaspirodecane
Alkaloid or derivatives
Isoindole or derivatives
Isoindoline
Indolizidine
Indole or derivatives
Fatty acid ester
Azepane
Fatty acyl
N-alkylpyrrolidine
Piperidine
Dicarboxylic acid or derivatives
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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

C00024798

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

102066388

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate (NP0290896)

MOL for NP0290896 ((1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate)

3D MOL for NP0290896 ((1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate)

3D SDF for NP0290896 ((1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate)

3D-SDF for NP0290896 ((1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate)

PDB for NP0290896 ((1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate)

3D PDB for NP0290896 ((1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate)

SMILES for NP0290896 ((1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate)

INCHI for NP0290896 ((1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate)

Structure for NP0290896 ((1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate)

3D Structure for NP0290896 ((1r,3r,4s,5s,8s,9r,11r,14r,16s,17r,18r,19r)-4-(acetyloxy)-9,10,18,19-tetrahydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate)