NP-MRD: Showing NP-Card for 16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene (NP0065637)

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Record Information

Version

2.0

Created at

2022-04-28 09:49:34 UTC

Updated at

2022-04-28 09:49:34 UTC

NP-MRD ID

NP0065637

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene

Description

3-{[(4AR,5S,6S,7R,8aR)-5-[(3S)-5-(acetyloxy)-3-[(acetyloxy)methyl]pentyl]-7-hydroxy-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methoxy}-3-oxopropanoic acid belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene is found in Baccharis genistelloides and Baccharis trimera . Based on a literature review very few articles have been published on 3-{[(4aR,5S,6S,7R,8aR)-5-[(3S)-5-(acetyloxy)-3-[(acetyloxy)methyl]pentyl]-7-hydroxy-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methoxy}-3-oxopropanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282211492D          

 36 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282211492D          

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   -2.3038   -6.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2751   -6.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9747   -7.2879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466   -7.2381    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  6  0  0  0
  8 12  1  6  0  0  0
  7 13  1  6  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  7 27  1  1  0  0  0
  4 28  1  6  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0065637

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H](O)C[C@]2(C)[C@H](CCC=C2COC(=O)CC(O)=O)[C@]1(C)CC[C@@H](CCOC(C)=O)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O9/c1-17-22(30)14-27(5)21(16-36-25(33)13-24(31)32)7-6-8-23(27)26(17,4)11-9-20(15-35-19(3)29)10-12-34-18(2)28/h7,17,20,22-23,30H,6,8-16H2,1-5H3,(H,31,32)/t17-,20+,22-,23-,26-,27+/m1/s1

> <INCHI_KEY>
MMBVEWKIJKMBGB-XILKNQBRSA-N

> <FORMULA>
C27H42O9

> <MOLECULAR_WEIGHT>
510.624

> <EXACT_MASS>
510.282882932

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.155056817448624

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(4aR,5S,6S,7R,8aR)-5-[(3S)-5-(acetyloxy)-3-[(acetyloxy)methyl]pentyl]-7-hydroxy-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methoxy}-3-oxopropanoic acid

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
2.618392634000001

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.938524376228099

> <JCHEM_PKA_STRONGEST_BASIC>
-0.610956379082476

> <JCHEM_POLAR_SURFACE_AREA>
136.43

> <JCHEM_REFRACTIVITY>
131.44779999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(4aR,5S,6S,7R,8aR)-5-[(3S)-5-(acetyloxy)-3-[(acetyloxy)methyl]pentyl]-7-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -8.541  -4.463   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.487  -6.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.127  -6.725   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.821  -5.909   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.875  -4.370   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.235  -3.647   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.569  -3.554   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.209  -4.277   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.156  -5.816   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.462  -6.632   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.796  -6.539   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.904  -3.461   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.339  -2.220   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.569  -0.886   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.339   0.447   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.879   0.447   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.649   1.781   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.879   3.115   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.339   3.115   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.569   4.448   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.932   2.488   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.569   1.781   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.029   1.781   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.259   3.115   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.029   4.448   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.719   3.115   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.894  -2.170   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.768  -7.448   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.074  -8.264   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.714  -8.987   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.660 -10.526   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.966 -11.342   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.301 -11.249   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.247 -12.788   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -5.553 -13.604   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -2.887 -13.511   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5   10   28                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   13   27                                             
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13    7   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    7                                                            
CONECT   28    4                                                            
CONECT   29    3   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
3-{[(4ar,5S,6S,7R,8ar)-5-[(3S)-5-(acetyloxy)-3-[(acetyloxy)methyl]pentyl]-7-hydroxy-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methoxy}-3-oxopropanoate	Generator

Chemical Formula

C₂₇H₄₂O₉

Average Mass

510.6240 Da

Monoisotopic Mass

510.28288 Da

IUPAC Name

3-{[(4aR,5S,6S,7R,8aR)-5-[(3S)-5-(acetyloxy)-3-[(acetyloxy)methyl]pentyl]-7-hydroxy-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methoxy}-3-oxopropanoic acid

Traditional Name

3-{[(4aR,5S,6S,7R,8aR)-5-[(3S)-5-(acetyloxy)-3-[(acetyloxy)methyl]pentyl]-7-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H](O)C[C@]2(C)[C@H](CCC=C2COC(=O)CC(O)=O)[C@]1(C)CC[C@@H](CCOC(C)=O)COC(C)=O

InChI Identifier

InChI=1S/C27H42O9/c1-17-22(30)14-27(5)21(16-36-25(33)13-24(31)32)7-6-8-23(27)26(17,4)11-9-20(15-35-19(3)29)10-12-34-18(2)28/h7,17,20,22-23,30H,6,8-16H2,1-5H3,(H,31,32)/t17-,20+,22-,23-,26-,27+/m1/s1

InChI Key

MMBVEWKIJKMBGB-XILKNQBRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Baccharis genistelloides	LOTUS Database	35616633
Baccharis trimera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Tetracarboxylic acid or derivatives
1,3-dicarbonyl compound
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
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	4.09	ALOGPS
logP	2.62	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-0.61	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	136.43 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	131.45 m³·mol⁻¹	ChemAxon
Polarizability	56.16 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163105056

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene (NP0065637)

MOL for NP0065637 (16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene)

3D MOL for NP0065637 (16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene)

3D SDF for NP0065637 (16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene)

3D-SDF for NP0065637 (16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene)

PDB for NP0065637 (16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene)

3D PDB for NP0065637 (16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene)

SMILES for NP0065637 (16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene)

INCHI for NP0065637 (16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene)

Structure for NP0065637 (16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene)

3D Structure for NP0065637 (16-Diacetoxy-7alpha-hydroxy-18-malonyloxy-ent-cleroda-3-ene)