NP-MRD: Showing NP-Card for (+)-Casearinol A (NP0083296)

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Record Information

Version

2.0

Created at

2022-04-29 04:20:35 UTC

Updated at

2022-04-29 04:20:35 UTC

NP-MRD ID

NP0083296

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Casearinol A

Description

(1R,3S,5R,6aR,7S,8S,10R,10aS,10bS)-1,3-bis(acetyloxy)-10-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-decahydro-1H-naphtho[4,4a-c]furan-5-yl (2E)-2-methylbut-2-enoate 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. (+)-Casearinol A is found in Casearia guianensis. Based on a literature review very few articles have been published on (1R,3S,5R,6aR,7S,8S,10R,10aS,10bS)-1,3-bis(acetyloxy)-10-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-decahydro-1H-naphtho[4,4a-c]furan-5-yl (2E)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206202D          

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M  END

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M  END


  Mrv1652304292206202D          

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   -0.7708   -3.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2999   -2.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544   -4.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252   -4.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6627   -2.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518   -1.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  1  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  6  0  0  0
 10 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 19 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  3 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
  3 36  1  6  0  0  0
  2 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0083296

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@H]1C[C@@H]2[C@H](OC(C)=O)O[C@H](OC(C)=O)[C@]22[C@H](O)C[C@H](C)[C@](C)(C\C=C(/C)C=C)[C@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O8/c1-9-16(3)11-12-28(8)18(5)13-24(32)29-22(26(34-19(6)30)37-27(29)35-20(7)31)14-21(15-23(28)29)36-25(33)17(4)10-2/h9-11,18,21-24,26-27,32H,1,12-15H2,2-8H3/b16-11+,17-10+/t18-,21-,22+,23+,24+,26+,27-,28-,29+/m0/s1

> <INCHI_KEY>
GOBFDVWAFVUYAI-QZASWQOZSA-N

> <FORMULA>
C29H42O8

> <MOLECULAR_WEIGHT>
518.647

> <EXACT_MASS>
518.287968312

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
57.71035881741018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,5R,6aR,7S,8S,10R,10aS,10bS)-1,3-bis(acetyloxy)-10-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-decahydro-1H-naphtho[1,8a-c]furan-5-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
4.640806801666668

> <ALOGPS_LOGS>
-5.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.511437675820044

> <JCHEM_PKA_STRONGEST_BASIC>
-3.012497160596312

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
138.09480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.13e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5R,6aR,7S,8S,10R,10aS,10bS)-1,3-bis(acetyloxy)-10-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-decahydronaphtho[1,8a-c]furan-5-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.288  -0.743   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.308  -2.283   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.015  -3.071   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.359  -2.318   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.379  -0.778   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.003  -0.200   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.576   1.428   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.723  -0.026   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.046  -0.813   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.026  -2.353   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.682  -3.106   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.508  -3.065   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.025  -2.623   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.391  -1.127   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.137  -3.688   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.771  -5.183   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.884  -6.248   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.616  -3.257   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.422   1.485   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.893   1.666   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.248   0.267   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.584   0.499   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.650   1.815   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.171   1.574   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.098   3.253   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.612   2.689   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.605   4.272   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.268   5.036   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.935   5.047   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.617  -4.719   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.078  -6.190   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.439  -6.454   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.427  -5.273   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.968  -7.900   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.980  -9.082   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.237  -4.228   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.710  -3.194   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   37                                                  
CONECT    3    2    4   30   36                                             
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8   21                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15                                                            
CONECT   19    8   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20    5   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   19   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    3   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36    3                                                            
CONECT   37    2                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
(1R,3S,5R,6AR,7S,8S,10R,10as,10BS)-1,3-bis(acetyloxy)-10-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-decahydro-1H-naphtho[4,4a-c]furan-5-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₉H₄₂O₈

Average Mass

518.6470 Da

Monoisotopic Mass

518.28797 Da

IUPAC Name

(1R,3S,5R,6aR,7S,8S,10R,10aS,10bS)-1,3-bis(acetyloxy)-10-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-decahydro-1H-naphtho[1,8a-c]furan-5-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1R,3S,5R,6aR,7S,8S,10R,10aS,10bS)-1,3-bis(acetyloxy)-10-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-decahydronaphtho[1,8a-c]furan-5-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@H]1C[C@@H]2[C@H](OC(C)=O)O[C@H](OC(C)=O)[C@]22[C@H](O)C[C@H](C)[C@](C)(C\C=C(/C)C=C)[C@H]2C1

InChI Identifier

InChI=1S/C29H42O8/c1-9-16(3)11-12-28(8)18(5)13-24(32)29-22(26(34-19(6)30)37-27(29)35-20(7)31)14-21(15-23(28)29)36-25(33)17(4)10-2/h9-11,18,21-24,26-27,32H,1,12-15H2,2-8H3/b16-11+,17-10+/t18-,21-,22+,23+,24+,26+,27-,28-,29+/m0/s1

InChI Key

GOBFDVWAFVUYAI-QZASWQOZSA-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
Casearia guianensis	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
Naphthofuran
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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
logP	4.13	ALOGPS
logP	4.64	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	14.51	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	138.09 m³·mol⁻¹	ChemAxon
Polarizability	57.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

163047205

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Casearinol A (NP0083296)

MOL for NP0083296 ((+)-Casearinol A)

3D MOL for NP0083296 ((+)-Casearinol A)

3D SDF for NP0083296 ((+)-Casearinol A)

3D-SDF for NP0083296 ((+)-Casearinol A)

PDB for NP0083296 ((+)-Casearinol A)

3D PDB for NP0083296 ((+)-Casearinol A)

SMILES for NP0083296 ((+)-Casearinol A)

INCHI for NP0083296 ((+)-Casearinol A)

Structure for NP0083296 ((+)-Casearinol A)

3D Structure for NP0083296 ((+)-Casearinol A)