NP-MRD: Showing NP-Card for (+)-Casearborin A (NP0081246)

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Record Information

Version

2.0

Created at

2022-04-29 02:12:29 UTC

Updated at

2022-04-29 02:12:29 UTC

NP-MRD ID

NP0081246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Casearborin A

Description

Casearborin A 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. (+)-Casearborin A is found in Casearia arborea. Based on a literature review very few articles have been published on Casearborin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204122D          

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M  END

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M  END


  Mrv1652304292204122D          

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   -0.9530   -4.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2621   -2.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -2.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4206   -1.6262    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
  5  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  9 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  3 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 34 37  1  0  0  0  0
  3 38  1  1  0  0  0
  2 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@]23[C@H](OC(C)=O)O[C@H](OC(C)=O)C2=C[C@@H](C[C@H]3[C@]1(C)C\C=C(/C)C=C)OC(=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O8/c1-7-18(2)12-14-30(6)19(3)13-15-31-25(28(36-20(4)32)39-29(31)37-21(5)33)16-24(17-26(30)31)38-27(35)22-8-10-23(34)11-9-22/h7-12,16,19,24,26,28-29,34H,1,13-15,17H2,2-6H3/b18-12+/t19-,24+,26+,28+,29-,30-,31-/m1/s1

> <INCHI_KEY>
RKOVIXOSRVSKPI-OLAUXWBOSA-N

> <FORMULA>
C31H38O8

> <MOLECULAR_WEIGHT>
538.637

> <EXACT_MASS>
538.256668184

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
57.99447803074205

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,5R,6aS,7R,8R,10aS)-1,3-bis(acetyloxy)-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate

> <ALOGPS_LOGP>
5.16

> <JCHEM_LOGP>
5.793047602666665

> <ALOGPS_LOGS>
-5.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.493088297595648

> <JCHEM_PKA_STRONGEST_BASIC>
-4.548291848226022

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
145.11620000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5R,6aS,7R,8R,10aS)-1,3-bis(acetyloxy)-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-1H,3H,5H,6H,6aH,8H,9H,10H-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate

> <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  C   UNK     0       2.723  -0.026   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.046  -0.813   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.026  -2.353   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.682  -3.106   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.350  -3.140   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.693  -2.388   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.713  -0.848   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.017  -3.175   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.360  -2.423   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.684  -3.210   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.664  -4.750   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.320  -5.503   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.997  -4.715   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.987  -5.538   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.422   1.485   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.893   1.666   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.248   0.267   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.262  -0.033   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.277   1.125   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.788   0.824   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.782   2.583   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.468   2.615   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.011   4.086   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.509   4.426   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.056   5.217   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.720  -4.440   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.113  -5.735   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.651  -5.661   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.484  -6.956   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.779  -8.325   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.356  -4.292   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.725  -4.421   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.652  -3.036   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   39                                                  
CONECT    3    2    4   32   38                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   23                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21    7   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22    5   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    3   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34                                                            
CONECT   38    3                                                            
CONECT   39    2                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₈O₈

Average Mass

538.6370 Da

Monoisotopic Mass

538.25667 Da

IUPAC Name

(1S,3R,5R,6aS,7R,8R,10aS)-1,3-bis(acetyloxy)-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate

Traditional Name

(1S,3R,5R,6aS,7R,8R,10aS)-1,3-bis(acetyloxy)-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-1H,3H,5H,6H,6aH,8H,9H,10H-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@]23[C@H](OC(C)=O)O[C@H](OC(C)=O)C2=C[C@@H](C[C@H]3[C@]1(C)C\C=C(/C)C=C)OC(=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C31H38O8/c1-7-18(2)12-14-30(6)19(3)13-15-31-25(28(36-20(4)32)39-29(31)37-21(5)33)16-24(17-26(30)31)38-27(35)22-8-10-23(34)11-9-22/h7-12,16,19,24,26,28-29,34H,1,13-15,17H2,2-6H3/b18-12+/t19-,24+,26+,28+,29-,30-,31-/m1/s1

InChI Key

RKOVIXOSRVSKPI-OLAUXWBOSA-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 arborea	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
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	5.16	ALOGPS
logP	5.79	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-4.5	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	145.12 m³·mol⁻¹	ChemAxon
Polarizability	57.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

C00047020

Chemspider ID

4509051

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352094

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Casearborin A (NP0081246)

MOL for NP0081246 ((+)-Casearborin A)

3D MOL for NP0081246 ((+)-Casearborin A)

3D SDF for NP0081246 ((+)-Casearborin A)

3D-SDF for NP0081246 ((+)-Casearborin A)

PDB for NP0081246 ((+)-Casearborin A)

3D PDB for NP0081246 ((+)-Casearborin A)

SMILES for NP0081246 ((+)-Casearborin A)

INCHI for NP0081246 ((+)-Casearborin A)

Structure for NP0081246 ((+)-Casearborin A)

3D Structure for NP0081246 ((+)-Casearborin A)