NP-MRD: Showing NP-Card for (+)-Casearborin B (NP0081247)

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Record Information

Version

1.0

Created at

2022-04-29 02:12:33 UTC

Updated at

2022-04-29 02:12:33 UTC

NP-MRD ID

NP0081247

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Casearborin B

Description

Casearborin B 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 B is found in Casearia arborea. Based on a literature review very few articles have been published on Casearborin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204122D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292204122D          

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   -2.0292    0.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9549    1.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8577    1.4011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    2.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084    2.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731    2.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3860   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603   -3.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8844   -3.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3307   -3.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 23 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  3 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 36 39  1  0  0  0  0
  3 40  1  1  0  0  0
  2 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C(=O)O[C@@H]1C[C@@H]2[C@]3(CC[C@@H](C)[C@@]2(C)C\C=C(/C)C=C)[C@H](OC(C)=O)O[C@H](OC(C)=O)C3=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O9/c1-8-18(2)11-13-31(6)19(3)12-14-32-24(29(38-20(4)33)41-30(32)39-21(5)34)16-23(17-27(31)32)40-28(36)22-9-10-25(35)26(15-22)37-7/h8-11,15-16,19,23,27,29-30,35H,1,12-14,17H2,2-7H3/b18-11+/t19-,23+,27+,29+,30-,31-,32-/m1/s1

> <INCHI_KEY>
HSCLLTPGIBCIBD-DZHOVOBOSA-N

> <FORMULA>
C32H40O9

> <MOLECULAR_WEIGHT>
568.663

> <EXACT_MASS>
568.267232868

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
60.92945245488353

> <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-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
5.09

> <JCHEM_LOGP>
5.6353763369999985

> <ALOGPS_LOGS>
-5.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.987182016618634

> <JCHEM_PKA_STRONGEST_BASIC>
-4.388920485577064

> <JCHEM_POLAR_SURFACE_AREA>
117.59000000000003

> <JCHEM_REFRACTIVITY>
151.57940000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.49e-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-hydroxy-3-methoxybenzoate

> <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  O   UNK     0      12.028  -2.458   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.351  -3.245   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.422   1.485   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.893   1.666   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.248   0.267   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.262  -0.033   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.277   1.125   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.788   0.824   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.782   2.583   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.468   2.615   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.011   4.086   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.509   4.426   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.056   5.217   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.720  -4.440   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.113  -5.735   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.651  -5.661   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.484  -6.956   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.779  -8.325   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.356  -4.292   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.725  -4.421   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.652  -3.036   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   41                                                  
CONECT    3    2    4   34   40                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   25                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   23                                                  
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   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21   16   22                                                       
CONECT   22   21                                                            
CONECT   23    7   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24    5   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    3   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36                                                            
CONECT   40    3                                                            
CONECT   41    2                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₀O₉

Average Mass

568.6630 Da

Monoisotopic Mass

568.26723 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-hydroxy-3-methoxybenzoate

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-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C(=O)O[C@@H]1C[C@@H]2[C@]3(CC[C@@H](C)[C@@]2(C)C\C=C(/C)C=C)[C@H](OC(C)=O)O[C@H](OC(C)=O)C3=C1

InChI Identifier

InChI=1S/C32H40O9/c1-8-18(2)11-13-31(6)19(3)12-14-32-24(29(38-20(4)33)41-30(32)39-21(5)34)16-23(17-27(31)32)40-28(36)22-9-10-25(35)26(15-22)37-7/h8-11,15-16,19,23,27,29-30,35H,1,12-14,17H2,2-7H3/b18-11+/t19-,23+,27+,29+,30-,31-,32-/m1/s1

InChI Key

HSCLLTPGIBCIBD-DZHOVOBOSA-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
M-methoxybenzoic acid or derivatives
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Methoxyphenol
Benzoate ester
Tricarboxylic acid or derivatives
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Phenol ether
Anisole
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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	5.09	ALOGPS
logP	5.64	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	117.59 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	151.58 m³·mol⁻¹	ChemAxon
Polarizability	60.93 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

C00047021

Chemspider ID

4509052

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352095

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Casearborin B (NP0081247)

MOL for NP0081247 ((+)-Casearborin B)

3D MOL for NP0081247 ((+)-Casearborin B)

3D SDF for NP0081247 ((+)-Casearborin B)

3D-SDF for NP0081247 ((+)-Casearborin B)

PDB for NP0081247 ((+)-Casearborin B)

3D PDB for NP0081247 ((+)-Casearborin B)

SMILES for NP0081247 ((+)-Casearborin B)

INCHI for NP0081247 ((+)-Casearborin B)

Structure for NP0081247 ((+)-Casearborin B)

3D Structure for NP0081247 ((+)-Casearborin B)