NP-MRD: Showing NP-Card for (1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid (NP0322333)

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Record Information

Version

2.0

Created at

2022-09-12 01:02:46 UTC

Updated at

2022-09-12 01:02:46 UTC

NP-MRD ID

NP0322333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid

Description

Musabalbisiane 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. Musabalbisiane A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Musabalbisiane A has been detected, but not quantified in, fruits. This could make musabalbisiane a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 01291301472D          

 35 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 01291301472D          

 35 38  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0322333

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1C[C@@H](O)[C@]2(C=O)[C@@](CC(O)=O)([C@H](O)CC[C@]2(C=O)[C@@]11C[C@H](O[C@H]1O)C1=COC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O12/c24-8-13-5-16(28)23(11-26)20(10-25,3-1-15(27)22(23,18(31)32)7-17(29)30)21(13)6-14(35-19(21)33)12-2-4-34-9-12/h2,4,9-11,13-16,19,24,27-28,33H,1,3,5-8H2,(H,29,30)(H,31,32)/t13-,14-,15+,16+,19+,20-,21-,22-,23-/m0/s1

> <INCHI_KEY>
OCCSGWHBAQZQOW-ZUKDTQBBSA-N

> <FORMULA>
C23H28O12

> <MOLECULAR_WEIGHT>
496.4612

> <EXACT_MASS>
496.15807636

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
46.592460802522204

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,2'R,4R,4aR,5S,5'S,6R,8aS)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-5-carboxylic acid

> <ALOGPS_LOGP>
-0.95

> <JCHEM_LOGP>
-2.2609832193333332

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.5336057092649105

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7177053089855154

> <JCHEM_PKA_STRONGEST_BASIC>
-2.606934189510979

> <JCHEM_POLAR_SURFACE_AREA>
212.02999999999997

> <JCHEM_REFRACTIVITY>
112.71949999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.88e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,2'R,4R,4aR,5S,5'S,6R,8aS)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JAN-13         0                                  
HETATM    1  C   UNK     0      -9.167 -15.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.500 -16.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.500 -17.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.167 -18.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.833 -17.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.833 -16.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.499 -18.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.166 -17.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.166 -16.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.499 -15.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.745 -14.715   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.269 -13.250   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.729 -13.250   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.254 -14.715   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.499 -20.240   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -7.906 -24.237   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -11.834 -18.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -9.240 -22.293   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.582 -25.022   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -11.353 -23.797   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -11.207 -25.330   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0     -12.754 -23.156   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -10.940 -20.570   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -10.900 -22.110   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -12.294 -19.836   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -9.116 -13.443   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -10.647 -13.270   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.789 -15.191   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.832 -17.160   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.498 -16.390   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -8.175 -12.004   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.945  -9.635   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -10.190 -10.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -9.715 -12.004   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -7.699 -10.540   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   18   23                                             
CONECT    5    4    6    7   16                                             
CONECT    6    1   10    5   26                                             
CONECT    7    5    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   29                                                  
CONECT   10    6    9   11   14                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   10   28                                                  
CONECT   15    7                                                            
CONECT   16    5   19                                                       
CONECT   17    3                                                            
CONECT   18    4   20                                                       
CONECT   19   16                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    4   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    6   27                                                       
CONECT   27   26                                                            
CONECT   28   14                                                            
CONECT   29    9   30                                                       
CONECT   30   29                                                            
CONECT   31   12   34   35                                                  
CONECT   32   33   35                                                       
CONECT   33   32   34                                                       
CONECT   34   31   33                                                       
CONECT   35   31   32                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,2'r,4R,4AR,5S,5's,6R,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-5-carboxylate	Generator

Chemical Formula

C₂₃H₂₈O₁₂

Average Mass

496.4612 Da

Monoisotopic Mass

496.15808 Da

IUPAC Name

(1R,2R,2'R,4R,4aR,5S,5'S,6R,8aS)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-octahydro-2H-spiro[naphthalene-1,3'-oxolane]-5-carboxylic acid

Traditional Name

(1R,2R,2'R,4R,4aR,5S,5'S,6R,8aS)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC[C@@H]1C[C@@H](O)[C@]2(C=O)[C@@](CC(O)=O)([C@H](O)CC[C@]2(C=O)[C@@]11C[C@H](O[C@H]1O)C1=COC=C1)C(O)=O

InChI Identifier

InChI=1S/C23H28O12/c24-8-13-5-16(28)23(11-26)20(10-25,3-1-15(27)22(23,18(31)32)7-17(29)30)21(13)6-14(35-19(21)33)12-2-4-34-9-12/h2,4,9-11,13-16,19,24,27-28,33H,1,3,5-8H2,(H,29,30)(H,31,32)/t13-,14-,15+,16+,19+,20-,21-,22-,23-/m0/s1

InChI Key

OCCSGWHBAQZQOW-ZUKDTQBBSA-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

Not Available

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
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Cyclic alcohol
Heteroaromatic compound
Furan
Tetrahydrofuran
Hemiacetal
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Aldehyde
Alcohol
Organic oxygen compound
Primary alcohol
Organooxygen compound
Carbonyl group
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	-0.95	ALOGPS
logP	-2.3	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	212.03 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.72 m³·mol⁻¹	ChemAxon
Polarizability	46.59 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

HMDB0038680

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018084

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

131752422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid (NP0322333)

MOL for NP0322333 ((1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid)

3D MOL for NP0322333 ((1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid)

3D SDF for NP0322333 ((1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid)

3D-SDF for NP0322333 ((1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid)

PDB for NP0322333 ((1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid)

3D PDB for NP0322333 ((1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid)

SMILES for NP0322333 ((1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid)

INCHI for NP0322333 ((1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid)

Structure for NP0322333 ((1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid)

3D Structure for NP0322333 ((1r,2r,2'r,4r,4ar,5s,5's,6r,8as)-5-(carboxymethyl)-4a,8a-diformyl-5'-(furan-3-yl)-2',4,6-trihydroxy-2-(hydroxymethyl)-hexahydrospiro[naphthalene-1,3'-oxolane]-5-carboxylic acid)