NP-MRD: Showing NP-Card for Rohituka-14 (NP0077076)

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Record Information

Version

2.0

Created at

2022-04-28 22:14:40 UTC

Updated at

2022-04-28 22:14:40 UTC

NP-MRD ID

NP0077076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rohituka-14

Description

Rohituka 14 belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Rohituka-14 is found in Aphanamixis polystacha and Aphanamixis polystachya. Rohituka-14 was first documented in 2007 (PMID: 17146802). Based on a literature review very few articles have been published on Rohituka 14.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200142D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292200142D          

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   -0.4089    1.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9002    1.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7169   -2.8540    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7117   -3.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745   -3.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3344   -4.7120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3874   -2.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1704   -2.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6595   -1.9689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788   -1.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3926   -1.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4898   -1.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722   -3.9704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468   -2.9641    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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  1  0  0  0
  2 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  2  0  0  0  0
 30 34  1  1  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 34 38  1  0  0  0  0
 21 39  1  1  0  0  0
 20 40  1  6  0  0  0
  1 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0077076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@H]1[C@@H]2O[C@H]3CC(=O)O[C@]4(C)COC(=O)C[C@@H]4[C@@]3(C)[C@@H]2C(=C)[C@@]2(O)C(=O)C[C@@H](C3=COC=C3)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O10/c1-15(2)9-23(34)40-27-26-25(16(3)31(36)20(32)10-18(30(27,31)6)17-7-8-37-13-17)29(5)19-11-22(33)38-14-28(19,4)41-24(35)12-21(29)39-26/h7-8,13,15,18-19,21,25-27,36H,3,9-12,14H2,1-2,4-6H3/t18-,19-,21-,25+,26+,27-,28+,29+,30+,31+/m0/s1

> <INCHI_KEY>
ULYJPGZRBXBUMU-OTLPESSXSA-N

> <FORMULA>
C31H38O10

> <MOLECULAR_WEIGHT>
570.635

> <EXACT_MASS>
570.246497424

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
58.45679188514822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,7R,8R,9R,10R,12S,16S,21R)-7-(furan-3-yl)-4-hydroxy-1,8,16-trimethyl-3-methylidene-5,14,19-trioxo-11,15,18-trioxapentacyclo[10.9.0.0^{2,10}.0^{4,8}.0^{16,21}]henicosan-9-yl 3-methylbutanoate

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.604225066333332

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.906367938517896

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.097997917399756

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8572001347463143

> <JCHEM_POLAR_SURFACE_AREA>
138.57000000000002

> <JCHEM_REFRACTIVITY>
140.87759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,7R,8R,9R,10R,12S,16S,21R)-7-(furan-3-yl)-4-hydroxy-1,8,16-trimethyl-3-methylidene-5,14,19-trioxo-11,15,18-trioxapentacyclo[10.9.0.0^{2,10}.0^{4,8}.0^{16,21}]henicosan-9-yl 3-methylbutanoate

> <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       4.646  -4.016   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.636  -2.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.834  -1.508   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.338  -1.842   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.290  -0.631   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.015  -3.225   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.355  -4.616   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.856  -4.969   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.411  -6.443   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.466  -7.565   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.021  -9.040   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.965  -7.213   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.410  -5.739   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.877  -4.377   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.169  -2.009   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.271  -3.261   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.184  -4.501   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.567  -5.912   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.480  -7.152   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.036  -6.083   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.123  -4.842   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.741  -3.432   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.172  -2.191   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.445  -0.781   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.976  -0.610   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.468   0.459   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.150   1.870   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.763   3.110   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.680   2.041   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.338  -5.328   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.328  -6.868   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.139  -7.334   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.624  -8.796   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.590  -4.430   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.051  -4.915   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.964  -3.675   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.067  -2.424   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.599  -2.890   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.914  -3.705   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.815  -7.411   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.381  -5.533   0.000  0.00  0.00           C+0
CONECT    1    2    8   17   41                                             
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   13   14                                             
CONECT    8    7    1    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7                                                       
CONECT   14    7                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16    1   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   32   40                                             
CONECT   21   20   22   30   39                                             
CONECT   22   21   16   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   21   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   20   33                                                  
CONECT   33   32                                                            
CONECT   34   30   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   34                                                       
CONECT   39   21                                                            
CONECT   40   20                                                            
CONECT   41    1                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₈O₁₀

Average Mass

570.6350 Da

Monoisotopic Mass

570.24650 Da

IUPAC Name

(1R,2R,4S,7R,8R,9R,10R,12S,16S,21R)-7-(furan-3-yl)-4-hydroxy-1,8,16-trimethyl-3-methylidene-5,14,19-trioxo-11,15,18-trioxapentacyclo[10.9.0.0^{2,10}.0^{4,8}.0^{16,21}]henicosan-9-yl 3-methylbutanoate

Traditional Name

(1R,2R,4S,7R,8R,9R,10R,12S,16S,21R)-7-(furan-3-yl)-4-hydroxy-1,8,16-trimethyl-3-methylidene-5,14,19-trioxo-11,15,18-trioxapentacyclo[10.9.0.0^{2,10}.0^{4,8}.0^{16,21}]henicosan-9-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@H]1[C@@H]2O[C@H]3CC(=O)O[C@]4(C)COC(=O)C[C@@H]4[C@@]3(C)[C@@H]2C(=C)[C@@]2(O)C(=O)C[C@@H](C3=COC=C3)[C@]12C

InChI Identifier

InChI=1S/C31H38O10/c1-15(2)9-23(34)40-27-26-25(16(3)31(36)20(32)10-18(30(27,31)6)17-7-8-37-13-17)29(5)19-11-22(33)38-14-28(19,4)41-24(35)12-21(29)39-26/h7-8,13,15,18-19,21,25-27,36H,3,9-12,14H2,1-2,4-6H3/t18-,19-,21-,25+,26+,27-,28+,29+,30+,31+/m0/s1

InChI Key

ULYJPGZRBXBUMU-OTLPESSXSA-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
Aphanamixis polystacha	Plant	KNApSAcK
Aphanamixis polystachya	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Tricarboxylic acid or derivatives
Caprolactone
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
Fatty acyl
Oxane
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Furan
Carboxylic acid ester
Ketone
Lactone
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxide
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen 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	3.01	ALOGPS
logP	2.6	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	138.57 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	140.88 m³·mol⁻¹	ChemAxon
Polarizability	58.46 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

100938103

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang H, Chen F, Wang X, Wu D, Chen Q: Complete assignments of 1H and 13C NMR data for rings A,B-seco limonoids from the seed of Aphanamixis polystachya. Magn Reson Chem. 2007 Feb;45(2):189-92. doi: 10.1002/mrc.1937. [PubMed:17146802 ]

Showing NP-Card for Rohituka-14 (NP0077076)

MOL for NP0077076 (Rohituka-14)

3D MOL for NP0077076 (Rohituka-14)

3D SDF for NP0077076 (Rohituka-14)

3D-SDF for NP0077076 (Rohituka-14)

PDB for NP0077076 (Rohituka-14)

3D PDB for NP0077076 (Rohituka-14)

SMILES for NP0077076 (Rohituka-14)

INCHI for NP0077076 (Rohituka-14)

Structure for NP0077076 (Rohituka-14)

3D Structure for NP0077076 (Rohituka-14)