NP-MRD: Showing NP-Card for (2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione (NP0287560)

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Record Information

Version

2.0

Created at

2022-09-09 16:45:25 UTC

Updated at

2022-09-09 16:45:26 UTC

NP-MRD ID

NP0287560

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

Description

COCHLIOQUINONE C belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. (2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione is found in Bipolaris cynodontis. (2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione was first documented in 2014 (PMID: 25491333). Based on a literature review a small amount of articles have been published on COCHLIOQUINONE C (PMID: 35427653).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092218452D          

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  Mrv1652309092218452D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  1  0  0  0
 31 29  1  1  0  0  0
 16 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 32  1  0  0  0  0
 32 33  1  6  0  0  0
 14 34  1  0  0  0  0
  9 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0287560

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)[C@@H](C)C1=CC(=O)C2=C(O[C@]3(C)CC[C@H]4O[C@H](CC[C@]4(C)[C@H]3[C@@H]2O)C(C)(C)O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O7/c1-8-14(2)21(30)15(3)16-13-17(29)20-23(32)25-27(6)11-9-18(26(4,5)33)34-19(27)10-12-28(25,7)35-24(20)22(16)31/h13-15,18-19,23,25,32-33H,8-12H2,1-7H3/t14-,15-,18+,19+,23+,25+,27-,28+/m0/s1

> <INCHI_KEY>
KELSQTYNZXMABE-NMOAWYSDSA-N

> <FORMULA>
C28H40O7

> <MOLECULAR_WEIGHT>
488.621

> <EXACT_MASS>
488.277403628

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.609031016600284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4aR,4bS,5S,10aR,12aR)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2S,4S)-4-methyl-3-oxohexan-2-yl]-2,3,4,4a,4b,5,6,9,10a,11,12,12a-dodecahydro-1,10-dioxatetraphene-6,9-dione

> <JCHEM_LOGP>
3.478919293999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.463914862930242

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.760528036612527

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0935564768374126

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
132.97279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4aR,4bS,5S,10aR,12aR)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2S,4S)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.945   2.534   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.457   2.243   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.961   0.788   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.953  -0.376   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.473   0.497   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.482   1.661   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.978  -0.958   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.969  -2.122   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.490  -1.249   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.994  -2.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.506  -2.995   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.010  -4.450   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.514  -1.831   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.010  -0.376   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.018   0.788   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.531   0.497   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.027   1.952   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.539   1.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.051   1.370   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.555  -0.085   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.067  -0.376   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.571  -1.831   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.084  -2.122   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.596  -2.413   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.793  -3.634   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      18.375  -0.610   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      15.563  -2.995   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.051  -2.704   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.547  -1.249   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.539  -2.413   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.035  -0.958   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.027  -2.122   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.531  -3.577   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.498  -0.085   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.994   1.370   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   34                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   32                                                  
CONECT   14   13   15   34                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   31                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   22   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   20   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   16   32                                                  
CONECT   32   31   13   33                                                  
CONECT   33   32                                                            
CONECT   34   14    9   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₇

Average Mass

488.6210 Da

Monoisotopic Mass

488.27740 Da

IUPAC Name

(2R,4aR,4bS,5S,10aR,12aR)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2S,4S)-4-methyl-3-oxohexan-2-yl]-2,3,4,4a,4b,5,6,9,10a,11,12,12a-dodecahydro-1,10-dioxatetraphene-6,9-dione

Traditional Name

(2R,4aR,4bS,5S,10aR,12aR)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2S,4S)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)[C@@H](C)C1=CC(=O)C2=C(O[C@]3(C)CC[C@H]4O[C@H](CC[C@]4(C)[C@H]3[C@@H]2O)C(C)(C)O)C1=O

InChI Identifier

InChI=1S/C28H40O7/c1-8-14(2)21(30)15(3)16-13-17(29)20-23(32)25-27(6)11-9-18(26(4,5)33)34-19(27)10-12-28(25,7)35-24(20)22(16)31/h13-15,18-19,23,25,32-33H,8-12H2,1-7H3/t14-,15-,18+,19+,23+,25+,27-,28+/m0/s1

InChI Key

KELSQTYNZXMABE-NMOAWYSDSA-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

Species Name	Source	Reference
Bipolaris cynodontis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Vinylogous ester
Tertiary alcohol
Secondary alcohol
Ketone
Oxacycle
Ether
Dialkyl ether
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	3.48	ChemAxon
pKa (Strongest Acidic)	13.76	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	132.97 m³·mol⁻¹	ChemAxon
Polarizability	54.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00045326

Chemspider ID

24603386

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45934407

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qi QY, Huang L, He LW, Han JJ, Chen Q, Cai L, Liu HW: Cochlioquinone derivatives with apoptosis-inducing effects on HCT116 colon cancer cells from the phytopathogenic fungus Bipolaris luttrellii L439. Chem Biodivers. 2014 Dec;11(12):1892-9. doi: 10.1002/cbdv.201400106. [PubMed:25491333 ]
Feng L, Wang XJ, Li L, Zhang AX, Shang RR, Tan NH, Wang Z: Identification of meroterpenoids from Bipolaris victoriae S27 and their potential activity against tumor metastasis and inhibition of the NF-kappaB signaling pathway. Phytochemistry. 2022 Aug;200:113180. doi: 10.1016/j.phytochem.2022.113180. Epub 2022 Apr 12. [PubMed:35427653 ]
LOTUS database [Link]

Showing NP-Card for (2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione (NP0287560)

MOL for NP0287560 ((2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione)

3D MOL for NP0287560 ((2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione)

3D SDF for NP0287560 ((2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione)

3D-SDF for NP0287560 ((2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione)

PDB for NP0287560 ((2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione)

3D PDB for NP0287560 ((2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione)

SMILES for NP0287560 ((2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione)

INCHI for NP0287560 ((2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione)

Structure for NP0287560 ((2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione)

3D Structure for NP0287560 ((2r,4ar,4bs,5s,10ar,12ar)-5-hydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-8-[(2s,4s)-4-methyl-3-oxohexan-2-yl]-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphene-6,9-dione)