NP-MRD: Showing NP-Card for 6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one (NP0215743)

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Record Information

Version

2.0

Created at

2022-09-05 15:27:39 UTC

Updated at

2022-09-05 15:27:39 UTC

NP-MRD ID

NP0215743

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one

Description

3-Ketoapotrichothecene belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. 6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one is found in Fusarium sambucinum. 3-Ketoapotrichothecene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    4.2528   -0.8564    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7943   -0.5957    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0088   -1.0410    0.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -0.7594    0.8939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0786   -1.4976   -0.0791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084   -0.8721   -0.2820 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8023   -1.1303   -1.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9556   -0.6964   -2.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -1.5027    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1407   -0.2851    1.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3374   -0.1323    1.0342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474    0.7008    1.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1870    0.5608    0.1191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6980    1.5627   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815    0.6709    0.4305 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5664    1.5560    1.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1358    1.1174   -0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205    0.1553   -1.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5902   -0.6334    1.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4875   -1.9342   -0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8030   -0.2439   -0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4061   -1.6038    1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1187   -0.8816    1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8579   -2.2553   -1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8496   -0.7904   -1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058   -1.1059   -3.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464   -2.2626    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685   -1.8548    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5786    0.3208    2.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875    1.7149    1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4558    1.4155   -1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3611    2.5896   -0.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8259    1.5868   -0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3715    1.0557    2.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654    2.5270    1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6655    1.7571    1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6600    2.0911   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528    1.3467   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303    0.7222   -1.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8024   -0.5166   -1.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18  2  1  0
 15  4  1  0
 13  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  1
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END


  Mrv0541 05061309112D          

 18 20  0  0  0  0            999 V2000
    1.0991   -0.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5060   -1.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4064   -1.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -1.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454   -1.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9920   -1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4295    0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750    0.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026   -0.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689   -0.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -0.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343   -0.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6046    0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6852    1.0745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4483   -0.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9469    0.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 10  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13  2  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215743

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2OC3(CO)CC(=O)CC3(C)C2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-10-4-5-13(2)12(6-10)18-15(9-16)8-11(17)7-14(13,15)3/h6,12,16H,4-5,7-9H2,1-3H3

> <INCHI_KEY>
JJBMWLFFOIHRLZ-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.390867048852712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
1.659309464666666

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.55098848813364

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.317058821095365

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0915117713747575

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
69.089

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.052  -0.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.545  -2.748   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.225  -2.734   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.998  -1.938   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.498  -2.288   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.604   0.659   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.318  -2.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.135   0.230   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.100   1.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.552  -0.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.582  -1.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.104   0.309   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.551  -1.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.091  -1.194   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.595   0.260   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.612   2.006   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.037  -1.748   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.368   1.190   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    5   10                                                       
CONECT    5    4   13                                                       
CONECT    6   10   12                                                       
CONECT    7   11   14                                                       
CONECT    8   11   15                                                       
CONECT    9   15   16                                                       
CONECT   10    1    4    6                                                  
CONECT   11    7    8   17                                                  
CONECT   12    6   13   18                                                  
CONECT   13    2    5   12   14                                             
CONECT   14    3    7   13   15                                             
CONECT   15    8    9   14   18                                             
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3334 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one

Traditional Name

6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one

CAS Registry Number

Not Available

SMILES

CC1=CC2OC3(CO)CC(=O)CC3(C)C2(C)CC1

InChI Identifier

InChI=1S/C15H22O3/c1-10-4-5-13(2)12(6-10)18-15(9-16)8-11(17)7-14(13,15)3/h6,12,16H,4-5,7-9H2,1-3H3

InChI Key

JJBMWLFFOIHRLZ-UHFFFAOYSA-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
Fusarium sambucinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Not Available

Substituents

Not Available

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	1.35	ALOGPS
logP	1.66	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	14.32	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.09 m³·mol⁻¹	ChemAxon
Polarizability	27.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036550

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015453

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

14408092

PDB ID

Not Available

ChEBI ID

143041

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one (NP0215743)

MOL for NP0215743 (6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one)

3D MOL for NP0215743 (6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one)

3D SDF for NP0215743 (6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one)

3D-SDF for NP0215743 (6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one)

PDB for NP0215743 (6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one)

3D PDB for NP0215743 (6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one)

SMILES for NP0215743 (6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one)

INCHI for NP0215743 (6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one)

Structure for NP0215743 (6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one)

3D Structure for NP0215743 (6-(hydroxymethyl)-1,2,10-trimethyl-7-oxatricyclo[6.4.0.0²,⁶]dodec-9-en-4-one)