NP-MRD: Showing NP-Card for methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate (NP0166220)

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Record Information

Version

2.0

Created at

2022-09-03 01:33:24 UTC

Updated at

2022-09-03 01:33:24 UTC

NP-MRD ID

NP0166220

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate

Description

Sequoiatone B belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate was first documented in 2008 (PMID: 18067932). Based on a literature review very few articles have been published on Sequoiatone B (PMID: 28303222).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032203332D          

 27 28  0  0  1  0            999 V2000
    0.9920   -7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209   -7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499   -7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2788   -7.4340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2788   -8.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9933   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9933   -6.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7078   -7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4222   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5085   -6.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8954   -5.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1108   -5.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0669   -4.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4538   -4.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3155   -6.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7280   -5.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5530   -5.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9655   -4.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9655   -6.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5530   -6.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7280   -6.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1759   -7.3570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7215   -7.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -8.1443    0.0000 O   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
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
M  END

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
    3.7381   -0.7224    6.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7175   -0.4561    4.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154    0.4243    4.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3981    0.7526    2.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2249    1.5958    2.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    1.0460    2.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456   -0.1611    2.2099 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2487   -1.3961    2.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    0.1288    0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812    1.3074    0.4121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421   -0.9690   -0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3139   -0.9342   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1400    0.2759   -2.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719    1.2484   -2.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142    2.3097   -2.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0941    1.2457   -1.3931 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0380    2.2896   -1.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0331    0.2412   -3.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3948    1.1474   -4.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723    0.7645   -5.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5694    1.6499   -6.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836   -0.5462   -5.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826   -1.4551   -4.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995   -1.1142   -3.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9090   -1.9534   -2.2890 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8440   -2.7520   -2.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372   -2.7518   -1.6176 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6798   -0.7832    6.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2949   -1.6604    6.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2651    0.1591    6.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527   -1.4121    4.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6523   -0.0285    4.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5828    0.0732    4.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517    1.3933    5.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5269   -0.1732    2.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111    1.3732    2.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3244    2.5320    3.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3437    1.9603    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012    1.8425    2.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733    0.8541    4.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -0.4008    2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128   -1.6122    1.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4649   -2.2874    2.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7289   -1.4796    3.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2941   -1.9782    0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323    1.8040   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    2.8198   -0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    2.9894   -2.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0124    2.1690   -4.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6648    1.9014   -7.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2852    1.1691   -7.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0181    2.6002   -6.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7761   -2.4874   -4.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822   -2.5219   -2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0367   -3.8499   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912   -2.4760   -4.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5979   -3.7053   -1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 13 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  1  1
 25 12  1  0
 24 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  1
  8 42  1  0
  8 43  1  0
  8 44  1  0
 11 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  0
M  END


  Mrv1652309032203332D          

 27 28  0  0  1  0            999 V2000
    0.9920   -7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209   -7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499   -7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2788   -7.4340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2788   -8.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9933   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9933   -6.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7078   -7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4222   -7.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5085   -6.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8954   -5.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1108   -5.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0669   -4.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4538   -4.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3155   -6.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7280   -5.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5530   -5.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9655   -4.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9655   -6.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5530   -6.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7280   -6.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1759   -7.3570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7215   -7.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -8.1443    0.0000 O   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
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0166220

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC[C@H](C)C(=O)\C=C1/C(C(=O)OC)=C2C=C(C)OC=C2[C@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-6-7-8-9-10-14(2)19(23)12-17-20(21(24)26-5)16-11-15(3)27-13-18(16)22(17,4)25/h11-14,25H,6-10H2,1-5H3/b17-12+/t14-,22+/m0/s1

> <INCHI_KEY>
AZRKTTNHSKOLMR-JVEVTSHPSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.42300486224258

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (6E,7R)-7-hydroxy-3,7-dimethyl-6-[(3S)-3-methyl-2-oxononylidene]-6H,7H-cyclopenta[c]pyran-5-carboxylate

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
3.3583136379999994

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.538116265053873

> <JCHEM_PKA_STRONGEST_BASIC>
-3.438227945665435

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
107.80639999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (6E,7R)-7-hydroxy-3,7-dimethyl-6-[(3S)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.852 -13.877   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.185 -13.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.519 -13.877   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.853 -13.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.186 -13.877   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.520 -13.107   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.854 -13.877   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.854 -15.417   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.188 -13.107   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.188 -11.567   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.521 -13.877   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.855 -13.107   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.016 -11.575   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.871 -10.545   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.407 -11.021   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      13.192  -9.038   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.047  -8.008   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.522 -11.255   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.292  -9.921   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.832  -9.921   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.602  -8.588   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.602 -11.255   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      17.832 -12.589   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.292 -12.589   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.262 -13.733   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.280 -14.888   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.801 -15.203   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25                                                  
CONECT   25   24   12   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

methyl (6E,7R)-7-hydroxy-3,7-dimethyl-6-[(3S)-3-methyl-2-oxononylidene]-6H,7H-cyclopenta[c]pyran-5-carboxylate

Traditional Name

methyl (6E,7R)-7-hydroxy-3,7-dimethyl-6-[(3S)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCCC[C@H](C)C(=O)\C=C1/C(C(=O)OC)=C2C=C(C)OC=C2[C@]1(C)O

InChI Identifier

InChI=1S/C22H30O5/c1-6-7-8-9-10-14(2)19(23)12-17-20(21(24)26-5)16-11-15(3)27-13-18(16)22(17,4)25/h11-14,25H,6-10H2,1-5H3/b17-12+/t14-,22+/m0/s1

InChI Key

AZRKTTNHSKOLMR-JVEVTSHPSA-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 pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Not Available

Direct Parent

Pyrans

Alternative Parents

Substituents

Pyran
Acryloyl-group
Enone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
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	4.29	ALOGPS
logP	3.36	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.54	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	107.81 m³·mol⁻¹	ChemAxon
Polarizability	42.42 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00034236

Chemspider ID

24687509

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15382209

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin Z, Zhu T, Fang Y, Gu Q, Zhu W: Polyketides from Penicillium sp. JP-1, an endophytic fungus associated with the mangrove plant Aegiceras corniculatum. Phytochemistry. 2008 Mar;69(5):1273-8. doi: 10.1016/j.phytochem.2007.10.030. Epub 2007 Dec 11. [PubMed:18067932 ]
Sun T, Zou J, Chen G, Hu D, Wu B, Liu X, Yao X, Gao H: A set of interesting sequoiatones stereoisomers from a wetland soil-derived fungus Talaromyces flavus. Acta Pharm Sin B. 2017 Mar;7(2):167-172. doi: 10.1016/j.apsb.2016.07.005. Epub 2016 Aug 10. [PubMed:28303222 ]
LOTUS database [Link]

Showing NP-Card for methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate (NP0166220)

MOL for NP0166220 (methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate)

3D MOL for NP0166220 (methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate)

3D SDF for NP0166220 (methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate)

3D-SDF for NP0166220 (methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate)

PDB for NP0166220 (methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate)

3D PDB for NP0166220 (methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate)

SMILES for NP0166220 (methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate)

INCHI for NP0166220 (methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate)

Structure for NP0166220 (methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate)

3D Structure for NP0166220 (methyl (6e,7r)-7-hydroxy-3,7-dimethyl-6-[(3s)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate)