NP-MRD: Showing NP-Card for Theissenolactone C (NP0010527)

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Record Information

Version

2.0

Created at

2021-01-05 20:00:59 UTC

Updated at

2021-07-15 17:06:20 UTC

NP-MRD ID

NP0010527

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Theissenolactone C

Provided By

NPAtlas

Description

Theissenolactone C belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Theissenolactone C is found in Theissenia cinerea. Theissenolactone C was first documented in 2018 (PMID: 29686615). Based on a literature review a small amount of articles have been published on Theissenolactone C (PMID: 34185528) (PMID: 30668341).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107383D          

 29 30  0  0  0  0            999 V2000
    4.1972   -1.3117   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279   -0.7609   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1124   -0.1501    0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.4051    0.3429 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1144   -0.5526   -0.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -0.1686    0.1972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6284    1.1900   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6481    2.0039   -0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    1.5952   -0.5731 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4233    2.6739    0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822    1.2910   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7309    2.3616   -0.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5880   -0.0170   -0.3073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996   -0.9508   -0.3736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8985   -2.1490    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4744   -2.0014   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9216   -0.5117    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530   -1.9227    0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -0.8540   -1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -0.0885    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    0.7537    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056   -0.1464    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    2.9805   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323    1.3746   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0161    3.5424   -0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.2828   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680   -2.7750   -0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5074   -1.8190    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0128   -2.7096    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9  4  1  0  0  0  0
 14  6  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 20  1  0  0  0  0
  4 21  1  1  0  0  0
  6 22  1  1  0  0  0
  8 23  1  0  0  0  0
  9 24  1  6  0  0  0
 10 25  1  0  0  0  0
 14 26  1  6  0  0  0
 15 27  1  0  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
M  END

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    4.1972   -1.3117   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279   -0.7609   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1124   -0.1501    0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.4051    0.3429 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1144   -0.5526   -0.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -0.1686    0.1972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6284    1.1900   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6481    2.0039   -0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    1.5952   -0.5731 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4233    2.6739    0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822    1.2910   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7309    2.3616   -0.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5880   -0.0170   -0.3073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996   -0.9508   -0.3736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8985   -2.1490    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4744   -2.0014   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9216   -0.5117    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530   -1.9227    0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -0.8540   -1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -0.0885    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    0.7537    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056   -0.1464    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    2.9805   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323    1.3746   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0161    3.5424   -0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.2828   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680   -2.7750   -0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5074   -1.8190    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0128   -2.7096    0.8120 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  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  9  4  1  0
 14  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  1
  6 22  1  1
  8 23  1  0
  9 24  1  6
 10 25  1  0
 14 26  1  6
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END


  Mrv1652306242107383D          

 29 30  0  0  0  0            999 V2000
    4.1972   -1.3117   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279   -0.7609   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1124   -0.1501    0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.4051    0.3429 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1144   -0.5526   -0.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -0.1686    0.1972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6284    1.1900   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6481    2.0039   -0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    1.5952   -0.5731 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4233    2.6739    0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822    1.2910   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7309    2.3616   -0.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5880   -0.0170   -0.3073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996   -0.9508   -0.3736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8985   -2.1490    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4744   -2.0014   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9216   -0.5117    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530   -1.9227    0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -0.8540   -1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -0.0885    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    0.7537    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056   -0.1464    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    2.9805   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323    1.3746   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0161    3.5424   -0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.2828   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680   -2.7750   -0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5074   -1.8190    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0128   -2.7096    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9  4  1  0  0  0  0
 14  6  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 20  1  0  0  0  0
  4 21  1  1  0  0  0
  6 22  1  1  0  0  0
  8 23  1  0  0  0  0
  9 24  1  6  0  0  0
 10 25  1  0  0  0  0
 14 26  1  6  0  0  0
 15 27  1  0  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010527

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])=C2C(=O)O[C@]([H])(C([H])([H])[H])[C@@]2([H])O[C@@]1([H])C(\[H])=C(/[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O4/c1-3-4-9-8(12)5-7-10(15-9)6(2)14-11(7)13/h3-6,8-10,12H,1-2H3/b4-3+/t6-,8-,9+,10-/m1/s1

> <INCHI_KEY>
UNUOWDGIBRAPFZ-GDQWMFRCSA-N

> <FORMULA>
C11H14O4

> <MOLECULAR_WEIGHT>
210.229

> <EXACT_MASS>
210.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.8048421246259

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,7R,7aS)-3-hydroxy-7-methyl-2-[(1E)-prop-1-en-1-yl]-2H,3H,5H,7H,7aH-furo[3,4-b]pyran-5-one

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
1.1466555223333332

> <ALOGPS_LOGS>
-0.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.67722868924691

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3773801713234004

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
54.71930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,7R,7aS)-3-hydroxy-7-methyl-2-[(1E)-prop-1-en-1-yl]-2H,3H,7H,7aH-furo[3,4-b]pyran-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    4.1972   -1.3117   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279   -0.7609   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1124   -0.1501    0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.4051    0.3429 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1144   -0.5526   -0.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -0.1686    0.1972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6284    1.1900   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6481    2.0039   -0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    1.5952   -0.5731 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4233    2.6739    0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822    1.2910   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7309    2.3616   -0.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5880   -0.0170   -0.3073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996   -0.9508   -0.3736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8985   -2.1490    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4744   -2.0014   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9216   -0.5117    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530   -1.9227    0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -0.8540   -1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -0.0885    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    0.7537    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056   -0.1464    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    2.9805   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323    1.3746   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0161    3.5424   -0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.2828   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680   -2.7750   -0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5074   -1.8190    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0128   -2.7096    0.8120 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  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  9  4  1  0
 14  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  1
  6 22  1  1
  8 23  1  0
  9 24  1  6
 10 25  1  0
 14 26  1  6
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.197  -1.312  -0.034  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.828  -0.761  -0.351  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.112  -0.150   0.589  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.778   0.405   0.343  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.114  -0.553  -0.194  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.372  -0.169   0.197  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.628   1.190  -0.396  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.648   2.004  -0.751  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.772   1.595  -0.573  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.423   2.674   0.049  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.082   1.291  -0.441  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.731   2.362  -0.575  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.588  -0.017  -0.307  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.500  -0.951  -0.374  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.898  -2.149   0.448  0.00  0.00           C+0
HETATM   16  H   UNK     0       4.474  -2.001  -0.852  0.00  0.00           H+0
HETATM   17  H   UNK     0       4.922  -0.512   0.152  0.00  0.00           H+0
HETATM   18  H   UNK     0       4.153  -1.923   0.899  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.412  -0.854  -1.338  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.594  -0.089   1.575  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.357   0.754   1.322  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.406  -0.146   1.293  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.897   2.981  -1.177  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.232   1.375  -1.560  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.016   3.542  -0.209  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.317  -1.283  -1.415  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.568  -2.775  -0.184  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.507  -1.819   1.312  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.013  -2.710   0.812  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    1    3   19                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5    9   21                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   14   22                                             
CONECT    7    6    8   11                                                  
CONECT    8    7    9   23                                                  
CONECT    9    8   10    4   24                                             
CONECT   10    9   25                                                       
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15    6   26                                             
CONECT   15   14   27   28   29                                             
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    3                                                            
CONECT   21    4                                                            
CONECT   22    6                                                            
CONECT   23    8                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
CONECT   28   15                                                            
CONECT   29   15                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

RDKit          3D

29 30  0  0  0  0  0  0  0  0999 V2000
    4.1972   -1.3117   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8279   -0.7609   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1124   -0.1501    0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.4051    0.3429 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1144   -0.5526   -0.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3723   -0.1686    0.1972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6284    1.1900   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6481    2.0039   -0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    1.5952   -0.5731 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4233    2.6739    0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822    1.2910   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7309    2.3616   -0.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5880   -0.0170   -0.3073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996   -0.9508   -0.3736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8985   -2.1490    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4744   -2.0014   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9216   -0.5117    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530   -1.9227    0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -0.8540   -1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -0.0885    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    0.7537    1.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056   -0.1464    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    2.9805   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323    1.3746   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0161    3.5424   -0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -1.2828   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5680   -2.7750   -0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5074   -1.8190    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0128   -2.7096    0.8120 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  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  9  4  1  0
 14  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  1
  6 22  1  1
  8 23  1  0
  9 24  1  6
 10 25  1  0
 14 26  1  6
 15 27  1  0
 15 28  1  0
 15 29  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Theissenolactone b	MeSH
2,3,7,7a-Tetrahydro-3-hydroxy-7-methyl-2-(prop-1-en-1-yl)-5H-furo(3,4-b)pyran-5-one	MeSH

Chemical Formula

C₁₁H₁₄O₄

Average Mass

210.2290 Da

Monoisotopic Mass

210.08921 Da

IUPAC Name

(2S,3R,7R,7aS)-3-hydroxy-7-methyl-2-[(1E)-prop-1-en-1-yl]-2H,3H,5H,7H,7aH-furo[3,4-b]pyran-5-one

Traditional Name

(2S,3R,7R,7aS)-3-hydroxy-7-methyl-2-[(1E)-prop-1-en-1-yl]-2H,3H,7H,7aH-furo[3,4-b]pyran-5-one

CAS Registry Number

Not Available

SMILES

C\C=C\[C@@H]1O[C@@H]2[C@@H](C)OC(=O)C2=C[C@H]1O

InChI Identifier

InChI=1S/C11H14O4/c1-3-4-9-8(12)5-7-10(15-9)6(2)14-11(7)13/h3-6,8-10,12H,1-2H3/b4-3+/t6-,8-,9+,10-/m1/s1

InChI Key

UNUOWDGIBRAPFZ-GDQWMFRCSA-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
Theissenia cinerea	NPAtlas	22162166

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Gamma butyrolactone
Pyran
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen 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	0.74	ALOGPS
logP	1.15	ChemAxon
logS	-0.61	ALOGPS
pKa (Strongest Acidic)	13.68	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	54.72 m³·mol⁻¹	ChemAxon
Polarizability	21.8 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

NPAtlas ID

NPA002261

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78440775

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56593440

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hsieh MH, Hsiao G, Chang CH, Yang YL, Ju YM, Kuo YH, Lee TH: Polyketides with Anti-neuroinflammatory Activity from Theissenia cinerea. J Nat Prod. 2021 Jul 23;84(7):1898-1903. doi: 10.1021/acs.jnatprod.0c01307. Epub 2021 Jun 29. [PubMed:34185528 ]
Lin FL, Cheng YW, Yu M, Ho JD, Kuo YC, Chiou GCY, Chang HM, Lee TH, Hsiao G: The fungus-derived retinoprotectant theissenolactone C improves glaucoma-like injury mediated by MMP-9 inhibition. Phytomedicine. 2019 Mar 15;56:207-214. doi: 10.1016/j.phymed.2018.11.002. Epub 2018 Nov 7. [PubMed:30668341 ]
Lin FL, Ho JD, Cheng YW, Chiou GCY, Yen JL, Chang HM, Lee TH, Hsiao G: Theissenolactone C Exhibited Ocular Protection of Endotoxin-Induced Uveitis by Attenuating Ocular Inflammatory Responses and Glial Activation. Front Pharmacol. 2018 Apr 9;9:326. doi: 10.3389/fphar.2018.00326. eCollection 2018. [PubMed:29686615 ]

Showing NP-Card for Theissenolactone C (NP0010527)

MOL for NP0010527 (Theissenolactone C)

3D MOL for NP0010527 (Theissenolactone C)

3D SDF for NP0010527 (Theissenolactone C)

3D-SDF for NP0010527 (Theissenolactone C)

PDB for NP0010527 (Theissenolactone C)

3D PDB for NP0010527 (Theissenolactone C)

SMILES for NP0010527 (Theissenolactone C)

INCHI for NP0010527 (Theissenolactone C)

Structure for NP0010527 (Theissenolactone C)

3D Structure for NP0010527 (Theissenolactone C)