NP-MRD: Showing NP-Card for tarennin (NP0040757)

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Record Information

Version

2.0

Created at

2021-06-20 22:49:58 UTC

Updated at

2021-06-30 00:14:51 UTC

NP-MRD ID

NP0040757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tarennin

Provided By

JEOL Database JEOL Logo

Description

(1R,4aS,7aS)-1-ethoxy-1H,4aH,5H,7aH-cyclopenta[c]pyran-4,7-dicarboxylic acid belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. tarennin is found in Tarenna attenuata. tarennin was first documented in 2006 (Yang, X.-W., et al.). Based on a literature review very few articles have been published on (1R,4aS,7aS)-1-ethoxy-1H,4aH,5H,7aH-cyclopenta[c]pyran-4,7-dicarboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100493D          

 32 33  0  0  0  0            999 V2000
   -2.8118   -0.7964    1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392   -0.7122    0.4870 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5808    0.5448    0.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0118    0.7158   -0.9629 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0622   -0.2093   -1.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117    0.0700   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5331    1.2623    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477    1.4277    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543    2.4428    1.4399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317    0.3384    0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649    2.4821   -0.1978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4112    3.6059   -0.9515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9599    3.4380   -2.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223    2.6519   -2.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    2.3329   -3.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9283    1.7620   -3.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203    2.7422   -4.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728    2.1834   -1.0871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0167   -0.7030    2.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5153    0.0234    2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.7469    2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475   -0.7910   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -1.5309    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7961    0.4924   -1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283   -0.8186   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756    0.6074    1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370    2.8403    0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    3.5324   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1087    4.5929   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4385    3.9275   -3.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8119    2.4645   -5.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008    2.8309   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0  0  0  0
 14 15  1  0  0  0  0
 18 11  1  0  0  0  0
 15 17  1  0  0  0  0
 15 16  2  0  0  0  0
 11  7  1  0  0  0  0
  7  8  1  0  0  0  0
 18  4  1  0  0  0  0
  8 10  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  4  3  1  0  0  0  0
 11 12  1  0  0  0  0
  3  2  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  1  0  0  0  0
 13 14  2  0  0  0  0
 11 27  1  1  0  0  0
 14 18  1  0  0  0  0
 18 32  1  1  0  0  0
  4 24  1  6  0  0  0
  6 25  1  0  0  0  0
 12 28  1  0  0  0  0
 12 29  1  0  0  0  0
 13 30  1  0  0  0  0
 17 31  1  0  0  0  0
 10 26  1  0  0  0  0
  2 22  1  0  0  0  0
  2 23  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -2.8118   -0.7964    1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392   -0.7122    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5808    0.5448    0.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0118    0.7158   -0.9629 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0622   -0.2093   -1.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117    0.0700   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5331    1.2623    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477    1.4277    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543    2.4428    1.4399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317    0.3384    0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649    2.4821   -0.1978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4112    3.6059   -0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    3.4380   -2.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223    2.6519   -2.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    2.3329   -3.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9283    1.7620   -3.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203    2.7422   -4.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728    2.1834   -1.0871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0167   -0.7030    2.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5153    0.0234    2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.7469    2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475   -0.7910   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -1.5309    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7961    0.4924   -1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283   -0.8186   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756    0.6074    1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370    2.8403    0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    3.5324   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1087    4.5929   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4385    3.9275   -3.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8119    2.4645   -5.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008    2.8309   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
 14 15  1  0
 18 11  1  0
 15 17  1  0
 15 16  2  0
 11  7  1  0
  7  8  1  0
 18  4  1  0
  8 10  1  0
  4  5  1  0
  8  9  2  0
  5  6  1  0
  4  3  1  0
 11 12  1  0
  3  2  1  0
 12 13  1  0
  2  1  1  0
 13 14  2  0
 11 27  1  1
 14 18  1  0
 18 32  1  1
  4 24  1  6
  6 25  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 17 31  1  0
 10 26  1  0
  2 22  1  0
  2 23  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652306212100493D          

 32 33  0  0  0  0            999 V2000
   -2.8118   -0.7964    1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392   -0.7122    0.4870 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5808    0.5448    0.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0118    0.7158   -0.9629 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0622   -0.2093   -1.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117    0.0700   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5331    1.2623    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477    1.4277    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543    2.4428    1.4399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317    0.3384    0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649    2.4821   -0.1978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4112    3.6059   -0.9515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9599    3.4380   -2.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223    2.6519   -2.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    2.3329   -3.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9283    1.7620   -3.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203    2.7422   -4.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728    2.1834   -1.0871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0167   -0.7030    2.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5153    0.0234    2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.7469    2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475   -0.7910   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -1.5309    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7961    0.4924   -1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283   -0.8186   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756    0.6074    1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370    2.8403    0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    3.5324   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1087    4.5929   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4385    3.9275   -3.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8119    2.4645   -5.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008    2.8309   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0  0  0  0
 14 15  1  0  0  0  0
 18 11  1  0  0  0  0
 15 17  1  0  0  0  0
 15 16  2  0  0  0  0
 11  7  1  0  0  0  0
  7  8  1  0  0  0  0
 18  4  1  0  0  0  0
  8 10  1  0  0  0  0
  4  5  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  4  3  1  0  0  0  0
 11 12  1  0  0  0  0
  3  2  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  1  0  0  0  0
 13 14  2  0  0  0  0
 11 27  1  1  0  0  0
 14 18  1  0  0  0  0
 18 32  1  1  0  0  0
  4 24  1  6  0  0  0
  6 25  1  0  0  0  0
 12 28  1  0  0  0  0
 12 29  1  0  0  0  0
 13 30  1  0  0  0  0
 17 31  1  0  0  0  0
 10 26  1  0  0  0  0
  2 22  1  0  0  0  0
  2 23  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040757

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])([H])[C@]2([H])C(=C([H])O[C@@]([H])(OC([H])([H])C([H])([H])[H])[C@]12[H])C(=O)O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O6/c1-2-17-12-9-6(3-4-7(9)10(13)14)8(5-18-12)11(15)16/h4-6,9,12H,2-3H2,1H3,(H,13,14)(H,15,16)/t6-,9+,12-/m1/s1

> <INCHI_KEY>
WWRWHCABBGNGCZ-PUQNFTFYSA-N

> <FORMULA>
C12H14O6

> <MOLECULAR_WEIGHT>
254.238

> <EXACT_MASS>
254.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.532446819244505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4aS,7aS)-1-ethoxy-1H,4aH,5H,7aH-cyclopenta[c]pyran-4,7-dicarboxylic acid

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
0.6492751650000005

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.706419436534397

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.955908982199462

> <JCHEM_PKA_STRONGEST_BASIC>
-4.226622489240684

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
60.76650000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aS,7aS)-1-ethoxy-1H,4aH,5H,7aH-cyclopenta[c]pyran-4,7-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -2.8118   -0.7964    1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392   -0.7122    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5808    0.5448    0.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0118    0.7158   -0.9629 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0622   -0.2093   -1.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117    0.0700   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5331    1.2623    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477    1.4277    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543    2.4428    1.4399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317    0.3384    0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649    2.4821   -0.1978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4112    3.6059   -0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    3.4380   -2.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223    2.6519   -2.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    2.3329   -3.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9283    1.7620   -3.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203    2.7422   -4.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728    2.1834   -1.0871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0167   -0.7030    2.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5153    0.0234    2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.7469    2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475   -0.7910   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -1.5309    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7961    0.4924   -1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283   -0.8186   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756    0.6074    1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370    2.8403    0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    3.5324   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1087    4.5929   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4385    3.9275   -3.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8119    2.4645   -5.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008    2.8309   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
 14 15  1  0
 18 11  1  0
 15 17  1  0
 15 16  2  0
 11  7  1  0
  7  8  1  0
 18  4  1  0
  8 10  1  0
  4  5  1  0
  8  9  2  0
  5  6  1  0
  4  3  1  0
 11 12  1  0
  3  2  1  0
 12 13  1  0
  2  1  1  0
 13 14  2  0
 11 27  1  1
 14 18  1  0
 18 32  1  1
  4 24  1  6
  6 25  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 17 31  1  0
 10 26  1  0
  2 22  1  0
  2 23  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.812  -0.796   1.888  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.239  -0.712   0.487  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.581   0.545   0.349  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.012   0.716  -0.963  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.062  -0.209  -1.196  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.212   0.070  -0.505  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.533   1.262   0.015  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.748   1.428   0.839  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.054   2.443   1.440  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.532   0.338   0.880  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.665   2.482  -0.198  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.411   3.606  -0.952  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.960   3.438  -2.365  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.122   2.652  -2.446  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.855   2.333  -3.673  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.928   1.762  -3.726  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.220   2.742  -4.782  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.573   2.183  -1.087  0.00  0.00           C+0
HETATM   19  H   UNK     0      -2.017  -0.703   2.636  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.515   0.023   2.067  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.330  -1.747   2.041  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.047  -0.791  -0.248  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.529  -1.531   0.331  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.796   0.492  -1.692  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.828  -0.819  -0.439  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.276   0.607   1.458  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.337   2.840   0.787  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.500   3.532  -0.886  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.109   4.593  -0.584  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.438   3.928  -3.203  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.812   2.465  -5.511  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.401   2.831  -0.765  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    3    1   22   23                                             
CONECT    3    4    2                                                       
CONECT    4   18    5    3   24                                             
CONECT    5    4    6                                                       
CONECT    6    7    5   25                                                  
CONECT    7    6   11    8                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   26                                                       
CONECT   11   18    7   12   27                                             
CONECT   12   11   13   28   29                                             
CONECT   13   12   14   30                                                  
CONECT   14   15   13   18                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15   31                                                       
CONECT   18   11    4   14   32                                             
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    2                                                            
CONECT   24    4                                                            
CONECT   25    6                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

RDKit          3D

32 33  0  0  0  0  0  0  0  0999 V2000
   -2.8118   -0.7964    1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392   -0.7122    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5808    0.5448    0.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0118    0.7158   -0.9629 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0622   -0.2093   -1.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117    0.0700   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5331    1.2623    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477    1.4277    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543    2.4428    1.4399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317    0.3384    0.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649    2.4821   -0.1978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4112    3.6059   -0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    3.4380   -2.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223    2.6519   -2.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    2.3329   -3.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9283    1.7620   -3.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203    2.7422   -4.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728    2.1834   -1.0871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0167   -0.7030    2.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5153    0.0234    2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.7469    2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475   -0.7910   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5290   -1.5309    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7961    0.4924   -1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283   -0.8186   -0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2756    0.6074    1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3370    2.8403    0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    3.5324   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1087    4.5929   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4385    3.9275   -3.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8119    2.4645   -5.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008    2.8309   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
 14 15  1  0
 18 11  1  0
 15 17  1  0
 15 16  2  0
 11  7  1  0
  7  8  1  0
 18  4  1  0
  8 10  1  0
  4  5  1  0
  8  9  2  0
  5  6  1  0
  4  3  1  0
 11 12  1  0
  3  2  1  0
 12 13  1  0
  2  1  1  0
 13 14  2  0
 11 27  1  1
 14 18  1  0
 18 32  1  1
  4 24  1  6
  6 25  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 17 31  1  0
 10 26  1  0
  2 22  1  0
  2 23  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1R,4AS,7as)-1-ethoxy-1H,4ah,5H,7ah-cyclopenta[c]pyran-4,7-dicarboxylate	Generator

Chemical Formula

C₁₂H₁₄O₆

Average Mass

254.2380 Da

Monoisotopic Mass

254.07904 Da

IUPAC Name

(1R,4aS,7aS)-1-ethoxy-1H,4aH,5H,7aH-cyclopenta[c]pyran-4,7-dicarboxylic acid

Traditional Name

(1R,4aS,7aS)-1-ethoxy-1H,4aH,5H,7aH-cyclopenta[c]pyran-4,7-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C([H])([H])[C@]2([H])C(=C([H])O[C@@]([H])(OC([H])([H])C([H])([H])[H])[C@]12[H])C(=O)O[H]

InChI Identifier

InChI=1S/C12H14O6/c1-2-17-12-9-6(3-4-7(9)10(13)14)8(5-18-12)11(15)16/h4-6,9,12H,2-3H2,1H3,(H,13,14)(H,15,16)/t6-,9+,12-/m1/s1

InChI Key

WWRWHCABBGNGCZ-PUQNFTFYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tarenna attenuata	JEOL database	Yang, X.-W., et al, J. Nat. Prod. 69, 971 (2006)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Bicyclic monoterpenoid
Dicarboxylic acid or derivatives
Vinylogous ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	1.7	ALOGPS
logP	0.65	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.96	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	60.77 m³·mol⁻¹	ChemAxon
Polarizability	24.53 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

Not Available

Chemspider ID

9761666

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11586902

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang, X.-W., et al. (2006). Yang, X.-W., et al, J. Nat. Prod. 69, 971 (2006). J. Nat. Prod..

Showing NP-Card for tarennin (NP0040757)

MOL for NP0040757 (tarennin)

3D MOL for NP0040757 (tarennin)

3D SDF for NP0040757 (tarennin)

3D-SDF for NP0040757 (tarennin)

PDB for NP0040757 (tarennin)

3D PDB for NP0040757 (tarennin)

SMILES for NP0040757 (tarennin)

INCHI for NP0040757 (tarennin)

Structure for NP0040757 (tarennin)

3D Structure for NP0040757 (tarennin)