NP-MRD: Showing NP-Card for 7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid (NP0190614)

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Record Information

Version

2.0

Created at

2022-09-04 07:19:09 UTC

Updated at

2022-09-04 07:19:09 UTC

NP-MRD ID

NP0190614

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid

Description

7-(3-{[Hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-4H,5H,5aH,6H,7H,8H,8aH,9H-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic 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. 7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid is found in Cacospongia mycofijiensis. 7-(3-{[Hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-4H,5H,5aH,6H,7H,8H,8aH,9H-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518352D          

 30 32  0  0  0  0            999 V2000
    7.6391    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944   -3.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201   -4.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -4.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  4  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    2.8897    7.1321    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538    5.9195    0.0709 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542    4.6837   -0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0820    4.7618   -0.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0997    3.5187    0.0021 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    2.1687   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8963    1.9112   -0.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3445    0.2790   -0.3818 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0248   -0.8200   -0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8176   -0.1971   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143    1.1620   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940    1.5476    0.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463   -1.0378    0.0579 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1678   -1.0617    1.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756   -0.9684    1.9215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2751   -0.8254    1.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9802    0.4928    1.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1881    0.6845    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2277   -0.4136    0.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4388    1.6674   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6208    2.8008   -0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963    3.0343   -0.0402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0859    3.7552   -1.4389 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8049   -2.3150   -0.5921 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0366   -3.0425   -0.1044 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9508   -4.3272   -0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5001   -4.4719   -1.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2242   -3.3734   -0.5252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5100   -3.9533    0.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2796   -2.2785   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747    7.5135   -1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9368    6.8906    0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4433    7.8234    0.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0444    3.6631    0.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6399    2.7336   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1881   -0.4721   -0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9696   -1.1640    2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2781   -0.9944    2.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969   -1.6280    1.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1066   -0.7961    0.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128    1.3408    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    0.4247    2.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1682   -0.0653    0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3022   -0.6188    1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8128   -1.2802    0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4173    1.6082   -0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0513    3.7443   -1.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0003   -2.1179   -1.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826   -3.3251    0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.2276   -1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3287   -5.1801   -0.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1476   -5.4769   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641   -4.2985   -2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643   -3.1128   -1.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4414   -5.0819    0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -3.6055    1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5863   -3.7593    1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7652   -2.4938   -1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0567   -2.4778    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 23  1  0
 21 22  2  0
 13 24  1  0
 24 28  1  0
 28 29  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 30  1  0
 10 11  1  0
 11 12  2  0
 11  6  1  0
 30  9  1  0
 25 24  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  0
  7 35  1  0
 13 36  1  6
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 23 47  1  0
 24 48  1  6
 28 54  1  6
 29 55  1  0
 29 56  1  0
 29 57  1  0
 27 52  1  0
 27 53  1  0
 26 50  1  0
 26 51  1  0
 25 49  1  1
 30 58  1  0
 30 59  1  0
M  END


  Mrv1533004231518352D          

 30 32  0  0  0  0            999 V2000
    7.6391    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944   -3.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201   -4.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -4.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  4  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0190614

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)NC1=CSC2=C(C(C=CCCC(C)=CC(O)=O)C3C(C)CCC3C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO5S/c1-13(10-19(25)26)6-4-5-7-16-20-14(2)8-9-15(20)11-18-21(16)22(27)17(12-30-18)24-23(28)29-3/h5,7,10,12,14-16,20H,4,6,8-9,11H2,1-3H3,(H,24,28)(H,25,26)

> <INCHI_KEY>
YGEMPDIMQSTDKH-UHFFFAOYSA-N

> <FORMULA>
C23H29NO5S

> <MOLECULAR_WEIGHT>
431.55

> <EXACT_MASS>
431.176644212

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.89509104026662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-{3-[(methoxycarbonyl)amino]-6-methyl-4-oxo-4H,5H,5aH,6H,7H,8H,8aH,9H-cyclopenta[g]thiochromen-5-yl}-3-methylhepta-2,6-dienoic acid

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
4.001310189

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.549540361391532

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6179773120106065

> <JCHEM_PKA_STRONGEST_BASIC>
-7.84215106316595

> <JCHEM_POLAR_SURFACE_AREA>
92.69999999999999

> <JCHEM_REFRACTIVITY>
121.15109999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-{3-[(methoxycarbonyl)amino]-6-methyl-4-oxo-5H,5aH,6H,7H,8H,8aH,9H-cyclopenta[g]thiochromen-5-yl}-3-methylhepta-2,6-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      14.260   2.073   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.926   1.303   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.592   2.073   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.592   3.613   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      10.259   1.303   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       7.591   4.383   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -1.007   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -2.547   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.257  -3.317   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.257  -4.857   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.923  -5.627   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.923  -7.167   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.411  -7.937   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.257  -7.937   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.590  -5.627   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.591  -0.237   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16                                                            
CONECT   22   11   23   27                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27    9                                                       
CONECT   29   10    6   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-4H,5H,5ah,6H,7H,8H,8ah,9H-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoate	Generator

Chemical Formula

C₂₃H₂₉NO₅S

Average Mass

431.5500 Da

Monoisotopic Mass

431.17664 Da

IUPAC Name

7-{3-[(methoxycarbonyl)amino]-6-methyl-4-oxo-4H,5H,5aH,6H,7H,8H,8aH,9H-cyclopenta[g]thiochromen-5-yl}-3-methylhepta-2,6-dienoic acid

Traditional Name

7-{3-[(methoxycarbonyl)amino]-6-methyl-4-oxo-5H,5aH,6H,7H,8H,8aH,9H-cyclopenta[g]thiochromen-5-yl}-3-methylhepta-2,6-dienoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)NC1=CSC2=C(C(C=CCCC(C)=CC(O)=O)C3C(C)CCC3C2)C1=O

InChI Identifier

InChI=1S/C23H29NO5S/c1-13(10-19(25)26)6-4-5-7-16-20-14(2)8-9-15(20)11-18-21(16)22(27)17(12-30-18)24-23(28)29-3/h5,7,10,12,14-16,20H,4,6,8-9,11H2,1-3H3,(H,24,28)(H,25,26)

InChI Key

YGEMPDIMQSTDKH-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
Cacospongia mycofijiensis	LOTUS Database	35616633

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

Aromatic monoterpenoid
11-noriridane monoterpenoid
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Heteroaromatic compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Organic 1,3-dipolar compound
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.41	ALOGPS
logP	4	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.15 m³·mol⁻¹	ChemAxon
Polarizability	46.9 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	Yes	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid (NP0190614)

MOL for NP0190614 (7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid)

3D MOL for NP0190614 (7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid)

3D SDF for NP0190614 (7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid)

3D-SDF for NP0190614 (7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid)

PDB for NP0190614 (7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid)

3D PDB for NP0190614 (7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid)

SMILES for NP0190614 (7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid)

INCHI for NP0190614 (7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid)

Structure for NP0190614 (7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid)

3D Structure for NP0190614 (7-(3-{[hydroxy(methoxy)methylidene]amino}-6-methyl-4-oxo-5h,5ah,6h,7h,8h,8ah,9h-cyclopenta[g]thiochromen-5-yl)-3-methylhepta-2,6-dienoic acid)