NP-MRD: Showing NP-Card for (6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione (NP0226317)

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Record Information

Version

2.0

Created at

2022-09-06 05:18:42 UTC

Updated at

2022-09-06 05:18:42 UTC

NP-MRD ID

NP0226317

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione

Description

Chaetomugilin M belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione is found in Mugil cephalus. Based on a literature review very few articles have been published on Chaetomugilin M.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062207182D          

 31 33  0  0  1  0            999 V2000
   -2.7387   -2.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9141   -2.1502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5241   -2.8772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795   -1.4490    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8694   -0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549   -1.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9082    1.3045    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1228    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5574    1.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -0.1753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0183    0.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -0.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0758   -1.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.5066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4141   -2.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6219   -2.5381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0097   -2.8787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8019   -2.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8130   -3.6799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4086   -4.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208   -3.9102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.8765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2535   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -1.5262    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  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  1  0  0  0
 20 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  1  0  0  0
 10 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    7.1638    2.6817    0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7407    2.3265   -0.1269 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4284    2.8178   -1.3905 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5786    0.8235   -0.0792 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5089    0.2333   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1949    0.4086   -0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4313   -0.2975    0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0704   -0.6886    0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3905   -1.3918    0.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0047   -1.7994    0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6829   -2.4982    1.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1204   -2.9009    3.0553 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0350   -2.9025    1.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029   -3.4537    2.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6565   -2.6888   -0.0453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8379   -4.0904   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9825   -2.1663    0.0721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1723   -1.3938   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2213   -1.4100   -1.7912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946   -0.6639   -1.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7737    0.4055   -0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9078    0.3460    0.6418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6054    1.6063   -0.2490 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1905    2.5606    0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0772    1.4486   -0.1558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5523    0.7174    1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6244    2.7821   -0.0888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244   -1.8071   -0.9891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5830   -1.4236   -0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1697   -0.7225   -1.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4764   -0.3550   -1.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7367    3.0156   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7203    1.8463    0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2231    3.5325    0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0974    2.8317    0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1998    3.2681   -1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9225    0.4752    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5212    0.0362   -0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6433    0.9018   -1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0965   -0.7531   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605    0.6869   -1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8718   -0.5687    1.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8423   -1.6607    1.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -4.3714   -1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5557   -4.0343   -1.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1729   -4.7511    0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -0.2448   -2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4291    2.2520   -1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2217    3.0263    0.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9683    3.3516    0.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2110    2.0512    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5607    1.0466   -1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9411    1.4447    1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7926    0.0371    1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4401    0.0772    0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5567    2.7297    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8629   -2.3382   -1.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1692   -0.3925   -2.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 31  8  1  0
 29 10  1  0
 28 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  1
  3 36  1  0
  4 37  1  1
  5 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  7 42  1  0
  9 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 20 47  1  6
 28 57  1  6
 30 58  1  0
 23 48  1  6
 24 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  6
 26 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
M  END


  Mrv1652309062207182D          

 31 33  0  0  1  0            999 V2000
   -2.7387   -2.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9141   -2.1502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5241   -2.8772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795   -1.4490    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8694   -0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549   -1.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9082    1.3045    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1228    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5574    1.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -0.1753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0183    0.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -0.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0758   -1.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.5066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4141   -2.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6219   -2.5381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0097   -2.8787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8019   -2.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8130   -3.6799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4086   -4.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208   -3.9102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.8765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2535   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -1.5262    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  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  1  0  0  0
 20 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  1  0  0  0
 10 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226317

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](C)\C=C\C1=CC2=C(Cl)C(=O)[C@@]3(C)OC(=O)[C@H]([C@H]3C2=CO1)C(=O)[C@H](C)[C@@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C23H27ClO7/c1-10(12(3)25)6-7-14-8-15-16(9-30-14)18-17(20(27)11(2)13(4)26)22(29)31-23(18,5)21(28)19(15)24/h6-13,17-18,25-26H,1-5H3/b7-6+/t10-,11-,12-,13-,17-,18-,23+/m1/s1

> <INCHI_KEY>
MEPQPODJTXSHEP-MGAKCBRVSA-N

> <FORMULA>
C23H27ClO7

> <MOLECULAR_WEIGHT>
450.91

> <EXACT_MASS>
450.1445309

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.40293788863784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6aS,9R,9aS)-5-chloro-9-[(2R,3R)-3-hydroxy-2-methylbutanoyl]-3-[(1E,3R,4R)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromene-6,8-dione

> <JCHEM_LOGP>
1.9005210573333324

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.16939844852292

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.743254137762909

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3680110562855567

> <JCHEM_POLAR_SURFACE_AREA>
110.13

> <JCHEM_REFRACTIVITY>
117.84629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6aS,9R,9aS)-5-chloro-9-[(2R,3R)-3-hydroxy-2-methylbutanoyl]-3-[(1E,3R,4R)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9H,9aH-furo[2,3-h]isochromene-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.112  -3.966   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.573  -4.014   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.845  -5.371   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.762  -2.705   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.490  -1.348   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.222  -2.753   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.411  -1.444   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.128  -1.492   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.939  -0.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.479  -0.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.290   1.078   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0       3.562   2.435   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0       5.829   1.030   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.640   2.339   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.557  -0.327   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.501   0.890   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.053  -0.694   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.166  -2.230   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.475  -3.041   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.740  -2.812   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.373  -4.308   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.894  -4.738   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.485  -5.374   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.963  -4.944   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.118  -6.869   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.229  -7.935   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.639  -7.299   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.746  -1.636   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.207  -1.588   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.395  -2.897   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.856  -2.849   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   28                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20   15   29                                                  
CONECT   29   28   10   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30    8                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₇ClO₇

Average Mass

450.9100 Da

Monoisotopic Mass

450.14453 Da

IUPAC Name

(6aS,9R,9aS)-5-chloro-9-[(2R,3R)-3-hydroxy-2-methylbutanoyl]-3-[(1E,3R,4R)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromene-6,8-dione

Traditional Name

(6aS,9R,9aS)-5-chloro-9-[(2R,3R)-3-hydroxy-2-methylbutanoyl]-3-[(1E,3R,4R)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9H,9aH-furo[2,3-h]isochromene-6,8-dione

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@H](C)\C=C\C1=CC2=C(Cl)C(=O)[C@@]3(C)OC(=O)[C@H]([C@H]3C2=CO1)C(=O)[C@H](C)[C@@H](C)O

InChI Identifier

InChI=1S/C23H27ClO7/c1-10(12(3)25)6-7-14-8-15-16(9-30-14)18-17(20(27)11(2)13(4)26)22(29)31-23(18,5)21(28)19(15)24/h6-13,17-18,25-26H,1-5H3/b7-6+/t10-,11-,12-,13-,17-,18-,23+/m1/s1

InChI Key

MEPQPODJTXSHEP-MGAKCBRVSA-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
Mugil cephalus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha-acyloxy ketone
Beta-hydroxy ketone
Gamma butyrolactone
Pyran
1,3-dicarbonyl compound
Alpha-haloketone
Alpha-chloroketone
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Chloroalkene
Monocarboxylic acid or derivatives
Haloalkene
Organoheterocyclic compound
Vinyl chloride
Vinyl halide
Organohalogen compound
Organochloride
Hydrocarbon derivative
Organic oxide
Alcohol
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	1.9	ChemAxon
pKa (Strongest Acidic)	11.74	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	117.85 m³·mol⁻¹	ChemAxon
Polarizability	45.4 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

C00052917

Chemspider ID

27024231

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44250067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione (NP0226317)

MOL for NP0226317 ((6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D MOL for NP0226317 ((6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D SDF for NP0226317 ((6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D-SDF for NP0226317 ((6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

PDB for NP0226317 ((6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D PDB for NP0226317 ((6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

SMILES for NP0226317 ((6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

INCHI for NP0226317 ((6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

Structure for NP0226317 ((6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D Structure for NP0226317 ((6as,9r,9as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-3-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)