NP-MRD: Showing NP-Card for Helicusin B (NP0084084)

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Record Information

Version

2.0

Created at

2022-04-29 04:55:45 UTC

Updated at

2022-04-29 04:55:45 UTC

NP-MRD ID

NP0084084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Helicusin B

Description

Helicusin B belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center. Helicusin B is found in Talaromyces helicus, Talaromyces helius IFM 42241 and Talaroymces helicus. Based on a literature review very few articles have been published on Helicusin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206552D          

 33 34  0  0  1  0            999 V2000
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4323    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    0.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6623    1.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    1.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    0.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176    0.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3479    0.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    1.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570    2.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -0.1260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 16  2  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 22 30  2  0  0  0  0
 20 31  1  6  0  0  0
 20 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
   -9.5676    2.4832   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1067    2.6016    0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5233    1.1681   -0.0047 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2839    0.3334    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1377    1.2388    0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2364    0.5605   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9001   -0.1291   -1.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255    0.4449   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6994    0.2931    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417    0.2568    0.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535   -0.3552   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7459   -0.5450   -0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675   -1.0657   -1.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5188   -1.4613   -2.8584 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8965   -1.1741   -1.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5835   -1.1277   -2.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219   -1.3396   -0.0319 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2768   -2.7566    0.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9239   -1.0791   -0.0438 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7038   -1.2513    1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9256   -1.7430    2.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9972   -1.1431    1.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1105   -0.6946    1.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3630   -0.8188    2.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4584    0.0752   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6541    0.7299   -1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4666    0.9782   -1.0322 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3645    1.1774   -2.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8846   -0.3876    0.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388    0.1509    1.8085 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4638   -0.1454    0.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7180    0.4212    1.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382    0.6182    1.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1543    2.8076    0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8037    1.4220   -0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8208    3.1795   -1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9932    2.9423    1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5516    3.1940   -0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6755    0.8187   -1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8687    0.9499    1.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8990   -0.4394    0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5093   -0.2186    1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7920    1.7337    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7037   -0.8358   -1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1093   -0.8598   -1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1381    0.5171   -2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7079   -0.6845   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875    1.1234    1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032   -0.6094   -1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021   -3.0616    1.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -3.4196   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -3.0767   -0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0862   -1.5575    2.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9877   -1.4183    2.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4990    0.2165    2.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1359   -1.2689    1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2049    0.9309    0.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3084   -0.5236   -0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3921    1.1094   -2.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2670    0.7138    2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  6
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 28  1  0
 26 27  2  0
 17 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 10  1  0
 31 12  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  6
  4 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  7 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  9 48  1  0
 11 49  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 28 59  1  0
 32 60  1  0
M  END


  Mrv1652304292206552D          

 33 34  0  0  1  0            999 V2000
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4323    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    0.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6623    1.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    1.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    0.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176    0.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3479    0.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    1.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570    2.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -0.1260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 16  2  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 22 30  2  0  0  0  0
 20 31  1  6  0  0  0
 20 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084084

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H27ClO7/c1-6-14(2)9-15(3)7-8-17-12-18-19(13-32-17)23(30)25(5,24(31)22(18)26)33-21(29)11-16(4)10-20(27)28/h7-9,11-14H,6,10H2,1-5H3,(H,27,28)/b8-7+,15-9+,16-11-/t14-,25-/m0/s1

> <INCHI_KEY>
HIYBJBWWMULNJP-XNUAZITHSA-N

> <FORMULA>
C25H27ClO7

> <MOLECULAR_WEIGHT>
474.93

> <EXACT_MASS>
474.1445309

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.997941033841926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-5-{[(7S)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
4.646048664666667

> <ALOGPS_LOGS>
-6.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8546611432041153

> <JCHEM_PKA_STRONGEST_BASIC>
-5.24224813178047

> <JCHEM_POLAR_SURFACE_AREA>
106.97

> <JCHEM_REFRACTIVITY>
128.90599999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-5-{[(7S)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       2.667  -4.620   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.807   0.677   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.710   0.945   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.236   2.392   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.753   2.659   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.743   1.479   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.259   1.747   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.249   0.567   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -5.786   3.194   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.280   4.106   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.700  -0.235   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.183  -1.037   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    6   17                                                       
CONECT   17   16    3   18                                                  
CONECT   18   17   19   32                                                  
CONECT   19   18                                                            
CONECT   20    2   21   31   32                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24                                                            
CONECT   30   22                                                            
CONECT   31   20                                                            
CONECT   32   20   18   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₇ClO₇

Average Mass

474.9300 Da

Monoisotopic Mass

474.14453 Da

IUPAC Name

(3Z)-5-{[(7S)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

Traditional Name

(3Z)-5-{[(7S)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H27ClO7/c1-6-14(2)9-15(3)7-8-17-12-18-19(13-32-17)23(30)25(5,24(31)22(18)26)33-21(29)11-16(4)10-20(27)28/h7-9,11-14H,6,10H2,1-5H3,(H,27,28)/b8-7+,15-9+,16-11-/t14-,25-/m0/s1

InChI Key

HIYBJBWWMULNJP-XNUAZITHSA-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
Talaromyces helicus	LOTUS Database	35616633
Talaromyces helius IFM 42241	Fungi	KNApSAcK
Talaroymces helicus	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaphilones

Sub Class

Not Available

Direct Parent

Azaphilones

Alternative Parents

Substituents

Azaphilone
Methyl-branched fatty acid
Alpha-acyloxy ketone
Heterocyclic fatty acid
Halogenated fatty acid
Fatty acid ester
Cyclohexenone
Branched fatty acid
Pyran
Fatty acyl
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Alpha-haloketone
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Alpha-chloroketone
Ketone
Cyclic ketone
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Carbonyl group
Organic oxide
Organic oxygen compound
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.41	ALOGPS
logP	4.65	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	128.91 m³·mol⁻¹	ChemAxon
Polarizability	49 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

C00053294

Chemspider ID

8180717

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10005137

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Helicusin B (NP0084084)

MOL for NP0084084 (Helicusin B)

3D MOL for NP0084084 (Helicusin B)

3D SDF for NP0084084 (Helicusin B)

3D-SDF for NP0084084 (Helicusin B)

PDB for NP0084084 (Helicusin B)

3D PDB for NP0084084 (Helicusin B)

SMILES for NP0084084 (Helicusin B)

INCHI for NP0084084 (Helicusin B)

Structure for NP0084084 (Helicusin B)

3D Structure for NP0084084 (Helicusin B)