Np mrd loader

Showing NP-Card for (1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione (NP0282508)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-09 09:21:44 UTC
Updated at2024-09-12 20:52:49 UTC
NP-MRD IDNP0282508
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione
Description16-Dechloro-16-hydroxynapyradiomycin C2 belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. (1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione is found in Streptomyces antimycoticus. (1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione was first documented in 2008 (PMID: 18271555). Based on a literature review very few articles have been published on 16-dechloro-16-hydroxynapyradiomycin C2.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0282508 ((1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione)

NP0007560
  Mrv2104 05272322483D          

 61 64  0  0  0  0            999 V2000
    5.0078   -2.6033   -2.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -1.8514   -1.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2261   -1.0552   -2.9449 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7443   -0.8398   -2.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555   -1.9237   -2.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866   -3.1323   -3.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4143   -1.8040   -2.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887   -0.5847   -1.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0025    0.5464   -1.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2598    0.4226   -2.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973    1.4998   -2.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4162    1.8331   -1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718    2.8518   -1.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3845    1.8591    0.0448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4461    2.7370    1.3508 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5477    2.8287   -0.2992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8631    2.1321   -0.6080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7482    1.3782   -2.2311 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2430    1.1687    0.5467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8486    2.0024    1.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3140    0.1364    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1312    0.5039    1.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8456    0.4459    0.5144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9199   -0.2555    1.6006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5691   -0.4579    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245   -0.0845    2.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    0.6177    3.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0940   -0.3444    1.7336 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5486   -0.4261    0.2597 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4368   -1.8077   -0.4044 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1805   -2.7385    0.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -0.5774   -0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7609   -1.4563   -0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3545   -2.6394   -3.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5609   -3.2002   -1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7447   -0.0944   -3.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3404   -1.5493   -3.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5578   -3.7751   -3.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -2.6724   -2.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5955    2.3275   -2.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7421    3.5061    0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847    3.4993   -1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6510    2.8841   -0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156    2.6994    2.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7241    2.5730    1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1528    1.3546    2.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9817   -0.5471   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5667   -0.4976    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2304    0.6246   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876    0.2524    2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3293   -1.2619    1.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929   -1.0583    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    0.0665    4.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9067    1.6290    3.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    0.7021    3.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340   -1.2232    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616    0.5010    2.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6125   -0.1481    0.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331    0.3452   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4054   -2.1655   -0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5519   -3.1534    1.0058 H   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  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
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  2  0  0  0  0
 30  2  1  0  0  0  0
 10  4  1  0  0  0  0
 23 14  1  0  0  0  0
 32  8  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  6 38  1  0  0  0  0
  7 39  1  0  0  0  0
 11 40  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 17 43  1  6  0  0  0
 20 44  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
 25 52  1  0  0  0  0
 27 53  1  0  0  0  0
 27 54  1  0  0  0  0
 27 55  1  0  0  0  0
 28 56  1  0  0  0  0
 28 57  1  0  0  0  0
 29 58  1  0  0  0  0
 29 59  1  0  0  0  0
 30 60  1  0  0  0  0
 31 61  1  0  0  0  0
M  END
Download

3D MOL for NP0282508 ((1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione)

Download
3D SDF for NP0282508 ((1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione)
NP0007560
  Mrv2104 05272322483D          

 61 64  0  0  0  0            999 V2000
    5.0078   -2.6033   -2.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -1.8514   -1.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2261   -1.0552   -2.9449 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7443   -0.8398   -2.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555   -1.9237   -2.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866   -3.1323   -3.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4143   -1.8040   -2.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7887   -0.5847   -1.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0025    0.5464   -1.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2598    0.4226   -2.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973    1.4998   -2.4655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4162    1.8331   -1.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718    2.8518   -1.6398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3845    1.8591    0.0448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4461    2.7370    1.3508 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5477    2.8287   -0.2992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8631    2.1321   -0.6080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7482    1.3782   -2.2311 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2430    1.1687    0.5467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8486    2.0024    1.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3140    0.1364    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1312    0.5039    1.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8456    0.4459    0.5144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9199   -0.2555    1.6006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5691   -0.4579    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245   -0.0845    2.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    0.6177    3.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0940   -0.3444    1.7336 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5486   -0.4261    0.2597 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4368   -1.8077   -0.4044 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1805   -2.7385    0.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -0.5774   -0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7609   -1.4563   -0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3545   -2.6394   -3.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5609   -3.2002   -1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7447   -0.0944   -3.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3404   -1.5493   -3.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5578   -3.7751   -3.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -2.6724   -2.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5955    2.3275   -2.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7421    3.5061    0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847    3.4993   -1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6510    2.8841   -0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156    2.6994    2.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7241    2.5730    1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1528    1.3546    2.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9817   -0.5471   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5667   -0.4976    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2304    0.6246   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876    0.2524    2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3293   -1.2619    1.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929   -1.0583    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    0.0665    4.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9067    1.6290    3.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    0.7021    3.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340   -1.2232    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616    0.5010    2.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6125   -0.1481    0.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331    0.3452   -0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4054   -2.1655   -0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5519   -3.1534    1.0058 H   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  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
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  2  0  0  0  0
 30  2  1  0  0  0  0
 10  4  1  0  0  0  0
 23 14  1  0  0  0  0
 32  8  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  6 38  1  0  0  0  0
  7 39  1  0  0  0  0
 11 40  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 17 43  1  6  0  0  0
 20 44  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
 25 52  1  0  0  0  0
 27 53  1  0  0  0  0
 27 54  1  0  0  0  0
 27 55  1  0  0  0  0
 28 56  1  0  0  0  0
 28 57  1  0  0  0  0
 29 58  1  0  0  0  0
 29 59  1  0  0  0  0
 30 60  1  0  0  0  0
 31 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0282508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(O[H])=C3C(=C1[H])C(=O)[C@@]1(OC(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(Cl)C([H])([H])[C@]1(Cl)C3=O)C([H])([H])\C([H])=C(C([H])([H])[H])\C([H])([H])C([H])([H])[C@]([H])(O[H])C(=C([H])[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1/C25H28Cl2O6/c1-12-5-6-16(28)13(2)9-14-17(29)10-15-19(20(14)30)22(32)24(27)11-18(26)23(3,4)33-25(24,8-7-12)21(15)31/h7,10,16,18,28-30H,2,5-6,8-9,11H2,1,3-4H3/b12-7+/t16-,18+,24-,25-/s2

> <INCHI_KEY>
UTXOFYRFSXYWKW-ZPHOYFKCNA-N

> <FORMULA>
C25H28Cl2O6

> <MOLECULAR_WEIGHT>
495.39

> <EXACT_MASS>
494.126294

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.101420747035505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3E,7S,16R,18R)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1^{10,14}.0^{1,16}]docosa-3,10,12,14(22)-tetraene-15,21-dione

> <JCHEM_LOGP>
4.950650369666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.65034721057355

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.008644844056324

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9681828380270376

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
127.20669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3E,7S,16R,18R)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1^{10,14}.0^{1,16}]docosa-3,10,12,14(22)-tetraene-15,21-dione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0282508 ((1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione)
Download
PDB for NP0282508 ((1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione)
HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NP0007560                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       5.008  -2.603  -2.216  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.949  -1.851  -1.850  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.226  -1.055  -2.945  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.744  -0.840  -2.708  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.856  -1.924  -2.712  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.287  -3.132  -3.175  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.414  -1.804  -2.163  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.789  -0.585  -1.587  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.003   0.546  -1.727  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.260   0.423  -2.328  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.097   1.500  -2.466  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.416   1.833  -1.144  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.072   2.852  -1.640  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.385   1.859   0.045  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -0.446   2.737   1.351  0.00  0.00          Cl+0
HETATM   16  C   UNK     0      -2.548   2.829  -0.299  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.863   2.132  -0.608  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -3.748   1.378  -2.231  0.00  0.00          Cl+0
HETATM   19  C   UNK     0      -4.243   1.169   0.547  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.849   2.002   1.702  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.314   0.136   0.164  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.131   0.504   1.171  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.846   0.446   0.514  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.920  -0.256   1.601  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.569  -0.458   1.337  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.625  -0.085   2.092  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.492   0.618   3.426  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.094  -0.344   1.734  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.549  -0.426   0.260  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.437  -1.808  -0.404  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.181  -2.739   0.393  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.910  -0.577  -0.639  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.761  -1.456  -0.737  0.00  0.00           O+0
HETATM   34  H   UNK     0       5.354  -2.639  -3.243  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.561  -3.200  -1.497  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.745  -0.094  -3.046  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.340  -1.549  -3.919  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.558  -3.775  -3.164  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.063  -2.672  -2.071  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.595   2.328  -2.287  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.742   3.506   0.543  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.285   3.499  -1.128  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.651   2.884  -0.728  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.116   2.699   2.123  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.724   2.573   1.376  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.153   1.355   2.534  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.982  -0.547  -0.620  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.567  -0.498   1.022  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.230   0.625  -0.186  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.088   0.252   2.556  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.329  -1.262   1.780  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.793  -1.058   0.466  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.048   0.067   4.193  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.907   1.629   3.363  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.466   0.702   3.786  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.434  -1.223   2.294  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.662   0.501   2.150  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.612  -0.148   0.249  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.033   0.345  -0.314  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.405  -2.166  -0.394  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.552  -3.153   1.006  0.00  0.00           H+0
CONECT    1    2   34   35                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4   36   37                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   38                                                       
CONECT    7    5    8   39                                                  
CONECT    8    7    9   32                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11    4                                                  
CONECT   11   10   40                                                       
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   23                                             
CONECT   15   14                                                            
CONECT   16   14   17   41   42                                             
CONECT   17   16   18   19   43                                             
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19   44   45   46                                             
CONECT   21   19   47   48   49                                             
CONECT   22   19   23                                                       
CONECT   23   22   24   32   14                                             
CONECT   24   23   25   50   51                                             
CONECT   25   24   26   52                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   53   54   55                                             
CONECT   28   26   29   56   57                                             
CONECT   29   28   30   58   59                                             
CONECT   30   29   31    2   60                                             
CONECT   31   30   61                                                       
CONECT   32   23   33    8                                                  
CONECT   33   32                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40   11                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   20                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   21                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   27                                                            
CONECT   54   27                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   28                                                            
CONECT   58   29                                                            
CONECT   59   29                                                            
CONECT   60   30                                                            
CONECT   61   31                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

Download
3D PDB for NP0282508 ((1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione)
Download
SMILES for NP0282508 ((1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione)
[H]OC1=C2C(O[H])=C3C(=C1[H])C(=O)[C@@]1(OC(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(Cl)C([H])([H])[C@]1(Cl)C3=O)C([H])([H])\C([H])=C(C([H])([H])[H])\C([H])([H])C([H])([H])[C@]([H])(O[H])C(=C([H])[H])C2([H])[H]
Download
INCHI for NP0282508 ((1s,3e,16r,18r)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1¹⁰,¹⁴.0¹,¹⁶]docosa-3,10,12,14(22)-tetraene-15,21-dione)
InChI=1/C25H28Cl2O6/c1-12-5-6-16(28)13(2)9-14-17(29)10-15-19(20(14)30)22(32)24(27)11-18(26)23(3,4)33-25(24,8-7-12)21(15)31/h7,10,16,18,28-30H,2,5-6,8-9,11H2,1,3-4H3/b12-7+/t16-,18+,24-,25-/s2
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC25H28Cl2O6
Average Mass495.3900 Da
Monoisotopic Mass494.12629 Da
IUPAC Name(1S,3E,7S,16R,18R)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1^{10,14}.0^{1,16}]docosa-3,10,12,14(22)-tetraene-15,21-dione
Traditional Name(1S,3E,7S,16R,18R)-16,18-dichloro-7,11,22-trihydroxy-4,19,19-trimethyl-8-methylidene-20-oxatetracyclo[11.7.1.1^{10,14}.0^{1,16}]docosa-3,10,12,14(22)-tetraene-15,21-dione
CAS Registry NumberNot Available
SMILES
[H]OC1=C2C(O[H])=C3C(=C1[H])C(=O)[C@@]1(OC(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(Cl)C([H])([H])[C@]1(Cl)C3=O)C([H])([H])\C([H])=C(C([H])([H])[H])\C([H])([H])C([H])([H])[C@]([H])(O[H])C(=C([H])[H])C2([H])[H]
InChI Identifier
InChI=1/C25H28Cl2O6/c1-12-5-6-16(28)13(2)9-14-17(29)10-15-19(20(14)30)22(32)24(27)11-18(26)23(3,4)33-25(24,8-7-12)21(15)31/h7,10,16,18,28-30H,2,5-6,8-9,11H2,1,3-4H3/b12-7+/t16-,18+,24-,25-/s2
InChI KeyUTXOFYRFSXYWKW-ZPHOYFKCNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces antimycoticusLOTUS Database
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassNaphthopyrans  
Sub ClassNaphthopyranones  
Direct ParentNaphthopyranones  
Alternative Parents
Substituents
  • Naphthopyranone
    • 

  • Naphthoquinone
    • 

  • Tetralin
    • 

  • Naphthalene
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • Quinone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Oxane
    • 

  • Alpha-haloketone
    • 

  • Alpha-chloroketone
    • 

  • Vinylogous acid
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Polyol
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Alkyl halide
    • 

  • Alkyl chloride
    • 

  • Alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.95ChemAxon
pKa (Strongest Acidic)7.01ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity127.21 m³·mol⁻¹ChemAxon
Polarizability49.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Motohashi K, Sue M, Furihata K, Ito S, Seto H: Terpenoids Produced by Actinomycetes: Napyradiomycins from Streptomyces antimycoticus NT17. J Nat Prod. 2008 Apr;71(4):595-601. doi: 10.1021/np070575a. Epub 2008 Feb 14. [PubMed:18271555  ] 
  2. LOTUS database [Link]