NP-MRD: Showing NP-Card for (20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol (NP0225589)

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Record Information

Version

2.0

Created at

2022-09-06 04:21:09 UTC

Updated at

2022-09-06 04:21:10 UTC

NP-MRD ID

NP0225589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol

Description

Bazzanin A belongs to the class of organic compounds known as halophenols. These are aromatic compounds containing benzene substituted by a hydroxyl group and a halogen atom. (20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol is found in Bazzania trilobata. Based on a literature review very few articles have been published on Bazzanin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221572D          

 33 37  0  0  0  0            999 V2000
    2.5323   -0.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1899    0.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0728    0.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0460   -0.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7054   -1.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4815   -0.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328    0.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8560    0.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2775    0.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8550   -1.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9502   -2.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7075   -2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3696   -2.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2744   -1.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5171   -1.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1269   -2.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6049   -3.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9255   -3.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588   -3.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7215   -4.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8988   -4.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3995   -4.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6818   -3.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956   -2.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8677   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765   -1.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1161   -1.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155   -1.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0428   -1.9269    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8777   -3.3425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243   -3.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -4.2765    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
  1 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 26 30  1  0  0  0  0
 25 31  1  0  0  0  0
 23 32  2  0  0  0  0
 19 32  1  0  0  0  0
 22 33  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    6.0883    2.8784    0.7888 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    1.8942    0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2804    0.6561    1.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194   -0.2444    1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0535   -0.0980    0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274    1.2117   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9440    2.1467    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8623    1.7511   -0.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1539    2.9113   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3368    2.6271   -0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    3.4611   -1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2866    3.2052   -1.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920    2.0706   -1.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642    1.8817   -1.6244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2442    1.2007   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406    1.5036    0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9252   -0.1549    0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361   -1.3919   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9473   -2.5517    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1604   -2.5001    0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7585   -1.3115    1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628   -1.3088    2.0149 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.1230   -0.1516    0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7838    0.9968    1.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4581   -3.9547   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1935   -4.3486    0.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705   -3.2609    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0237   -2.3437    1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0180   -1.3615    1.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9849   -1.1215    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776   -2.0403   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896   -2.1969   -1.9843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786   -3.0281   -0.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9515    2.6727    1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2153    0.4204    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5739   -1.2222    1.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625    3.1669   -0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2919    2.1916   -1.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1410    1.0164   -1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406    3.8090   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6630    3.1384    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449    4.3784   -1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7790    3.8816   -2.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7470    1.1009   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4461    0.9214    1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099   -1.4182   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6934   -3.4218    1.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5193    1.9354    1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980   -4.7876   -0.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1056   -5.4514    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491   -2.2080    2.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8331   -0.7608    2.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3051   -2.8483   -2.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8926   -3.5421   -1.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  5 30  1  0
 30 29  2  0
 29 28  1  0
 28 27  2  0
 27 33  1  0
 33 31  2  0
 31 32  1  0
 27 26  1  0
 26 25  2  0
 25 19  1  0
 19 18  2  0
 18 17  1  0
 17 23  2  0
 23 24  1  0
 23 21  1  0
 21 22  1  0
 21 20  2  0
 17 15  1  0
 15 16  2  0
 16 10  1  0
 10  9  1  0
  9  8  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  3  2  1  0
 31 30  1  0
 20 19  1  0
 13 15  1  0
  8  6  1  0
  1 34  1  0
  7 37  1  0
  4 36  1  0
  3 35  1  0
 29 52  1  0
 28 51  1  0
 33 54  1  0
 32 53  1  0
 26 50  1  0
 25 49  1  0
 18 46  1  0
 24 48  1  0
 20 47  1  0
 16 45  1  0
  9 40  1  0
  9 41  1  0
  8 38  1  0
  8 39  1  0
 11 42  1  0
 12 43  1  0
 14 44  1  0
M  END


  Mrv1652304282221572D          

 33 37  0  0  0  0            999 V2000
    2.5323   -0.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1899    0.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0728    0.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0460   -0.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7054   -1.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4815   -0.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328    0.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8560    0.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2775    0.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8550   -1.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9502   -2.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7075   -2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3696   -2.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2744   -1.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5171   -1.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1269   -2.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6049   -3.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9255   -3.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588   -3.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7215   -4.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8988   -4.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3995   -4.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6818   -3.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956   -2.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8677   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765   -1.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1161   -1.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155   -1.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0428   -1.9269    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8777   -3.3425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5243   -3.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -4.2765    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
  1 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 26 30  1  0  0  0  0
 25 31  1  0  0  0  0
 23 32  2  0  0  0  0
 19 32  1  0  0  0  0
 22 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C1=CC=C(C=C1O)\C=C/C1=CC(=C(O)C(Cl)=C1)C1=CC(CC2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H21ClO4/c29-25-13-18-2-1-17-4-8-22(27(32)14-17)21-9-7-20(30)15-19(21)6-3-16-5-10-26(31)23(11-16)24(12-18)28(25)33/h1-2,4-5,7-15,30-33H,3,6H2/b2-1-

> <INCHI_KEY>
SRLGMZCGYURDNJ-UPHRSURJSA-N

> <FORMULA>
C28H21ClO4

> <MOLECULAR_WEIGHT>
456.92

> <EXACT_MASS>
456.1128369

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
47.829347171145116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(20E)-17-chloropentacyclo[20.2.2.1^{10,14}.1^{15,19}.0^{2,7}]octacosa-1(25),2(7),3,5,10,12,14(28),15,17,19(27),20,22(26),23-tridecaene-5,13,16,24-tetrol

> <ALOGPS_LOGP>
5.58

> <JCHEM_LOGP>
7.560437840999999

> <ALOGPS_LOGS>
-5.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.608448442744574

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.004543880886467

> <JCHEM_PKA_STRONGEST_BASIC>
-5.495219742616968

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
132.79379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.73e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(20E)-17-chloropentacyclo[20.2.2.1^{10,14}.1^{15,19}.0^{2,7}]octacosa-1(25),2(7),3,5,10,12,14(28),15,17,19(27),20,22(26),23-tridecaene-5,13,16,24-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.727  -0.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.954   0.272   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.603   0.446   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.553  -1.116   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.783  -2.024   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.232  -1.474   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.328   0.110   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.065   1.013   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.718   0.772   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.929  -2.958   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.107  -4.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.521  -5.099   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.757  -4.180   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.579  -2.651   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.165  -2.040   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.170  -4.791   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.462  -6.011   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.194  -7.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.577  -7.344   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.947  -8.785   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.411  -8.991   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.479  -7.750   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.006  -6.262   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -4.961   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.418  -4.912   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.620  -3.579   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.383  -2.235   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.950  -2.172   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.696  -3.556   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0       0.080  -3.597   0.000  0.00  0.00          Cl+0
HETATM   31  O   UNK     0       1.638  -6.239   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.579  -6.126   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.957  -7.983   0.000  0.00  0.00           O+0
CONECT    1    2   28                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7                                                            
CONECT   10    6   11   15                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13                                                            
CONECT   17   11   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   33                                                  
CONECT   23   22   24   32                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27    1   29                                                  
CONECT   29   28   24                                                       
CONECT   30   26                                                            
CONECT   31   25                                                            
CONECT   32   23   19                                                       
CONECT   33   22                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₁ClO₄

Average Mass

456.9200 Da

Monoisotopic Mass

456.11284 Da

IUPAC Name

(20E)-17-chloropentacyclo[20.2.2.1^{10,14}.1^{15,19}.0^{2,7}]octacosa-1(25),2(7),3,5,10,12,14(28),15,17,19(27),20,22(26),23-tridecaene-5,13,16,24-tetrol

Traditional Name

(20E)-17-chloropentacyclo[20.2.2.1^{10,14}.1^{15,19}.0^{2,7}]octacosa-1(25),2(7),3,5,10,12,14(28),15,17,19(27),20,22(26),23-tridecaene-5,13,16,24-tetrol

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C=C1)C1=CC=C(C=C1O)\C=C/C1=CC(=C(O)C(Cl)=C1)C1=CC(CC2)=CC=C1O

InChI Identifier

InChI=1S/C28H21ClO4/c29-25-13-18-2-1-17-4-8-22(27(32)14-17)21-9-7-20(30)15-19(21)6-3-16-5-10-26(31)23(11-16)24(12-18)28(25)33/h1-2,4-5,7-15,30-33H,3,6H2/b2-1-

InChI Key

SRLGMZCGYURDNJ-UPHRSURJSA-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
Bazzania trilobata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as halophenols. These are aromatic compounds containing benzene substituted by a hydroxyl group and a halogen atom.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

2-halophenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aryl halide
Aryl chloride
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	5.58	ALOGPS
logP	7.56	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	7	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	132.79 m³·mol⁻¹	ChemAxon
Polarizability	47.83 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00036043

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

101938848

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol (NP0225589)

MOL for NP0225589 ((20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol)

3D MOL for NP0225589 ((20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol)

3D SDF for NP0225589 ((20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol)

3D-SDF for NP0225589 ((20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol)

PDB for NP0225589 ((20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol)

3D PDB for NP0225589 ((20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol)

SMILES for NP0225589 ((20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol)

INCHI for NP0225589 ((20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol)

Structure for NP0225589 ((20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol)

3D Structure for NP0225589 ((20e)-17-chloropentacyclo[20.2.2.1¹⁰,¹⁴.1¹⁵,¹⁹.0²,⁷]octacosa-1(25),2,4,6,10,12,14(28),15(27),16,18,20,22(26),23-tridecaene-5,13,16,24-tetrol)