NP-MRD: Showing NP-Card for (3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0202870)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 22:11:16 UTC

Updated at

2022-09-04 22:11:17 UTC

NP-MRD ID

NP0202870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione

Description

DTXSID10908200 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. Based on a literature review very few articles have been published on DTXSID10908200.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052200112D          

 33 36  0  0  1  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    5.0013    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 Br  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
    4.8171    1.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7565    1.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    2.8579   -0.8250    0.0000 Cl  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
    2.1434   -1.2375    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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
    1.4289    0.8250    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
    2.1434    2.0625    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    1.7083   -2.7568    1.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889   -1.5145    2.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2453   -1.0438    3.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3056    0.0439    3.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0499    1.0854    2.6056 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3576    1.9829    2.9856 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1217    0.6540    1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5753    0.3478    0.8761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.8577    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2159   -0.5586    0.8982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0291   -0.2282    0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480   -0.4738   -0.5966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7685   -1.8122   -0.8441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807   -2.5301   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5961   -3.2597   -1.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -3.6846    0.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7343   -1.8399    0.6021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2865   -2.7083    0.5549 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9806   -0.4134    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0421    0.1152   -0.7215 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6422   -0.3535   -2.3558 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996    1.6015   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6081    2.2850    0.0628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2142    2.2184   -1.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414    3.4834   -2.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4508    4.2451   -1.7909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5873    3.9512   -3.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4423    3.2105   -3.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714    3.7187   -4.8203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6324    1.9257   -3.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761    1.4223   -2.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0665    0.0908   -1.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035   -0.6305   -2.3719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8392   -3.4674    2.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8588   -3.1067    0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827   -0.5926    3.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4706   -1.8161    4.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -0.3585    3.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506    0.5074    4.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8165    1.8956    2.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1076    1.3068    0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0447   -0.1694    1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922   -0.3347    0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055    2.7192    0.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950    1.8047   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045    2.1240    0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6801   -1.0530    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6874   -4.3554   -1.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0845   -3.2444   -2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6538   -2.9298   -1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2351   -3.9556    0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800   -3.3682    1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8438   -4.5985    0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3797   -1.9396    1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9544    0.1828    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0272   -0.2242   -0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0998    4.0023   -1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728    4.9577   -3.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1102    4.2241   -4.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570    1.3578   -3.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  1
 11 10  1  0
 10  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
 12 32  1  0
 32 33  2  0
 32 31  1  0
 31 30  2  0
 30 28  1  0
 28 29  1  0
 28 27  2  0
 27 25  1  0
 25 26  1  0
 25 24  2  0
 24 22  1  0
 22 23  2  0
 22 20  1  0
 20 21  1  6
 20 19  1  0
 19 17  1  0
 17 18  1  0
 17 14  1  0
 20 12  1  0
  7 10  1  0
 24 31  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 16 53  1  0
 10 47  1  6
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  6
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 30 60  1  0
 29 59  1  0
 27 58  1  0
 26 57  1  0
 19 55  1  0
 19 56  1  0
 17 54  1  1
M  END


  Mrv1652309052200112D          

 33 36  0  0  1  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    5.0013    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 Br  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
    4.8171    1.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7565    1.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    2.8579   -0.8250    0.0000 Cl  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
    2.1434   -1.2375    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   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
    1.4289    0.8250    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
    2.1434    2.0625    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0202870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)O[C@@]2(O[C@@H]3C(=C)CC[C@H](Br)C3(C)C)C(=O)C3=CC(O)=CC(O)=C3C(=O)C2(Cl)C[C@H]1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C24H27BrCl2O6/c1-11-6-7-15(25)21(2,3)20(11)32-24-18(30)13-8-12(28)9-14(29)17(13)19(31)23(24,27)10-16(26)22(4,5)33-24/h8-9,15-16,20,28-29H,1,6-7,10H2,2-5H3/t15-,16+,20+,23?,24-/m0/s1

> <INCHI_KEY>
UTARAOYMLWGJAB-FQIRZAPOSA-N

> <FORMULA>
C24H27BrCl2O6

> <MOLECULAR_WEIGHT>
562.28

> <EXACT_MASS>
560.036807

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
51.02156488459465

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,10aS)-10a-{[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione

> <JCHEM_LOGP>
6.685254128333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.776317990942072

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.137950197736543

> <JCHEM_PKA_STRONGEST_BASIC>
-4.144701363964011

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
128.38479999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,10aS)-10a-{[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3H,4H-naphtho[2,3-b]pyran-5,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6 Br   UNK     0      10.669   3.080   0.000  0.00  0.00          Br+0
HETATM    7  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.992   1.900   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.012   1.900   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.529   2.987   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.519   1.273   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       9.336  -0.770   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       5.335  -1.540   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20   32                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   12   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   24   32                                                  
CONECT   32   31   12   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₇BrCl₂O₆

Average Mass

562.2800 Da

Monoisotopic Mass

560.03681 Da

IUPAC Name

(3R,10aS)-10a-{[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione

Traditional Name

(3R,10aS)-10a-{[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3H,4H-naphtho[2,3-b]pyran-5,10-dione

CAS Registry Number

Not Available

SMILES

CC1(C)O[C@@]2(O[C@@H]3C(=C)CC[C@H](Br)C3(C)C)C(=O)C3=CC(O)=CC(O)=C3C(=O)C2(Cl)C[C@H]1Cl

InChI Identifier

InChI=1S/C24H27BrCl2O6/c1-11-6-7-15(25)21(2,3)20(11)32-24-18(30)13-8-12(28)9-14(29)17(13)19(31)23(24,27)10-16(26)22(4,5)33-24/h8-9,15-16,20,28-29H,1,6-7,10H2,2-5H3/t15-,16+,20+,23?,24-/m0/s1

InChI Key

UTARAOYMLWGJAB-FQIRZAPOSA-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

Not Available

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthoquinone
Naphthalene
Tetralin
Quinone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Pyranone
Oxane
Pyran
Benzenoid
Vinylogous acid
Alpha-haloketone
Alpha-chloroketone
Ketone
Oxacycle
Acetal
Hydrocarbon derivative
Organobromide
Organohalogen compound
Organic oxygen compound
Organochloride
Organooxygen compound
Organic oxide
Alkyl halide
Alkyl chloride
Aldehyde
Alkyl bromide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	6.69	ChemAxon
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	128.38 m³·mol⁻¹	ChemAxon
Polarizability	51.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

Not Available

Chemspider ID

2343098

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3086483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione (NP0202870)

MOL for NP0202870 ((3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D MOL for NP0202870 ((3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D SDF for NP0202870 ((3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D-SDF for NP0202870 ((3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

PDB for NP0202870 ((3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D PDB for NP0202870 ((3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

SMILES for NP0202870 ((3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

INCHI for NP0202870 ((3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

Structure for NP0202870 ((3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)

3D Structure for NP0202870 ((3r,10as)-10a-{[(1r,3s)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]oxy}-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3h,4h-naphtho[2,3-b]pyran-5,10-dione)