NP-MRD: Showing NP-Card for 19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one (NP0320864)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 22:45:25 UTC

Updated at

2022-09-11 22:45:25 UTC

NP-MRD ID

NP0320864

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one

Description

Aflatrem belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Tremorgenic mycotoxins affect central nervous system activity and have been implicated in a number of neurologic diseases of cattle collectively known as "staggers syndromes". They cause a neurological disease of cattle known as "staggers syndrome". Aflatrem is an extremely weak basic (essentially neutral) compound (based on its pKa). Aflatrem is a potentially toxic compound. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors and hyperexcitability. Tremorgenic mycotoxins affect central nervous system activity. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. Tremorgenic mycotoxins affect central nervous system activity, inducing neurologic symptoms including mental confusion, paralysis, tremors, seizures, and death. Aflatrem is a tremorgenic mycotoxin that has been found in the fungus Aspergillus flavus. In addition, aflatrem inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241212362D          

 37 43  0  0  0  0            999 V2000
    0.8357   -1.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153   -0.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247    0.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2588    1.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792    1.9732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853    1.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545    0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4507    1.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332    2.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4212    2.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0268    1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1736    1.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5531    0.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8443    0.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0563    0.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -0.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0878   -0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4170    0.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7409    0.3602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8439   -0.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6655    0.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048    0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8784   -0.2986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7000   -0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3055   -0.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0935   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2760    0.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6704    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8824    0.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8529    1.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6575    1.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0483    1.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0354    2.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4298    2.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447    1.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958   -0.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 16 22  1  0  0  0  0
 15 23  1  0  0  0  0
 14 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
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
 25 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  2  0  0  0  0
  8 36  1  0  0  0  0
  2 37  1  0  0  0  0
M  END

     RDKit          3D

 76 82  0  0  0  0  0  0  0  0999 V2000
    5.3882    1.7360   -1.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014    1.7354   -0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3063    0.8238    0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6776    1.3448    0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5857   -0.5669   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4163    0.7046    1.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866    1.1515    2.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0831    1.1109    3.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068    0.6305    3.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3032    0.1746    2.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1215   -0.3506    2.3169 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1368   -0.6566    1.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -0.3099    0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1334    0.2264    1.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574   -0.6439   -0.9185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -0.7279   -1.3226 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5530    0.6535   -1.6948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170    0.8144   -1.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -0.4076   -1.3597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3875   -1.4490   -2.2526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0890   -0.1791   -1.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375    0.6369   -2.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0894    0.5207   -2.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081    1.0395   -3.4307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8378   -0.2686   -1.4009 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0401   -1.3610   -1.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9950   -0.7526   -0.2717 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3791   -1.7274    0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9469   -2.0597    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1327   -0.8538   -0.0028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3645    0.3078    0.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3312   -1.2371   -0.0921 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5071   -2.7359    0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6720    0.1978    0.5114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8196    0.5572   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7686    2.0441   -0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0739    0.2679    0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2330    1.0899   -2.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0486    2.3937   -2.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9705    2.3980   -0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3118    1.2633   -0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1162    0.6253    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6278    2.3744    1.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3618   -0.5649   -1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6224   -0.8975    0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9470   -1.3309    0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8934    1.5181    2.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5081    1.4725    4.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1557    0.5896    4.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227   -0.4903    2.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034    0.0969   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -1.6068   -1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602   -1.4385   -2.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1273    0.9249   -2.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048    1.3805   -0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0995    0.8313   -2.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    1.7569   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4093   -1.1438   -3.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0386    1.3621   -2.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8278   -0.5727   -1.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568   -2.6740    0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4268   -1.4010    1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0148   -2.7104   -0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5593   -2.6610    1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7557   -0.0507    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121    0.8741    1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0739    1.0599    0.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5730   -2.9695   -0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0992   -3.3251   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4312   -3.0046    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7027    2.3927   -0.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1787    2.2792   -1.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3532    2.5886    0.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9121    0.4465    1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4689   -0.7587    0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8343    1.0285    0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
  3  6  1  0
  6 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
 12 32  1  0
 32 33  1  6
 32 16  1  0
 16 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  1
 27 34  1  1
 34 35  1  0
 35 36  1  0
 35 37  1  0
  7  6  1  0
 30 32  1  0
 10 14  1  0
 30 19  1  0
 15 13  1  0
 27 21  1  0
 35 25  1  0
  4 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  5 46  1  0
  2 40  1  0
  1 38  1  0
  1 39  1  0
 11 50  1  0
  9 49  1  0
  8 48  1  0
  7 47  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
 16 53  1  6
 15 51  1  0
 15 52  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  0
 18 57  1  0
 20 58  1  0
 22 59  1  0
 25 60  1  6
 28 61  1  0
 28 62  1  0
 29 63  1  0
 29 64  1  0
 31 65  1  0
 31 66  1  0
 31 67  1  0
 36 71  1  0
 36 72  1  0
 36 73  1  0
 37 74  1  0
 37 75  1  0
 37 76  1  0
M  END


  Mrv0541 02241212362D          

 37 43  0  0  0  0            999 V2000
    0.8357   -1.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153   -0.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247    0.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2588    1.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792    1.9732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853    1.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545    0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4507    1.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332    2.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4212    2.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0268    1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1736    1.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5531    0.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8443    0.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0563    0.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -0.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0878   -0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4170    0.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7409    0.3602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8439   -0.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6655    0.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048    0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8784   -0.2986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7000   -0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3055   -0.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0935   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2760    0.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6704    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8824    0.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8529    1.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6575    1.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0483    1.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0354    2.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4298    2.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447    1.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1958   -0.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 16 22  1  0  0  0  0
 15 23  1  0  0  0  0
 14 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
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
 25 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  2  0  0  0  0
  8 36  1  0  0  0  0
  2 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320864

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)C1=C2C3=C(NC2=CC=C1)C1(C)C(C3)CCC2(O)C3=CC(=O)C4OC3(CCC12C)OC4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H39NO4/c1-8-27(2,3)20-10-9-11-21-24(20)19-16-18-12-13-31(35)23-17-22(34)26-28(4,5)37-32(23,36-26)15-14-29(31,6)30(18,7)25(19)33-21/h8-11,17-18,26,33,35H,1,12-16H2,2-7H3

> <INCHI_KEY>
YVDJBQQJIDPRKP-UHFFFAOYSA-N

> <FORMULA>
C32H39NO4

> <MOLECULAR_WEIGHT>
501.6564

> <EXACT_MASS>
501.287908741

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
57.18274768741751

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one

> <ALOGPS_LOGP>
6.06

> <JCHEM_LOGP>
6.052038274666668

> <ALOGPS_LOGS>
-6.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.788116584958473

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.617501355950719

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4033673277239957

> <JCHEM_POLAR_SURFACE_AREA>
71.55

> <JCHEM_REFRACTIVITY>
144.59510000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.94e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.560  -2.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.895  -0.587   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.913   1.028   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.350   2.587   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.268   3.683   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.893   2.998   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.955   1.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.441   2.236   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.782   3.738   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.253   4.194   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.383   3.148   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.917   3.288   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.524   1.873   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.366   0.858   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.043   1.646   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.572   1.190   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.249  -0.327   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.764  -0.797   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.512   0.187   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.250   0.672   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.442  -1.107   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.709   0.151   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.342   0.135   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      10.973  -0.557   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      12.507  -0.417   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.637  -1.463   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.108  -1.007   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.449   0.495   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.318   1.541   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.847   1.085   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.659   3.042   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.161   2.702   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.157   3.383   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.999   4.544   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.869   5.590   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.310   3.281   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.365  -0.410   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21   37                                             
CONECT    3    2    4   20                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9   16   36                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   30                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   11   16   23                                             
CONECT   16   15    8   17   22                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    7   20   21                                             
CONECT   20   19    3                                                       
CONECT   21   19    2                                                       
CONECT   22   16                                                            
CONECT   23   15                                                            
CONECT   24   14   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   13   25                                                  
CONECT   31   29   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35                                                       
CONECT   35   34                                                            
CONECT   36    8                                                            
CONECT   37    2                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₉NO₄

Average Mass

501.6564 Da

Monoisotopic Mass

501.28791 Da

IUPAC Name

19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one

Traditional Name

19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)C1=C2C3=C(NC2=CC=C1)C1(C)C(C3)CCC2(O)C3=CC(=O)C4OC3(CCC12C)OC4(C)C

InChI Identifier

InChI=1S/C32H39NO4/c1-8-27(2,3)20-10-9-11-21-24(20)19-16-18-12-13-31(35)23-17-22(34)26-28(4,5)37-32(23,36-26)15-14-29(31,6)30(18,7)25(19)33-21/h8-11,17-18,26,33,35H,1,12-16H2,2-7H3

InChI Key

YVDJBQQJIDPRKP-UHFFFAOYSA-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 naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
3-alkylindole
Indole
Indole or derivatives
Dihydropyranone
Ketal
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Meta-dioxolane
Cyclic alcohol
Ketone
Acetal
Oxacycle
Azacycle
Organooxygen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organonitrogen compound
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	6.06	ALOGPS
logP	6.05	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.55 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.6 m³·mol⁻¹	ChemAxon
Polarizability	57.18 Å³	ChemAxon
Number of Rings	7	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

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

107718

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one (NP0320864)

MOL for NP0320864 (19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one)

3D MOL for NP0320864 (19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one)

3D SDF for NP0320864 (19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one)

3D-SDF for NP0320864 (19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one)

PDB for NP0320864 (19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one)

3D PDB for NP0320864 (19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one)

SMILES for NP0320864 (19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one)

INCHI for NP0320864 (19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one)

Structure for NP0320864 (19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one)

3D Structure for NP0320864 (19-hydroxy-4,5,24,24-tetramethyl-12-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]hexacosa-6(14),8,10,12,20-pentaen-22-one)