NP-MRD: Showing NP-Card for (8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione (NP0059865)

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Record Information

Version

2.0

Created at

2022-04-28 05:01:28 UTC

Updated at

2022-04-28 05:01:28 UTC

NP-MRD ID

NP0059865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione

Description

Tephrodin belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. Thus, tephrodin is considered to be a flavonoid. (8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione is found in Tephrosia polystachyoides. Based on a literature review very few articles have been published on Tephrodin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207012D          

 33 37  0  0  1  0            999 V2000
    4.7465   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0516    0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -0.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2815   -1.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9764   -1.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7089   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4038   -1.6804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3662   -2.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489   -1.5502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8916   -0.2814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6241    0.0981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4896    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    1.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739    1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3043    0.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7028    1.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9836    1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3130    0.5521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642    1.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847    2.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9531    1.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892    0.8571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167    0.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1740   -0.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8593    2.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644    2.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2020    3.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9345    3.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295    3.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919    2.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  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
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  6  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 12 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  2 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
  1 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    1.2106    5.8802    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000    4.6054    0.4387 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081    3.4703    0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    3.6034    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468    2.5038    0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585    1.1953   -0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7333    1.1101   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3572   -0.0056   -0.2552 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622   -0.1590   -0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3706   -1.4166   -0.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6451   -1.5929    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3602   -2.7744   -0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7877   -3.7899   -0.9020 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5155   -3.6336   -1.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8204   -2.4446   -1.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5101    0.9516   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9251    2.1658    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242    3.2204    0.3090 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5459    2.2243    0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5903    0.1258   -0.2796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4023   -1.0694   -0.8617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473   -2.2129   -0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816   -3.3780   -1.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0616   -2.3538    0.3607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2228   -0.1841    1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7248    0.0516    2.1773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5039   -0.7995    0.7940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4856   -2.3224    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6364   -0.4495    1.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8175   -0.4084   -0.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9448    0.6634   -0.8153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4266    1.7621    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4909    2.7902   -0.0056 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0109    6.6129    0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744    6.1043   -0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    5.8071    1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7783    4.6102    0.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1425   -0.8237    0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3587   -2.8949    0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3228   -4.7291   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0737   -4.4435   -1.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8452   -2.4117   -1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5869    0.8584   -0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8156   -3.0189   -2.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965   -3.9680   -1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0782   -4.0144   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6675   -2.7628    1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4903   -2.6689    1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4921   -2.7039   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2326   -0.1146    2.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3876    0.2264    1.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2390   -1.3715    2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8546    0.9049   -1.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3665    1.4328    1.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    2.0398   -0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 19  2  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5 33  1  0
 33 32  1  0
 32 31  1  0
 31 30  1  0
 30 27  1  0
 27 28  1  6
 27 29  1  0
 27 25  1  0
 25 26  2  0
 25 20  1  0
 20 21  1  6
 21 22  1  0
 22 23  1  0
 22 24  2  0
  5  4  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4  3  1  0
 15 10  1  0
  7 19  1  0
 20  6  1  0
 20 31  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 16 43  1  0
 32 54  1  0
 32 55  1  0
 31 53  1  6
 28 47  1  0
 28 48  1  0
 28 49  1  0
 29 50  1  0
 29 51  1  0
 29 52  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
  4 37  1  0
 11 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
M  END


  Mrv1652304282207012D          

 33 37  0  0  1  0            999 V2000
    4.7465   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0516    0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -0.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2815   -1.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9764   -1.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7089   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4038   -1.6804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3662   -2.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489   -1.5502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8916   -0.2814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6241    0.0981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4896    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    1.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739    1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3043    0.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7028    1.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9836    1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3130    0.5521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642    1.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847    2.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9531    1.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892    0.8571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167    0.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1740   -0.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8593    2.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644    2.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2020    3.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9345    3.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295    3.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919    2.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  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
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  6  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 12 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  2 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
  1 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0059865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)C=C(OC2=C2C(OC[C@@H]3OC(C)(C)C(=O)[C@]23OC(C)=O)=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O8/c1-13(26)32-25-19(33-24(2,3)23(25)28)12-30-18-11-17(29-4)20-15(27)10-16(31-22(20)21(18)25)14-8-6-5-7-9-14/h5-11,19H,12H2,1-4H3/t19-,25+/m0/s1

> <INCHI_KEY>
WIYBTPVLDULURO-UQBPGWFLSA-N

> <FORMULA>
C25H22O8

> <MOLECULAR_WEIGHT>
450.443

> <EXACT_MASS>
450.131467668

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.37705818523743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(13S,17S)-8-methoxy-15,15-dimethyl-6,16-dioxo-4-phenyl-3,11,14-trioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1,4,7,9-tetraen-17-yl acetate

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.9654670296666663

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.28780863706568

> <JCHEM_PKA_STRONGEST_BASIC>
-4.089844759458501

> <JCHEM_POLAR_SURFACE_AREA>
97.36000000000001

> <JCHEM_REFRACTIVITY>
116.60349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(13S,17S)-8-methoxy-15,15-dimethyl-6,16-dioxo-4-phenyl-3,11,14-trioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1,4,7,9-tetraen-17-yl acetate

> <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       8.860  -0.768   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.563   0.062   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.196  -0.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.125  -2.185   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.423  -3.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.790  -2.307   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.087  -3.137   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.017  -4.675   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.758  -2.894   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.461  -2.064   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.531  -0.525   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.898   0.183   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.647   1.703   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.337   3.079   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.125   1.933   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.435   0.556   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.179   3.472   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.836   2.777   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.184   1.031   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.093   2.568   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.385   3.935   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.379   3.415   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.633   1.600   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.001   2.308   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.298   1.478   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.228  -0.060   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.525  -0.890   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.071   3.847   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.774   4.677   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.844   6.215   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.211   6.924   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.508   6.094   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.438   4.555   0.000  0.00  0.00           C+0
CONECT    1    2    6   26                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11    3   13   19                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   18                                             
CONECT   16   15   11                                                       
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   12   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    2   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25    1   27                                                  
CONECT   27   26                                                            
CONECT   28   24   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₂O₈

Average Mass

450.4430 Da

Monoisotopic Mass

450.13147 Da

IUPAC Name

(13S,17S)-8-methoxy-15,15-dimethyl-6,16-dioxo-4-phenyl-3,11,14-trioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1,4,7,9-tetraen-17-yl acetate

Traditional Name

(13S,17S)-8-methoxy-15,15-dimethyl-6,16-dioxo-4-phenyl-3,11,14-trioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1,4,7,9-tetraen-17-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)C=C(OC2=C2C(OC[C@@H]3OC(C)(C)C(=O)[C@]23OC(C)=O)=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C25H22O8/c1-13(26)32-25-19(33-24(2,3)23(25)28)12-30-18-11-17(29-4)20-15(27)10-16(31-22(20)21(18)25)14-8-6-5-7-9-14/h5-11,19H,12H2,1-4H3/t19-,25+/m0/s1

InChI Key

WIYBTPVLDULURO-UQBPGWFLSA-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
Tephrosia polystachyoides	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

8-prenylated flavones

Alternative Parents

Substituents

8-prenylated flavone
Pyranoflavonoid
5-methoxyflavonoid-skeleton
Pyranochromene
Chromone
Benzopyran
Chromane
1-benzopyran
Furopyran
Anisole
Alkyl aryl ether
Pyranone
Alpha-acyloxy ketone
Benzenoid
Pyran
3-furanone
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous ester
Tetrahydrofuran
Furan
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110161 )

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	2.83	ALOGPS
logP	2.97	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	15.29	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	97.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.6 m³·mol⁻¹	ChemAxon
Polarizability	45.38 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00013472

Chemspider ID

24843231

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257635

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione (NP0059865)

MOL for NP0059865 ((8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione)

3D MOL for NP0059865 ((8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione)

3D SDF for NP0059865 ((8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione)

3D-SDF for NP0059865 ((8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione)

PDB for NP0059865 ((8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione)

3D PDB for NP0059865 ((8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione)

SMILES for NP0059865 ((8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione)

INCHI for NP0059865 ((8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione)

Structure for NP0059865 ((8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione)

3D Structure for NP0059865 ((8aR,11aR)-rel-(-)-11a-(Acetyloxy)-8a,11a-dihydro-5-methoxy-10,10-dimethyl-2-phenyl-4H,8H-furo[3,2-d]benzo[1,2-b:3,4-b']dipyran-4,11(10H)-dione)