NP-MRD: Showing NP-Card for lespecyrtin F1 (NP0034118)

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Record Information

Version

2.0

Created at

2021-06-20 17:56:22 UTC

Updated at

2021-06-30 00:04:18 UTC

NP-MRD ID

NP0034118

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lespecyrtin F1

Provided By

JEOL Database JEOL Logo

Description

15-(3-Methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2(7),3,5,11(16),12,14-heptaene-5,13,14-triol belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. lespecyrtin F1 is found in Lespedeza cyrtobotrya. lespecyrtin F1 was first documented in 2009 ( Mori-Hongo, M., et al.). Based on a literature review very few articles have been published on 15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-1(10),2(7),3,5,11(16),12,14-heptaene-5,13,14-triol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119563D          

 43 46  0  0  0  0            999 V2000
    3.8732   -3.4371    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -2.9223   -0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -3.6381   -2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -1.8984   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995   -1.2435   -1.6465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2197   -1.2392   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -2.3839   -1.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -3.6299   -1.4580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -2.3325   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084   -3.4805   -0.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9596   -1.1501   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1776    0.0149   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    1.3743    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048    2.0090   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628    1.1726   -0.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -0.0657   -0.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9787    3.4078    0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264    4.0561   -0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356    5.4266    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7547    6.1318    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5955    7.4695    0.7237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    5.4939    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    4.1241    0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046    3.5633    0.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1281   -1.4524    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0762    3.5049   -0.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684    5.9445   -0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278    7.8292    1.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131    6.0403    1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3806    2.0613   -0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8480    1.7196    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 25  1  0  0  0  0
 25 24  1  0  0  0  0
 20 22  2  0  0  0  0
 12 16  1  0  0  0  0
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 22 23  1  0  0  0  0
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 17 14  1  0  0  0  0
  2  3  1  0  0  0  0
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 11 37  1  0  0  0  0
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  3 29  1  0  0  0  0
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  3 31  1  0  0  0  0
M  END

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    3.8732   -3.4371    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -2.9223   -0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -3.6381   -2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -1.8984   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995   -1.2435   -1.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197   -1.2392   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -2.3839   -1.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -3.6299   -1.4580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -2.3325   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084   -3.4805   -0.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9596   -1.1501   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1776    0.0149   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    1.3743    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048    2.0090   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3356    5.4266    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9626    5.4939    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    4.1241    0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046    3.5633    0.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5326    2.1385    0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297   -3.3309   -0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1281   -1.4524    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2115   -1.7105   -2.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8480    1.7196    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 25  1  0
 25 24  1  0
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  4  2  2  3
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 17 14  1  0
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  3 31  1  0
M  END


  Mrv1652306202119563D          

 43 46  0  0  0  0            999 V2000
    3.8732   -3.4371    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -2.9223   -0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -3.6381   -2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -1.8984   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995   -1.2435   -1.6465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2197   -1.2392   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -2.3839   -1.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -3.6299   -1.4580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -2.3325   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084   -3.4805   -0.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9596   -1.1501   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3841    1.3743    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048    2.0090   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628    1.1726   -0.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9787    3.4078    0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264    4.0561   -0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356    5.4266    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7547    6.1318    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5955    7.4695    0.7237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    5.4939    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    4.1241    0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046    3.5633    0.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1281   -1.4524    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8480    1.7196    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 25  1  0  0  0  0
 25 24  1  0  0  0  0
 20 22  2  0  0  0  0
 12 16  1  0  0  0  0
 16  6  2  0  0  0  0
 22 23  1  0  0  0  0
  7  9  2  0  0  0  0
 19 20  1  0  0  0  0
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  7  8  1  0  0  0  0
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  6  5  1  0  0  0  0
 17 18  1  0  0  0  0
  5  4  1  0  0  0  0
 18 19  2  0  0  0  0
  4  2  2  3  0  0  0
 23 24  1  0  0  0  0
  2  1  1  0  0  0  0
 17 14  1  0  0  0  0
  2  3  1  0  0  0  0
 18 38  1  0  0  0  0
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 25 43  1  0  0  0  0
 11 37  1  0  0  0  0
  8 35  1  0  0  0  0
 21 40  1  0  0  0  0
 10 36  1  0  0  0  0
  5 33  1  0  0  0  0
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  4 32  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034118

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C([H])=C1[H])C1=C(C3=C([H])C(O[H])=C(O[H])C(=C3O1)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])O2

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O5/c1-10(2)3-5-13-18(23)16(22)8-14-15-9-24-17-7-11(21)4-6-12(17)19(15)25-20(13)14/h3-4,6-8,21-23H,5,9H2,1-2H3

> <INCHI_KEY>
FRLCRXOQCLBSAQ-UHFFFAOYSA-N

> <FORMULA>
C20H18O5

> <MOLECULAR_WEIGHT>
338.359

> <EXACT_MASS>
338.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
37.081945758679495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11,13,15-heptaene-5,13,14-triol

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
4.111022772333335

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.025011549666777

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.113457735924111

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8789502882224185

> <JCHEM_POLAR_SURFACE_AREA>
83.06

> <JCHEM_REFRACTIVITY>
95.11609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11,13,15-heptaene-5,13,14-triol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    3.8732   -3.4371    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -2.9223   -0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -3.6381   -2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -1.8984   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995   -1.2435   -1.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197   -1.2392   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -2.3839   -1.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -3.6299   -1.4580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -2.3325   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084   -3.4805   -0.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9596   -1.1501   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1776    0.0149   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    1.3743    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048    2.0090   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628    1.1726   -0.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -0.0657   -0.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9787    3.4078    0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264    4.0561   -0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356    5.4266    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7547    6.1318    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5955    7.4695    0.7237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    5.4939    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    4.1241    0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046    3.5633    0.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5326    2.1385    0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297   -3.3309   -0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6651   -4.4959    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7123   -2.8976    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9382   -4.6976   -2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2376   -3.5655   -2.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5799   -3.2391   -3.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1281   -1.4524    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2115   -1.7105   -2.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5431   -0.2140   -1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -3.6045   -1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026   -4.1680   -0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -1.1439    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0762    3.5049   -0.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684    5.9445   -0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278    7.8292    1.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131    6.0403    1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3806    2.0613   -0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8480    1.7196    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 25  1  0
 25 24  1  0
 20 22  2  0
 12 16  1  0
 16  6  2  0
 22 23  1  0
  7  9  2  0
 19 20  1  0
  9 11  1  0
 11 12  2  0
  7  6  1  0
 13 12  1  0
 13 14  2  0
 20 21  1  0
  7  8  1  0
 23 17  2  0
 15 16  1  0
  9 10  1  0
 14 15  1  0
  6  5  1  0
 17 18  1  0
  5  4  1  0
 18 19  2  0
  4  2  2  3
 23 24  1  0
  2  1  1  0
 17 14  1  0
  2  3  1  0
 18 38  1  0
 22 41  1  0
 19 39  1  0
 25 42  1  0
 25 43  1  0
 11 37  1  0
  8 35  1  0
 21 40  1  0
 10 36  1  0
  5 33  1  0
  5 34  1  0
  4 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.873  -3.437   0.218  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.998  -2.922  -0.897  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.192  -3.638  -2.206  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.148  -1.898  -0.678  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.200  -1.244  -1.647  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.220  -1.239  -1.146  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.034  -2.384  -1.090  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.583  -3.630  -1.458  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.363  -2.333  -0.654  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.108  -3.481  -0.636  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.960  -1.150  -0.229  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.178   0.015  -0.250  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.384   1.374   0.089  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.205   2.009  -0.172  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.263   1.173  -0.650  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.854  -0.066  -0.702  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.979   3.408   0.034  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.226   4.056  -0.237  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.336   5.427   0.003  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.755   6.132   0.507  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.596   7.470   0.724  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.963   5.494   0.781  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.079   4.124   0.544  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.305   3.563   0.840  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.533   2.139   0.618  0.00  0.00           C+0
HETATM   26  H   UNK     0       4.930  -3.331  -0.049  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.665  -4.496   0.404  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.712  -2.898   1.157  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.938  -4.698  -2.094  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.238  -3.566  -2.523  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.580  -3.239  -3.017  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.128  -1.452   0.319  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.212  -1.710  -2.635  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.543  -0.214  -1.805  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.389  -3.604  -1.488  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.503  -4.168  -0.980  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.991  -1.144   0.107  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.076   3.505  -0.630  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.268   5.944  -0.203  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.428   7.829   1.073  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.813   6.040   1.174  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.381   2.061  -0.071  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.848   1.720   1.580  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   29   30   31                                             
CONECT    4    5    2   32                                                  
CONECT    5    6    4   33   34                                             
CONECT    6   16    7    5                                                  
CONECT    7    9    6    8                                                  
CONECT    8    7   35                                                       
CONECT    9    7   11   10                                                  
CONECT   10    9   36                                                       
CONECT   11    9   12   37                                                  
CONECT   12   16   11   13                                                  
CONECT   13   25   12   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   16   14                                                       
CONECT   16   12    6   15                                                  
CONECT   17   23   18   14                                                  
CONECT   18   17   19   38                                                  
CONECT   19   20   18   39                                                  
CONECT   20   22   19   21                                                  
CONECT   21   20   40                                                       
CONECT   22   20   23   41                                                  
CONECT   23   22   17   24                                                  
CONECT   24   25   23                                                       
CONECT   25   13   24   42   43                                             
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    8                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
CONECT   42   25                                                            
CONECT   43   25                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

RDKit          3D

43 46  0  0  0  0  0  0  0  0999 V2000
    3.8732   -3.4371    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -2.9223   -0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -3.6381   -2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -1.8984   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1995   -1.2435   -1.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197   -1.2392   -1.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -2.3839   -1.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -3.6299   -1.4580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -2.3325   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084   -3.4805   -0.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9596   -1.1501   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1776    0.0149   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    1.3743    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048    2.0090   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628    1.1726   -0.6501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -0.0657   -0.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9787    3.4078    0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2264    4.0561   -0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356    5.4266    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7547    6.1318    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5955    7.4695    0.7237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626    5.4939    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0790    4.1241    0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046    3.5633    0.8396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5326    2.1385    0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297   -3.3309   -0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6651   -4.4959    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7123   -2.8976    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9382   -4.6976   -2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2376   -3.5655   -2.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5799   -3.2391   -3.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1281   -1.4524    0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2115   -1.7105   -2.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5431   -0.2140   -1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -3.6045   -1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026   -4.1680   -0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -1.1439    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0762    3.5049   -0.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684    5.9445   -0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278    7.8292    1.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131    6.0403    1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3806    2.0613   -0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8480    1.7196    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 25  1  0
 25 24  1  0
 20 22  2  0
 12 16  1  0
 16  6  2  0
 22 23  1  0
  7  9  2  0
 19 20  1  0
  9 11  1  0
 11 12  2  0
  7  6  1  0
 13 12  1  0
 13 14  2  0
 20 21  1  0
  7  8  1  0
 23 17  2  0
 15 16  1  0
  9 10  1  0
 14 15  1  0
  6  5  1  0
 17 18  1  0
  5  4  1  0
 18 19  2  0
  4  2  2  3
 23 24  1  0
  2  1  1  0
 17 14  1  0
  2  3  1  0
 18 38  1  0
 22 41  1  0
 19 39  1  0
 25 42  1  0
 25 43  1  0
 11 37  1  0
  8 35  1  0
 21 40  1  0
 10 36  1  0
  5 33  1  0
  5 34  1  0
  4 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₅

Average Mass

338.3590 Da

Monoisotopic Mass

338.11542 Da

IUPAC Name

15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11,13,15-heptaene-5,13,14-triol

Traditional Name

15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11,13,15-heptaene-5,13,14-triol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C([H])=C1[H])C1=C(C3=C([H])C(O[H])=C(O[H])C(=C3O1)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])O2

InChI Identifier

InChI=1S/C20H18O5/c1-10(2)3-5-13-18(23)16(22)8-14-15-9-24-17-7-11(21)4-6-12(17)19(15)25-20(13)14/h3-4,6-8,21-23H,5,9H2,1-2H3

InChI Key

FRLCRXOQCLBSAQ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lespedeza cyrtobotrya	JEOL database	Mori-Hongo, M., et al, J. Nat. Prod. 72, 63 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Benzopyran
1-benzopyran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Ether
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	3.76	ALOGPS
logP	4.11	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.12 m³·mol⁻¹	ChemAxon
Polarizability	37.08 Å³	ChemAxon
Number of Rings	4	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

C00047280

Chemspider ID

24619507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25208435

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mori-Hongo, M., et al. (2009). Mori-Hongo, M., et al, J. Nat. Prod. 72, 63 (2009). J. Nat. Prod..

Showing NP-Card for lespecyrtin F1 (NP0034118)

MOL for NP0034118 (lespecyrtin F1)

3D MOL for NP0034118 (lespecyrtin F1)

3D SDF for NP0034118 (lespecyrtin F1)

3D-SDF for NP0034118 (lespecyrtin F1)

PDB for NP0034118 (lespecyrtin F1)

3D PDB for NP0034118 (lespecyrtin F1)

SMILES for NP0034118 (lespecyrtin F1)

INCHI for NP0034118 (lespecyrtin F1)

Structure for NP0034118 (lespecyrtin F1)

3D Structure for NP0034118 (lespecyrtin F1)