NP-MRD: Showing NP-Card for (2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione (NP0174740)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 12:02:57 UTC

Updated at

2022-09-03 12:02:57 UTC

NP-MRD ID

NP0174740

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione

Description

Retipolide E belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. (2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione is found in Retiboletus ornatipes. Based on a literature review very few articles have been published on Retipolide E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032214022D          

 34 38  0  0  1  0            999 V2000
    8.8299    0.9884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1860    1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3902    1.2865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9373    1.9761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9734    1.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4513    0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8857    1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0738    0.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7533    0.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3104   -0.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1462   -0.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9586    0.4817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513    1.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8583    1.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187    2.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7954    2.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2478    2.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5324    1.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9768    0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437    3.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476    3.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8767    3.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5524    2.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7526    2.9424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4531    2.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2354    3.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4375    3.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2198    4.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8001    5.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5824    5.8030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5981    4.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8157    4.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2249    2.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9144    2.7813    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  9 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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  2  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
 25 33  2  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
   -1.2773    3.7753   -2.0541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4622    2.5877   -1.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638    1.4936   -1.7452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049    0.3957   -1.0806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2819   -0.6797   -2.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1685   -1.1811   -2.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285   -0.2396   -2.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4475   -0.3637   -2.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8428   -1.4453   -2.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0476   -2.3896   -1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6210   -2.2771   -1.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3285   -1.4930   -1.6363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3143   -0.8158   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5561    0.3025   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5259    0.7915    1.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2900    0.1272    2.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0762   -0.9858    1.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586   -1.4617    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8425   -2.5836    0.4140 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6007    1.8137    1.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1467    1.7234    1.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985    0.8132    0.4196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1941    0.0463   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381   -1.1641    0.4207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4601    0.8208   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5236    0.1913    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8583    0.8127    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8637    0.3484    2.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5894   -0.7791    1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6072   -1.2350    2.7621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2702   -1.4012    0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416   -0.9076   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009    2.1299   -0.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6603    2.9792   -0.4710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604   -1.3855   -1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7663   -0.2017   -3.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9343    0.6634   -3.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0306    0.4490   -3.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2218   -3.3663   -1.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1247   -3.1896   -1.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184    0.9584   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.4829    3.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6585   -1.4628    2.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3807   -3.0285    1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5378    1.6014    2.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9164    2.8486    1.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9018    2.7958    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5313    1.6165    2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2945    1.7001    1.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1099    0.8422    3.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5546   -0.9442    2.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8379   -2.2757    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0678   -1.4339   -0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738    3.5802    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 33  1  0
 33 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 25  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  9 10  1  0
 10 11  2  0
  4  3  1  6
  3  2  1  0
  2  1  2  0
  2 33  1  0
 32 26  1  0
 23  4  1  0
 11  6  1  0
 18 13  1  0
 34 54  1  0
 27 49  1  0
 28 50  1  0
 30 51  1  0
 31 52  1  0
 32 53  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  8 38  1  0
 14 41  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 10 39  1  0
 11 40  1  0
M  END


  Mrv1652309032214022D          

 34 38  0  0  1  0            999 V2000
    8.8299    0.9884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1860    1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3902    1.2865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9373    1.9761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9734    1.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4513    0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8857    1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0738    0.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7533    0.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3104   -0.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1462   -0.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9586    0.4817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513    1.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8583    1.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6187    2.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7954    2.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2478    2.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5324    1.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9768    0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437    3.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476    3.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8767    3.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5524    2.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7526    2.9424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4531    2.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2354    3.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4375    3.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2198    4.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8001    5.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5824    5.8030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5981    4.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8157    4.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2249    2.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9144    2.7813    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  9 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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  2  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
 25 33  2  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0174740

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(C2=CC=C(O)C=C2)[C@@]2(CC3=CC=C(OC4=CC(CCOC2=O)=CC=C4O)C=C3)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H20O8/c27-18-6-4-17(5-7-18)22-23(29)24(30)34-26(22)14-16-1-8-19(9-2-16)33-21-13-15(3-10-20(21)28)11-12-32-25(26)31/h1-10,13,27-29H,11-12,14H2/t26-/m1/s1

> <INCHI_KEY>
ZEWUQXZTPTVEAO-AREMUKBSSA-N

> <FORMULA>
C26H20O8

> <MOLECULAR_WEIGHT>
460.438

> <EXACT_MASS>
460.115817604

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.33527841812063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-5H-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1^{3,7}]nonadecane]-1'(16'),3',5',7'(19'),14',17'-hexaene-5,11'-dione

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
4.3918274366666665

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.72817249499433

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.14643313908109

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3432502922985226

> <JCHEM_POLAR_SURFACE_AREA>
122.52

> <JCHEM_REFRACTIVITY>
121.03529999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1^{3,7}]nonadecane]-1'(16'),3',5',7'(19'),14',17'-hexaene-5,11'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0      16.482   1.845   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      15.281   2.808   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.795   2.402   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.950   3.689   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.017   2.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.042   0.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.987   1.921   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.471   1.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.873   0.225   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.913  -0.982   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.473  -0.689   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.389   0.899   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.256   2.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.202   3.325   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.755   4.829   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.218   5.115   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.196   3.945   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.727   2.472   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.690   1.334   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.922   5.899   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.422   6.368   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.970   6.071   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.231   5.115   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.738   5.493   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.913   4.891   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.506   6.376   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.017   6.767   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.610   8.252   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.693   9.347   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.287  10.832   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.183   8.956   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.589   7.471   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.353   4.346   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      16.640   5.192   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23   25                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    4   24                                                  
CONECT   24   23                                                            
CONECT   25    4   26   33                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26                                                       
CONECT   33   25    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₀O₈

Average Mass

460.4380 Da

Monoisotopic Mass

460.11582 Da

IUPAC Name

(2R)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-5H-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1^{3,7}]nonadecane]-1'(16'),3',5',7'(19'),14',17'-hexaene-5,11'-dione

Traditional Name

(2R)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1^{3,7}]nonadecane]-1'(16'),3',5',7'(19'),14',17'-hexaene-5,11'-dione

CAS Registry Number

Not Available

SMILES

OC1=C(C2=CC=C(O)C=C2)[C@@]2(CC3=CC=C(OC4=CC(CCOC2=O)=CC=C4O)C=C3)OC1=O

InChI Identifier

InChI=1S/C26H20O8/c27-18-6-4-17(5-7-18)22-23(29)24(30)34-26(22)14-16-1-8-19(9-2-16)33-21-13-15(3-10-20(21)28)11-12-32-25(26)31/h1-10,13,27-29H,11-12,14H2/t26-/m1/s1

InChI Key

ZEWUQXZTPTVEAO-AREMUKBSSA-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

Species Name	Source	Reference
Retiboletus ornatipes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
2-furanone
Dicarboxylic acid or derivatives
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Enol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	3.52	ALOGPS
logP	4.39	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8.15	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	121.04 m³·mol⁻¹	ChemAxon
Polarizability	44.34 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

Not Available

Chemspider ID

28284231

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134845172

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione (NP0174740)

MOL for NP0174740 ((2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione)

3D MOL for NP0174740 ((2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione)

3D SDF for NP0174740 ((2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione)

3D-SDF for NP0174740 ((2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione)

PDB for NP0174740 ((2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione)

3D PDB for NP0174740 ((2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione)

SMILES for NP0174740 ((2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione)

INCHI for NP0174740 ((2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione)

Structure for NP0174740 ((2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione)

3D Structure for NP0174740 ((2r)-4,4'-dihydroxy-3-(4-hydroxyphenyl)-2',10'-dioxaspiro[furan-2,12'-tricyclo[12.2.2.1³,⁷]nonadecane]-1'(16'),3'(19'),4',6',14',17'-hexaene-5,11'-dione)