NP-MRD: Showing NP-Card for (1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol (NP0225440)

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Record Information

Version

2.0

Created at

2022-09-06 04:09:45 UTC

Updated at

2022-09-06 04:09:45 UTC

NP-MRD ID

NP0225440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062206092D          

 29 33  0  0  1  0            999 V2000
   -1.0607    2.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4309    1.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3455    2.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9753    1.6991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7517    1.9780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3815    1.4452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3645    1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698    0.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5576    0.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0628   -0.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8803   -0.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    0.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6872    0.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8821    1.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6304    2.1168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6420    2.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685    1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408    0.9416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3424    0.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0174    0.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7402   -0.0189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2760   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4839   -0.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585    0.3543    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2349    0.6333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0362    0.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8287    0.8872    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2742    0.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    1.0054    0.0000 O   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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 12 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  6  0  0  0
 24 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
M  END

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
   -6.0455    2.5744    2.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1910    1.6070    1.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9184    1.4018    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0824    0.4805    1.1751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8621    1.1399    0.8758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134    0.1268    0.7680 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5013    0.5929    0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803   -0.2461   -0.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580   -1.4354   -0.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8489   -2.1498   -1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249   -1.7422   -1.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5559   -0.5724   -1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6806    0.1595   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648    1.4242    0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3711    1.2268    1.1051 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3970    2.1374    2.1602 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5845    1.3186    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8574   -0.0583   -0.3273 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1834   -0.0738   -0.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9701   -0.3088   -1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3928   -1.8778   -0.4900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1284   -2.6030   -1.5797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6115   -2.1809   -1.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640   -1.2972   -0.2771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2360   -0.6028   -0.4681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0904    0.1145   -1.7440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6193   -0.3261    0.0486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2099    0.4201   -1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6839   -1.0830    0.6156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4531    3.3166    2.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5952    3.1707    1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7351    2.0897    3.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6129    1.0231    0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4532    1.9852    2.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7591   -0.2944    1.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0713   -0.5471    1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9020    0.5746    1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4752    1.6563    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -3.0714   -1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8139   -2.3243   -2.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2427    2.2041   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3562    1.8006    1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3173    0.2067    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7424    1.7354    2.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5223    2.0662   -0.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4493    1.5678    0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7015   -0.8439    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3285    0.6169   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9951    0.6405   -2.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3556   -1.0894   -2.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5538   -2.4045    0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0142   -3.6948   -1.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634   -2.4325   -2.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0432   -1.8435   -2.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1766   -3.1209   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4147   -1.9295    0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0310    0.2456   -2.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5004   -0.5364   -2.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5185    1.1344   -1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1464    1.5381   -0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039    0.2239   -2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2719    0.1051   -1.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8028   -1.9359    0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
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  8  9  2  0
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 18 19  1  0
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  9 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 24 27  1  0
 27 28  1  0
 27 29  1  1
 27  4  1  0
 25  6  1  0
 13  8  1  0
 25 21  1  0
 20 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  4 35  1  1
  6 36  1  1
  7 37  1  0
  7 38  1  0
 10 39  1  0
 11 40  1  0
 14 41  1  0
 14 42  1  0
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 16 44  1  0
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 21 51  1  1
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 24 56  1  1
 26 57  1  0
 26 58  1  0
 26 59  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
 29 63  1  0
M  END


  Mrv1652309062206092D          

 29 33  0  0  1  0            999 V2000
   -1.0607    2.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4309    1.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3455    2.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9753    1.6991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7517    1.9780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3815    1.4452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3645    1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698    0.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5576    0.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0628   -0.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8803   -0.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    0.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6872    0.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8821    1.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6304    2.1168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6420    2.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685    1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408    0.9416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3424    0.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0174    0.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7402   -0.0189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2760   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4839   -0.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585    0.3543    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2349    0.6333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0362    0.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8287    0.8872    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2742    0.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    1.0054    0.0000 O   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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 12 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  6  0  0  0
 24 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0225440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\[C@@H]1O[C@@H]2CC3=C(C=CC4=C3C[C@H](O)C[C@H](O)C4)[C@@H]3CC[C@@H]([C@@]23C)[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O4/c1-4-5-22-25(3,28)21-9-8-20-17-7-6-14-10-15(26)11-16(27)12-18(14)19(17)13-23(29-22)24(20,21)2/h4-7,15-16,20-23,26-28H,8-13H2,1-3H3/b5-4+/t15-,16-,20+,21+,22+,23-,24+,25-/m1/s1

> <INCHI_KEY>
IVFLABXZDZRHJH-LYVWAABPSA-N

> <FORMULA>
C25H34O4

> <MOLECULAR_WEIGHT>
398.543

> <EXACT_MASS>
398.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.5957165479975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,7R,9S,14R,16S,17R,18S,21S)-17,21-dimethyl-16-[(1E)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0^{2,12}.0^{5,11}.0^{18,21}]henicosa-2(12),3,5(11)-triene-7,9,17-triol

> <JCHEM_LOGP>
3.018100237333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.802370468077118

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.704673397101281

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7648510213599966

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
114.80269999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7R,9S,14R,16S,17R,18S,21S)-17,21-dimethyl-16-[(1E)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0^{2,12}.0^{5,11}.0^{18,21}]henicosa-2(12),3,5(11)-triene-7,9,17-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.980   4.640   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.804   3.646   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.645   4.166   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.821   3.172   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.270   3.692   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.445   2.698   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.280   2.816   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.224   1.598   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.641   0.173   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.584  -1.045   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.110  -0.837   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.693   0.589   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.749   1.806   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.113   3.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.510   3.951   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.532   5.491   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.888   3.264   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.209   1.758   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.706   1.394   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.232   0.567   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.115  -0.035   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.249  -1.308   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.770  -0.878   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.723   0.661   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.172   1.182   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.668   1.549   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.547   1.656   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.512   0.516   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.023   1.877   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12                                                       
CONECT   21    9   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   21    6   26                                             
CONECT   26   25                                                            
CONECT   27   24    4   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₄

Average Mass

398.5430 Da

Monoisotopic Mass

398.24571 Da

IUPAC Name

(1S,7R,9S,14R,16S,17R,18S,21S)-17,21-dimethyl-16-[(1E)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0^{2,12}.0^{5,11}.0^{18,21}]henicosa-2(12),3,5(11)-triene-7,9,17-triol

Traditional Name

(1S,7R,9S,14R,16S,17R,18S,21S)-17,21-dimethyl-16-[(1E)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0^{2,12}.0^{5,11}.0^{18,21}]henicosa-2(12),3,5(11)-triene-7,9,17-triol

CAS Registry Number

Not Available

SMILES

C\C=C\[C@@H]1O[C@@H]2CC3=C(C=CC4=C3C[C@H](O)C[C@H](O)C4)[C@@H]3CC[C@@H]([C@@]23C)[C@@]1(C)O

InChI Identifier

InChI=1S/C25H34O4/c1-4-5-22-25(3,28)21-9-8-20-17-7-6-14-10-15(26)11-16(27)12-18(14)19(17)13-23(29-22)24(20,21)2/h4-7,15-16,20-23,26-28H,8-13H2,1-3H3/b5-4+/t15-,16-,20+,21+,22+,23-,24+,25-/m1/s1

InChI Key

IVFLABXZDZRHJH-LYVWAABPSA-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
Iridoid-skeleton
Glycosyl compound
C-glycosyl compound
Tetralin
Naphthalene
Monoterpenoid
Aromatic monoterpenoid
Benzenoid
Pyran
Oxane
Tertiary alcohol
Secondary alcohol
Oxacycle
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	3.02	ChemAxon
pKa (Strongest Acidic)	13.7	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	114.8 m³·mol⁻¹	ChemAxon
Polarizability	46.6 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

58196872

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132542742

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol (NP0225440)

MOL for NP0225440 ((1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol)

3D MOL for NP0225440 ((1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol)

3D SDF for NP0225440 ((1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol)

3D-SDF for NP0225440 ((1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol)

PDB for NP0225440 ((1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol)

3D PDB for NP0225440 ((1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol)

SMILES for NP0225440 ((1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol)

INCHI for NP0225440 ((1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol)

Structure for NP0225440 ((1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol)

3D Structure for NP0225440 ((1s,7r,9s,14r,16s,17r,18s,21s)-17,21-dimethyl-16-[(1e)-prop-1-en-1-yl]-15-oxapentacyclo[12.6.1.0²,¹².0⁵,¹¹.0¹⁸,²¹]henicosa-2(12),3,5(11)-triene-7,9,17-triol)