NP-MRD: Showing NP-Card for (1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol (NP0148325)

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Record Information

Version

1.0

Created at

2022-09-02 04:04:02 UTC

Updated at

2022-09-02 04:04:02 UTC

NP-MRD ID

NP0148325

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol

Description

Blazeispirol E 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. (1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol is found in Agaricus blazei. It was first documented in 2002 (PMID: 11853754). Based on a literature review a significant number of articles have been published on Blazeispirol E (PMID: 36049892) (PMID: 36049891) (PMID: 36049888) (PMID: 36049887) (PMID: 36049886) (PMID: 36049885).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206042D          

 30 34  0  0  1  0            999 V2000
    5.5132   -0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9812    0.2913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691    0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8891   -0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770   -0.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450   -0.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250    0.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6371    0.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172    1.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293    1.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2930    1.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3645    1.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009    0.3401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7182   -0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136    0.6945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3534   -0.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -0.2905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1387    0.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453    1.0947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4878    1.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1536    2.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995    2.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036    2.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227    1.8829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6064    2.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703    1.0975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0575    0.4317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9331    1.2393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7110    2.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
  6 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  1  0  0  0
 20 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    5.4710    3.6254    1.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2516    2.4068    0.7182 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    1.7348    0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8997    2.2085    1.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179    1.4791    1.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6408    0.2749    0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8244   -0.2234   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0043    0.4862    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3226    0.0487   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8752    1.0103   -1.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961   -1.6129   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440   -2.4123   -0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6182   -1.9379    0.2399 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5693   -2.5333    1.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5663   -2.3892   -0.5981 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4076   -1.4684   -1.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -0.2470   -1.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133   -0.4599    0.2223 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6869   -0.0958    0.9209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9015   -0.5457    0.4096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1850    0.1579   -0.7442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8989    1.2830   -0.4604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515    2.4156    0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5185    1.8079   -1.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9465    0.7292    0.5195 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9487    0.0075   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368   -0.2008    1.3262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7295   -1.3294    1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8309   -2.0222    0.1721 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9736   -2.5574   -0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3244    4.4025    0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5069    3.7615    1.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7282    3.8732    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9022    3.1506    1.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385    1.8899    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0957   -0.7899   -1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0023   -0.3884    0.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3534    1.1913   -2.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -2.0076   -0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9060   -3.4296   -0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5218   -2.2444    2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6077   -3.6310    1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2246   -2.1906    2.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5192   -3.4300   -0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2965   -2.0371   -2.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497   -1.3691   -2.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551    0.7329   -1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2970   -0.2157   -1.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1609    2.1641    0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0299    3.2928   -0.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7535    2.7770    1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9220    2.6978   -2.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4525    1.0692   -2.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5745    2.0818   -1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3783    1.5150    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8467    0.6839   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5922   -0.1545   -1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502   -0.9090    0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7044    0.3986    2.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401   -1.5985    2.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8402   -2.5746    1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8889   -2.7607   -0.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6131   -3.5832   -0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1229   -2.0083   -1.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  1
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 16 17  1  0
 17 18  1  0
 18 19  1  1
 20 19  1  1
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 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 20 29  1  0
 29 30  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8  3  1  0
 18  6  1  0
 27 20  1  0
 18 13  1  0
 29 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
 11 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  6
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
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 25 55  1  1
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 26 57  1  0
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 27 59  1  1
 28 60  1  0
 29 61  1  1
 30 62  1  0
 30 63  1  0
 30 64  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
M  END


  Mrv1652309022206042D          

 30 34  0  0  1  0            999 V2000
    5.5132   -0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9812    0.2913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691    0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8891   -0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770   -0.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450   -0.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250    0.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6371    0.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172    1.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293    1.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2930    1.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3645    1.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009    0.3401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7182   -0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136    0.6945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3534   -0.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -0.2905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1387    0.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453    1.0947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4878    1.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1536    2.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995    2.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036    2.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227    1.8829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6064    2.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703    1.0975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0575    0.4317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9331    1.2393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7110    2.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
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 15 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0148325

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(C=C[C@]3(C)[C@@H]4CC[C@]23O[C@@]2(OC(C)(C)[C@@H](C)[C@H]2O)[C@H]4C)=C1CO

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O5/c1-14-18-10-12-24(30-25(14)21(27)15(2)22(3,4)29-25)19-7-8-20(28-6)17(13-26)16(19)9-11-23(18,24)5/h7-9,11,14-15,18,21,26-27H,10,12-13H2,1-6H3/t14-,15-,18+,21+,23+,24-,25-/m0/s1

> <INCHI_KEY>
ZZLUANSADFHKRE-OFDNLDAYSA-N

> <FORMULA>
C25H34O5

> <MOLECULAR_WEIGHT>
414.542

> <EXACT_MASS>
414.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.48891554936864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2S,3R,4S,10'R,11'R,12'S)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0^{1,10}.0^{2,7}]hexadecane]-2',4',6',8'-tetraen-3-ol

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
3.7278125506666666

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.590352950834621

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.948614290037536

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9824713594557233

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
115.99709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,3R,4S,10'R,11'R,12'S)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0^{1,10}.0^{2,7}]hexadecane]-2',4',6',8'-tetraen-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.291  -0.633   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.298   0.544   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.782   0.272   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.260  -1.176   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.744  -1.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.751  -0.271   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.273   1.178   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.789   1.449   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.312   2.898   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.828   3.169   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.280   2.355   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.547   2.097   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.242   0.635   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.341  -0.614   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.585   1.296   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.660  -0.242   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.909  -1.143   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.235  -0.542   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.992   0.690   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.258   2.043   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.777   3.507   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.020   4.416   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.986   5.557   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.047   5.564   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.269   3.515   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.732   3.996   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.798   2.049   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.707   0.806   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.742   2.313   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.327   3.797   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   18                                             
CONECT   14   13                                                            
CONECT   15   13   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    6   13   19                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   27   29                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28                                                  
CONECT   28   27                                                            
CONECT   29   20   15   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₅

Average Mass

414.5420 Da

Monoisotopic Mass

414.24062 Da

IUPAC Name

(1'R,2S,3R,4S,10'R,11'R,12'S)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0^{1,10}.0^{2,7}]hexadecane]-2',4',6',8'-tetraen-3-ol

Traditional Name

(1'R,2S,3R,4S,10'R,11'R,12'S)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0^{1,10}.0^{2,7}]hexadecane]-2',4',6',8'-tetraen-3-ol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(C=C[C@]3(C)[C@@H]4CC[C@]23O[C@@]2(OC(C)(C)[C@@H](C)[C@H]2O)[C@H]4C)=C1CO

InChI Identifier

InChI=1S/C25H34O5/c1-14-18-10-12-24(30-25(14)21(27)15(2)22(3,4)29-25)19-7-8-20(28-6)17(13-26)16(19)9-11-23(18,24)5/h7-9,11,14-15,18,21,26-27H,10,12-13H2,1-6H3/t14-,15-,18+,21+,23+,24-,25-/m0/s1

InChI Key

ZZLUANSADFHKRE-OFDNLDAYSA-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
Agaricus blazei	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Anisole
Alkyl aryl ether
Ketal
Oxepane
Benzenoid
Pyran
Oxane
Oxolane
Secondary alcohol
Acetal
Ether
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Primary 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	3.89	ALOGPS
logP	3.73	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.95	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	116 m³·mol⁻¹	ChemAxon
Polarizability	46.49 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

C00036811

Chemspider ID

78437698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12069786

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hirotani M, Sai K, Hirotani S, Yoshikawa T: Blazeispirols B, C, E and F, des-A-ergostane-type compounds, from the cultured mycelia of the fungus Agaricus blazei. Phytochemistry. 2002 Mar;59(5):571-7. doi: 10.1016/s0031-9422(01)00445-9. [PubMed:11853754 ]
Xiang R, Li M, Gu Z, Liu H, Zeng H, Peng J: Chronic endometritis positively correlates with the aggravation of intrauterine adhesions but has limited effects on reproductive prognosis with antibiotic application. Int J Gynaecol Obstet. 2022 Sep 1. doi: 10.1002/ijgo.14434. [PubMed:36049892 ]
Li M, Yue C: Abnormal uterine artery Doppler ultrasound during gestational 21-23 weeks associated with preeclampsia. Int J Gynaecol Obstet. 2022 Sep 1. doi: 10.1002/ijgo.14435. [PubMed:36049891 ]
Meyer R, Weisz B, Eilenberg R, Tsadok MA, Uziel M, Sivan E, Mazaki-Tovi S, Tsur A: Utilizing Machine Learning to Predict Unplanned Cesarean Delivery. Int J Gynaecol Obstet. 2022 Sep 1. doi: 10.1002/ijgo.14433. [PubMed:36049888 ]
Crockett C, Lorimer C: OncoFlash - Research Updates in a Flash! (September Edition). Clin Oncol (R Coll Radiol). 2022 Sep;34(9):551-553. doi: 10.1016/j.clon.2022.07.009. [PubMed:36049887 ]
Authors unspecified: Corrigendum. Low Urin Tract Symptoms. 2022 Sep;14(5):405. doi: 10.1111/luts.12458. [PubMed:36049886 ]
Beermann M, Jonsdottir G, Cronisoe A, Hasselrot K, Kopp Kallner H: Long term follow-up of uterine fibroids treated with microwave ablation: an up to 3-year observational study of volume, regrowth, and symptoms. Int J Hyperthermia. 2022;39(1):1158-1163. doi: 10.1080/02656736.2022.2109764. [PubMed:36049885 ]
Al-Dadah O, Hing C: Patellofemoral instability. Knee. 2022 Aug;37:A1-A2. doi: 10.1016/j.knee.2022.07.015. [PubMed:36049884 ]
Lirk P, Vlassakov K: Orthopedic Anesthesiology 2022. Anesthesiol Clin. 2022 Sep;40(3):xv-xvi. doi: 10.1016/j.anclin.2022.08.002. [PubMed:36049883 ]
Fleisher LA: Orthopedic Anesthesiology: A Constantly Evolving Area of Perioperative Care. Anesthesiol Clin. 2022 Sep;40(3):xiii-xiv. doi: 10.1016/j.anclin.2022.08.001. [PubMed:36049882 ]
LOTUS database [Link]

Showing NP-Card for (1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol (NP0148325)

MOL for NP0148325 ((1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol)

3D MOL for NP0148325 ((1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol)

3D SDF for NP0148325 ((1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol)

3D-SDF for NP0148325 ((1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol)

PDB for NP0148325 ((1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol)

3D PDB for NP0148325 ((1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol)

SMILES for NP0148325 ((1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol)

INCHI for NP0148325 ((1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol)

Structure for NP0148325 ((1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol)

3D Structure for NP0148325 ((1'r,2s,3r,4s,10'r,11'r,12's)-6'-(hydroxymethyl)-5'-methoxy-4,5,5,10',12'-pentamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6',8'-tetraen-3-ol)