NP-MRD: Showing NP-Card for 24-hydroxyverruculogen (NP0012461)

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Record Information

Version

2.0

Created at

2021-01-05 21:49:59 UTC

Updated at

2021-07-15 17:11:49 UTC

NP-MRD ID

NP0012461

Secondary Accession Numbers

None

Natural Product Identification

Common Name

24-hydroxyverruculogen

Provided By

NPAtlas

Description

24-hydroxyverruculogen is found in Penicillium and Penicillium brefeldianum. 24-hydroxyverruculogen was first documented in 2014 (PMID: 24473173). Based on a literature review very few articles have been published on 24-hydroxyverruculogen.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117083D          

 71 76  0  0  0  0            999 V2000
   -4.6821    5.5933    0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5732    4.1984    0.4781 O   0  0  0  0  0  0  0  0  0  0  0  0
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 38 71  1  0  0  0  0
M  END

     RDKit          3D

 71 76  0  0  0  0  0  0  0  0999 V2000
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 31 67  1  0
 31 68  1  0
 36 69  1  0
 37 70  1  1
 38 71  1  0
M  END


  Mrv1652306242117083D          

 71 76  0  0  0  0            999 V2000
   -4.6821    5.5933    0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5732    4.1984    0.4781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3078    3.5905    0.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900    4.3779    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    3.7407    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8616    2.3807    0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2240    1.5116    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2151    0.2165    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647    0.2794    0.1782 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692    1.5537    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997    2.2078    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6605   -0.6770    0.1011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6586   -1.3961   -1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5875   -2.3174   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6406   -2.6684   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6353   -3.0877   -2.6919 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6254   -2.6970   -3.5489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613   -1.6371    1.1093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4639   -2.2914    0.9201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5760   -1.9827    1.9300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9711   -0.8893    2.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4576   -3.2571    2.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7752   -1.8069    1.2710 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7619   -0.9183    0.0867 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0706   -0.4461   -0.2381 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762   -1.3276   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2365   -2.3617    0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4097   -1.0645   -1.0102 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6193   -1.6296   -0.3007 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7443   -0.8721   -0.9997 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0836    0.4128   -1.5235 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7280    0.3321   -1.0262 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739    1.2722   -0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708    2.4199   -0.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498    0.9264   -0.6418 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8793    1.1816   -1.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6593    1.8323    0.3509 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9074    3.1589    0.0151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0171    6.1198   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7011    5.9574    0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3343    5.9458    1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0566    4.3235    0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    1.6646    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6569   -0.2277    0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9347   -1.1952   -1.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7833   -1.9215    0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6201   -2.7415   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4772   -3.6980    0.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759   -4.1840   -2.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6450   -2.9452   -3.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0044   -1.9694   -4.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8142   -1.1613    3.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0616   -0.6868    2.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284    0.0634    2.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396   -3.1605    3.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4491   -3.4420    3.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2576   -4.1057    2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0342   -2.8644    0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5213   -1.4758    2.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4470   -1.5612   -0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3564   -1.5379   -1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7179   -2.7149   -0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6130   -1.2707    0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5254   -0.5518   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1508   -1.4083   -1.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6079    1.3128   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1295    0.4461   -2.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5544    0.8723   -2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0553    1.5792    1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304    3.2118   -0.9871 H   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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 11  3  1  0  0  0  0
 35 25  1  0  0  0  0
 10  6  1  0  0  0  0
 32 28  1  0  0  0  0
 37  7  1  0  0  0  0
 24  8  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  4 42  1  0  0  0  0
  5 43  1  0  0  0  0
 11 44  1  0  0  0  0
 12 45  1  1  0  0  0
 13 46  1  0  0  0  0
 15 47  1  0  0  0  0
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 16 51  1  0  0  0  0
 17 52  1  0  0  0  0
 21 53  1  0  0  0  0
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 22 58  1  0  0  0  0
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 23 60  1  0  0  0  0
 24 61  1  6  0  0  0
 28 62  1  6  0  0  0
 29 63  1  0  0  0  0
 29 64  1  0  0  0  0
 30 65  1  0  0  0  0
 30 66  1  0  0  0  0
 31 67  1  0  0  0  0
 31 68  1  0  0  0  0
 36 69  1  0  0  0  0
 37 70  1  1  0  0  0
 38 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0012461

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(=C(/[H])[C@@]1([H])OOC(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[C@]2([H])N3C(=O)[C@@]4([H])N(C(=O)[C@]3(O[H])[C@@]([H])(O[H])C3=C2N1C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C31)C([H])([H])C([H])([H])C4([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O8/c1-14(13-31)10-20-29-18-11-15(36-4)7-8-16(18)21-22(29)19(12-26(2,3)38-37-20)30-24(33)17-6-5-9-28(17)25(34)27(30,35)23(21)32/h7-8,10-11,17,19-20,23,31-32,35H,5-6,9,12-13H2,1-4H3/b14-10+/t17-,19-,20+,23-,27+/m0/s1

> <INCHI_KEY>
OPUYAZPZORIADD-JKPGSCGLSA-N

> <FORMULA>
C27H33N3O8

> <MOLECULAR_WEIGHT>
527.574

> <EXACT_MASS>
527.226765035

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.870578744246615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,14S,17S,23R,24S)-23,24-dihydroxy-9-[(1E)-3-hydroxy-2-methylprop-1-en-1-yl]-5-methoxy-12,12-dimethyl-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0^{2,7}.0^{8,25}.0^{15,23}.0^{17,21}]pentacosa-1(25),2,4,6-tetraene-16,22-dione

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
1.1480349133333339

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.51682522134358

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.134762878930626

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7354658674971306

> <JCHEM_POLAR_SURFACE_AREA>
133.93

> <JCHEM_REFRACTIVITY>
134.80689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,14S,17S,23R,24S)-23,24-dihydroxy-9-[(1E)-3-hydroxy-2-methylprop-1-en-1-yl]-5-methoxy-12,12-dimethyl-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0^{2,7}.0^{8,25}.0^{15,23}.0^{17,21}]pentacosa-1(25),2,4,6-tetraene-16,22-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 76  0  0  0  0  0  0  0  0999 V2000
   -4.6821    5.5933    0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5732    4.1984    0.4781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3078    3.5905    0.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900    4.3779    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    3.7407    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8616    2.3807    0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2240    1.5116    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2151    0.2165    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647    0.2794    0.1782 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692    1.5537    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997    2.2078    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6605   -0.6770    0.1011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6586   -1.3961   -1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5875   -2.3174   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6406   -2.6684   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7752   -1.8069    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7619   -0.9183    0.0867 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0706   -0.4461   -0.2381 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7443   -0.8721   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0836    0.4128   -1.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7280    0.3321   -1.0262 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739    1.2722   -0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708    2.4199   -0.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498    0.9264   -0.6418 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8793    1.1816   -1.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6593    1.8323    0.3509 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9074    3.1589    0.0151 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8142   -1.1613    3.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3396   -3.1605    3.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4491   -3.4420    3.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2576   -4.1057    2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0342   -2.8644    0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5213   -1.4758    2.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4470   -1.5612   -0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3564   -1.5379   -1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7179   -2.7149   -0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6130   -1.2707    0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5254   -0.5518   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1508   -1.4083   -1.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6079    1.3128   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1295    0.4461   -2.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5544    0.8723   -2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0553    1.5792    1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304    3.2118   -0.9871 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
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  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
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 29 30  1  0
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 31 32  1  0
 32 33  1  0
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 33 35  1  0
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 37 38  1  0
 11  3  1  0
 35 25  1  0
 10  6  1  0
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 37  7  1  0
 24  8  1  0
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 31 67  1  0
 31 68  1  0
 36 69  1  0
 37 70  1  1
 38 71  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.682   5.593   0.592  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.573   4.198   0.478  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.308   3.591   0.439  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.190   4.378   0.514  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.965   3.741   0.471  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.862   2.381   0.359  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.224   1.512   0.296  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.215   0.217   0.183  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.565   0.279   0.178  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.969   1.554   0.281  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.200   2.208   0.325  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.660  -0.677   0.101  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.659  -1.396  -1.182  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.587  -2.317  -1.394  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.641  -2.668  -0.400  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.635  -3.088  -2.692  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.625  -2.697  -3.549  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.561  -1.637   1.109  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.464  -2.291   0.920  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.576  -1.983   1.930  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.971  -0.889   2.842  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.458  -3.257   2.785  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.775  -1.807   1.271  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.762  -0.918   0.087  0.00  0.00           C+0
HETATM   25  N   UNK     0       2.071  -0.446  -0.238  0.00  0.00           N+0
HETATM   26  C   UNK     0       3.176  -1.328  -0.188  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.236  -2.362   0.508  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.410  -1.065  -1.010  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.619  -1.630  -0.301  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.744  -0.872  -1.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.084   0.413  -1.524  0.00  0.00           C+0
HETATM   32  N   UNK     0       4.728   0.332  -1.026  0.00  0.00           N+0
HETATM   33  C   UNK     0       3.774   1.272  -0.594  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.171   2.420  -0.163  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.350   0.926  -0.642  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.879   1.182  -1.928  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.659   1.832   0.351  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.907   3.159   0.015  0.00  0.00           O+0
HETATM   39  H   UNK     0      -4.017   6.120  -0.155  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.701   5.957   0.349  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.334   5.946   1.587  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.244   5.468   0.604  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.057   4.324   0.528  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.125   1.665   0.271  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.657  -0.228   0.224  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.935  -1.195  -1.937  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.783  -1.922   0.377  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.620  -2.741  -0.957  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.477  -3.698   0.006  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.576  -4.184  -2.450  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.645  -2.945  -3.144  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.004  -1.969  -4.128  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.814  -1.161   3.928  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.062  -0.687   2.752  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.428   0.063   2.720  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.340  -3.160   3.531  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.449  -3.442   3.210  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.258  -4.106   2.073  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.034  -2.864   0.948  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.521  -1.476   2.007  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.447  -1.561  -0.793  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.356  -1.538  -1.995  0.00  0.00           H+0
HETATM   63  H   UNK     0       5.718  -2.715  -0.397  0.00  0.00           H+0
HETATM   64  H   UNK     0       5.613  -1.271   0.754  0.00  0.00           H+0
HETATM   65  H   UNK     0       7.525  -0.552  -0.286  0.00  0.00           H+0
HETATM   66  H   UNK     0       7.151  -1.408  -1.857  0.00  0.00           H+0
HETATM   67  H   UNK     0       6.608   1.313  -1.161  0.00  0.00           H+0
HETATM   68  H   UNK     0       6.130   0.446  -2.634  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.554   0.872  -2.569  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.055   1.579   1.373  0.00  0.00           H+0
HETATM   71  H   UNK     0       1.930   3.212  -0.987  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   42                                                  
CONECT    5    4    6   43                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8   37                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11    6                                                  
CONECT   11   10    3   44                                                  
CONECT   12    9   13   18   45                                             
CONECT   13   12   14   46                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   47   48   49                                             
CONECT   16   14   17   50   51                                             
CONECT   17   16   52                                                       
CONECT   18   12   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20   53   54   55                                             
CONECT   22   20   56   57   58                                             
CONECT   23   20   24   59   60                                             
CONECT   24   23   25    8   61                                             
CONECT   25   24   26   35                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   32   62                                             
CONECT   29   28   30   63   64                                             
CONECT   30   29   31   65   66                                             
CONECT   31   30   32   67   68                                             
CONECT   32   31   33   28                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37   25                                             
CONECT   36   35   69                                                       
CONECT   37   35   38    7   70                                             
CONECT   38   37   71                                                       
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    4                                                            
CONECT   43    5                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   15                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   17                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   21                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   23                                                            
CONECT   61   24                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   29                                                            
CONECT   65   30                                                            
CONECT   66   30                                                            
CONECT   67   31                                                            
CONECT   68   31                                                            
CONECT   69   36                                                            
CONECT   70   37                                                            
CONECT   71   38                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  152    0
END

RDKit          3D

71 76  0  0  0  0  0  0  0  0999 V2000
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    0.2240    1.5116    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2151    0.2165    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647    0.2794    0.1782 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1997    2.2078    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6605   -0.6770    0.1011 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.5875   -2.3174   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6406   -2.6684   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1708    2.4199   -0.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9074    3.1589    0.0151 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1508   -1.4083   -1.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6079    1.3128   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5544    0.8723   -2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0553    1.5792    1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304    3.2118   -0.9871 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  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  6
 35 37  1  0
 37 38  1  0
 11  3  1  0
 35 25  1  0
 10  6  1  0
 32 28  1  0
 37  7  1  0
 24  8  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  4 42  1  0
  5 43  1  0
 11 44  1  0
 12 45  1  1
 13 46  1  0
 15 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 21 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  6
 28 62  1  6
 29 63  1  0
 29 64  1  0
 30 65  1  0
 30 66  1  0
 31 67  1  0
 31 68  1  0
 36 69  1  0
 37 70  1  1
 38 71  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃N₃O₈

Average Mass

527.5740 Da

Monoisotopic Mass

527.22677 Da

IUPAC Name

(9R,14S,17S,23R,24S)-23,24-dihydroxy-9-[(1E)-3-hydroxy-2-methylprop-1-en-1-yl]-5-methoxy-12,12-dimethyl-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0^{2,7}.0^{8,25}.0^{15,23}.0^{17,21}]pentacosa-1(25),2,4,6-tetraene-16,22-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C1=C3[C@H](CC(C)(C)OO[C@H](\C=C(/C)CO)N23)N2C(=O)[C@@H]3CCCN3C(=O)[C@]2(O)[C@H]1O

InChI Identifier

InChI=1S/C27H33N3O8/c1-14(13-31)10-20-29-18-11-15(36-4)7-8-16(18)21-22(29)19(12-26(2,3)38-37-20)30-24(33)17-6-5-9-28(17)25(34)27(30,35)23(21)32/h7-8,10-11,17,19-20,23,31-32,35H,5-6,9,12-13H2,1-4H3/b14-10+/t17-,19-,20+,23-,27+/m0/s1

InChI Key

OPUYAZPZORIADD-JKPGSCGLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium	NPAtlas	24473173
Penicillium brefeldianum	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	1.05	ALOGPS
logP	1.15	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.13	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	133.93 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	134.81 m³·mol⁻¹	ChemAxon
Polarizability	55.87 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002241

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

32674758

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583723

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

An CY, Li XM, Li CS, Xu GM, Wang BG: Prenylated indolediketopiperazine peroxides and related homologues from the marine sediment-derived fungus Penicillium brefeldianum SD-273. Mar Drugs. 2014 Jan 27;12(2):746-56. doi: 10.3390/md12020746. [PubMed:24473173 ]

Showing NP-Card for 24-hydroxyverruculogen (NP0012461)

MOL for NP0012461 (24-hydroxyverruculogen)

3D MOL for NP0012461 (24-hydroxyverruculogen)

3D SDF for NP0012461 (24-hydroxyverruculogen)

3D-SDF for NP0012461 (24-hydroxyverruculogen)

PDB for NP0012461 (24-hydroxyverruculogen)

3D PDB for NP0012461 (24-hydroxyverruculogen)

SMILES for NP0012461 (24-hydroxyverruculogen)

INCHI for NP0012461 (24-hydroxyverruculogen)

Structure for NP0012461 (24-hydroxyverruculogen)

3D Structure for NP0012461 (24-hydroxyverruculogen)