NP-MRD: Showing NP-Card for 5-demethylovalicin (NP0003950)

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Record Information

Version

1.0

Created at

2020-12-09 01:29:10 UTC

Updated at

2021-07-15 16:47:49 UTC

NP-MRD ID

NP0003950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-demethylovalicin

Provided By

NPAtlas

Description

(3S,4R,5S)-4,5-dihydroxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]Octan-6-one belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). 5-demethylovalicin is found in Chrysosporium lucknowense. It was first documented in 2002 (PMID: 11738620). Based on a literature review very few articles have been published on (3S,4R,5S)-4,5-dihydroxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]Octan-6-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117513D          

 42 44  0  0  0  0            999 V2000
    4.6688    1.1558    0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951    0.1422   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -0.2310   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.4199    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -1.4204    0.1488 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5106   -1.1776    0.1644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1822   -1.0427    1.3634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.0862    0.4370 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5898    1.2227    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995    0.4078   -0.3072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1087    1.5469   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7939   -0.6425   -1.3095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5749    0.0074   -2.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6956   -1.6540   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691   -2.8188   -1.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7802   -1.2786    0.2057 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1343   -0.4603    1.2974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4476    0.7225    0.6784 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4035    1.8697    0.3471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3978    1.8795    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6965    0.9704    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    2.1837    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857    1.0083    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7027    0.4681   -1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229   -0.0755   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512   -1.2787   -1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -0.1697    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3337   -1.6653   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309   -2.3985    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -1.9650   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7665    1.0860    2.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354    2.1034    1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860    1.6126    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    1.2565   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9891   -1.1000   -1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5860   -0.5352   -3.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3199   -2.1428    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498   -0.5767   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9236   -0.0291    1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235   -1.0352    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1729    2.5216   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039    1.8663    0.7960 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
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8  6  1  0  0  0  0
 18 10  1  0  0  0  0
 18 20  1  1  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  6  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
 11 34  1  0  0  0  0
 12 35  1  6  0  0  0
 13 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6688    1.1558    0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951    0.1422   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -0.2310   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.4199    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -1.4204    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5106   -1.1776    0.1644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1822   -1.0427    1.3634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.0862    0.4370 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5898    1.2227    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995    0.4078   -0.3072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1087    1.5469   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7939   -0.6425   -1.3095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5749    0.0074   -2.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6956   -1.6540   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691   -2.8188   -1.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7802   -1.2786    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343   -0.4603    1.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4476    0.7225    0.6784 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4035    1.8697    0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3978    1.8795    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6965    0.9704    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    2.1837    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857    1.0083    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7027    0.4681   -1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229   -0.0755   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512   -1.2787   -1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -0.1697    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3337   -1.6653   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309   -2.3985    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -1.9650   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7665    1.0860    2.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354    2.1034    1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860    1.6126    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    1.2565   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9891   -1.1000   -1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5860   -0.5352   -3.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3199   -2.1428    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498   -0.5767   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9236   -0.0291    1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235   -1.0352    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1729    2.5216   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039    1.8663    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8  6  1  0
 18 10  1  0
 18 20  1  1
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  6
  9 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 12 35  1  6
 13 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
M  END


  Mrv1652306242117513D          

 42 44  0  0  0  0            999 V2000
    4.6688    1.1558    0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951    0.1422   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -0.2310   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.4199    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -1.4204    0.1488 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5106   -1.1776    0.1644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1822   -1.0427    1.3634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.0862    0.4370 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5898    1.2227    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995    0.4078   -0.3072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1087    1.5469   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7939   -0.6425   -1.3095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5749    0.0074   -2.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6956   -1.6540   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691   -2.8188   -1.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7802   -1.2786    0.2057 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1343   -0.4603    1.2974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4476    0.7225    0.6784 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4035    1.8697    0.3471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3978    1.8795    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6965    0.9704    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    2.1837    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857    1.0083    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7027    0.4681   -1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229   -0.0755   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512   -1.2787   -1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -0.1697    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3337   -1.6653   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309   -2.3985    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -1.9650   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7665    1.0860    2.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354    2.1034    1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860    1.6126    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    1.2565   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9891   -1.1000   -1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5860   -0.5352   -3.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3199   -2.1428    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498   -0.5767   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9236   -0.0291    1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235   -1.0352    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1729    2.5216   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039    1.8663    0.7960 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
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8  6  1  0  0  0  0
 18 10  1  0  0  0  0
 18 20  1  1  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  6  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
 11 34  1  0  0  0  0
 12 35  1  6  0  0  0
 13 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=O)C([H])([H])C([H])([H])[C@@]2(OC2([H])[H])[C@@]1(O[H])[C@]1(O[C@]1([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-9(2)4-5-11-13(3,20-11)15(18)12(17)10(16)6-7-14(15)8-19-14/h4,11-12,17-18H,5-8H2,1-3H3/t11-,12-,13+,14+,15+/m1/s1

> <INCHI_KEY>
PCNIYGYCVFRRRE-MRLBHPIUSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.069040760363524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R,5S)-4,5-dihydroxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one

> <ALOGPS_LOGP>
0.28

> <JCHEM_LOGP>
0.6179777689999999

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.891583053950718

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.113889080331353

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9361912744681598

> <JCHEM_POLAR_SURFACE_AREA>
82.59

> <JCHEM_REFRACTIVITY>
71.9503

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R,5S)-4,5-dihydroxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6688    1.1558    0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951    0.1422   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -0.2310   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.4199    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -1.4204    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5106   -1.1776    0.1644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1822   -1.0427    1.3634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.0862    0.4370 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5898    1.2227    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995    0.4078   -0.3072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1087    1.5469   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7939   -0.6425   -1.3095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5749    0.0074   -2.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6956   -1.6540   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691   -2.8188   -1.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7802   -1.2786    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343   -0.4603    1.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4476    0.7225    0.6784 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4035    1.8697    0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3978    1.8795    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6965    0.9704    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    2.1837    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857    1.0083    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7027    0.4681   -1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229   -0.0755   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512   -1.2787   -1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -0.1697    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3337   -1.6653   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309   -2.3985    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -1.9650   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7665    1.0860    2.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354    2.1034    1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860    1.6126    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    1.2565   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9891   -1.1000   -1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5860   -0.5352   -3.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3199   -2.1428    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498   -0.5767   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9236   -0.0291    1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235   -1.0352    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1729    2.5216   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039    1.8663    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8  6  1  0
 18 10  1  0
 18 20  1  1
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  6
  9 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 12 35  1  6
 13 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  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       4.669   1.156   0.652  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.795   0.142  -0.012  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.950  -0.231  -1.434  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.846  -0.420   0.767  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.969  -1.420   0.149  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.511  -1.178   0.164  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.182  -1.043   1.363  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.096   0.086   0.437  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.590   1.223   1.124  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.399   0.408  -0.307  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.109   1.547  -1.059  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.794  -0.643  -1.310  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.575   0.007  -2.315  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.696  -1.654  -0.745  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.569  -2.819  -1.047  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.780  -1.279   0.206  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.134  -0.460   1.297  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.448   0.723   0.678  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.404   1.870   0.347  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.398   1.880   1.419  0.00  0.00           O+0
HETATM   21  H   UNK     0       5.697   0.970   0.274  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.316   2.184   0.412  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.686   1.008   1.744  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.703   0.468  -1.874  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.023  -0.076  -2.022  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.251  -1.279  -1.555  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.719  -0.170   1.807  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.334  -1.665  -0.903  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.231  -2.398   0.683  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.029  -1.965  -0.462  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.767   1.086   2.208  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.135   2.103   1.097  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.486   1.613   0.655  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.523   1.256  -1.812  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.989  -1.100  -1.880  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.586  -0.535  -3.136  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.320  -2.143   0.592  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.450  -0.577  -0.368  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.924  -0.029   1.981  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.424  -1.035   1.884  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.173   2.522  -0.500  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.404   1.866   0.796  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   24   25   26                                             
CONECT    4    2    5   27                                                  
CONECT    5    4    6   28   29                                             
CONECT    6    5    7    8   30                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10    6                                             
CONECT    9    8   31   32   33                                             
CONECT   10    8   11   12   18                                             
CONECT   11   10   34                                                       
CONECT   12   10   13   14   35                                             
CONECT   13   12   36                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   37   38                                             
CONECT   17   16   18   39   40                                             
CONECT   18   17   19   10   20                                             
CONECT   19   18   20   41   42                                             
CONECT   20   19   18                                                       
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33    9                                                            
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   17                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

RDKit          3D

42 44  0  0  0  0  0  0  0  0999 V2000
    4.6688    1.1558    0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951    0.1422   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -0.2310   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.4199    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -1.4204    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5106   -1.1776    0.1644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1822   -1.0427    1.3634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.0862    0.4370 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5898    1.2227    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995    0.4078   -0.3072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1087    1.5469   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7939   -0.6425   -1.3095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5749    0.0074   -2.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6956   -1.6540   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691   -2.8188   -1.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7802   -1.2786    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343   -0.4603    1.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4476    0.7225    0.6784 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4035    1.8697    0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3978    1.8795    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6965    0.9704    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    2.1837    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6857    1.0083    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7027    0.4681   -1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229   -0.0755   -2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512   -1.2787   -1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -0.1697    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3337   -1.6653   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309   -2.3985    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -1.9650   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7665    1.0860    2.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354    2.1034    1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860    1.6126    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5233    1.2565   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9891   -1.1000   -1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5860   -0.5352   -3.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3199   -2.1428    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498   -0.5767   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9236   -0.0291    1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235   -1.0352    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1729    2.5216   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039    1.8663    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8  6  1  0
 18 10  1  0
 18 20  1  1
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  6
  9 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 12 35  1  6
 13 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₅

Average Mass

282.3360 Da

Monoisotopic Mass

282.14672 Da

IUPAC Name

(3S,4R,5S)-4,5-dihydroxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one

Traditional Name

(3S,4R,5S)-4,5-dihydroxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@H]1O[C@]1(C)[C@@]1(O)[C@H](O)C(=O)CC[C@]11CO1

InChI Identifier

InChI=1S/C15H22O5/c1-9(2)4-5-11-13(3,20-11)15(18)12(17)10(16)6-7-14(15)8-19-14/h4,11-12,17-18H,5-8H2,1-3H3/t11-,12-,13+,14+,15+/m1/s1

InChI Key

PCNIYGYCVFRRRE-MRLBHPIUSA-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
Chrysosporium lucknowense	NPAtlas	11738620

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
1,2-diol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.28	ALOGPS
logP	0.62	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.11	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.95 m³·mol⁻¹	ChemAxon
Polarizability	29.07 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA005200

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8214975

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10039411

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Son KH, Kwon JY, Jeong HW, Kim HK, Kim CJ, Chang YH, Choi JD, Kwon BM: 5-demethylovalicin, as a methionine aminopeptidase-2 inhibitor produced by Chrysosporium. Bioorg Med Chem. 2002 Jan;10(1):185-8. doi: 10.1016/s0968-0896(01)00268-1. [PubMed:11738620 ]

Showing NP-Card for 5-demethylovalicin (NP0003950)

MOL for NP0003950 (5-demethylovalicin)

3D MOL for NP0003950 (5-demethylovalicin)

3D SDF for NP0003950 (5-demethylovalicin)

3D-SDF for NP0003950 (5-demethylovalicin)

PDB for NP0003950 (5-demethylovalicin)

3D PDB for NP0003950 (5-demethylovalicin)

SMILES for NP0003950 (5-demethylovalicin)

INCHI for NP0003950 (5-demethylovalicin)

Structure for NP0003950 (5-demethylovalicin)

3D Structure for NP0003950 (5-demethylovalicin)