NP-MRD: Showing NP-Card for acremine H (NP0037962)

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Record Information

Version

2.0

Created at

2021-06-20 20:46:10 UTC

Updated at

2021-06-30 00:10:28 UTC

NP-MRD ID

NP0037962

Secondary Accession Numbers

None

Natural Product Identification

Common Name

acremine H

Provided By

JEOL Database JEOL Logo

Description

(4S,6R)-4,6-dihydroxy-3-[(2R,3S)-3-(2-hydroxypropan-2-yl)oxiran-2-yl]-6-methylcyclohex-2-en-1-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. acremine H is found in Acremonium byssoides. acremine H was first documented in 2009 (Arnone, A., et al.). Based on a literature review very few articles have been published on (4S,6R)-4,6-dihydroxy-3-[(2R,3S)-3-(2-hydroxypropan-2-yl)oxiran-2-yl]-6-methylcyclohex-2-en-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122463D          

 35 36  0  0  0  0            999 V2000
   -2.3532   -2.3024   -1.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -1.4060   -0.3050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3294   -1.3795   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -1.9832    0.9084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2637   -0.0087   -0.4754 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0007    0.6895    0.7492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8545    0.3612   -0.0652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1274    1.3855   -0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1201    2.6855   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736    3.6910   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5699    4.8854   -0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    3.1960   -2.3108 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0014    2.8875   -1.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8654    4.2213   -3.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    1.9964   -3.0253 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6357    0.8815   -2.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1848   -0.0413   -2.7731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2604   -2.3819   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6911   -1.9172   -2.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7350   -3.3221   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7303   -2.3847   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6579   -0.7622    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -0.9733   -1.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345   -1.3044    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7258    0.5351   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158   -0.4366    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6765    3.0560    0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4368    3.7950   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9267    2.1428   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    2.5268   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8338    5.0704   -2.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    2.3193   -3.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7300    1.6037   -3.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.3346   -1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3269   -0.3622   -3.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
 16  8  1  0  0  0  0
 12 14  1  6  0  0  0
 15 12  1  0  0  0  0
 16 17  1  0  0  0  0
 12 10  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
  5  2  1  0  0  0  0
  2  4  1  1  0  0  0
 10 11  2  0  0  0  0
  2  1  1  0  0  0  0
 16 15  1  0  0  0  0
  2  3  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  1  0  0  0  0
 16 34  1  1  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
  9 27  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 17 35  1  0  0  0  0
  7 26  1  1  0  0  0
  5 25  1  6  0  0  0
  4 24  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
M  END

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.3532   -2.3024   -1.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -1.4060   -0.3050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3294   -1.3795   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -1.9832    0.9084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2637   -0.0087   -0.4754 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0007    0.6895    0.7492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8545    0.3612   -0.0652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1274    1.3855   -0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1201    2.6855   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736    3.6910   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5699    4.8854   -0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    3.1960   -2.3108 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0014    2.8875   -1.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8654    4.2213   -3.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    1.9964   -3.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6357    0.8815   -2.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1848   -0.0413   -2.7731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2604   -2.3819   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6911   -1.9172   -2.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7350   -3.3221   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7303   -2.3847   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6579   -0.7622    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -0.9733   -1.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345   -1.3044    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7258    0.5351   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158   -0.4366    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6765    3.0560    0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4368    3.7950   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9267    2.1428   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    2.5268   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8338    5.0704   -2.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    2.3193   -3.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7300    1.6037   -3.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.3346   -1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3269   -0.3622   -3.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 16  8  1  0
 12 14  1  6
 15 12  1  0
 16 17  1  0
 12 10  1  0
  8  7  1  0
 10  9  1  0
  7  5  1  0
  9  8  2  0
  5  2  1  0
  2  4  1  1
 10 11  2  0
  2  1  1  0
 16 15  1  0
  2  3  1  0
  7  6  1  0
  5  6  1  0
 16 34  1  1
 15 32  1  0
 15 33  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 17 35  1  0
  7 26  1  1
  5 25  1  6
  4 24  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
M  END


  Mrv1652306202122463D          

 35 36  0  0  0  0            999 V2000
   -2.3532   -2.3024   -1.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -1.4060   -0.3050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3294   -1.3795   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -1.9832    0.9084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2637   -0.0087   -0.4754 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0007    0.6895    0.7492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8545    0.3612   -0.0652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1274    1.3855   -0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1201    2.6855   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736    3.6910   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5699    4.8854   -0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    3.1960   -2.3108 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0014    2.8875   -1.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8654    4.2213   -3.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    1.9964   -3.0253 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6357    0.8815   -2.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1848   -0.0413   -2.7731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2604   -2.3819   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6911   -1.9172   -2.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7350   -3.3221   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7303   -2.3847   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6579   -0.7622    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -0.9733   -1.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345   -1.3044    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7258    0.5351   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158   -0.4366    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6765    3.0560    0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4368    3.7950   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9267    2.1428   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    2.5268   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8338    5.0704   -2.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    2.3193   -3.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7300    1.6037   -3.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.3346   -1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3269   -0.3622   -3.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
 16  8  1  0  0  0  0
 12 14  1  6  0  0  0
 15 12  1  0  0  0  0
 16 17  1  0  0  0  0
 12 10  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
  5  2  1  0  0  0  0
  2  4  1  1  0  0  0
 10 11  2  0  0  0  0
  2  1  1  0  0  0  0
 16 15  1  0  0  0  0
  2  3  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  1  0  0  0  0
 16 34  1  1  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
  9 27  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 17 35  1  0  0  0  0
  7 26  1  1  0  0  0
  5 25  1  6  0  0  0
  4 24  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037962

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=C([H])C(=O)[C@@](O[H])(C([H])([H])[H])C1([H])[H])[C@@]1([H])O[C@]1([H])C(O[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O5/c1-11(2,15)10-9(17-10)6-4-8(14)12(3,16)5-7(6)13/h4,7,9-10,13,15-16H,5H2,1-3H3/t7-,9+,10-,12+/m0/s1

> <INCHI_KEY>
RTZBRQKHLKNJNE-NCIFOGHDSA-N

> <FORMULA>
C12H18O5

> <MOLECULAR_WEIGHT>
242.271

> <EXACT_MASS>
242.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.53163825436932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,6R)-4,6-dihydroxy-3-[(2R,3S)-3-(2-hydroxypropan-2-yl)oxiran-2-yl]-6-methylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
-0.30

> <JCHEM_LOGP>
-0.6951118569999996

> <ALOGPS_LOGS>
-1.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.039654217953046

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.098775014712519

> <JCHEM_PKA_STRONGEST_BASIC>
-3.06938184193874

> <JCHEM_POLAR_SURFACE_AREA>
90.29

> <JCHEM_REFRACTIVITY>
60.5467

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,6R)-4,6-dihydroxy-3-[(2R,3S)-3-(2-hydroxypropan-2-yl)oxiran-2-yl]-6-methylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.3532   -2.3024   -1.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -1.4060   -0.3050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3294   -1.3795   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -1.9832    0.9084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2637   -0.0087   -0.4754 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0007    0.6895    0.7492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8545    0.3612   -0.0652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1274    1.3855   -0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1201    2.6855   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736    3.6910   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5699    4.8854   -0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    3.1960   -2.3108 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0014    2.8875   -1.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8654    4.2213   -3.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    1.9964   -3.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6357    0.8815   -2.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1848   -0.0413   -2.7731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2604   -2.3819   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6911   -1.9172   -2.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7350   -3.3221   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7303   -2.3847   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6579   -0.7622    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -0.9733   -1.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345   -1.3044    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7258    0.5351   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158   -0.4366    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6765    3.0560    0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4368    3.7950   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9267    2.1428   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    2.5268   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8338    5.0704   -2.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    2.3193   -3.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7300    1.6037   -3.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.3346   -1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3269   -0.3622   -3.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 16  8  1  0
 12 14  1  6
 15 12  1  0
 16 17  1  0
 12 10  1  0
  8  7  1  0
 10  9  1  0
  7  5  1  0
  9  8  2  0
  5  2  1  0
  2  4  1  1
 10 11  2  0
  2  1  1  0
 16 15  1  0
  2  3  1  0
  7  6  1  0
  5  6  1  0
 16 34  1  1
 15 32  1  0
 15 33  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 17 35  1  0
  7 26  1  1
  5 25  1  6
  4 24  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.353  -2.302  -1.456  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.803  -1.406  -0.305  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.329  -1.379  -0.214  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.307  -1.983   0.908  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.264  -0.009  -0.475  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.001   0.690   0.749  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.855   0.361  -0.065  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.127   1.385  -0.849  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.120   2.686  -0.496  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.674   3.691  -1.239  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.570   4.885  -0.962  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.651   3.196  -2.311  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.001   2.888  -1.667  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.865   4.221  -3.284  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.040   1.996  -3.025  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.636   0.882  -2.061  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.185  -0.041  -2.773  0.00  0.00           O+0
HETATM   18  H   UNK     0      -1.260  -2.382  -1.484  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.691  -1.917  -2.424  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.735  -3.322  -1.333  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.730  -2.385  -0.042  0.00  0.00           H+0
HETATM   22  H   UNK     0      -4.658  -0.762   0.631  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.782  -0.973  -1.125  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.434  -1.304   1.597  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.726   0.535  -1.290  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.216  -0.437   0.304  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.677   3.056   0.359  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.437   3.795  -1.232  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.927   2.143  -0.868  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.716   2.527  -2.415  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.834   5.070  -2.796  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.162   2.319  -3.604  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.730   1.604  -3.784  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.521   0.335  -1.715  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.327  -0.362  -3.536  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2    5    4    1    3                                             
CONECT    3    2   21   22   23                                             
CONECT    4    2   24                                                       
CONECT    5    7    2    6   25                                             
CONECT    6    7    5                                                       
CONECT    7    8    5    6   26                                             
CONECT    8   16    7    9                                                  
CONECT    9   10    8   27                                                  
CONECT   10   12    9   11                                                  
CONECT   11   10                                                            
CONECT   12   13   14   15   10                                             
CONECT   13   12   28   29   30                                             
CONECT   14   12   31                                                       
CONECT   15   12   16   32   33                                             
CONECT   16    8   17   15   34                                             
CONECT   17   16   35                                                       
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    3                                                            
CONECT   22    3                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    9                                                            
CONECT   28   13                                                            
CONECT   29   13                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   17                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

RDKit          3D

35 36  0  0  0  0  0  0  0  0999 V2000
   -2.3532   -2.3024   -1.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -1.4060   -0.3050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3294   -1.3795   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -1.9832    0.9084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2637   -0.0087   -0.4754 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0007    0.6895    0.7492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8545    0.3612   -0.0652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1274    1.3855   -0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1201    2.6855   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736    3.6910   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5699    4.8854   -0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    3.1960   -2.3108 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0014    2.8875   -1.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8654    4.2213   -3.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    1.9964   -3.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6357    0.8815   -2.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1848   -0.0413   -2.7731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2604   -2.3819   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6911   -1.9172   -2.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7350   -3.3221   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7303   -2.3847   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6579   -0.7622    0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -0.9733   -1.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345   -1.3044    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7258    0.5351   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158   -0.4366    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6765    3.0560    0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4368    3.7950   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9267    2.1428   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    2.5268   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8338    5.0704   -2.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    2.3193   -3.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7300    1.6037   -3.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.3346   -1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3269   -0.3622   -3.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 16  8  1  0
 12 14  1  6
 15 12  1  0
 16 17  1  0
 12 10  1  0
  8  7  1  0
 10  9  1  0
  7  5  1  0
  9  8  2  0
  5  2  1  0
  2  4  1  1
 10 11  2  0
  2  1  1  0
 16 15  1  0
  2  3  1  0
  7  6  1  0
  5  6  1  0
 16 34  1  1
 15 32  1  0
 15 33  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 17 35  1  0
  7 26  1  1
  5 25  1  6
  4 24  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₈O₅

Average Mass

242.2710 Da

Monoisotopic Mass

242.11542 Da

IUPAC Name

(4S,6R)-4,6-dihydroxy-3-[(2R,3S)-3-(2-hydroxypropan-2-yl)oxiran-2-yl]-6-methylcyclohex-2-en-1-one

Traditional Name

(4S,6R)-4,6-dihydroxy-3-[(2R,3S)-3-(2-hydroxypropan-2-yl)oxiran-2-yl]-6-methylcyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C(=C([H])C(=O)[C@@](O[H])(C([H])([H])[H])C1([H])[H])[C@@]1([H])O[C@]1([H])C(O[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C12H18O5/c1-11(2,15)10-9(17-10)6-4-8(14)12(3,16)5-7(6)13/h4,7,9-10,13,15-16H,5H2,1-3H3/t7-,9+,10-,12+/m0/s1

InChI Key

RTZBRQKHLKNJNE-NCIFOGHDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Simplicillium lanosoniveum	JEOL database	Arnone, A., et al, Tetrahedron 65, 786 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Acyloin
Tertiary alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-0.3	ALOGPS
logP	-0.7	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	13.1	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.55 m³·mol⁻¹	ChemAxon
Polarizability	24.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

27445047

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25214160

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Arnone, A., et al. (2009). Arnone, A., et al, Tetrahedron 65, 786 (2009). Tetrahedron.

Showing NP-Card for acremine H (NP0037962)

MOL for NP0037962 (acremine H)

3D MOL for NP0037962 (acremine H)

3D SDF for NP0037962 (acremine H)

3D-SDF for NP0037962 (acremine H)

PDB for NP0037962 (acremine H)

3D PDB for NP0037962 (acremine H)

SMILES for NP0037962 (acremine H)

INCHI for NP0037962 (acremine H)

Structure for NP0037962 (acremine H)

3D Structure for NP0037962 (acremine H)