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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:16:53 UTC

Update Date

2021-09-26 23:09:07 UTC

HMDB ID

HMDB0254825

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Modrastane

Description

Modrastane belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton. Based on a literature review very few articles have been published on Modrastane. This compound has been identified in human blood as reported by (PMID: 31557052 ). Modrastane is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Modrastane is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0254825
     RDKit          3D
Modrastane
 51 55  0  0  0  0  0  0  0  0999 V2000
   -2.5811    1.6243    1.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4188    0.3737    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7218   -0.7261    1.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396   -0.5490    1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3265   -0.0240    0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549   -0.2739   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.0627   -2.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3020   -0.3465   -2.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885    0.0940   -1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2474    1.5333   -1.0789 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4160    0.6772   -1.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3205    0.5961   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646    1.0072   -0.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190    0.1447    1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8528    0.0806    2.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5878    0.0416    3.0395 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5590   -0.3153    1.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7127   -0.5539    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -2.0584   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8067    0.7131   -0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587    0.6137   -1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1839    0.5834   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8202   -0.1200    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7150   -1.5007    0.2830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683    1.9081    2.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8007    2.4654    0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4144    1.5002    2.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1129   -0.6840    2.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0141   -1.7381    1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2008   -1.5809    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0068    0.1035    2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311    1.0790    0.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689   -1.3004   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4304    0.9498   -2.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -0.7696   -2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4716   -1.4188   -2.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6424    0.2262   -3.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215    0.8467   -2.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8318    2.0072   -0.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0776    0.4490    1.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390   -1.2299    1.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7574   -2.3566   -0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8010   -2.5921    0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5487   -2.3710   -0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3487    1.7350   -0.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -0.2420   -2.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8201    1.5715   -2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5693    1.5709   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232    0.0122   -1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393    0.0440    1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240   -1.7377   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
  6 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 20  2  1  0
 23  2  1  0
 18  5  1  0
 11  9  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 11 38  1  0
 13 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
M  END


  Mrv1652309112116172D          

 24 28  0  0  0  0            999 V2000
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660    1.8191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810   -1.4796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 18 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  3  0  0  0  0
 15 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254825

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CCC45OC4C(O)=C(CC35C)C#N)C1CCC2O

> <INCHI_IDENTIFIER>
InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3

> <INCHI_KEY>
KVJXBPDAXMEYOA-UHFFFAOYSA-N

> <FORMULA>
C20H27NO3

> <MOLECULAR_WEIGHT>
329.44

> <EXACT_MASS>
329.199093733

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.84736649354376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.300783866666666

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.3777053517066

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.231169871976814

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8838175253814861

> <JCHEM_POLAR_SURFACE_AREA>
76.78

> <JCHEM_REFRACTIVITY>
90.1746

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254825
     RDKit          3D
Modrastane
 51 55  0  0  0  0  0  0  0  0999 V2000
   -2.5811    1.6243    1.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4188    0.3737    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7218   -0.7261    1.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396   -0.5490    1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3265   -0.0240    0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549   -0.2739   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.0627   -2.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3020   -0.3465   -2.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885    0.0940   -1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2474    1.5333   -1.0789 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4160    0.6772   -1.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3205    0.5961   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646    1.0072   -0.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190    0.1447    1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8528    0.0806    2.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5878    0.0416    3.0395 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5590   -0.3153    1.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7127   -0.5539    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -2.0584   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8067    0.7131   -0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587    0.6137   -1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1839    0.5834   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8202   -0.1200    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7150   -1.5007    0.2830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683    1.9081    2.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8007    2.4654    0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4144    1.5002    2.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1129   -0.6840    2.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0141   -1.7381    1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2008   -1.5809    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0068    0.1035    2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311    1.0790    0.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689   -1.3004   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4304    0.9498   -2.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -0.7696   -2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4716   -1.4188   -2.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6424    0.2262   -3.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215    0.8467   -2.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8318    2.0072   -0.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0776    0.4490    1.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390   -1.2299    1.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7574   -2.3566   -0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8010   -2.5921    0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5487   -2.3710   -0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3487    1.7350   -0.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -0.2420   -2.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8201    1.5715   -2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5693    1.5709   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232    0.0122   -1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393    0.0440    1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240   -1.7377   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
  6 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 20  2  1  0
 23  2  1  0
 18  5  1  0
 11  9  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 11 38  1  0
 13 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.882  -1.480   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.803   3.396   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.652  -1.585   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -1.645  -2.762   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    2   11                                                  
CONECT   11   10                                                            
CONECT   12    6   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19   20                                             
CONECT   15   14    5   16   24                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   14                                                       
CONECT   21   18                                                            
CONECT   22   17   23                                                       
CONECT   23   22                                                            
CONECT   24   15                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0254825
HETATM    1  C1  UNL     1      -2.581   1.624   1.671  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.419   0.374   0.839  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.722  -0.726   1.587  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.240  -0.549   1.671  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.327  -0.024   0.371  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.655  -0.274  -0.711  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.140  -0.063  -2.098  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.302  -0.347  -2.286  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.189   0.094  -1.160  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.247   1.533  -1.079  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.416   0.677  -1.261  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.321   0.596  -0.115  1.00  0.00           C  
HETATM   13  O2  UNL     1       5.665   1.007  -0.220  1.00  0.00           O  
HETATM   14  C12 UNL     1       3.919   0.145   1.033  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.853   0.081   2.148  1.00  0.00           C  
HETATM   16  N1  UNL     1       5.588   0.042   3.039  1.00  0.00           N  
HETATM   17  C14 UNL     1       2.559  -0.315   1.290  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.713  -0.554   0.093  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.676  -2.058  -0.159  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.807   0.713  -0.472  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.859   0.614  -1.528  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.184   0.583  -0.804  1.00  0.00           C  
HETATM   23  C20 UNL     1      -3.820  -0.120   0.486  1.00  0.00           C  
HETATM   24  O3  UNL     1      -3.715  -1.501   0.283  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.668   1.908   2.208  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.801   2.465   0.954  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.414   1.500   2.372  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.113  -0.684   2.645  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.014  -1.738   1.224  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.201  -1.581   1.797  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.007   0.103   2.530  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.431   1.079   0.499  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.069  -1.300  -0.605  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.430   0.950  -2.447  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.713  -0.770  -2.767  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.472  -1.419  -2.563  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.642   0.226  -3.199  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.922   0.847  -2.232  1.00  0.00           H  
HETATM   39  H15 UNL     1       5.832   2.007  -0.243  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.078   0.449   1.970  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.639  -1.230   1.949  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.757  -2.357  -0.693  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.801  -2.592   0.807  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.549  -2.371  -0.784  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.349   1.735  -0.409  1.00  0.00           H  
HETATM   46  H22 UNL     1      -2.714  -0.242  -2.198  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.820   1.571  -2.118  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.569   1.571  -0.546  1.00  0.00           H  
HETATM   49  H25 UNL     1      -4.923   0.012  -1.390  1.00  0.00           H  
HETATM   50  H26 UNL     1      -4.539   0.044   1.292  1.00  0.00           H  
HETATM   51  H27 UNL     1      -3.824  -1.738  -0.673  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   20   23
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   18   32
CONECT    6    7   20   33
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT    9   10   11   18
CONECT   10   11
CONECT   11   12   38
CONECT   12   13   14   14
CONECT   13   39
CONECT   14   15   17
CONECT   15   16   16   16
CONECT   17   18   40   41
CONECT   18   19
CONECT   19   42   43   44
CONECT   20   21   45
CONECT   21   22   46   47
CONECT   22   23   48   49
CONECT   23   24   50
CONECT   24   51
END

HMDB0254825
     RDKit          3D
Modrastane
 51 55  0  0  0  0  0  0  0  0999 V2000
   -2.5811    1.6243    1.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4188    0.3737    0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7218   -0.7261    1.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396   -0.5490    1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3265   -0.0240    0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549   -0.2739   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.0627   -2.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3020   -0.3465   -2.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885    0.0940   -1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2474    1.5333   -1.0789 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4160    0.6772   -1.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3205    0.5961   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646    1.0072   -0.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190    0.1447    1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8528    0.0806    2.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5878    0.0416    3.0395 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5590   -0.3153    1.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7127   -0.5539    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760   -2.0584   -0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8067    0.7131   -0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587    0.6137   -1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1839    0.5834   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8202   -0.1200    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7150   -1.5007    0.2830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683    1.9081    2.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8007    2.4654    0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4144    1.5002    2.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1129   -0.6840    2.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0141   -1.7381    1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2008   -1.5809    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0068    0.1035    2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311    1.0790    0.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689   -1.3004   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4304    0.9498   -2.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -0.7696   -2.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4716   -1.4188   -2.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6424    0.2262   -3.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215    0.8467   -2.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8318    2.0072   -0.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0776    0.4490    1.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390   -1.2299    1.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7574   -2.3566   -0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8010   -2.5921    0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5487   -2.3710   -0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3487    1.7350   -0.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144   -0.2420   -2.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8201    1.5715   -2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5693    1.5709   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232    0.0122   -1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393    0.0440    1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240   -1.7377   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
  6 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 20  2  1  0
 23  2  1  0
 18  5  1  0
 11  9  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 11 38  1  0
 13 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₇NO₃

Average Molecular Weight

329.44

Monoisotopic Molecular Weight

329.199093733

IUPAC Name

5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile

Traditional Name

5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CCC45OC4C(O)=C(CC35C)C#N)C1CCC2O

InChI Identifier

InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3

InChI Key

KVJXBPDAXMEYOA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

Estrane-skeleton
Cyclic alcohol
Secondary alcohol
Dialkyl ether
Enol
Oxirane
Ether
Carbonitrile
Nitrile
Organoheterocyclic compound
Oxacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.41	ALOGPS
logP	2.3	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.23	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.17 m³·mol⁻¹	ChemAxon
Polarizability	36.85 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	213.265	30932474
DeepCCS	[M+Na]+	188.565	30932474
AllCCS	[M+H]+	182.0	32859911
AllCCS	[M+H-H2O]+	179.2	32859911
AllCCS	[M+NH4]+	184.6	32859911
AllCCS	[M+Na]+	185.3	32859911
AllCCS	[M-H]-	185.7	32859911
AllCCS	[M+Na-2H]-	185.6	32859911
AllCCS	[M+HCOO]-	185.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Modrastane	CC12CCC3C(CCC45OC4C(O)=C(CC35C)C#N)C1CCC2O	3325.5	Standard polar	33892256
Modrastane	CC12CCC3C(CCC45OC4C(O)=C(CC35C)C#N)C1CCC2O	2631.8	Standard non polar	33892256
Modrastane	CC12CCC3C(CCC45OC4C(O)=C(CC35C)C#N)C1CCC2O	3051.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Modrastane,1TMS,isomer #1	CC12CCC3C(CCC45OC4C(O[Si](C)(C)C)=C(C#N)CC35C)C1CCC2O	3019.7	Semi standard non polar	33892256
Modrastane,1TMS,isomer #1	CC12CCC3C(CCC45OC4C(O[Si](C)(C)C)=C(C#N)CC35C)C1CCC2O	2811.4	Standard non polar	33892256
Modrastane,1TMS,isomer #1	CC12CCC3C(CCC45OC4C(O[Si](C)(C)C)=C(C#N)CC35C)C1CCC2O	3490.9	Standard polar	33892256
Modrastane,1TBDMS,isomer #1	CC12CCC3C(CCC45OC4C(O[Si](C)(C)C(C)(C)C)=C(C#N)CC35C)C1CCC2O	3270.5	Semi standard non polar	33892256
Modrastane,1TBDMS,isomer #1	CC12CCC3C(CCC45OC4C(O[Si](C)(C)C(C)(C)C)=C(C#N)CC35C)C1CCC2O	3078.1	Standard non polar	33892256
Modrastane,1TBDMS,isomer #1	CC12CCC3C(CCC45OC4C(O[Si](C)(C)C(C)(C)C)=C(C#N)CC35C)C1CCC2O	3653.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Modrastane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ir0-3497000000-5404a18ca29d1e31f229	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Modrastane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Modrastane GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Modrastane GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Modrastane GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Modrastane GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Modrastane 10V, Positive-QTOF	splash10-001i-0009000000-3204f0db80f7010d2c5b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Modrastane 20V, Positive-QTOF	splash10-03di-2279000000-66f6663f387c9f220d00	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Modrastane 40V, Positive-QTOF	splash10-0ue9-3490000000-2ca4ad351b4836b77e35	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Modrastane 10V, Negative-QTOF	splash10-004i-0009000000-93fb7ff56b0b7a4bf0f2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Modrastane 20V, Negative-QTOF	splash10-01t9-0009000000-019ee62ca984d8cd6f48	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Modrastane 40V, Negative-QTOF	splash10-004i-0049000000-f63dd965219650a217fe	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

466184

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trilostane

METLIN ID

Not Available

PubChem Compound

535161

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Modrastane (HMDB0254825)

MOL for HMDB0254825 (Modrastane)

3D MOL for HMDB0254825 (Modrastane)

3D SDF for HMDB0254825 (Modrastane)

3D-SDF for HMDB0254825 (Modrastane)

PDB for HMDB0254825 (Modrastane)

3D PDB for HMDB0254825 (Modrastane)

SMILES for HMDB0254825 (Modrastane)

INCHI for HMDB0254825 (Modrastane)

Structure for HMDB0254825 (Modrastane)

3D Structure for HMDB0254825 (Modrastane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra