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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:33:21 UTC

Update Date

2021-09-14 15:44:46 UTC

HMDB ID

HMDB0060546

Secondary Accession Numbers

HMDB60546

Metabolite Identification

Common Name

Norbuprenorphine

Description

Norbuprenorphine is the primary active metabolite of buprenorphine. Norbuprenorphine acts as a Î¼-opioid, Î´-opioid, and nociceptin receptor full agonist, as well as a Îº-opioid receptor partial agonist. Norbuprenorphine crosses the blood-brain-barrier similarly to buprenorphine and likely contributes to its effects. It was observed that Intravenous administration of norbuprenorphine at 1 to 3 mg/kg decreased respiratory rate, whereas buprenorphine had no effect up to 3 mg/kg in rats. (Wikipedia )

Structure

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

644073
  Mrv0541 02271201082D          

 30 35  0  0  1  0            999 V2000
    4.3077   -2.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3942   -2.4224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2342   -0.1130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2396   -2.4224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418    1.1755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418   -0.2533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7293   -0.9678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9668   -1.6822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1418   -1.6822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3794   -0.9678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9668   -0.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293    0.4612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7376   -0.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4260   -1.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169   -0.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044   -0.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044    0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2342   -0.9678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3077    1.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918   -0.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918   -1.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0889   -0.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2342   -1.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -0.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -1.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9668   -3.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -0.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9437   -0.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0889   -1.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0889   -0.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
  1 21  1  0  0  0  0
  8  2  1  6  0  0  0
  2 26  1  0  0  0  0
 18  3  1  1  0  0  0
  4 25  1  0  0  0  0
 12  5  1  1  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  6  0  0  0
  7  9  1  0  0  0  0
  7 15  1  1  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  6  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 16 21  1  0  0  0  0
 17 20  1  0  0  0  0
 18 22  1  0  0  0  0
 18 23  1  1  0  0  0
 20 24  1  0  0  0  0
 21 25  2  0  0  0  0
 22 28  1  0  0  0  0
 22 29  1  0  0  0  0
 22 30  1  0  0  0  0
 24 27  2  0  0  0  0
 25 27  1  0  0  0  0
M  END

HMDB0060546
     RDKit          3D
Norbuprenorphine
 65 70  0  0  0  0  0  0  0  0999 V2000
    0.1540    3.2523    1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8425    2.3328    0.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3009    1.1383    0.4083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1298    0.2938    1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5861   -1.0491    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430   -1.0342   -0.4835 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5708   -0.8114   -1.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2134    0.4025   -0.5962 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6496    0.4262   -0.3993 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1307    1.8963   -0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    0.0564   -1.6999 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4609   -0.3909    0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4231   -1.8957    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714   -0.2162    1.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419   -0.0950    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -2.2464   -0.9543 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9016   -2.3788   -0.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234   -1.1870    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4983   -1.1662    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8334    0.0140    1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0666    1.1714    1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3845    2.3452    2.2444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9738    1.1681    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7466   -0.0074    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6153    0.1500   -0.8307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1362    0.2040   -2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310   -1.0973   -2.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -2.1690   -2.4233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527    1.4276   -0.3822 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9861    2.0919    0.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855    4.1216    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1752    2.9822    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585    3.7979    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    0.1672    2.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0204    0.7586    2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763   -1.7548    1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292   -1.4755    1.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -0.7225   -2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130   -1.7162   -1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0656    1.1754   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1599    1.9832   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686    2.3125    0.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5160    2.4845   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7012    0.5776   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5238   -2.3169    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5242   -2.1614   -0.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500   -2.3364    0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4641   -0.4019    2.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8051   -0.9600    2.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569    0.7594    2.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2582    0.8758    0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5529   -0.8539    0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958   -0.2531   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239   -3.1623   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762   -3.2749    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5896   -2.5937   -1.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0782   -2.0538    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6928    0.0342    2.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560    3.1960    2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6396    0.9980   -2.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2031    0.5960   -2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9148   -0.9189   -3.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2732   -1.4746   -2.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7879   -3.0590   -2.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304    2.0432   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  6
 26 27  1  0
 27 28  1  0
 25 29  1  0
 29 30  1  0
  8  3  1  0
 28 16  1  0
 29  3  1  0
 25  6  1  0
 24 18  1  0
 30 23  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  6
 10 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  6
 17 55  1  0
 17 56  1  0
 19 57  1  0
 20 58  1  0
 22 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 29 65  1  6
M  END

644073
  Mrv0541 02271201082D          

 30 35  0  0  1  0            999 V2000
    4.3077   -2.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3942   -2.4224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2342   -0.1130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2396   -2.4224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418    1.1755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418   -0.2533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7293   -0.9678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9668   -1.6822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1418   -1.6822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3794   -0.9678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9668   -0.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293    0.4612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7376   -0.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4260   -1.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169   -0.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044   -0.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9044    0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2342   -0.9678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3077    1.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918   -0.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918   -1.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0889   -0.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2342   -1.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -0.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -1.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9668   -3.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -0.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9437   -0.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0889   -1.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0889   -0.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
  1 21  1  0  0  0  0
  8  2  1  6  0  0  0
  2 26  1  0  0  0  0
 18  3  1  1  0  0  0
  4 25  1  0  0  0  0
 12  5  1  1  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  6  0  0  0
  7  9  1  0  0  0  0
  7 15  1  1  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  6  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 16 21  1  0  0  0  0
 17 20  1  0  0  0  0
 18 22  1  0  0  0  0
 18 23  1  1  0  0  0
 20 24  1  0  0  0  0
 21 25  2  0  0  0  0
 22 28  1  0  0  0  0
 22 29  1  0  0  0  0
 22 30  1  0  0  0  0
 24 27  2  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060546

> <DATABASE_NAME>
hmdb

> <SMILES>
CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=C5C(O[C@@H]2[C@@]35CCN1)=C(O)C=C4

> <INCHI_IDENTIFIER>
InChI=1S/C25H35NO4/c1-21(2,3)22(4,28)16-13-23-8-9-25(16,29-5)20-24(23)10-11-26-17(23)12-14-6-7-15(27)19(30-20)18(14)24/h6-7,16-17,20,26-28H,8-13H2,1-5H3/t16-,17-,20-,22+,23-,24+,25-/m1/s1

> <INCHI_KEY>
YOYLLRBMGQRFTN-IOMBULRVSA-N

> <FORMULA>
C25H35NO4

> <MOLECULAR_WEIGHT>
413.5497

> <EXACT_MASS>
413.256608613

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.94592042848156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,6S,14R,15R,16R)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
2.3001822872115905

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.298035225750233

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.796365754935364

> <JCHEM_PKA_STRONGEST_BASIC>
10.490180324560464

> <JCHEM_POLAR_SURFACE_AREA>
70.95

> <JCHEM_REFRACTIVITY>
114.52560000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6S,14R,15R,16R)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060546
     RDKit          3D
Norbuprenorphine
 65 70  0  0  0  0  0  0  0  0999 V2000
    0.1540    3.2523    1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8425    2.3328    0.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3009    1.1383    0.4083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1298    0.2938    1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5861   -1.0491    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430   -1.0342   -0.4835 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5708   -0.8114   -1.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2134    0.4025   -0.5962 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6496    0.4262   -0.3993 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1307    1.8963   -0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    0.0564   -1.6999 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4609   -0.3909    0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4231   -1.8957    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714   -0.2162    1.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419   -0.0950    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -2.2464   -0.9543 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9016   -2.3788   -0.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234   -1.1870    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4983   -1.1662    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8334    0.0140    1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0666    1.1714    1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3845    2.3452    2.2444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9738    1.1681    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7466   -0.0074    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6153    0.1500   -0.8307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1362    0.2040   -2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310   -1.0973   -2.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -2.1690   -2.4233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527    1.4276   -0.3822 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9861    2.0919    0.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855    4.1216    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1752    2.9822    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585    3.7979    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    0.1672    2.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0204    0.7586    2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763   -1.7548    1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292   -1.4755    1.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -0.7225   -2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130   -1.7162   -1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0656    1.1754   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1599    1.9832   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686    2.3125    0.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5160    2.4845   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7012    0.5776   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5238   -2.3169    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5242   -2.1614   -0.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500   -2.3364    0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4641   -0.4019    2.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8051   -0.9600    2.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569    0.7594    2.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2582    0.8758    0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5529   -0.8539    0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958   -0.2531   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239   -3.1623   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762   -3.2749    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5896   -2.5937   -1.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0782   -2.0538    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6928    0.0342    2.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560    3.1960    2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6396    0.9980   -2.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2031    0.5960   -2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9148   -0.9189   -3.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2732   -1.4746   -2.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7879   -3.0590   -2.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304    2.0432   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  6
 26 27  1  0
 27 28  1  0
 25 29  1  0
 29 30  1  0
  8  3  1  0
 28 16  1  0
 29  3  1  0
 25  6  1  0
 24 18  1  0
 30 23  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  6
 10 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  6
 17 55  1  0
 17 56  1  0
 19 57  1  0
 20 58  1  0
 22 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 29 65  1  6
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 644073                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       8.041  -4.202   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.936  -4.522   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.504  -0.211   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.181  -4.522   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.598   2.194   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.598  -0.473   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.828  -1.807   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.138  -3.140   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.598  -3.140   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.908  -1.807   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.138  -0.473   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.828   0.861   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.710  -1.191   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.129  -2.354   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.058  -0.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.288  -1.807   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.288   0.861   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.504  -1.807   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.041   2.471   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.518  -0.473   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.518  -3.140   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.099  -1.807   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.504  -3.402   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.978  -0.473   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.978  -3.140   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.138  -5.904   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.208  -1.807   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.695  -1.807   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.099  -3.402   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.099  -0.211   0.000  0.00  0.00           C+0
CONECT    1    9   21                                                       
CONECT    2    8   26                                                       
CONECT    3   18                                                            
CONECT    4   25                                                            
CONECT    5   12   19                                                       
CONECT    6    7   11   12   13                                             
CONECT    7    6    9   15   16                                             
CONECT    8    2    9   10   14                                             
CONECT    9    1    7    8                                                  
CONECT   10    8   11   18                                                  
CONECT   11    6   10                                                       
CONECT   12    5    6   17                                                  
CONECT   13    6   14                                                       
CONECT   14    8   13                                                       
CONECT   15    7   19                                                       
CONECT   16    7   20   21                                                  
CONECT   17   12   20                                                       
CONECT   18    3   10   22   23                                             
CONECT   19    5   15                                                       
CONECT   20   16   17   24                                                  
CONECT   21    1   16   25                                                  
CONECT   22   18   28   29   30                                             
CONECT   23   18                                                            
CONECT   24   20   27                                                       
CONECT   25    4   21   27                                                  
CONECT   26    2                                                            
CONECT   27   24   25                                                       
CONECT   28   22                                                            
CONECT   29   22                                                            
CONECT   30   22                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

COMPND    HMDB0060546
HETATM    1  C1  UNL     1       0.154   3.252   1.438  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.842   2.333   0.744  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.301   1.138   0.408  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.130   0.294   1.547  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.586  -1.049   1.013  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.743  -1.034  -0.483  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.571  -0.811  -1.170  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.213   0.403  -0.596  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.650   0.426  -0.399  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.131   1.896  -0.418  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.192   0.056  -1.700  1.00  0.00           O  
HETATM   12  C10 UNL     1       3.461  -0.391   0.474  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.423  -1.896   0.236  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.471  -0.216   1.945  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.942  -0.095   0.071  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.473  -2.246  -0.954  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.902  -2.379  -0.494  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.423  -1.187   0.215  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.498  -1.166   1.059  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.833   0.014   1.746  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.067   1.171   1.571  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.384   2.345   2.244  1.00  0.00           O  
HETATM   23  C20 UNL     1      -2.974   1.168   0.720  1.00  0.00           C  
HETATM   24  C21 UNL     1      -2.747  -0.007   0.110  1.00  0.00           C  
HETATM   25  C22 UNL     1      -1.615   0.150  -0.831  1.00  0.00           C  
HETATM   26  C23 UNL     1      -2.136   0.204  -2.209  1.00  0.00           C  
HETATM   27  C24 UNL     1      -2.231  -1.097  -2.909  1.00  0.00           C  
HETATM   28  N1  UNL     1      -1.427  -2.169  -2.423  1.00  0.00           N  
HETATM   29  C25 UNL     1      -0.953   1.428  -0.382  1.00  0.00           C  
HETATM   30  O4  UNL     1      -1.986   2.092   0.308  1.00  0.00           O  
HETATM   31  H1  UNL     1       0.885   4.122   1.603  1.00  0.00           H  
HETATM   32  H2  UNL     1      -0.175   2.982   2.451  1.00  0.00           H  
HETATM   33  H3  UNL     1      -0.658   3.798   0.860  1.00  0.00           H  
HETATM   34  H4  UNL     1       0.688   0.167   2.293  1.00  0.00           H  
HETATM   35  H5  UNL     1      -1.020   0.759   2.027  1.00  0.00           H  
HETATM   36  H6  UNL     1       0.276  -1.755   1.209  1.00  0.00           H  
HETATM   37  H7  UNL     1      -1.429  -1.475   1.534  1.00  0.00           H  
HETATM   38  H8  UNL     1       0.300  -0.723  -2.270  1.00  0.00           H  
HETATM   39  H9  UNL     1       1.213  -1.716  -1.177  1.00  0.00           H  
HETATM   40  H10 UNL     1       1.066   1.175  -1.455  1.00  0.00           H  
HETATM   41  H11 UNL     1       4.160   1.983  -0.823  1.00  0.00           H  
HETATM   42  H12 UNL     1       3.169   2.313   0.597  1.00  0.00           H  
HETATM   43  H13 UNL     1       2.516   2.485  -1.131  1.00  0.00           H  
HETATM   44  H14 UNL     1       2.701   0.578  -2.382  1.00  0.00           H  
HETATM   45  H15 UNL     1       2.524  -2.317   0.724  1.00  0.00           H  
HETATM   46  H16 UNL     1       3.524  -2.161  -0.829  1.00  0.00           H  
HETATM   47  H17 UNL     1       4.350  -2.336   0.717  1.00  0.00           H  
HETATM   48  H18 UNL     1       4.464  -0.402   2.415  1.00  0.00           H  
HETATM   49  H19 UNL     1       2.805  -0.960   2.475  1.00  0.00           H  
HETATM   50  H20 UNL     1       3.157   0.759   2.323  1.00  0.00           H  
HETATM   51  H21 UNL     1       5.258   0.876   0.476  1.00  0.00           H  
HETATM   52  H22 UNL     1       5.553  -0.854   0.605  1.00  0.00           H  
HETATM   53  H23 UNL     1       5.096  -0.253  -0.993  1.00  0.00           H  
HETATM   54  H24 UNL     1      -0.924  -3.162  -0.680  1.00  0.00           H  
HETATM   55  H25 UNL     1      -2.976  -3.275   0.189  1.00  0.00           H  
HETATM   56  H26 UNL     1      -3.590  -2.594  -1.346  1.00  0.00           H  
HETATM   57  H27 UNL     1      -5.078  -2.054   1.190  1.00  0.00           H  
HETATM   58  H28 UNL     1      -5.693   0.034   2.420  1.00  0.00           H  
HETATM   59  H29 UNL     1      -3.856   3.196   2.143  1.00  0.00           H  
HETATM   60  H30 UNL     1      -1.640   0.998  -2.831  1.00  0.00           H  
HETATM   61  H31 UNL     1      -3.203   0.596  -2.143  1.00  0.00           H  
HETATM   62  H32 UNL     1      -1.915  -0.919  -3.973  1.00  0.00           H  
HETATM   63  H33 UNL     1      -3.273  -1.475  -2.999  1.00  0.00           H  
HETATM   64  H34 UNL     1      -1.788  -3.059  -2.811  1.00  0.00           H  
HETATM   65  H35 UNL     1      -0.730   2.043  -1.287  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3
CONECT    3    4    8   29
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7   16   25
CONECT    7    8   38   39
CONECT    8    9   40
CONECT    9   10   11   12
CONECT   10   41   42   43
CONECT   11   44
CONECT   12   13   14   15
CONECT   13   45   46   47
CONECT   14   48   49   50
CONECT   15   51   52   53
CONECT   16   17   28   54
CONECT   17   18   55   56
CONECT   18   19   19   24
CONECT   19   20   57
CONECT   20   21   21   58
CONECT   21   22   23
CONECT   22   59
CONECT   23   24   24   30
CONECT   24   25
CONECT   25   26   29
CONECT   26   27   60   61
CONECT   27   28   62   63
CONECT   28   64
CONECT   29   30   65
END

HMDB0060546
     RDKit          3D
Norbuprenorphine
 65 70  0  0  0  0  0  0  0  0999 V2000
    0.1540    3.2523    1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8425    2.3328    0.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3009    1.1383    0.4083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1298    0.2938    1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5861   -1.0491    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430   -1.0342   -0.4835 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5708   -0.8114   -1.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2134    0.4025   -0.5962 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6496    0.4262   -0.3993 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1307    1.8963   -0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    0.0564   -1.6999 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4609   -0.3909    0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4231   -1.8957    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714   -0.2162    1.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419   -0.0950    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -2.2464   -0.9543 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9016   -2.3788   -0.4937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234   -1.1870    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4983   -1.1662    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8334    0.0140    1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0666    1.1714    1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3845    2.3452    2.2444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9738    1.1681    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7466   -0.0074    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6153    0.1500   -0.8307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1362    0.2040   -2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310   -1.0973   -2.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -2.1690   -2.4233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527    1.4276   -0.3822 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9861    2.0919    0.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855    4.1216    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1752    2.9822    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585    3.7979    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    0.1672    2.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0204    0.7586    2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763   -1.7548    1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292   -1.4755    1.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -0.7225   -2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130   -1.7162   -1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0656    1.1754   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1599    1.9832   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686    2.3125    0.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5160    2.4845   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7012    0.5776   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5238   -2.3169    0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5242   -2.1614   -0.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500   -2.3364    0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4641   -0.4019    2.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8051   -0.9600    2.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569    0.7594    2.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2582    0.8758    0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5529   -0.8539    0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958   -0.2531   -0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239   -3.1623   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762   -3.2749    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5896   -2.5937   -1.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0782   -2.0538    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6928    0.0342    2.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560    3.1960    2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6396    0.9980   -2.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2031    0.5960   -2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9148   -0.9189   -3.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2732   -1.4746   -2.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7879   -3.0590   -2.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304    2.0432   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  6
 26 27  1  0
 27 28  1  0
 25 29  1  0
 29 30  1  0
  8  3  1  0
 28 16  1  0
 29  3  1  0
 25  6  1  0
 24 18  1  0
 30 23  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  6
 10 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  6
 17 55  1  0
 17 56  1  0
 19 57  1  0
 20 58  1  0
 22 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 29 65  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Des(cyclopropylmethyl)buprenorphine	HMDB
N-Desalkylbuprenorphine	HMDB

Chemical Formula

C₂₅H₃₅NO₄

Average Molecular Weight

413.5497

Monoisotopic Molecular Weight

413.256608613

IUPAC Name

(1S,2R,6S,14R,15R,16R)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol

Traditional Name

(1S,2R,6S,14R,15R,16R)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol

CAS Registry Number

Not Available

SMILES

CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=C5C(O[C@@H]2[C@@]35CCN1)=C(O)C=C4

InChI Identifier

InChI=1S/C25H35NO4/c1-21(2,3)22(4,28)16-13-23-8-9-25(16,29-5)20-24(23)10-11-26-17(23)12-14-6-7-15(27)19(30-20)18(14)24/h6-7,16-17,20,26-28H,8-13H2,1-5H3/t16-,17-,20-,22+,23-,24+,25-/m1/s1

InChI Key

YOYLLRBMGQRFTN-IOMBULRVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Azaspirodecane
Tetralin
Coumaran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Tertiary alcohol
Dialkyl ether
Secondary aliphatic amine
Ether
Secondary amine
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Amine
Organooxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0060546)
Kidney (HMDB: HMDB0060546)

Biofluid or Excreta

Non-excretory biofluid

Blood (HMDB: HMDB0060546)

Excreta

Urine (HMDB: HMDB0060546)

Cellular substructure

Cytoplasm (HMDB: HMDB0060546)
Membrane (HMDB: HMDB0060546)

Process

Not Available

Role

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
Water Solubility	0.026 g/L	ALOGPS
logP	3.19	ALOGPS
logP	2.3	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.8	ChemAxon
pKa (Strongest Basic)	10.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	70.95 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	114.53 m³·mol⁻¹	ChemAxon
Polarizability	45.95 Å³	ChemAxon
Number of Rings	6	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
DarkChem	[M+H]+	194.948	31661259
DarkChem	[M-H]-	190.368	31661259
DeepCCS	[M-2H]-	239.729	30932474
DeepCCS	[M+Na]+	214.161	30932474
AllCCS	[M+H]+	198.0	32859911
AllCCS	[M+H-H2O]+	195.7	32859911
AllCCS	[M+NH4]+	200.0	32859911
AllCCS	[M+Na]+	200.6	32859911
AllCCS	[M-H]-	207.3	32859911
AllCCS	[M+Na-2H]-	208.0	32859911
AllCCS	[M+HCOO]-	208.8	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norbuprenorphine,1TMS,isomer #1	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1)[C@H]2O5	3068.2	Semi standard non polar	33892256
Norbuprenorphine,1TMS,isomer #2	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1)[C@H]2O5	3120.3	Semi standard non polar	33892256
Norbuprenorphine,1TMS,isomer #3	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O5	3076.9	Semi standard non polar	33892256
Norbuprenorphine,2TMS,isomer #1	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1)[C@H]2O5	3094.8	Semi standard non polar	33892256
Norbuprenorphine,2TMS,isomer #2	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O5	3056.0	Semi standard non polar	33892256
Norbuprenorphine,2TMS,isomer #3	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O5	3093.2	Semi standard non polar	33892256
Norbuprenorphine,3TMS,isomer #1	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O5	3131.5	Semi standard non polar	33892256
Norbuprenorphine,3TMS,isomer #1	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O5	3386.3	Standard non polar	33892256
Norbuprenorphine,3TMS,isomer #1	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O5	3281.2	Standard polar	33892256
Norbuprenorphine,1TBDMS,isomer #1	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1)[C@H]2O5	3321.0	Semi standard non polar	33892256
Norbuprenorphine,1TBDMS,isomer #2	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1)[C@H]2O5	3342.4	Semi standard non polar	33892256
Norbuprenorphine,1TBDMS,isomer #3	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O5	3285.2	Semi standard non polar	33892256
Norbuprenorphine,2TBDMS,isomer #1	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1)[C@H]2O5	3527.7	Semi standard non polar	33892256
Norbuprenorphine,2TBDMS,isomer #2	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O5	3500.8	Semi standard non polar	33892256
Norbuprenorphine,2TBDMS,isomer #3	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O5	3521.0	Semi standard non polar	33892256
Norbuprenorphine,3TBDMS,isomer #1	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O5	3764.3	Semi standard non polar	33892256
Norbuprenorphine,3TBDMS,isomer #1	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O5	4023.3	Standard non polar	33892256
Norbuprenorphine,3TBDMS,isomer #1	CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O5	3540.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norbuprenorphine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9135000000-45e0d329ab9294ed4317	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbuprenorphine GC-MS (2 TMS) - 70eV, Positive	splash10-05g3-9001010000-5c6c16b735846e565925	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbuprenorphine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbuprenorphine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbuprenorphine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbuprenorphine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbuprenorphine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbuprenorphine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbuprenorphine GC-MS ("Norbuprenorphine,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine LC-ESI-QTOF , positive-QTOF	splash10-03di-0000900000-d0e136497c0156c9680f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine LC-ESI-QTOF , positive-QTOF	splash10-03di-0000900000-b04b0200f02b897bb6ef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine LC-ESI-QTOF , positive-QTOF	splash10-03di-0000900000-18c86464a0d8a8e11bf8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine LC-ESI-QTOF , positive-QTOF	splash10-03di-0143900000-52c84cfc3c7de4f83891	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine LC-ESI-QTOF , positive-QTOF	splash10-03dr-0490100000-61fc9d6ff83269e9fe09	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 50V, Positive-QTOF	splash10-03ki-0691100000-b93b4447efa37aa300b0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 40V, Positive-QTOF	splash10-03di-0263900000-362c7ffa1fc4db260e07	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 50V, Positive-QTOF	splash10-03ki-0691100000-cc22b459c3503e03c2de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 30V, Positive-QTOF	splash10-03di-0000900000-a17b5bb24d801a8703c5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 20V, Positive-QTOF	splash10-03di-0000900000-7f319d742b7c88e6d294	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 50V, Positive-QTOF	splash10-03dr-0490100000-61fc9d6ff83269e9fe09	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 10V, Positive-QTOF	splash10-03di-0000900000-e8bb505ed3edc3b3f233	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 20V, Positive-QTOF	splash10-03di-0000900000-b04b0200f02b897bb6ef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 10V, Positive-QTOF	splash10-03di-0000900000-d0e136497c0156c9680f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 30V, Positive-QTOF	splash10-03di-0000900000-18c86464a0d8a8e11bf8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norbuprenorphine 40V, Positive-QTOF	splash10-03di-0143900000-52c84cfc3c7de4f83891	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbuprenorphine 10V, Positive-QTOF	splash10-01ot-0009500000-f9107c3bc2684b887bb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbuprenorphine 20V, Positive-QTOF	splash10-01ot-1009200000-5c2addf9f89749701055	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbuprenorphine 40V, Positive-QTOF	splash10-001i-4109000000-29b63bd2b3e8e8942b95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbuprenorphine 10V, Negative-QTOF	splash10-03di-0003900000-96dbf2e34e2566985c4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbuprenorphine 20V, Negative-QTOF	splash10-03di-2129500000-c9958eaf16725890f647	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbuprenorphine 40V, Negative-QTOF	splash10-0002-1194000000-e835394a1e996708aa1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbuprenorphine 10V, Positive-QTOF	splash10-03di-0000900000-22add0760b63a0f18d04	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbuprenorphine 20V, Positive-QTOF	splash10-03di-0001900000-bf64a5b4def2ecf8bf30	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbuprenorphine 40V, Positive-QTOF	splash10-03di-0003900000-17c40c03c2942ffaf0ba	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norbuprenorphine

METLIN ID

Not Available

PubChem Compound

114976

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

Not Available

Showing metabocard for Norbuprenorphine (HMDB0060546)

MOL for HMDB0060546 (Norbuprenorphine)

3D MOL for HMDB0060546 (Norbuprenorphine)

3D SDF for HMDB0060546 (Norbuprenorphine)

3D-SDF for HMDB0060546 (Norbuprenorphine)

PDB for HMDB0060546 (Norbuprenorphine)

3D PDB for HMDB0060546 (Norbuprenorphine)

SMILES for HMDB0060546 (Norbuprenorphine)

INCHI for HMDB0060546 (Norbuprenorphine)

Structure for HMDB0060546 (Norbuprenorphine)

3D Structure for HMDB0060546 (Norbuprenorphine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra