norbuprenorphine

ID: ALA1743323

Cas Number: 78715-23-8

PubChem CID: 114976

Max Phase: Phase

Molecular Formula: C25H35NO4

Molecular Weight: 413.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Norbuprenorphine | Norbuprenorphine|78715-23-8|Des(cyclopropylmethyl)buprenorphine|7E53B4O073|(1S,2S,6R,14R,15R,16R)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol|6,14-Ethenomorphinan-7-methanol, alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-, (alphaS,5alpha,7alpha)-|UNII-7E53B4O073|BUPRENORPHINE IMPURITY B|CHEMBL1743323|SCHEMBL14408877|DTXSID60891436|CHEBI:172315|YOYLLRBShow More⌵

Canonical SMILES:  CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1Cc4ccc(O)c5c4[C@@]3(CCN1)[C@H]2O5

Standard InChI:  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

Standard InChI Key:  YOYLLRBMGQRFTN-IOMBULRVSA-N

Molfile:  

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    5.2298    3.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2402    3.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7667    1.2144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205    2.4519    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0232    3.7319    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  9 33  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1743323

   NORBUPRENORPHINE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 413.56

Molecular Weight (Monoisotopic): 413.2566

AlogP: 3.29

#Rotatable Bonds: 2

Polar Surface Area: 70.95

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.80

CX Basic pKa: 10.49

CX LogP: 2.30

CX LogD: 0.29

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.69

Np Likeness Score: 2.05

References

1.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 

2. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

3. Kiang TK, Ensom MH, Chang TK..  (2005)  UDP-glucuronosyltransferases and clinical drug-drug interactions.,  106  (1): [PMID:15781124] [10.1016/j.pharmthera.2004.10.013]

4. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Clinical Candidates