Oripavine

Details

• Internal ID: b6a35a04-cc37-40f1-958c-d133cd9f0e14
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: (4R,7aR,12bS)-7-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol
• SMILES (Canonical): CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)O)O4)OC
• SMILES (Isomeric): CN1CC[C@]23[C@@H]4C(=CC=C2[C@H]1CC5=C3C(=C(C=C5)O)O4)OC
• InChI: InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-6-14(21-2)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,12,17,20H,7-9H2,1-2H3/t12-,17+,18+/m1/s1
• InChI Key: ZKLXUUYLEHCAMF-UUWFMWQGSA-N
• Popularity: 224 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.30 g/mol
• Exact Mass: 297.13649347 g/mol
• Topological Polar Surface Area (TPSA): 41.90 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 467-04-9
• EINECS 207-385-6
• BRN 0046094
• UNII-575AOU51CR
• 575AOU51CR
• CHEBI:7782
• (5alpha)-6,7,8,14-Tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol
• 6,7,8,14-Tetradehydro-4,5-alpha-epoxy-6-methoxy-17-methyl-morphinan-3-ol
• 3-O-Demethylthebaine
• 4-27-00-02270 (Beilstein Handbook Reference)
• Morphinan-3-ol, 6,7,8,14-tetradehydro-4,5-alpha-epoxy-6-methoxy-17-methyl-
• 6,7,8,14-Tetradehydro-4,5alpha-epoxy-6-methoxy-17-methylmorphinan-3-ol (Oripavine)
• O3-demethylthe-baine
• ORIPAVINE [MI]
• D05YXS
• SCHEMBL37889
• CHEMBL437602
• IDS-NO-010
• DEA No. 9330
• SCHEMBL19880919
• HSDB 8324
• DTXSID10196908
• Morphinan-3-ol, 6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methyl-, (5.alpha.)-
• Oripavine 0.1 mg/ml in Methanol
• ZKLXUUYLEHCAMF-UUWFMWQGSA-N
• (4R,7aR,12bS)-7-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-ol
• LS-92074
• C06175
• MORPHINE SULFATE IMPURITY C [EP IMPURITY]
• Q420639
• CODEINE MONOHYDRATE IMPURITY L [EP IMPURITY]
• CODEINE HYDROCHLORIDE DIHYDRATE IMPURITY L [EP IMPURITY]
• CODEINE PHOSPHATE HEMIHYDRATE IMPURITY L [EP IMPURITY]
• (5-alpha)-6,7,8,14-Tetrahydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol
• 6,7,8,14-TETRADEHYDRO-4,5.ALPHA.-EPOXY-6-METHOXY-17-METHYLMORPHINAN-3-OL
• Morphinan-3-ol, 6,7,8-,14-tetradehydro-4,5-epoxy-6-methoxy-17-methyl, (5.alpha.)-
• (1S,5R,13R)-14-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0?,??.0?,??.0?,??]octadeca-7,9,11(18),14,16-pentaen-10-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	+	0.9161	91.61%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5781	57.81%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9103	91.03%
OATP1B3 inhibitior	+	0.9513	95.13%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8555	85.55%
P-glycoprotein inhibitior	-	0.8699	86.99%
P-glycoprotein substrate	+	0.7265	72.65%
CYP3A4 substrate	+	0.6709	67.09%
CYP2C9 substrate	-	0.5700	57.00%
CYP2D6 substrate	+	0.6151	61.51%
CYP3A4 inhibition	-	0.8296	82.96%
CYP2C9 inhibition	-	0.8782	87.82%
CYP2C19 inhibition	-	0.8578	85.78%
CYP2D6 inhibition	+	0.6803	68.03%
CYP1A2 inhibition	-	0.6840	68.40%
CYP2C8 inhibition	-	0.8531	85.31%
CYP inhibitory promiscuity	-	0.7083	70.83%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6815	68.15%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9860	98.60%
Skin irritation	-	0.7703	77.03%
Skin corrosion	-	0.9308	93.08%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5871	58.71%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8048	80.48%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7329	73.29%
Acute Oral Toxicity (c)	II	0.7018	70.18%
Estrogen receptor binding	-	0.4866	48.66%
Androgen receptor binding	-	0.7794	77.94%
Thyroid receptor binding	+	0.6137	61.37%
Glucocorticoid receptor binding	-	0.4670	46.70%
Aromatase binding	-	0.6252	62.52%
PPAR gamma	+	0.5695	56.95%
Honey bee toxicity	-	0.8092	80.92%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9186	91.86%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL233	P35372	Mu opioid receptor	277 nM; 277 nM	EC50; EC50	via Super-PRED; PMID: 17616524

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.30%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.39%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.73%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.54%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.54%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.80%	91.03%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.76%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.71%	85.14%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.82%	89.05%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.30%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.58%	97.09%
CHEMBL217	P14416	Dopamine D2 receptor	82.55%	95.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.43%	94.00%
CHEMBL236	P41143	Delta opioid receptor	80.93%	99.35%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.11%	85.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.04%	100.00%

Plants that contains it

• Aloe microstigma
• Berberis nervosa
• Chrozophora plicata
• Papaver bracteatum
• Papaver orientale
• Papaver pinnatifidum
• Papaver somniferum

Cross-Links

• PubChem: 5462306
• NPASS: NPC124657
• ChEMBL: CHEMBL437602
• LOTUS: LTS0016304
• wikiData: Q420639