Dihydromorphine

Details

• Internal ID: 6d57a113-1a8d-4d8f-bc23-93244da2f894
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: (4R,4aR,7S,7aR,12bS)-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
• SMILES (Canonical): CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(CC4)O
• SMILES (Isomeric): CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3[C@H](CC4)O
• InChI: InChI=1S/C17H21NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1
• InChI Key: IJVCSMSMFSCRME-KBQPJGBKSA-N
• Popularity: 386 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.35 g/mol
• Exact Mass: 287.15214353 g/mol
• Topological Polar Surface Area (TPSA): 52.90 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.42
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 509-60-4
• Paramorphan
• C3S5FRP6JW
• DTXSID7048908
• IDS-ND-009
• DTXCID4028834
• NSC-117865
• Morphinan-3,6-diol, 4,5-epoxy-17-methyl-, (5alpha,6alpha)-
• (4R,4aR,7S,7aR,12bS)-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7,9-diol
• (4R,4aR,7S,7aR,12bS)-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
• RefChem:133883
• (1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7(18),8,10-triene-10,14-diol
• 208-100-8
• Paramorfan
• Morphine, dihydro-
• 6-alpha-Hydromorphol
• Dihydromorfin
• CHEBI:4575
• 7,8-DIHYDROMORPHINE
• NSC 117865
• Dihydromorfin [Czech]
• Dihydromorphine (1mg/ml in Methanol)
• 6.alpha.-Hydromorphol
• 7,8-Dihydromorphin
• EINECS 208-100-8
• UNII-C3S5FRP6JW
• dihydromorphin
• 7,8-Dihydromorphin [IUPAC]
• DEA No. 9145
• NCGC00247721-01
• 7,8 dihydromorphine
• Morphinan-3,6alpha-diol, 4,5alpha-epoxy-17-methyl-
• O-Desmethyldihydrocodeine
• CHEMBL1500
• DIHYDROMORPHINE [MI]
• SCHEMBL26346
• (5.alpha.,6.alpha.)-4,5-Epoxy-17-methylmorphinan-3,6-diol
• GTPL1616
• DIHYDROMORPHINE [WHO-DD]
• Morphinan-3,6-alpha-diol, 4,5-alpha-epoxy-17-methyl-
• SCHEMBL29394226
• HYDROMORPHOL, 6.ALPHA.-
• Tox21_112886
• BDBM50452273
• DIHYDROMORPHINE [USP IMPURITY]
• DB01565
• Dihydromorphine 0.1 mg/ml in Methanol
• Dihydromorphine 1.0 mg/ml in Methanol
• CAS-509-60-4
• NS00001103
• Q4161314
• HYDROMORPHONE HYDROCHLORIDE IMPURITY D [EP IMPURITY]
• 3,6-DIHYDROXY-(5.ALPHA.,6.ALPHA.)-4,5-EPOXY-17-METHYLMORPHINAN
• HYDROMORPHONE HYDROCHLORIDE IMPURITY, DIHYDROMORPHINE (DHM)- [USP IMPURITY]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9893	98.93%
Caco-2	+	0.8731	87.31%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Lysosomes	0.5493	54.93%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.9290	92.90%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9393	93.93%
P-glycoprotein inhibitior	-	0.9524	95.24%
P-glycoprotein substrate	+	0.8779	87.79%
CYP3A4 substrate	+	0.7522	75.22%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	+	0.7078	70.78%
CYP3A4 inhibition	-	0.8793	87.93%
CYP2C9 inhibition	-	0.9309	93.09%
CYP2C19 inhibition	-	0.7678	76.78%
CYP2D6 inhibition	-	0.6170	61.70%
CYP1A2 inhibition	-	0.7970	79.70%
CYP2C8 inhibition	-	0.9446	94.46%
CYP inhibitory promiscuity	-	0.9646	96.46%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6283	62.83%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9821	98.21%
Skin irritation	-	0.7815	78.15%
Skin corrosion	-	0.9273	92.73%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6104	61.04%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8172	81.72%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.7895	78.95%
Acute Oral Toxicity (c)	II	0.7053	70.53%
Estrogen receptor binding	-	0.7196	71.96%
Androgen receptor binding	-	0.6783	67.83%
Thyroid receptor binding	+	0.5713	57.13%
Glucocorticoid receptor binding	+	0.5647	56.47%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.5907	59.07%
Honey bee toxicity	-	0.8876	88.76%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	-	0.4624	46.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.90%	96.09%
CHEMBL233	P35372	Mu opioid receptor	97.03%	97.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.86%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.46%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.90%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.83%	93.40%
CHEMBL238	Q01959	Dopamine transporter	89.52%	95.88%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.42%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.29%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.93%	100.00%
CHEMBL236	P41143	Delta opioid receptor	85.71%	99.35%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.32%	91.03%
CHEMBL217	P14416	Dopamine D2 receptor	84.87%	95.62%
CHEMBL234	P35462	Dopamine D3 receptor	83.99%	90.48%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.12%	94.45%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.44%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.24%	90.71%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.38%	96.38%

Plants that contains it

• Crinum asiaticum
• Papaver somniferum

Cross-Links

• PubChem: 5359421
• NPASS: NPC97086
• LOTUS: LTS0022470
• wikiData: Q105286619