(-)-Adlumine

Details

• Internal ID: 9b5be7ac-3cd0-4593-800b-1f58f405fbb5
• Taxonomy: Alkaloids and derivatives > Phthalide isoquinolines
• IUPAC Name: (6R)-6-[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
• SMILES (Canonical): CN1CCC2=CC(=C(C=C2C1C3C4=C(C5=C(C=C4)OCO5)C(=O)O3)OC)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C=C2[C@@H]1[C@H]3C4=C(C5=C(C=C4)OCO5)C(=O)O3)OC)OC
• InChI: InChI=1S/C21H21NO6/c1-22-7-6-11-8-15(24-2)16(25-3)9-13(11)18(22)19-12-4-5-14-20(27-10-26-14)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19-/m1/s1
• InChI Key: SZDGAZFTAUFFQH-RTBURBONSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₁NO₆
• Molecular Weight: 383.40 g/mol
• Exact Mass: 383.13688739 g/mol
• Topological Polar Surface Area (TPSA): 66.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• L-Adlumine
• O-Methylseverzine
• Adlumine, (-)-
• 21414-43-7
• Adlumine L-form [MI]
• 38W4159DNQ
• Corlumine
• UNII-38W4159DNQ
• FURO(3,4-E)-1,3-benzodioxol-8(6H)-one, 6-((1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)-, (6R)-
• (+)-Carlumine
• NSC 32983
• (?)-Adlumine
• Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)-, (R-(R*,S*))-
• AKOS040749857
• (6R)-6-[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
• Q27256823

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9365	93.65%
Caco-2	+	0.8810	88.10%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Lysosomes	0.4432	44.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9230	92.30%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8458	84.58%
P-glycoprotein inhibitior	+	0.8811	88.11%
P-glycoprotein substrate	-	0.7267	72.67%
CYP3A4 substrate	+	0.6622	66.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3512	35.12%
CYP3A4 inhibition	+	0.8035	80.35%
CYP2C9 inhibition	+	0.8950	89.50%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9007	90.07%
CYP2C8 inhibition	-	0.8471	84.71%
CYP inhibitory promiscuity	+	0.5827	58.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5569	55.69%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9647	96.47%
Skin irritation	-	0.7997	79.97%
Skin corrosion	-	0.9428	94.28%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6476	64.76%
Micronuclear	+	0.5274	52.74%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8694	86.94%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6128	61.28%
Acute Oral Toxicity (c)	III	0.7536	75.36%
Estrogen receptor binding	+	0.7841	78.41%
Androgen receptor binding	-	0.6502	65.02%
Thyroid receptor binding	-	0.6157	61.57%
Glucocorticoid receptor binding	+	0.9109	91.09%
Aromatase binding	-	0.7030	70.30%
PPAR gamma	+	0.7126	71.26%
Honey bee toxicity	-	0.7758	77.58%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.8141	81.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.93%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.78%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.73%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.60%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.80%	85.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.23%	93.99%
CHEMBL2581	P07339	Cathepsin D	93.72%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.65%	86.33%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	92.46%	82.67%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	90.86%	96.86%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.68%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.64%	92.62%
CHEMBL2056	P21728	Dopamine D1 receptor	88.60%	91.00%
CHEMBL2535	P11166	Glucose transporter	88.58%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.29%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.17%	94.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	86.52%	90.95%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	85.22%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.03%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.35%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.72%	82.38%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.94%	97.14%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.35%	92.38%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.80%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.01%	89.62%

Plants that contains it

• Angelica dahurica
• Artabotrys maingayi
• Capnoides sempervirens
• Corydalis gortschakovii
• Corydalis ophiocarpa
• Corydalis pseudoadunca
• Corydalis scouleri
• Corydalis ternata
• Corydalis vaginans
• Diospyros ebenum
• Fumaria parviflora
• Fumaria vaillantii
• Lappula squarrosa
• Ligularia sagitta
• Mezzettia parviflora
• Piper methysticum
• Psacalium peltatum
• Senna spectabilis
• Stachys plumosa
• Symphytum officinale
• Thuja plicata
• Ulex parviflorus subsp. airensis
• Vepris heterophylla

Cross-Links

• PubChem: 638255
• NPASS: NPC282420
• LOTUS: LTS0076629
• wikiData: Q27256823