Isoboldine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	011372f0-3387-4790-86af-0ab030a79adf
Taxonomy	Alkaloids and derivatives > Aporphines
IUPAC Name	(6aS)-2,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,9-diol
SMILES (Canonical)	CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)O)O)OC
SMILES (Isomeric)	CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)O)O)OC
InChI	InChI=1S/C19H21NO4/c1-20-5-4-10-8-16(24-3)19(22)18-12-9-15(23-2)14(21)7-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1
InChI Key	LINHZVMHXABQLB-ZDUSSCGKSA-N
Popularity	139 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₉H₂₁NO₄
Molecular Weight	327.40 g/mol
Exact Mass	327.14705815 g/mol
Topological Polar Surface Area (TPSA)	62.20 Å²
XlogP	2.20
Atomic LogP (AlogP)	2.87
H-Bond Acceptor	5
H-Bond Donor	2
Rotatable Bonds	2

Synonyms

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(+)-Isoboldine

d-Isoboldine

Isoteolin

(S)-Isoboldine

(S)-(+)-Isoboldine

UNII-M002E511AJ

Isoteoline

Izoteolin

M002E511AJ

NSC 113983

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8085	80.85%
Caco-2	+	0.7694	76.94%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5804	58.04%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.9039	90.39%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.6012	60.12%
P-glycoprotein inhibitior	-	0.9056	90.56%
P-glycoprotein substrate	-	0.6708	67.08%
CYP3A4 substrate	+	0.6059	60.59%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.8593	85.93%
CYP2C9 inhibition	-	0.9081	90.81%
CYP2C19 inhibition	-	0.8384	83.84%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	+	0.9378	93.78%
CYP2C8 inhibition	-	0.7457	74.57%
CYP inhibitory promiscuity	-	0.9213	92.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7029	70.29%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9307	93.07%
Skin irritation	-	0.7540	75.40%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3855	38.55%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.8074	80.74%
skin sensitisation	-	0.8960	89.60%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.9076	90.76%
Acute Oral Toxicity (c)	III	0.7111	71.11%
Estrogen receptor binding	+	0.6671	66.71%
Androgen receptor binding	-	0.5636	56.36%
Thyroid receptor binding	+	0.6431	64.31%
Glucocorticoid receptor binding	+	0.8184	81.84%
Aromatase binding	+	0.5403	54.03%
PPAR gamma	+	0.7281	72.81%
Honey bee toxicity	-	0.8924	89.24%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.8948	89.48%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	35481.3 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	25118.9 nM	Potency	via CMAUP
CHEMBL4801	P29466	Caspase-1	31622.8 nM 31622.8 nM 31622.8 nM	Potency Potency Potency	via CMAUP via CMAUP via CMAUP
CHEMBL3468	P55210	Caspase-7	31622.8 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM	Potency	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	12589.3 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	25118.9 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	6309.6 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	19952.6 nM 19952.6 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM 31622.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	11220.2 nM 14125.4 nM	Potency Potency	via CMAUP via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.20%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	97.53%	95.62%
CHEMBL2056	P21728	Dopamine D1 receptor	95.61%	91.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.98%	91.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.18%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.15%	91.49%
CHEMBL2581	P07339	Cathepsin D	93.83%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.35%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.81%	92.94%
CHEMBL3438	Q05513	Protein kinase C zeta	90.14%	88.48%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.13%	85.14%
CHEMBL4208	P20618	Proteasome component C5	90.04%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.77%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	88.76%	91.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.97%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.74%	93.40%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.67%	89.62%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	85.60%	95.34%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.44%	94.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.09%	96.86%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.04%	93.03%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	83.49%	95.70%
CHEMBL5747	Q92793	CREB-binding protein	82.74%	95.12%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.21%	90.71%
CHEMBL2535	P11166	Glucose transporter	81.00%	98.75%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.72%	82.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.55%	89.00%
CHEMBL3474	P14555	Phospholipase A2 group IIA	80.55%	94.05%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Aconitum karakolicum

Aconitum paniculigerum var. wulingense

Balanophora polyandra