Chimonanthine

Details

• Internal ID: 2604e93a-4a92-40d8-8579-2638666469d6
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyrroloindoles
• IUPAC Name: (3aS,8bS)-8b-[(3aS,8bS)-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-8b-yl]-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole
• SMILES (Canonical): CN1CCC2(C1NC3=CC=CC=C32)C45CCN(C4NC6=CC=CC=C56)C
• SMILES (Isomeric): CN1CC[C@@]2([C@H]1NC3=CC=CC=C32)[C@@]45CCN([C@@H]4NC6=CC=CC=C56)C
• InChI: InChI=1S/C22H26N4/c1-25-13-11-21(15-7-3-5-9-17(15)23-19(21)25)22-12-14-26(2)20(22)24-18-10-6-4-8-16(18)22/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20-,21+,22+/m0/s1
• InChI Key: HOYXPMHLHJOGHD-FNAHDJPLSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆N₄
• Molecular Weight: 346.50 g/mol
• Exact Mass: 346.21574685 g/mol
• Topological Polar Surface Area (TPSA): 30.50 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.04
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• Chimonanthin
• 5545-89-1
• 1-Demethylcalycanthidine
• (-)-Chimonanthine
• Calycanthidine, 1-demethyl-
• UNII-97C4UE479O
• 97C4UE479O
• L-Chimonanthine
• (3aS,3a'S,8aS,8a'S)-1,1'-dimethyl-2,2',3,3',8,8',8a,8a'-octahydro-1H,1'H-3a,3a'-bipyrrolo[2,3-b]indole
• CHIMONANTHINE [MI]
• CHEBI:87
• (3aS,8bS)-8b-[(3aS,8bS)-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-8b-yl]-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole
• DTXSID50204016
• HY-N5118
• AKOS040760324
• CS-0032434
• C09133
• Q27105228
• 3A,3'A(1H,1'H)-BIPYRROLO(2,3-B)INDOLE, 2,2',3,3',8,8',8A,8'A-OCTAHYDRO-1,1'-DIMETHYL-, (3AS,3'AS,8AS,8'AS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9861	98.61%
Caco-2	+	0.7789	77.89%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Lysosomes	0.4955	49.55%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.9452	94.52%
OATP1B3 inhibitior	+	0.9433	94.33%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.5718	57.18%
P-glycoprotein inhibitior	-	0.7474	74.74%
P-glycoprotein substrate	-	0.5519	55.19%
CYP3A4 substrate	-	0.5080	50.80%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.3953	39.53%
CYP3A4 inhibition	-	0.8781	87.81%
CYP2C9 inhibition	-	0.8910	89.10%
CYP2C19 inhibition	-	0.8007	80.07%
CYP2D6 inhibition	-	0.8950	89.50%
CYP1A2 inhibition	-	0.7576	75.76%
CYP2C8 inhibition	-	0.9758	97.58%
CYP inhibitory promiscuity	-	0.7577	75.77%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6855	68.55%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9980	99.80%
Skin irritation	-	0.7484	74.84%
Skin corrosion	-	0.8781	87.81%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9272	92.72%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.5270	52.70%
skin sensitisation	-	0.8670	86.70%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5160	51.60%
Acute Oral Toxicity (c)	II	0.4868	48.68%
Estrogen receptor binding	+	0.6321	63.21%
Androgen receptor binding	+	0.7633	76.33%
Thyroid receptor binding	+	0.6529	65.29%
Glucocorticoid receptor binding	-	0.7200	72.00%
Aromatase binding	+	0.6114	61.14%
PPAR gamma	+	0.6366	63.66%
Honey bee toxicity	-	0.9673	96.73%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9772	97.72%

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	97.10%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.17%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.46%	95.56%
CHEMBL4208	P20618	Proteasome component C5	87.92%	90.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.63%	94.62%
CHEMBL238	Q01959	Dopamine transporter	86.39%	95.88%
CHEMBL5805	Q9NR97	Toll-like receptor 8	85.40%	96.25%
CHEMBL1937	Q92769	Histone deacetylase 2	85.24%	94.75%
CHEMBL3524	P56524	Histone deacetylase 4	82.18%	92.97%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.91%	96.39%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.47%	93.40%
CHEMBL5028	O14672	ADAM10	81.32%	97.50%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	81.18%	90.71%

Plants that contains it

• Chimonanthus praecox
• Pyrola calliantha
• Pyrola japonica

Cross-Links

• PubChem: 3083909
• NPASS: NPC60262
• LOTUS: LTS0047745
• wikiData: Q27105228