Physostigmine

Details

• Internal ID: 14215948-a3b3-46e0-98be-c84be6c3ff43
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyrroloindoles
• IUPAC Name: [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
• SMILES (Canonical): CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
• SMILES (Isomeric): C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
• InChI: InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1
• InChI Key: PIJVFDBKTWXHHD-HIFRSBDPSA-N
• Popularity: 15,347 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁N₃O₂
• Molecular Weight: 275.35 g/mol
• Exact Mass: 275.16337692 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.77
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Eserine
• 57-47-6
• Antilirium
• Physostol
• Esromiotin
• (-)-physostigmine
• Ezerin
• Calabarine
• Erserine
• Fysostigmin
• cogmine
• (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
• Fysostigmin [Czech]
• eserin
• Eserinum
• Eserolein, methylcarbamate (ester)
• Eserine sulfate
• CCRIS 3422
• HSDB 3161
• MCV 4484
• CHEMBL94
• EINECS 200-332-8
• NIH 10421
• NSC 30782
• NSC-30782
• Physostigmine [USP:BAN]
• RCRA waste no. P204
• Physostigmine [USAN:BAN]
• UNII-9U1VM840SP
• CS 58525
• Methyl-carbamic acid, ester with eseroline
• 9U1VM840SP
• Carbamic acid, methyl-, ester with eseroline
• DTXSID3023471
• CHEBI:27953
• C15H21N3O2
• MCV-4484
• NSC30782
• Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-
• NCGC00093889-03
• ESERINE HEMISULFATE
• [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
• 1,2,3,3abeta,8abeta-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)-indol-5-yl methylcarbamate
• (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-ol methylcarbamate (ester)
• Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)
• DTXCID603471
• CHEMBL537674
• (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate
• CAS-57-47-6
• Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS,8aR)-
• Eserolein, methylcarbamate
• physostigmin
• Xalieve
• (-) physostigmine
• Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS,8aR)-
• Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-
• Eserine (TN)
• Physostigmine (USP)
• Spectrum_000916
• Spectrum_001789
• ESERINUM [HPUS]
• SpecPlus_000381
• Prestwick0_000566
• Prestwick1_000566
• Prestwick2_000566
• Prestwick3_000566
• Spectrum2_000330
• Spectrum2_000757
• Spectrum2_001283
• Spectrum3_000545
• Spectrum3_000901
• Spectrum4_000997
• Spectrum4_001631
• Spectrum4_001913
• Spectrum5_000441
• Spectrum5_000626
• Spectrum5_001672
• PHYSOSTIGMINE [MI]
• D09JVV
• physostigmine.salicylic acid
• PHYSOSTIGMINE [HSDB]
• Lopac0_000483
• SCHEMBL24044
• BSPBio_000352
• BSPBio_002189
• KBioGR_001433
• KBioGR_002061
• KBioGR_002533
• KBioSS_001396
• KBioSS_002279
• PHYSOSTIGMINE [VANDF]
• MLS001304022
• DivK1c_006477
• PHYSOSTIGMINE [MART.]
• SPECTRUM1500753
• SPBio_000339
• SPBio_000774
• SPBio_001285
• SPBio_002571
• PHYSOSTIGMINE [WHO-DD]
• BPBio1_000388
• cid_657348
• GTPL6598
• MEGxp0_001872
• ACon1_000097
• BDBM11023
• KBio1_001421
• KBio2_001396
• KBio2_002278
• KBio2_003964
• KBio2_004846
• KBio2_006532
• KBio2_007414
• KBio3_001689
• KBio3_001842
• Eserine, >=98.0% (N)
• PIJVFDBKTWXHHD-HIFRSBDPSA-N
• HMS1921G06
• HMS2089M11
• HMS2236L08
• HMS3261B07
• BCP19735
• Carbamic acid, ester with eseroline
• HY-N6608
• PHYSOSTIGMINE [USP IMPURITY]
• Tox21_111228
• Tox21_301591
• Tox21_500483
• BDBM50004000
• BDBM50222010
• CCG-38605
• AKOS016843649
• Tox21_111228_1
• CS-O-11713
• DB00981
• LP00483
• SDCCGMLS-0066585.P001
• SDCCGSBI-0050467.P005
• NCGC00093889-01
• NCGC00093889-02
• NCGC00093889-04
• NCGC00093889-05
• NCGC00093889-06
• NCGC00093889-07
• NCGC00093889-08
• NCGC00093889-09
• NCGC00093889-10
• NCGC00093889-12
• NCGC00093889-13
• NCGC00093889-20
• NCGC00255345-01
• NCGC00261168-01
• AC-15983
• SMR000718753
• SBI-0050467.P004
• LS-109562
• Physostigmine (buccal, xerostomia), Calabar
• CS-0034353
• EU-0100483
• P0406
• Physostigmine (local acting gel, xerostomia)
• Physostigmine 100 microg/mL in Acetonitrile
• C06535
• D00196
• E 8375
• EN300-23839407
• Q410595
• Acetylcholinesterase inhibitor (dry mouth), Calabar
• Eserine; Antilirium; Physostol; Esromiotin; Ezerin
• SR-01000075341-1
• WLN: T B556 EN GNTT&J B1 E1 G1 KOVM1
• BRD-K25650355-001-02-5
• BRD-K25650355-059-02-3
• BRD-K25650355-059-12-2
• Physostigmine (local acting gel, xerostomia), Calabar
• (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate hydrochloride
• (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate; 2-hydroxybenzoic acid
• (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol methylcarba-mate (ester)
• 1,2,3,3A.BETA.,8A.BETA.-HEXAHYDRO-1,3A,8-TRIMETHYLPYRROLO(2,3-B)-INDOL-5-YL METHYLCARBAMATE
• Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-methylcarbamate), (3aS,8aR)-
• Pyrrolo[2, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9912	99.12%
Caco-2	+	0.8435	84.35%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Lysosomes	0.8171	81.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9456	94.56%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8667	86.67%
P-glycoprotein inhibitior	-	0.8409	84.09%
P-glycoprotein substrate	-	0.6151	61.51%
CYP3A4 substrate	+	0.6762	67.62%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	-	0.7349	73.49%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8472	84.72%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6425	64.25%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9949	99.49%
Skin irritation	-	0.7734	77.34%
Skin corrosion	-	0.9088	90.88%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5203	52.03%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8675	86.75%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6795	67.95%
Acute Oral Toxicity (c)	I	0.7777	77.77%
Estrogen receptor binding	+	0.6383	63.83%
Androgen receptor binding	+	0.7067	70.67%
Thyroid receptor binding	+	0.6728	67.28%
Glucocorticoid receptor binding	+	0.5928	59.28%
Aromatase binding	+	0.8227	82.27%
PPAR gamma	+	0.6223	62.23%
Honey bee toxicity	+	0.7405	74.05%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.7300	73.00%
Fish aquatic toxicity	+	0.8263	82.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	28 nM; 47 nM; 17.78 nM; 14.1 nM; 28 nM; 61 nM; 17.78 nM; 30 nM; 13.49 nM; 40 nM; 43 nM; 80 nM; 30 nM; 28 nM; 32 nM; 40 nM; 2.9 nM; 27.9 nM; 56.7 nM; 19 nM; 31 nM; 35 nM; 19 nM; 0.43 nM; 18.9 nM; 18.97 nM; 57 nM; 27.9 nM; 43 nM; 57.02 nM; 27.9 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 15715468; PMID: 9871563; PMID: 11141093; PMID: 11689067; PMID: 11708910; DOI: 10.1016/S0960-894X(00)80545-4; PMID: 12620072; DOI: 10.1016/0960-894X(95)00371-Y; PMID: 15588084; DOI: 10.1007/s00044-013-0847-2; PMID: 1507203; PMID: 27236720; PMID: 15878275; PMID: 16570913; PMID: 26886849; PMID: 26189031; PMID: 23746477; PMID: 20627738; PMID: 20684567; PMID: 8064800; PMID: 2202827; PMID: 2202827; PMID: 7636841; PMID: 1738151; PMID: 7707311; PMID: 8558505; PMID: 8978837; PMID: 9288171; PMID: 1552502; PMID: 9435905; PMID: 9632370
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	281.8 nM; 281.8 nM; 281.8 nM	Potency; Potency; Potency	via CMAUP; via Super-PRED; via CMAUP
CHEMBL1914	P06276	Butyrylcholinesterase	35 nM; 19 nM; 35 nM; 129 nM; 15 nM; 73 nM; 73 nM; 16 nM; 16 nM; 23.1 nM; 16 nM; 22.91 nM; 26.3 nM; 16 nM; 16 nM; 16 nM; 28 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 1507203; PMID: 20067290; PMID: 1552502; PMID: 2202827; PMID: 2202827; PMID: 7636841; PMID: 7707311; PMID: 9288171; PMID: 9632370; PMID: 11689067; PMID: 11708910; PMID: 12620072; PMID: 15588084; PMID: 15715468; PMID: 16570913; PMID: 20627738; PMID: 18817366
CHEMBL289	P10635	Cytochrome P450 2D6	200 nM	IC50	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	4 nM; 4 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	28183.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.74%	96.09%
CHEMBL1914	P06276	Butyrylcholinesterase	96.51%	95.00%
CHEMBL220	P22303	Acetylcholinesterase	96.19%	94.45%
CHEMBL4208	P20618	Proteasome component C5	94.79%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.72%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	92.62%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.48%	95.56%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	89.20%	91.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.92%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.29%	90.71%
CHEMBL2243	O00519	Anandamide amidohydrolase	84.30%	97.53%
CHEMBL5028	O14672	ADAM10	83.65%	97.50%
CHEMBL233	P35372	Mu opioid receptor	83.20%	97.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.16%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.41%	82.69%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.10%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.00%	91.11%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.24%	91.24%
CHEMBL2535	P11166	Glucose transporter	80.00%	98.75%

Plants that contains it

• Physostigma venenosum

Cross-Links

• PubChem: 5983
• NPASS: NPC230942
• ChEMBL: CHEMBL94
• LOTUS: LTS0149705
• wikiData: Q410595