IMPPAT | IMPPAT: Indian Medicinal Plants, Phytochemistry And Therapeutics

Summary

SMILES: COC(=O)[C@H]1[C@@H](O)CC[C@@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1
InChI: InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
InChIKey: BLGXFZZNTVWLAY-SCYLSFHTSA-N
DeepSMILES: COC=O)[C@H][C@@H]O)CC[C@@H][C@@H]6C[C@@H]NC6)CCcc6[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2CCCCC2CN1CC3
Scaffold Graph/Node level: C1CCC2CN3CCC4C5CCCCC5NC4C3CC2C1
Scaffold Graph level: C1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1
Functional groups: COC(C)=O; CO; CN(C)C; c[nH]c

Chemical classification

ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Yohimbine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Yohimbine-like alkaloids

Synonymous chemical names:
yohimbine, yohimibine, yihimbine, Yohimbine

External chemical identifiers:
CID:CID_8969 ; ChEMBL:CHEMBL15245 ; ChEBI:CHEBI:10093 ; ZINC:ZINC000003860825 ; FDASRS:2Y49VWD90Q ; SureChEMBL:SCHEMBL33954 ; MolPort-001-794-653

Chemical structure download

2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT

Physicochemical properties

Property name	Tool	Property value
Molecular weight (g/mol)	RDKit	354.45
Log P	RDKit	2.65
Topological polar surface area (Å²)	RDKit	65.56
Number of hydrogen bond acceptors	RDKit	4
Number of hydrogen bond donors	RDKit	2
Number of carbon atoms	RDKit	21
Number of heavy atoms	RDKit	26
Number of heteroatoms	RDKit	5
Number of nitrogen atoms	RDKit	2
Number of sulfur atoms	RDKit	0
Number of chiral carbon atoms	RDKit	5
Stereochemical complexity	RDKit	0.24
Number of sp hybridized carbon atoms	RDKit	0
Number of sp² hybridized carbon atoms	RDKit	9
Number of sp³ hybridized carbon atoms	RDKit	12
Shape complexity	RDKit	0.57
Number of rotatable bonds	RDKit	2
Number of aliphatic carbocycles	RDKit	1
Number of aliphatic heterocycles	RDKit	2
Number of aliphatic rings	RDKit	3
Number of aromatic carbocycles	RDKit	1
Number of aromatic heterocycles	RDKit	1
Number of aromatic rings	RDKit	2
Total number of rings	RDKit	5
Number of saturated carbocycles	RDKit	1
Number of saturated heterocycles	RDKit	1
Number of saturated rings	RDKit	2
Number of Smallest Set of Smallest Rings (SSSR)	RDKit	5

Drug-likeness

Property name	Tool	Property value
Number of Lipinski’s rule of 5 violations	RDKit	0
Lipinski’s rule of 5 filter	RDKit	Passed
Number of Ghose filter violations	RDKit	0
Ghose filter	RDKit	Passed
Veber filter	RDKit	Good
Pfizer 3/75 filter	RDKit	Bad
GSK 4/400 filter	RDKit	Good
Weighted quantitative estimate of drug-likeness (QEDw) score	RDKit	0.772957

ADME properties

Property name	Tool	Property value
Bioavailability score	SwissADME	0.55
Solubility class [ESOL]	SwissADME	Moderately soluble
Solubility class [Silicos-IT]	SwissADME	Soluble
Blood Brain Barrier permeation	SwissADME	Yes
Gastrointestinal absorption	SwissADME	High
Log K_p (Skin permeation, cm/s)	SwissADME	-6.37
Number of PAINS structural alerts	SwissADME	1
Number of Brenk structural alerts	SwissADME	0
CYP1A2 inhibitor	SwissADME	No
CYP2C19 inhibitor	SwissADME	No
CYP2C9 inhibitor	SwissADME	No
CYP2D6 inhibitor	SwissADME	Yes
CYP3A4 inhibitor	SwissADME	No
P-glycoprotein substrate	SwissADME	Yes

Human target proteins supported by experimental evidence

IMPPAT target identifier	Gene identifier	HGNC symbol	Entrez Gene identifier	Source
TAR_EXP_000177	ENSG00000183813	CCR4	1233	ChEMBL
TAR_EXP_000178	ENSG00000160791	CCR5	1234	ChEMBL
TAR_EXP_000187	ENSG00000118432	CNR1	1268	ChEMBL, NPASS
TAR_EXP_000200	ENSG00000163485	ADORA1	134	ChEMBL
TAR_EXP_000133	ENSG00000133019	CHRM3	1131	ChEMBL
TAR_EXP_000134	ENSG00000180720	CHRM4	1132	ChEMBL, NPASS
TAR_EXP_000137	ENSG00000184984	CHRM5	1133	ChEMBL
TAR_EXP_000144	ENSG00000101204	CHRNA4	1137	ChEMBL
TAR_EXP_000017	ENSG00000169371	SNUPN	10073	NPASS
TAR_EXP_000041	ENSG00000147955	SIGMAR1	10280	ChEMBL
TAR_EXP_000081	ENSG00000173198	CYSLTR1	10800	ChEMBL
TAR_EXP_000095	ENSG00000224143	EHMT2	10919	ChEMBL, NPASS
TAR_EXP_000188	ENSG00000188822	CNR2	1269	ChEMBL, NPASS
TAR_EXP_000125	ENSG00000101180	HRH3	11255	ChEMBL
TAR_EXP_000213	ENSG00000147262	GPR119	139760	ChEMBL, NPASS
TAR_EXP_000174	ENSG00000222028	PSMB11	122706	ChEMBL
TAR_EXP_000175	ENSG00000183625	CCR3	1232	NPASS
TAR_EXP_000212	ENSG00000106113	CRHR2	1395	ChEMBL
TAR_EXP_000211	ENSG00000276191	CRHR1	1394	ChEMBL
TAR_EXP_000203	ENSG00000128271	ADORA2A	135	ChEMBL
TAR_EXP_000130	ENSG00000181072	CHRM2	1129	ChEMBL
TAR_EXP_000127	ENSG00000168539	CHRM1	1128	ChEMBL
TAR_EXP_000179	ENSG00000179934	CCR8	1237	ChEMBL, NPASS
TAR_EXP_001707	ENSG00000121966	CXCR4	7852	ChEMBL, NPASS
TAR_EXP_001056	ENSG00000065989	PDE4A	5141	ChEMBL
TAR_EXP_000761	ENSG00000180871	CXCR2	3579	ChEMBL
TAR_EXP_000760	ENSG00000163464	CXCR1	3577	ChEMBL
TAR_EXP_000739	ENSG00000148680	HTR7	3363	BindingDB
TAR_EXP_000738	ENSG00000158748	HTR6	3362	ChEMBL, NPASS
TAR_EXP_000735	ENSG00000166736	HTR3A	3359	ChEMBL
TAR_EXP_000734	ENSG00000147246	HTR2C	3358	BindingDB, ChEMBL, NPASS
TAR_EXP_000233	ENSG00000171873	ADRA1D	146	BindingDB, ChEMBL, NPASS
TAR_EXP_000236	ENSG00000170214	ADRA1B	147	ChEMBL, NPASS
TAR_EXP_000239	ENSG00000120907	ADRA1A	148	BindingDB, ChEMBL, NPASS
TAR_EXP_000243	ENSG00000150594	ADRA2A	150	ChEMBL, NPASS
TAR_EXP_000249	ENSG00000274286	ADRA2B	151	ChEMBL, NPASS
TAR_EXP_000250	ENSG00000100448	CTSG	1511	ChEMBL
TAR_EXP_000255	ENSG00000184160	ADRA2C	152	ChEMBL, NPASS
TAR_EXP_000257	ENSG00000168329	CX3CR1	1524	ChEMBL, NPASS
TAR_EXP_000733	ENSG00000135914	HTR2B	3357	BindingDB, ChEMBL, NPASS
TAR_EXP_000732	ENSG00000102468	HTR2A	3356	ChEMBL
TAR_EXP_000731	ENSG00000179097	HTR1F	3355	BindingDB
TAR_EXP_000730	ENSG00000168830	HTR1E	3354	BindingDB
TAR_EXP_000729	ENSG00000179546	HTR1D	3352	BindingDB
TAR_EXP_000773	ENSG00000169083	AR	367	ChEMBL
TAR_EXP_000728	ENSG00000135312	HTR1B	3351	BindingDB, ChEMBL, NPASS
TAR_EXP_000798	ENSG00000055118	KCNH2	3757	ChEMBL
TAR_EXP_000814	ENSG00000108424	KPNB1	3837	NPASS
TAR_EXP_000367	ENSG00000112759	SLC29A1	2030	ChEMBL
TAR_EXP_001053	ENSG00000172572	PDE3A	5139	ChEMBL
TAR_EXP_001005	ENSG00000180914	OXTR	5021	ChEMBL, NPASS
TAR_EXP_001003	ENSG00000112038	OPRM1	4988	ChEMBL
TAR_EXP_001002	ENSG00000082556	OPRK1	4986	ChEMBL
TAR_EXP_001001	ENSG00000116329	OPRD1	4985	ChEMBL
TAR_EXP_000995	ENSG00000101188	NTSR1	4923	ChEMBL
TAR_EXP_000988	ENSG00000185149	NPY2R	4887	ChEMBL
TAR_EXP_000987	ENSG00000164128	NPY1R	4886	ChEMBL
TAR_EXP_000888	ENSG00000100985	MMP9	4318	ChEMBL
TAR_EXP_000883	ENSG00000196611	MMP1	4312	ChEMBL
TAR_EXP_000881	ENSG00000087085	ACHE	43	ChEMBL
TAR_EXP_000863	ENSG00000176136	MC5R	4161	ChEMBL
TAR_EXP_000862	ENSG00000166603	MC4R	4160	ChEMBL
TAR_EXP_000861	ENSG00000124089	MC3R	4159	ChEMBL
TAR_EXP_000851	ENSG00000189221	MAOA	4128	ChEMBL
TAR_EXP_000846	ENSG00000100299	ARSA	410	NPASS
TAR_EXP_000822	ENSG00000182866	LCK	3932	ChEMBL
TAR_EXP_000818	ENSG00000187258	NPSR1	387129	ChEMBL, NPASS
TAR_EXP_000810	ENSG00000128052	KDR	3791	ChEMBL
TAR_EXP_001061	ENSG00000113448	PDE4D	5144	ChEMBL
TAR_EXP_000727	ENSG00000178394	HTR1A	3350	ChEMBL
TAR_EXP_000703	ENSG00000196639	HRH1	3269	ChEMBL, NPASS
TAR_EXP_000261	ENSG00000169252	ADRB2	154	BindingDB, ChEMBL
TAR_EXP_000263	ENSG00000140505	CYP1A2	1544	ChEMBL
TAR_EXP_000265	ENSG00000255974	CYP2A6	1548	ChEMBL
TAR_EXP_000267	ENSG00000188778	ADRB3	155	ChEMBL
TAR_EXP_000271	ENSG00000165841	CYP2C19	1557	ChEMBL
TAR_EXP_000273	ENSG00000138109	CYP2C9	1559	ChEMBL
TAR_EXP_000276	ENSG00000272532	CYP2D6	1565	ChEMBL, NPASS
TAR_EXP_000277	ENSG00000130649	CYP2E1	1571	ChEMBL
TAR_EXP_000280	ENSG00000160868	CYP3A4	1576	ChEMBL
TAR_EXP_000324	ENSG00000184845	DRD1	1812	ChEMBL, NPASS
TAR_EXP_000325	ENSG00000149295	DRD2	1813	BindingDB, ChEMBL, NPASS
TAR_EXP_000326	ENSG00000151577	DRD3	1814	ChEMBL
TAR_EXP_000327	ENSG00000069696	DRD4	1815	ChEMBL
TAR_EXP_000330	ENSG00000144891	AGTR1	185	ChEMBL
TAR_EXP_000332	ENSG00000180772	AGTR2	186	ChEMBL
TAR_EXP_000339	ENSG00000151617	EDNRA	1909	ChEMBL
TAR_EXP_000341	ENSG00000136160	EDNRB	1910	ChEMBL
TAR_EXP_000348	ENSG00000146648	EGFR	1956	ChEMBL
TAR_EXP_000387	ENSG00000141736	ERBB2	2064	ChEMBL
TAR_EXP_000258	ENSG00000043591	ADRB1	153	ChEMBL
TAR_EXP_000704	ENSG00000113749	HRH2	3274	ChEMBL
TAR_EXP_000395	ENSG00000091831	ESR1	2099	ChEMBL
TAR_EXP_000405	ENSG00000180210	F2	2147	ChEMBL
TAR_EXP_000692	ENSG00000113161	HMGCR	3156	ChEMBL
TAR_EXP_000682	ENSG00000137252	HCRTR2	3062	ChEMBL, NPASS
TAR_EXP_000645	ENSG00000113580	NR3C1	2908	ChEMBL
TAR_EXP_000627	ENSG00000102539	MLNR	2862	ChEMBL
TAR_EXP_000620	ENSG00000119973	PRLHR	2834	ChEMBL, NPASS
TAR_EXP_000579	ENSG00000010310	GIPR	2696	ChEMBL
TAR_EXP_000578	ENSG00000121853	GHSR	2693	ChEMBL
TAR_EXP_000572	ENSG00000108773	KAT2A	2648	NPASS
TAR_EXP_000570	ENSG00000288269	GCGR	2642	ChEMBL
TAR_EXP_000554	ENSG00000101347	SAMHD1	25939	ChEMBL
TAR_EXP_000533	ENSG00000113327	GABRG2	2566	ChEMBL
TAR_EXP_000528	ENSG00000145864	GABRB2	2561	ChEMBL
TAR_EXP_000522	ENSG00000151834	GABRA2	2555	ChEMBL
TAR_EXP_000521	ENSG00000022355	GABRA1	2554	ChEMBL
TAR_EXP_000515	ENSG00000010810	FYN	2534	ChEMBL
TAR_EXP_000508	ENSG00000170820	FSHR	2492	ChEMBL, NPASS
TAR_EXP_000505	ENSG00000198793	MTOR	2475	NPASS
TAR_EXP_000487	ENSG00000171051	FPR1	2357	ChEMBL, NPASS
TAR_EXP_000461	ENSG00000102755	FLT1	2321	ChEMBL
TAR_EXP_000397	ENSG00000140009	ESR2	2100	ChEMBL
TAR_EXP_001105	ENSG00000082175	PGR	5241	ChEMBL
TAR_EXP_000357	ENSG00000277571	ELANE	1991	ChEMBL
TAR_EXP_001125	ENSG00000127445	PIN1	5300	NPASS
TAR_EXP_000222	ENSG00000112062	MAPK14	1432	ChEMBL
TAR_EXP_001451	ENSG00000100739	BDKRB1	623	ChEMBL
TAR_EXP_001458	ENSG00000168398	BDKRB2	624	ChEMBL
TAR_EXP_001468	ENSG00000204842	ATXN2	6311	NPASS
TAR_EXP_001470	ENSG00000144285	SCN1A	6323	ChEMBL
TAR_EXP_000214	ENSG00000282608	ADORA3	140	ChEMBL
TAR_EXP_001471	ENSG00000136531	SCN2A	6326	ChEMBL
TAR_EXP_001472	ENSG00000153253	SCN3A	6328	ChEMBL, NPASS
TAR_EXP_001518	ENSG00000103546	SLC6A2	6530	BindingDB, ChEMBL, NPASS
TAR_EXP_001106	ENSG00000085563	ABCB1	5243	ChEMBL, NPASS
TAR_EXP_001520	ENSG00000108576	SLC6A4	6532	BindingDB, ChEMBL
TAR_EXP_001585	ENSG00000075073	TACR2	6865	ChEMBL
TAR_EXP_000223	ENSG00000154611	PSMA8	143471	ChEMBL
TAR_EXP_001587	ENSG00000115353	TACR1	6869	ChEMBL
TAR_EXP_001592	ENSG00000059377	TBXAS1	6916	ChEMBL
TAR_EXP_001618	ENSG00000198900	TOP1	7150	ChEMBL, NPASS
TAR_EXP_001642	ENSG00000121807	CCR2	729230	ChEMBL
TAR_EXP_001669	ENSG00000114812	VIPR1	7433	ChEMBL
TAR_EXP_001684	ENSG00000104267	CA2	760	ChEMBL
TAR_EXP_001727	ENSG00000004948	CALCR	799	ChEMBL
TAR_EXP_001753	ENSG00000137752	CASP1	834	ChEMBL
TAR_EXP_001808	ENSG00000276582	ABCB11	8647	NPASS
TAR_EXP_001811	ENSG00000138735	PDE5A	8654	ChEMBL
TAR_EXP_001837	ENSG00000163394	CCKAR	886	ChEMBL
TAR_EXP_001839	ENSG00000110148	CCKBR	887	ChEMBL
TAR_EXP_001935	ENSG00000164045	CDC25A	993	BindingDB, ChEMBL, NPASS
TAR_EXP_001591	ENSG00000006638	TBXA2R	6915	ChEMBL
TAR_EXP_001366	ENSG00000117152	RGS4	5999	NPASS
TAR_EXP_001519	ENSG00000142319	SLC6A3	6531	ChEMBL
TAR_EXP_001299	ENSG00000073756	PTGS2	5743	ChEMBL
TAR_EXP_001266	ENSG00000008018	PSMB1	5689	ChEMBL
TAR_EXP_001265	ENSG00000101182	PSMA7	5688	ChEMBL
TAR_EXP_001264	ENSG00000100902	PSMA6	5687	ChEMBL
TAR_EXP_001263	ENSG00000143106	PSMA5	5686	ChEMBL
TAR_EXP_001262	ENSG00000041357	PSMA4	5685	ChEMBL
TAR_EXP_001261	ENSG00000100567	PSMA3	5684	ChEMBL
TAR_EXP_001260	ENSG00000106588	PSMA2	5683	ChEMBL
TAR_EXP_001259	ENSG00000129084	PSMA1	5682	ChEMBL
TAR_EXP_001231	ENSG00000102882	MAPK3	5595	ChEMBL
TAR_EXP_001230	ENSG00000100030	MAPK1	5594	ChEMBL
TAR_EXP_001207	ENSG00000154229	PRKCA	5578	ChEMBL
TAR_EXP_001206	ENSG00000042088	TDP1	55775	NPASS
TAR_EXP_001320	ENSG00000262418	PTPRC	5788	ChEMBL
TAR_EXP_001186	ENSG00000138814	PPP3CA	5530	ChEMBL
TAR_EXP_001181	ENSG00000166148	AVPR1A	552	ChEMBL
TAR_EXP_001267	ENSG00000126067	PSMB2	5690	ChEMBL
TAR_EXP_001269	ENSG00000277791	PSMB3	5691	ChEMBL
TAR_EXP_001190	ENSG00000126895	AVPR2	554	ChEMBL, NPASS
TAR_EXP_001273	ENSG00000100804	PSMB5	5693	ChEMBL
TAR_EXP_001270	ENSG00000159377	PSMB4	5692	ChEMBL
TAR_EXP_001298	ENSG00000095303	PTGS1	5742	ChEMBL
TAR_EXP_001294	ENSG00000160013	PTGIR	5739	ChEMBL, NPASS
TAR_EXP_001289	ENSG00000169403	PTAFR	5724	ChEMBL
TAR_EXP_001277	ENSG00000239836	PSMB9	5698	ChEMBL
TAR_EXP_001276	ENSG00000235715	PSMB8	5696	ChEMBL
TAR_EXP_001275	ENSG00000136930	PSMB7	5695	ChEMBL
TAR_EXP_001278	ENSG00000205220	PSMB10	5699	ChEMBL
TAR_EXP_001274	ENSG00000142507	PSMB6	5694	ChEMBL

a curated database

IMPPAT Phytochemical information:
Yohimbine

Summary

Chemical classification

Chemical structure download

Physicochemical properties

Drug-likeness

ADME properties

Human target proteins supported by experimental evidence

IMPPAT Phytochemical information: Yohimbine

Summary

Chemical classification

Chemical structure download

Physicochemical properties

Drug-likeness

ADME properties

Human target proteins supported by experimental evidence

IMPPAT Phytochemical information:
Yohimbine