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Yohimbine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical 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 |
| Formula | C21H26N2O3 |
| HBA | 4 |
| HBD | 2 |
| MW | 354.45 |
| Rotatable Bonds | 1 |
| TPSA | 65.56 |
| LogP | 2.65 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.57 |
| Exact Mass | 354.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rauvolfia caffra | Apocynaceae | Plantae | 947877 |
Showing of synonyms
Yohimbine
146-48-5
Yohimbin
Quebrachin
Corynine
Quebrachine
APHRODINE
Aphrosol
(+)-Yohimbine
Actibine
Johimbin
Yohimbinum
EINECS 205-672-0
UNII-2Y49VWD90Q
BRN 0097276
2Y49VWD90Q
CCRIS 9415
DTXSID9040130
CHEBI:10093
Methyl 17alpha-hydroxyyohimban-16alpha-carboxylate
DTXCID7020130
4-25-00-01237 (Beilstein Handbook Reference)
205-672-0
Yohimbic acid methyl ester
Yohimbe bark
Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-
17-Hydroxyyohimban-16-carboxylic acid methyl ester
CHEMBL15245
17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester
(16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester
Methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
CHEMBL537669
Yohimbine (DCF)
CAS-146-48-5
Methyl hydroxy[?]carboxylate
Trans-Quinolizidine yohimbine
SR-01000075297
Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.
MFCD00005093
NSC19509
YOHIMBINE [MI]
Prestwick0_000584
Prestwick1_000584
Prestwick2_000584
Prestwick3_000584
Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester
YOHIMBINE [VANDF]
YOHIMBINUM [HPUS]
Cid_6169
Cid_8969
YOHIMBE HYDROCHLORIDE
YOHIMBINE [WHO-DD]
Lopac0_001210
SCHEMBL33954
BSPBio_000428
BSPBio_001236
GTPL102
KBioGR_000576
KBioSS_000576
MLS000728591
SPBio_002647
BPBio1_000472
Yohimbol-16alpha-carboxylic acid, methyl ester (6CI)
BCBcMAP01_000032
KBio2_000576
KBio2_003144
KBio2_005712
KBio3_001031
KBio3_001032
Bio1_000455
Bio1_000944
Bio1_001433
Bio2_000458
Bio2_000938
HMS1362N17
HMS1792N17
HMS1990N17
HMS2089G19
HMS2234C18
Tox21_110019
BDBM50013515
BDBM50203564
AKOS015902024
Tox21_110019_1
Yohimban-16-.alpha.-carboxylic acid, 17-.alpha.-hydroxy-, methyl ester
Yohimban-16alpha-carboxylic acid, 17alpha-hydroxy-, methyl ester (8CI)
CCG-205284
CS-5173
DB01392
FY01219
GS-5751
SDCCGSBI-0051177.P002
IDI1_002213
MRF-0000020
SMP1_000320
NCGC00013260-01
NCGC00025018-05
NCGC00025018-06
NCGC00025018-07
NCGC00025018-10
NCGC00025018-11
NCGC00025018-16
NCGC00025018-17
NCGC00025018-24
NCGC00025018-29
HY-12715
SMR000470778
17a-hydroxy-16a-methoxycarbonyl-yohimbane
NS00003970
C09256
D08685
H10057
EN300-19731915
Q412226
SR-01000075297-5
BRD-K35586044-001-02-6
BRD-K35586044-003-03-0
BRD-K35586044-003-11-3
BRD-K35586044-003-14-7
BRD-K35586044-003-15-4
Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16|A,17|A)-
17.ALPHA.-HYDROXY-20-.ALPHA.-YOHIMBAN-16-.BETA.-CARBOXYLIC ACID, METHYL ESTER
Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)- (9CI)
(1R,2S,4aR,13bS,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2'',3'':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester hydrochloride
103834-06-6
Methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
Pubchem:
8969
Cas:
146-48-5
Gnps:
CCMSLIB00005768187
Zinc:
ZINC000003860825
Kegg Ligand:
C09256
Chebi:
10093
Nmrshiftdb2:
60026147
Metabolights:
MTBLC10093
Chembl:
CHEMBL15245
Comptox:
DTXSID9040130
Drugbank:
DB01392
Bindingdb:
50013515
CPRiL:
693
SMILES: c1cccc2[nH]c(c3c12)C4N(CC3)CC5C(C4)CCCC5
Level: 0
Mol. Weight: 354.45 g/mol
Antimicrobial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -5.07
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.000
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.5
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.850
- Plasma Protein Binding
- 58.33
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.630
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.540
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.390
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.200
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -11.350
- Rat (Acute)
- 3.090
- Rat (Chronic Oral)
- 1.890
- Fathead Minnow
- 4.070
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 434.730
- Hydration Free Energy
- -7.580
- Log(D) at pH=7.4
- 2.550
- Log(P)
- 2.73
- Log S
- -2.9
- Log(Vapor Pressure)
- -8.98
- Melting Point
- 220.31
- pKa Acid
- 10.62
- pKa Basic
- 6.72
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8686 |
| clade A/E 93TH057 HIV-1 gp120 core | A0A0M3KKW9 | A0A0M3KKW9_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.8370 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.8275 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.8116 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7930 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.7877 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7730 |
| 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase | O33877 | FABA_PSEAE | Pseudomonas aeruginosa | 3 | 0.7609 |
| Non-receptor tyrosine-protein kinase TYK2 | P29597 | TYK2_HUMAN | Homo sapiens | 3 | 0.7562 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7499 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.7461 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 2 | 0.7410 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7307 |
| Non-receptor tyrosine-protein kinase TYK2 | P29597 | TYK2_HUMAN | Homo sapiens | 3 | 0.7279 |
| Nitroreductase domain-containing protein | Q8DW21 | Q8DW21_STRMU | Streptococcus mutans serotype c | 3 | 0.7275 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7233 |
| Ribosome-inactivating protein alpha-trichosanthin | P09989 | RIPT_TRIKI | Trichosanthes kirilowii | 3 | 0.7158 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 2 | 0.7155 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7084 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7062 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7009 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7009 |
| 4-chlorobenzoyl CoA ligase | Q8GN86 | Q8GN86_9BURK | Alcaligenes sp. AL3007 | 2 | 0.7005 |