Structure

Physi-Chem Properties

Molecular Weight:  204.13
Volume:  219.233
LogP:  1.612
LogD:  1.062
LogS:  -1.491
# Rotatable Bonds:  3
TPSA:  39.26
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.802
Synthetic Accessibility Score:  2.125
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.609
MDCK Permeability:  6.349898740154458e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.05
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.785
30% Bioavailability (F30%):  0.061

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.989
Plasma Protein Binding (PPB):  33.734519958496094%
Volume Distribution (VD):  2.126
Pgp-substrate:  68.55976104736328%

ADMET: Metabolism

CYP1A2-inhibitor:  0.145
CYP1A2-substrate:  0.95
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.595
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.866
CYP2D6-inhibitor:  0.656
CYP2D6-substrate:  0.935
CYP3A4-inhibitor:  0.009
CYP3A4-substrate:  0.161

ADMET: Excretion

Clearance (CL):  8.603
Half-life (T1/2):  0.847

ADMET: Toxicity

hERG Blockers:  0.127
Human Hepatotoxicity (H-HT):  0.293
Drug-inuced Liver Injury (DILI):  0.076
AMES Toxicity:  0.028
Rat Oral Acute Toxicity:  0.929
Maximum Recommended Daily Dose:  0.905
Skin Sensitization:  0.923
Carcinogencity:  0.066
Eye Corrosion:  0.046
Eye Irritation:  0.106
Respiratory Toxicity:  0.923

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC171171

Natural Product ID:  NPC171171
Common Name*:   Bufotenine
IUPAC Name:   3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
Synonyms:   Bufotenine
Standard InCHIKey:  VTTONGPRPXSUTJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
SMILES:  CN(C)CCc1c[nH]c2ccc(cc12)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL416526
PubChem CID:   10257
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000183] Tryptamines and derivatives
          • [CHEMONTID:0001637] Serotonins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)99818-1]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota roots n.a. n.a. PMID[10346940]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[11421725]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[15165135]
NPO3983 Piper futokadsura Species Piperaceae Eukaryota n.a. aerial part n.a. PMID[15635246]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15730237]
NPO664 Potentilla multifida Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[17504571]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. PMID[21185919]
NPO11549 Paramuricea clavata Species Paramuriceidae Eukaryota n.a. n.a. n.a. PMID[21939218]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota twigs and leaves Yunnan Province, China 2008-OCT PMID[21954912]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. leaf n.a. PMID[21954912]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. twig n.a. PMID[21954912]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[22708620]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[26722868]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[32223924]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12735 Halimeda macroloba Species Halimedaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2498 Kochia trichophylla Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9398 Cortinarius rubellus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9117 Hammada elegans Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6011 Pleurotus citrinopileatus Species Pleurotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21463 Aruncus dioicus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7884 Centaurea amara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11515 Streptomyces plumbeus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO664 Potentilla multifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2917 Artemisia oranensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12250 Strychnos fendleri Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11549 Paramuricea clavata Species Paramuriceidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26231 Vicia villosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1504 Alicyclobacillus cycloheptanicus Species Alicyclobacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7543 Haplopappus venetus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4797 Gavia immer Species Gaviidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO641 Astragalus globiceps Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3983 Piper futokadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18498 Arundo donax Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12952 Cabucala madagascariensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10043 Phebalium ozothamnoides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5177 Lecanora conizaeoides Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6887 Lytanthus salicinus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT162 Individual Protein Heat shock protein beta-1 Homo sapiens Potency n.a. 53195.3 nM PubChem BioAssay data set
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 53659.6 nM PubChem BioAssay data set
NPT288 Individual Protein Serotonin 1a (5-HT1a) receptor Rattus norvegicus Ki = 259.0 nM PMID[559300]
NPT289 Individual Protein Serotonin 1b (5-HT1b) receptor Rattus norvegicus Ki = 910.0 nM PMID[559300]
NPT292 Individual Protein Serotonin 2c (5-HT2c) receptor Homo sapiens Ki = 70.0 nM PMID[559300]
NPT288 Individual Protein Serotonin 1a (5-HT1a) receptor Rattus norvegicus Ki = 25.12 nM PMID[559302]
NPT290 Individual Protein Serotonin 2a (5-HT2a) receptor Homo sapiens p[A50] = 6.8 n.a. PMID[559304]
NPT4041 Individual Protein Serotonin 7 (5-HT7) receptor Rattus norvegicus Ki = 7.943 nM PMID[559305]
NPT295 Individual Protein Serotonin transporter Homo sapiens IC50 = 1200.0 nM PMID[559306]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 22387.2 nM PMID[559308]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus IC50 = 11400.0 nM PMID[559309]
NPT2 Others Unspecified Potency n.a. 66968.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2117.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19039.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 60207.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 23768.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 23968.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 47824.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 11912.4 nM PubChem BioAssay data set
NPT35 Others n.a. pKa = 9.67 n.a. PMID[559298]
NPT35 Others n.a. pKa = 0.06 n.a. PMID[559298]
NPT35 Others n.a. pKa = 11.2 n.a. PMID[559298]
NPT35 Others n.a. Poct = 0.16 n.a. PMID[559298]
NPT35 Others n.a. LogP = 1.19 n.a. PMID[559298]
NPT27 Others Unspecified Binding energy = 9.4 kCal mol-1 PMID[559299]
NPT1777 Protein Family Serotonin 2 (5-HT2) receptor Rattus norvegicus Ki = 380.0 nM PMID[559300]
NPT805 Protein Complex GABA-A receptor; anion channel Rattus norvegicus Ki > 100000.0 nM PMID[559301]
NPT29 Organism Rattus norvegicus Rattus norvegicus IC50 = 1318.26 nM PMID[559303]
NPT29 Organism Rattus norvegicus Rattus norvegicus Ki = 341.0 nM PMID[559303]
NPT29 Organism Rattus norvegicus Rattus norvegicus IC50 = 12589.25 nM PMID[559303]
NPT29 Organism Rattus norvegicus Rattus norvegicus Ki = 6295.0 nM PMID[559303]
NPT974 Individual Protein Serotonin 1d (5-HT1d) receptor Homo sapiens p[A50] = 7.3 n.a. PMID[559304]
NPT974 Individual Protein Serotonin 1d (5-HT1d) receptor Homo sapiens Intrinsic activity = 0.92 n.a. PMID[559304]
NPT92 Individual Protein Serotonin 1a (5-HT1a) receptor Homo sapiens Kd = 3.162 nM PMID[559307]
NPT1776 Protein Family Serotonin 1 (5-HT1) receptor Rattus norvegicus Kd = 38.9 nM PMID[559310]
NPT35 Others n.a. LogP = 0.06 n.a. PMID[559310]
NPT2 Others Unspecified AC50 n.a. 70794.6 nM PMID[559311]
NPT2 Others Unspecified Ac50 n.a. 70.79 uM PMID[559311]
NPT2 Others Unspecified Ac50 n.a. 79.43 uM PMID[559311]
NPT2 Others Unspecified AC50 n.a. 79432.8 nM PMID[559311]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[559312]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[559312]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC171171 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9879 High Similarity NPC204717
0.9819 High Similarity NPC314002
0.9818 High Similarity NPC220765
0.9576 High Similarity NPC184964
0.9477 High Similarity NPC99666
0.9261 High Similarity NPC156704
0.92 High Similarity NPC307963
0.9195 High Similarity NPC92111
0.9191 High Similarity NPC32771
0.9153 High Similarity NPC77555
0.9138 High Similarity NPC76748
0.9133 High Similarity NPC46580
0.908 High Similarity NPC296527
0.9011 High Similarity NPC475070
0.9 High Similarity NPC45459
0.9 High Similarity NPC315491
0.8989 High Similarity NPC251090
0.8895 High Similarity NPC213308
0.8827 High Similarity NPC326634
0.8795 High Similarity NPC131718
0.8779 High Similarity NPC96890
0.8778 High Similarity NPC222018
0.8728 High Similarity NPC88363
0.8674 High Similarity NPC242209
0.8667 High Similarity NPC106937
0.8632 High Similarity NPC266931
0.861 High Similarity NPC88008
0.858 High Similarity NPC102423
0.8579 High Similarity NPC316981
0.8571 High Similarity NPC5145
0.8534 High Similarity NPC477610
0.8533 High Similarity NPC476167
0.8514 High Similarity NPC72980
0.8508 High Similarity NPC324149
0.8497 Intermediate Similarity NPC476041
0.8497 Intermediate Similarity NPC313791
0.8497 Intermediate Similarity NPC304926
0.8486 Intermediate Similarity NPC249040
0.8486 Intermediate Similarity NPC176538
0.8478 Intermediate Similarity NPC192315
0.8466 Intermediate Similarity NPC171787
0.8444 Intermediate Similarity NPC128751
0.8444 Intermediate Similarity NPC246700
0.8402 Intermediate Similarity NPC230869
0.8398 Intermediate Similarity NPC106833
0.8398 Intermediate Similarity NPC469497
0.8385 Intermediate Similarity NPC219087
0.8383 Intermediate Similarity NPC469786
0.8383 Intermediate Similarity NPC259644
0.8383 Intermediate Similarity NPC469760
0.8383 Intermediate Similarity NPC469763
0.8383 Intermediate Similarity NPC469765
0.8383 Intermediate Similarity NPC25008
0.8383 Intermediate Similarity NPC73952
0.8371 Intermediate Similarity NPC176127
0.8368 Intermediate Similarity NPC476465
0.8359 Intermediate Similarity NPC477609
0.8333 Intermediate Similarity NPC80597
0.8333 Intermediate Similarity NPC212376
0.8333 Intermediate Similarity NPC211572
0.8333 Intermediate Similarity NPC75540
0.8333 Intermediate Similarity NPC70922
0.8325 Intermediate Similarity NPC476116
0.8315 Intermediate Similarity NPC276517
0.8304 Intermediate Similarity NPC282231
0.8286 Intermediate Similarity NPC474409
0.827 Intermediate Similarity NPC13880
0.8266 Intermediate Similarity NPC474561
0.8266 Intermediate Similarity NPC49954
0.8266 Intermediate Similarity NPC160105
0.8263 Intermediate Similarity NPC105818
0.8263 Intermediate Similarity NPC24678
0.8256 Intermediate Similarity NPC311276
0.8254 Intermediate Similarity NPC476098
0.8246 Intermediate Similarity NPC279918
0.8242 Intermediate Similarity NPC159856
0.8242 Intermediate Similarity NPC314372
0.8223 Intermediate Similarity NPC74360
0.8202 Intermediate Similarity NPC42979
0.8201 Intermediate Similarity NPC211813
0.8192 Intermediate Similarity NPC224764
0.8182 Intermediate Similarity NPC276657
0.8176 Intermediate Similarity NPC469785
0.8144 Intermediate Similarity NPC208284
0.8129 Intermediate Similarity NPC469762
0.8128 Intermediate Similarity NPC153042
0.8121 Intermediate Similarity NPC190296
0.8114 Intermediate Similarity NPC63751
0.8109 Intermediate Similarity NPC245348
0.8083 Intermediate Similarity NPC477111
0.8079 Intermediate Similarity NPC314603
0.8077 Intermediate Similarity NPC94943
0.8073 Intermediate Similarity NPC476124
0.8073 Intermediate Similarity NPC477113
0.8073 Intermediate Similarity NPC476121
0.8069 Intermediate Similarity NPC60006
0.8068 Intermediate Similarity NPC473764
0.8068 Intermediate Similarity NPC314940
0.8066 Intermediate Similarity NPC212535
0.806 Intermediate Similarity NPC130570
0.8057 Intermediate Similarity NPC54988
0.8046 Intermediate Similarity NPC194640
0.8031 Intermediate Similarity NPC270918
0.803 Intermediate Similarity NPC6215
0.8022 Intermediate Similarity NPC190007
0.8021 Intermediate Similarity NPC470500
0.801 Intermediate Similarity NPC470678
0.801 Intermediate Similarity NPC128084
0.8 Intermediate Similarity NPC11464
0.8 Intermediate Similarity NPC329793
0.799 Intermediate Similarity NPC477608
0.799 Intermediate Similarity NPC477607
0.7978 Intermediate Similarity NPC163421
0.7978 Intermediate Similarity NPC188387
0.7969 Intermediate Similarity NPC223427
0.7967 Intermediate Similarity NPC48938
0.7965 Intermediate Similarity NPC141353
0.7959 Intermediate Similarity NPC246518
0.7958 Intermediate Similarity NPC232727
0.7944 Intermediate Similarity NPC248454
0.7943 Intermediate Similarity NPC40779
0.7939 Intermediate Similarity NPC73767
0.7938 Intermediate Similarity NPC183777
0.7927 Intermediate Similarity NPC285558
0.7912 Intermediate Similarity NPC233936
0.791 Intermediate Similarity NPC78020
0.791 Intermediate Similarity NPC201700
0.7906 Intermediate Similarity NPC315957
0.7906 Intermediate Similarity NPC121772
0.7903 Intermediate Similarity NPC95783
0.79 Intermediate Similarity NPC264285
0.7889 Intermediate Similarity NPC267885
0.7889 Intermediate Similarity NPC469928
0.7876 Intermediate Similarity NPC476138
0.7876 Intermediate Similarity NPC245816
0.7876 Intermediate Similarity NPC475774
0.7874 Intermediate Similarity NPC92796
0.7874 Intermediate Similarity NPC135141
0.7872 Intermediate Similarity NPC329541
0.7871 Intermediate Similarity NPC473317
0.7861 Intermediate Similarity NPC213530
0.7861 Intermediate Similarity NPC193267
0.7857 Intermediate Similarity NPC80596
0.7847 Intermediate Similarity NPC295228
0.7847 Intermediate Similarity NPC477549
0.7845 Intermediate Similarity NPC59269
0.7845 Intermediate Similarity NPC111275
0.7845 Intermediate Similarity NPC151939
0.7833 Intermediate Similarity NPC110500
0.7833 Intermediate Similarity NPC149155
0.7833 Intermediate Similarity NPC203468
0.7831 Intermediate Similarity NPC110126
0.7826 Intermediate Similarity NPC84478
0.7824 Intermediate Similarity NPC199277
0.7824 Intermediate Similarity NPC471957
0.7824 Intermediate Similarity NPC135887
0.7821 Intermediate Similarity NPC252590
0.7818 Intermediate Similarity NPC84911
0.7814 Intermediate Similarity NPC71037
0.7812 Intermediate Similarity NPC19872
0.781 Intermediate Similarity NPC15801
0.7805 Intermediate Similarity NPC319232
0.7805 Intermediate Similarity NPC24370
0.7802 Intermediate Similarity NPC126709
0.7802 Intermediate Similarity NPC248041
0.7801 Intermediate Similarity NPC306376
0.78 Intermediate Similarity NPC8022
0.78 Intermediate Similarity NPC470799
0.78 Intermediate Similarity NPC477110
0.7797 Intermediate Similarity NPC471178
0.7788 Intermediate Similarity NPC207686
0.7784 Intermediate Similarity NPC469761
0.7784 Intermediate Similarity NPC469768
0.7784 Intermediate Similarity NPC469783
0.7784 Intermediate Similarity NPC469767
0.7784 Intermediate Similarity NPC469784
0.7784 Intermediate Similarity NPC15102
0.7784 Intermediate Similarity NPC469779
0.7784 Intermediate Similarity NPC469780
0.7778 Intermediate Similarity NPC326363
0.7772 Intermediate Similarity NPC163055
0.7772 Intermediate Similarity NPC469358
0.776 Intermediate Similarity NPC300688
0.7758 Intermediate Similarity NPC261195
0.7758 Intermediate Similarity NPC96102
0.7758 Intermediate Similarity NPC29886
0.7756 Intermediate Similarity NPC125597
0.7755 Intermediate Similarity NPC193777
0.7753 Intermediate Similarity NPC49217
0.775 Intermediate Similarity NPC470549
0.7747 Intermediate Similarity NPC84827
0.7747 Intermediate Similarity NPC14113
0.7747 Intermediate Similarity NPC145885
0.7746 Intermediate Similarity NPC39092
0.7745 Intermediate Similarity NPC280272
0.7744 Intermediate Similarity NPC165349
0.7744 Intermediate Similarity NPC274291
0.7744 Intermediate Similarity NPC329708
0.7744 Intermediate Similarity NPC47059
0.7744 Intermediate Similarity NPC264166

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC171171 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9535 High Similarity NPD5575 Clinical (unspecified phase)
0.92 High Similarity NPD1038 Approved
0.9 High Similarity NPD484 Approved
0.8983 High Similarity NPD1304 Clinical (unspecified phase)
0.8729 High Similarity NPD7948 Phase 1
0.8667 High Similarity NPD802 Phase 2
0.8542 High Similarity NPD6803 Clinical (unspecified phase)
0.8483 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.8448 Intermediate Similarity NPD5065 Approved
0.8446 Intermediate Similarity NPD5612 Discontinued
0.8368 Intermediate Similarity NPD2189 Approved
0.8368 Intermediate Similarity NPD2187 Approved
0.8247 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD1325 Approved
0.8171 Intermediate Similarity NPD1326 Approved
0.8171 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD4511 Phase 1
0.8138 Intermediate Similarity NPD3825 Phase 3
0.8081 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.8042 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.8021 Intermediate Similarity NPD4795 Phase 2
0.8 Intermediate Similarity NPD6242 Discontinued
0.7938 Intermediate Similarity NPD1392 Approved
0.7926 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7906 Intermediate Similarity NPD1739 Approved
0.7906 Intermediate Similarity NPD1740 Approved
0.7889 Intermediate Similarity NPD7112 Discontinued
0.7889 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD6595 Phase 3
0.7833 Intermediate Similarity NPD482 Approved
0.7833 Intermediate Similarity NPD9690 Approved
0.7831 Intermediate Similarity NPD786 Approved
0.7829 Intermediate Similarity NPD112 Approved
0.7829 Intermediate Similarity NPD9705 Discontinued
0.7824 Intermediate Similarity NPD3931 Approved
0.7824 Intermediate Similarity NPD3928 Approved
0.7805 Intermediate Similarity NPD7603 Discontinued
0.7784 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7772 Intermediate Similarity NPD2095 Phase 2
0.7772 Intermediate Similarity NPD2094 Phase 2
0.7772 Intermediate Similarity NPD2092 Phase 2
0.7771 Intermediate Similarity NPD604 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD3814 Phase 1
0.7758 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD4039 Approved
0.7744 Intermediate Similarity NPD4122 Approved
0.7744 Intermediate Similarity NPD31 Approved
0.7744 Intermediate Similarity NPD4034 Approved
0.7744 Intermediate Similarity NPD4037 Approved
0.7744 Intermediate Similarity NPD4033 Approved
0.7744 Intermediate Similarity NPD32 Approved
0.7744 Intermediate Similarity NPD4038 Approved
0.7744 Intermediate Similarity NPD4035 Approved
0.7744 Intermediate Similarity NPD4036 Approved
0.774 Intermediate Similarity NPD5140 Approved
0.774 Intermediate Similarity NPD5138 Approved
0.7739 Intermediate Similarity NPD3330 Phase 1
0.7738 Intermediate Similarity NPD1592 Phase 3
0.773 Intermediate Similarity NPD2096 Phase 2
0.773 Intermediate Similarity NPD2091 Phase 2
0.7716 Intermediate Similarity NPD5658 Approved
0.7709 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD925 Approved
0.7697 Intermediate Similarity NPD926 Approved
0.7688 Intermediate Similarity NPD5067 Phase 2
0.7688 Intermediate Similarity NPD5066 Phase 2
0.7684 Intermediate Similarity NPD9695 Approved
0.7681 Intermediate Similarity NPD4845 Discontinued
0.768 Intermediate Similarity NPD750 Phase 2
0.7676 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7668 Intermediate Similarity NPD2175 Phase 3
0.7668 Intermediate Similarity NPD2177 Approved
0.7668 Intermediate Similarity NPD2176 Approved
0.7665 Intermediate Similarity NPD7452 Approved
0.7665 Intermediate Similarity NPD7222 Phase 2
0.7665 Intermediate Similarity NPD7453 Approved
0.7654 Intermediate Similarity NPD425 Approved
0.7654 Intermediate Similarity NPD424 Approved
0.7653 Intermediate Similarity NPD5901 Discontinued
0.765 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.765 Intermediate Similarity NPD2144 Approved
0.7644 Intermediate Similarity NPD5559 Phase 2
0.7641 Intermediate Similarity NPD6975 Discontinued
0.7633 Intermediate Similarity NPD1722 Approved
0.7632 Intermediate Similarity NPD3404 Approved
0.7614 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD8431 Approved
0.7606 Intermediate Similarity NPD2383 Phase 1
0.7586 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7577 Intermediate Similarity NPD8396 Approved
0.7577 Intermediate Similarity NPD8395 Approved
0.7577 Intermediate Similarity NPD1768 Approved
0.7576 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD3100 Discontinued
0.7571 Intermediate Similarity NPD5255 Approved
0.7566 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7552 Intermediate Similarity NPD4418 Discontinued
0.7529 Intermediate Similarity NPD4462 Approved
0.7529 Intermediate Similarity NPD4463 Approved
0.7527 Intermediate Similarity NPD3038 Discontinued
0.7525 Intermediate Similarity NPD2616 Phase 3
0.7525 Intermediate Similarity NPD3003 Approved
0.7525 Intermediate Similarity NPD2615 Phase 3
0.7514 Intermediate Similarity NPD4703 Approved
0.7514 Intermediate Similarity NPD4076 Approved
0.7514 Intermediate Similarity NPD4079 Approved
0.7514 Intermediate Similarity NPD4702 Approved
0.7512 Intermediate Similarity NPD949 Phase 1
0.75 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7463 Intermediate Similarity NPD3354 Phase 2
0.7459 Intermediate Similarity NPD3505 Approved
0.7459 Intermediate Similarity NPD6159 Phase 2
0.7459 Intermediate Similarity NPD3506 Approved
0.7437 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD2172 Phase 1
0.7426 Intermediate Similarity NPD7470 Discontinued
0.7418 Intermediate Similarity NPD7558 Phase 2
0.7405 Intermediate Similarity NPD5100 Phase 3
0.7398 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD459 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD1685 Approved
0.7389 Intermediate Similarity NPD1684 Approved
0.7386 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD9706 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6158 Phase 2
0.7385 Intermediate Similarity NPD2952 Discontinued
0.7379 Intermediate Similarity NPD2021 Discontinued
0.7371 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD2916 Discontinued
0.734 Intermediate Similarity NPD4203 Approved
0.734 Intermediate Similarity NPD5936 Approved
0.734 Intermediate Similarity NPD5939 Approved
0.734 Intermediate Similarity NPD4204 Approved
0.7333 Intermediate Similarity NPD1404 Approved
0.7333 Intermediate Similarity NPD1403 Approved
0.7333 Intermediate Similarity NPD9398 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7322 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7322 Intermediate Similarity NPD2844 Phase 3
0.7322 Intermediate Similarity NPD2781 Approved
0.7312 Intermediate Similarity NPD2380 Approved
0.7312 Intermediate Similarity NPD2381 Approved
0.7312 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD2382 Approved
0.7308 Intermediate Similarity NPD2780 Approved
0.7308 Intermediate Similarity NPD2782 Approved
0.7306 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7306 Intermediate Similarity NPD5913 Phase 3
0.7304 Intermediate Similarity NPD8093 Discontinued
0.7302 Intermediate Similarity NPD5596 Phase 2
0.73 Intermediate Similarity NPD5426 Phase 3
0.7288 Intermediate Similarity NPD2882 Phase 1
0.7277 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD706 Phase 1
0.7273 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD996 Phase 2
0.7268 Intermediate Similarity NPD8094 Discontinued
0.7268 Intermediate Similarity NPD3922 Approved
0.7268 Intermediate Similarity NPD3921 Approved
0.7268 Intermediate Similarity NPD3923 Approved
0.7268 Intermediate Similarity NPD3924 Approved
0.7268 Intermediate Similarity NPD9689 Approved
0.7268 Intermediate Similarity NPD994 Phase 2
0.7263 Intermediate Similarity NPD2789 Approved
0.726 Intermediate Similarity NPD3402 Phase 1
0.7258 Intermediate Similarity NPD4128 Approved
0.7254 Intermediate Similarity NPD5117 Phase 2
0.7249 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD2837 Discontinued
0.7243 Intermediate Similarity NPD1078 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD3813 Approved
0.7238 Intermediate Similarity NPD5599 Discontinued
0.7233 Intermediate Similarity NPD5902 Approved
0.7233 Intermediate Similarity NPD5903 Approved
0.7231 Intermediate Similarity NPD4551 Phase 2
0.7228 Intermediate Similarity NPD6290 Phase 2
0.7206 Intermediate Similarity NPD3014 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD3013 Phase 3
0.72 Intermediate Similarity NPD8073 Approved
0.72 Intermediate Similarity NPD5669 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD3017 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD2509 Approved
0.7192 Intermediate Similarity NPD2510 Approved
0.7189 Intermediate Similarity NPD4454 Phase 2
0.7184 Intermediate Similarity NPD3717 Discontinued
0.7182 Intermediate Similarity NPD1554 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD4181 Approved
0.7179 Intermediate Similarity NPD6569 Phase 2
0.7176 Intermediate Similarity NPD6494 Phase 2
0.7174 Intermediate Similarity NPD2639 Approved
0.7174 Intermediate Similarity NPD2642 Approved
0.7171 Intermediate Similarity NPD4502 Phase 2
0.7164 Intermediate Similarity NPD4886 Phase 2
0.7164 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD4044 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data