Structure

Physi-Chem Properties

Molecular Weight:  160.1
Volume:  175.851
LogP:  1.499
LogD:  0.771
LogS:  -0.467
# Rotatable Bonds:  2
TPSA:  41.81
# H-Bond Aceptor:  2
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.689
Synthetic Accessibility Score:  1.795
Fsp3:  0.2
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.824
MDCK Permeability:  5.114376563142287e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.627
Human Intestinal Absorption (HIA):  0.24
20% Bioavailability (F20%):  0.06
30% Bioavailability (F30%):  0.252

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.862
Plasma Protein Binding (PPB):  17.49850082397461%
Volume Distribution (VD):  2.386
Pgp-substrate:  66.48832702636719%

ADMET: Metabolism

CYP1A2-inhibitor:  0.916
CYP1A2-substrate:  0.905
CYP2C19-inhibitor:  0.251
CYP2C19-substrate:  0.223
CYP2C9-inhibitor:  0.03
CYP2C9-substrate:  0.852
CYP2D6-inhibitor:  0.847
CYP2D6-substrate:  0.918
CYP3A4-inhibitor:  0.061
CYP3A4-substrate:  0.179

ADMET: Excretion

Clearance (CL):  8.828
Half-life (T1/2):  0.82

ADMET: Toxicity

hERG Blockers:  0.1
Human Hepatotoxicity (H-HT):  0.442
Drug-inuced Liver Injury (DILI):  0.043
AMES Toxicity:  0.093
Rat Oral Acute Toxicity:  0.898
Maximum Recommended Daily Dose:  0.929
Skin Sensitization:  0.8
Carcinogencity:  0.053
Eye Corrosion:  0.271
Eye Irritation:  0.335
Respiratory Toxicity:  0.952

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Similar NPs/Drugs  

  Natural Product: NPC96102

Natural Product ID:  NPC96102
Common Name*:   Tryptamine
IUPAC Name:   2-(1H-indol-3-yl)ethanamine
Synonyms:  
Standard InCHIKey:  APJYDQYYACXCRM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
SMILES:  NCCc1c[nH]c2c1cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL6640
PubChem CID:   1150
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000183] Tryptamines and derivatives

*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

☑ 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
NPT288 Individual Protein Serotonin 1a (5-HT1a) receptor Rattus norvegicus Ki = 170.0 nM PMID[469351]
NPT289 Individual Protein Serotonin 1b (5-HT1b) receptor Rattus norvegicus Ki = 10200.0 nM PMID[469351]
NPT292 Individual Protein Serotonin 2c (5-HT2c) receptor Homo sapiens Ki = 50.0 nM PMID[469351]
NPT294 Individual Protein Serotonin 6 (5-HT6) receptor Homo sapiens Ki = 180.0 nM PMID[469352]
NPT1779 Individual Protein Serotonin 2b (5-HT2b) receptor Rattus norvegicus Kd = 537.03 nM PMID[469353]
NPT288 Individual Protein Serotonin 1a (5-HT1a) receptor Rattus norvegicus Ki = 169.82 nM PMID[469355]
NPT290 Individual Protein Serotonin 2a (5-HT2a) receptor Homo sapiens p[A50] = 6.1 n.a. PMID[469356]
NPT3595 Individual Protein Cathepsin K Homo sapiens IC50 = 15000.0 nM PMID[469359]
NPT2960 Individual Protein Brevianamide F prenyltransferase Aspergillus fumigatus Activity <= 5.3 % PMID[469360]
NPT2960 Individual Protein Brevianamide F prenyltransferase Aspergillus fumigatus Activity <= 1.1 % PMID[469360]
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency = 12589.3 nM PMID[469364]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 39810.7 nM PMID[469364]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 31622.8 nM PMID[469364]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 10322.5 nM PMID[469365]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 50118.7 nM PMID[469366]
NPT242 Individual Protein Dopamine D1 receptor Homo sapiens Potency n.a. 1299.5 nM PMID[469365]
NPT62 Individual Protein 6-phospho-1-fructokinase Trypanosoma brucei Potency n.a. 7568.6 nM PMID[469365]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 32629.4 nM PMID[469365]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens AC50 = 31622.78 nM PMID[469364]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 3162.28 nM PMID[469364]
NPT71 Cell Line HEK293 Homo sapiens Potency n.a. 29081.0 nM PMID[469365]
NPT242 Individual Protein Dopamine D1 receptor Homo sapiens Potency n.a. 25929.0 nM PMID[469365]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 6513.1 nM PMID[469366]
NPT294 Individual Protein Serotonin 6 (5-HT6) receptor Homo sapiens Ki = 70.0 nM PMID[469369]
NPT1634 Individual Protein Myeloperoxidase Homo sapiens IC50 = 770.0 nM PMID[469370]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[469371]
NPT104 Individual Protein Cerebroside-sulfatase Homo sapiens Potency n.a. 601.2 nM PMID[469365]
NPT105 Individual Protein Muscleblind-like protein 1 Homo sapiens Potency n.a. 141.3 nM PMID[469366]
NPT1073 Individual Protein Dopamine transporter Rattus norvegicus EC50 = 164.0 nM PMID[469374]
NPT1072 Individual Protein Serotonin transporter Rattus norvegicus EC50 = 32.6 nM PMID[469374]
NPT3986 Individual Protein Norepinephrine transporter Rattus norvegicus EC50 = 716.0 nM PMID[469374]
NPT290 Individual Protein Serotonin 2a (5-HT2a) receptor Homo sapiens EC50 = 7.36 nM PMID[469374]
NPT290 Individual Protein Serotonin 2a (5-HT2a) receptor Homo sapiens Emax = 104.0 % PMID[469374]
NPT240 Individual Protein Cytochrome P450 2A6 Homo sapiens Ki = 1700.0 nM PMID[469375]
NPT2599 Individual Protein Cytochrome P450 2A13 Homo sapiens Ki = 16000.0 nM PMID[469375]
NPT240 Individual Protein Cytochrome P450 2A6 Homo sapiens Kd = 2300.0 nM PMID[469375]
NPT2599 Individual Protein Cytochrome P450 2A13 Homo sapiens Kd = 5200.0 nM PMID[469375]
NPT1040 Individual Protein Human immunodeficiency virus type 1 Tat protein Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1) IC50 n.a. 11753.0 nM PMID[469366]
NPT1078 Individual Protein Indoleamine 2,3-dioxygenase Homo sapiens Activity = 0.0 % PMID[469376]
NPT1078 Individual Protein Indoleamine 2,3-dioxygenase Homo sapiens Ki = 160000.0 nM PMID[469377]
NPT4320 Individual Protein Trace amine-associated receptor 1 Rattus norvegicus EC50 = 310.0 nM PMID[469379]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 50000.0 nM PMID[469380]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 50000.0 nM PMID[469380]
NPT1785 Individual Protein Serotonin 7 (5-HT7) receptor Homo sapiens Ki = 158.49 nM PMID[469382]
NPT1078 Individual Protein Indoleamine 2,3-dioxygenase Homo sapiens Ki = 156000.0 nM PMID[469383]
NPT27 Others Unspecified Binding energy = 7.9 kCal mol-1 PMID[469349]
NPT2 Others Unspecified Ki = 5400.0 nM PMID[469350]
NPT969 Protein Family Adrenergic receptor alpha-2 Rattus norvegicus Ki = 19000.0 nM PMID[469350]
NPT1777 Protein Family Serotonin 2 (5-HT2) receptor Rattus norvegicus Ki = 2895.0 nM PMID[469351]
NPT1777 Protein Family Serotonin 2 (5-HT2) receptor Rattus norvegicus Ki = 50.0 nM PMID[469351]
NPT974 Individual Protein Serotonin 1d (5-HT1d) receptor Homo sapiens Ki = 23.0 nM PMID[469354]
NPT973 Individual Protein Serotonin 1b (5-HT1b) receptor Homo sapiens Ki = 36.0 nM PMID[469354]
NPT974 Individual Protein Serotonin 1d (5-HT1d) receptor Homo sapiens Ki = 61.0 nM PMID[469354]
NPT974 Individual Protein Serotonin 1d (5-HT1d) receptor Homo sapiens Selectivity = 1.7 n.a. PMID[469354]
NPT974 Individual Protein Serotonin 1d (5-HT1d) receptor Homo sapiens p[A50] = 6.9 n.a. PMID[469356]
NPT974 Individual Protein Serotonin 1d (5-HT1d) receptor Homo sapiens Intrinsic activity = 0.86 n.a. PMID[469356]
NPT24865 SINGLE PROTEIN Strictosidine synthase Catharanthus roseus Km = 7400.0 nM PMID[469357]
NPT27 Others Unspecified LogP app = -5.27 n.a. PMID[469358]
NPT35 Others n.a. LogP = 1.35 n.a. PMID[469358]
NPT2 Others Unspecified Activity <= 3.3 % PMID[469360]
NPT2 Others Unspecified Activity <= 1.0 % PMID[469360]
NPT35 Others n.a. Solubility = 80.0 ug.mL-1 PMID[469362]
NPT35 Others n.a. IC50 = 672000.0 nM PMID[469363]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 682000.0 nM PMID[469363]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 6000.0 nM PMID[469363]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. FC = 1.86 n.a. PMID[469363]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 31800.0 nM PMID[469363]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 10400.0 nM PMID[469363]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 13115.4 nM PMID[469366]
NPT4113 Organism Leptosphaeria maculans Leptosphaeria maculans GI = 12.0 % PMID[469368]
NPT4113 Organism Leptosphaeria maculans Leptosphaeria maculans GI = 15.0 % PMID[469368]
NPT4113 Organism Leptosphaeria maculans Leptosphaeria maculans GI = 28.0 % PMID[469368]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 104.08 % PMID[469372]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 101.01 % PMID[469372]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[469371]
NPT32 Organism Mus musculus Mus musculus MED < 25.0 mg kg-1 PMID[469373]
NPT27 Others Unspecified Ratio Ki = 9.4 n.a. PMID[469375]
NPT27 Others Unspecified Ratio = 2.3 n.a. PMID[469375]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. CC50 > 40000.0 nM PMID[469366]
NPT2 Others Unspecified IC50 n.a. 1660.0 nM PMID[469366]
NPT35 Others n.a. Retention_time = 9.0 min PMID[469376]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC > 51.0 ug.mL-1 PMID[469378]
NPT2 Others Unspecified Inhibition = -5.3 % PMID[469381]
NPT20 Organism Candida albicans Candida albicans MBIC50 > 128.0 ug ml-1 PMID[469384]
NPT20 Organism Candida albicans Candida albicans MBIC50 = 128.0 ug ml-1 PMID[469384]
NPT20 Organism Candida albicans Candida albicans MIC50 > 128.0 ug.mL-1 PMID[469384]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 17.65 % PMID[469385]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.09 % PMID[469386]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[469387]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[469387]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[469388]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[469388]

☑ 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 NPC96102 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
0.9922 High Similarity NPC84911
0.9922 High Similarity NPC105127
0.9845 High Similarity NPC261195
0.9845 High Similarity NPC29886
0.9771 High Similarity NPC110126
0.9771 High Similarity NPC73767
0.9697 High Similarity NPC469779
0.9697 High Similarity NPC469780
0.9697 High Similarity NPC469761
0.9697 High Similarity NPC469784
0.9697 High Similarity NPC469768
0.9697 High Similarity NPC279081
0.9697 High Similarity NPC469783
0.9697 High Similarity NPC469767
0.9688 High Similarity NPC82295
0.9624 High Similarity NPC469766
0.9552 High Similarity NPC190296
0.9549 High Similarity NPC230002
0.9412 High Similarity NPC159856
0.9412 High Similarity NPC314372
0.9343 High Similarity NPC288838
0.9343 High Similarity NPC143872
0.9275 High Similarity NPC471957
0.9275 High Similarity NPC469811
0.9209 High Similarity NPC321911
0.9203 High Similarity NPC63545
0.9143 High Similarity NPC53947
0.9143 High Similarity NPC24678
0.9143 High Similarity NPC105818
0.9137 High Similarity NPC201380
0.9137 High Similarity NPC179787
0.9078 High Similarity NPC216713
0.9078 High Similarity NPC470823
0.9015 High Similarity NPC22079
0.9014 High Similarity NPC469765
0.9014 High Similarity NPC25008
0.9014 High Similarity NPC141926
0.9014 High Similarity NPC200214
0.9014 High Similarity NPC259644
0.9014 High Similarity NPC469786
0.9014 High Similarity NPC469763
0.9014 High Similarity NPC73952
0.9014 High Similarity NPC469760
0.9014 High Similarity NPC325903
0.8963 High Similarity NPC218268
0.8963 High Similarity NPC325252
0.8951 High Similarity NPC212376
0.8951 High Similarity NPC70922
0.8951 High Similarity NPC75540
0.8951 High Similarity NPC211572
0.8951 High Similarity NPC80597
0.8951 High Similarity NPC34844
0.8889 High Similarity NPC469785
0.8889 High Similarity NPC198988
0.8855 High Similarity NPC250361
0.8837 High Similarity NPC41174
0.8828 High Similarity NPC216643
0.8828 High Similarity NPC286427
0.8828 High Similarity NPC469762
0.8794 High Similarity NPC316069
0.8767 High Similarity NPC56765
0.8767 High Similarity NPC92796
0.8767 High Similarity NPC41257
0.8767 High Similarity NPC206819
0.8767 High Similarity NPC318065
0.8767 High Similarity NPC135141
0.8759 High Similarity NPC125746
0.8759 High Similarity NPC150259
0.8722 High Similarity NPC473762
0.8707 High Similarity NPC279918
0.8707 High Similarity NPC122141
0.8707 High Similarity NPC470204
0.8707 High Similarity NPC131718
0.8699 High Similarity NPC236711
0.8681 High Similarity NPC470233
0.8657 High Similarity NPC473587
0.8649 High Similarity NPC282231
0.8649 High Similarity NPC470203
0.8639 High Similarity NPC230869
0.8633 High Similarity NPC88097
0.8626 High Similarity NPC46358
0.8593 High Similarity NPC475428
0.8591 High Similarity NPC311276
0.8591 High Similarity NPC90723
0.8591 High Similarity NPC317105
0.8581 High Similarity NPC215584
0.8581 High Similarity NPC44773
0.8571 High Similarity NPC2949
0.8571 High Similarity NPC115611
0.8571 High Similarity NPC59084
0.8561 High Similarity NPC27740
0.8533 High Similarity NPC280864
0.8533 High Similarity NPC17751
0.8529 High Similarity NPC475450
0.8529 High Similarity NPC179365
0.8511 High Similarity NPC63157
0.8511 High Similarity NPC473868
0.8477 Intermediate Similarity NPC474561
0.8477 Intermediate Similarity NPC49954
0.8477 Intermediate Similarity NPC54988
0.8477 Intermediate Similarity NPC160105
0.8477 Intermediate Similarity NPC49217
0.8467 Intermediate Similarity NPC102423
0.8467 Intermediate Similarity NPC40779
0.8467 Intermediate Similarity NPC149265
0.8467 Intermediate Similarity NPC473930
0.8462 Intermediate Similarity NPC204141
0.8421 Intermediate Similarity NPC63751
0.8411 Intermediate Similarity NPC274229
0.8366 Intermediate Similarity NPC194411
0.8357 Intermediate Similarity NPC251722
0.8357 Intermediate Similarity NPC314102
0.8333 Intermediate Similarity NPC285731
0.8333 Intermediate Similarity NPC470440
0.8321 Intermediate Similarity NPC282398
0.8312 Intermediate Similarity NPC470498
0.8301 Intermediate Similarity NPC78020
0.8301 Intermediate Similarity NPC201700
0.8289 Intermediate Similarity NPC42372
0.8288 Intermediate Similarity NPC2272
0.8258 Intermediate Similarity NPC314603
0.8258 Intermediate Similarity NPC477611
0.8247 Intermediate Similarity NPC97343
0.8244 Intermediate Similarity NPC91958
0.8224 Intermediate Similarity NPC194640
0.8222 Intermediate Similarity NPC166424
0.8222 Intermediate Similarity NPC146373
0.8222 Intermediate Similarity NPC245244
0.8219 Intermediate Similarity NPC470111
0.8219 Intermediate Similarity NPC21605
0.8205 Intermediate Similarity NPC203468
0.8205 Intermediate Similarity NPC110500
0.8205 Intermediate Similarity NPC275305
0.8205 Intermediate Similarity NPC37423
0.8205 Intermediate Similarity NPC149155
0.8194 Intermediate Similarity NPC82331
0.8169 Intermediate Similarity NPC169433
0.8158 Intermediate Similarity NPC225018
0.8153 Intermediate Similarity NPC474958
0.8153 Intermediate Similarity NPC267885
0.8141 Intermediate Similarity NPC313791
0.8112 Intermediate Similarity NPC312092
0.8108 Intermediate Similarity NPC40070
0.8108 Intermediate Similarity NPC33421
0.8101 Intermediate Similarity NPC248454
0.8101 Intermediate Similarity NPC59269
0.8101 Intermediate Similarity NPC14113
0.8101 Intermediate Similarity NPC240088
0.8101 Intermediate Similarity NPC284775
0.8101 Intermediate Similarity NPC68354
0.8101 Intermediate Similarity NPC473380
0.8101 Intermediate Similarity NPC145885
0.8101 Intermediate Similarity NPC84827
0.8089 Intermediate Similarity NPC293216
0.8089 Intermediate Similarity NPC280297
0.806 Intermediate Similarity NPC182570
0.806 Intermediate Similarity NPC265605
0.806 Intermediate Similarity NPC48564
0.8056 Intermediate Similarity NPC284635
0.805 Intermediate Similarity NPC126709
0.805 Intermediate Similarity NPC11126
0.805 Intermediate Similarity NPC248041
0.805 Intermediate Similarity NPC283219
0.805 Intermediate Similarity NPC215795
0.805 Intermediate Similarity NPC265710
0.805 Intermediate Similarity NPC176199
0.8041 Intermediate Similarity NPC37548
0.8038 Intermediate Similarity NPC280852
0.8014 Intermediate Similarity NPC242556
0.8 Intermediate Similarity NPC232798
0.8 Intermediate Similarity NPC476454
0.8 Intermediate Similarity NPC16659
0.8 Intermediate Similarity NPC314919
0.8 Intermediate Similarity NPC101165
0.8 Intermediate Similarity NPC164228
0.7987 Intermediate Similarity NPC148592
0.7987 Intermediate Similarity NPC151939
0.7987 Intermediate Similarity NPC111275
0.797 Intermediate Similarity NPC143603
0.7955 Intermediate Similarity NPC148140
0.795 Intermediate Similarity NPC233936
0.795 Intermediate Similarity NPC307191
0.7937 Intermediate Similarity NPC55772
0.7937 Intermediate Similarity NPC213468
0.7937 Intermediate Similarity NPC276540
0.7937 Intermediate Similarity NPC233050
0.7908 Intermediate Similarity NPC474880
0.7908 Intermediate Similarity NPC221786
0.7908 Intermediate Similarity NPC475990
0.7901 Intermediate Similarity NPC163055
0.7901 Intermediate Similarity NPC220765
0.7895 Intermediate Similarity NPC51054
0.7895 Intermediate Similarity NPC81561
0.7895 Intermediate Similarity NPC476464
0.7888 Intermediate Similarity NPC300688
0.7871 Intermediate Similarity NPC478184
0.7862 Intermediate Similarity NPC104483
0.7862 Intermediate Similarity NPC471579
0.7853 Intermediate Similarity NPC477003
0.7853 Intermediate Similarity NPC228835

  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 NPC96102 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
1.0 High Similarity NPD198 Clinical (unspecified phase)
0.9771 High Similarity NPD786 Approved
0.9624 High Similarity NPD1722 Approved
0.9209 High Similarity NPD4374 Clinical (unspecified phase)
0.9209 High Similarity NPD3100 Discontinued
0.9143 High Similarity NPD2172 Phase 1
0.8881 High Similarity NPD2837 Discontinued
0.8707 High Similarity NPD1403 Approved
0.8707 High Similarity NPD1404 Approved
0.8647 High Similarity NPD991 Phase 2
0.8647 High Similarity NPD992 Clinical (unspecified phase)
0.8591 High Similarity NPD3323 Discontinued
0.8571 High Similarity NPD3943 Clinical (unspecified phase)
0.8523 High Similarity NPD1853 Clinical (unspecified phase)
0.8477 Intermediate Similarity NPD2642 Approved
0.8477 Intermediate Similarity NPD2639 Approved
0.8421 Intermediate Similarity NPD2641 Approved
0.8421 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD2640 Approved
0.8392 Intermediate Similarity NPD5254 Discontinued
0.8382 Intermediate Similarity NPD3654 Approved
0.8366 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.8357 Intermediate Similarity NPD1262 Discovery
0.8322 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.8321 Intermediate Similarity NPD3476 Approved
0.8321 Intermediate Similarity NPD3475 Approved
0.8312 Intermediate Similarity NPD3609 Approved
0.8312 Intermediate Similarity NPD3610 Approved
0.8235 Intermediate Similarity NPD2119 Approved
0.8235 Intermediate Similarity NPD2118 Approved
0.8231 Intermediate Similarity NPD4462 Approved
0.8231 Intermediate Similarity NPD4463 Approved
0.8219 Intermediate Similarity NPD4547 Phase 3
0.8205 Intermediate Similarity NPD5065 Approved
0.8205 Intermediate Similarity NPD482 Approved
0.8205 Intermediate Similarity NPD4128 Approved
0.82 Intermediate Similarity NPD1192 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD2006 Phase 2
0.8194 Intermediate Similarity NPD2007 Clinical (unspecified phase)
0.8163 Intermediate Similarity NPD2430 Phase 2
0.8162 Intermediate Similarity NPD9583 Approved
0.8153 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.8153 Intermediate Similarity NPD4075 Phase 2
0.8151 Intermediate Similarity NPD1683 Approved
0.8143 Intermediate Similarity NPD3385 Approved
0.8133 Intermediate Similarity NPD473 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD2580 Discontinued
0.8117 Intermediate Similarity NPD1248 Discontinued
0.8101 Intermediate Similarity NPD2144 Approved
0.8101 Intermediate Similarity NPD3506 Approved
0.8101 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.8101 Intermediate Similarity NPD4181 Approved
0.8101 Intermediate Similarity NPD3505 Approved
0.806 Intermediate Similarity NPD271 Approved
0.806 Intermediate Similarity NPD268 Approved
0.806 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.805 Intermediate Similarity NPD4076 Approved
0.805 Intermediate Similarity NPD4079 Approved
0.803 Intermediate Similarity NPD9396 Approved
0.803 Intermediate Similarity NPD9392 Approved
0.8015 Intermediate Similarity NPD269 Clinical (unspecified phase)
0.8015 Intermediate Similarity NPD9357 Approved
0.8014 Intermediate Similarity NPD4029 Approved
0.8014 Intermediate Similarity NPD4030 Approved
0.8014 Intermediate Similarity NPD4028 Approved
0.8 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6595 Phase 3
0.7986 Intermediate Similarity NPD768 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD2865 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD3038 Discontinued
0.795 Intermediate Similarity NPD1708 Approved
0.795 Intermediate Similarity NPD1895 Discontinued
0.795 Intermediate Similarity NPD1707 Approved
0.7949 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7947 Intermediate Similarity NPD976 Approved
0.7947 Intermediate Similarity NPD2165 Phase 1
0.7947 Intermediate Similarity NPD975 Approved
0.7947 Intermediate Similarity NPD977 Approved
0.7929 Intermediate Similarity NPD715 Phase 3
0.7901 Intermediate Similarity NPD5105 Approved
0.7901 Intermediate Similarity NPD2094 Phase 2
0.7901 Intermediate Similarity NPD5106 Approved
0.7901 Intermediate Similarity NPD2092 Phase 2
0.7901 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD1332 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD2095 Phase 2
0.7895 Intermediate Similarity NPD3113 Approved
0.7895 Intermediate Similarity NPD3115 Approved
0.7895 Intermediate Similarity NPD3114 Approved
0.7895 Intermediate Similarity NPD3112 Approved
0.7887 Intermediate Similarity NPD3944 Approved
0.7887 Intermediate Similarity NPD3942 Approved
0.7872 Intermediate Similarity NPD803 Phase 1
0.7853 Intermediate Similarity NPD2096 Phase 2
0.7853 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD2091 Phase 2
0.7842 Intermediate Similarity NPD1598 Discontinued
0.7806 Intermediate Similarity NPD2385 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD750 Phase 2
0.7785 Intermediate Similarity NPD5436 Phase 1
0.7785 Intermediate Similarity NPD1528 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD1255 Approved
0.7778 Intermediate Similarity NPD1254 Approved
0.7778 Intermediate Similarity NPD1253 Approved
0.7778 Intermediate Similarity NPD1256 Approved
0.7758 Intermediate Similarity NPD6217 Discontinued
0.7758 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD947 Approved
0.7711 Intermediate Similarity NPD5590 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD3961 Discontinued
0.7711 Intermediate Similarity NPD8431 Approved
0.7692 Intermediate Similarity NPD5315 Discontinued
0.7665 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD9598 Discontinued
0.7651 Intermediate Similarity NPD1918 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD3339 Approved
0.7635 Intermediate Similarity NPD1592 Phase 3
0.7619 Intermediate Similarity NPD2069 Approved
0.7619 Intermediate Similarity NPD2068 Approved
0.7619 Intermediate Similarity NPD2070 Approved
0.7619 Intermediate Similarity NPD2074 Approved
0.7619 Intermediate Similarity NPD2075 Approved
0.7619 Intermediate Similarity NPD2073 Approved
0.7619 Intermediate Similarity NPD2071 Approved
0.7619 Intermediate Similarity NPD2072 Approved
0.7616 Intermediate Similarity NPD1661 Suspended
0.7609 Intermediate Similarity NPD748 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD2310 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD6554 Approved
0.7603 Intermediate Similarity NPD45 Approved
0.7595 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD4880 Discontinued
0.7574 Intermediate Similarity NPD6180 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD1325 Approved
0.7562 Intermediate Similarity NPD1326 Approved
0.7548 Intermediate Similarity NPD2150 Discontinued
0.7548 Intermediate Similarity NPD2748 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD3833 Phase 3
0.7516 Intermediate Similarity NPD3835 Phase 3
0.7516 Intermediate Similarity NPD1567 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD5145 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD4649 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4640 Approved
0.75 Intermediate Similarity NPD680 Discontinued
0.75 Intermediate Similarity NPD4639 Approved
0.75 Intermediate Similarity NPD4638 Approved
0.75 Intermediate Similarity NPD4702 Approved
0.75 Intermediate Similarity NPD1251 Discontinued
0.75 Intermediate Similarity NPD4703 Approved
0.7485 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1227 Phase 2
0.7485 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD802 Phase 2
0.7485 Intermediate Similarity NPD1038 Approved
0.7467 Intermediate Similarity NPD4047 Discontinued
0.7451 Intermediate Similarity NPD1183 Approved
0.7442 Intermediate Similarity NPD7618 Phase 3
0.7442 Intermediate Similarity NPD7619 Phase 3
0.7415 Intermediate Similarity NPD490 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD3117 Approved
0.7407 Intermediate Similarity NPD3116 Approved
0.7405 Intermediate Similarity NPD9099 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD9098 Phase 3
0.7399 Intermediate Similarity NPD6278 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD2960 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD3341 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD2390 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD5021 Discontinued
0.7375 Intermediate Similarity NPD2720 Phase 1
0.7375 Intermediate Similarity NPD2719 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD4112 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD972 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD6664 Approved
0.7356 Intermediate Similarity NPD7948 Phase 1
0.7329 Intermediate Similarity NPD1993 Approved
0.7329 Intermediate Similarity NPD1995 Approved
0.7329 Intermediate Similarity NPD1994 Approved
0.7308 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD6827 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD6828 Phase 2
0.7296 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD1030 Approved
0.729 Intermediate Similarity NPD1029 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD1027 Approved
0.7273 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3825 Phase 3
0.7273 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1313 Approved
0.7254 Intermediate Similarity NPD9253 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD200 Phase 2
0.7248 Intermediate Similarity NPD201 Phase 2
0.7232 Intermediate Similarity NPD484 Approved
0.7229 Intermediate Similarity NPD7111 Discontinued
0.7225 Intermediate Similarity NPD3404 Approved
0.7225 Intermediate Similarity NPD4615 Phase 2
0.7219 Intermediate Similarity NPD7564 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