NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	174.12
Volume:	193.147
LogP:	1.854
LogD:	1.57
LogS:	-1.281
# Rotatable Bonds:	3
TPSA:	27.82
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	1.849
Fsp3:	0.273
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:	-4.669
MDCK Permeability:	1.1738110515580047e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.467
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.816
Plasma Protein Binding (PPB):	31.424840927124023%
Volume Distribution (VD):	3.175
Pgp-substrate:	59.13859558105469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.411
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.624
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.766
CYP2D6-inhibitor:	0.831
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	8.562
Half-life (T1/2):	0.747

ADMET: Toxicity

hERG Blockers:	0.173
Human Hepatotoxicity (H-HT):	0.611
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.109
Rat Oral Acute Toxicity:	0.801
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.898
Carcinogencity:	0.032
Eye Corrosion:	0.018
Eye Irritation:	0.088
Respiratory Toxicity:	0.963

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC84911

Natural Product ID:	NPC84911
*Common Name:**	2-(1H-Indol-3-Yl)-N-Methylethanamine
IUPAC Name:	2-(1H-indol-3-yl)-N-methylethanamine
Synonyms:
Standard InCHIKey:	NCIKQJBVUNUXLW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
SMILES:	CNCCc1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL348588
PubChem CID:	6088
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

Activity Type	# Activity
EC50	5
Kd	1
Others	2
Potency	10

Activity Type	# Activity
Individual Protein	15
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1779	Individual Protein	Serotonin 2b (5-HT2b) receptor	Rattus norvegicus	Kd	=	1071.52	nM	PMID[447856]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PMID[447857]
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	22387.2	nM	PMID[447857]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[447857]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[447857]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[447857]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	EC50	=	321.0	nM	PMID[447858]
NPT1072	Individual Protein	Serotonin transporter	Rattus norvegicus	EC50	=	22.4	nM	PMID[447858]
NPT3986	Individual Protein	Norepinephrine transporter	Rattus norvegicus	EC50	=	733.0	nM	PMID[447858]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	EC50	=	50.7	nM	PMID[447858]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Emax	=	96.0	%	PMID[447858]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	49.8	%	PMID[447859]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	EC50	=	5100.0	nM	PMID[447857]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	17782.8	nM	PMID[447857]
NPT2	Others	Unspecified		Potency	=	4610.9	nM	PMID[447857]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[447857]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[447857]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	56234.1	nM	PMID[447857]

☑ 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 NPC84911 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1199
0.1-0.2	14679
0.2-0.3	17183
0.3-0.4	4288
0.4-0.5	2135
0.5-0.6	1583
0.6-0.7	958
0.7-0.8	489
0.8-0.85	83
0.85-0.9	48
0.9-0.95	34
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC29886
0.9922	High Similarity	NPC261195
0.9922	High Similarity	NPC96102
0.9847	High Similarity	NPC73767
0.9847	High Similarity	NPC110126
0.9846	High Similarity	NPC105127
0.9773	High Similarity	NPC469767
0.9773	High Similarity	NPC469784
0.9773	High Similarity	NPC469761
0.9773	High Similarity	NPC469783
0.9773	High Similarity	NPC469779
0.9773	High Similarity	NPC469768
0.9773	High Similarity	NPC469780
0.9699	High Similarity	NPC469766
0.9627	High Similarity	NPC190296
0.9624	High Similarity	NPC279081
0.9612	High Similarity	NPC82295
0.9485	High Similarity	NPC314372
0.9478	High Similarity	NPC230002
0.9348	High Similarity	NPC471957
0.9343	High Similarity	NPC159856
0.9281	High Similarity	NPC321911
0.9275	High Similarity	NPC143872
0.9275	High Similarity	NPC288838
0.9214	High Similarity	NPC53947
0.9214	High Similarity	NPC105818
0.9214	High Similarity	NPC24678
0.9209	High Similarity	NPC201380
0.9209	High Similarity	NPC179787
0.9209	High Similarity	NPC469811
0.9149	High Similarity	NPC470823
0.9137	High Similarity	NPC63545
0.9091	High Similarity	NPC22079
0.9085	High Similarity	NPC141926
0.9085	High Similarity	NPC469763
0.9085	High Similarity	NPC73952
0.9085	High Similarity	NPC469760
0.9085	High Similarity	NPC469765
0.9085	High Similarity	NPC25008
0.9085	High Similarity	NPC259644
0.9085	High Similarity	NPC469786
0.9085	High Similarity	NPC200214
0.9037	High Similarity	NPC325252
0.9021	High Similarity	NPC34844
0.9021	High Similarity	NPC80597
0.9021	High Similarity	NPC75540
0.9021	High Similarity	NPC211572
0.9021	High Similarity	NPC212376
0.9021	High Similarity	NPC70922
0.9014	High Similarity	NPC216713
0.8963	High Similarity	NPC198988
0.8951	High Similarity	NPC325903
0.8915	High Similarity	NPC41174
0.8897	High Similarity	NPC286427
0.8897	High Similarity	NPC218268
0.8836	High Similarity	NPC41257
0.8836	High Similarity	NPC56765
0.8836	High Similarity	NPC206819
0.8836	High Similarity	NPC318065
0.8832	High Similarity	NPC150259
0.8828	High Similarity	NPC469785
0.8788	High Similarity	NPC250361
0.8767	High Similarity	NPC236711
0.8767	High Similarity	NPC216643
0.8767	High Similarity	NPC469762
0.875	High Similarity	NPC470233
0.8732	High Similarity	NPC316069
0.8731	High Similarity	NPC473587
0.8716	High Similarity	NPC282231
0.8707	High Similarity	NPC135141
0.8707	High Similarity	NPC92796
0.8696	High Similarity	NPC125746
0.8667	High Similarity	NPC475428
0.8658	High Similarity	NPC311276
0.8658	High Similarity	NPC90723
0.8657	High Similarity	NPC473762
0.8649	High Similarity	NPC44773
0.8649	High Similarity	NPC279918
0.8649	High Similarity	NPC122141
0.8649	High Similarity	NPC131718
0.8649	High Similarity	NPC470204
0.8649	High Similarity	NPC215584
0.8643	High Similarity	NPC2949
0.8643	High Similarity	NPC59084
0.8643	High Similarity	NPC115611
0.8603	High Similarity	NPC179365
0.8603	High Similarity	NPC475450
0.8591	High Similarity	NPC470203
0.8582	High Similarity	NPC63157
0.8582	High Similarity	NPC473868
0.8581	High Similarity	NPC230869
0.8571	High Similarity	NPC88097
0.8561	High Similarity	NPC46358
0.8543	High Similarity	NPC160105
0.8543	High Similarity	NPC474561
0.8543	High Similarity	NPC49217
0.8543	High Similarity	NPC49954
0.8533	High Similarity	NPC40779
0.8533	High Similarity	NPC317105
0.8533	High Similarity	NPC149265
0.8496	Intermediate Similarity	NPC27740
0.8477	Intermediate Similarity	NPC280864
0.8477	Intermediate Similarity	NPC17751
0.8431	Intermediate Similarity	NPC194411
0.8429	Intermediate Similarity	NPC314102
0.8429	Intermediate Similarity	NPC251722
0.8421	Intermediate Similarity	NPC54988
0.8411	Intermediate Similarity	NPC102423
0.8406	Intermediate Similarity	NPC473930
0.8403	Intermediate Similarity	NPC470440
0.8403	Intermediate Similarity	NPC285731
0.8403	Intermediate Similarity	NPC204141
0.8377	Intermediate Similarity	NPC470498
0.8366	Intermediate Similarity	NPC201700
0.8366	Intermediate Similarity	NPC63751
0.8356	Intermediate Similarity	NPC2272
0.8355	Intermediate Similarity	NPC274229
0.8323	Intermediate Similarity	NPC314603
0.8289	Intermediate Similarity	NPC194640
0.8288	Intermediate Similarity	NPC470111
0.8288	Intermediate Similarity	NPC21605
0.8269	Intermediate Similarity	NPC37423
0.8269	Intermediate Similarity	NPC275305
0.8261	Intermediate Similarity	NPC282398
0.8258	Intermediate Similarity	NPC82331
0.8247	Intermediate Similarity	NPC78020
0.8235	Intermediate Similarity	NPC42372
0.8217	Intermediate Similarity	NPC474958
0.8217	Intermediate Similarity	NPC267885
0.8205	Intermediate Similarity	NPC313791
0.8205	Intermediate Similarity	NPC477611
0.8194	Intermediate Similarity	NPC97343
0.8182	Intermediate Similarity	NPC91958
0.8176	Intermediate Similarity	NPC40070
0.8176	Intermediate Similarity	NPC33421
0.8165	Intermediate Similarity	NPC14113
0.8165	Intermediate Similarity	NPC240088
0.8165	Intermediate Similarity	NPC473380
0.8165	Intermediate Similarity	NPC248454
0.8165	Intermediate Similarity	NPC145885
0.8165	Intermediate Similarity	NPC68354
0.8165	Intermediate Similarity	NPC84827
0.8162	Intermediate Similarity	NPC146373
0.8162	Intermediate Similarity	NPC245244
0.8162	Intermediate Similarity	NPC166424
0.8153	Intermediate Similarity	NPC149155
0.8153	Intermediate Similarity	NPC203468
0.8153	Intermediate Similarity	NPC293216
0.8153	Intermediate Similarity	NPC110500
0.8134	Intermediate Similarity	NPC182570
0.8134	Intermediate Similarity	NPC265605
0.8134	Intermediate Similarity	NPC48564
0.8113	Intermediate Similarity	NPC215795
0.8113	Intermediate Similarity	NPC265710
0.8113	Intermediate Similarity	NPC126709
0.8113	Intermediate Similarity	NPC11126
0.8113	Intermediate Similarity	NPC248041
0.8113	Intermediate Similarity	NPC176199
0.8112	Intermediate Similarity	NPC169433
0.8108	Intermediate Similarity	NPC37548
0.8105	Intermediate Similarity	NPC225018
0.8101	Intermediate Similarity	NPC280852
0.8082	Intermediate Similarity	NPC242556
0.8063	Intermediate Similarity	NPC16659
0.8063	Intermediate Similarity	NPC314919
0.8056	Intermediate Similarity	NPC312092
0.8054	Intermediate Similarity	NPC148592
0.805	Intermediate Similarity	NPC284775
0.805	Intermediate Similarity	NPC59269
0.805	Intermediate Similarity	NPC151939
0.8038	Intermediate Similarity	NPC280297
0.803	Intermediate Similarity	NPC148140
0.8012	Intermediate Similarity	NPC233936
0.8	Intermediate Similarity	NPC213468
0.8	Intermediate Similarity	NPC276540
0.8	Intermediate Similarity	NPC283219
0.8	Intermediate Similarity	NPC284635
0.8	Intermediate Similarity	NPC233050
0.7974	Intermediate Similarity	NPC221786
0.7974	Intermediate Similarity	NPC475990
0.7974	Intermediate Similarity	NPC474880
0.797	Intermediate Similarity	NPC81561
0.7963	Intermediate Similarity	NPC163055
0.7961	Intermediate Similarity	NPC51054
0.7961	Intermediate Similarity	NPC476464
0.795	Intermediate Similarity	NPC164228
0.795	Intermediate Similarity	NPC300688
0.7947	Intermediate Similarity	NPC232798
0.7945	Intermediate Similarity	NPC476454
0.7943	Intermediate Similarity	NPC101165
0.7937	Intermediate Similarity	NPC111275
0.7931	Intermediate Similarity	NPC104483
0.7919	Intermediate Similarity	NPC477134
0.7914	Intermediate Similarity	NPC204717
0.7914	Intermediate Similarity	NPC228835
0.791	Intermediate Similarity	NPC143603
0.7901	Intermediate Similarity	NPC191415
0.7901	Intermediate Similarity	NPC470677
0.7901	Intermediate Similarity	NPC243381
0.7901	Intermediate Similarity	NPC275292

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 NPC84911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	435
0.1-0.2	971
0.2-0.3	937
0.3-0.4	2052
0.4-0.5	2218
0.5-0.6	1620
0.6-0.7	690
0.7-0.8	179
0.8-0.85	36
0.85-0.9	7
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9922	High Similarity	NPD198	Clinical (unspecified phase)
0.9847	High Similarity	NPD786	Approved
0.9552	High Similarity	NPD1722	Approved
0.9281	High Similarity	NPD3100	Discontinued
0.9214	High Similarity	NPD2172	Phase 1
0.9143	High Similarity	NPD4374	Clinical (unspecified phase)
0.8819	High Similarity	NPD2837	Discontinued
0.8776	High Similarity	NPD1403	Approved
0.8776	High Similarity	NPD1404	Approved
0.8658	High Similarity	NPD3323	Discontinued
0.8643	High Similarity	NPD3943	Clinical (unspecified phase)
0.8582	High Similarity	NPD992	Clinical (unspecified phase)
0.8582	High Similarity	NPD991	Phase 2
0.8543	High Similarity	NPD2642	Approved
0.8543	High Similarity	NPD2639	Approved
0.8487	Intermediate Similarity	NPD2640	Approved
0.8487	Intermediate Similarity	NPD2641	Approved
0.8487	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD5254	Discontinued
0.8456	Intermediate Similarity	NPD3654	Approved
0.8431	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD3476	Approved
0.8394	Intermediate Similarity	NPD3475	Approved
0.8392	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD3610	Approved
0.8377	Intermediate Similarity	NPD3609	Approved
0.8366	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD2118	Approved
0.8309	Intermediate Similarity	NPD2119	Approved
0.8299	Intermediate Similarity	NPD4462	Approved
0.8299	Intermediate Similarity	NPD4463	Approved
0.8298	Intermediate Similarity	NPD1262	Discovery
0.8288	Intermediate Similarity	NPD4547	Phase 3
0.8269	Intermediate Similarity	NPD4128	Approved
0.8264	Intermediate Similarity	NPD2006	Phase 2
0.8235	Intermediate Similarity	NPD9583	Approved
0.8231	Intermediate Similarity	NPD2430	Phase 2
0.8219	Intermediate Similarity	NPD1683	Approved
0.8217	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD4075	Phase 2
0.8214	Intermediate Similarity	NPD3385	Approved
0.82	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2580	Discontinued
0.8182	Intermediate Similarity	NPD1248	Discontinued
0.8165	Intermediate Similarity	NPD3505	Approved
0.8165	Intermediate Similarity	NPD3506	Approved
0.8165	Intermediate Similarity	NPD2144	Approved
0.8165	Intermediate Similarity	NPD4181	Approved
0.8153	Intermediate Similarity	NPD5065	Approved
0.8153	Intermediate Similarity	NPD482	Approved
0.8146	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD268	Approved
0.8134	Intermediate Similarity	NPD271	Approved
0.8113	Intermediate Similarity	NPD4076	Approved
0.8113	Intermediate Similarity	NPD4079	Approved
0.8106	Intermediate Similarity	NPD9392	Approved
0.8106	Intermediate Similarity	NPD9396	Approved
0.8092	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD9357	Approved
0.8085	Intermediate Similarity	NPD4030	Approved
0.8085	Intermediate Similarity	NPD4028	Approved
0.8085	Intermediate Similarity	NPD4029	Approved
0.8063	Intermediate Similarity	NPD6595	Phase 3
0.805	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2165	Phase 1
0.8013	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3038	Discontinued
0.8012	Intermediate Similarity	NPD1707	Approved
0.8012	Intermediate Similarity	NPD1708	Approved
0.8	Intermediate Similarity	NPD715	Phase 3
0.7963	Intermediate Similarity	NPD5106	Approved
0.7963	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5105	Approved
0.7961	Intermediate Similarity	NPD3115	Approved
0.7961	Intermediate Similarity	NPD3112	Approved
0.7961	Intermediate Similarity	NPD3113	Approved
0.7961	Intermediate Similarity	NPD3114	Approved
0.7958	Intermediate Similarity	NPD3942	Approved
0.7958	Intermediate Similarity	NPD3944	Approved
0.795	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD1895	Discontinued
0.7895	Intermediate Similarity	NPD976	Approved
0.7895	Intermediate Similarity	NPD977	Approved
0.7895	Intermediate Similarity	NPD975	Approved
0.7871	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD750	Phase 2
0.7853	Intermediate Similarity	NPD2092	Phase 2
0.7853	Intermediate Similarity	NPD2095	Phase 2
0.7853	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD2094	Phase 2
0.7848	Intermediate Similarity	NPD5436	Phase 1
0.7847	Intermediate Similarity	NPD1256	Approved
0.7847	Intermediate Similarity	NPD1255	Approved
0.7847	Intermediate Similarity	NPD1253	Approved
0.7847	Intermediate Similarity	NPD1254	Approved
0.7818	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6217	Discontinued
0.7817	Intermediate Similarity	NPD803	Phase 1
0.7805	Intermediate Similarity	NPD2091	Phase 2
0.7805	Intermediate Similarity	NPD2096	Phase 2
0.7786	Intermediate Similarity	NPD1598	Discontinued
0.7771	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3961	Discontinued
0.7771	Intermediate Similarity	NPD8431	Approved
0.7771	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5315	Discontinued
0.7733	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1592	Phase 3
0.7687	Intermediate Similarity	NPD2070	Approved
0.7687	Intermediate Similarity	NPD2074	Approved
0.7687	Intermediate Similarity	NPD2071	Approved
0.7687	Intermediate Similarity	NPD2073	Approved
0.7687	Intermediate Similarity	NPD2072	Approved
0.7687	Intermediate Similarity	NPD2068	Approved
0.7687	Intermediate Similarity	NPD2069	Approved
0.7687	Intermediate Similarity	NPD2075	Approved
0.7681	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD947	Approved
0.7671	Intermediate Similarity	NPD45	Approved
0.7671	Intermediate Similarity	NPD6554	Approved
0.7665	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1326	Approved
0.7625	Intermediate Similarity	NPD1325	Approved
0.7613	Intermediate Similarity	NPD2150	Discontinued
0.7609	Intermediate Similarity	NPD9598	Discontinued
0.7597	Intermediate Similarity	NPD3339	Approved
0.7582	Intermediate Similarity	NPD3833	Phase 3
0.7582	Intermediate Similarity	NPD3835	Phase 3
0.7578	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD680	Discontinued
0.7566	Intermediate Similarity	NPD4703	Approved
0.7566	Intermediate Similarity	NPD4702	Approved
0.7566	Intermediate Similarity	NPD1661	Suspended
0.7562	Intermediate Similarity	NPD4639	Approved
0.7562	Intermediate Similarity	NPD4638	Approved
0.7562	Intermediate Similarity	NPD4640	Approved
0.7544	Intermediate Similarity	NPD802	Phase 2
0.7544	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD1038	Approved
0.7534	Intermediate Similarity	NPD4880	Discontinued
0.7533	Intermediate Similarity	NPD4047	Discontinued
0.7529	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7618	Phase 3
0.75	Intermediate Similarity	NPD7619	Phase 3
0.75	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD9098	Phase 3
0.7481	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3116	Approved
0.7469	Intermediate Similarity	NPD3117	Approved
0.7457	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5021	Discontinued
0.7453	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1251	Discontinued
0.7442	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1227	Phase 2
0.7423	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6664	Approved
0.7403	Intermediate Similarity	NPD1183	Approved
0.7397	Intermediate Similarity	NPD1993	Approved
0.7397	Intermediate Similarity	NPD1995	Approved
0.7397	Intermediate Similarity	NPD1994	Approved
0.7372	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6828	Phase 2
0.7362	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1030	Approved
0.7355	Intermediate Similarity	NPD1027	Approved
0.7349	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2720	Phase 1
0.7329	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1313	Approved
0.7315	Intermediate Similarity	NPD200	Phase 2
0.7315	Intermediate Similarity	NPD201	Phase 2
0.7314	Intermediate Similarity	NPD7948	Phase 1
0.7312	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7111	Discontinued
0.7283	Intermediate Similarity	NPD4615	Phase 2
0.7278	Intermediate Similarity	NPD7564	Discontinued
0.7273	Intermediate Similarity	NPD7469	Discontinued
0.7267	Intermediate Similarity	NPD5140	Approved
0.7267	Intermediate Similarity	NPD3583	Phase 2
0.7267	Intermediate Similarity	NPD5138	Approved
0.7255	Intermediate Similarity	NPD3401	Clinical (unspecified phase)

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