NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	207.13
Volume:	219.663
LogP:	1.352
LogD:	1.341
LogS:	-0.884
# Rotatable Bonds:	2
TPSA:	30.49
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	2.652
Fsp3:	0.5
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:	-4.646
MDCK Permeability:	1.804915336833801e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.206
30% Bioavailability (F30%):	0.72

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.869
Plasma Protein Binding (PPB):	29.126907348632812%
Volume Distribution (VD):	2.606
Pgp-substrate:	59.50886154174805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.202
CYP1A2-substrate:	0.817
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.245
CYP2D6-inhibitor:	0.32
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.747

ADMET: Excretion

Clearance (CL):	7.969
Half-life (T1/2):	0.625

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.852
Drug-inuced Liver Injury (DILI):	0.349
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.615
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.147
Carcinogencity:	0.054
Eye Corrosion:	0.015
Eye Irritation:	0.044
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC253429

Natural Product ID:	NPC253429
*Common Name:**	Salsolidine
IUPAC Name:	(1S)-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline
Synonyms:	Salsolidine
Standard InCHIKey:	HMYJLVDKPJHJCF-QMMMGPOBSA-N
Standard InCHI:	InChI=1S/C12H17NO2/c1-8-10-7-12(15-3)11(14-2)6-9(10)4-5-13-8/h6-8,13H,4-5H2,1-3H3/t8-/m0/s1
SMILES:	COc1cc2[C@H](C)NCCc2cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1196026
PubChem CID:	164752
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002955] Tetrahydroisoquinolines

*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
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17511147]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	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

Activity Type	# Activity
Others	4
Potency	3

Activity Type	# Activity
Individual Protein	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	15848.9	nM	PMID[507929]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[507929]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-3.39	%	PMID[507930]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-4.57	%	PMID[507930]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	117.33	%	PMID[507931]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	93.8	%	PMID[507931]

☑ 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 NPC253429 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	283
0.1-0.2	2472
0.2-0.3	12910
0.3-0.4	4593
0.4-0.5	11042
0.5-0.6	8651
0.6-0.7	1950
0.7-0.8	605
0.8-0.85	125
0.85-0.9	56
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.969	High Similarity	NPC160692
0.9412	High Similarity	NPC294249
0.9308	High Similarity	NPC160193
0.9214	High Similarity	NPC207824
0.9214	High Similarity	NPC60538
0.9118	High Similarity	NPC314682
0.9085	High Similarity	NPC277669
0.9085	High Similarity	NPC76213
0.9051	High Similarity	NPC188163
0.9051	High Similarity	NPC328750
0.9051	High Similarity	NPC474915
0.9051	High Similarity	NPC213206
0.8921	High Similarity	NPC136860
0.8921	High Similarity	NPC476567
0.8921	High Similarity	NPC128019
0.8897	High Similarity	NPC187022
0.8897	High Similarity	NPC80129
0.8846	High Similarity	NPC217277
0.8836	High Similarity	NPC170503
0.8836	High Similarity	NPC203784
0.8836	High Similarity	NPC126519
0.8828	High Similarity	NPC477564
0.8828	High Similarity	NPC2295
0.8794	High Similarity	NPC185838
0.8769	High Similarity	NPC298486
0.8759	High Similarity	NPC7018
0.8759	High Similarity	NPC131204
0.8759	High Similarity	NPC301050
0.8671	High Similarity	NPC179825
0.8671	High Similarity	NPC210437
0.8671	High Similarity	NPC321505
0.8671	High Similarity	NPC106295
0.8671	High Similarity	NPC476144
0.8671	High Similarity	NPC51957
0.8671	High Similarity	NPC16107
0.8671	High Similarity	NPC191376
0.8662	High Similarity	NPC130926
0.8611	High Similarity	NPC476571
0.8611	High Similarity	NPC135538
0.8611	High Similarity	NPC246587
0.8611	High Similarity	NPC24233
0.8611	High Similarity	NPC475959
0.8611	High Similarity	NPC7467
0.8611	High Similarity	NPC428
0.8611	High Similarity	NPC147390
0.8603	High Similarity	NPC33338
0.8603	High Similarity	NPC302171
0.8603	High Similarity	NPC300020
0.8582	High Similarity	NPC172403
0.8543	High Similarity	NPC475393
0.8542	High Similarity	NPC476151
0.8493	Intermediate Similarity	NPC151895
0.8493	Intermediate Similarity	NPC97221
0.8493	Intermediate Similarity	NPC88249
0.8493	Intermediate Similarity	NPC220858
0.8493	Intermediate Similarity	NPC192768
0.8487	Intermediate Similarity	NPC2770
0.8487	Intermediate Similarity	NPC121275
0.8487	Intermediate Similarity	NPC39103
0.8487	Intermediate Similarity	NPC284183
0.8487	Intermediate Similarity	NPC4138
0.8435	Intermediate Similarity	NPC81733
0.8435	Intermediate Similarity	NPC476568
0.8435	Intermediate Similarity	NPC326316
0.8431	Intermediate Similarity	NPC304659
0.8431	Intermediate Similarity	NPC476573
0.8431	Intermediate Similarity	NPC81247
0.8431	Intermediate Similarity	NPC86144
0.8431	Intermediate Similarity	NPC35627
0.8425	Intermediate Similarity	NPC477565
0.8425	Intermediate Similarity	NPC103379
0.8409	Intermediate Similarity	NPC211992
0.8378	Intermediate Similarity	NPC233029
0.8378	Intermediate Similarity	NPC210148
0.8377	Intermediate Similarity	NPC204947
0.8367	Intermediate Similarity	NPC274026
0.8321	Intermediate Similarity	NPC262641
0.8311	Intermediate Similarity	NPC476579
0.8308	Intermediate Similarity	NPC120075
0.8301	Intermediate Similarity	NPC189470
0.8299	Intermediate Similarity	NPC92541
0.8299	Intermediate Similarity	NPC219162
0.8269	Intermediate Similarity	NPC477562
0.8269	Intermediate Similarity	NPC69712
0.8269	Intermediate Similarity	NPC26240
0.8269	Intermediate Similarity	NPC6152
0.8269	Intermediate Similarity	NPC109925
0.8267	Intermediate Similarity	NPC41178
0.8267	Intermediate Similarity	NPC39701
0.8267	Intermediate Similarity	NPC469817
0.8267	Intermediate Similarity	NPC78733
0.8267	Intermediate Similarity	NPC172765
0.8267	Intermediate Similarity	NPC54379
0.8267	Intermediate Similarity	NPC204828
0.8267	Intermediate Similarity	NPC325871
0.8267	Intermediate Similarity	NPC276588
0.8267	Intermediate Similarity	NPC184026
0.8267	Intermediate Similarity	NPC110416
0.8267	Intermediate Similarity	NPC189266
0.8267	Intermediate Similarity	NPC207757
0.8267	Intermediate Similarity	NPC249797
0.8267	Intermediate Similarity	NPC193949
0.8267	Intermediate Similarity	NPC138487
0.8267	Intermediate Similarity	NPC295691
0.8267	Intermediate Similarity	NPC127674
0.8267	Intermediate Similarity	NPC278799
0.8267	Intermediate Similarity	NPC99659
0.8267	Intermediate Similarity	NPC5238
0.8267	Intermediate Similarity	NPC2413
0.8267	Intermediate Similarity	NPC216459
0.8255	Intermediate Similarity	NPC148898
0.8255	Intermediate Similarity	NPC133011
0.8255	Intermediate Similarity	NPC82285
0.8239	Intermediate Similarity	NPC211468
0.8239	Intermediate Similarity	NPC219233
0.8239	Intermediate Similarity	NPC170170
0.8231	Intermediate Similarity	NPC130941
0.8217	Intermediate Similarity	NPC108434
0.8217	Intermediate Similarity	NPC475215
0.8212	Intermediate Similarity	NPC25084
0.8212	Intermediate Similarity	NPC146288
0.8212	Intermediate Similarity	NPC147091
0.8212	Intermediate Similarity	NPC247639
0.8182	Intermediate Similarity	NPC323123
0.8175	Intermediate Similarity	NPC291847
0.8165	Intermediate Similarity	NPC66341
0.8165	Intermediate Similarity	NPC477020
0.8165	Intermediate Similarity	NPC192135
0.8163	Intermediate Similarity	NPC144863
0.8163	Intermediate Similarity	NPC253883
0.8163	Intermediate Similarity	NPC90844
0.8163	Intermediate Similarity	NPC95075
0.8158	Intermediate Similarity	NPC476572
0.8133	Intermediate Similarity	NPC470924
0.8133	Intermediate Similarity	NPC37272
0.8133	Intermediate Similarity	NPC476580
0.8125	Intermediate Similarity	NPC323204
0.8121	Intermediate Similarity	NPC223125
0.8108	Intermediate Similarity	NPC37144
0.8108	Intermediate Similarity	NPC59907
0.8105	Intermediate Similarity	NPC477080
0.8105	Intermediate Similarity	NPC216816
0.8105	Intermediate Similarity	NPC111485
0.8105	Intermediate Similarity	NPC118804
0.8092	Intermediate Similarity	NPC234392
0.8092	Intermediate Similarity	NPC31311
0.8092	Intermediate Similarity	NPC160931
0.8092	Intermediate Similarity	NPC37205
0.8052	Intermediate Similarity	NPC249274
0.8052	Intermediate Similarity	NPC27410
0.8052	Intermediate Similarity	NPC232924
0.8052	Intermediate Similarity	NPC205167
0.8052	Intermediate Similarity	NPC166014
0.8052	Intermediate Similarity	NPC477559
0.8052	Intermediate Similarity	NPC306902
0.8052	Intermediate Similarity	NPC160298
0.8052	Intermediate Similarity	NPC266753
0.8038	Intermediate Similarity	NPC152212
0.8028	Intermediate Similarity	NPC11147
0.8026	Intermediate Similarity	NPC93593
0.8013	Intermediate Similarity	NPC223124
0.8	Intermediate Similarity	NPC476570
0.8	Intermediate Similarity	NPC470925
0.7987	Intermediate Similarity	NPC59028
0.7987	Intermediate Similarity	NPC92191
0.7974	Intermediate Similarity	NPC57512
0.7972	Intermediate Similarity	NPC416184
0.7963	Intermediate Similarity	NPC258695
0.7963	Intermediate Similarity	NPC470879
0.7963	Intermediate Similarity	NPC267408
0.7963	Intermediate Similarity	NPC474507
0.7963	Intermediate Similarity	NPC243454
0.7963	Intermediate Similarity	NPC475479
0.7956	Intermediate Similarity	NPC105513
0.795	Intermediate Similarity	NPC112575
0.795	Intermediate Similarity	NPC173416
0.795	Intermediate Similarity	NPC148709
0.795	Intermediate Similarity	NPC476577
0.7949	Intermediate Similarity	NPC124433
0.7949	Intermediate Similarity	NPC293871
0.7949	Intermediate Similarity	NPC324144
0.7949	Intermediate Similarity	NPC476569
0.7947	Intermediate Similarity	NPC85747
0.7947	Intermediate Similarity	NPC8337
0.7947	Intermediate Similarity	NPC119669
0.7943	Intermediate Similarity	NPC118419
0.7937	Intermediate Similarity	NPC4669
0.7935	Intermediate Similarity	NPC97072
0.7935	Intermediate Similarity	NPC215829
0.7922	Intermediate Similarity	NPC79328
0.7914	Intermediate Similarity	NPC474506
0.7914	Intermediate Similarity	NPC155442
0.7914	Intermediate Similarity	NPC476574
0.7914	Intermediate Similarity	NPC477561
0.7914	Intermediate Similarity	NPC312918
0.7914	Intermediate Similarity	NPC32413
0.7914	Intermediate Similarity	NPC239584
0.7908	Intermediate Similarity	NPC244112
0.7901	Intermediate Similarity	NPC23219
0.7898	Intermediate Similarity	NPC302527

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 NPC253429 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	750
0.2-0.3	1189
0.3-0.4	1860
0.4-0.5	2814
0.5-0.6	1559
0.6-0.7	601
0.7-0.8	182
0.8-0.85	13
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9051	High Similarity	NPD4664	Clinical (unspecified phase)
0.8944	High Similarity	NPD6030	Approved
0.8944	High Similarity	NPD6031	Approved
0.8897	High Similarity	NPD7298	Approved
0.8671	High Similarity	NPD4584	Approved
0.8593	High Similarity	NPD2669	Clinical (unspecified phase)
0.8552	High Similarity	NPD3641	Approved
0.8552	High Similarity	NPD3640	Phase 3
0.8552	High Similarity	NPD3639	Approved
0.8467	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD4017	Approved
0.8414	Intermediate Similarity	NPD1424	Approved
0.8366	Intermediate Similarity	NPD6107	Approved
0.8322	Intermediate Similarity	NPD4772	Phase 2
0.8322	Intermediate Similarity	NPD4773	Phase 2
0.8312	Intermediate Similarity	NPD4166	Phase 2
0.8129	Intermediate Similarity	NPD5718	Phase 2
0.8108	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6297	Approved
0.7986	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5241	Discontinued
0.7949	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD3060	Approved
0.7945	Intermediate Similarity	NPD4162	Approved
0.7905	Intermediate Similarity	NPD3845	Phase 1
0.7902	Intermediate Similarity	NPD2653	Approved
0.7866	Intermediate Similarity	NPD6853	Approved
0.7866	Intermediate Similarity	NPD6851	Approved
0.7852	Intermediate Similarity	NPD3124	Discontinued
0.7848	Intermediate Similarity	NPD4010	Discontinued
0.7803	Intermediate Similarity	NPD595	Approved
0.7803	Intermediate Similarity	NPD593	Approved
0.78	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2120	Phase 2
0.7778	Intermediate Similarity	NPD2989	Phase 2
0.7778	Intermediate Similarity	NPD2986	Phase 2
0.777	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7153	Discontinued
0.7755	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2898	Approved
0.7742	Intermediate Similarity	NPD4585	Approved
0.774	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6896	Approved
0.7724	Intermediate Similarity	NPD6895	Approved
0.7692	Intermediate Similarity	NPD3530	Approved
0.7692	Intermediate Similarity	NPD3532	Approved
0.7692	Intermediate Similarity	NPD3531	Approved
0.7692	Intermediate Similarity	NPD2674	Phase 3
0.7682	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5720	Discontinued
0.7654	Intermediate Similarity	NPD8251	Approved
0.7654	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8099	Discontinued
0.7654	Intermediate Similarity	NPD8252	Approved
0.7643	Intermediate Similarity	NPD3053	Approved
0.7643	Intermediate Similarity	NPD6788	Approved
0.7643	Intermediate Similarity	NPD3055	Approved
0.7628	Intermediate Similarity	NPD2977	Approved
0.7628	Intermediate Similarity	NPD2978	Approved
0.7628	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1336	Approved
0.7607	Intermediate Similarity	NPD5313	Approved
0.7607	Intermediate Similarity	NPD5312	Approved
0.7607	Intermediate Similarity	NPD8156	Discontinued
0.7605	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5976	Discontinued
0.758	Intermediate Similarity	NPD2560	Approved
0.758	Intermediate Similarity	NPD2563	Approved
0.7562	Intermediate Similarity	NPD7802	Discontinued
0.7545	Intermediate Similarity	NPD6618	Phase 2
0.7534	Intermediate Similarity	NPD817	Approved
0.7534	Intermediate Similarity	NPD823	Approved
0.7532	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3109	Approved
0.7517	Intermediate Similarity	NPD3110	Approved
0.7516	Intermediate Similarity	NPD6071	Discontinued
0.75	Intermediate Similarity	NPD3156	Discontinued
0.75	Intermediate Similarity	NPD1420	Approved
0.75	Intermediate Similarity	NPD3145	Approved
0.75	Intermediate Similarity	NPD3144	Approved
0.75	Intermediate Similarity	NPD1421	Approved
0.75	Intermediate Similarity	NPD7598	Phase 2
0.7485	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7833	Phase 2
0.7484	Intermediate Similarity	NPD7831	Phase 2
0.7484	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5160	Discontinued
0.7469	Intermediate Similarity	NPD4083	Discontinued
0.7468	Intermediate Similarity	NPD4727	Phase 1
0.7468	Intermediate Similarity	NPD5978	Approved
0.7468	Intermediate Similarity	NPD5977	Approved
0.7467	Intermediate Similarity	NPD2460	Phase 3
0.7467	Intermediate Similarity	NPD2459	Approved
0.7467	Intermediate Similarity	NPD2458	Approved
0.7448	Intermediate Similarity	NPD1136	Approved
0.7448	Intermediate Similarity	NPD4475	Approved
0.7448	Intermediate Similarity	NPD1132	Approved
0.7448	Intermediate Similarity	NPD1130	Approved
0.7448	Intermediate Similarity	NPD4474	Approved
0.7434	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2155	Approved
0.7432	Intermediate Similarity	NPD2156	Approved
0.7432	Intermediate Similarity	NPD2154	Approved
0.7407	Intermediate Similarity	NPD3051	Approved
0.74	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1817	Approved
0.7394	Intermediate Similarity	NPD1820	Approved
0.7394	Intermediate Similarity	NPD1818	Approved
0.7394	Intermediate Similarity	NPD1819	Approved
0.7389	Intermediate Similarity	NPD7110	Phase 1
0.7389	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1039	Discontinued
0.7379	Intermediate Similarity	NPD598	Approved
0.7379	Intermediate Similarity	NPD601	Approved
0.7379	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD597	Approved
0.7362	Intermediate Similarity	NPD2970	Approved
0.7362	Intermediate Similarity	NPD6687	Approved
0.7362	Intermediate Similarity	NPD2969	Approved
0.7362	Intermediate Similarity	NPD6688	Approved
0.7355	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1341	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2874	Phase 2
0.7337	Intermediate Similarity	NPD8054	Approved
0.7337	Intermediate Similarity	NPD8053	Approved
0.7329	Intermediate Similarity	NPD2245	Discovery
0.7325	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5310	Approved
0.7324	Intermediate Similarity	NPD5311	Approved
0.732	Intermediate Similarity	NPD7124	Phase 2
0.7317	Intermediate Similarity	NPD2489	Approved
0.7317	Intermediate Similarity	NPD27	Approved
0.7317	Intermediate Similarity	NPD4481	Phase 3
0.7315	Intermediate Similarity	NPD1753	Discontinued
0.7308	Intermediate Similarity	NPD3686	Approved
0.7308	Intermediate Similarity	NPD3687	Approved
0.7303	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2492	Phase 1
0.729	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD52	Approved
0.729	Intermediate Similarity	NPD7526	Approved
0.7273	Intermediate Similarity	NPD1774	Approved
0.7273	Intermediate Similarity	NPD2420	Approved
0.7273	Intermediate Similarity	NPD2421	Approved
0.7267	Intermediate Similarity	NPD1309	Phase 2
0.7267	Intermediate Similarity	NPD1307	Phase 2
0.7267	Intermediate Similarity	NPD4055	Discovery
0.7255	Intermediate Similarity	NPD3692	Discontinued
0.7255	Intermediate Similarity	NPD2677	Approved
0.7254	Intermediate Similarity	NPD1669	Approved
0.7248	Intermediate Similarity	NPD6111	Discontinued
0.7241	Intermediate Similarity	NPD600	Approved
0.7241	Intermediate Similarity	NPD596	Approved
0.7237	Intermediate Similarity	NPD5177	Phase 3
0.7237	Intermediate Similarity	NPD4236	Phase 3
0.7237	Intermediate Similarity	NPD4237	Approved
0.7233	Intermediate Similarity	NPD1769	Discontinued
0.7222	Intermediate Similarity	NPD7905	Discontinued
0.7219	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6875	Approved
0.7215	Intermediate Similarity	NPD6876	Approved
0.7214	Intermediate Similarity	NPD2667	Approved
0.7214	Intermediate Similarity	NPD2668	Approved
0.7206	Intermediate Similarity	NPD5283	Phase 1
0.7197	Intermediate Similarity	NPD2883	Discontinued
0.7192	Intermediate Similarity	NPD3165	Approved
0.7192	Intermediate Similarity	NPD3167	Approved
0.7192	Intermediate Similarity	NPD3164	Approved
0.7192	Intermediate Similarity	NPD3166	Approved
0.7181	Intermediate Similarity	NPD3054	Approved
0.7181	Intermediate Similarity	NPD3052	Approved
0.7179	Intermediate Similarity	NPD1350	Approved
0.7179	Intermediate Similarity	NPD1351	Approved
0.7179	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1349	Approved
0.7176	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1794	Approved
0.7152	Intermediate Similarity	NPD4005	Discontinued
0.7152	Intermediate Similarity	NPD824	Approved
0.7152	Intermediate Similarity	NPD2161	Phase 2
0.7143	Intermediate Similarity	NPD3920	Phase 2
0.7143	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3049	Approved
0.7133	Intermediate Similarity	NPD2428	Approved
0.7133	Intermediate Similarity	NPD2429	Approved
0.7126	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1102	Approved
0.7122	Intermediate Similarity	NPD1103	Approved
0.711	Intermediate Similarity	NPD7291	Discontinued
0.711	Intermediate Similarity	NPD3349	Phase 2
0.7107	Intermediate Similarity	NPD4180	Approved
0.7107	Intermediate Similarity	NPD4179	Approved
0.7105	Intermediate Similarity	NPD3656	Approved

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