NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	163.1
Volume:	176.281
LogP:	1.65
LogD:	1.267
LogS:	-0.457
# Rotatable Bonds:	1
TPSA:	21.26
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.674
Synthetic Accessibility Score:	2.012
Fsp3:	0.4
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:	-4.605
MDCK Permeability:	2.502475217625033e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.945
Plasma Protein Binding (PPB):	16.915184020996094%
Volume Distribution (VD):	3.252
Pgp-substrate:	62.2236442565918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.612
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.224
CYP2C19-substrate:	0.9
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.579
CYP2D6-inhibitor:	0.96
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.376

ADMET: Excretion

Clearance (CL):	9.433
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.692
Drug-inuced Liver Injury (DILI):	0.281
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.649
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.731
Carcinogencity:	0.063
Eye Corrosion:	0.1
Eye Irritation:	0.096
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC217277

Natural Product ID:	NPC217277
*Common Name:**	7-Methoxy-1,2,3,4-Tetrahydroisoquinoline
IUPAC Name:	7-methoxy-1,2,3,4-tetrahydroisoquinoline
Synonyms:
Standard InCHIKey:	BPSLFSXCUJYFIR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H13NO/c1-12-10-3-2-8-4-5-11-7-9(8)6-10/h2-3,6,11H,4-5,7H2,1H3
SMILES:	COc1ccc2CCNCc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL26640
PubChem CID:	417288
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
NPO4880	Artemisia ifranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1652	Arichanna gaschkevitchii	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16366	Citrus cavaleriei	Species	Rutaceae	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
Ki	5
Others	1

Activity Type	# Activity
Individual Protein	3
Others	1
Protein Family	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Ki	=	20000.0	nM	PMID[531246]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Ki	=	50118723362727.15	nM	PMID[531247]
NPT1528	Individual Protein	Phenylethanolamine N-methyltransferase	Bos taurus	Ki	=	21000.0	nM	PMID[531248]
NPT969	Protein Family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	2137962089502232.5	nM	PMID[531247]
NPT969	Protein Family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	470.0	nM	PMID[531248]
NPT2	Others	Unspecified		Selectivity	=	0.022	n.a.	PMID[531248]

☑ 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 NPC217277 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	264
0.1-0.2	2861
0.2-0.3	12254
0.3-0.4	4591
0.4-0.5	11081
0.5-0.6	9263
0.6-0.7	1941
0.7-0.8	407
0.8-0.85	31
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9127	High Similarity	NPC160692
0.8846	High Similarity	NPC253429
0.8594	High Similarity	NPC160193
0.8456	Intermediate Similarity	NPC294249
0.8362	Intermediate Similarity	NPC42383
0.8286	Intermediate Similarity	NPC60538
0.8286	Intermediate Similarity	NPC207824
0.8209	Intermediate Similarity	NPC301050
0.8209	Intermediate Similarity	NPC7018
0.8209	Intermediate Similarity	NPC131204
0.8189	Intermediate Similarity	NPC298486
0.8169	Intermediate Similarity	NPC76213
0.8169	Intermediate Similarity	NPC277669
0.8162	Intermediate Similarity	NPC314682
0.8154	Intermediate Similarity	NPC172403
0.8151	Intermediate Similarity	NPC97811
0.8102	Intermediate Similarity	NPC328750
0.8102	Intermediate Similarity	NPC188163
0.8102	Intermediate Similarity	NPC213206
0.8102	Intermediate Similarity	NPC474915
0.8099	Intermediate Similarity	NPC21890
0.8092	Intermediate Similarity	NPC471306
0.8092	Intermediate Similarity	NPC471321
0.8067	Intermediate Similarity	NPC186469
0.8056	Intermediate Similarity	NPC477564
0.8056	Intermediate Similarity	NPC2295
0.8	Intermediate Similarity	NPC120075
0.7971	Intermediate Similarity	NPC470925
0.7945	Intermediate Similarity	NPC126519
0.7945	Intermediate Similarity	NPC203784
0.7945	Intermediate Similarity	NPC170503
0.791	Intermediate Similarity	NPC300020
0.791	Intermediate Similarity	NPC302171
0.791	Intermediate Similarity	NPC33338
0.7877	Intermediate Similarity	NPC80129
0.7877	Intermediate Similarity	NPC187022
0.7872	Intermediate Similarity	NPC185838
0.7872	Intermediate Similarity	NPC130926
0.7857	Intermediate Similarity	NPC476567
0.7857	Intermediate Similarity	NPC136860
0.7857	Intermediate Similarity	NPC128019
0.7852	Intermediate Similarity	NPC325568
0.7823	Intermediate Similarity	NPC26524
0.777	Intermediate Similarity	NPC79328
0.7762	Intermediate Similarity	NPC179825
0.7762	Intermediate Similarity	NPC321505
0.7762	Intermediate Similarity	NPC16107
0.7762	Intermediate Similarity	NPC210437
0.7762	Intermediate Similarity	NPC106295
0.7762	Intermediate Similarity	NPC51957
0.7762	Intermediate Similarity	NPC476151
0.7762	Intermediate Similarity	NPC191376
0.7762	Intermediate Similarity	NPC476144
0.7718	Intermediate Similarity	NPC7393
0.771	Intermediate Similarity	NPC328267
0.7708	Intermediate Similarity	NPC147390
0.7708	Intermediate Similarity	NPC135538
0.7708	Intermediate Similarity	NPC428
0.7708	Intermediate Similarity	NPC246587
0.7708	Intermediate Similarity	NPC476571
0.7708	Intermediate Similarity	NPC475959
0.7708	Intermediate Similarity	NPC7467
0.7708	Intermediate Similarity	NPC24233
0.7682	Intermediate Similarity	NPC475393
0.7681	Intermediate Similarity	NPC416184
0.7674	Intermediate Similarity	NPC289330
0.7674	Intermediate Similarity	NPC17388
0.7674	Intermediate Similarity	NPC321133
0.7674	Intermediate Similarity	NPC160120
0.7674	Intermediate Similarity	NPC53596
0.7674	Intermediate Similarity	NPC471308
0.7667	Intermediate Similarity	NPC241224
0.7655	Intermediate Similarity	NPC477565
0.7655	Intermediate Similarity	NPC103379
0.7639	Intermediate Similarity	NPC144863
0.7639	Intermediate Similarity	NPC95075
0.7639	Intermediate Similarity	NPC253883
0.7639	Intermediate Similarity	NPC90844
0.7634	Intermediate Similarity	NPC471314
0.7634	Intermediate Similarity	NPC471315
0.7632	Intermediate Similarity	NPC2770
0.7632	Intermediate Similarity	NPC39103
0.763	Intermediate Similarity	NPC262641
0.7603	Intermediate Similarity	NPC274026
0.7594	Intermediate Similarity	NPC318965
0.7589	Intermediate Similarity	NPC323204
0.7586	Intermediate Similarity	NPC59907
0.7586	Intermediate Similarity	NPC37144
0.7584	Intermediate Similarity	NPC29647
0.7582	Intermediate Similarity	NPC81247
0.7582	Intermediate Similarity	NPC476573
0.7582	Intermediate Similarity	NPC86144
0.7582	Intermediate Similarity	NPC35627
0.7582	Intermediate Similarity	NPC304659
0.7576	Intermediate Similarity	NPC140359
0.7576	Intermediate Similarity	NPC13020
0.7571	Intermediate Similarity	NPC170170
0.7571	Intermediate Similarity	NPC219233
0.7571	Intermediate Similarity	NPC211468
0.7566	Intermediate Similarity	NPC189470
0.7557	Intermediate Similarity	NPC211992
0.7551	Intermediate Similarity	NPC476579
0.7551	Intermediate Similarity	NPC326316
0.7551	Intermediate Similarity	NPC81733
0.7534	Intermediate Similarity	NPC92541
0.7534	Intermediate Similarity	NPC219162
0.7518	Intermediate Similarity	NPC323123
0.7516	Intermediate Similarity	NPC209377
0.7516	Intermediate Similarity	NPC4138
0.7516	Intermediate Similarity	NPC121275
0.7516	Intermediate Similarity	NPC284183
0.75	Intermediate Similarity	NPC82285
0.75	Intermediate Similarity	NPC133011
0.75	Intermediate Similarity	NPC148898
0.7483	Intermediate Similarity	NPC88249
0.7483	Intermediate Similarity	NPC220858
0.7483	Intermediate Similarity	NPC151895
0.7483	Intermediate Similarity	NPC192768
0.7483	Intermediate Similarity	NPC97221
0.7468	Intermediate Similarity	NPC223077
0.7468	Intermediate Similarity	NPC195392
0.7468	Intermediate Similarity	NPC193853
0.7468	Intermediate Similarity	NPC56887
0.7451	Intermediate Similarity	NPC293871
0.7451	Intermediate Similarity	NPC124433
0.7445	Intermediate Similarity	NPC476570
0.7432	Intermediate Similarity	NPC119669
0.7432	Intermediate Similarity	NPC476568
0.7419	Intermediate Similarity	NPC204947
0.74	Intermediate Similarity	NPC193949
0.74	Intermediate Similarity	NPC127674
0.74	Intermediate Similarity	NPC41178
0.74	Intermediate Similarity	NPC278799
0.74	Intermediate Similarity	NPC184026
0.74	Intermediate Similarity	NPC216459
0.74	Intermediate Similarity	NPC5238
0.74	Intermediate Similarity	NPC207757
0.74	Intermediate Similarity	NPC249797
0.74	Intermediate Similarity	NPC189266
0.74	Intermediate Similarity	NPC2413
0.74	Intermediate Similarity	NPC39701
0.74	Intermediate Similarity	NPC204828
0.74	Intermediate Similarity	NPC469817
0.74	Intermediate Similarity	NPC295691
0.74	Intermediate Similarity	NPC78733
0.74	Intermediate Similarity	NPC54379
0.74	Intermediate Similarity	NPC110416
0.74	Intermediate Similarity	NPC93593
0.74	Intermediate Similarity	NPC172765
0.74	Intermediate Similarity	NPC138487
0.74	Intermediate Similarity	NPC276588
0.7391	Intermediate Similarity	NPC118419
0.7389	Intermediate Similarity	NPC108434
0.7389	Intermediate Similarity	NPC475215
0.7388	Intermediate Similarity	NPC105513
0.7383	Intermediate Similarity	NPC26601
0.7383	Intermediate Similarity	NPC233029
0.7383	Intermediate Similarity	NPC210148
0.7383	Intermediate Similarity	NPC476580
0.7376	Intermediate Similarity	NPC318591
0.7376	Intermediate Similarity	NPC231163
0.7365	Intermediate Similarity	NPC223125
0.736	Intermediate Similarity	NPC24777
0.7351	Intermediate Similarity	NPC247639
0.7351	Intermediate Similarity	NPC147091
0.7351	Intermediate Similarity	NPC146288
0.7351	Intermediate Similarity	NPC25084
0.7347	Intermediate Similarity	NPC130941
0.7342	Intermediate Similarity	NPC66341
0.7342	Intermediate Similarity	NPC477020
0.7342	Intermediate Similarity	NPC192135
0.7338	Intermediate Similarity	NPC266425
0.7333	Intermediate Similarity	NPC320242
0.7328	Intermediate Similarity	NPC71853
0.7325	Intermediate Similarity	NPC109925
0.7325	Intermediate Similarity	NPC26240
0.7325	Intermediate Similarity	NPC69712
0.7325	Intermediate Similarity	NPC152212
0.7325	Intermediate Similarity	NPC6152
0.7325	Intermediate Similarity	NPC477562
0.7303	Intermediate Similarity	NPC476572
0.7285	Intermediate Similarity	NPC76079
0.7285	Intermediate Similarity	NPC123323
0.7285	Intermediate Similarity	NPC99659
0.7285	Intermediate Similarity	NPC325871
0.7279	Intermediate Similarity	NPC218323
0.7267	Intermediate Similarity	NPC114124
0.7267	Intermediate Similarity	NPC223124
0.7267	Intermediate Similarity	NPC470924
0.7266	Intermediate Similarity	NPC149379
0.7266	Intermediate Similarity	NPC93882
0.7266	Intermediate Similarity	NPC130595
0.7265	Intermediate Similarity	NPC321956
0.726	Intermediate Similarity	NPC110337
0.7255	Intermediate Similarity	NPC92191
0.7255	Intermediate Similarity	NPC59028
0.7255	Intermediate Similarity	NPC118804
0.7255	Intermediate Similarity	NPC106786
0.7252	Intermediate Similarity	NPC85276
0.7248	Intermediate Similarity	NPC13397

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 NPC217277 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	860
0.2-0.3	1018
0.3-0.4	1619
0.4-0.5	2892
0.5-0.6	1718
0.6-0.7	688
0.7-0.8	170
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8286	Intermediate Similarity	NPD6030	Approved
0.8286	Intermediate Similarity	NPD6031	Approved
0.8197	Intermediate Similarity	NPD593	Approved
0.8197	Intermediate Similarity	NPD595	Approved
0.8134	Intermediate Similarity	NPD2986	Phase 2
0.8134	Intermediate Similarity	NPD2989	Phase 2
0.8102	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD3156	Discontinued
0.8	Intermediate Similarity	NPD2120	Phase 2
0.7986	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD1424	Approved
0.7877	Intermediate Similarity	NPD7298	Approved
0.7852	Intermediate Similarity	NPD3109	Approved
0.7852	Intermediate Similarity	NPD3110	Approved
0.7836	Intermediate Similarity	NPD1039	Discontinued
0.7836	Intermediate Similarity	NPD1336	Approved
0.7817	Intermediate Similarity	NPD7598	Phase 2
0.7778	Intermediate Similarity	NPD4475	Approved
0.7778	Intermediate Similarity	NPD4474	Approved
0.7762	Intermediate Similarity	NPD4584	Approved
0.7734	Intermediate Similarity	NPD2594	Approved
0.7734	Intermediate Similarity	NPD2595	Approved
0.7734	Intermediate Similarity	NPD3049	Approved
0.7714	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD2428	Approved
0.771	Intermediate Similarity	NPD1420	Approved
0.771	Intermediate Similarity	NPD2429	Approved
0.771	Intermediate Similarity	NPD1421	Approved
0.771	Intermediate Similarity	NPD1669	Approved
0.7692	Intermediate Similarity	NPD3124	Discontinued
0.7674	Intermediate Similarity	NPD2556	Approved
0.7674	Intermediate Similarity	NPD2554	Approved
0.7674	Intermediate Similarity	NPD2667	Approved
0.7674	Intermediate Similarity	NPD2668	Approved
0.7655	Intermediate Similarity	NPD4727	Phase 1
0.7647	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5718	Phase 2
0.7571	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4017	Approved
0.755	Intermediate Similarity	NPD1309	Phase 2
0.755	Intermediate Similarity	NPD1307	Phase 2
0.7536	Intermediate Similarity	NPD1341	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3640	Phase 3
0.7534	Intermediate Similarity	NPD3641	Approved
0.7534	Intermediate Similarity	NPD3639	Approved
0.7519	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2245	Discovery
0.75	Intermediate Similarity	NPD2232	Approved
0.75	Intermediate Similarity	NPD2230	Approved
0.75	Intermediate Similarity	NPD2233	Approved
0.75	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5160	Discontinued
0.7426	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4162	Approved
0.7413	Intermediate Similarity	NPD3060	Approved
0.7413	Intermediate Similarity	NPD2460	Phase 3
0.7413	Intermediate Similarity	NPD2458	Approved
0.7413	Intermediate Similarity	NPD2459	Approved
0.7407	Intermediate Similarity	NPD7905	Discontinued
0.7403	Intermediate Similarity	NPD6107	Approved
0.7394	Intermediate Similarity	NPD3656	Approved
0.7391	Intermediate Similarity	NPD3532	Approved
0.7391	Intermediate Similarity	NPD3530	Approved
0.7391	Intermediate Similarity	NPD3531	Approved
0.7385	Intermediate Similarity	NPD2486	Discontinued
0.7376	Intermediate Similarity	NPD2154	Approved
0.7376	Intermediate Similarity	NPD2155	Approved
0.7376	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2156	Approved
0.7372	Intermediate Similarity	NPD5163	Phase 2
0.7368	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5267	Discontinued
0.7361	Intermediate Similarity	NPD6748	Discontinued
0.736	Intermediate Similarity	NPD550	Approved
0.736	Intermediate Similarity	NPD551	Approved
0.7357	Intermediate Similarity	NPD3052	Approved
0.7357	Intermediate Similarity	NPD2653	Approved
0.7357	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3054	Approved
0.7355	Intermediate Similarity	NPD4166	Phase 2
0.7348	Intermediate Similarity	NPD3294	Phase 2
0.7343	Intermediate Similarity	NPD7153	Discontinued
0.7333	Intermediate Similarity	NPD1820	Approved
0.7333	Intermediate Similarity	NPD1818	Approved
0.7333	Intermediate Similarity	NPD1817	Approved
0.7333	Intermediate Similarity	NPD4772	Phase 2
0.7333	Intermediate Similarity	NPD1819	Approved
0.7333	Intermediate Similarity	NPD4773	Phase 2
0.7328	Intermediate Similarity	NPD3444	Approved
0.7328	Intermediate Similarity	NPD3445	Approved
0.7328	Intermediate Similarity	NPD3443	Approved
0.7319	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1914	Approved
0.7297	Intermediate Similarity	NPD5976	Discontinued
0.7285	Intermediate Similarity	NPD1769	Discontinued
0.7285	Intermediate Similarity	NPD5720	Discontinued
0.7279	Intermediate Similarity	NPD2990	Approved
0.7279	Intermediate Similarity	NPD2987	Approved
0.7266	Intermediate Similarity	NPD2674	Phase 3
0.726	Intermediate Similarity	NPD3845	Phase 1
0.7254	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6380	Phase 1
0.7254	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD316	Approved
0.725	Intermediate Similarity	NPD6297	Approved
0.7248	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1024	Discontinued
0.7239	Intermediate Similarity	NPD2235	Phase 2
0.7239	Intermediate Similarity	NPD2231	Phase 2
0.7231	Intermediate Similarity	NPD3596	Phase 2
0.723	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4598	Approved
0.7222	Intermediate Similarity	NPD4597	Approved
0.7218	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4098	Discontinued
0.7197	Intermediate Similarity	NPD4093	Discontinued
0.7197	Intermediate Similarity	NPD6382	Discontinued
0.7194	Intermediate Similarity	NPD3145	Approved
0.7194	Intermediate Similarity	NPD3144	Approved
0.7192	Intermediate Similarity	NPD2677	Approved
0.7192	Intermediate Similarity	NPD3301	Approved
0.719	Intermediate Similarity	NPD5978	Approved
0.719	Intermediate Similarity	NPD5977	Approved
0.7183	Intermediate Similarity	NPD6895	Approved
0.7183	Intermediate Similarity	NPD6896	Approved
0.7176	Intermediate Similarity	NPD9615	Approved
0.7176	Intermediate Similarity	NPD856	Approved
0.7176	Intermediate Similarity	NPD9616	Approved
0.7176	Intermediate Similarity	NPD16	Approved
0.7176	Intermediate Similarity	NPD9613	Approved
0.7174	Intermediate Similarity	NPD600	Approved
0.7174	Intermediate Similarity	NPD596	Approved
0.7162	Intermediate Similarity	NPD2874	Phase 2
0.7154	Intermediate Similarity	NPD709	Approved
0.7152	Intermediate Similarity	NPD3679	Phase 2
0.7143	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7425	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1753	Discontinued
0.7122	Intermediate Similarity	NPD3166	Approved
0.7122	Intermediate Similarity	NPD3164	Approved
0.7122	Intermediate Similarity	NPD3165	Approved
0.7122	Intermediate Similarity	NPD3167	Approved
0.7121	Intermediate Similarity	NPD2106	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6090	Discontinued
0.7113	Intermediate Similarity	NPD2492	Phase 1
0.7101	Intermediate Similarity	NPD3637	Approved
0.7101	Intermediate Similarity	NPD3635	Approved
0.7101	Intermediate Similarity	NPD3636	Approved
0.7097	Intermediate Similarity	NPD9608	Approved
0.7097	Intermediate Similarity	NPD9610	Approved
0.7095	Intermediate Similarity	NPD6087	Phase 1
0.7092	Intermediate Similarity	NPD2238	Phase 2
0.7087	Intermediate Similarity	NPD1792	Phase 2
0.7086	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3053	Approved
0.708	Intermediate Similarity	NPD3055	Approved
0.708	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1794	Approved
0.7078	Intermediate Similarity	NPD2563	Approved
0.7078	Intermediate Similarity	NPD2560	Approved
0.7075	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5241	Discontinued
0.7075	Intermediate Similarity	NPD3692	Discontinued
0.7073	Intermediate Similarity	NPD6618	Phase 2
0.7073	Intermediate Similarity	NPD6853	Approved
0.7073	Intermediate Similarity	NPD6851	Approved
0.7071	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7294	Phase 1
0.707	Intermediate Similarity	NPD7802	Discontinued
0.7055	Intermediate Similarity	NPD44	Approved
0.7055	Intermediate Similarity	NPD6364	Approved
0.7045	Intermediate Similarity	NPD317	Approved
0.7045	Intermediate Similarity	NPD318	Approved
0.7045	Intermediate Similarity	NPD2485	Approved
0.7045	Intermediate Similarity	NPD2484	Approved
0.7029	Intermediate Similarity	NPD558	Phase 2
0.7027	Intermediate Similarity	NPD3122	Phase 3
0.7025	Intermediate Similarity	NPD6071	Discontinued
0.7021	Intermediate Similarity	NPD840	Approved
0.7021	Intermediate Similarity	NPD839	Approved
0.7021	Intermediate Similarity	NPD1423	Approved
0.7015	Intermediate Similarity	NPD1751	Approved
0.7015	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2661	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4108	Discontinued
0.7007	Intermediate Similarity	NPD5310	Approved
0.7007	Intermediate Similarity	NPD196	Phase 1
0.7007	Intermediate Similarity	NPD5311	Approved
0.7	Intermediate Similarity	NPD3179	Approved
0.7	Intermediate Similarity	NPD3180	Approved
0.7	Intermediate Similarity	NPD6179	Discontinued
0.6992	Remote Similarity	NPD6580	Approved
0.6992	Remote Similarity	NPD6581	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