NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	193.11
Volume:	202.367
LogP:	1.198
LogD:	1.102
LogS:	-0.396
# 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:	0.769
Synthetic Accessibility Score:	2.038
Fsp3:	0.455
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:	-4.569
MDCK Permeability:	2.398643846390769e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.945
Plasma Protein Binding (PPB):	14.808786392211914%
Volume Distribution (VD):	2.721
Pgp-substrate:	59.17015838623047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.777
CYP1A2-substrate:	0.769
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.548
CYP2D6-inhibitor:	0.891
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.517

ADMET: Excretion

Clearance (CL):	7.572
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.619
Drug-inuced Liver Injury (DILI):	0.654
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.52
Maximum Recommended Daily Dose:	0.755
Skin Sensitization:	0.631
Carcinogencity:	0.052
Eye Corrosion:	0.035
Eye Irritation:	0.032
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC160692

Natural Product ID:	NPC160692
*Common Name:**	6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline
IUPAC Name:	6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
Synonyms:
Standard InCHIKey:	CEIXWJHURKEBMQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H15NO2/c1-13-10-5-8-3-4-12-7-9(8)6-11(10)14-2/h5-6,12H,3-4,7H2,1-2H3
SMILES:	COc1cc2CNCCc2cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL12367
PubChem CID:	15623
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
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]
NPO4880	Artemisia ifranensis	Species	Asteraceae	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	1

Activity Type	# Activity
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	Ki	>	100000.0	nM	PMID[523100]

☑ 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 NPC160692 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	262
0.1-0.2	2423
0.2-0.3	12495
0.3-0.4	5013
0.4-0.5	10117
0.5-0.6	9306
0.6-0.7	2304
0.7-0.8	621
0.8-0.85	121
0.85-0.9	29
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.969	High Similarity	NPC253429
0.9449	High Similarity	NPC160193
0.9259	High Similarity	NPC294249
0.9127	High Similarity	NPC217277
0.9023	High Similarity	NPC7018
0.9023	High Similarity	NPC131204
0.9023	High Similarity	NPC301050
0.8929	High Similarity	NPC60538
0.8929	High Similarity	NPC207824
0.8898	High Similarity	NPC298486
0.8824	High Similarity	NPC314682
0.8803	High Similarity	NPC76213
0.8803	High Similarity	NPC277669
0.8759	High Similarity	NPC328750
0.8759	High Similarity	NPC474915
0.8759	High Similarity	NPC213206
0.8759	High Similarity	NPC188163
0.8702	High Similarity	NPC172403
0.8681	High Similarity	NPC2295
0.8681	High Similarity	NPC477564
0.8633	High Similarity	NPC476567
0.8633	High Similarity	NPC128019
0.8633	High Similarity	NPC136860
0.8621	High Similarity	NPC80129
0.8621	High Similarity	NPC187022
0.8571	High Similarity	NPC120075
0.8562	High Similarity	NPC170503
0.8562	High Similarity	NPC126519
0.8562	High Similarity	NPC203784
0.8511	High Similarity	NPC130926
0.8511	High Similarity	NPC185838
0.8444	Intermediate Similarity	NPC33338
0.8444	Intermediate Similarity	NPC302171
0.8444	Intermediate Similarity	NPC300020
0.8433	Intermediate Similarity	NPC262641
0.8392	Intermediate Similarity	NPC321505
0.8392	Intermediate Similarity	NPC16107
0.8392	Intermediate Similarity	NPC210437
0.8392	Intermediate Similarity	NPC106295
0.8392	Intermediate Similarity	NPC51957
0.8392	Intermediate Similarity	NPC179825
0.8392	Intermediate Similarity	NPC476144
0.8392	Intermediate Similarity	NPC476151
0.8392	Intermediate Similarity	NPC191376
0.8333	Intermediate Similarity	NPC24233
0.8333	Intermediate Similarity	NPC475959
0.8333	Intermediate Similarity	NPC7467
0.8333	Intermediate Similarity	NPC37144
0.8333	Intermediate Similarity	NPC476571
0.8333	Intermediate Similarity	NPC135538
0.8333	Intermediate Similarity	NPC428
0.8333	Intermediate Similarity	NPC147390
0.8333	Intermediate Similarity	NPC246587
0.8333	Intermediate Similarity	NPC59907
0.8278	Intermediate Similarity	NPC475393
0.8276	Intermediate Similarity	NPC103379
0.8276	Intermediate Similarity	NPC477565
0.8235	Intermediate Similarity	NPC476570
0.8227	Intermediate Similarity	NPC323204
0.8224	Intermediate Similarity	NPC2770
0.8224	Intermediate Similarity	NPC39103
0.8224	Intermediate Similarity	NPC284183
0.8224	Intermediate Similarity	NPC121275
0.8224	Intermediate Similarity	NPC4138
0.8219	Intermediate Similarity	NPC192768
0.8219	Intermediate Similarity	NPC151895
0.8219	Intermediate Similarity	NPC274026
0.8219	Intermediate Similarity	NPC220858
0.8219	Intermediate Similarity	NPC97221
0.8219	Intermediate Similarity	NPC88249
0.8201	Intermediate Similarity	NPC416184
0.817	Intermediate Similarity	NPC476573
0.817	Intermediate Similarity	NPC86144
0.817	Intermediate Similarity	NPC81247
0.817	Intermediate Similarity	NPC35627
0.817	Intermediate Similarity	NPC304659
0.8163	Intermediate Similarity	NPC476579
0.8163	Intermediate Similarity	NPC81733
0.8163	Intermediate Similarity	NPC476568
0.8163	Intermediate Similarity	NPC119669
0.8163	Intermediate Similarity	NPC326316
0.8158	Intermediate Similarity	NPC189470
0.8151	Intermediate Similarity	NPC92541
0.8151	Intermediate Similarity	NPC219162
0.812	Intermediate Similarity	NPC140359
0.812	Intermediate Similarity	NPC13020
0.8117	Intermediate Similarity	NPC204947
0.8108	Intermediate Similarity	NPC233029
0.8108	Intermediate Similarity	NPC476580
0.8108	Intermediate Similarity	NPC210148
0.8108	Intermediate Similarity	NPC82285
0.8108	Intermediate Similarity	NPC148898
0.8108	Intermediate Similarity	NPC133011
0.8106	Intermediate Similarity	NPC211992
0.8095	Intermediate Similarity	NPC223125
0.8082	Intermediate Similarity	NPC130941
0.806	Intermediate Similarity	NPC105513
0.8039	Intermediate Similarity	NPC293871
0.8039	Intermediate Similarity	NPC124433
0.8014	Intermediate Similarity	NPC95075
0.8014	Intermediate Similarity	NPC144863
0.8014	Intermediate Similarity	NPC90844
0.8014	Intermediate Similarity	NPC253883
0.8013	Intermediate Similarity	NPC69712
0.8013	Intermediate Similarity	NPC6152
0.8013	Intermediate Similarity	NPC477562
0.8013	Intermediate Similarity	NPC109925
0.8013	Intermediate Similarity	NPC26240
0.8	Intermediate Similarity	NPC110416
0.8	Intermediate Similarity	NPC276588
0.8	Intermediate Similarity	NPC2413
0.8	Intermediate Similarity	NPC249797
0.8	Intermediate Similarity	NPC127674
0.8	Intermediate Similarity	NPC216459
0.8	Intermediate Similarity	NPC469817
0.8	Intermediate Similarity	NPC325871
0.8	Intermediate Similarity	NPC193949
0.8	Intermediate Similarity	NPC39701
0.8	Intermediate Similarity	NPC99659
0.8	Intermediate Similarity	NPC172765
0.8	Intermediate Similarity	NPC5238
0.8	Intermediate Similarity	NPC78733
0.8	Intermediate Similarity	NPC278799
0.8	Intermediate Similarity	NPC138487
0.8	Intermediate Similarity	NPC41178
0.8	Intermediate Similarity	NPC204828
0.8	Intermediate Similarity	NPC295691
0.8	Intermediate Similarity	NPC54379
0.8	Intermediate Similarity	NPC207757
0.8	Intermediate Similarity	NPC189266
0.8	Intermediate Similarity	NPC93593
0.8	Intermediate Similarity	NPC184026
0.7987	Intermediate Similarity	NPC223124
0.7962	Intermediate Similarity	NPC475215
0.7962	Intermediate Similarity	NPC108434
0.7958	Intermediate Similarity	NPC219233
0.7958	Intermediate Similarity	NPC170170
0.7958	Intermediate Similarity	NPC211468
0.7947	Intermediate Similarity	NPC57512
0.7947	Intermediate Similarity	NPC146288
0.7947	Intermediate Similarity	NPC247639
0.7947	Intermediate Similarity	NPC147091
0.7947	Intermediate Similarity	NPC25084
0.7911	Intermediate Similarity	NPC4669
0.7911	Intermediate Similarity	NPC66341
0.7911	Intermediate Similarity	NPC477020
0.7911	Intermediate Similarity	NPC192135
0.7902	Intermediate Similarity	NPC323123
0.7898	Intermediate Similarity	NPC152212
0.7895	Intermediate Similarity	NPC476572
0.7883	Intermediate Similarity	NPC291847
0.7877	Intermediate Similarity	NPC110337
0.7872	Intermediate Similarity	NPC11147
0.7868	Intermediate Similarity	NPC318965
0.7867	Intermediate Similarity	NPC114124
0.7867	Intermediate Similarity	NPC37272
0.7867	Intermediate Similarity	NPC470924
0.7852	Intermediate Similarity	NPC13397
0.7843	Intermediate Similarity	NPC59028
0.7843	Intermediate Similarity	NPC216816
0.7843	Intermediate Similarity	NPC92191
0.7843	Intermediate Similarity	NPC477080
0.7843	Intermediate Similarity	NPC106786
0.7843	Intermediate Similarity	NPC118804
0.7843	Intermediate Similarity	NPC111485
0.7829	Intermediate Similarity	NPC160931
0.7829	Intermediate Similarity	NPC31311
0.7829	Intermediate Similarity	NPC234392
0.7829	Intermediate Similarity	NPC37205
0.7817	Intermediate Similarity	NPC231884
0.7817	Intermediate Similarity	NPC42793
0.7817	Intermediate Similarity	NPC167944
0.7792	Intermediate Similarity	NPC205167
0.7792	Intermediate Similarity	NPC27410
0.7792	Intermediate Similarity	NPC477559
0.7792	Intermediate Similarity	NPC232924
0.7792	Intermediate Similarity	NPC266753
0.7792	Intermediate Similarity	NPC166014
0.7792	Intermediate Similarity	NPC249274
0.7792	Intermediate Similarity	NPC306902
0.7792	Intermediate Similarity	NPC160298
0.7792	Intermediate Similarity	NPC135006
0.7786	Intermediate Similarity	NPC93882
0.7786	Intermediate Similarity	NPC130595
0.7786	Intermediate Similarity	NPC118419
0.7763	Intermediate Similarity	NPC244112
0.775	Intermediate Similarity	NPC477558
0.7748	Intermediate Similarity	NPC26601
0.7742	Intermediate Similarity	NPC60186
0.7742	Intermediate Similarity	NPC24954
0.773	Intermediate Similarity	NPC6854
0.773	Intermediate Similarity	NPC285078
0.773	Intermediate Similarity	NPC313737
0.7724	Intermediate Similarity	NPC470925
0.7716	Intermediate Similarity	NPC267408
0.7716	Intermediate Similarity	NPC475479
0.7716	Intermediate Similarity	NPC470879
0.7716	Intermediate Similarity	NPC243454
0.7716	Intermediate Similarity	NPC258695
0.7716	Intermediate Similarity	NPC474507

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 NPC160692 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	791
0.2-0.3	1166
0.3-0.4	1934
0.4-0.5	2779
0.5-0.6	1510
0.6-0.7	597
0.7-0.8	186
0.8-0.85	13
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD6031	Approved
0.8929	High Similarity	NPD6030	Approved
0.8759	High Similarity	NPD4664	Clinical (unspecified phase)
0.8621	High Similarity	NPD7298	Approved
0.8521	High Similarity	NPD1424	Approved
0.8392	Intermediate Similarity	NPD4584	Approved
0.8309	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD3640	Phase 3
0.8276	Intermediate Similarity	NPD3641	Approved
0.8276	Intermediate Similarity	NPD3639	Approved
0.8235	Intermediate Similarity	NPD5718	Phase 2
0.8163	Intermediate Similarity	NPD4017	Approved
0.8105	Intermediate Similarity	NPD6107	Approved
0.8088	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD4773	Phase 2
0.8054	Intermediate Similarity	NPD4772	Phase 2
0.8052	Intermediate Similarity	NPD4166	Phase 2
0.8042	Intermediate Similarity	NPD3060	Approved
0.8042	Intermediate Similarity	NPD4162	Approved
0.8	Intermediate Similarity	NPD2653	Approved
0.7958	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD7153	Discontinued
0.7838	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6896	Approved
0.7817	Intermediate Similarity	NPD6895	Approved
0.7812	Intermediate Similarity	NPD6297	Approved
0.7786	Intermediate Similarity	NPD2674	Phase 3
0.7786	Intermediate Similarity	NPD3530	Approved
0.7786	Intermediate Similarity	NPD3532	Approved
0.7786	Intermediate Similarity	NPD3531	Approved
0.7763	Intermediate Similarity	NPD5720	Discontinued
0.7714	Intermediate Similarity	NPD1336	Approved
0.7692	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD5241	Discontinued
0.7667	Intermediate Similarity	NPD5976	Discontinued
0.7662	Intermediate Similarity	NPD2563	Approved
0.7662	Intermediate Similarity	NPD2560	Approved
0.7643	Intermediate Similarity	NPD7802	Discontinued
0.7635	Intermediate Similarity	NPD3845	Phase 1
0.7635	Intermediate Similarity	NPD2120	Phase 2
0.7634	Intermediate Similarity	NPD593	Approved
0.7634	Intermediate Similarity	NPD595	Approved
0.7622	Intermediate Similarity	NPD6853	Approved
0.7622	Intermediate Similarity	NPD2986	Phase 2
0.7622	Intermediate Similarity	NPD2989	Phase 2
0.7622	Intermediate Similarity	NPD6851	Approved
0.7622	Intermediate Similarity	NPD6618	Phase 2
0.7619	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4010	Discontinued
0.7595	Intermediate Similarity	NPD6071	Discontinued
0.7589	Intermediate Similarity	NPD3145	Approved
0.7589	Intermediate Similarity	NPD3144	Approved
0.7586	Intermediate Similarity	NPD3156	Discontinued
0.7584	Intermediate Similarity	NPD3124	Discontinued
0.7568	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7833	Phase 2
0.7564	Intermediate Similarity	NPD7831	Phase 2
0.7548	Intermediate Similarity	NPD5977	Approved
0.7548	Intermediate Similarity	NPD5978	Approved
0.7533	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6788	Approved
0.75	Intermediate Similarity	NPD2898	Approved
0.7484	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4585	Approved
0.7482	Intermediate Similarity	NPD3055	Approved
0.7482	Intermediate Similarity	NPD3053	Approved
0.7468	Intermediate Similarity	NPD7110	Phase 1
0.7468	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1039	Discontinued
0.745	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6687	Approved
0.7438	Intermediate Similarity	NPD4083	Discontinued
0.7438	Intermediate Similarity	NPD6688	Approved
0.7434	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1341	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2245	Discovery
0.741	Intermediate Similarity	NPD5310	Approved
0.741	Intermediate Similarity	NPD5311	Approved
0.7407	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8252	Approved
0.7407	Intermediate Similarity	NPD8099	Discontinued
0.7407	Intermediate Similarity	NPD8251	Approved
0.7403	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7124	Phase 2
0.7386	Intermediate Similarity	NPD3687	Approved
0.7386	Intermediate Similarity	NPD3686	Approved
0.7379	Intermediate Similarity	NPD2492	Phase 1
0.7372	Intermediate Similarity	NPD2978	Approved
0.7372	Intermediate Similarity	NPD2977	Approved
0.7365	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD8156	Discontinued
0.7362	Intermediate Similarity	NPD5313	Approved
0.7362	Intermediate Similarity	NPD5312	Approved
0.7361	Intermediate Similarity	NPD3110	Approved
0.7361	Intermediate Similarity	NPD3109	Approved
0.7351	Intermediate Similarity	NPD7598	Phase 2
0.7342	Intermediate Similarity	NPD1309	Phase 2
0.7342	Intermediate Similarity	NPD1307	Phase 2
0.7338	Intermediate Similarity	NPD1420	Approved
0.7338	Intermediate Similarity	NPD1669	Approved
0.7338	Intermediate Similarity	NPD1421	Approved
0.7333	Intermediate Similarity	NPD5160	Discontinued
0.7329	Intermediate Similarity	NPD6111	Discontinued
0.732	Intermediate Similarity	NPD4727	Phase 1
0.7315	Intermediate Similarity	NPD2459	Approved
0.7315	Intermediate Similarity	NPD2458	Approved
0.7315	Intermediate Similarity	NPD2460	Phase 3
0.7315	Intermediate Similarity	NPD5177	Phase 3
0.7305	Intermediate Similarity	NPD9619	Approved
0.7305	Intermediate Similarity	NPD7905	Discontinued
0.7305	Intermediate Similarity	NPD9621	Approved
0.7305	Intermediate Similarity	NPD9620	Approved
0.7299	Intermediate Similarity	NPD2667	Approved
0.7299	Intermediate Similarity	NPD2668	Approved
0.7293	Intermediate Similarity	NPD5283	Phase 1
0.7292	Intermediate Similarity	NPD4474	Approved
0.7292	Intermediate Similarity	NPD4475	Approved
0.729	Intermediate Similarity	NPD6876	Approved
0.729	Intermediate Similarity	NPD6875	Approved
0.7286	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2154	Approved
0.7279	Intermediate Similarity	NPD2155	Approved
0.7279	Intermediate Similarity	NPD2156	Approved
0.7267	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD823	Approved
0.726	Intermediate Similarity	NPD817	Approved
0.7255	Intermediate Similarity	NPD1349	Approved
0.7255	Intermediate Similarity	NPD1350	Approved
0.7255	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1351	Approved
0.7248	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1818	Approved
0.7234	Intermediate Similarity	NPD1817	Approved
0.7234	Intermediate Similarity	NPD1820	Approved
0.7234	Intermediate Similarity	NPD1819	Approved
0.723	Intermediate Similarity	NPD2161	Phase 2
0.7226	Intermediate Similarity	NPD3049	Approved
0.7226	Intermediate Similarity	NPD824	Approved
0.7222	Intermediate Similarity	NPD601	Approved
0.7222	Intermediate Similarity	NPD597	Approved
0.7222	Intermediate Similarity	NPD598	Approved
0.7219	Intermediate Similarity	NPD2677	Approved
0.7218	Intermediate Similarity	NPD9377	Approved
0.7218	Intermediate Similarity	NPD9379	Approved
0.7214	Intermediate Similarity	NPD2429	Approved
0.7214	Intermediate Similarity	NPD2428	Approved
0.7206	Intermediate Similarity	NPD1102	Approved
0.7206	Intermediate Similarity	NPD1103	Approved
0.7197	Intermediate Similarity	NPD1769	Discontinued
0.7181	Intermediate Similarity	NPD3656	Approved
0.7174	Intermediate Similarity	NPD2556	Approved
0.7174	Intermediate Similarity	NPD2554	Approved
0.7172	Intermediate Similarity	NPD1130	Approved
0.7172	Intermediate Similarity	NPD1136	Approved
0.7172	Intermediate Similarity	NPD1132	Approved
0.7163	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2883	Discontinued
0.716	Intermediate Similarity	NPD3051	Approved
0.7153	Intermediate Similarity	NPD316	Approved
0.7143	Intermediate Similarity	NPD2232	Approved
0.7143	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2233	Approved
0.7143	Intermediate Similarity	NPD228	Approved
0.7143	Intermediate Similarity	NPD2230	Approved
0.7143	Intermediate Similarity	NPD5677	Discontinued
0.7124	Intermediate Similarity	NPD1774	Approved
0.7123	Intermediate Similarity	NPD3059	Approved
0.7123	Intermediate Similarity	NPD3061	Approved
0.7123	Intermediate Similarity	NPD3062	Approved
0.7122	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2969	Approved
0.7117	Intermediate Similarity	NPD2970	Approved
0.7113	Intermediate Similarity	NPD4098	Discontinued
0.7101	Intermediate Similarity	NPD2594	Approved
0.7101	Intermediate Similarity	NPD8053	Approved
0.7101	Intermediate Similarity	NPD8054	Approved
0.7101	Intermediate Similarity	NPD2595	Approved
0.7086	Intermediate Similarity	NPD4236	Phase 3
0.7086	Intermediate Similarity	NPD4237	Approved
0.708	Intermediate Similarity	NPD9616	Approved
0.708	Intermediate Similarity	NPD9613	Approved
0.708	Intermediate Similarity	NPD9615	Approved
0.7078	Intermediate Similarity	NPD2874	Phase 2
0.7078	Intermediate Similarity	NPD4123	Phase 3
0.7073	Intermediate Similarity	NPD27	Approved
0.7073	Intermediate Similarity	NPD4481	Phase 3
0.7073	Intermediate Similarity	NPD2489	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