NPASS Compound

Structure

NPC475959 OpenBabel07101719242D 26 29 0 0 1 0 0 0 0 0999 V2000 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 6 1 0 0 0 0 4 14 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 22 1 0 0 0 0 10 14 2 0 0 0 0 10 21 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 25 1 0 0 0 0 13 26 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 6 1 6 0 0 0 17 22 1 0 0 0 0 18 21 2 0 0 0 0 18 25 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.18
Volume:	367.885
LogP:	3.459
LogD:	3.075
LogS:	-3.752
# Rotatable Bonds:	5
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.82
Synthetic Accessibility Score:	2.774
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.941
MDCK Permeability:	3.4434819099260494e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.619

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973
Plasma Protein Binding (PPB):	93.71671295166016%
Volume Distribution (VD):	2.378
Pgp-substrate:	2.6481707096099854%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.673
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.978
CYP2D6-substrate:	0.956
CYP3A4-inhibitor:	0.956
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	13.559
Half-life (T1/2):	0.585

ADMET: Toxicity

hERG Blockers:	0.876
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.613
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.384
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.366
Carcinogencity:	0.736
Eye Corrosion:	0.003
Eye Irritation:	0.011
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: NPC475959

Natural Product ID:	NPC475959
*Common Name:**	Dysoxyline
IUPAC Name:	(1R)-1-[2-(1,3-benzodioxol-5-yl)ethyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
Synonyms:	Dysoxyline
Standard InCHIKey:	AGCGPVWWLORMQV-QGZVFWFLSA-N
Standard InCHI:	InChI=1S/C21H25NO4/c1-22-9-8-15-11-19(23-2)20(24-3)12-16(15)17(22)6-4-14-5-7-18-21(10-14)26-13-25-18/h5,7,10-12,17H,4,6,8-9,13H2,1-3H3/t17-/m1/s1
SMILES:	CN1CCC2=CC(=C(C=C2C1CCC3=CC4=C(C=C3)OCO4)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519734
PubChem CID:	44559821
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
NPO18479	Dysoxylum lenticellare	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[3443856]
NPO18479	Dysoxylum lenticellare	Species	Meliaceae	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT610	Others	Molecular identity unknown		Activity	=	-6.4	%	PMID[492378]
NPT610	Others	Molecular identity unknown		Activity	=	11.8	%	PMID[492378]

☑ 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 NPC475959 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	296
0.1-0.2	1521
0.2-0.3	8442
0.3-0.4	9538
0.4-0.5	7360
0.5-0.6	11426
0.6-0.7	3095
0.7-0.8	641
0.8-0.85	223
0.85-0.9	109
0.9-0.95	40
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9586	High Similarity	NPC41178
0.9586	High Similarity	NPC216459
0.9586	High Similarity	NPC138487
0.9583	High Similarity	NPC210148
0.9583	High Similarity	NPC233029
0.9521	High Similarity	NPC146288
0.9496	High Similarity	NPC474915
0.9496	High Similarity	NPC213206
0.9496	High Similarity	NPC328750
0.9496	High Similarity	NPC188163
0.9424	High Similarity	NPC314682
0.9388	High Similarity	NPC234392
0.9388	High Similarity	NPC31311
0.9262	High Similarity	NPC111485
0.9225	High Similarity	NPC136860
0.9225	High Similarity	NPC128019
0.9225	High Similarity	NPC476567
0.9209	High Similarity	NPC7018
0.92	High Similarity	NPC306902
0.92	High Similarity	NPC232924
0.92	High Similarity	NPC266753
0.92	High Similarity	NPC160298
0.92	High Similarity	NPC477559
0.9189	High Similarity	NPC78733
0.9189	High Similarity	NPC93593
0.9184	High Similarity	NPC148898
0.9145	High Similarity	NPC238530
0.9145	High Similarity	NPC232514
0.9145	High Similarity	NPC276944
0.9133	High Similarity	NPC477080
0.9103	High Similarity	NPC16107
0.9103	High Similarity	NPC210437
0.9103	High Similarity	NPC51957
0.9103	High Similarity	NPC106295
0.9103	High Similarity	NPC476144
0.9097	High Similarity	NPC185838
0.9085	High Similarity	NPC476432
0.9085	High Similarity	NPC24264
0.9041	High Similarity	NPC246587
0.9041	High Similarity	NPC7467
0.9041	High Similarity	NPC135538
0.9041	High Similarity	NPC428
0.9041	High Similarity	NPC476571
0.9041	High Similarity	NPC24233
0.9041	High Similarity	NPC147390
0.9026	High Similarity	NPC247389
0.902	High Similarity	NPC167546
0.902	High Similarity	NPC225774
0.902	High Similarity	NPC302527
0.902	High Similarity	NPC16805
0.8973	High Similarity	NPC321505
0.8973	High Similarity	NPC179825
0.8973	High Similarity	NPC191376
0.8961	High Similarity	NPC219341
0.8933	High Similarity	NPC76079
0.8919	High Similarity	NPC223125
0.8903	High Similarity	NPC298979
0.8903	High Similarity	NPC210918
0.8882	High Similarity	NPC106786
0.8851	High Similarity	NPC219162
0.8846	High Similarity	NPC241055
0.8844	High Similarity	NPC476151
0.8839	High Similarity	NPC304659
0.8839	High Similarity	NPC86144
0.8836	High Similarity	NPC130926
0.8831	High Similarity	NPC59567
0.8824	High Similarity	NPC97072
0.8824	High Similarity	NPC215829
0.88	High Similarity	NPC223124
0.8797	High Similarity	NPC2314
0.8792	High Similarity	NPC151895
0.8792	High Similarity	NPC97221
0.8792	High Similarity	NPC88249
0.8792	High Similarity	NPC192768
0.8792	High Similarity	NPC220858
0.8784	High Similarity	NPC130941
0.8777	High Similarity	NPC160193
0.8774	High Similarity	NPC168409
0.8774	High Similarity	NPC231198
0.8766	High Similarity	NPC24954
0.8734	High Similarity	NPC19520
0.8734	High Similarity	NPC149090
0.8733	High Similarity	NPC81733
0.8733	High Similarity	NPC326316
0.8733	High Similarity	NPC476568
0.8732	High Similarity	NPC11147
0.8726	High Similarity	NPC158148
0.8726	High Similarity	NPC82533
0.8726	High Similarity	NPC266176
0.8726	High Similarity	NPC290759
0.8725	High Similarity	NPC207824
0.8725	High Similarity	NPC477565
0.8725	High Similarity	NPC60538
0.8725	High Similarity	NPC103379
0.8716	High Similarity	NPC95075
0.8716	High Similarity	NPC90844
0.8716	High Similarity	NPC253883
0.871	High Similarity	NPC189470
0.8684	High Similarity	NPC204828
0.8684	High Similarity	NPC172765
0.8684	High Similarity	NPC127674
0.8684	High Similarity	NPC184026
0.8684	High Similarity	NPC39701
0.8684	High Similarity	NPC469817
0.8684	High Similarity	NPC189266
0.8684	High Similarity	NPC276588
0.8684	High Similarity	NPC2413
0.8684	High Similarity	NPC249797
0.8684	High Similarity	NPC193949
0.8684	High Similarity	NPC207757
0.8684	High Similarity	NPC295691
0.8684	High Similarity	NPC278799
0.8684	High Similarity	NPC110416
0.8684	High Similarity	NPC54379
0.8684	High Similarity	NPC5238
0.8671	High Similarity	NPC75958
0.8671	High Similarity	NPC6152
0.8662	High Similarity	NPC100566
0.8662	High Similarity	NPC474324
0.8662	High Similarity	NPC57812
0.8634	High Similarity	NPC320223
0.8634	High Similarity	NPC118633
0.8634	High Similarity	NPC148693
0.8634	High Similarity	NPC294790
0.8634	High Similarity	NPC114364
0.8633	High Similarity	NPC172403
0.8627	High Similarity	NPC25084
0.8627	High Similarity	NPC247639
0.8625	High Similarity	NPC199465
0.8625	High Similarity	NPC229166
0.8625	High Similarity	NPC128560
0.8616	High Similarity	NPC470739
0.8616	High Similarity	NPC225597
0.8616	High Similarity	NPC477640
0.8616	High Similarity	NPC65403
0.8611	High Similarity	NPC253429
0.8609	High Similarity	NPC277669
0.8609	High Similarity	NPC76213
0.8608	High Similarity	NPC58766
0.8608	High Similarity	NPC475845
0.8608	High Similarity	NPC475686
0.86	High Similarity	NPC92541
0.859	High Similarity	NPC320104
0.8581	High Similarity	NPC145304
0.858	High Similarity	NPC27887
0.8571	High Similarity	NPC476572
0.8571	High Similarity	NPC287588
0.8562	High Similarity	NPC325871
0.8562	High Similarity	NPC244112
0.8562	High Similarity	NPC99659
0.8562	High Similarity	NPC80129
0.8562	High Similarity	NPC187022
0.8553	High Similarity	NPC311991
0.8553	High Similarity	NPC474475
0.8553	High Similarity	NPC474708
0.8544	High Similarity	NPC190332
0.8544	High Similarity	NPC181653
0.8543	High Similarity	NPC274026
0.8542	High Similarity	NPC416184
0.8535	High Similarity	NPC247972
0.8533	High Similarity	NPC37144
0.8533	High Similarity	NPC59907
0.8521	High Similarity	NPC118419
0.8509	High Similarity	NPC187678
0.8506	High Similarity	NPC147091
0.8487	Intermediate Similarity	NPC476579
0.8477	Intermediate Similarity	NPC211296
0.8476	Intermediate Similarity	NPC299990
0.8476	Intermediate Similarity	NPC248642
0.8476	Intermediate Similarity	NPC73492
0.8471	Intermediate Similarity	NPC233650
0.8467	Intermediate Similarity	NPC144863
0.8466	Intermediate Similarity	NPC126284
0.8457	Intermediate Similarity	NPC474470
0.8438	Intermediate Similarity	NPC152212
0.8431	Intermediate Similarity	NPC133011
0.8431	Intermediate Similarity	NPC82285
0.8431	Intermediate Similarity	NPC26601
0.8424	Intermediate Similarity	NPC156576
0.8418	Intermediate Similarity	NPC134858
0.8415	Intermediate Similarity	NPC474506
0.8415	Intermediate Similarity	NPC179704
0.8415	Intermediate Similarity	NPC32413
0.8405	Intermediate Similarity	NPC23219
0.8397	Intermediate Similarity	NPC216816
0.8395	Intermediate Similarity	NPC304675
0.8387	Intermediate Similarity	NPC203784
0.8387	Intermediate Similarity	NPC186063
0.8387	Intermediate Similarity	NPC170503
0.8387	Intermediate Similarity	NPC126519
0.8377	Intermediate Similarity	NPC477564
0.8377	Intermediate Similarity	NPC2295
0.8364	Intermediate Similarity	NPC116284
0.8354	Intermediate Similarity	NPC470879
0.8354	Intermediate Similarity	NPC244554
0.8354	Intermediate Similarity	NPC267408
0.8354	Intermediate Similarity	NPC258695
0.8354	Intermediate Similarity	NPC475393
0.8344	Intermediate Similarity	NPC112575
0.8344	Intermediate Similarity	NPC237044

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 NPC475959 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	743
0.2-0.3	1027
0.3-0.4	1743
0.4-0.5	2780
0.5-0.6	1828
0.6-0.7	652
0.7-0.8	158
0.8-0.85	24
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9496	High Similarity	NPD4664	Clinical (unspecified phase)
0.9103	High Similarity	NPD4584	Approved
0.8733	High Similarity	NPD4017	Approved
0.8639	High Similarity	NPD5084	Clinical (unspecified phase)
0.8581	High Similarity	NPD6783	Clinical (unspecified phase)
0.8562	High Similarity	NPD7298	Approved
0.8477	Intermediate Similarity	NPD3639	Approved
0.8477	Intermediate Similarity	NPD6031	Approved
0.8477	Intermediate Similarity	NPD3641	Approved
0.8477	Intermediate Similarity	NPD6030	Approved
0.8477	Intermediate Similarity	NPD3640	Phase 3
0.838	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD5718	Phase 2
0.8264	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD4773	Phase 2
0.8258	Intermediate Similarity	NPD4772	Phase 2
0.8239	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD5241	Discontinued
0.8137	Intermediate Similarity	NPD4010	Discontinued
0.8108	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6107	Approved
0.8056	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD8099	Discontinued
0.8049	Intermediate Similarity	NPD8251	Approved
0.8049	Intermediate Similarity	NPD8252	Approved
0.8041	Intermediate Similarity	NPD6896	Approved
0.8041	Intermediate Similarity	NPD6895	Approved
0.8025	Intermediate Similarity	NPD4166	Phase 2
0.8	Intermediate Similarity	NPD8156	Discontinued
0.7976	Intermediate Similarity	NPD7280	Phase 3
0.7976	Intermediate Similarity	NPD7281	Phase 3
0.7973	Intermediate Similarity	NPD2492	Phase 1
0.7963	Intermediate Similarity	NPD7802	Discontinued
0.7943	Intermediate Similarity	NPD4420	Approved
0.7937	Intermediate Similarity	NPD6788	Approved
0.7927	Intermediate Similarity	NPD4481	Phase 3
0.7927	Intermediate Similarity	NPD2898	Approved
0.7925	Intermediate Similarity	NPD2978	Approved
0.7925	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD2977	Approved
0.7922	Intermediate Similarity	NPD3124	Discontinued
0.7904	Intermediate Similarity	NPD6297	Approved
0.7888	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7833	Phase 2
0.7888	Intermediate Similarity	NPD7831	Phase 2
0.7875	Intermediate Similarity	NPD5978	Approved
0.7875	Intermediate Similarity	NPD5977	Approved
0.7805	Intermediate Similarity	NPD3051	Approved
0.7805	Intermediate Similarity	NPD6071	Discontinued
0.7792	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5313	Approved
0.7784	Intermediate Similarity	NPD5312	Approved
0.7778	Intermediate Similarity	NPD5604	Discontinued
0.7771	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5006	Approved
0.7765	Intermediate Similarity	NPD5005	Approved
0.7764	Intermediate Similarity	NPD2560	Approved
0.7764	Intermediate Similarity	NPD2563	Approved
0.7758	Intermediate Similarity	NPD2970	Approved
0.7758	Intermediate Similarity	NPD2969	Approved
0.7719	Intermediate Similarity	NPD8054	Approved
0.7719	Intermediate Similarity	NPD8053	Approved
0.7719	Intermediate Similarity	NPD6851	Approved
0.7719	Intermediate Similarity	NPD6853	Approved
0.7718	Intermediate Similarity	NPD3109	Approved
0.7718	Intermediate Similarity	NPD3110	Approved
0.7711	Intermediate Similarity	NPD2489	Approved
0.7711	Intermediate Similarity	NPD27	Approved
0.7688	Intermediate Similarity	NPD7110	Phase 1
0.7688	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4727	Phase 1
0.7651	Intermediate Similarity	NPD4474	Approved
0.7651	Intermediate Similarity	NPD4475	Approved
0.7643	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3885	Approved
0.7628	Intermediate Similarity	NPD7124	Phase 2
0.7613	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3349	Phase 2
0.758	Intermediate Similarity	NPD2420	Approved
0.758	Intermediate Similarity	NPD2421	Approved
0.7572	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4237	Approved
0.7548	Intermediate Similarity	NPD4236	Phase 3
0.7548	Intermediate Similarity	NPD5177	Phase 3
0.7547	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6688	Approved
0.7545	Intermediate Similarity	NPD6687	Approved
0.7532	Intermediate Similarity	NPD1424	Approved
0.7531	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4108	Discontinued
0.7516	Intermediate Similarity	NPD3845	Phase 1
0.75	Intermediate Similarity	NPD5754	Discontinued
0.747	Intermediate Similarity	NPD5677	Discontinued
0.7455	Intermediate Similarity	NPD4055	Discovery
0.7448	Intermediate Similarity	NPD3705	Approved
0.7443	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3060	Approved
0.7436	Intermediate Similarity	NPD4162	Approved
0.7432	Intermediate Similarity	NPD7905	Discontinued
0.7432	Intermediate Similarity	NPD7247	Discontinued
0.743	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD5582	Discontinued
0.7429	Intermediate Similarity	NPD5283	Phase 1
0.7417	Intermediate Similarity	NPD2674	Phase 3
0.7415	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6875	Approved
0.7407	Intermediate Similarity	NPD6876	Approved
0.7405	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4210	Discontinued
0.7389	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6748	Discontinued
0.7386	Intermediate Similarity	NPD7291	Discontinued
0.7386	Intermediate Similarity	NPD7906	Approved
0.7386	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4098	Discontinued
0.7356	Intermediate Similarity	NPD2971	Approved
0.7356	Intermediate Similarity	NPD7311	Approved
0.7356	Intermediate Similarity	NPD7313	Approved
0.7356	Intermediate Similarity	NPD7310	Approved
0.7356	Intermediate Similarity	NPD2968	Approved
0.7356	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7312	Approved
0.7355	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1421	Approved
0.7347	Intermediate Similarity	NPD1420	Approved
0.7346	Intermediate Similarity	NPD4005	Discontinued
0.7333	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5976	Discontinued
0.7326	Intermediate Similarity	NPD3920	Phase 2
0.7317	Intermediate Similarity	NPD5720	Discontinued
0.7317	Intermediate Similarity	NPD3383	Approved
0.7317	Intermediate Similarity	NPD3382	Approved
0.7317	Intermediate Similarity	NPD3384	Approved
0.7314	Intermediate Similarity	NPD6618	Phase 2
0.7314	Intermediate Similarity	NPD7309	Approved
0.731	Intermediate Similarity	NPD2668	Approved
0.731	Intermediate Similarity	NPD2667	Approved
0.731	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1375	Discontinued
0.7305	Intermediate Similarity	NPD7400	Phase 3
0.7303	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3816	Phase 1
0.7302	Intermediate Similarity	NPD3815	Phase 1
0.7296	Intermediate Similarity	NPD2120	Phase 2
0.7294	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1753	Discontinued
0.7289	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6331	Phase 2
0.7273	Intermediate Similarity	NPD5772	Approved
0.7273	Intermediate Similarity	NPD2653	Approved
0.7273	Intermediate Similarity	NPD4859	Phase 1
0.7273	Intermediate Similarity	NPD5773	Approved
0.7268	Intermediate Similarity	NPD5457	Discontinued
0.7263	Intermediate Similarity	NPD3922	Approved
0.7263	Intermediate Similarity	NPD3921	Approved
0.7263	Intermediate Similarity	NPD3923	Approved
0.7263	Intermediate Similarity	NPD3924	Approved
0.7258	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4578	Approved
0.7257	Intermediate Similarity	NPD4577	Approved
0.7256	Intermediate Similarity	NPD6386	Approved
0.7256	Intermediate Similarity	NPD6385	Approved
0.725	Intermediate Similarity	NPD7598	Phase 2
0.7237	Intermediate Similarity	NPD5109	Approved
0.7237	Intermediate Similarity	NPD5111	Phase 2
0.7237	Intermediate Similarity	NPD5110	Phase 2
0.7237	Intermediate Similarity	NPD3145	Approved
0.7237	Intermediate Similarity	NPD3144	Approved
0.7237	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4663	Approved
0.723	Intermediate Similarity	NPD1669	Approved
0.7216	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8095	Phase 1
0.7205	Intermediate Similarity	NPD4123	Phase 3
0.7198	Intermediate Similarity	NPD5564	Approved
0.7197	Intermediate Similarity	NPD3656	Approved
0.7195	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3532	Approved
0.719	Intermediate Similarity	NPD3531	Approved
0.719	Intermediate Similarity	NPD3530	Approved
0.7184	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2232	Approved
0.7162	Intermediate Similarity	NPD2230	Approved
0.7162	Intermediate Similarity	NPD2233	Approved
0.7161	Intermediate Similarity	NPD2989	Phase 2
0.7161	Intermediate Similarity	NPD2986	Phase 2
0.7159	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6873	Phase 2
0.7152	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2161	Phase 2
0.7126	Intermediate Similarity	NPD5967	Approved
0.7125	Intermediate Similarity	NPD3692	Discontinued
0.7123	Intermediate Similarity	NPD2595	Approved
0.7123	Intermediate Similarity	NPD2594	Approved
0.7117	Intermediate Similarity	NPD1914	Approved
0.7115	Intermediate Similarity	NPD6111	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data