NPASS Compound

Structure

CID151895 OpenBabel06191715522D 25 28 0 0 1 0 0 0 0 0999 V2000 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 21 1 0 0 0 0 6 13 1 0 0 0 0 6 16 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 15 16 1 0 0 0 0 16 21 1 1 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	341.16
Volume:	350.589
LogP:	2.444
LogD:	3.065
LogS:	-2.315
# Rotatable Bonds:	3
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.93
Synthetic Accessibility Score:	2.821
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.087
MDCK Permeability:	2.331435098312795e-05
Pgp-inhibitor:	0.448
Pgp-substrate:	0.957
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.703
30% Bioavailability (F30%):	0.16

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	74.43293762207031%
Volume Distribution (VD):	1.382
Pgp-substrate:	16.387222290039062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.252
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.165
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.592
CYP2D6-inhibitor:	0.809
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	14.204
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.783
AMES Toxicity:	0.111
Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.573
Carcinogencity:	0.083
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC151895

Natural Product ID:	NPC151895
*Common Name:**	Discretine
IUPAC Name:	(13aS)-2,10,11-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-3-ol
Synonyms:	Discretine
Standard InCHIKey:	FSKPDOZBWMKQBY-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C20H23NO4/c1-23-18-10-15-12(7-17(18)22)4-5-21-11-14-9-20(25-3)19(24-2)8-13(14)6-16(15)21/h7-10,16,22H,4-6,11H2,1-3H3/t16-/m0/s1
SMILES:	COc1cc2c(CCN3Cc4cc(c(cc4C[C@@H]23)OC)OC)cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513084
PubChem CID:	821491
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32522	desmos rostrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053513]
NPO19863	Micromelum ceylanicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20570	Esperiopsis digitata	Species	Esperiopsidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16408	Grevillea hilliana	Species	Proteaceae	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
IC50	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	29000.0	nM	PMID[479718]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1600.0	nM	PMID[479718]

☑ 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 NPC151895 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	271
0.1-0.2	1467
0.2-0.3	7677
0.3-0.4	10438
0.4-0.5	5948
0.5-0.6	11385
0.6-0.7	4163
0.7-0.8	910
0.8-0.85	223
0.85-0.9	120
0.9-0.95	62
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC220858
1.0	High Similarity	NPC88249
1.0	High Similarity	NPC192768
1.0	High Similarity	NPC97221
0.9724	High Similarity	NPC127674
0.9724	High Similarity	NPC5238
0.9724	High Similarity	NPC249797
0.9724	High Similarity	NPC295691
0.9724	High Similarity	NPC469817
0.9724	High Similarity	NPC189266
0.9724	High Similarity	NPC276588
0.9724	High Similarity	NPC184026
0.9724	High Similarity	NPC2413
0.9724	High Similarity	NPC278799
0.9724	High Similarity	NPC193949
0.9724	High Similarity	NPC110416
0.9724	High Similarity	NPC54379
0.9724	High Similarity	NPC204828
0.9724	High Similarity	NPC207757
0.9724	High Similarity	NPC39701
0.9724	High Similarity	NPC172765
0.9718	High Similarity	NPC24233
0.9718	High Similarity	NPC147390
0.9718	High Similarity	NPC135538
0.9718	High Similarity	NPC246587
0.9718	High Similarity	NPC428
0.9718	High Similarity	NPC476571
0.9648	High Similarity	NPC179825
0.9648	High Similarity	NPC191376
0.9648	High Similarity	NPC321505
0.9527	High Similarity	NPC111485
0.9507	High Similarity	NPC185838
0.9504	High Similarity	NPC136860
0.9504	High Similarity	NPC476567
0.9504	High Similarity	NPC128019
0.9379	High Similarity	NPC477565
0.9379	High Similarity	NPC103379
0.932	High Similarity	NPC37272
0.9276	High Similarity	NPC238530
0.9276	High Similarity	NPC24465
0.9276	High Similarity	NPC276944
0.9276	High Similarity	NPC4138
0.9276	High Similarity	NPC232514
0.9276	High Similarity	NPC121275
0.9276	High Similarity	NPC284183
0.9252	High Similarity	NPC277669
0.9252	High Similarity	NPC76213
0.9241	High Similarity	NPC210437
0.9241	High Similarity	NPC16107
0.9241	High Similarity	NPC51957
0.9241	High Similarity	NPC476144
0.9241	High Similarity	NPC476151
0.9241	High Similarity	NPC106295
0.9225	High Similarity	NPC213206
0.9225	High Similarity	NPC328750
0.9225	High Similarity	NPC474915
0.9225	High Similarity	NPC188163
0.9216	High Similarity	NPC264850
0.9216	High Similarity	NPC317272
0.9216	High Similarity	NPC268503
0.9216	High Similarity	NPC250846
0.9216	High Similarity	NPC256012
0.9216	High Similarity	NPC13916
0.9216	High Similarity	NPC42549
0.9216	High Similarity	NPC240841
0.9178	High Similarity	NPC7467
0.9155	High Similarity	NPC314682
0.9116	High Similarity	NPC207824
0.9116	High Similarity	NPC60538
0.9097	High Similarity	NPC66573
0.9085	High Similarity	NPC324144
0.9079	High Similarity	NPC27410
0.9079	High Similarity	NPC166014
0.9078	High Similarity	NPC301050
0.9078	High Similarity	NPC131204
0.9038	High Similarity	NPC109925
0.9026	High Similarity	NPC78222
0.9026	High Similarity	NPC196447
0.9026	High Similarity	NPC306843
0.9026	High Similarity	NPC212794
0.9026	High Similarity	NPC96603
0.9026	High Similarity	NPC13504
0.9026	High Similarity	NPC477563
0.9026	High Similarity	NPC136508
0.9026	High Similarity	NPC253043
0.9007	High Similarity	NPC186063
0.9	High Similarity	NPC477564
0.9	High Similarity	NPC2295
0.8933	High Similarity	NPC133011
0.8933	High Similarity	NPC233029
0.8933	High Similarity	NPC82285
0.8933	High Similarity	NPC210148
0.891	High Similarity	NPC474931
0.891	High Similarity	NPC158376
0.891	High Similarity	NPC117188
0.891	High Similarity	NPC205421
0.891	High Similarity	NPC12053
0.891	High Similarity	NPC145832
0.891	High Similarity	NPC306555
0.891	High Similarity	NPC81218
0.8904	High Similarity	NPC294249
0.8882	High Similarity	NPC147091
0.8861	High Similarity	NPC108434
0.8861	High Similarity	NPC475215
0.8831	High Similarity	NPC205167
0.8816	High Similarity	NPC216459
0.8816	High Similarity	NPC80129
0.8816	High Similarity	NPC138487
0.8816	High Similarity	NPC187022
0.8816	High Similarity	NPC41178
0.8792	High Similarity	NPC475959
0.879	High Similarity	NPC210140
0.8774	High Similarity	NPC60186
0.8758	High Similarity	NPC146288
0.8758	High Similarity	NPC247639
0.8758	High Similarity	NPC25084
0.8742	High Similarity	NPC476568
0.8742	High Similarity	NPC239775
0.8734	High Similarity	NPC204908
0.8734	High Similarity	NPC83198
0.8733	High Similarity	NPC92541
0.8726	High Similarity	NPC35627
0.8726	High Similarity	NPC81247
0.8726	High Similarity	NPC476573
0.8718	High Similarity	NPC1229
0.871	High Similarity	NPC249274
0.8704	High Similarity	NPC32154
0.8684	High Similarity	NPC26601
0.8679	High Similarity	NPC26240
0.8679	High Similarity	NPC69712
0.8679	High Similarity	NPC477562
0.8675	High Similarity	NPC274026
0.8662	High Similarity	NPC134858
0.8652	High Similarity	NPC160193
0.865	High Similarity	NPC286119
0.8645	High Similarity	NPC216816
0.8636	High Similarity	NPC234392
0.8636	High Similarity	NPC31311
0.8634	High Similarity	NPC229166
0.8634	High Similarity	NPC128560
0.8634	High Similarity	NPC199465
0.8618	High Similarity	NPC81733
0.8618	High Similarity	NPC326316
0.8618	High Similarity	NPC476579
0.86	High Similarity	NPC144863
0.8599	High Similarity	NPC233650
0.8598	High Similarity	NPC239824
0.8598	High Similarity	NPC182052
0.8598	High Similarity	NPC7715
0.8598	High Similarity	NPC90998
0.8598	High Similarity	NPC42663
0.8598	High Similarity	NPC290582
0.8598	High Similarity	NPC271013
0.8598	High Similarity	NPC223690
0.8598	High Similarity	NPC279228
0.8598	High Similarity	NPC54654
0.8598	High Similarity	NPC104196
0.8598	High Similarity	NPC8836
0.8598	High Similarity	NPC222661
0.8598	High Similarity	NPC229373
0.8598	High Similarity	NPC251735
0.8598	High Similarity	NPC217748
0.8598	High Similarity	NPC290005
0.8598	High Similarity	NPC258657
0.8598	High Similarity	NPC15414
0.8598	High Similarity	NPC311973
0.8598	High Similarity	NPC30779
0.8598	High Similarity	NPC185639
0.8598	High Similarity	NPC181796
0.8598	High Similarity	NPC49075
0.8598	High Similarity	NPC285931
0.8598	High Similarity	NPC328155
0.859	High Similarity	NPC226428
0.8581	High Similarity	NPC475326
0.858	High Similarity	NPC241704
0.8571	High Similarity	NPC2314
0.8571	High Similarity	NPC99659
0.8571	High Similarity	NPC190783
0.8571	High Similarity	NPC66341
0.8571	High Similarity	NPC232386
0.8571	High Similarity	NPC325871
0.8571	High Similarity	NPC152680
0.8571	High Similarity	NPC477020
0.8571	High Similarity	NPC192135
0.8562	High Similarity	NPC168753
0.8562	High Similarity	NPC118274
0.8553	High Similarity	NPC298979
0.8545	High Similarity	NPC254441
0.8545	High Similarity	NPC274716
0.8545	High Similarity	NPC167116
0.8544	High Similarity	NPC169743
0.8543	High Similarity	NPC130941
0.8528	High Similarity	NPC320223
0.8528	High Similarity	NPC114364
0.8526	High Similarity	NPC477080
0.8503	High Similarity	NPC323123
0.8493	Intermediate Similarity	NPC253429
0.8487	Intermediate Similarity	NPC219162
0.8481	Intermediate Similarity	NPC475393
0.8467	Intermediate Similarity	NPC130926

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 NPC151895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	718
0.2-0.3	1074
0.3-0.4	1791
0.4-0.5	2670
0.5-0.6	1780
0.6-0.7	721
0.7-0.8	187
0.8-0.85	24
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9241	High Similarity	NPD4584	Approved
0.9225	High Similarity	NPD4664	Clinical (unspecified phase)
0.8846	High Similarity	NPD4010	Discontinued
0.8816	High Similarity	NPD7298	Approved
0.875	High Similarity	NPD4772	Phase 2
0.875	High Similarity	NPD4773	Phase 2
0.8609	High Similarity	NPD3641	Approved
0.8609	High Similarity	NPD3639	Approved
0.8609	High Similarity	NPD3640	Phase 3
0.8598	High Similarity	NPD8053	Approved
0.8598	High Similarity	NPD8054	Approved
0.8497	Intermediate Similarity	NPD4017	Approved
0.8481	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD5241	Discontinued
0.8385	Intermediate Similarity	NPD2898	Approved
0.8355	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD2421	Approved
0.8289	Intermediate Similarity	NPD2420	Approved
0.828	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD6031	Approved
0.8247	Intermediate Similarity	NPD6030	Approved
0.8239	Intermediate Similarity	NPD7833	Phase 2
0.8239	Intermediate Similarity	NPD7831	Phase 2
0.8239	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD3845	Phase 1
0.8171	Intermediate Similarity	NPD8252	Approved
0.8171	Intermediate Similarity	NPD8251	Approved
0.8171	Intermediate Similarity	NPD8099	Discontinued
0.816	Intermediate Similarity	NPD27	Approved
0.816	Intermediate Similarity	NPD2489	Approved
0.8138	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD8156	Discontinued
0.8105	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6107	Approved
0.8082	Intermediate Similarity	NPD5718	Phase 2
0.8052	Intermediate Similarity	NPD3124	Discontinued
0.8027	Intermediate Similarity	NPD2674	Phase 3
0.7988	Intermediate Similarity	NPD2970	Approved
0.7988	Intermediate Similarity	NPD2969	Approved
0.7947	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3051	Approved
0.7927	Intermediate Similarity	NPD4166	Phase 2
0.7917	Intermediate Similarity	NPD6297	Approved
0.7892	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7802	Discontinued
0.784	Intermediate Similarity	NPD6788	Approved
0.7838	Intermediate Similarity	NPD3144	Approved
0.7838	Intermediate Similarity	NPD3145	Approved
0.7823	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6071	Discontinued
0.7815	Intermediate Similarity	NPD6896	Approved
0.7815	Intermediate Similarity	NPD6895	Approved
0.7803	Intermediate Similarity	NPD7906	Approved
0.7798	Intermediate Similarity	NPD5313	Approved
0.7798	Intermediate Similarity	NPD5312	Approved
0.7792	Intermediate Similarity	NPD3060	Approved
0.7792	Intermediate Similarity	NPD5177	Phase 3
0.7778	Intermediate Similarity	NPD2560	Approved
0.7778	Intermediate Similarity	NPD7311	Approved
0.7778	Intermediate Similarity	NPD7313	Approved
0.7778	Intermediate Similarity	NPD7310	Approved
0.7778	Intermediate Similarity	NPD7312	Approved
0.7778	Intermediate Similarity	NPD2563	Approved
0.7778	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7309	Approved
0.7733	Intermediate Similarity	NPD6853	Approved
0.7733	Intermediate Similarity	NPD6851	Approved
0.7716	Intermediate Similarity	NPD2978	Approved
0.7716	Intermediate Similarity	NPD2977	Approved
0.7674	Intermediate Similarity	NPD4578	Approved
0.7674	Intermediate Similarity	NPD4577	Approved
0.7647	Intermediate Similarity	NPD1753	Discontinued
0.7644	Intermediate Similarity	NPD4663	Approved
0.7643	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3053	Approved
0.7619	Intermediate Similarity	NPD3055	Approved
0.7616	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3110	Approved
0.7616	Intermediate Similarity	NPD3109	Approved
0.758	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4005	Discontinued
0.7578	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4162	Approved
0.7561	Intermediate Similarity	NPD5977	Approved
0.7561	Intermediate Similarity	NPD5978	Approved
0.7542	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4481	Phase 3
0.7514	Intermediate Similarity	NPD2490	Approved
0.7514	Intermediate Similarity	NPD2488	Approved
0.75	Intermediate Similarity	NPD6090	Discontinued
0.7485	Intermediate Similarity	NPD7110	Phase 1
0.7485	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4055	Discovery
0.7469	Intermediate Similarity	NPD824	Approved
0.7456	Intermediate Similarity	NPD6688	Approved
0.7456	Intermediate Similarity	NPD6687	Approved
0.7453	Intermediate Similarity	NPD2122	Discontinued
0.7452	Intermediate Similarity	NPD4236	Phase 3
0.7452	Intermediate Similarity	NPD4237	Approved
0.7448	Intermediate Similarity	NPD2667	Approved
0.7448	Intermediate Similarity	NPD2668	Approved
0.7438	Intermediate Similarity	NPD4123	Phase 3
0.7434	Intermediate Similarity	NPD4474	Approved
0.7434	Intermediate Similarity	NPD4475	Approved
0.7429	Intermediate Similarity	NPD6618	Phase 2
0.7421	Intermediate Similarity	NPD7124	Phase 2
0.7417	Intermediate Similarity	NPD5156	Approved
0.7417	Intermediate Similarity	NPD5155	Approved
0.7415	Intermediate Similarity	NPD2232	Approved
0.7415	Intermediate Similarity	NPD2233	Approved
0.7415	Intermediate Similarity	NPD2230	Approved
0.7414	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3636	Approved
0.74	Intermediate Similarity	NPD3635	Approved
0.74	Intermediate Similarity	NPD3637	Approved
0.7379	Intermediate Similarity	NPD4093	Discontinued
0.7375	Intermediate Similarity	NPD7598	Phase 2
0.7371	Intermediate Similarity	NPD7280	Phase 3
0.7371	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7281	Phase 3
0.7358	Intermediate Similarity	NPD3692	Discontinued
0.7351	Intermediate Similarity	NPD2606	Approved
0.7351	Intermediate Similarity	NPD2605	Approved
0.7351	Intermediate Similarity	NPD3595	Approved
0.7351	Intermediate Similarity	NPD3594	Approved
0.7346	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1424	Approved
0.7325	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8095	Phase 1
0.7317	Intermediate Similarity	NPD6875	Approved
0.7317	Intermediate Similarity	NPD6876	Approved
0.7315	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5311	Approved
0.7315	Intermediate Similarity	NPD5310	Approved
0.7303	Intermediate Similarity	NPD7291	Discontinued
0.7296	Intermediate Similarity	NPD6748	Discontinued
0.7296	Intermediate Similarity	NPD6331	Phase 2
0.729	Intermediate Similarity	NPD823	Approved
0.729	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD817	Approved
0.7289	Intermediate Similarity	NPD5773	Approved
0.7289	Intermediate Similarity	NPD5772	Approved
0.7284	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7037	Approved
0.7273	Intermediate Similarity	NPD2238	Phase 2
0.7262	Intermediate Similarity	NPD5604	Discontinued
0.7251	Intermediate Similarity	NPD4083	Discontinued
0.7248	Intermediate Similarity	NPD1669	Approved
0.7243	Intermediate Similarity	NPD2494	Approved
0.7243	Intermediate Similarity	NPD3450	Approved
0.7243	Intermediate Similarity	NPD3452	Approved
0.7243	Intermediate Similarity	NPD2493	Approved
0.7241	Intermediate Similarity	NPD7479	Phase 2
0.7222	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7905	Discontinued
0.7219	Intermediate Similarity	NPD6584	Phase 3
0.7215	Intermediate Similarity	NPD3656	Approved
0.7212	Intermediate Similarity	NPD4675	Approved
0.7212	Intermediate Similarity	NPD4678	Approved
0.7208	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5283	Phase 1
0.7192	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD228	Approved
0.7176	Intermediate Similarity	NPD5677	Discontinued
0.717	Intermediate Similarity	NPD7153	Discontinued
0.7161	Intermediate Similarity	NPD3620	Phase 2
0.7161	Intermediate Similarity	NPD3062	Approved
0.7161	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3059	Approved
0.7161	Intermediate Similarity	NPD3061	Approved
0.7152	Intermediate Similarity	NPD4103	Phase 2
0.7152	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4098	Discontinued
0.7152	Intermediate Similarity	NPD2161	Phase 2
0.7143	Intermediate Similarity	NPD5160	Discontinued
0.7143	Intermediate Similarity	NPD3920	Phase 2
0.7143	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4659	Approved
0.7128	Intermediate Similarity	NPD4582	Approved
0.7128	Intermediate Similarity	NPD4583	Approved
0.7126	Intermediate Similarity	NPD5720	Discontinued
0.7126	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD44	Approved
0.7125	Intermediate Similarity	NPD6364	Approved
0.7108	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1132	Approved
0.7097	Intermediate Similarity	NPD1136	Approved
0.7097	Intermediate Similarity	NPD1130	Approved
0.7097	Intermediate Similarity	NPD6612	Phase 2

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