NPASS Compound

Structure

NPC264285 OpenBabel07101718182D 26 30 0 0 0 0 0 0 0 0999 V2000 2.9921 -2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 -3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 -2.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 -4.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 -4.5441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 -3.5659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9190 -4.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7111 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1759 -4.8531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -2.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7111 -3.2058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 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 0.5878 -0.8090 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 0.3090 -4.1871 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2989 -2.3968 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3838 -5.8312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 11 2 0 0 0 0 4 15 2 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 21 1 0 0 0 0 9 14 2 0 0 0 0 9 22 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 20 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	343.1
Volume:	342.054
LogP:	2.694
LogD:	2.501
LogS:	-4.891
# Rotatable Bonds:	2
TPSA:	97.98
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	2.531
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.426
MDCK Permeability:	5.714560302294558e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	97.3815689086914%
Volume Distribution (VD):	0.801
Pgp-substrate:	2.023035764694214%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.141
CYP2C19-inhibitor:	0.693
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.624
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.634
CYP2D6-substrate:	0.526
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.07

ADMET: Excretion

Clearance (CL):	1.907
Half-life (T1/2):	0.813

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.454
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.141
Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.164
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.145

Download Data

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

Natural Product: NPC264285

Natural Product ID:	NPC264285
*Common Name:**	Arcyriarubin B
IUPAC Name:	3-(6-hydroxy-1H-indol-3-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione
Synonyms:
Standard InCHIKey:	FPFDAPLHFVEXKC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H13N3O3/c24-10-5-6-12-14(9-22-16(12)7-10)18-17(19(25)23-20(18)26)13-8-21-15-4-2-1-3-11(13)15/h1-9,21-22,24H,(H,23,25,26)
SMILES:	c1ccc2c(c1)c(c[nH]2)C1=C(c2c[nH]c3cc(ccc23)O)C(=O)N=C1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495845
PubChem CID:	5327725
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004162] Hydroxyindoles

*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
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO32752	Arcyria obvelata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO10376	Arcyria denudata	Species	Trichiidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	10.0	ug.mL-1	PMID[470799]

☑ 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 NPC264285 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	498
0.1-0.2	3702
0.2-0.3	13246
0.3-0.4	12134
0.4-0.5	8068
0.5-0.6	2419
0.6-0.7	1968
0.7-0.8	610
0.8-0.85	43
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC16352
0.9067	High Similarity	NPC131887
0.8977	High Similarity	NPC78609
0.8744	High Similarity	NPC276657
0.8601	High Similarity	NPC46580
0.8522	High Similarity	NPC183777
0.8507	High Similarity	NPC476073
0.8507	High Similarity	NPC178858
0.85	High Similarity	NPC213308
0.8426	Intermediate Similarity	NPC132329
0.84	Intermediate Similarity	NPC67288
0.835	Intermediate Similarity	NPC77555
0.835	Intermediate Similarity	NPC227582
0.8333	Intermediate Similarity	NPC99666
0.8273	Intermediate Similarity	NPC15801
0.8269	Intermediate Similarity	NPC82370
0.8265	Intermediate Similarity	NPC325976
0.8263	Intermediate Similarity	NPC60621
0.8257	Intermediate Similarity	NPC207686
0.8249	Intermediate Similarity	NPC326363
0.823	Intermediate Similarity	NPC110182
0.8227	Intermediate Similarity	NPC315491
0.8227	Intermediate Similarity	NPC45459
0.8227	Intermediate Similarity	NPC252338
0.8218	Intermediate Similarity	NPC306376
0.8204	Intermediate Similarity	NPC175602
0.8187	Intermediate Similarity	NPC96890
0.8186	Intermediate Similarity	NPC91868
0.8186	Intermediate Similarity	NPC63971
0.8148	Intermediate Similarity	NPC476818
0.8108	Intermediate Similarity	NPC235685
0.8107	Intermediate Similarity	NPC134848
0.8086	Intermediate Similarity	NPC61038
0.8077	Intermediate Similarity	NPC270918
0.8075	Intermediate Similarity	NPC27041
0.8072	Intermediate Similarity	NPC101350
0.806	Intermediate Similarity	NPC324149
0.8057	Intermediate Similarity	NPC219087
0.8053	Intermediate Similarity	NPC160898
0.8038	Intermediate Similarity	NPC86834
0.8038	Intermediate Similarity	NPC210828
0.8038	Intermediate Similarity	NPC171787
0.8038	Intermediate Similarity	NPC39679
0.803	Intermediate Similarity	NPC314002
0.803	Intermediate Similarity	NPC242209
0.8028	Intermediate Similarity	NPC24370
0.8028	Intermediate Similarity	NPC319232
0.802	Intermediate Similarity	NPC220765
0.8019	Intermediate Similarity	NPC53144
0.8017	Intermediate Similarity	NPC63109
0.8009	Intermediate Similarity	NPC23294
0.8	Intermediate Similarity	NPC269270
0.8	Intermediate Similarity	NPC74413
0.799	Intermediate Similarity	NPC156704
0.799	Intermediate Similarity	NPC88008
0.798	Intermediate Similarity	NPC326634
0.798	Intermediate Similarity	NPC204717
0.7972	Intermediate Similarity	NPC294620
0.7971	Intermediate Similarity	NPC260900
0.7963	Intermediate Similarity	NPC14686
0.7962	Intermediate Similarity	NPC303951
0.7959	Intermediate Similarity	NPC72980
0.7953	Intermediate Similarity	NPC303658
0.7944	Intermediate Similarity	NPC170114
0.794	Intermediate Similarity	NPC475746
0.7936	Intermediate Similarity	NPC229893
0.7934	Intermediate Similarity	NPC207866
0.7917	Intermediate Similarity	NPC193267
0.7917	Intermediate Similarity	NPC213530
0.791	Intermediate Similarity	NPC321708
0.7908	Intermediate Similarity	NPC111275
0.7907	Intermediate Similarity	NPC472285
0.79	Intermediate Similarity	NPC171171
0.7897	Intermediate Similarity	NPC470549
0.7892	Intermediate Similarity	NPC276517
0.7873	Intermediate Similarity	NPC194740
0.786	Intermediate Similarity	NPC322064
0.786	Intermediate Similarity	NPC330009
0.7854	Intermediate Similarity	NPC122436
0.785	Intermediate Similarity	NPC477610
0.7847	Intermediate Similarity	NPC200836
0.7846	Intermediate Similarity	NPC474409
0.784	Intermediate Similarity	NPC87413
0.7834	Intermediate Similarity	NPC74360
0.7822	Intermediate Similarity	NPC477549
0.7817	Intermediate Similarity	NPC184964
0.7814	Intermediate Similarity	NPC474412
0.7812	Intermediate Similarity	NPC323752
0.781	Intermediate Similarity	NPC285558
0.781	Intermediate Similarity	NPC470500
0.781	Intermediate Similarity	NPC475070
0.7808	Intermediate Similarity	NPC220851
0.7793	Intermediate Similarity	NPC85273
0.7793	Intermediate Similarity	NPC5145
0.7793	Intermediate Similarity	NPC11464
0.7788	Intermediate Similarity	NPC28945
0.7783	Intermediate Similarity	NPC83111
0.7778	Intermediate Similarity	NPC36405
0.7778	Intermediate Similarity	NPC3207
0.7772	Intermediate Similarity	NPC278434
0.7767	Intermediate Similarity	NPC31700
0.7763	Intermediate Similarity	NPC473317
0.7762	Intermediate Similarity	NPC476098
0.7761	Intermediate Similarity	NPC94943
0.7756	Intermediate Similarity	NPC106937
0.775	Intermediate Similarity	NPC212535
0.7742	Intermediate Similarity	NPC305984
0.7731	Intermediate Similarity	NPC237740
0.7729	Intermediate Similarity	NPC74153
0.7721	Intermediate Similarity	NPC12344
0.7717	Intermediate Similarity	NPC150239
0.7711	Intermediate Similarity	NPC190007
0.7706	Intermediate Similarity	NPC247803
0.7692	Intermediate Similarity	NPC153400
0.7688	Intermediate Similarity	NPC55772
0.7685	Intermediate Similarity	NPC282247
0.767	Intermediate Similarity	NPC473821
0.7667	Intermediate Similarity	NPC232727
0.7665	Intermediate Similarity	NPC473187
0.7661	Intermediate Similarity	NPC304926
0.7661	Intermediate Similarity	NPC476041
0.7659	Intermediate Similarity	NPC476460
0.7658	Intermediate Similarity	NPC125597
0.7655	Intermediate Similarity	NPC220852
0.7653	Intermediate Similarity	NPC249583
0.7653	Intermediate Similarity	NPC4687
0.7652	Intermediate Similarity	NPC295452
0.7652	Intermediate Similarity	NPC171393
0.7644	Intermediate Similarity	NPC260434
0.7642	Intermediate Similarity	NPC477861
0.7639	Intermediate Similarity	NPC316981
0.7635	Intermediate Similarity	NPC62749
0.7632	Intermediate Similarity	NPC285343
0.763	Intermediate Similarity	NPC211813
0.7628	Intermediate Similarity	NPC167860
0.7628	Intermediate Similarity	NPC123976
0.7628	Intermediate Similarity	NPC309845
0.7626	Intermediate Similarity	NPC477609
0.7617	Intermediate Similarity	NPC131718
0.7611	Intermediate Similarity	NPC200553
0.7611	Intermediate Similarity	NPC279189
0.761	Intermediate Similarity	NPC154339
0.7604	Intermediate Similarity	NPC266931
0.7602	Intermediate Similarity	NPC78020
0.7598	Intermediate Similarity	NPC41679
0.7593	Intermediate Similarity	NPC9894
0.7592	Intermediate Similarity	NPC77101
0.7583	Intermediate Similarity	NPC300183
0.7577	Intermediate Similarity	NPC70155
0.7562	Intermediate Similarity	NPC271792
0.7561	Intermediate Similarity	NPC32771
0.756	Intermediate Similarity	NPC153042
0.7557	Intermediate Similarity	NPC174760
0.7555	Intermediate Similarity	NPC184225
0.755	Intermediate Similarity	NPC59269
0.7549	Intermediate Similarity	NPC315555
0.7538	Intermediate Similarity	NPC110500
0.7538	Intermediate Similarity	NPC149155
0.7538	Intermediate Similarity	NPC203468
0.7534	Intermediate Similarity	NPC183407
0.7534	Intermediate Similarity	NPC130570
0.7534	Intermediate Similarity	NPC203614
0.7534	Intermediate Similarity	NPC204491
0.7534	Intermediate Similarity	NPC469928
0.7533	Intermediate Similarity	NPC196718
0.7531	Intermediate Similarity	NPC74619
0.7524	Intermediate Similarity	NPC192315
0.7522	Intermediate Similarity	NPC470784
0.7512	Intermediate Similarity	NPC11445
0.7512	Intermediate Similarity	NPC98715
0.7512	Intermediate Similarity	NPC251090
0.7512	Intermediate Similarity	NPC17059
0.7512	Intermediate Similarity	NPC294375
0.7512	Intermediate Similarity	NPC13880
0.7511	Intermediate Similarity	NPC314882
0.7511	Intermediate Similarity	NPC162002
0.75	Intermediate Similarity	NPC271862
0.75	Intermediate Similarity	NPC117980
0.75	Intermediate Similarity	NPC179287
0.75	Intermediate Similarity	NPC307963
0.75	Intermediate Similarity	NPC325297
0.75	Intermediate Similarity	NPC267343
0.75	Intermediate Similarity	NPC308931
0.75	Intermediate Similarity	NPC99939
0.75	Intermediate Similarity	NPC15102
0.75	Intermediate Similarity	NPC267885
0.75	Intermediate Similarity	NPC469727
0.7488	Intermediate Similarity	NPC476167
0.7488	Intermediate Similarity	NPC283117
0.7478	Intermediate Similarity	NPC477608
0.7478	Intermediate Similarity	NPC184680
0.7478	Intermediate Similarity	NPC477607
0.7477	Intermediate Similarity	NPC128084
0.7477	Intermediate Similarity	NPC308137
0.7477	Intermediate Similarity	NPC310211
0.7476	Intermediate Similarity	NPC78767
0.7476	Intermediate Similarity	NPC70956
0.7476	Intermediate Similarity	NPC243834
0.7476	Intermediate Similarity	NPC473814
0.7474	Intermediate Similarity	NPC135141

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 NPC264285 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	627
0.2-0.3	883
0.3-0.4	1470
0.4-0.5	2715
0.5-0.6	2110
0.6-0.7	948
0.7-0.8	108
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8424	Intermediate Similarity	NPD5426	Phase 3
0.8267	Intermediate Similarity	NPD6999	Discontinued
0.8267	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD484	Approved
0.8208	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7001	Phase 3
0.8204	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD7948	Phase 1
0.802	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD5901	Discontinued
0.7952	Intermediate Similarity	NPD7666	Phase 3
0.7952	Intermediate Similarity	NPD7665	Phase 2
0.7945	Intermediate Similarity	NPD7603	Discontinued
0.7909	Intermediate Similarity	NPD4845	Discontinued
0.7867	Intermediate Similarity	NPD2916	Discontinued
0.7812	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7804	Intermediate Similarity	NPD4852	Phase 2
0.7756	Intermediate Similarity	NPD802	Phase 2
0.7717	Intermediate Similarity	NPD6242	Discontinued
0.7673	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD6165	Phase 2
0.7668	Intermediate Similarity	NPD6164	Phase 2
0.7611	Intermediate Similarity	NPD3746	Discontinued
0.7593	Intermediate Similarity	NPD7470	Discontinued
0.7565	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD482	Approved
0.7537	Intermediate Similarity	NPD2091	Phase 2
0.7537	Intermediate Similarity	NPD2096	Phase 2
0.7534	Intermediate Similarity	NPD5612	Discontinued
0.75	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1038	Approved
0.7488	Intermediate Similarity	NPD2094	Phase 2
0.7488	Intermediate Similarity	NPD8395	Approved
0.7488	Intermediate Similarity	NPD8396	Approved
0.7488	Intermediate Similarity	NPD2095	Phase 2
0.7488	Intermediate Similarity	NPD2092	Phase 2
0.7488	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD8093	Discontinued
0.7475	Intermediate Similarity	NPD6595	Phase 3
0.7458	Intermediate Similarity	NPD5482	Discontinued
0.7454	Intermediate Similarity	NPD2509	Approved
0.7454	Intermediate Similarity	NPD2510	Approved
0.745	Intermediate Similarity	NPD5065	Approved
0.7445	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8094	Discontinued
0.7427	Intermediate Similarity	NPD6531	Approved
0.7427	Intermediate Similarity	NPD6530	Approved
0.7424	Intermediate Similarity	NPD2844	Phase 3
0.7424	Intermediate Similarity	NPD7558	Phase 2
0.7412	Intermediate Similarity	NPD8349	Phase 1
0.74	Intermediate Similarity	NPD7181	Phase 3
0.7376	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6995	Phase 1
0.7333	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD5632	Approved
0.7308	Intermediate Similarity	NPD6790	Phase 1
0.7306	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1392	Approved
0.7246	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD8284	Discontinued
0.7233	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD750	Phase 2
0.7215	Intermediate Similarity	NPD6376	Discontinued
0.7207	Intermediate Similarity	NPD3243	Approved
0.7202	Intermediate Similarity	NPD3003	Approved
0.7202	Intermediate Similarity	NPD8091	Phase 3
0.7198	Intermediate Similarity	NPD4373	Phase 2
0.7195	Intermediate Similarity	NPD6456	Discontinued
0.7188	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD4948	Discontinued
0.7176	Intermediate Similarity	NPD4511	Phase 1
0.7169	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3814	Phase 1
0.7163	Intermediate Similarity	NPD3825	Phase 3
0.7162	Intermediate Similarity	NPD3330	Phase 1
0.7162	Intermediate Similarity	NPD8096	Phase 3
0.7162	Intermediate Similarity	NPD8097	Phase 3
0.7156	Intermediate Similarity	NPD8098	Approved
0.7155	Intermediate Similarity	NPD4885	Approved
0.7149	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4952	Phase 3
0.7136	Intermediate Similarity	NPD5658	Approved
0.7129	Intermediate Similarity	NPD1326	Approved
0.7129	Intermediate Similarity	NPD1325	Approved
0.7125	Intermediate Similarity	NPD4558	Phase 2
0.7123	Intermediate Similarity	NPD8403	Phase 1
0.7123	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3178	Discontinued
0.7097	Intermediate Similarity	NPD5450	Discontinued
0.7095	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7426	Phase 1
0.7083	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3354	Phase 2
0.7078	Intermediate Similarity	NPD3947	Discontinued
0.7078	Intermediate Similarity	NPD6987	Phase 1
0.7075	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3389	Approved
0.7067	Intermediate Similarity	NPD3394	Approved
0.7067	Intermediate Similarity	NPD3393	Approved
0.7064	Intermediate Similarity	NPD3006	Discontinued
0.7064	Intermediate Similarity	NPD6975	Discontinued
0.7053	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6665	Discontinued
0.704	Intermediate Similarity	NPD5067	Phase 2
0.704	Intermediate Similarity	NPD5066	Phase 2
0.704	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7946	Pre-registration
0.7033	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5902	Approved
0.7022	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5903	Approved
0.7014	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD4429	Discontinued
0.7	Intermediate Similarity	NPD4795	Phase 2
0.6991	Remote Similarity	NPD5003	Discontinued
0.6983	Remote Similarity	NPD3259	Approved
0.6982	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3404	Approved
0.6953	Remote Similarity	NPD5559	Phase 2
0.6947	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD8431	Approved
0.6931	Remote Similarity	NPD5140	Approved
0.6931	Remote Similarity	NPD5138	Approved
0.6927	Remote Similarity	NPD1768	Approved
0.6923	Remote Similarity	NPD8512	Phase 3
0.692	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD2781	Approved
0.6909	Remote Similarity	NPD8073	Approved
0.6906	Remote Similarity	NPD2189	Approved
0.6906	Remote Similarity	NPD2187	Approved
0.6901	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3258	Approved
0.6898	Remote Similarity	NPD7618	Phase 3
0.6898	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7944	Discontinued
0.6898	Remote Similarity	NPD7619	Phase 3
0.6897	Remote Similarity	NPD2782	Approved
0.6897	Remote Similarity	NPD2780	Approved
0.6895	Remote Similarity	NPD1740	Approved
0.6895	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD1739	Approved
0.6894	Remote Similarity	NPD7688	Phase 1
0.6891	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5937	Approved
0.6878	Remote Similarity	NPD6964	Approved
0.6878	Remote Similarity	NPD6963	Approved
0.6872	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7711	Discontinued
0.6861	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7452	Approved
0.6861	Remote Similarity	NPD7453	Approved
0.6861	Remote Similarity	NPD7222	Phase 2
0.6858	Remote Similarity	NPD7069	Discontinued
0.6856	Remote Similarity	NPD7878	Phase 2
0.6851	Remote Similarity	NPD5022	Discontinued
0.6851	Remote Similarity	NPD5479	Discontinued
0.6849	Remote Similarity	NPD2175	Phase 3
0.6849	Remote Similarity	NPD2176	Approved
0.6849	Remote Similarity	NPD2177	Approved
0.6847	Remote Similarity	NPD8283	Approved
0.6847	Remote Similarity	NPD56	Approved
0.6847	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8282	Approved
0.6846	Remote Similarity	NPD6517	Phase 3
0.6846	Remote Similarity	NPD6716	Phase 1
0.6842	Remote Similarity	NPD8160	Phase 2
0.6842	Remote Similarity	NPD6733	Discontinued
0.6835	Remote Similarity	NPD7951	Approved
0.6835	Remote Similarity	NPD7791	Approved
0.6835	Remote Similarity	NPD7790	Approved
0.6835	Remote Similarity	NPD7950	Approved
0.6835	Remote Similarity	NPD7953	Approved
0.6835	Remote Similarity	NPD7789	Approved
0.6835	Remote Similarity	NPD7952	Approved
0.6835	Remote Similarity	NPD4850	Phase 1
0.6835	Remote Similarity	NPD6494	Phase 2
0.6833	Remote Similarity	NPD3931	Approved
0.6833	Remote Similarity	NPD3928	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