NPASS Compound

Structure

NPC471194 OpenBabel07101719242D 27 31 0 0 1 0 0 0 0 0999 V2000 -4.7988 -1.0657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4679 -0.3226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8206 -0.8578 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 -5.1589 0.6285 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 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 -3.5116 0.0933 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 -4.1808 0.8364 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 -0.8660 0.5000 0.0000 C 0 0 1 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 -0.8660 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 1.7024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 12 2 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 9 11 1 0 0 0 0 10 11 2 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 9 1 1 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 26 2 0 0 0 0 20 24 1 0 0 0 0 20 27 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.11
Volume:	353.051
LogP:	2.495
LogD:	1.974
LogS:	-4.033
# Rotatable Bonds:	2
TPSA:	103.25
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	2.638
Fsp3:	0.05
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:	-4.991
MDCK Permeability:	9.825494089454878e-06
Pgp-inhibitor:	0.011
Pgp-substrate:	0.086
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	97.78754425048828%
Volume Distribution (VD):	0.44
Pgp-substrate:	1.682542324066162%

ADMET: Metabolism

CYP1A2-inhibitor:	0.871
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.645
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.65
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.616
CYP2D6-substrate:	0.586
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	7.035
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.687
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.284
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.072
Carcinogencity:	0.827
Eye Corrosion:	0.003
Eye Irritation:	0.059
Respiratory Toxicity:	0.27

Download Data

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

Natural Product: NPC471194

Natural Product ID:	NPC471194
*Common Name:**	(4S)-4-(1H-Indol-3-Ylmethyl)-4H-Pyrazino[2,1-B]Quinazoline-1,3,6-Trione
IUPAC Name:	(4S)-4-(1H-indol-3-ylmethyl)-4H-pyrazino[2,1-b]quinazoline-1,3,6-trione
Synonyms:
Standard InCHIKey:	PRYGKAJEGXTQNF-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C20H14N4O3/c25-18-16(9-11-10-21-14-7-3-1-5-12(11)14)24-17(19(26)23-18)22-15-8-4-2-6-13(15)20(24)27/h1-8,10,16,21H,9H2,(H,23,25,26)/t16-/m0/s1
SMILES:	OC1=NC(=O)c2n([C@H]1Cc1c[nH]c3c1cccc3)c(=O)c1c(n2)cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386530
PubChem CID:	71725701
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines

*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
NPO33176	cladosporium sp.	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23758051]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	85000.0	nM	PMID[495753]

☑ 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 NPC471194 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	611
0.1-0.2	5218
0.2-0.3	17132
0.3-0.4	13466
0.4-0.5	2272
0.5-0.6	2222
0.6-0.7	1436
0.7-0.8	292
0.8-0.85	28
0.85-0.9	12
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471193
0.9841	High Similarity	NPC72956
0.9789	High Similarity	NPC153980
0.9789	High Similarity	NPC6865
0.9637	High Similarity	NPC471192
0.9271	High Similarity	NPC471191
0.8474	Intermediate Similarity	NPC21429
0.8385	Intermediate Similarity	NPC94752
0.8342	Intermediate Similarity	NPC17059
0.8281	Intermediate Similarity	NPC228835
0.8269	Intermediate Similarity	NPC477715
0.823	Intermediate Similarity	NPC477714
0.8177	Intermediate Similarity	NPC473376
0.8168	Intermediate Similarity	NPC11126
0.8119	Intermediate Similarity	NPC471944
0.8112	Intermediate Similarity	NPC213629
0.8093	Intermediate Similarity	NPC477003
0.8031	Intermediate Similarity	NPC88110
0.8	Intermediate Similarity	NPC165495
0.7989	Intermediate Similarity	NPC63751
0.7979	Intermediate Similarity	NPC248041
0.7979	Intermediate Similarity	NPC126709
0.7979	Intermediate Similarity	NPC283219
0.797	Intermediate Similarity	NPC171317
0.7959	Intermediate Similarity	NPC133003
0.794	Intermediate Similarity	NPC476460
0.7933	Intermediate Similarity	NPC478158
0.7929	Intermediate Similarity	NPC321708
0.7927	Intermediate Similarity	NPC284775
0.7923	Intermediate Similarity	NPC54420
0.7917	Intermediate Similarity	NPC203468
0.7917	Intermediate Similarity	NPC110500
0.7917	Intermediate Similarity	NPC149155
0.7907	Intermediate Similarity	NPC220851
0.7876	Intermediate Similarity	NPC267885
0.7868	Intermediate Similarity	NPC99939
0.7868	Intermediate Similarity	NPC308931
0.7867	Intermediate Similarity	NPC54744
0.7864	Intermediate Similarity	NPC317701
0.7847	Intermediate Similarity	NPC162860
0.7846	Intermediate Similarity	NPC91179
0.7843	Intermediate Similarity	NPC293917
0.7835	Intermediate Similarity	NPC84827
0.7835	Intermediate Similarity	NPC14113
0.7835	Intermediate Similarity	NPC59269
0.7835	Intermediate Similarity	NPC145885
0.783	Intermediate Similarity	NPC478157
0.7822	Intermediate Similarity	NPC202812
0.782	Intermediate Similarity	NPC75634
0.7819	Intermediate Similarity	NPC279918
0.7804	Intermediate Similarity	NPC281049
0.78	Intermediate Similarity	NPC154339
0.7788	Intermediate Similarity	NPC229893
0.7778	Intermediate Similarity	NPC15102
0.7778	Intermediate Similarity	NPC282231
0.7773	Intermediate Similarity	NPC320968
0.7756	Intermediate Similarity	NPC106118
0.7749	Intermediate Similarity	NPC474561
0.7749	Intermediate Similarity	NPC49954
0.7745	Intermediate Similarity	NPC167710
0.7739	Intermediate Similarity	NPC17273
0.7739	Intermediate Similarity	NPC141612
0.7739	Intermediate Similarity	NPC135601
0.7736	Intermediate Similarity	NPC473218
0.7736	Intermediate Similarity	NPC470702
0.7708	Intermediate Similarity	NPC78020
0.7707	Intermediate Similarity	NPC473640
0.7707	Intermediate Similarity	NPC470499
0.7703	Intermediate Similarity	NPC89987
0.77	Intermediate Similarity	NPC470703
0.7689	Intermediate Similarity	NPC54981
0.7685	Intermediate Similarity	NPC267343
0.7685	Intermediate Similarity	NPC326422
0.7682	Intermediate Similarity	NPC157931
0.7681	Intermediate Similarity	NPC475506
0.7673	Intermediate Similarity	NPC117244
0.7673	Intermediate Similarity	NPC473763
0.767	Intermediate Similarity	NPC100321
0.7668	Intermediate Similarity	NPC471943
0.7667	Intermediate Similarity	NPC471155
0.7665	Intermediate Similarity	NPC16659
0.7659	Intermediate Similarity	NPC227582
0.7656	Intermediate Similarity	NPC54988
0.7653	Intermediate Similarity	NPC31385
0.7653	Intermediate Similarity	NPC15573
0.7653	Intermediate Similarity	NPC217372
0.7653	Intermediate Similarity	NPC75726
0.7653	Intermediate Similarity	NPC183662
0.7653	Intermediate Similarity	NPC110602
0.765	Intermediate Similarity	NPC235684
0.7647	Intermediate Similarity	NPC471762
0.7647	Intermediate Similarity	NPC294693
0.7644	Intermediate Similarity	NPC155143
0.763	Intermediate Similarity	NPC270241
0.7626	Intermediate Similarity	NPC64216
0.7626	Intermediate Similarity	NPC191415
0.7624	Intermediate Similarity	NPC324091
0.7621	Intermediate Similarity	NPC131887
0.7619	Intermediate Similarity	NPC225400
0.7614	Intermediate Similarity	NPC265710
0.7614	Intermediate Similarity	NPC219336
0.7612	Intermediate Similarity	NPC278434
0.7606	Intermediate Similarity	NPC82370
0.76	Intermediate Similarity	NPC477549
0.7598	Intermediate Similarity	NPC304203
0.7588	Intermediate Similarity	NPC470205
0.7588	Intermediate Similarity	NPC102755
0.7585	Intermediate Similarity	NPC477004
0.7583	Intermediate Similarity	NPC472538
0.7583	Intermediate Similarity	NPC470786
0.7565	Intermediate Similarity	NPC160105
0.7563	Intermediate Similarity	NPC240088
0.7563	Intermediate Similarity	NPC473380
0.7552	Intermediate Similarity	NPC194640
0.7548	Intermediate Similarity	NPC470497
0.7548	Intermediate Similarity	NPC252338
0.7547	Intermediate Similarity	NPC71238
0.7547	Intermediate Similarity	NPC116555
0.7534	Intermediate Similarity	NPC69843
0.7525	Intermediate Similarity	NPC55772
0.7525	Intermediate Similarity	NPC213468
0.7524	Intermediate Similarity	NPC179701
0.7523	Intermediate Similarity	NPC476491
0.7523	Intermediate Similarity	NPC257851
0.7513	Intermediate Similarity	NPC42372
0.7512	Intermediate Similarity	NPC27041
0.7512	Intermediate Similarity	NPC223791
0.7512	Intermediate Similarity	NPC267811
0.7512	Intermediate Similarity	NPC107077
0.7489	Intermediate Similarity	NPC56109
0.7489	Intermediate Similarity	NPC191382
0.7489	Intermediate Similarity	NPC66777
0.7488	Intermediate Similarity	NPC262898
0.7488	Intermediate Similarity	NPC471199
0.7477	Intermediate Similarity	NPC24370
0.7477	Intermediate Similarity	NPC475736
0.7477	Intermediate Similarity	NPC319232
0.7476	Intermediate Similarity	NPC476874
0.7475	Intermediate Similarity	NPC62749
0.7475	Intermediate Similarity	NPC111275
0.7465	Intermediate Similarity	NPC266249
0.7463	Intermediate Similarity	NPC473342
0.7463	Intermediate Similarity	NPC47190
0.7463	Intermediate Similarity	NPC477167
0.7455	Intermediate Similarity	NPC326363
0.7455	Intermediate Similarity	NPC470730
0.7455	Intermediate Similarity	NPC477175
0.7454	Intermediate Similarity	NPC282247
0.7452	Intermediate Similarity	NPC474916
0.7429	Intermediate Similarity	NPC300183
0.7422	Intermediate Similarity	NPC475859
0.7422	Intermediate Similarity	NPC475969
0.7421	Intermediate Similarity	NPC155444
0.7416	Intermediate Similarity	NPC153123
0.7416	Intermediate Similarity	NPC475914
0.7416	Intermediate Similarity	NPC220797
0.7416	Intermediate Similarity	NPC474318
0.7416	Intermediate Similarity	NPC201266
0.7416	Intermediate Similarity	NPC268744
0.7416	Intermediate Similarity	NPC81535
0.7411	Intermediate Similarity	NPC314603
0.7402	Intermediate Similarity	NPC221873
0.7395	Intermediate Similarity	NPC123839
0.7393	Intermediate Similarity	NPC476073
0.7393	Intermediate Similarity	NPC57398
0.7389	Intermediate Similarity	NPC165743
0.7389	Intermediate Similarity	NPC207686
0.7387	Intermediate Similarity	NPC248454
0.7385	Intermediate Similarity	NPC114637
0.7385	Intermediate Similarity	NPC470731
0.7381	Intermediate Similarity	NPC13456
0.7381	Intermediate Similarity	NPC269203
0.7381	Intermediate Similarity	NPC166209
0.7381	Intermediate Similarity	NPC77241
0.7378	Intermediate Similarity	NPC470729
0.7378	Intermediate Similarity	NPC477176
0.7374	Intermediate Similarity	NPC469938
0.7374	Intermediate Similarity	NPC293216
0.7374	Intermediate Similarity	NPC469529
0.7373	Intermediate Similarity	NPC314882
0.7366	Intermediate Similarity	NPC83111
0.7363	Intermediate Similarity	NPC233936
0.7356	Intermediate Similarity	NPC472293
0.7356	Intermediate Similarity	NPC11445
0.7352	Intermediate Similarity	NPC472285
0.7345	Intermediate Similarity	NPC474877
0.7345	Intermediate Similarity	NPC477177
0.7336	Intermediate Similarity	NPC184225
0.7333	Intermediate Similarity	NPC74413
0.733	Intermediate Similarity	NPC272174
0.733	Intermediate Similarity	NPC138370
0.733	Intermediate Similarity	NPC276657
0.7327	Intermediate Similarity	NPC118940
0.7325	Intermediate Similarity	NPC325976
0.7322	Intermediate Similarity	NPC478006
0.7317	Intermediate Similarity	NPC473666
0.7313	Intermediate Similarity	NPC469896
0.7309	Intermediate Similarity	NPC476817
0.7308	Intermediate Similarity	NPC195239
0.7308	Intermediate Similarity	NPC157828

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 NPC471194 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	652
0.2-0.3	1015
0.3-0.4	2089
0.4-0.5	1982
0.5-0.6	1786
0.6-0.7	1120
0.7-0.8	238
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.8009	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7618	Phase 3
0.8	Intermediate Similarity	NPD7619	Phase 3
0.797	Intermediate Similarity	NPD3961	Discontinued
0.7943	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD482	Approved
0.7913	Intermediate Similarity	NPD5901	Discontinued
0.7854	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7854	Intermediate Similarity	NPD7817	Phase 1
0.785	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD6664	Approved
0.7811	Intermediate Similarity	NPD4922	Phase 2
0.781	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD2095	Phase 2
0.7766	Intermediate Similarity	NPD2094	Phase 2
0.7766	Intermediate Similarity	NPD2092	Phase 2
0.7763	Intermediate Similarity	NPD6164	Phase 2
0.7763	Intermediate Similarity	NPD6165	Phase 2
0.7757	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7970	Approved
0.7734	Intermediate Similarity	NPD7944	Discontinued
0.7727	Intermediate Similarity	NPD2091	Phase 2
0.7727	Intermediate Similarity	NPD2096	Phase 2
0.7721	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6752	Phase 1
0.7706	Intermediate Similarity	NPD6753	Phase 1
0.768	Intermediate Similarity	NPD750	Phase 2
0.7664	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD8093	Discontinued
0.765	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD4988	Discontinued
0.7606	Intermediate Similarity	NPD7470	Discontinued
0.7576	Intermediate Similarity	NPD6595	Phase 3
0.7571	Intermediate Similarity	NPD8114	Approved
0.7571	Intermediate Similarity	NPD8272	Phase 2
0.7571	Intermediate Similarity	NPD8115	Approved
0.7551	Intermediate Similarity	NPD4128	Approved
0.755	Intermediate Similarity	NPD7564	Discontinued
0.7548	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2443	Approved
0.7547	Intermediate Similarity	NPD2442	Approved
0.7524	Intermediate Similarity	NPD4848	Phase 1
0.7524	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD5198	Approved
0.7523	Intermediate Similarity	NPD5199	Approved
0.7513	Intermediate Similarity	NPD4075	Phase 2
0.7512	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5017	Discontinued
0.7512	Intermediate Similarity	NPD3968	Approved
0.75	Intermediate Similarity	NPD3410	Approved
0.75	Intermediate Similarity	NPD3411	Phase 2
0.75	Intermediate Similarity	NPD1506	Discontinued
0.7489	Intermediate Similarity	NPD7781	Approved
0.7489	Intermediate Similarity	NPD7780	Approved
0.7488	Intermediate Similarity	NPD5426	Phase 3
0.7487	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6173	Approved
0.7454	Intermediate Similarity	NPD8094	Discontinued
0.7442	Intermediate Similarity	NPD3915	Approved
0.7442	Intermediate Similarity	NPD4863	Approved
0.7441	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD8431	Approved
0.7434	Intermediate Similarity	NPD7950	Approved
0.7434	Intermediate Similarity	NPD7952	Approved
0.7434	Intermediate Similarity	NPD7789	Approved
0.7434	Intermediate Similarity	NPD7953	Approved
0.7434	Intermediate Similarity	NPD7951	Approved
0.7434	Intermediate Similarity	NPD7790	Approved
0.7434	Intermediate Similarity	NPD7791	Approved
0.743	Intermediate Similarity	NPD5510	Approved
0.7407	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3918	Approved
0.7407	Intermediate Similarity	NPD3917	Approved
0.7389	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD3389	Approved
0.7385	Intermediate Similarity	NPD3393	Approved
0.7385	Intermediate Similarity	NPD3394	Approved
0.7376	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5065	Approved
0.7371	Intermediate Similarity	NPD2008	Discontinued
0.7371	Intermediate Similarity	NPD3967	Approved
0.7366	Intermediate Similarity	NPD7731	Approved
0.7366	Intermediate Similarity	NPD7730	Approved
0.7366	Intermediate Similarity	NPD4845	Discontinued
0.7354	Intermediate Similarity	NPD7271	Approved
0.7353	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2408	Discontinued
0.7346	Intermediate Similarity	NPD7727	Phase 2
0.733	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD2411	Approved
0.7324	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8289	Discontinued
0.7321	Intermediate Similarity	NPD7603	Discontinued
0.7317	Intermediate Similarity	NPD7175	Phase 1
0.7317	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5809	Phase 3
0.7304	Intermediate Similarity	NPD7026	Phase 2
0.7302	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7666	Phase 3
0.7302	Intermediate Similarity	NPD7665	Phase 2
0.7301	Intermediate Similarity	NPD7824	Approved
0.73	Intermediate Similarity	NPD4181	Approved
0.729	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7957	Phase 1
0.7286	Intermediate Similarity	NPD1982	Phase 1
0.7281	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4948	Discontinued
0.7268	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4051	Discontinued
0.7235	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6850	Phase 2
0.7232	Intermediate Similarity	NPD6849	Phase 2
0.723	Intermediate Similarity	NPD8073	Approved
0.7227	Intermediate Similarity	NPD3353	Approved
0.7225	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2509	Approved
0.7222	Intermediate Similarity	NPD2510	Approved
0.7222	Intermediate Similarity	NPD7232	Discontinued
0.7215	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5505	Discontinued
0.7209	Intermediate Similarity	NPD5489	Phase 1
0.7209	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5491	Phase 3
0.7203	Intermediate Similarity	NPD4558	Phase 2
0.7196	Intermediate Similarity	NPD6176	Phase 1
0.7196	Intermediate Similarity	NPD8072	Approved
0.7192	Intermediate Similarity	NPD3178	Discontinued
0.719	Intermediate Similarity	NPD6226	Phase 3
0.7189	Intermediate Similarity	NPD1600	Suspended
0.7188	Intermediate Similarity	NPD5001	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6481	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4079	Approved
0.7178	Intermediate Similarity	NPD4076	Approved
0.7175	Intermediate Similarity	NPD6242	Discontinued
0.717	Intermediate Similarity	NPD6999	Discontinued
0.717	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7308	Discontinued
0.7169	Intermediate Similarity	NPD7657	Approved
0.7169	Intermediate Similarity	NPD7656	Approved
0.7163	Intermediate Similarity	NPD6987	Phase 1
0.7163	Intermediate Similarity	NPD2336	Approved
0.7156	Intermediate Similarity	NPD5446	Phase 2
0.715	Intermediate Similarity	NPD6268	Phase 1
0.715	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7187	Phase 2
0.7143	Intermediate Similarity	NPD5473	Discontinued
0.7136	Intermediate Similarity	NPD484	Approved
0.713	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3506	Approved
0.7129	Intermediate Similarity	NPD3505	Approved
0.7123	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5475	Discontinued
0.712	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2787	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4499	Approved
0.7109	Intermediate Similarity	NPD7027	Phase 3
0.7109	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD8242	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6210	Phase 3
0.7095	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8386	Phase 2
0.7093	Intermediate Similarity	NPD7711	Discontinued
0.7085	Intermediate Similarity	NPD6470	Phase 3
0.7085	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3947	Discontinued
0.7083	Intermediate Similarity	NPD7208	Approved
0.7083	Intermediate Similarity	NPD4299	Phase 1
0.7083	Intermediate Similarity	NPD7209	Approved
0.7083	Intermediate Similarity	NPD7207	Approved
0.7075	Intermediate Similarity	NPD7948	Phase 1
0.7073	Intermediate Similarity	NPD3319	Phase 1
0.7073	Intermediate Similarity	NPD3320	Approved
0.7073	Intermediate Similarity	NPD3318	Approved
0.707	Intermediate Similarity	NPD3773	Approved
0.707	Intermediate Similarity	NPD3774	Approved
0.707	Intermediate Similarity	NPD3775	Approved
0.7064	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6487	Approved
0.7064	Intermediate Similarity	NPD6486	Approved
0.7062	Intermediate Similarity	NPD5853	Phase 3
0.7062	Intermediate Similarity	NPD5855	Phase 3
0.7059	Intermediate Similarity	NPD6787	Phase 2
0.7059	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2823	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2481	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