NPASS Compound

Structure

NPC72956 OpenBabel07101718222D 26 30 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 -0.8660 1.5000 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 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 2 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 0.0000 -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 -0.0000 2.0000 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 -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 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 13 2 0 0 0 0 6 14 2 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 12 1 0 0 0 0 10 12 2 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 9 1 1 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 20 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.13
Volume:	346.897
LogP:	2.027
LogD:	1.879
LogS:	-3.93
# Rotatable Bonds:	2
TPSA:	79.78
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	2.989
Fsp3:	0.15
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:	-4.91
MDCK Permeability:	1.243328551936429e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.058
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.854
30% Bioavailability (F30%):	0.394

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817
Plasma Protein Binding (PPB):	93.85292053222656%
Volume Distribution (VD):	1.127
Pgp-substrate:	3.519845485687256%

ADMET: Metabolism

CYP1A2-inhibitor:	0.437
CYP1A2-substrate:	0.286
CYP2C19-inhibitor:	0.894
CYP2C19-substrate:	0.178
CYP2C9-inhibitor:	0.709
CYP2C9-substrate:	0.745
CYP2D6-inhibitor:	0.641
CYP2D6-substrate:	0.365
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	7.971
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.497
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.764
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.111
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.245

Download Data

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

Natural Product: NPC72956

Natural Product ID:	NPC72956
*Common Name:**	Glyantrypine
IUPAC Name:	(4R)-4-(1H-indol-3-ylmethyl)-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
Synonyms:
Standard InCHIKey:	YFNRNQBGKNOAPT-QGZVFWFLSA-N
Standard InCHI:	InChI=1S/C20H16N4O2/c25-19-17(9-12-10-21-15-7-3-1-5-13(12)15)24-18(11-22-19)23-16-8-4-2-6-14(16)20(24)26/h1-8,10,17,21H,9,11H2,(H,22,25)/t17-/m1/s1
SMILES:	OC1=NCc2n([C@@H]1Cc1c[nH]c3c1cccc3)c(=O)c1c(n2)cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386539
PubChem CID:	11131721
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	=	100000.0	nM	PMID[545248]

☑ 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 NPC72956 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	544
0.1-0.2	4915
0.2-0.3	16747
0.3-0.4	14154
0.4-0.5	2289
0.5-0.6	2207
0.6-0.7	1488
0.7-0.8	306
0.8-0.85	27
0.85-0.9	12
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9947	High Similarity	NPC153980
0.9947	High Similarity	NPC6865
0.9841	High Similarity	NPC471193
0.9841	High Similarity	NPC471194
0.9791	High Similarity	NPC471192
0.9319	High Similarity	NPC471191
0.8519	High Similarity	NPC21429
0.8385	Intermediate Similarity	NPC17059
0.8333	Intermediate Similarity	NPC94752
0.8325	Intermediate Similarity	NPC228835
0.8309	Intermediate Similarity	NPC477715
0.8269	Intermediate Similarity	NPC477714
0.8218	Intermediate Similarity	NPC473376
0.8211	Intermediate Similarity	NPC11126
0.8154	Intermediate Similarity	NPC213629
0.8128	Intermediate Similarity	NPC63751
0.8073	Intermediate Similarity	NPC88110
0.8041	Intermediate Similarity	NPC477003
0.8041	Intermediate Similarity	NPC165495
0.8	Intermediate Similarity	NPC308931
0.8	Intermediate Similarity	NPC99939
0.798	Intermediate Similarity	NPC471944
0.7971	Intermediate Similarity	NPC478158
0.797	Intermediate Similarity	NPC321708
0.7969	Intermediate Similarity	NPC59269
0.7961	Intermediate Similarity	NPC54420
0.7944	Intermediate Similarity	NPC220851
0.7921	Intermediate Similarity	NPC171317
0.7908	Intermediate Similarity	NPC15102
0.7908	Intermediate Similarity	NPC133003
0.7905	Intermediate Similarity	NPC54744
0.7889	Intermediate Similarity	NPC476460
0.7887	Intermediate Similarity	NPC91179
0.7885	Intermediate Similarity	NPC162860
0.7884	Intermediate Similarity	NPC474561
0.7884	Intermediate Similarity	NPC49954
0.7882	Intermediate Similarity	NPC293917
0.7868	Intermediate Similarity	NPC17273
0.7868	Intermediate Similarity	NPC135601
0.7868	Intermediate Similarity	NPC141612
0.7867	Intermediate Similarity	NPC478157
0.7865	Intermediate Similarity	NPC203468
0.7865	Intermediate Similarity	NPC149155
0.7865	Intermediate Similarity	NPC110500
0.7861	Intermediate Similarity	NPC279918
0.7861	Intermediate Similarity	NPC202812
0.7857	Intermediate Similarity	NPC75634
0.7839	Intermediate Similarity	NPC154339
0.7835	Intermediate Similarity	NPC248041
0.7835	Intermediate Similarity	NPC126709
0.7835	Intermediate Similarity	NPC283219
0.7824	Intermediate Similarity	NPC267885
0.7819	Intermediate Similarity	NPC282231
0.7816	Intermediate Similarity	NPC317701
0.781	Intermediate Similarity	NPC320968
0.7784	Intermediate Similarity	NPC145885
0.7784	Intermediate Similarity	NPC84827
0.7784	Intermediate Similarity	NPC284775
0.7784	Intermediate Similarity	NPC14113
0.7783	Intermediate Similarity	NPC227582
0.7757	Intermediate Similarity	NPC281049
0.7749	Intermediate Similarity	NPC78020
0.7745	Intermediate Similarity	NPC473640
0.7745	Intermediate Similarity	NPC470499
0.7725	Intermediate Similarity	NPC54981
0.7723	Intermediate Similarity	NPC267343
0.7718	Intermediate Similarity	NPC475506
0.7717	Intermediate Similarity	NPC157931
0.7716	Intermediate Similarity	NPC470205
0.7713	Intermediate Similarity	NPC477549
0.7711	Intermediate Similarity	NPC473763
0.7711	Intermediate Similarity	NPC117244
0.7707	Intermediate Similarity	NPC100321
0.7707	Intermediate Similarity	NPC106118
0.7696	Intermediate Similarity	NPC160105
0.7696	Intermediate Similarity	NPC54988
0.7689	Intermediate Similarity	NPC110602
0.7689	Intermediate Similarity	NPC75726
0.7689	Intermediate Similarity	NPC31385
0.7688	Intermediate Similarity	NPC235684
0.7685	Intermediate Similarity	NPC294693
0.7684	Intermediate Similarity	NPC194640
0.7682	Intermediate Similarity	NPC471762
0.7681	Intermediate Similarity	NPC155143
0.767	Intermediate Similarity	NPC252338
0.7661	Intermediate Similarity	NPC229893
0.7659	Intermediate Similarity	NPC131887
0.7658	Intermediate Similarity	NPC89987
0.7653	Intermediate Similarity	NPC213468
0.765	Intermediate Similarity	NPC278434
0.7636	Intermediate Similarity	NPC476491
0.7619	Intermediate Similarity	NPC471155
0.7614	Intermediate Similarity	NPC16659
0.761	Intermediate Similarity	NPC167710
0.7606	Intermediate Similarity	NPC473218
0.7606	Intermediate Similarity	NPC470702
0.7586	Intermediate Similarity	NPC473342
0.7586	Intermediate Similarity	NPC477167
0.7585	Intermediate Similarity	NPC470497
0.7583	Intermediate Similarity	NPC71238
0.7583	Intermediate Similarity	NPC270241
0.758	Intermediate Similarity	NPC64216
0.7574	Intermediate Similarity	NPC324091
0.7571	Intermediate Similarity	NPC225400
0.757	Intermediate Similarity	NPC470703
0.7563	Intermediate Similarity	NPC265710
0.7563	Intermediate Similarity	NPC55772
0.7557	Intermediate Similarity	NPC257851
0.7552	Intermediate Similarity	NPC42372
0.7549	Intermediate Similarity	NPC326422
0.7549	Intermediate Similarity	NPC304203
0.7548	Intermediate Similarity	NPC300183
0.7547	Intermediate Similarity	NPC223791
0.7547	Intermediate Similarity	NPC107077
0.7538	Intermediate Similarity	NPC314603
0.7536	Intermediate Similarity	NPC470786
0.7536	Intermediate Similarity	NPC477004
0.7536	Intermediate Similarity	NPC472538
0.7526	Intermediate Similarity	NPC471943
0.7523	Intermediate Similarity	NPC66777
0.7513	Intermediate Similarity	NPC183662
0.7513	Intermediate Similarity	NPC217372
0.7513	Intermediate Similarity	NPC248454
0.7513	Intermediate Similarity	NPC111275
0.7513	Intermediate Similarity	NPC15573
0.7512	Intermediate Similarity	NPC476874
0.7512	Intermediate Similarity	NPC62749
0.7511	Intermediate Similarity	NPC319232
0.7511	Intermediate Similarity	NPC24370
0.7489	Intermediate Similarity	NPC69843
0.7489	Intermediate Similarity	NPC326363
0.7488	Intermediate Similarity	NPC282247
0.7488	Intermediate Similarity	NPC474916
0.7487	Intermediate Similarity	NPC191415
0.7487	Intermediate Similarity	NPC233936
0.7477	Intermediate Similarity	NPC82370
0.7476	Intermediate Similarity	NPC11445
0.7475	Intermediate Similarity	NPC219336
0.7452	Intermediate Similarity	NPC201266
0.7452	Intermediate Similarity	NPC220797
0.7452	Intermediate Similarity	NPC474318
0.7452	Intermediate Similarity	NPC475914
0.7452	Intermediate Similarity	NPC74413
0.7452	Intermediate Similarity	NPC268744
0.7452	Intermediate Similarity	NPC153123
0.745	Intermediate Similarity	NPC102755
0.7444	Intermediate Similarity	NPC191382
0.7444	Intermediate Similarity	NPC56109
0.744	Intermediate Similarity	NPC471199
0.744	Intermediate Similarity	NPC262898
0.7429	Intermediate Similarity	NPC476073
0.7427	Intermediate Similarity	NPC195239
0.7427	Intermediate Similarity	NPC157828
0.7424	Intermediate Similarity	NPC240088
0.7424	Intermediate Similarity	NPC473380
0.7423	Intermediate Similarity	NPC114637
0.7418	Intermediate Similarity	NPC116555
0.7416	Intermediate Similarity	NPC303820
0.7416	Intermediate Similarity	NPC166209
0.7416	Intermediate Similarity	NPC13456
0.7416	Intermediate Similarity	NPC77241
0.7416	Intermediate Similarity	NPC269203
0.7416	Intermediate Similarity	NPC205254
0.7416	Intermediate Similarity	NPC106771
0.7416	Intermediate Similarity	NPC23420
0.7415	Intermediate Similarity	NPC47190
0.7411	Intermediate Similarity	NPC477175
0.7411	Intermediate Similarity	NPC469938
0.7411	Intermediate Similarity	NPC469529
0.7411	Intermediate Similarity	NPC293216
0.7411	Intermediate Similarity	NPC470730
0.7407	Intermediate Similarity	NPC469765
0.7407	Intermediate Similarity	NPC469786
0.7407	Intermediate Similarity	NPC259644
0.7407	Intermediate Similarity	NPC25008
0.7407	Intermediate Similarity	NPC469760
0.7407	Intermediate Similarity	NPC469763
0.7407	Intermediate Similarity	NPC73952
0.7402	Intermediate Similarity	NPC83111
0.7391	Intermediate Similarity	NPC179701
0.7387	Intermediate Similarity	NPC248462
0.7385	Intermediate Similarity	NPC267811
0.7385	Intermediate Similarity	NPC27041
0.7382	Intermediate Similarity	NPC469762
0.7381	Intermediate Similarity	NPC475935
0.7381	Intermediate Similarity	NPC94211
0.7381	Intermediate Similarity	NPC52909
0.7378	Intermediate Similarity	NPC475969
0.7378	Intermediate Similarity	NPC475859
0.7376	Intermediate Similarity	NPC155444
0.7368	Intermediate Similarity	NPC211572
0.7368	Intermediate Similarity	NPC80597
0.7368	Intermediate Similarity	NPC70922
0.7368	Intermediate Similarity	NPC75540
0.7368	Intermediate Similarity	NPC212376
0.7366	Intermediate Similarity	NPC138370
0.7364	Intermediate Similarity	NPC276657
0.7363	Intermediate Similarity	NPC163055
0.7362	Intermediate Similarity	NPC471536
0.7357	Intermediate Similarity	NPC325976

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 NPC72956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	638
0.2-0.3	1016
0.3-0.4	2048
0.4-0.5	2011
0.5-0.6	1746
0.6-0.7	1167
0.7-0.8	265
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8374	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8317	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.8048	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.804	Intermediate Similarity	NPD7618	Phase 3
0.804	Intermediate Similarity	NPD7619	Phase 3
0.8039	Intermediate Similarity	NPD5901	Discontinued
0.7981	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.796	Intermediate Similarity	NPD6664	Approved
0.794	Intermediate Similarity	NPD4922	Phase 2
0.7933	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3961	Discontinued
0.7882	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD6165	Phase 2
0.788	Intermediate Similarity	NPD6164	Phase 2
0.7865	Intermediate Similarity	NPD482	Approved
0.7847	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2095	Phase 2
0.7806	Intermediate Similarity	NPD2094	Phase 2
0.7806	Intermediate Similarity	NPD2092	Phase 2
0.7806	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7817	Phase 1
0.7805	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD7970	Approved
0.7783	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7773	Intermediate Similarity	NPD8093	Discontinued
0.7772	Intermediate Similarity	NPD7944	Discontinued
0.7766	Intermediate Similarity	NPD2096	Phase 2
0.7766	Intermediate Similarity	NPD2091	Phase 2
0.7757	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6595	Phase 3
0.768	Intermediate Similarity	NPD4128	Approved
0.7677	Intermediate Similarity	NPD7564	Discontinued
0.767	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2443	Approved
0.7667	Intermediate Similarity	NPD2442	Approved
0.7661	Intermediate Similarity	NPD6753	Phase 1
0.7661	Intermediate Similarity	NPD6752	Phase 1
0.7642	Intermediate Similarity	NPD7470	Discontinued
0.7641	Intermediate Similarity	NPD4075	Phase 2
0.7638	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD750	Phase 2
0.7617	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7608	Intermediate Similarity	NPD8272	Phase 2
0.7608	Intermediate Similarity	NPD5426	Phase 3
0.7602	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD8094	Discontinued
0.7562	Intermediate Similarity	NPD8431	Approved
0.7562	Intermediate Similarity	NPD4988	Discontinued
0.7561	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4848	Phase 1
0.756	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD4863	Approved
0.7524	Intermediate Similarity	NPD8115	Approved
0.7524	Intermediate Similarity	NPD8114	Approved
0.75	Intermediate Similarity	NPD5065	Approved
0.75	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD2008	Discontinued
0.7477	Intermediate Similarity	NPD5198	Approved
0.7477	Intermediate Similarity	NPD5199	Approved
0.7465	Intermediate Similarity	NPD2408	Discontinued
0.7465	Intermediate Similarity	NPD3968	Approved
0.7464	Intermediate Similarity	NPD5017	Discontinued
0.7453	Intermediate Similarity	NPD3411	Phase 2
0.7453	Intermediate Similarity	NPD3410	Approved
0.7451	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7780	Approved
0.7444	Intermediate Similarity	NPD7781	Approved
0.7442	Intermediate Similarity	NPD2411	Approved
0.7438	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7175	Phase 1
0.7424	Intermediate Similarity	NPD4181	Approved
0.7421	Intermediate Similarity	NPD6173	Approved
0.7418	Intermediate Similarity	NPD7666	Phase 3
0.7418	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7665	Phase 2
0.7406	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD7957	Phase 1
0.7404	Intermediate Similarity	NPD1982	Phase 1
0.7395	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD3915	Approved
0.7389	Intermediate Similarity	NPD7950	Approved
0.7389	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7791	Approved
0.7389	Intermediate Similarity	NPD7790	Approved
0.7389	Intermediate Similarity	NPD7953	Approved
0.7389	Intermediate Similarity	NPD7789	Approved
0.7389	Intermediate Similarity	NPD7952	Approved
0.7389	Intermediate Similarity	NPD4948	Discontinued
0.7389	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7951	Approved
0.7383	Intermediate Similarity	NPD5510	Approved
0.7371	Intermediate Similarity	NPD1506	Discontinued
0.7361	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3917	Approved
0.7361	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3918	Approved
0.7358	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7603	Discontinued
0.7349	Intermediate Similarity	NPD4051	Discontinued
0.7346	Intermediate Similarity	NPD8073	Approved
0.7343	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6850	Phase 2
0.7342	Intermediate Similarity	NPD6849	Phase 2
0.734	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD3393	Approved
0.7339	Intermediate Similarity	NPD3389	Approved
0.7339	Intermediate Similarity	NPD3394	Approved
0.7336	Intermediate Similarity	NPD7232	Discontinued
0.7336	Intermediate Similarity	NPD2510	Approved
0.7336	Intermediate Similarity	NPD2509	Approved
0.733	Intermediate Similarity	NPD5505	Discontinued
0.7327	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3967	Approved
0.7324	Intermediate Similarity	NPD5491	Phase 3
0.7324	Intermediate Similarity	NPD5489	Phase 1
0.7321	Intermediate Similarity	NPD7731	Approved
0.7321	Intermediate Similarity	NPD7730	Approved
0.7321	Intermediate Similarity	NPD4845	Discontinued
0.7311	Intermediate Similarity	NPD8072	Approved
0.7311	Intermediate Similarity	NPD6176	Phase 1
0.7309	Intermediate Similarity	NPD7271	Approved
0.7308	Intermediate Similarity	NPD6226	Phase 3
0.73	Intermediate Similarity	NPD4079	Approved
0.73	Intermediate Similarity	NPD4076	Approved
0.7299	Intermediate Similarity	NPD7727	Phase 2
0.7286	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6999	Discontinued
0.7285	Intermediate Similarity	NPD6242	Discontinued
0.7281	Intermediate Similarity	NPD7656	Approved
0.7281	Intermediate Similarity	NPD7657	Approved
0.7277	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6987	Phase 1
0.7277	Intermediate Similarity	NPD8289	Discontinued
0.7273	Intermediate Similarity	NPD5446	Phase 2
0.7269	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7187	Phase 2
0.7264	Intermediate Similarity	NPD5473	Discontinued
0.7257	Intermediate Similarity	NPD7824	Approved
0.7255	Intermediate Similarity	NPD5809	Phase 3
0.7255	Intermediate Similarity	NPD7026	Phase 2
0.725	Intermediate Similarity	NPD3506	Approved
0.725	Intermediate Similarity	NPD3505	Approved
0.7249	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5475	Discontinued
0.7233	Intermediate Similarity	NPD4499	Approved
0.7227	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7027	Phase 3
0.7214	Intermediate Similarity	NPD8386	Phase 2
0.7212	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6210	Phase 3
0.7204	Intermediate Similarity	NPD7308	Discontinued
0.7198	Intermediate Similarity	NPD2336	Approved
0.7196	Intermediate Similarity	NPD3947	Discontinued
0.7196	Intermediate Similarity	NPD7208	Approved
0.7196	Intermediate Similarity	NPD7209	Approved
0.7196	Intermediate Similarity	NPD7207	Approved
0.7195	Intermediate Similarity	NPD6470	Phase 3
0.7192	Intermediate Similarity	NPD3320	Approved
0.7192	Intermediate Similarity	NPD3319	Phase 1
0.7192	Intermediate Similarity	NPD3318	Approved
0.719	Intermediate Similarity	NPD7948	Phase 1
0.7182	Intermediate Similarity	NPD3353	Approved
0.7178	Intermediate Similarity	NPD2479	Phase 3
0.7178	Intermediate Similarity	NPD2481	Approved
0.7177	Intermediate Similarity	NPD5855	Phase 3
0.7177	Intermediate Similarity	NPD5853	Phase 3
0.7176	Intermediate Similarity	NPD6487	Approved
0.7176	Intermediate Similarity	NPD6486	Approved
0.7171	Intermediate Similarity	NPD6217	Discontinued
0.7167	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7001	Phase 3
0.7161	Intermediate Similarity	NPD4558	Phase 2
0.7157	Intermediate Similarity	NPD6178	Phase 3
0.7156	Intermediate Similarity	NPD7269	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4883	Approved
0.7149	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD3805	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD2813	Phase 3
0.7143	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5001	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3178	Discontinued
0.7136	Intermediate Similarity	NPD6481	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7711	Discontinued
0.7123	Intermediate Similarity	NPD5854	Approved
0.7103	Intermediate Similarity	NPD6268	Phase 1
0.7103	Intermediate Similarity	NPD3775	Approved
0.7103	Intermediate Similarity	NPD2879	Approved
0.7103	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2881	Approved
0.7103	Intermediate Similarity	NPD3773	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