NPASS Compound

Structure

NPC470498 OpenBabel07101719242D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6648 1.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3339 0.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6867 1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0249 -0.1285 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 3.5686 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -0.3364 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 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 3 0 0 0 0 0 0 0 0 0 4.5468 -1.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -0.0000 -2.7321 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 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 10 2 0 0 0 0 5 11 2 0 0 0 0 6 9 1 0 0 0 0 6 12 2 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 15 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.11
Volume:	292.023
LogP:	1.069
LogD:	0.88
LogS:	-2.121
# Rotatable Bonds:	4
TPSA:	103.78
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	3.683
Fsp3:	0.267
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:	-4.727
MDCK Permeability:	6.22037487119087e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.067
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.842

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	55.82167434692383%
Volume Distribution (VD):	0.726
Pgp-substrate:	39.917518615722656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.416
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.661
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.862

ADMET: Excretion

Clearance (CL):	5.987
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.171
Carcinogencity:	0.114
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC470498

Natural Product ID:	NPC470498
*Common Name:**	Oidioperazine C
IUPAC Name:	(6Z)-3-(hydroxymethyl)-6-(1H-indol-3-ylmethylidene)-3-methoxypiperazine-2,5-dione
Synonyms:	Oidioperazine C
Standard InCHIKey:	QPYZUFUUNHUIIL-SDQBBNPISA-N
Standard InCHI:	InChI=1S/C15H15N3O4/c1-22-15(8-19)14(21)17-12(13(20)18-15)6-9-7-16-11-5-3-2-4-10(9)11/h2-7,16,19H,8H2,1H3,(H,17,21)(H,18,20)/b12-6-
SMILES:	COC1(C(=O)NC(=CC2=CNC3=CC=CC=C32)C(=O)N1)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047547
PubChem CID:	59051752
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids 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
NPO5778	Oidiodendron truncatum	Species	Myxotrichaceae	Eukaryota	n.a.	Antarctic	n.a.	PMID[22583079]
NPO5778	Oidiodendron truncatum	Species	Myxotrichaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[523445]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[523445]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[523445]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[523445]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[523445]

☑ 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 NPC470498 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	330
0.1-0.2	3292
0.2-0.3	14914
0.3-0.4	16480
0.4-0.5	3589
0.5-0.6	2104
0.6-0.7	1451
0.7-0.8	450
0.8-0.85	70
0.85-0.9	16
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8831	High Similarity	NPC159856
0.8827	High Similarity	NPC54988
0.8797	High Similarity	NPC471458
0.8726	High Similarity	NPC24678
0.8726	High Similarity	NPC105818
0.871	High Similarity	NPC314372
0.8704	High Similarity	NPC40779
0.8701	High Similarity	NPC190296
0.8679	High Similarity	NPC470507
0.8642	High Similarity	NPC282231
0.8589	High Similarity	NPC311276
0.858	High Similarity	NPC473320
0.858	High Similarity	NPC279918
0.8571	High Similarity	NPC469762
0.8521	High Similarity	NPC215795
0.8521	High Similarity	NPC176199
0.8509	High Similarity	NPC469785
0.8485	Intermediate Similarity	NPC474561
0.8485	Intermediate Similarity	NPC49954
0.8476	Intermediate Similarity	NPC102423
0.8462	Intermediate Similarity	NPC68354
0.8428	Intermediate Similarity	NPC37548
0.8405	Intermediate Similarity	NPC135141
0.8405	Intermediate Similarity	NPC92796
0.8385	Intermediate Similarity	NPC469786
0.8385	Intermediate Similarity	NPC469760
0.8385	Intermediate Similarity	NPC469763
0.8385	Intermediate Similarity	NPC259644
0.8385	Intermediate Similarity	NPC469765
0.8385	Intermediate Similarity	NPC25008
0.8385	Intermediate Similarity	NPC73952
0.8377	Intermediate Similarity	NPC84911
0.8372	Intermediate Similarity	NPC163055
0.8365	Intermediate Similarity	NPC471957
0.8354	Intermediate Similarity	NPC131718
0.8343	Intermediate Similarity	NPC275305
0.8343	Intermediate Similarity	NPC37423
0.8333	Intermediate Similarity	NPC80597
0.8333	Intermediate Similarity	NPC212376
0.8333	Intermediate Similarity	NPC211572
0.8333	Intermediate Similarity	NPC75540
0.8333	Intermediate Similarity	NPC70922
0.8323	Intermediate Similarity	NPC63751
0.8312	Intermediate Similarity	NPC96102
0.8312	Intermediate Similarity	NPC29886
0.8312	Intermediate Similarity	NPC261195
0.8293	Intermediate Similarity	NPC230869
0.8291	Intermediate Similarity	NPC242556
0.8284	Intermediate Similarity	NPC313791
0.8276	Intermediate Similarity	NPC188387
0.8276	Intermediate Similarity	NPC163421
0.8269	Intermediate Similarity	NPC73767
0.8269	Intermediate Similarity	NPC110126
0.8263	Intermediate Similarity	NPC49217
0.8263	Intermediate Similarity	NPC160105
0.8258	Intermediate Similarity	NPC105127
0.8253	Intermediate Similarity	NPC194640
0.8221	Intermediate Similarity	NPC38736
0.8217	Intermediate Similarity	NPC469768
0.8217	Intermediate Similarity	NPC469783
0.8217	Intermediate Similarity	NPC469761
0.8217	Intermediate Similarity	NPC469767
0.8217	Intermediate Similarity	NPC469780
0.8217	Intermediate Similarity	NPC469779
0.8217	Intermediate Similarity	NPC469784
0.8214	Intermediate Similarity	NPC201700
0.8199	Intermediate Similarity	NPC187951
0.8198	Intermediate Similarity	NPC270009
0.8187	Intermediate Similarity	NPC143872
0.8177	Intermediate Similarity	NPC470499
0.8166	Intermediate Similarity	NPC194411
0.8165	Intermediate Similarity	NPC469766
0.8161	Intermediate Similarity	NPC469358
0.8161	Intermediate Similarity	NPC48938
0.814	Intermediate Similarity	NPC248454
0.8101	Intermediate Similarity	NPC279081
0.8098	Intermediate Similarity	NPC216713
0.8092	Intermediate Similarity	NPC11126
0.8087	Intermediate Similarity	NPC470497
0.8086	Intermediate Similarity	NPC124005
0.807	Intermediate Similarity	NPC34508
0.807	Intermediate Similarity	NPC314603
0.8068	Intermediate Similarity	NPC280290
0.8061	Intermediate Similarity	NPC141353
0.8057	Intermediate Similarity	NPC472444
0.8052	Intermediate Similarity	NPC82295
0.8035	Intermediate Similarity	NPC59269
0.8035	Intermediate Similarity	NPC151939
0.8	Intermediate Similarity	NPC233936
0.7989	Intermediate Similarity	NPC472443
0.7987	Intermediate Similarity	NPC230002
0.7987	Intermediate Similarity	NPC22079
0.7975	Intermediate Similarity	NPC321911
0.7963	Intermediate Similarity	NPC288838
0.7943	Intermediate Similarity	NPC300688
0.7939	Intermediate Similarity	NPC200214
0.7927	Intermediate Similarity	NPC53947
0.7914	Intermediate Similarity	NPC179787
0.7914	Intermediate Similarity	NPC201380
0.7914	Intermediate Similarity	NPC469811
0.7912	Intermediate Similarity	NPC294693
0.791	Intermediate Similarity	NPC228835
0.7874	Intermediate Similarity	NPC267885
0.7865	Intermediate Similarity	NPC314002
0.7857	Intermediate Similarity	NPC318065
0.7857	Intermediate Similarity	NPC206819
0.7853	Intermediate Similarity	NPC63545
0.7853	Intermediate Similarity	NPC129042
0.7844	Intermediate Similarity	NPC285469
0.7844	Intermediate Similarity	NPC184476
0.7833	Intermediate Similarity	NPC46413
0.7821	Intermediate Similarity	NPC315555
0.7821	Intermediate Similarity	NPC256893
0.7821	Intermediate Similarity	NPC235684
0.7816	Intermediate Similarity	NPC110500
0.7816	Intermediate Similarity	NPC149155
0.7816	Intermediate Similarity	NPC203468
0.7814	Intermediate Similarity	NPC133366
0.7809	Intermediate Similarity	NPC204717
0.7809	Intermediate Similarity	NPC284678
0.7803	Intermediate Similarity	NPC6982
0.7802	Intermediate Similarity	NPC477166
0.7802	Intermediate Similarity	NPC304187
0.7798	Intermediate Similarity	NPC299594
0.7797	Intermediate Similarity	NPC71037
0.7797	Intermediate Similarity	NPC192270
0.7791	Intermediate Similarity	NPC78020
0.7784	Intermediate Similarity	NPC248041
0.7784	Intermediate Similarity	NPC283219
0.7784	Intermediate Similarity	NPC126709
0.7778	Intermediate Similarity	NPC317030
0.7771	Intermediate Similarity	NPC470823
0.7765	Intermediate Similarity	NPC62510
0.776	Intermediate Similarity	NPC474177
0.7753	Intermediate Similarity	NPC220765
0.7737	Intermediate Similarity	NPC46225
0.7736	Intermediate Similarity	NPC325252
0.7727	Intermediate Similarity	NPC293472
0.7725	Intermediate Similarity	NPC141926
0.7725	Intermediate Similarity	NPC325903
0.7722	Intermediate Similarity	NPC171171
0.7722	Intermediate Similarity	NPC474707
0.772	Intermediate Similarity	NPC207020
0.7719	Intermediate Similarity	NPC472587
0.7714	Intermediate Similarity	NPC472586
0.7713	Intermediate Similarity	NPC476874
0.7706	Intermediate Similarity	NPC122141
0.7697	Intermediate Similarity	NPC243381
0.7697	Intermediate Similarity	NPC275292
0.7696	Intermediate Similarity	NPC127677
0.7692	Intermediate Similarity	NPC95783
0.7692	Intermediate Similarity	NPC286427
0.7692	Intermediate Similarity	NPC236711
0.7688	Intermediate Similarity	NPC125746
0.7684	Intermediate Similarity	NPC233050
0.7684	Intermediate Similarity	NPC213468
0.7684	Intermediate Similarity	NPC276540
0.768	Intermediate Similarity	NPC17059
0.768	Intermediate Similarity	NPC46580
0.768	Intermediate Similarity	NPC204565
0.7679	Intermediate Similarity	NPC477815
0.7679	Intermediate Similarity	NPC34844
0.7676	Intermediate Similarity	NPC251090
0.7674	Intermediate Similarity	NPC470508
0.7673	Intermediate Similarity	NPC198988
0.767	Intermediate Similarity	NPC288785
0.7667	Intermediate Similarity	NPC15102
0.7661	Intermediate Similarity	NPC16667
0.766	Intermediate Similarity	NPC300183
0.7647	Intermediate Similarity	NPC56765
0.7647	Intermediate Similarity	NPC41257
0.764	Intermediate Similarity	NPC24864
0.7637	Intermediate Similarity	NPC65215
0.7637	Intermediate Similarity	NPC173028
0.7624	Intermediate Similarity	NPC94752
0.7619	Intermediate Similarity	NPC193761
0.7616	Intermediate Similarity	NPC271734
0.7611	Intermediate Similarity	NPC165495
0.7609	Intermediate Similarity	NPC99666
0.7598	Intermediate Similarity	NPC314394
0.7588	Intermediate Similarity	NPC216643
0.7584	Intermediate Similarity	NPC55772
0.7584	Intermediate Similarity	NPC42979
0.7581	Intermediate Similarity	NPC242209
0.7579	Intermediate Similarity	NPC98715
0.7576	Intermediate Similarity	NPC470440
0.7574	Intermediate Similarity	NPC207726
0.7572	Intermediate Similarity	NPC42372
0.7572	Intermediate Similarity	NPC17751
0.7572	Intermediate Similarity	NPC280864
0.7571	Intermediate Similarity	NPC224764
0.7568	Intermediate Similarity	NPC307963
0.756	Intermediate Similarity	NPC470233
0.7553	Intermediate Similarity	NPC32200
0.7552	Intermediate Similarity	NPC225821
0.7551	Intermediate Similarity	NPC313640
0.7541	Intermediate Similarity	NPC213629
0.7539	Intermediate Similarity	NPC470500
0.7538	Intermediate Similarity	NPC151976
0.7528	Intermediate Similarity	NPC145885

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 NPC470498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	628
0.2-0.3	910
0.3-0.4	1511
0.4-0.5	2855
0.5-0.6	2121
0.6-0.7	805
0.7-0.8	136
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8659	High Similarity	NPD5069	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3506	Approved
0.8462	Intermediate Similarity	NPD3505	Approved
0.8412	Intermediate Similarity	NPD4079	Approved
0.8412	Intermediate Similarity	NPD4076	Approved
0.8312	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD786	Approved
0.8199	Intermediate Similarity	NPD3100	Discontinued
0.8166	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1722	Approved
0.8148	Intermediate Similarity	NPD4463	Approved
0.8148	Intermediate Similarity	NPD4462	Approved
0.8086	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD6595	Phase 3
0.8035	Intermediate Similarity	NPD2144	Approved
0.8023	Intermediate Similarity	NPD5065	Approved
0.7898	Intermediate Similarity	NPD3038	Discontinued
0.7895	Intermediate Similarity	NPD4640	Approved
0.7895	Intermediate Similarity	NPD4638	Approved
0.7895	Intermediate Similarity	NPD4639	Approved
0.7874	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD2172	Phase 1
0.7816	Intermediate Similarity	NPD4128	Approved
0.7816	Intermediate Similarity	NPD482	Approved
0.7753	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD1403	Approved
0.7706	Intermediate Similarity	NPD1404	Approved
0.7688	Intermediate Similarity	NPD5021	Discontinued
0.768	Intermediate Similarity	NPD3961	Discontinued
0.768	Intermediate Similarity	NPD8431	Approved
0.767	Intermediate Similarity	NPD4075	Phase 2
0.7663	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2092	Phase 2
0.7654	Intermediate Similarity	NPD2095	Phase 2
0.7654	Intermediate Similarity	NPD2094	Phase 2
0.7637	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7948	Phase 1
0.7619	Intermediate Similarity	NPD2837	Discontinued
0.7611	Intermediate Similarity	NPD2091	Phase 2
0.7611	Intermediate Similarity	NPD2096	Phase 2
0.7604	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD5612	Discontinued
0.7586	Intermediate Similarity	NPD2640	Approved
0.7586	Intermediate Similarity	NPD2641	Approved
0.7577	Intermediate Similarity	NPD5067	Phase 2
0.7577	Intermediate Similarity	NPD5066	Phase 2
0.7569	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1038	Approved
0.7568	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD750	Phase 2
0.7543	Intermediate Similarity	NPD1325	Approved
0.7543	Intermediate Similarity	NPD1326	Approved
0.7529	Intermediate Similarity	NPD2639	Approved
0.7529	Intermediate Similarity	NPD2642	Approved
0.7528	Intermediate Similarity	NPD4181	Approved
0.7514	Intermediate Similarity	NPD3323	Discontinued
0.75	Intermediate Similarity	NPD1592	Phase 3
0.7486	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD1392	Approved
0.7459	Intermediate Similarity	NPD5596	Phase 2
0.7439	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7957	Phase 1
0.7401	Intermediate Similarity	NPD3117	Approved
0.7401	Intermediate Similarity	NPD3116	Approved
0.7396	Intermediate Similarity	NPD3833	Phase 3
0.7396	Intermediate Similarity	NPD8072	Approved
0.7396	Intermediate Similarity	NPD3835	Phase 3
0.7396	Intermediate Similarity	NPD5487	Phase 1
0.7389	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD802	Phase 2
0.7368	Intermediate Similarity	NPD6249	Phase 2
0.7368	Intermediate Similarity	NPD6248	Phase 2
0.7356	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD8073	Approved
0.7342	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD991	Phase 2
0.734	Intermediate Similarity	NPD7619	Phase 3
0.734	Intermediate Similarity	NPD7618	Phase 3
0.7337	Intermediate Similarity	NPD706	Phase 1
0.7337	Intermediate Similarity	NPD6217	Discontinued
0.733	Intermediate Similarity	NPD484	Approved
0.7322	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7470	Discontinued
0.7305	Intermediate Similarity	NPD5254	Discontinued
0.7303	Intermediate Similarity	NPD3610	Approved
0.7303	Intermediate Similarity	NPD3609	Approved
0.7283	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1661	Suspended
0.7273	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2720	Phase 1
0.7268	Intermediate Similarity	NPD5901	Discontinued
0.7268	Intermediate Similarity	NPD8272	Phase 2
0.7246	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5255	Approved
0.7234	Intermediate Similarity	NPD4615	Phase 2
0.7222	Intermediate Similarity	NPD2928	Phase 2
0.7216	Intermediate Similarity	NPD5140	Approved
0.7216	Intermediate Similarity	NPD5138	Approved
0.7205	Intermediate Similarity	NPD3475	Approved
0.7205	Intermediate Similarity	NPD3476	Approved
0.7191	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3825	Phase 3
0.7184	Intermediate Similarity	NPD2581	Approved
0.7184	Intermediate Similarity	NPD2582	Approved
0.7182	Intermediate Similarity	NPD2380	Approved
0.7182	Intermediate Similarity	NPD2381	Approved
0.7182	Intermediate Similarity	NPD2382	Approved
0.7181	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4702	Approved
0.7176	Intermediate Similarity	NPD4547	Phase 3
0.7176	Intermediate Similarity	NPD4703	Approved
0.7174	Intermediate Similarity	NPD5105	Approved
0.7174	Intermediate Similarity	NPD5106	Approved
0.7173	Intermediate Similarity	NPD6206	Phase 1
0.7172	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5897	Approved
0.7158	Intermediate Similarity	NPD5899	Approved
0.7158	Intermediate Similarity	NPD5898	Approved
0.7158	Intermediate Similarity	NPD7944	Discontinued
0.7152	Intermediate Similarity	NPD1262	Discovery
0.7151	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7558	Phase 2
0.7143	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3404	Approved
0.7143	Intermediate Similarity	NPD8122	Approved
0.7143	Intermediate Similarity	NPD3654	Approved
0.7143	Intermediate Similarity	NPD3003	Approved
0.7143	Intermediate Similarity	NPD2006	Phase 2
0.7143	Intermediate Similarity	NPD8123	Approved
0.7135	Intermediate Similarity	NPD4957	Phase 2
0.7135	Intermediate Similarity	NPD2430	Phase 2
0.7128	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2119	Approved
0.7125	Intermediate Similarity	NPD2118	Approved
0.7118	Intermediate Similarity	NPD1683	Approved
0.7118	Intermediate Similarity	NPD7469	Discontinued
0.7114	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3330	Phase 1
0.7098	Intermediate Similarity	NPD1768	Approved
0.7098	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6664	Approved
0.7083	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2915	Discontinued
0.7079	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3385	Approved
0.7072	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2509	Approved
0.7071	Intermediate Similarity	NPD2510	Approved
0.7062	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1248	Discontinued
0.7037	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6281	Approved
0.7035	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1183	Approved
0.7029	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2580	Discontinued
0.7026	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD8093	Discontinued
0.7011	Intermediate Similarity	NPD8386	Phase 2
0.701	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4699	Discontinued
0.7	Intermediate Similarity	NPD5862	Discovery
0.6995	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4326	Phase 2
0.6984	Remote Similarity	NPD4334	Discontinued
0.6982	Remote Similarity	NPD5020	Approved
0.6971	Remote Similarity	NPD2165	Phase 1
0.697	Remote Similarity	NPD4029	Approved
0.697	Remote Similarity	NPD4028	Approved
0.697	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4030	Approved
0.6966	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6261	Phase 3

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