NPASS Compound

Structure

NPC470497 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2040 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6580 1.3965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2054 0.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1133 2.2352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 0.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5166 2.4360 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 -1.6730 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6607 1.2919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1147 2.1829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 3 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 -2.4076 2.8900 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 2.5981 -1.5000 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 0.1305 1.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 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 15 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 12 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 1 0 0 0 0 13 20 2 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 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	319.12
Volume:	303.45
LogP:	0.599
LogD:	0.974
LogS:	-2.158
# Rotatable Bonds:	4
TPSA:	114.89
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.594
Synthetic Accessibility Score:	3.752
Fsp3:	0.333
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:	-4.966
MDCK Permeability:	4.601232831191737e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.35
Human Intestinal Absorption (HIA):	0.194
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.552

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.854
Plasma Protein Binding (PPB):	13.831907272338867%
Volume Distribution (VD):	0.499
Pgp-substrate:	73.73818969726562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.417
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.435
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.591
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	3.86
Half-life (T1/2):	0.814

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.371
Rat Oral Acute Toxicity:	0.577
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.184
Carcinogencity:	0.764
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.189

Download Data

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

Natural Product: NPC470497

Natural Product ID:	NPC470497
*Common Name:**	Oidioperazine B
IUPAC Name:	6-hydroxy-3-(hydroxymethyl)-6-(1H-indol-3-ylmethyl)-1-methoxypiperazine-2,5-dione
Synonyms:	Oidioperazine B
Standard InCHIKey:	SXFOZGYJEJAZDJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H17N3O5/c1-23-18-13(20)12(8-19)17-14(21)15(18,22)6-9-7-16-11-5-3-2-4-10(9)11/h2-5,7,12,16,19,22H,6,8H2,1H3,(H,17,21)
SMILES:	CON1C(=O)C(NC(=O)C1(CC2=CNC3=CC=CC=C32)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047545
PubChem CID:	59051751
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[465159]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[465159]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[465159]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[465159]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[465159]

☑ 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 NPC470497 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	310
0.1-0.2	2909
0.2-0.3	14541
0.3-0.4	17096
0.4-0.5	3104
0.5-0.6	2637
0.6-0.7	1484
0.7-0.8	575
0.8-0.85	37
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9341	High Similarity	NPC470499
0.8785	High Similarity	NPC165495
0.8624	High Similarity	NPC473640
0.8586	High Similarity	NPC475506
0.8542	High Similarity	NPC155143
0.8427	Intermediate Similarity	NPC54988
0.8396	Intermediate Similarity	NPC213629
0.8385	Intermediate Similarity	NPC100321
0.8362	Intermediate Similarity	NPC282231
0.8324	Intermediate Similarity	NPC474561
0.8324	Intermediate Similarity	NPC49954
0.8305	Intermediate Similarity	NPC279918
0.8283	Intermediate Similarity	NPC107077
0.8283	Intermediate Similarity	NPC223791
0.828	Intermediate Similarity	NPC228835
0.8261	Intermediate Similarity	NPC11126
0.8249	Intermediate Similarity	NPC230869
0.8245	Intermediate Similarity	NPC17059
0.8226	Intermediate Similarity	NPC469358
0.8196	Intermediate Similarity	NPC293917
0.8191	Intermediate Similarity	NPC94752
0.8191	Intermediate Similarity	NPC315555
0.8177	Intermediate Similarity	NPC63751
0.8138	Intermediate Similarity	NPC15102
0.8138	Intermediate Similarity	NPC163421
0.8138	Intermediate Similarity	NPC188387
0.8122	Intermediate Similarity	NPC160105
0.8115	Intermediate Similarity	NPC117244
0.8115	Intermediate Similarity	NPC473763
0.8111	Intermediate Similarity	NPC194640
0.8087	Intermediate Similarity	NPC470498
0.8075	Intermediate Similarity	NPC71037
0.8065	Intermediate Similarity	NPC126709
0.8065	Intermediate Similarity	NPC248041
0.8065	Intermediate Similarity	NPC283219
0.8054	Intermediate Similarity	NPC267885
0.8051	Intermediate Similarity	NPC171317
0.8043	Intermediate Similarity	NPC314603
0.8032	Intermediate Similarity	NPC163055
0.802	Intermediate Similarity	NPC320968
0.8011	Intermediate Similarity	NPC311276
0.8011	Intermediate Similarity	NPC40779
0.801	Intermediate Similarity	NPC478158
0.801	Intermediate Similarity	NPC162860
0.8	Intermediate Similarity	NPC472586
0.8	Intermediate Similarity	NPC235684
0.8	Intermediate Similarity	NPC54420
0.8	Intermediate Similarity	NPC149155
0.8	Intermediate Similarity	NPC203468
0.8	Intermediate Similarity	NPC110500
0.799	Intermediate Similarity	NPC478157
0.7989	Intermediate Similarity	NPC469762
0.798	Intermediate Similarity	NPC75634
0.798	Intermediate Similarity	NPC476874
0.7979	Intermediate Similarity	NPC233936
0.7969	Intermediate Similarity	NPC95783
0.7968	Intermediate Similarity	NPC472443
0.7937	Intermediate Similarity	NPC48938
0.7934	Intermediate Similarity	NPC89987
0.7933	Intermediate Similarity	NPC469785
0.7927	Intermediate Similarity	NPC243716
0.7914	Intermediate Similarity	NPC145885
0.7914	Intermediate Similarity	NPC14113
0.7914	Intermediate Similarity	NPC59269
0.7914	Intermediate Similarity	NPC248454
0.7914	Intermediate Similarity	NPC84827
0.7912	Intermediate Similarity	NPC102423
0.7897	Intermediate Similarity	NPC294693
0.7889	Intermediate Similarity	NPC193761
0.7874	Intermediate Similarity	NPC281049
0.7871	Intermediate Similarity	NPC314957
0.7853	Intermediate Similarity	NPC62510
0.7849	Intermediate Similarity	NPC313791
0.7842	Intermediate Similarity	NPC472444
0.7833	Intermediate Similarity	NPC285469
0.7831	Intermediate Similarity	NPC91179
0.7821	Intermediate Similarity	NPC469786
0.7821	Intermediate Similarity	NPC73952
0.7821	Intermediate Similarity	NPC469763
0.7821	Intermediate Similarity	NPC469760
0.7821	Intermediate Similarity	NPC469765
0.7821	Intermediate Similarity	NPC259644
0.7821	Intermediate Similarity	NPC25008
0.7819	Intermediate Similarity	NPC111275
0.7819	Intermediate Similarity	NPC68354
0.7811	Intermediate Similarity	NPC473376
0.7804	Intermediate Similarity	NPC475859
0.7804	Intermediate Similarity	NPC474877
0.7804	Intermediate Similarity	NPC475969
0.7802	Intermediate Similarity	NPC131718
0.7789	Intermediate Similarity	NPC314394
0.7788	Intermediate Similarity	NPC477714
0.7784	Intermediate Similarity	NPC78020
0.7784	Intermediate Similarity	NPC201700
0.7784	Intermediate Similarity	NPC317430
0.7784	Intermediate Similarity	NPC154339
0.7783	Intermediate Similarity	NPC24370
0.7783	Intermediate Similarity	NPC319232
0.7783	Intermediate Similarity	NPC127677
0.7778	Intermediate Similarity	NPC219336
0.7778	Intermediate Similarity	NPC211572
0.7778	Intermediate Similarity	NPC70922
0.7778	Intermediate Similarity	NPC80597
0.7778	Intermediate Similarity	NPC270009
0.7778	Intermediate Similarity	NPC471192
0.7778	Intermediate Similarity	NPC212376
0.7778	Intermediate Similarity	NPC75540
0.7773	Intermediate Similarity	NPC64216
0.7772	Intermediate Similarity	NPC317030
0.7767	Intermediate Similarity	NPC54744
0.7757	Intermediate Similarity	NPC470729
0.7757	Intermediate Similarity	NPC477175
0.7757	Intermediate Similarity	NPC477176
0.7757	Intermediate Similarity	NPC470730
0.7755	Intermediate Similarity	NPC267343
0.774	Intermediate Similarity	NPC472285
0.774	Intermediate Similarity	NPC477715
0.7734	Intermediate Similarity	NPC323927
0.7734	Intermediate Similarity	NPC46225
0.7732	Intermediate Similarity	NPC321708
0.7731	Intermediate Similarity	NPC63279
0.7725	Intermediate Similarity	NPC15573
0.7725	Intermediate Similarity	NPC183662
0.7725	Intermediate Similarity	NPC217372
0.7725	Intermediate Similarity	NPC151939
0.7721	Intermediate Similarity	NPC477177
0.772	Intermediate Similarity	NPC474707
0.7718	Intermediate Similarity	NPC151976
0.7713	Intermediate Similarity	NPC275305
0.7713	Intermediate Similarity	NPC37423
0.7696	Intermediate Similarity	NPC297642
0.7692	Intermediate Similarity	NPC204491
0.7685	Intermediate Similarity	NPC165743
0.7684	Intermediate Similarity	NPC314372
0.768	Intermediate Similarity	NPC204565
0.7663	Intermediate Similarity	NPC16667
0.7662	Intermediate Similarity	NPC300183
0.766	Intermediate Similarity	NPC472123
0.766	Intermediate Similarity	NPC34508
0.7659	Intermediate Similarity	NPC271862
0.765	Intermediate Similarity	NPC323752
0.7644	Intermediate Similarity	NPC469896
0.7641	Intermediate Similarity	NPC65215
0.7641	Intermediate Similarity	NPC173028
0.7637	Intermediate Similarity	NPC141353
0.7633	Intermediate Similarity	NPC75726
0.7633	Intermediate Similarity	NPC6865
0.7633	Intermediate Similarity	NPC153980
0.7633	Intermediate Similarity	NPC31385
0.7633	Intermediate Similarity	NPC110602
0.7629	Intermediate Similarity	NPC62749
0.7621	Intermediate Similarity	NPC5145
0.7617	Intermediate Similarity	NPC284678
0.7612	Intermediate Similarity	NPC23420
0.7612	Intermediate Similarity	NPC303820
0.7612	Intermediate Similarity	NPC205254
0.7612	Intermediate Similarity	NPC106771
0.761	Intermediate Similarity	NPC258062
0.7596	Intermediate Similarity	NPC229348
0.7592	Intermediate Similarity	NPC55772
0.7592	Intermediate Similarity	NPC133261
0.7592	Intermediate Similarity	NPC213468
0.759	Intermediate Similarity	NPC46580
0.7588	Intermediate Similarity	NPC11445
0.7586	Intermediate Similarity	NPC98715
0.7585	Intermediate Similarity	NPC72956
0.7582	Intermediate Similarity	NPC207726
0.7581	Intermediate Similarity	NPC470508
0.7577	Intermediate Similarity	NPC314002
0.7576	Intermediate Similarity	NPC474177
0.7574	Intermediate Similarity	NPC475935
0.7574	Intermediate Similarity	NPC94211
0.7574	Intermediate Similarity	NPC52909
0.7571	Intermediate Similarity	NPC79386
0.7571	Intermediate Similarity	NPC190296
0.7565	Intermediate Similarity	NPC472108
0.7565	Intermediate Similarity	NPC139291
0.7561	Intermediate Similarity	NPC88008
0.7561	Intermediate Similarity	NPC225821
0.756	Intermediate Similarity	NPC313640
0.7553	Intermediate Similarity	NPC194411
0.7552	Intermediate Similarity	NPC300688
0.7551	Intermediate Similarity	NPC175474
0.755	Intermediate Similarity	NPC156704
0.755	Intermediate Similarity	NPC262898
0.7548	Intermediate Similarity	NPC471194
0.7548	Intermediate Similarity	NPC207020
0.7548	Intermediate Similarity	NPC87856
0.7548	Intermediate Similarity	NPC471193
0.7538	Intermediate Similarity	NPC157828
0.7538	Intermediate Similarity	NPC133366
0.7538	Intermediate Similarity	NPC195239
0.7538	Intermediate Similarity	NPC171171
0.7526	Intermediate Similarity	NPC469938
0.7526	Intermediate Similarity	NPC204717
0.7525	Intermediate Similarity	NPC45459
0.7525	Intermediate Similarity	NPC315491
0.7524	Intermediate Similarity	NPC132211
0.7524	Intermediate Similarity	NPC203614
0.7512	Intermediate Similarity	NPC212213

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 NPC470497 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	543
0.2-0.3	908
0.3-0.4	1692
0.4-0.5	2602
0.5-0.6	2263
0.6-0.7	853
0.7-0.8	114
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8232	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8196	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8173	Intermediate Similarity	NPD8272	Phase 2
0.8032	Intermediate Similarity	NPD2095	Phase 2
0.8032	Intermediate Similarity	NPD2092	Phase 2
0.8032	Intermediate Similarity	NPD2094	Phase 2
0.8	Intermediate Similarity	NPD482	Approved
0.7989	Intermediate Similarity	NPD2091	Phase 2
0.7989	Intermediate Similarity	NPD2096	Phase 2
0.7957	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD6595	Phase 3
0.7872	Intermediate Similarity	NPD4079	Approved
0.7872	Intermediate Similarity	NPD4076	Approved
0.7842	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD3505	Approved
0.7819	Intermediate Similarity	NPD3506	Approved
0.7806	Intermediate Similarity	NPD7944	Discontinued
0.7794	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7470	Discontinued
0.7754	Intermediate Similarity	NPD750	Phase 2
0.774	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD3961	Discontinued
0.7602	Intermediate Similarity	NPD3321	Discontinued
0.7598	Intermediate Similarity	NPD7957	Phase 1
0.7598	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD8431	Approved
0.7586	Intermediate Similarity	NPD8072	Approved
0.7561	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD2144	Approved
0.7537	Intermediate Similarity	NPD8073	Approved
0.7536	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5065	Approved
0.7525	Intermediate Similarity	NPD484	Approved
0.7512	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5487	Phase 1
0.7488	Intermediate Similarity	NPD7271	Approved
0.7487	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4075	Phase 2
0.7487	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD1392	Approved
0.7476	Intermediate Similarity	NPD8322	Phase 2
0.7464	Intermediate Similarity	NPD8093	Discontinued
0.7463	Intermediate Similarity	NPD7948	Phase 1
0.7463	Intermediate Similarity	NPD5426	Phase 3
0.746	Intermediate Similarity	NPD1326	Approved
0.746	Intermediate Similarity	NPD1325	Approved
0.7454	Intermediate Similarity	NPD7711	Discontinued
0.7454	Intermediate Similarity	NPD7603	Discontinued
0.745	Intermediate Similarity	NPD7618	Phase 3
0.745	Intermediate Similarity	NPD7619	Phase 3
0.7448	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3038	Discontinued
0.7419	Intermediate Similarity	NPD7730	Approved
0.7419	Intermediate Similarity	NPD7731	Approved
0.7416	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4640	Approved
0.7407	Intermediate Similarity	NPD4639	Approved
0.7407	Intermediate Similarity	NPD4638	Approved
0.7402	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD786	Approved
0.74	Intermediate Similarity	NPD802	Phase 2
0.74	Intermediate Similarity	NPD1038	Approved
0.74	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6248	Phase 2
0.7389	Intermediate Similarity	NPD6249	Phase 2
0.7379	Intermediate Similarity	NPD5901	Discontinued
0.7358	Intermediate Similarity	NPD5612	Discontinued
0.7353	Intermediate Similarity	NPD4601	Approved
0.7353	Intermediate Similarity	NPD4600	Approved
0.7352	Intermediate Similarity	NPD7824	Approved
0.7343	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7970	Approved
0.7311	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7781	Approved
0.7306	Intermediate Similarity	NPD7780	Approved
0.7295	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD6206	Phase 1
0.7291	Intermediate Similarity	NPD5003	Discontinued
0.7282	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4427	Phase 2
0.7268	Intermediate Similarity	NPD3100	Discontinued
0.726	Intermediate Similarity	NPD7001	Phase 3
0.7254	Intermediate Similarity	NPD4128	Approved
0.7252	Intermediate Similarity	NPD7790	Approved
0.7252	Intermediate Similarity	NPD7950	Approved
0.7252	Intermediate Similarity	NPD7791	Approved
0.7252	Intermediate Similarity	NPD7789	Approved
0.7252	Intermediate Similarity	NPD7953	Approved
0.7252	Intermediate Similarity	NPD7951	Approved
0.7252	Intermediate Similarity	NPD7952	Approved
0.7241	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2511	Approved
0.7232	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1722	Approved
0.7213	Intermediate Similarity	NPD4702	Approved
0.7213	Intermediate Similarity	NPD4703	Approved
0.7204	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6173	Approved
0.7198	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD706	Phase 1
0.7183	Intermediate Similarity	NPD8094	Discontinued
0.7177	Intermediate Similarity	NPD3003	Approved
0.7174	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5066	Phase 2
0.717	Intermediate Similarity	NPD5067	Phase 2
0.7166	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2564	Approved
0.7164	Intermediate Similarity	NPD4499	Approved
0.7164	Intermediate Similarity	NPD2565	Phase 2
0.7163	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD1768	Approved
0.7135	Intermediate Similarity	NPD4463	Approved
0.7135	Intermediate Similarity	NPD4462	Approved
0.7128	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5596	Phase 2
0.7114	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD2510	Approved
0.7109	Intermediate Similarity	NPD2509	Approved
0.7103	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6217	Discontinued
0.7094	Intermediate Similarity	NPD6665	Discontinued
0.7085	Intermediate Similarity	NPD1096	Discontinued
0.7079	Intermediate Similarity	NPD5117	Phase 2
0.7075	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5140	Approved
0.7068	Intermediate Similarity	NPD5138	Approved
0.7056	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8386	Phase 2
0.7053	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8169	Discontinued
0.7047	Intermediate Similarity	NPD2844	Phase 3
0.7044	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2381	Approved
0.7041	Intermediate Similarity	NPD2380	Approved
0.7041	Intermediate Similarity	NPD2382	Approved
0.703	Intermediate Similarity	NPD4334	Discontinued
0.7024	Intermediate Similarity	NPD4602	Approved
0.7022	Intermediate Similarity	NPD7558	Phase 2
0.7009	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4181	Approved
0.7	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5255	Approved
0.6996	Remote Similarity	NPD5559	Phase 2
0.6986	Remote Similarity	NPD5017	Discontinued
0.6985	Remote Similarity	NPD3178	Discontinued
0.6982	Remote Similarity	NPD8289	Discontinued
0.6981	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6999	Discontinued
0.6967	Remote Similarity	NPD8114	Approved
0.6967	Remote Similarity	NPD8115	Approved
0.6965	Remote Similarity	NPD5555	Phase 1
0.6961	Remote Similarity	NPD5913	Phase 3
0.6961	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3393	Approved
0.6959	Remote Similarity	NPD3389	Approved
0.6959	Remote Similarity	NPD3394	Approved
0.6957	Remote Similarity	NPD6664	Approved
0.6954	Remote Similarity	NPD5100	Phase 3
0.6952	Remote Similarity	NPD2172	Phase 1
0.6951	Remote Similarity	NPD6165	Phase 2
0.6951	Remote Similarity	NPD6164	Phase 2
0.6951	Remote Similarity	NPD4086	Phase 1
0.6948	Remote Similarity	NPD7666	Phase 3
0.6948	Remote Similarity	NPD7665	Phase 2
0.694	Remote Similarity	NPD1592	Phase 3
0.6938	Remote Similarity	NPD4501	Approved
0.6938	Remote Similarity	NPD4500	Approved
0.6935	Remote Similarity	NPD6452	Discontinued
0.6931	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3404	Approved
0.6923	Remote Similarity	NPD6261	Phase 3
0.6915	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4897	Phase 2
0.6912	Remote Similarity	NPD5903	Approved
0.6912	Remote Similarity	NPD5902	Approved
0.6909	Remote Similarity	NPD6242	Discontinued
0.6905	Remote Similarity	NPD7727	Phase 2
0.6905	Remote Similarity	NPD7817	Phase 1
0.6904	Remote Similarity	NPD2928	Phase 2
0.69	Remote Similarity	NPD8408	Discontinued
0.6898	Remote Similarity	NPD4852	Phase 2
0.6898	Remote Similarity	NPD3330	Phase 1

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