NPASS Compound

Structure

NPC297642 OpenBabel07101719512D 37 42 0 0 1 0 0 0 0 0999 V2000 -2.5377 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 3.1569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2146 -1.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7172 -2.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9003 -3.6646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3319 -1.6695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7462 -3.1762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7525 -2.2758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0544 -3.1762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9819 -0.7577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7462 -2.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5417 -0.0385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3343 2.3110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3508 -0.0298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4025 -1.3639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0544 -2.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4906 -1.0139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0171 -0.6049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9003 -1.7111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -1.4438 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7259 -0.6536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3286 -1.5459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8459 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4852 0.2143 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 0.9767 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6973 -0.7557 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 -2.3110 2.3110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3062 -0.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -2.8955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 -0.4884 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3575 2.3110 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -1.8173 -0.5905 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 36 1 0 0 0 0 3 37 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 18 2 0 0 0 0 11 19 2 0 0 0 0 12 17 2 0 0 0 0 12 27 1 0 0 0 0 13 31 1 0 0 0 0 14 29 1 0 0 0 0 14 32 2 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 18 27 1 0 0 0 0 19 29 1 0 0 0 0 20 25 1 6 0 0 0 20 26 1 0 0 0 0 20 33 1 0 0 0 0 21 25 1 1 0 0 0 21 29 1 0 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 22 34 2 0 0 0 0 23 26 1 0 0 0 0 23 28 1 0 0 0 0 23 35 2 0 0 0 0 24 13 1 6 0 0 0 24 28 1 0 0 0 0 24 36 1 0 0 0 0 25 17 1 6 0 0 0 26 30 1 0 0 0 0 26 37 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.13
Volume:	505.505
LogP:	3.035
LogD:	2.21
LogS:	-4.265
# Rotatable Bonds:	5
TPSA:	117.18
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.422
Synthetic Accessibility Score:	5.094
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.55
MDCK Permeability:	5.6644234973646235e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.123
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.379
Plasma Protein Binding (PPB):	76.3869400024414%
Volume Distribution (VD):	1.401
Pgp-substrate:	18.293607711791992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.707
CYP2C19-inhibitor:	0.732
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.859
CYP2C9-substrate:	0.661
CYP2D6-inhibitor:	0.135
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.616
CYP3A4-substrate:	0.974

ADMET: Excretion

Clearance (CL):	6.402
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.873
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.883
Carcinogencity:	0.141
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC297642

Natural Product ID:	NPC297642
*Common Name:**	Oidioperazine A
IUPAC Name:	n.a.
Synonyms:	Oidioperazine A
Standard InCHIKey:	ITQAUKWLTNMHOH-WLXMOELSSA-N
Standard InCHI:	InChI=1S/C26H26N4O5S2/c1-28-23(35)26(37-3)20(33)25(17-12-27-18-10-6-4-8-15(17)18)16-9-5-7-11-19(16)29(14-32)21(25)30(26)22(34)24(28,13-31)36-2/h4-12,14,20-21,27,31,33H,13H2,1-3H3/t20-,21+,24-,25+,26-/m0/s1
SMILES:	CN1C(=O)[C@]2([C@H]([C@@]3(c4ccccc4N(C=O)[C@@H]3N2C(=O)[C@]1(CO)SC)c1c[nH]c2ccccc12)O)SC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047372
PubChem CID:	59051618
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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[453264]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[453264]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[453264]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[453264]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[453264]

☑ 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 NPC297642 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	355
0.1-0.2	2265
0.2-0.3	15989
0.3-0.4	16909
0.4-0.5	2524
0.5-0.6	2825
0.6-0.7	1454
0.7-0.8	346
0.8-0.85	15
0.85-0.9	3
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9952	High Similarity	NPC63279
0.9571	High Similarity	NPC475969
0.9571	High Similarity	NPC475859
0.9571	High Similarity	NPC474877
0.9526	High Similarity	NPC165743
0.9524	High Similarity	NPC470730
0.9524	High Similarity	NPC477175
0.9524	High Similarity	NPC470729
0.9524	High Similarity	NPC477176
0.9479	High Similarity	NPC477177
0.8952	High Similarity	NPC470732
0.8952	High Similarity	NPC470731
0.871	High Similarity	NPC19170
0.8591	High Similarity	NPC297862
0.8364	Intermediate Similarity	NPC253987
0.8364	Intermediate Similarity	NPC312942
0.8364	Intermediate Similarity	NPC327095
0.8326	Intermediate Similarity	NPC40455
0.8318	Intermediate Similarity	NPC162860
0.8224	Intermediate Similarity	NPC54420
0.819	Intermediate Similarity	NPC272174
0.8161	Intermediate Similarity	NPC476817
0.8072	Intermediate Similarity	NPC474896
0.8065	Intermediate Similarity	NPC223791
0.8065	Intermediate Similarity	NPC107077
0.8048	Intermediate Similarity	NPC294693
0.8045	Intermediate Similarity	NPC478157
0.8036	Intermediate Similarity	NPC31097
0.7991	Intermediate Similarity	NPC475506
0.7982	Intermediate Similarity	NPC478158
0.7965	Intermediate Similarity	NPC478028
0.7955	Intermediate Similarity	NPC75726
0.7955	Intermediate Similarity	NPC31385
0.7955	Intermediate Similarity	NPC110602
0.7953	Intermediate Similarity	NPC155143
0.7941	Intermediate Similarity	NPC14812
0.7937	Intermediate Similarity	NPC477714
0.7937	Intermediate Similarity	NPC281049
0.7936	Intermediate Similarity	NPC470491
0.7934	Intermediate Similarity	NPC171317
0.7897	Intermediate Similarity	NPC478029
0.7892	Intermediate Similarity	NPC477715
0.785	Intermediate Similarity	NPC473640
0.7838	Intermediate Similarity	NPC54744
0.7828	Intermediate Similarity	NPC320968
0.7798	Intermediate Similarity	NPC473376
0.7793	Intermediate Similarity	NPC75634
0.7762	Intermediate Similarity	NPC17059
0.7733	Intermediate Similarity	NPC314056
0.7725	Intermediate Similarity	NPC213629
0.7714	Intermediate Similarity	NPC94752
0.7699	Intermediate Similarity	NPC475736
0.7696	Intermediate Similarity	NPC470497
0.7686	Intermediate Similarity	NPC64216
0.7682	Intermediate Similarity	NPC89987
0.7671	Intermediate Similarity	NPC477179
0.7661	Intermediate Similarity	NPC263117
0.7661	Intermediate Similarity	NPC125181
0.7661	Intermediate Similarity	NPC242872
0.7659	Intermediate Similarity	NPC478012
0.7659	Intermediate Similarity	NPC478011
0.765	Intermediate Similarity	NPC100321
0.764	Intermediate Similarity	NPC478013
0.7636	Intermediate Similarity	NPC477181
0.7636	Intermediate Similarity	NPC477178
0.7636	Intermediate Similarity	NPC477180
0.7636	Intermediate Similarity	NPC254850
0.7629	Intermediate Similarity	NPC191382
0.7629	Intermediate Similarity	NPC56109
0.7628	Intermediate Similarity	NPC314176
0.7602	Intermediate Similarity	NPC470490
0.7602	Intermediate Similarity	NPC477174
0.7602	Intermediate Similarity	NPC477173
0.7597	Intermediate Similarity	NPC69843
0.7589	Intermediate Similarity	NPC321939
0.7577	Intermediate Similarity	NPC79386
0.7577	Intermediate Similarity	NPC472285
0.7576	Intermediate Similarity	NPC474196
0.7569	Intermediate Similarity	NPC293917
0.7568	Intermediate Similarity	NPC470488
0.7565	Intermediate Similarity	NPC155444
0.7555	Intermediate Similarity	NPC474195
0.7542	Intermediate Similarity	NPC325976
0.7536	Intermediate Similarity	NPC228835
0.7534	Intermediate Similarity	NPC471945
0.7534	Intermediate Similarity	NPC471950
0.7534	Intermediate Similarity	NPC475259
0.75	Intermediate Similarity	NPC471946
0.75	Intermediate Similarity	NPC471951
0.7488	Intermediate Similarity	NPC163055
0.7477	Intermediate Similarity	NPC321708
0.7469	Intermediate Similarity	NPC153400
0.7468	Intermediate Similarity	NPC24370
0.7468	Intermediate Similarity	NPC319232
0.7467	Intermediate Similarity	NPC191817
0.7467	Intermediate Similarity	NPC475359
0.7466	Intermediate Similarity	NPC476874
0.7447	Intermediate Similarity	NPC326363
0.7443	Intermediate Similarity	NPC131887
0.7439	Intermediate Similarity	NPC314882
0.7429	Intermediate Similarity	NPC11126
0.7424	Intermediate Similarity	NPC238945
0.7421	Intermediate Similarity	NPC300183
0.7418	Intermediate Similarity	NPC15102
0.7411	Intermediate Similarity	NPC323927
0.7407	Intermediate Similarity	NPC117244
0.7407	Intermediate Similarity	NPC473763
0.7406	Intermediate Similarity	NPC28945
0.7393	Intermediate Similarity	NPC91179
0.739	Intermediate Similarity	NPC478006
0.7387	Intermediate Similarity	NPC193761
0.7384	Intermediate Similarity	NPC63031
0.7381	Intermediate Similarity	NPC248454
0.7376	Intermediate Similarity	NPC252338
0.7364	Intermediate Similarity	NPC470499
0.7357	Intermediate Similarity	NPC82370
0.7357	Intermediate Similarity	NPC54981
0.7355	Intermediate Similarity	NPC17487
0.7355	Intermediate Similarity	NPC201831
0.7352	Intermediate Similarity	NPC315467
0.7325	Intermediate Similarity	NPC477109
0.7325	Intermediate Similarity	NPC477107
0.7325	Intermediate Similarity	NPC477108
0.7323	Intermediate Similarity	NPC478009
0.7323	Intermediate Similarity	NPC478010
0.7321	Intermediate Similarity	NPC470489
0.7318	Intermediate Similarity	NPC227582
0.7313	Intermediate Similarity	NPC234999
0.7309	Intermediate Similarity	NPC260900
0.7309	Intermediate Similarity	NPC476073
0.7304	Intermediate Similarity	NPC471192
0.7302	Intermediate Similarity	NPC315555
0.7293	Intermediate Similarity	NPC229348
0.7289	Intermediate Similarity	NPC277350
0.7288	Intermediate Similarity	NPC476491
0.7281	Intermediate Similarity	NPC95783
0.728	Intermediate Similarity	NPC220852
0.728	Intermediate Similarity	NPC323752
0.7264	Intermediate Similarity	NPC248462
0.7264	Intermediate Similarity	NPC248041
0.7264	Intermediate Similarity	NPC126709
0.7264	Intermediate Similarity	NPC283219
0.7261	Intermediate Similarity	NPC184225
0.7261	Intermediate Similarity	NPC474412
0.7261	Intermediate Similarity	NPC285343
0.7249	Intermediate Similarity	NPC471193
0.7249	Intermediate Similarity	NPC471194
0.7249	Intermediate Similarity	NPC6865
0.7249	Intermediate Similarity	NPC153980
0.7241	Intermediate Similarity	NPC473310
0.7235	Intermediate Similarity	NPC175474
0.7231	Intermediate Similarity	NPC470784
0.7229	Intermediate Similarity	NPC36405
0.7225	Intermediate Similarity	NPC71238
0.7225	Intermediate Similarity	NPC314957
0.7222	Intermediate Similarity	NPC235684
0.7222	Intermediate Similarity	NPC62749
0.7217	Intermediate Similarity	NPC145885
0.7217	Intermediate Similarity	NPC14113
0.7217	Intermediate Similarity	NPC84827
0.7217	Intermediate Similarity	NPC64436
0.7208	Intermediate Similarity	NPC70155
0.7207	Intermediate Similarity	NPC52557
0.7205	Intermediate Similarity	NPC72956
0.72	Intermediate Similarity	NPC317701
0.72	Intermediate Similarity	NPC98715
0.7197	Intermediate Similarity	NPC477633
0.719	Intermediate Similarity	NPC184680
0.7183	Intermediate Similarity	NPC219336
0.7181	Intermediate Similarity	NPC46225
0.7181	Intermediate Similarity	NPC225821
0.7177	Intermediate Similarity	NPC477635
0.7177	Intermediate Similarity	NPC477630
0.7176	Intermediate Similarity	NPC99939
0.7176	Intermediate Similarity	NPC308931
0.7175	Intermediate Similarity	NPC74413
0.7174	Intermediate Similarity	NPC475778
0.7174	Intermediate Similarity	NPC151976
0.7174	Intermediate Similarity	NPC87856
0.717	Intermediate Similarity	NPC267885
0.7161	Intermediate Similarity	NPC229893
0.716	Intermediate Similarity	NPC470785
0.7156	Intermediate Similarity	NPC161861
0.7155	Intermediate Similarity	NPC204491
0.7155	Intermediate Similarity	NPC203614
0.715	Intermediate Similarity	NPC16659
0.7149	Intermediate Similarity	NPC258062
0.7149	Intermediate Similarity	NPC127677
0.7143	Intermediate Similarity	NPC475258
0.7143	Intermediate Similarity	NPC49196
0.7143	Intermediate Similarity	NPC475602
0.7143	Intermediate Similarity	NPC171393
0.7143	Intermediate Similarity	NPC295452
0.7143	Intermediate Similarity	NPC214428
0.7143	Intermediate Similarity	NPC195461
0.7143	Intermediate Similarity	NPC249150
0.7143	Intermediate Similarity	NPC79129
0.7143	Intermediate Similarity	NPC313985
0.7143	Intermediate Similarity	NPC267965
0.7143	Intermediate Similarity	NPC81654

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 NPC297642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	554
0.2-0.3	896
0.3-0.4	1958
0.4-0.5	2375
0.5-0.6	2278
0.6-0.7	828
0.7-0.8	76
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7945	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD8272	Phase 2
0.7803	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7970	Approved
0.7793	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7711	Discontinued
0.7672	Intermediate Similarity	NPD7824	Approved
0.7668	Intermediate Similarity	NPD7470	Discontinued
0.765	Intermediate Similarity	NPD7950	Approved
0.765	Intermediate Similarity	NPD7789	Approved
0.765	Intermediate Similarity	NPD7791	Approved
0.765	Intermediate Similarity	NPD7952	Approved
0.765	Intermediate Similarity	NPD7951	Approved
0.765	Intermediate Similarity	NPD7790	Approved
0.765	Intermediate Similarity	NPD7953	Approved
0.7636	Intermediate Similarity	NPD5426	Phase 3
0.7629	Intermediate Similarity	NPD7780	Approved
0.7629	Intermediate Similarity	NPD7781	Approved
0.7628	Intermediate Similarity	NPD7619	Phase 3
0.7628	Intermediate Similarity	NPD7618	Phase 3
0.7628	Intermediate Similarity	NPD7944	Discontinued
0.7586	Intermediate Similarity	NPD7731	Approved
0.7586	Intermediate Similarity	NPD7730	Approved
0.7576	Intermediate Similarity	NPD7271	Approved
0.7569	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6173	Approved
0.7444	Intermediate Similarity	NPD7001	Phase 3
0.7436	Intermediate Similarity	NPD6164	Phase 2
0.7436	Intermediate Similarity	NPD6165	Phase 2
0.7411	Intermediate Similarity	NPD8322	Phase 2
0.7411	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD8072	Approved
0.733	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6999	Discontinued
0.7321	Intermediate Similarity	NPD8169	Discontinued
0.7319	Intermediate Similarity	NPD7603	Discontinued
0.7311	Intermediate Similarity	NPD6595	Phase 3
0.7309	Intermediate Similarity	NPD8073	Approved
0.7293	Intermediate Similarity	NPD8094	Discontinued
0.7289	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD8093	Discontinued
0.7244	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD2094	Phase 2
0.7243	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD2095	Phase 2
0.7243	Intermediate Similarity	NPD2092	Phase 2
0.7237	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7666	Phase 3
0.7225	Intermediate Similarity	NPD7665	Phase 2
0.7217	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2091	Phase 2
0.7209	Intermediate Similarity	NPD2096	Phase 2
0.7176	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4601	Approved
0.7143	Intermediate Similarity	NPD4600	Approved
0.7124	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2787	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD482	Approved
0.7111	Intermediate Similarity	NPD7817	Phase 1
0.711	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD8284	Discontinued
0.7101	Intermediate Similarity	NPD8289	Discontinued
0.7051	Intermediate Similarity	NPD8271	Discontinued
0.7043	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8114	Approved
0.7018	Intermediate Similarity	NPD8115	Approved
0.7017	Intermediate Similarity	NPD7661	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6664	Approved
0.7009	Intermediate Similarity	NPD6044	Discontinued
0.7	Intermediate Similarity	NPD2510	Approved
0.7	Intermediate Similarity	NPD2509	Approved
0.6995	Remote Similarity	NPD750	Phase 2
0.6991	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7957	Phase 1
0.6987	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6665	Discontinued
0.6979	Remote Similarity	NPD5818	Discontinued
0.6979	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5065	Approved
0.696	Remote Similarity	NPD7727	Phase 2
0.6958	Remote Similarity	NPD8075	Discontinued
0.6957	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7716	Approved
0.6946	Remote Similarity	NPD7717	Approved
0.6943	Remote Similarity	NPD5901	Discontinued
0.6938	Remote Similarity	NPD2511	Approved
0.6936	Remote Similarity	NPD7543	Phase 2
0.6933	Remote Similarity	NPD2880	Discontinued
0.6926	Remote Similarity	NPD7415	Suspended
0.6926	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.692	Remote Similarity	NPD5198	Approved
0.692	Remote Similarity	NPD5199	Approved
0.6909	Remote Similarity	NPD7026	Phase 2
0.6901	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5017	Discontinued
0.6885	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3961	Discontinued
0.6866	Remote Similarity	NPD4079	Approved
0.6866	Remote Similarity	NPD4076	Approved
0.6865	Remote Similarity	NPD4558	Phase 2
0.6861	Remote Similarity	NPD8240	Discontinued
0.6861	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD5003	Discontinued
0.6856	Remote Similarity	NPD3015	Discontinued
0.6856	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2442	Approved
0.6853	Remote Similarity	NPD2443	Approved
0.6849	Remote Similarity	NPD7168	Phase 3
0.6847	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD4602	Approved
0.6835	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8256	Approved
0.6835	Remote Similarity	NPD8257	Approved
0.6834	Remote Similarity	NPD5461	Discontinued
0.6833	Remote Similarity	NPD6995	Phase 1
0.6833	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4397	Phase 1
0.6826	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.682	Remote Similarity	NPD3506	Approved
0.682	Remote Similarity	NPD3505	Approved
0.6816	Remote Similarity	NPD4499	Approved
0.6816	Remote Similarity	NPD8119	Discontinued
0.6814	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4852	Phase 2
0.6802	Remote Similarity	NPD8431	Approved
0.68	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6268	Phase 1
0.6781	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8349	Phase 1
0.6776	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8484	Phase 2
0.6769	Remote Similarity	NPD484	Approved
0.6763	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD8250	Phase 2
0.6753	Remote Similarity	NPD6176	Phase 1
0.6741	Remote Similarity	NPD3321	Discontinued
0.6732	Remote Similarity	NPD8247	Approved
0.6732	Remote Similarity	NPD8246	Approved
0.673	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3394	Approved
0.6723	Remote Similarity	NPD3389	Approved
0.6723	Remote Similarity	NPD4990	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3393	Approved
0.672	Remote Similarity	NPD2893	Phase 3
0.6711	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7948	Phase 1
0.6709	Remote Similarity	NPD2847	Phase 2
0.6709	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7688	Phase 1
0.6707	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5596	Phase 2
0.6696	Remote Similarity	NPD4501	Approved
0.6696	Remote Similarity	NPD4500	Approved
0.6696	Remote Similarity	NPD5043	Discontinued
0.6694	Remote Similarity	NPD5559	Phase 2
0.6681	Remote Similarity	NPD2408	Discontinued
0.6681	Remote Similarity	NPD4310	Phase 3
0.6681	Remote Similarity	NPD5487	Phase 1
0.668	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.668	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4885	Approved
0.668	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1096	Discontinued
0.6667	Remote Similarity	NPD2144	Approved
0.6653	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4906	Approved
0.6652	Remote Similarity	NPD4905	Approved
0.6652	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4903	Approved
0.6652	Remote Similarity	NPD6987	Phase 1
0.6651	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4612	Discontinued
0.6637	Remote Similarity	NPD3082	Discontinued
0.6637	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3610	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