NPASS Compound

Structure

NPC166209 OpenBabel07101719122D 27 31 0 0 1 0 0 0 0 0999 V2000 3.2564 2.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8745 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3904 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0085 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7405 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0540 -0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6720 2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7405 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3904 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0085 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2653 1.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2564 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8745 1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9885 2.7044 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.6065 -0.8023 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 -0.2738 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6666 2.1759 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 1.9021 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 -1.6473 -0.5352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 10 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 11 2 0 0 0 0 6 17 1 0 0 0 0 7 14 2 0 0 0 0 7 23 1 0 0 0 0 8 15 2 0 0 0 0 8 24 1 0 0 0 0 9 18 1 0 0 0 0 9 25 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 15 19 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 14 1 1 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 20 27 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	483.95
Volume:	376.674
LogP:	4.556
LogD:	3.93
LogS:	-3.999
# Rotatable Bonds:	2
TPSA:	73.04
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.38
Synthetic Accessibility Score:	3.545
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.31
MDCK Permeability:	1.1026799256796949e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.154
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.9
Plasma Protein Binding (PPB):	95.03728485107422%
Volume Distribution (VD):	2.092
Pgp-substrate:	6.403634548187256%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.375
CYP2C19-inhibitor:	0.895
CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.645
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.795
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	1.814
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.2
Human Hepatotoxicity (H-HT):	0.689
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.915
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.16
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.542

Download Data

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

Natural Product: NPC166209

Natural Product ID:	NPC166209
*Common Name:**	(2R)-2,5-Bis(6-Bromo-1H-Indol-3-Yl)-2,3-Dihydro-1H-Pyrazin-6-One
IUPAC Name:	(2R)-2,5-bis(6-bromo-1H-indol-3-yl)-2,3-dihydro-1H-pyrazin-6-one
Synonyms:
Standard InCHIKey:	LJVUNJVGWMVCQH-SFHVURJKSA-N
Standard InCHI:	InChI=1S/C20H14Br2N4O/c21-10-1-3-12-14(7-23-16(12)5-10)18-9-25-19(20(27)26-18)15-8-24-17-6-11(22)2-4-13(15)17/h1-8,18,23-24H,9H2,(H,26,27)/t18-/m0/s1
SMILES:	c1cc2c(c[nH]c2cc1Br)[C@@H]1CN=C(c2c[nH]c3cc(ccc23)Br)C(=O)N1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL197988
PubChem CID:	11294704
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921415]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16154746]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253840]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	southern australian	n.a.	PMID[9599272]

☑ 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
MIC	1

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	86.34	ug.mL-1	PMID[535761]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.12	ug.mL-1	PMID[535761]

☑ 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 NPC166209 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	771
0.1-0.2	12620
0.2-0.3	19632
0.3-0.4	4284
0.4-0.5	2290
0.5-0.6	1658
0.6-0.7	1123
0.7-0.8	288
0.8-0.85	18
0.85-0.9	1
0.9-0.95	2
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC13456
1.0	High Similarity	NPC269203
1.0	High Similarity	NPC77241
0.9944	High Similarity	NPC475914
0.9944	High Similarity	NPC268744
0.9944	High Similarity	NPC201266
0.9944	High Similarity	NPC153123
0.9944	High Similarity	NPC220797
0.9944	High Similarity	NPC474318
0.9157	High Similarity	NPC99939
0.9157	High Similarity	NPC308931
0.8547	High Similarity	NPC477611
0.8526	High Similarity	NPC474389
0.8485	Intermediate Similarity	NPC470703
0.8482	Intermediate Similarity	NPC477004
0.8434	Intermediate Similarity	NPC470702
0.8434	Intermediate Similarity	NPC473218
0.8394	Intermediate Similarity	NPC94211
0.8394	Intermediate Similarity	NPC52909
0.8394	Intermediate Similarity	NPC475935
0.8342	Intermediate Similarity	NPC23420
0.8342	Intermediate Similarity	NPC205254
0.8342	Intermediate Similarity	NPC106771
0.8342	Intermediate Similarity	NPC303820
0.8158	Intermediate Similarity	NPC231536
0.8115	Intermediate Similarity	NPC476460
0.8054	Intermediate Similarity	NPC474958
0.8053	Intermediate Similarity	NPC17059
0.8031	Intermediate Similarity	NPC188821
0.8031	Intermediate Similarity	NPC474180
0.801	Intermediate Similarity	NPC237414
0.7989	Intermediate Similarity	NPC110158
0.7968	Intermediate Similarity	NPC11126
0.7967	Intermediate Similarity	NPC17751
0.7967	Intermediate Similarity	NPC274229
0.794	Intermediate Similarity	NPC317701
0.7938	Intermediate Similarity	NPC88315
0.7921	Intermediate Similarity	NPC141926
0.7895	Intermediate Similarity	NPC228835
0.7892	Intermediate Similarity	NPC82331
0.785	Intermediate Similarity	NPC63031
0.7846	Intermediate Similarity	NPC304203
0.7801	Intermediate Similarity	NPC477003
0.7789	Intermediate Similarity	NPC307191
0.7755	Intermediate Similarity	NPC326422
0.7754	Intermediate Similarity	NPC161861
0.7749	Intermediate Similarity	NPC470205
0.774	Intermediate Similarity	NPC288838
0.7732	Intermediate Similarity	NPC321708
0.7731	Intermediate Similarity	NPC474357
0.7725	Intermediate Similarity	NPC284775
0.7713	Intermediate Similarity	NPC280297
0.7703	Intermediate Similarity	NPC475736
0.7688	Intermediate Similarity	NPC131887
0.7685	Intermediate Similarity	NPC935
0.7685	Intermediate Similarity	NPC267078
0.7668	Intermediate Similarity	NPC15102
0.765	Intermediate Similarity	NPC92796
0.765	Intermediate Similarity	NPC135141
0.7644	Intermediate Similarity	NPC91179
0.7638	Intermediate Similarity	NPC227582
0.7634	Intermediate Similarity	NPC56233
0.7632	Intermediate Similarity	NPC59269
0.763	Intermediate Similarity	NPC474195
0.7629	Intermediate Similarity	NPC94752
0.7622	Intermediate Similarity	NPC317105
0.7622	Intermediate Similarity	NPC149265
0.7614	Intermediate Similarity	NPC477166
0.7614	Intermediate Similarity	NPC477167
0.7614	Intermediate Similarity	NPC473342
0.7614	Intermediate Similarity	NPC304187
0.7611	Intermediate Similarity	NPC53947
0.7592	Intermediate Similarity	NPC276540
0.7592	Intermediate Similarity	NPC233050
0.7581	Intermediate Similarity	NPC280864
0.757	Intermediate Similarity	NPC474196
0.7568	Intermediate Similarity	NPC17487
0.7568	Intermediate Similarity	NPC201831
0.7562	Intermediate Similarity	NPC74413
0.7558	Intermediate Similarity	NPC470323
0.7553	Intermediate Similarity	NPC97343
0.755	Intermediate Similarity	NPC167710
0.7548	Intermediate Similarity	NPC207020
0.7537	Intermediate Similarity	NPC476073
0.7534	Intermediate Similarity	NPC477109
0.7534	Intermediate Similarity	NPC477107
0.7534	Intermediate Similarity	NPC477108
0.7527	Intermediate Similarity	NPC325903
0.7526	Intermediate Similarity	NPC108011
0.7525	Intermediate Similarity	NPC252338
0.7513	Intermediate Similarity	NPC275292
0.7513	Intermediate Similarity	NPC243381
0.7512	Intermediate Similarity	NPC67288
0.75	Intermediate Similarity	NPC216643
0.7488	Intermediate Similarity	NPC477715
0.7487	Intermediate Similarity	NPC133003
0.7486	Intermediate Similarity	NPC34844
0.7478	Intermediate Similarity	NPC475746
0.7476	Intermediate Similarity	NPC54420
0.7462	Intermediate Similarity	NPC213629
0.7459	Intermediate Similarity	NPC2272
0.7453	Intermediate Similarity	NPC477714
0.7451	Intermediate Similarity	NPC260900
0.745	Intermediate Similarity	NPC294693
0.7447	Intermediate Similarity	NPC478183
0.7436	Intermediate Similarity	NPC21429
0.7433	Intermediate Similarity	NPC478184
0.7433	Intermediate Similarity	NPC271797
0.7433	Intermediate Similarity	NPC247987
0.7433	Intermediate Similarity	NPC21174
0.7424	Intermediate Similarity	NPC324091
0.7416	Intermediate Similarity	NPC72956
0.7413	Intermediate Similarity	NPC179701
0.7404	Intermediate Similarity	NPC162860
0.7404	Intermediate Similarity	NPC478158
0.7393	Intermediate Similarity	NPC478157
0.7385	Intermediate Similarity	NPC156003
0.7381	Intermediate Similarity	NPC471194
0.7381	Intermediate Similarity	NPC471193
0.7381	Intermediate Similarity	NPC6865
0.7381	Intermediate Similarity	NPC153980
0.7376	Intermediate Similarity	NPC262898
0.7371	Intermediate Similarity	NPC16659
0.7366	Intermediate Similarity	NPC473761
0.736	Intermediate Similarity	NPC62749
0.7358	Intermediate Similarity	NPC240088
0.7358	Intermediate Similarity	NPC473380
0.7348	Intermediate Similarity	NPC316069
0.7347	Intermediate Similarity	NPC467063
0.7346	Intermediate Similarity	NPC477610
0.7343	Intermediate Similarity	NPC82053
0.7342	Intermediate Similarity	NPC117980
0.734	Intermediate Similarity	NPC171317
0.7333	Intermediate Similarity	NPC191415
0.7326	Intermediate Similarity	NPC122141
0.732	Intermediate Similarity	NPC265710
0.7316	Intermediate Similarity	NPC63751
0.7308	Intermediate Similarity	NPC469811
0.7306	Intermediate Similarity	NPC280852
0.7302	Intermediate Similarity	NPC42372
0.7299	Intermediate Similarity	NPC75634
0.7296	Intermediate Similarity	NPC102755
0.7295	Intermediate Similarity	NPC473376
0.7293	Intermediate Similarity	NPC470440
0.7288	Intermediate Similarity	NPC105127
0.7278	Intermediate Similarity	NPC190296
0.7277	Intermediate Similarity	NPC471943
0.7277	Intermediate Similarity	NPC471192
0.7273	Intermediate Similarity	NPC293487
0.7268	Intermediate Similarity	NPC321911
0.7268	Intermediate Similarity	NPC111275
0.7254	Intermediate Similarity	NPC149155
0.7254	Intermediate Similarity	NPC203468
0.7254	Intermediate Similarity	NPC110500
0.7253	Intermediate Similarity	NPC63545
0.7253	Intermediate Similarity	NPC143872
0.7249	Intermediate Similarity	NPC478182
0.7243	Intermediate Similarity	NPC200214
0.7243	Intermediate Similarity	NPC477114
0.7232	Intermediate Similarity	NPC96102
0.7231	Intermediate Similarity	NPC55772
0.7225	Intermediate Similarity	NPC78020
0.722	Intermediate Similarity	NPC19696
0.722	Intermediate Similarity	NPC293917
0.722	Intermediate Similarity	NPC136957
0.7216	Intermediate Similarity	NPC267885
0.7213	Intermediate Similarity	NPC201380
0.7213	Intermediate Similarity	NPC179787
0.7207	Intermediate Similarity	NPC110126
0.7206	Intermediate Similarity	NPC174281
0.7206	Intermediate Similarity	NPC475286
0.7198	Intermediate Similarity	NPC159856
0.7198	Intermediate Similarity	NPC314372
0.7196	Intermediate Similarity	NPC470731
0.7196	Intermediate Similarity	NPC470732
0.7194	Intermediate Similarity	NPC88110
0.7191	Intermediate Similarity	NPC84911
0.7188	Intermediate Similarity	NPC194411
0.7186	Intermediate Similarity	NPC17273
0.7186	Intermediate Similarity	NPC141612
0.7186	Intermediate Similarity	NPC135601
0.7181	Intermediate Similarity	NPC475990
0.7181	Intermediate Similarity	NPC206819
0.7181	Intermediate Similarity	NPC318065
0.7179	Intermediate Similarity	NPC84827
0.7179	Intermediate Similarity	NPC145885
0.7179	Intermediate Similarity	NPC14113
0.7172	Intermediate Similarity	NPC165495
0.7167	Intermediate Similarity	NPC469768
0.7167	Intermediate Similarity	NPC469779
0.7167	Intermediate Similarity	NPC469784
0.7167	Intermediate Similarity	NPC469761
0.7167	Intermediate Similarity	NPC469780
0.7167	Intermediate Similarity	NPC469783
0.7167	Intermediate Similarity	NPC469767
0.7165	Intermediate Similarity	NPC469529
0.7165	Intermediate Similarity	NPC293216
0.7151	Intermediate Similarity	NPC232798
0.7143	Intermediate Similarity	NPC248041
0.7143	Intermediate Similarity	NPC283219

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 NPC166209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	808
0.2-0.3	1211
0.3-0.4	2275
0.4-0.5	2219
0.5-0.6	1714
0.6-0.7	502
0.7-0.8	57
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
0.8021	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7619	Phase 3
0.7806	Intermediate Similarity	NPD7618	Phase 3
0.7766	Intermediate Similarity	NPD4075	Phase 2
0.7629	Intermediate Similarity	NPD6217	Discontinued
0.7556	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6664	Approved
0.7549	Intermediate Similarity	NPD5426	Phase 3
0.7538	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD4922	Phase 2
0.7436	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7564	Discontinued
0.7419	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD3961	Discontinued
0.7391	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2880	Discontinued
0.7358	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2442	Approved
0.7356	Intermediate Similarity	NPD2443	Approved
0.731	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3319	Phase 1
0.7296	Intermediate Similarity	NPD3320	Approved
0.7296	Intermediate Similarity	NPD3318	Approved
0.7282	Intermediate Similarity	NPD6595	Phase 3
0.7254	Intermediate Similarity	NPD482	Approved
0.7254	Intermediate Similarity	NPD4128	Approved
0.7251	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4848	Phase 1
0.7232	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD786	Approved
0.719	Intermediate Similarity	NPD7665	Phase 2
0.719	Intermediate Similarity	NPD6459	Phase 2
0.719	Intermediate Similarity	NPD7666	Phase 3
0.7177	Intermediate Similarity	NPD2008	Discontinued
0.7174	Intermediate Similarity	NPD3100	Discontinued
0.7172	Intermediate Similarity	NPD2091	Phase 2
0.7172	Intermediate Similarity	NPD2096	Phase 2
0.7158	Intermediate Similarity	NPD3583	Phase 2
0.7156	Intermediate Similarity	NPD2408	Discontinued
0.7151	Intermediate Similarity	NPD2837	Discontinued
0.715	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2411	Approved
0.7136	Intermediate Similarity	NPD8093	Discontinued
0.7136	Intermediate Similarity	NPD6999	Discontinued
0.7136	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2172	Phase 1
0.7128	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD1722	Approved
0.7123	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2092	Phase 2
0.7121	Intermediate Similarity	NPD2095	Phase 2
0.7121	Intermediate Similarity	NPD2094	Phase 2
0.7108	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7470	Discontinued
0.7077	Intermediate Similarity	NPD5065	Approved
0.7065	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5901	Discontinued
0.7024	Intermediate Similarity	NPD7944	Discontinued
0.7023	Intermediate Similarity	NPD8094	Discontinued
0.7022	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5473	Discontinued
0.7016	Intermediate Similarity	NPD5400	Approved
0.7016	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6771	Discontinued
0.7015	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3506	Approved
0.7005	Intermediate Similarity	NPD3505	Approved
0.7005	Intermediate Similarity	NPD4181	Approved
0.6996	Remote Similarity	NPD7780	Approved
0.6996	Remote Similarity	NPD7781	Approved
0.6995	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7970	Approved
0.6985	Remote Similarity	NPD1895	Discontinued
0.6979	Remote Similarity	NPD3323	Discontinued
0.6972	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4079	Approved
0.697	Remote Similarity	NPD4076	Approved
0.697	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6165	Phase 2
0.6951	Remote Similarity	NPD6164	Phase 2
0.6946	Remote Similarity	NPD7175	Phase 1
0.6941	Remote Similarity	NPD5199	Approved
0.6941	Remote Similarity	NPD5198	Approved
0.6939	Remote Similarity	NPD750	Phase 2
0.6927	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2289	Phase 3
0.6908	Remote Similarity	NPD2290	Phase 3
0.6906	Remote Similarity	NPD201	Phase 2
0.6906	Remote Similarity	NPD7603	Discontinued
0.6906	Remote Similarity	NPD200	Phase 2
0.6905	Remote Similarity	NPD5017	Discontinued
0.6905	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7716	Approved
0.6892	Remote Similarity	NPD7717	Approved
0.6872	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7001	Phase 3
0.685	Remote Similarity	NPD2481	Approved
0.685	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.685	Remote Similarity	NPD2479	Phase 3
0.6849	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1982	Phase 1
0.6837	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2071	Approved
0.6831	Remote Similarity	NPD2069	Approved
0.6831	Remote Similarity	NPD2068	Approved
0.6831	Remote Similarity	NPD2070	Approved
0.6827	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2642	Approved
0.6821	Remote Similarity	NPD2639	Approved
0.6818	Remote Similarity	NPD6470	Phase 3
0.6814	Remote Similarity	NPD8431	Approved
0.68	Remote Similarity	NPD3076	Approved
0.68	Remote Similarity	NPD3079	Approved
0.68	Remote Similarity	NPD3077	Approved
0.68	Remote Similarity	NPD3078	Approved
0.6798	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5446	Phase 2
0.6792	Remote Similarity	NPD2879	Approved
0.6792	Remote Similarity	NPD2881	Approved
0.6791	Remote Similarity	NPD2510	Approved
0.6791	Remote Similarity	NPD2509	Approved
0.6791	Remote Similarity	NPD5421	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6044	Discontinued
0.6782	Remote Similarity	NPD5105	Approved
0.6782	Remote Similarity	NPD5106	Approved
0.6776	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4863	Approved
0.6772	Remote Similarity	NPD4462	Approved
0.6772	Remote Similarity	NPD4463	Approved
0.6765	Remote Similarity	NPD7026	Phase 2
0.6762	Remote Similarity	NPD4364	Phase 1
0.6749	Remote Similarity	NPD6178	Phase 3
0.6748	Remote Similarity	NPD4499	Approved
0.6746	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1506	Discontinued
0.6744	Remote Similarity	NPD3905	Phase 3
0.6744	Remote Similarity	NPD8322	Phase 2
0.6743	Remote Similarity	NPD4852	Phase 2
0.6739	Remote Similarity	NPD6986	Phase 1
0.6734	Remote Similarity	NPD4883	Approved
0.6731	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD8272	Phase 2
0.6728	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4051	Discontinued
0.6725	Remote Similarity	NPD7951	Approved
0.6725	Remote Similarity	NPD7952	Approved
0.6725	Remote Similarity	NPD7789	Approved
0.6725	Remote Similarity	NPD7791	Approved
0.6725	Remote Similarity	NPD7950	Approved
0.6725	Remote Similarity	NPD7790	Approved
0.6725	Remote Similarity	NPD7953	Approved
0.672	Remote Similarity	NPD1183	Approved
0.6717	Remote Similarity	NPD3610	Approved
0.6717	Remote Similarity	NPD3609	Approved
0.6712	Remote Similarity	NPD6787	Phase 2
0.6703	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5818	Discontinued
0.6697	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7185	Discontinued
0.6697	Remote Similarity	NPD8257	Approved
0.6697	Remote Similarity	NPD8256	Approved
0.6683	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3431	Approved
0.6683	Remote Similarity	NPD3430	Approved
0.6667	Remote Similarity	NPD7657	Approved
0.6667	Remote Similarity	NPD4547	Phase 3
0.6667	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7656	Approved
0.6667	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2144	Approved
0.6652	Remote Similarity	NPD7731	Approved
0.6652	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7730	Approved
0.6651	Remote Similarity	NPD7209	Approved
0.6651	Remote Similarity	NPD7207	Approved
0.6651	Remote Similarity	NPD7208	Approved
0.665	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7394	Phase 2
0.665	Remote Similarity	NPD4011	Clinical (unspecified phase)

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