NPASS Compound

Structure

NPC260900 OpenBabel07101719132D 35 39 0 0 0 0 0 0 0 0999 V2000 3.4373 -2.5613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0259 -2.1823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3013 -1.5299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4004 -1.2012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9629 3.0206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1360 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4953 2.8824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4054 2.8824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4226 2.5811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5219 2.5811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7707 2.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1300 2.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6253 1.6274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7246 1.6274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9735 -0.3013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9735 1.2763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9273 1.2763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4004 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9007 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5004 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4254 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4754 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9379 1.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9629 -0.3569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9379 -0.3569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9629 1.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9273 -0.3013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2286 -1.2286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9007 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4254 2.1762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4754 -1.2012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4254 -1.2012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4754 2.1762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 29 1 0 0 0 0 3 29 1 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 29 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 16 2 0 0 0 0 12 17 2 0 0 0 0 13 19 2 0 0 0 0 14 20 2 0 0 0 0 15 18 2 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 23 1 0 0 0 0 21 28 2 0 0 0 0 22 24 1 0 0 0 0 22 26 2 0 0 0 0 23 25 1 0 0 0 0 23 27 2 0 0 0 0 24 27 1 0 0 0 0 24 32 2 0 0 0 0 25 26 1 0 0 0 0 25 33 2 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 29 1 0 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.19
Volume:	490.238
LogP:	5.403
LogD:	3.485
LogS:	-4.658
# Rotatable Bonds:	4
TPSA:	83.64
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.437
Synthetic Accessibility Score:	3.556
Fsp3:	0.172
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.014
MDCK Permeability:	1.0489903615962248e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	94.91458892822266%
Volume Distribution (VD):	0.392
Pgp-substrate:	10.240690231323242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.909
CYP2C19-inhibitor:	0.666
CYP2C19-substrate:	0.449
CYP2C9-inhibitor:	0.807
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.521
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.216
CYP3A4-substrate:	0.534

ADMET: Excretion

Clearance (CL):	0.479
Half-life (T1/2):	0.023

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.177
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.811
Carcinogencity:	0.859
Eye Corrosion:	0.003
Eye Irritation:	0.279
Respiratory Toxicity:	0.725

Download Data

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

Natural Product: NPC260900

Natural Product ID:	NPC260900
*Common Name:**	Asterriquinone C-1
IUPAC Name:	2-(1H-indol-3-yl)-3,6-dimethoxy-5-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione
Synonyms:	Asterriquinone C-1
Standard InCHIKey:	VMGKCTQSPITGEV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H26N2O4/c1-6-29(2,3)28-21(17-12-8-10-14-20(17)31-28)23-25(33)26(34-4)22(24(32)27(23)35-5)18-15-30-19-13-9-7-11-16(18)19/h6-15,30-31H,1H2,2-5H3
SMILES:	C=CC(C)(C)c1c(c2ccccc2[nH]1)C1=C(C(=O)C(=C(C1=O)OC)c1c[nH]c2ccccc12)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467829
PubChem CID:	23247889
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	from the rhizosphere of Opuntia versicolor of the Sonoran Desert	n.a.	PMID[14695798]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124769]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271552]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22360613]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24534845]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25671343]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2921224]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30207465]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32163285]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32897070]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984154]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	24200.0	nM	PMID[507359]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4100.0	nM	PMID[507359]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	25700.0	nM	PMID[507359]

☑ 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 NPC260900 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	379
0.1-0.2	2402
0.2-0.3	11861
0.3-0.4	19494
0.4-0.5	4208
0.5-0.6	1768
0.6-0.7	1903
0.7-0.8	649
0.8-0.85	27
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9832	High Similarity	NPC74413
0.9454	High Similarity	NPC252338
0.9396	High Similarity	NPC227582
0.9219	High Similarity	NPC474412
0.8534	High Similarity	NPC67288
0.8438	Intermediate Similarity	NPC131887
0.835	Intermediate Similarity	NPC476818
0.8307	Intermediate Similarity	NPC321708
0.827	Intermediate Similarity	NPC55772
0.8227	Intermediate Similarity	NPC36405
0.822	Intermediate Similarity	NPC476460
0.8173	Intermediate Similarity	NPC476073
0.8135	Intermediate Similarity	NPC304203
0.8083	Intermediate Similarity	NPC47190
0.8073	Intermediate Similarity	NPC154339
0.806	Intermediate Similarity	NPC258062
0.8053	Intermediate Similarity	NPC99939
0.8053	Intermediate Similarity	NPC308931
0.8051	Intermediate Similarity	NPC11445
0.805	Intermediate Similarity	NPC472064
0.8041	Intermediate Similarity	NPC267343
0.803	Intermediate Similarity	NPC82370
0.8021	Intermediate Similarity	NPC111275
0.8021	Intermediate Similarity	NPC59269
0.8021	Intermediate Similarity	NPC284775
0.801	Intermediate Similarity	NPC225821
0.801	Intermediate Similarity	NPC235684
0.8	Intermediate Similarity	NPC157828
0.8	Intermediate Similarity	NPC195239
0.799	Intermediate Similarity	NPC193761
0.799	Intermediate Similarity	NPC87856
0.7981	Intermediate Similarity	NPC276657
0.7979	Intermediate Similarity	NPC213468
0.7971	Intermediate Similarity	NPC264285
0.7961	Intermediate Similarity	NPC132211
0.7961	Intermediate Similarity	NPC203614
0.7931	Intermediate Similarity	NPC271862
0.7926	Intermediate Similarity	NPC14113
0.7926	Intermediate Similarity	NPC84827
0.7926	Intermediate Similarity	NPC145885
0.7917	Intermediate Similarity	NPC315555
0.7913	Intermediate Similarity	NPC478157
0.7907	Intermediate Similarity	NPC70155
0.7905	Intermediate Similarity	NPC16352
0.79	Intermediate Similarity	NPC472063
0.79	Intermediate Similarity	NPC472069
0.79	Intermediate Similarity	NPC472062
0.7892	Intermediate Similarity	NPC78020
0.7887	Intermediate Similarity	NPC472112
0.7882	Intermediate Similarity	NPC127677
0.7872	Intermediate Similarity	NPC267885
0.7871	Intermediate Similarity	NPC472065
0.7867	Intermediate Similarity	NPC229893
0.7861	Intermediate Similarity	NPC98715
0.7861	Intermediate Similarity	NPC317701
0.7857	Intermediate Similarity	NPC2395
0.7857	Intermediate Similarity	NPC326422
0.7843	Intermediate Similarity	NPC478158
0.7839	Intermediate Similarity	NPC284338
0.7833	Intermediate Similarity	NPC46225
0.783	Intermediate Similarity	NPC235885
0.7824	Intermediate Similarity	NPC62749
0.7819	Intermediate Similarity	NPC110500
0.7819	Intermediate Similarity	NPC149155
0.7819	Intermediate Similarity	NPC203468
0.7816	Intermediate Similarity	NPC151976
0.7806	Intermediate Similarity	NPC472113
0.7796	Intermediate Similarity	NPC63751
0.7789	Intermediate Similarity	NPC248041
0.7789	Intermediate Similarity	NPC283219
0.7789	Intermediate Similarity	NPC126709
0.7788	Intermediate Similarity	NPC204491
0.7783	Intermediate Similarity	NPC147446
0.7778	Intermediate Similarity	NPC267965
0.7772	Intermediate Similarity	NPC15102
0.7766	Intermediate Similarity	NPC88315
0.7763	Intermediate Similarity	NPC101350
0.7761	Intermediate Similarity	NPC300183
0.7756	Intermediate Similarity	NPC472070
0.7751	Intermediate Similarity	NPC472285
0.7739	Intermediate Similarity	NPC106824
0.7737	Intermediate Similarity	NPC151939
0.7731	Intermediate Similarity	NPC267853
0.773	Intermediate Similarity	NPC311276
0.7723	Intermediate Similarity	NPC476874
0.7722	Intermediate Similarity	NPC53947
0.772	Intermediate Similarity	NPC477003
0.7717	Intermediate Similarity	NPC235685
0.7717	Intermediate Similarity	NPC15801
0.771	Intermediate Similarity	NPC267926
0.7704	Intermediate Similarity	NPC329858
0.7696	Intermediate Similarity	NPC244897
0.7692	Intermediate Similarity	NPC234078
0.7692	Intermediate Similarity	NPC221100
0.7692	Intermediate Similarity	NPC17059
0.7674	Intermediate Similarity	NPC57690
0.767	Intermediate Similarity	NPC162860
0.7668	Intermediate Similarity	NPC469358
0.7664	Intermediate Similarity	NPC141428
0.7663	Intermediate Similarity	NPC92796
0.7663	Intermediate Similarity	NPC135141
0.7659	Intermediate Similarity	NPC54420
0.7656	Intermediate Similarity	NPC469896
0.7654	Intermediate Similarity	NPC288838
0.7653	Intermediate Similarity	NPC213629
0.7653	Intermediate Similarity	NPC196251
0.7653	Intermediate Similarity	NPC63199
0.7653	Intermediate Similarity	NPC111602
0.7653	Intermediate Similarity	NPC102338
0.765	Intermediate Similarity	NPC290529
0.7647	Intermediate Similarity	NPC160105
0.7647	Intermediate Similarity	NPC474561
0.7647	Intermediate Similarity	NPC49954
0.7644	Intermediate Similarity	NPC207020
0.7644	Intermediate Similarity	NPC64436
0.7641	Intermediate Similarity	NPC118084
0.763	Intermediate Similarity	NPC477714
0.7626	Intermediate Similarity	NPC316411
0.7617	Intermediate Similarity	NPC71037
0.7617	Intermediate Similarity	NPC266192
0.7614	Intermediate Similarity	NPC314333
0.7606	Intermediate Similarity	NPC201700
0.7588	Intermediate Similarity	NPC472295
0.7588	Intermediate Similarity	NPC269886
0.7588	Intermediate Similarity	NPC247735
0.7588	Intermediate Similarity	NPC472210
0.7588	Intermediate Similarity	NPC81802
0.7583	Intermediate Similarity	NPC477715
0.7581	Intermediate Similarity	NPC282231
0.7576	Intermediate Similarity	NPC138370
0.7574	Intermediate Similarity	NPC81535
0.7565	Intermediate Similarity	NPC477042
0.7562	Intermediate Similarity	NPC167710
0.7561	Intermediate Similarity	NPC477043
0.756	Intermediate Similarity	NPC118940
0.756	Intermediate Similarity	NPC75634
0.7556	Intermediate Similarity	NPC178858
0.7549	Intermediate Similarity	NPC474116
0.7547	Intermediate Similarity	NPC473310
0.7546	Intermediate Similarity	NPC472762
0.7541	Intermediate Similarity	NPC25008
0.7541	Intermediate Similarity	NPC469763
0.7541	Intermediate Similarity	NPC469765
0.7541	Intermediate Similarity	NPC73952
0.7541	Intermediate Similarity	NPC469760
0.7541	Intermediate Similarity	NPC469786
0.7541	Intermediate Similarity	NPC259644
0.7538	Intermediate Similarity	NPC258480
0.7538	Intermediate Similarity	NPC472292
0.7537	Intermediate Similarity	NPC213308
0.7537	Intermediate Similarity	NPC214428
0.7534	Intermediate Similarity	NPC207686
0.7527	Intermediate Similarity	NPC279918
0.7526	Intermediate Similarity	NPC191415
0.7525	Intermediate Similarity	NPC470499
0.7525	Intermediate Similarity	NPC83111
0.7525	Intermediate Similarity	NPC149708
0.7525	Intermediate Similarity	NPC477044
0.7525	Intermediate Similarity	NPC477041
0.7525	Intermediate Similarity	NPC171317
0.7514	Intermediate Similarity	NPC469762
0.7514	Intermediate Similarity	NPC216643
0.7513	Intermediate Similarity	NPC248462
0.7512	Intermediate Similarity	NPC192712
0.7512	Intermediate Similarity	NPC472293
0.75	Intermediate Similarity	NPC70922
0.75	Intermediate Similarity	NPC42372
0.75	Intermediate Similarity	NPC75540
0.75	Intermediate Similarity	NPC212376
0.75	Intermediate Similarity	NPC211572
0.75	Intermediate Similarity	NPC280290
0.75	Intermediate Similarity	NPC80597
0.7489	Intermediate Similarity	NPC315062
0.7488	Intermediate Similarity	NPC220797
0.7488	Intermediate Similarity	NPC474318
0.7488	Intermediate Similarity	NPC268744
0.7488	Intermediate Similarity	NPC475914
0.7488	Intermediate Similarity	NPC153123
0.7488	Intermediate Similarity	NPC201266
0.7487	Intermediate Similarity	NPC314603
0.7476	Intermediate Similarity	NPC110182
0.7476	Intermediate Similarity	NPC219087
0.7476	Intermediate Similarity	NPC473376
0.7474	Intermediate Similarity	NPC300688
0.7473	Intermediate Similarity	NPC230869
0.7465	Intermediate Similarity	NPC475338
0.7465	Intermediate Similarity	NPC909
0.7463	Intermediate Similarity	NPC162730
0.7463	Intermediate Similarity	NPC202812
0.7463	Intermediate Similarity	NPC19692
0.7463	Intermediate Similarity	NPC220151
0.7462	Intermediate Similarity	NPC66210
0.7462	Intermediate Similarity	NPC94752
0.7462	Intermediate Similarity	NPC160381
0.746	Intermediate Similarity	NPC54988
0.7459	Intermediate Similarity	NPC469785
0.7455	Intermediate Similarity	NPC63031
0.7452	Intermediate Similarity	NPC314957
0.7451	Intermediate Similarity	NPC77241
0.7451	Intermediate Similarity	NPC269203

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 NPC260900 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	607
0.2-0.3	723
0.3-0.4	1939
0.4-0.5	2687
0.5-0.6	2038
0.6-0.7	802
0.7-0.8	121
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8274	Intermediate Similarity	NPD5426	Phase 3
0.8032	Intermediate Similarity	NPD6595	Phase 3
0.7929	Intermediate Similarity	NPD6999	Discontinued
0.7929	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD5901	Discontinued
0.7906	Intermediate Similarity	NPD2091	Phase 2
0.7906	Intermediate Similarity	NPD2096	Phase 2
0.7872	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD7001	Phase 3
0.7853	Intermediate Similarity	NPD2092	Phase 2
0.7853	Intermediate Similarity	NPD2095	Phase 2
0.7853	Intermediate Similarity	NPD2094	Phase 2
0.7822	Intermediate Similarity	NPD6987	Phase 1
0.7819	Intermediate Similarity	NPD482	Approved
0.7812	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD6242	Discontinued
0.7772	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD7470	Discontinued
0.7755	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2510	Approved
0.7707	Intermediate Similarity	NPD2509	Approved
0.7668	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD7666	Phase 3
0.7621	Intermediate Similarity	NPD7665	Phase 2
0.7614	Intermediate Similarity	NPD4499	Approved
0.761	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD750	Phase 2
0.7573	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8431	Approved
0.7476	Intermediate Similarity	NPD4852	Phase 2
0.7476	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD3947	Discontinued
0.7474	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2008	Discontinued
0.744	Intermediate Similarity	NPD7957	Phase 1
0.744	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2172	Phase 1
0.7431	Intermediate Similarity	NPD6164	Phase 2
0.7431	Intermediate Similarity	NPD6165	Phase 2
0.7427	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD5818	Discontinued
0.7406	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD2411	Approved
0.7389	Intermediate Similarity	NPD7948	Phase 1
0.7384	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD8073	Approved
0.7376	Intermediate Similarity	NPD7619	Phase 3
0.7376	Intermediate Similarity	NPD7944	Discontinued
0.7376	Intermediate Similarity	NPD7618	Phase 3
0.7371	Intermediate Similarity	NPD3393	Approved
0.7371	Intermediate Similarity	NPD3389	Approved
0.7371	Intermediate Similarity	NPD3394	Approved
0.7368	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4500	Approved
0.7366	Intermediate Similarity	NPD4501	Approved
0.7366	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7824	Approved
0.7358	Intermediate Similarity	NPD5065	Approved
0.7357	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6176	Phase 1
0.7343	Intermediate Similarity	NPD8072	Approved
0.7342	Intermediate Similarity	NPD7789	Approved
0.7342	Intermediate Similarity	NPD7952	Approved
0.7342	Intermediate Similarity	NPD7790	Approved
0.7342	Intermediate Similarity	NPD7953	Approved
0.7342	Intermediate Similarity	NPD7950	Approved
0.7342	Intermediate Similarity	NPD7791	Approved
0.7342	Intermediate Similarity	NPD7951	Approved
0.734	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4848	Phase 1
0.7317	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4601	Approved
0.7282	Intermediate Similarity	NPD4600	Approved
0.7282	Intermediate Similarity	NPD2144	Approved
0.7282	Intermediate Similarity	NPD484	Approved
0.7273	Intermediate Similarity	NPD7731	Approved
0.7273	Intermediate Similarity	NPD7730	Approved
0.7269	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7271	Approved
0.7248	Intermediate Similarity	NPD6995	Phase 1
0.7241	Intermediate Similarity	NPD1038	Approved
0.7241	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD2844	Phase 3
0.724	Intermediate Similarity	NPD7781	Approved
0.724	Intermediate Similarity	NPD7780	Approved
0.7238	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5482	Discontinued
0.7225	Intermediate Similarity	NPD8283	Approved
0.7225	Intermediate Similarity	NPD8282	Approved
0.7225	Intermediate Similarity	NPD56	Approved
0.7222	Intermediate Similarity	NPD3319	Phase 1
0.7222	Intermediate Similarity	NPD3318	Approved
0.7222	Intermediate Similarity	NPD3320	Approved
0.7222	Intermediate Similarity	NPD786	Approved
0.7212	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5473	Discontinued
0.7207	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6530	Approved
0.7203	Intermediate Similarity	NPD6531	Approved
0.7186	Intermediate Similarity	NPD7564	Discontinued
0.7181	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5088	Discontinued
0.7172	Intermediate Similarity	NPD3038	Discontinued
0.7169	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4076	Approved
0.7157	Intermediate Similarity	NPD4079	Approved
0.7151	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8093	Discontinued
0.715	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7603	Discontinued
0.7143	Intermediate Similarity	NPD1722	Approved
0.7143	Intermediate Similarity	NPD4075	Phase 2
0.7136	Intermediate Similarity	NPD5003	Discontinued
0.7136	Intermediate Similarity	NPD6664	Approved
0.7116	Intermediate Similarity	NPD8094	Discontinued
0.7116	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6479	Discontinued
0.7114	Intermediate Similarity	NPD6217	Discontinued
0.7107	Intermediate Similarity	NPD3505	Approved
0.7107	Intermediate Similarity	NPD3506	Approved
0.7098	Intermediate Similarity	NPD7688	Phase 1
0.7097	Intermediate Similarity	NPD3100	Discontinued
0.7092	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2837	Discontinued
0.7073	Intermediate Similarity	NPD802	Phase 2
0.707	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4429	Discontinued
0.7059	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2880	Discontinued
0.7048	Intermediate Similarity	NPD2879	Approved
0.7048	Intermediate Similarity	NPD2881	Approved
0.7042	Intermediate Similarity	NPD8399	Phase 1
0.7042	Intermediate Similarity	NPD8423	Phase 2
0.704	Intermediate Similarity	NPD4845	Discontinued
0.7039	Intermediate Similarity	NPD4602	Approved
0.7035	Intermediate Similarity	NPD2479	Phase 3
0.7035	Intermediate Similarity	NPD2481	Approved
0.7035	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD1325	Approved
0.7026	Intermediate Similarity	NPD1326	Approved
0.702	Intermediate Similarity	NPD7865	Approved
0.7019	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6178	Phase 3
0.701	Intermediate Similarity	NPD2639	Approved
0.701	Intermediate Similarity	NPD2642	Approved
0.7	Intermediate Similarity	NPD3178	Discontinued
0.6995	Remote Similarity	NPD3905	Phase 3
0.6995	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3323	Discontinued
0.699	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3825	Phase 3
0.6985	Remote Similarity	NPD8386	Phase 2
0.6981	Remote Similarity	NPD8272	Phase 2
0.6978	Remote Similarity	NPD4952	Phase 3
0.6977	Remote Similarity	NPD4051	Discontinued
0.6976	Remote Similarity	NPD2336	Approved
0.6974	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4462	Approved
0.6968	Remote Similarity	NPD3833	Phase 3
0.6968	Remote Similarity	NPD3835	Phase 3
0.6968	Remote Similarity	NPD4463	Approved
0.6966	Remote Similarity	NPD4558	Phase 2
0.6963	Remote Similarity	NPD2443	Approved
0.6963	Remote Similarity	NPD2442	Approved
0.6961	Remote Similarity	NPD1534	Approved
0.695	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5475	Discontinued
0.6944	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4922	Phase 2
0.6938	Remote Similarity	NPD4397	Phase 1
0.6933	Remote Similarity	NPD5559	Phase 2
0.693	Remote Similarity	NPD7941	Phase 3
0.6927	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7970	Approved
0.6926	Remote Similarity	NPD6790	Phase 1
0.6923	Remote Similarity	NPD8358	Approved
0.6919	Remote Similarity	NPD5017	Discontinued
0.6916	Remote Similarity	NPD8322	Phase 2
0.6916	Remote Similarity	NPD4885	Approved
0.6912	Remote Similarity	NPD4948	Discontinued
0.6912	Remote Similarity	NPD7454	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