NPASS Compound

Structure

NPC471080 OpenBabel07101718312D 28 32 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0734 2.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0844 2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0898 2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 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 -4.2654 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6722 1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 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 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6667 1.6226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 28 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 24 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 25 1 0 0 0 0 12 22 1 0 0 0 0 12 24 1 0 0 0 0 14 24 1 1 0 0 0 15 28 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 6 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 21 22 1 6 0 0 0 21 26 1 0 0 0 0 22 25 1 1 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.22
Volume:	392.465
LogP:	3.246
LogD:	3.124
LogS:	-2.426
# Rotatable Bonds:	2
TPSA:	71.96
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.696
Synthetic Accessibility Score:	4.358
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.169
MDCK Permeability:	1.050146238412708e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.956
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.438
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.929
Plasma Protein Binding (PPB):	75.34029388427734%
Volume Distribution (VD):	2.084
Pgp-substrate:	17.67774200439453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.274
CYP2C19-inhibitor:	0.226
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.393
CYP2D6-inhibitor:	0.669
CYP2D6-substrate:	0.719
CYP3A4-inhibitor:	0.639
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	8.711
Half-life (T1/2):	0.474

ADMET: Toxicity

hERG Blockers:	0.826
Human Hepatotoxicity (H-HT):	0.986
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.448
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.112
Carcinogencity:	0.307
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC471080

Natural Product ID:	NPC471080
*Common Name:**	YZJBCQWDGRNRAY-UPOGBMBOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YZJBCQWDGRNRAY-UPOGBMBOSA-N
Standard InCHI:	InChI=1S/C22H29N3O3/c1-13(2)9-18-20-19(16-7-6-15(28-3)10-17(16)23-20)21(26)22(27)12-24-8-4-5-14(24)11-25(18)22/h6-7,9-10,14,18,21,23,26-27H,4-5,8,11-12H2,1-3H3/t14-,18+,21-,22+/m0/s1
SMILES:	COc1ccc2c(c1)[nH]c1c2[C@H](O)[C@]2(N([C@@H]1C=C(C)C)C[C@H]1N(C2)CCC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2367464
PubChem CID:	73348278
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	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	4
MIC	4
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	4
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT470	Individual Protein	Rhodesain	Trypanosoma brucei rhodesiense	IC50	=	10900.0	nM	PMID[526864]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	97200.0	nM	PMID[526864]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	6400.0	nM	PMID[526864]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[526864]
NPT2	Others	Unspecified		Ratio IC50	=	17.6	uM	PMID[526864]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	304000.0	nM	PMID[526864]
NPT610	Others	Molecular identity unknown		MIC	=	60800.0	nM	PMID[526864]

☑ 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 NPC471080 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	416
0.1-0.2	2212
0.2-0.3	13427
0.3-0.4	6737
0.4-0.5	13395
0.5-0.6	3613
0.6-0.7	2173
0.7-0.8	655
0.8-0.85	57
0.85-0.9	8
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469592
0.9793	High Similarity	NPC469594
0.9479	High Similarity	NPC469589
0.9031	High Similarity	NPC475910
0.9	High Similarity	NPC470784
0.8863	High Similarity	NPC184680
0.8821	High Similarity	NPC470785
0.8676	High Similarity	NPC305984
0.8634	High Similarity	NPC303658
0.8579	High Similarity	NPC329747
0.8502	High Similarity	NPC213530
0.8502	High Similarity	NPC193267
0.8485	Intermediate Similarity	NPC249040
0.8429	Intermediate Similarity	NPC84478
0.8387	Intermediate Similarity	NPC474183
0.8381	Intermediate Similarity	NPC280272
0.8366	Intermediate Similarity	NPC472111
0.8358	Intermediate Similarity	NPC223427
0.8357	Intermediate Similarity	NPC148183
0.8357	Intermediate Similarity	NPC152768
0.8333	Intermediate Similarity	NPC243834
0.8333	Intermediate Similarity	NPC70956
0.831	Intermediate Similarity	NPC473185
0.8302	Intermediate Similarity	NPC21638
0.83	Intermediate Similarity	NPC329793
0.8293	Intermediate Similarity	NPC167860
0.8293	Intermediate Similarity	NPC123976
0.8276	Intermediate Similarity	NPC476106
0.8271	Intermediate Similarity	NPC194740
0.8259	Intermediate Similarity	NPC232727
0.8227	Intermediate Similarity	NPC285558
0.8224	Intermediate Similarity	NPC110151
0.8218	Intermediate Similarity	NPC135887
0.8218	Intermediate Similarity	NPC199277
0.8203	Intermediate Similarity	NPC473105
0.8199	Intermediate Similarity	NPC132642
0.8182	Intermediate Similarity	NPC183407
0.8174	Intermediate Similarity	NPC473183
0.8152	Intermediate Similarity	NPC473179
0.8128	Intermediate Similarity	NPC475085
0.8128	Intermediate Similarity	NPC475112
0.8128	Intermediate Similarity	NPC291535
0.8125	Intermediate Similarity	NPC316981
0.8125	Intermediate Similarity	NPC72980
0.8102	Intermediate Similarity	NPC314954
0.8086	Intermediate Similarity	NPC478074
0.8082	Intermediate Similarity	NPC473184
0.8075	Intermediate Similarity	NPC310118
0.8073	Intermediate Similarity	NPC469554
0.8069	Intermediate Similarity	NPC18487
0.8058	Intermediate Similarity	NPC193777
0.8038	Intermediate Similarity	NPC264176
0.802	Intermediate Similarity	NPC72211
0.8019	Intermediate Similarity	NPC473041
0.801	Intermediate Similarity	NPC251090
0.8009	Intermediate Similarity	NPC170114
0.8	Intermediate Similarity	NPC176127
0.7991	Intermediate Similarity	NPC60621
0.7991	Intermediate Similarity	NPC477532
0.7981	Intermediate Similarity	NPC476116
0.7964	Intermediate Similarity	NPC295228
0.7962	Intermediate Similarity	NPC470549
0.796	Intermediate Similarity	NPC131017
0.7952	Intermediate Similarity	NPC94157
0.7949	Intermediate Similarity	NPC314394
0.7947	Intermediate Similarity	NPC317430
0.7943	Intermediate Similarity	NPC11464
0.7943	Intermediate Similarity	NPC5145
0.7929	Intermediate Similarity	NPC46580
0.7921	Intermediate Similarity	NPC70259
0.7915	Intermediate Similarity	NPC266931
0.7913	Intermediate Similarity	NPC162484
0.791	Intermediate Similarity	NPC307963
0.7908	Intermediate Similarity	NPC139291
0.7908	Intermediate Similarity	NPC472108
0.7892	Intermediate Similarity	NPC128823
0.7874	Intermediate Similarity	NPC118832
0.7874	Intermediate Similarity	NPC264166
0.7874	Intermediate Similarity	NPC274291
0.7874	Intermediate Similarity	NPC470500
0.7874	Intermediate Similarity	NPC329708
0.7874	Intermediate Similarity	NPC165349
0.7874	Intermediate Similarity	NPC47059
0.7873	Intermediate Similarity	NPC473182
0.7871	Intermediate Similarity	NPC43787
0.7871	Intermediate Similarity	NPC205934
0.7867	Intermediate Similarity	NPC472098
0.7867	Intermediate Similarity	NPC48353
0.7864	Intermediate Similarity	NPC475253
0.786	Intermediate Similarity	NPC477533
0.7857	Intermediate Similarity	NPC471304
0.7854	Intermediate Similarity	NPC19872
0.7854	Intermediate Similarity	NPC176538
0.784	Intermediate Similarity	NPC330009
0.7833	Intermediate Similarity	NPC13880
0.7828	Intermediate Similarity	NPC94943
0.7828	Intermediate Similarity	NPC101543
0.7824	Intermediate Similarity	NPC472123
0.7816	Intermediate Similarity	NPC476044
0.7811	Intermediate Similarity	NPC92111
0.7808	Intermediate Similarity	NPC470126
0.7788	Intermediate Similarity	NPC162748
0.7783	Intermediate Similarity	NPC26679
0.7778	Intermediate Similarity	NPC190007
0.7778	Intermediate Similarity	NPC472099
0.7778	Intermediate Similarity	NPC62069
0.7778	Intermediate Similarity	NPC295898
0.7778	Intermediate Similarity	NPC477861
0.7773	Intermediate Similarity	NPC252251
0.7773	Intermediate Similarity	NPC253580
0.7761	Intermediate Similarity	NPC76748
0.7757	Intermediate Similarity	NPC470799
0.7757	Intermediate Similarity	NPC8022
0.7756	Intermediate Similarity	NPC306376
0.7755	Intermediate Similarity	NPC133261
0.7749	Intermediate Similarity	NPC189079
0.7748	Intermediate Similarity	NPC474192
0.7748	Intermediate Similarity	NPC475720
0.7734	Intermediate Similarity	NPC79293
0.7734	Intermediate Similarity	NPC279401
0.7732	Intermediate Similarity	NPC474409
0.7729	Intermediate Similarity	NPC267423
0.7727	Intermediate Similarity	NPC212535
0.7725	Intermediate Similarity	NPC209769
0.7721	Intermediate Similarity	NPC304926
0.7721	Intermediate Similarity	NPC476041
0.7719	Intermediate Similarity	NPC81939
0.7711	Intermediate Similarity	NPC296527
0.7703	Intermediate Similarity	NPC477531
0.7703	Intermediate Similarity	NPC475070
0.77	Intermediate Similarity	NPC294620
0.7696	Intermediate Similarity	NPC63971
0.7696	Intermediate Similarity	NPC91868
0.7696	Intermediate Similarity	NPC128115
0.7692	Intermediate Similarity	NPC471762
0.7689	Intermediate Similarity	NPC199667
0.7686	Intermediate Similarity	NPC475666
0.7685	Intermediate Similarity	NPC96321
0.7681	Intermediate Similarity	NPC315957
0.7681	Intermediate Similarity	NPC121772
0.7678	Intermediate Similarity	NPC470931
0.7667	Intermediate Similarity	NPC474145
0.7667	Intermediate Similarity	NPC475841
0.7665	Intermediate Similarity	NPC472443
0.7658	Intermediate Similarity	NPC209174
0.7656	Intermediate Similarity	NPC475774
0.7656	Intermediate Similarity	NPC476138
0.7656	Intermediate Similarity	NPC245816
0.7656	Intermediate Similarity	NPC476098
0.7655	Intermediate Similarity	NPC101350
0.7653	Intermediate Similarity	NPC87413
0.7644	Intermediate Similarity	NPC473187
0.7642	Intermediate Similarity	NPC201697
0.7642	Intermediate Similarity	NPC185782
0.7642	Intermediate Similarity	NPC174758
0.7642	Intermediate Similarity	NPC473181
0.7638	Intermediate Similarity	NPC472109
0.7638	Intermediate Similarity	NPC472444
0.7638	Intermediate Similarity	NPC472110
0.7629	Intermediate Similarity	NPC133609
0.7621	Intermediate Similarity	NPC153042
0.7619	Intermediate Similarity	NPC470930
0.7617	Intermediate Similarity	NPC112206
0.7617	Intermediate Similarity	NPC202605
0.7615	Intermediate Similarity	NPC150239
0.7614	Intermediate Similarity	NPC283152
0.7611	Intermediate Similarity	NPC235685
0.7602	Intermediate Similarity	NPC202503
0.7598	Intermediate Similarity	NPC99666
0.7591	Intermediate Similarity	NPC122436
0.757	Intermediate Similarity	NPC208284
0.7568	Intermediate Similarity	NPC261251
0.7568	Intermediate Similarity	NPC6215
0.755	Intermediate Similarity	NPC19679
0.7548	Intermediate Similarity	NPC32200
0.7547	Intermediate Similarity	NPC249583
0.7545	Intermediate Similarity	NPC260434
0.7544	Intermediate Similarity	NPC475816
0.7537	Intermediate Similarity	NPC242928
0.7535	Intermediate Similarity	NPC203168
0.7534	Intermediate Similarity	NPC100547
0.7534	Intermediate Similarity	NPC66777
0.7534	Intermediate Similarity	NPC311906
0.7525	Intermediate Similarity	NPC171171
0.7525	Intermediate Similarity	NPC96890
0.7525	Intermediate Similarity	NPC326575
0.7524	Intermediate Similarity	NPC326634
0.7523	Intermediate Similarity	NPC214142
0.7523	Intermediate Similarity	NPC247803
0.7523	Intermediate Similarity	NPC227908
0.7523	Intermediate Similarity	NPC173080
0.7523	Intermediate Similarity	NPC24370
0.7523	Intermediate Similarity	NPC319232
0.7513	Intermediate Similarity	NPC329688
0.7513	Intermediate Similarity	NPC26872
0.7513	Intermediate Similarity	NPC189812
0.7512	Intermediate Similarity	NPC288349
0.7512	Intermediate Similarity	NPC324149
0.7512	Intermediate Similarity	NPC469928
0.7512	Intermediate Similarity	NPC472294

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 NPC471080 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	586
0.2-0.3	835
0.3-0.4	1146
0.4-0.5	2466
0.5-0.6	2583
0.6-0.7	1101
0.7-0.8	211
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8737	High Similarity	NPD3003	Approved
0.865	High Similarity	NPD5658	Approved
0.8622	High Similarity	NPD1768	Approved
0.8592	High Similarity	NPD7194	Discontinued
0.8398	Intermediate Similarity	NPD5902	Approved
0.8398	Intermediate Similarity	NPD5903	Approved
0.8325	Intermediate Similarity	NPD1392	Approved
0.8287	Intermediate Similarity	NPD7558	Phase 2
0.8278	Intermediate Similarity	NPD6985	Discontinued
0.8159	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD7222	Phase 2
0.805	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD4203	Approved
0.8041	Intermediate Similarity	NPD4204	Approved
0.8009	Intermediate Similarity	NPD5612	Discontinued
0.799	Intermediate Similarity	NPD4502	Phase 2
0.7972	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD1038	Approved
0.7909	Intermediate Similarity	NPD4885	Approved
0.7885	Intermediate Similarity	NPD7452	Approved
0.7885	Intermediate Similarity	NPD7453	Approved
0.7874	Intermediate Similarity	NPD4033	Approved
0.7874	Intermediate Similarity	NPD4122	Approved
0.7874	Intermediate Similarity	NPD4039	Approved
0.7874	Intermediate Similarity	NPD4035	Approved
0.7874	Intermediate Similarity	NPD4038	Approved
0.7874	Intermediate Similarity	NPD4036	Approved
0.7874	Intermediate Similarity	NPD4037	Approved
0.7874	Intermediate Similarity	NPD4034	Approved
0.7874	Intermediate Similarity	NPD32	Approved
0.7874	Intermediate Similarity	NPD31	Approved
0.7871	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD5067	Phase 2
0.782	Intermediate Similarity	NPD5066	Phase 2
0.7788	Intermediate Similarity	NPD4795	Phase 2
0.7751	Intermediate Similarity	NPD8403	Phase 1
0.775	Intermediate Similarity	NPD2383	Phase 1
0.7739	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2176	Approved
0.7718	Intermediate Similarity	NPD2175	Phase 3
0.7718	Intermediate Similarity	NPD2177	Approved
0.7706	Intermediate Similarity	NPD7219	Approved
0.7706	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7221	Approved
0.77	Intermediate Similarity	NPD5256	Discontinued
0.7699	Intermediate Similarity	NPD8363	Approved
0.7699	Intermediate Similarity	NPD8364	Approved
0.7688	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD5632	Approved
0.7685	Intermediate Similarity	NPD6569	Phase 2
0.7682	Intermediate Similarity	NPD7674	Phase 3
0.7682	Intermediate Similarity	NPD7675	Phase 3
0.7682	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD1740	Approved
0.7681	Intermediate Similarity	NPD1739	Approved
0.7667	Intermediate Similarity	NPD5530	Phase 1
0.7653	Intermediate Similarity	NPD3570	Phase 2
0.7638	Intermediate Similarity	NPD5596	Phase 2
0.7635	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD7948	Phase 1
0.7602	Intermediate Similarity	NPD7426	Phase 1
0.7563	Intermediate Similarity	NPD2382	Approved
0.7563	Intermediate Similarity	NPD2380	Approved
0.7563	Intermediate Similarity	NPD2381	Approved
0.7557	Intermediate Similarity	NPD6246	Approved
0.7549	Intermediate Similarity	NPD5913	Phase 3
0.7549	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD5930	Phase 3
0.7511	Intermediate Similarity	NPD7956	Approved
0.7511	Intermediate Similarity	NPD7955	Approved
0.7488	Intermediate Similarity	NPD5939	Approved
0.7488	Intermediate Similarity	NPD5936	Approved
0.7478	Intermediate Similarity	NPD6494	Phase 2
0.7476	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD802	Phase 2
0.7455	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5559	Phase 2
0.7454	Intermediate Similarity	NPD3330	Phase 1
0.7443	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6590	Discontinued
0.744	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4418	Discontinued
0.7439	Intermediate Similarity	NPD8466	Approved
0.7439	Intermediate Similarity	NPD8465	Approved
0.7439	Intermediate Similarity	NPD8467	Approved
0.7422	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3037	Phase 1
0.7409	Intermediate Similarity	NPD3402	Phase 1
0.7409	Intermediate Similarity	NPD3875	Discontinued
0.7407	Intermediate Similarity	NPD6220	Phase 3
0.7403	Intermediate Similarity	NPD6517	Phase 3
0.74	Intermediate Similarity	NPD3920	Phase 2
0.7385	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6290	Phase 2
0.7381	Intermediate Similarity	NPD3825	Phase 3
0.7373	Intermediate Similarity	NPD3815	Phase 1
0.7373	Intermediate Similarity	NPD3816	Phase 1
0.7368	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6244	Phase 3
0.7362	Intermediate Similarity	NPD6243	Phase 3
0.736	Intermediate Similarity	NPD1325	Approved
0.736	Intermediate Similarity	NPD1326	Approved
0.7357	Intermediate Similarity	NPD7796	Approved
0.7357	Intermediate Similarity	NPD7797	Approved
0.7355	Intermediate Similarity	NPD7803	Approved
0.7349	Intermediate Similarity	NPD2916	Discontinued
0.7348	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4500	Approved
0.7346	Intermediate Similarity	NPD4501	Approved
0.7346	Intermediate Similarity	NPD4600	Approved
0.7346	Intermediate Similarity	NPD4601	Approved
0.7345	Intermediate Similarity	NPD8512	Phase 3
0.7342	Intermediate Similarity	NPD7726	Phase 1
0.7333	Intermediate Similarity	NPD5140	Approved
0.7333	Intermediate Similarity	NPD5138	Approved
0.7325	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6991	Approved
0.7321	Intermediate Similarity	NPD3477	Phase 2
0.7321	Intermediate Similarity	NPD5512	Phase 3
0.7321	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8426	Approved
0.732	Intermediate Similarity	NPD8425	Approved
0.732	Intermediate Similarity	NPD8459	Approved
0.732	Intermediate Similarity	NPD8460	Approved
0.7316	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD8016	Phase 3
0.731	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8359	Phase 2
0.7306	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4548	Discontinued
0.7299	Intermediate Similarity	NPD5547	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2151	Approved
0.7298	Intermediate Similarity	NPD8427	Approved
0.7298	Intermediate Similarity	NPD8428	Approved
0.7298	Intermediate Similarity	NPD8429	Approved
0.7296	Intermediate Similarity	NPD7068	Approved
0.7296	Intermediate Similarity	NPD7067	Approved
0.7288	Intermediate Similarity	NPD5482	Discontinued
0.7286	Intermediate Similarity	NPD5003	Discontinued
0.7284	Intermediate Similarity	NPD8284	Discontinued
0.7281	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD8244	Phase 2
0.7277	Intermediate Similarity	NPD8358	Approved
0.7269	Intermediate Similarity	NPD2187	Approved
0.7269	Intermediate Similarity	NPD2189	Approved
0.7264	Intermediate Similarity	NPD6159	Phase 2
0.726	Intermediate Similarity	NPD3923	Approved
0.726	Intermediate Similarity	NPD3922	Approved
0.726	Intermediate Similarity	NPD3924	Approved
0.726	Intermediate Similarity	NPD3921	Approved
0.7257	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5065	Approved
0.7249	Intermediate Similarity	NPD4080	Discontinued
0.7248	Intermediate Similarity	NPD4131	Phase 3
0.7241	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD5164	Discontinued
0.7235	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1034	Phase 3
0.7233	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1954	Phase 1
0.723	Intermediate Similarity	NPD4511	Phase 1
0.7227	Intermediate Similarity	NPD4897	Phase 2
0.7225	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6242	Discontinued
0.7217	Intermediate Similarity	NPD3814	Phase 1
0.7213	Intermediate Similarity	NPD3343	Phase 3
0.7208	Intermediate Similarity	NPD8255	Phase 2
0.7198	Intermediate Similarity	NPD4021	Phase 2
0.7196	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5479	Discontinued
0.7191	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7708	Approved
0.7189	Intermediate Similarity	NPD7671	Approved
0.7189	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7672	Approved
0.7186	Intermediate Similarity	NPD4454	Phase 2
0.7186	Intermediate Similarity	NPD3006	Discontinued
0.7183	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6978	Phase 2
0.7181	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6473	Phase 1
0.7176	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7470	Discontinued
0.7169	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8442	Discontinued
0.7156	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6550	Discontinued
0.7155	Intermediate Similarity	NPD7859	Phase 2
0.715	Intermediate Similarity	NPD6592	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