NPASS Compound

Structure

NPC24589 OpenBabel07101719242D 32 36 0 0 1 0 0 0 0 0999 V2000 -3.1042 -0.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5279 3.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9927 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9437 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6869 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9927 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 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 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6379 1.8601 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.4789 3.1473 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7847 2.7872 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9437 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 29 1 0 0 0 0 3 9 1 0 0 0 0 4 8 1 0 0 0 0 4 17 1 0 0 0 0 5 20 2 0 0 0 0 5 21 1 0 0 0 0 6 22 2 0 0 0 0 6 23 1 0 0 0 0 7 3 1 6 0 0 0 7 11 1 0 0 0 0 7 31 1 0 0 0 0 8 16 1 6 0 0 0 8 30 1 0 0 0 0 9 18 1 1 0 0 0 9 30 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 32 1 6 0 0 0 12 15 1 0 0 0 0 12 28 1 1 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 23 1 6 0 0 0 15 31 1 0 0 0 0 16 24 2 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 1 0 0 0 18 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	453.15
Volume:	398.015
LogP:	-0.746
LogD:	-0.522
LogS:	-1.446
# Rotatable Bonds:	4
TPSA:	194.26
# H-Bond Aceptor:	14
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.246
Synthetic Accessibility Score:	5.322
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.352
MDCK Permeability:	2.11302176467143e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.971
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.399
Plasma Protein Binding (PPB):	26.08120346069336%
Volume Distribution (VD):	0.721
Pgp-substrate:	66.81340026855469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.819
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	5.012
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.938
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.666
Maximum Recommended Daily Dose:	0.406
Skin Sensitization:	0.232
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.372

Download Data

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

Natural Product: NPC24589

Natural Product ID:	NPC24589
*Common Name:**	AZYCCECPGKXFKD-WZBVYVGFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AZYCCECPGKXFKD-WZBVYVGFSA-N
Standard InCHI:	InChI=1S/C18H23N5O9/c1-28-12-11-7(31-15(12)23-6-22-10-13(19)20-5-21-14(10)23)3-9-18(27,32-11)17(25,26)4-8(30-9)16(24)29-2/h5-9,11-12,15,25-27H,3-4H2,1-2H3,(H2,19,20,21)/t7-,8+,9-,11+,12-,15-,18-/m1/s1
SMILES:	CO[C@@H]1[C@@H]2[C@@H](C[C@@H]3[C@@](C(C[C@@H](C(=O)OC)O3)(O)O)(O)O2)O[C@H]1n1cnc2c(N)ncnc12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109446
PubChem CID:	76310273
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002203] Glycosylamines

*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
NPO32887	Streptomyces sp. L-9-10	Species	Streptomycetaceae	Bacteria	organic extract	n.a.	n.a.	PMID[24533857]

☑ 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	2
Others	2

Activity Type	# Activity
Cell Line	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	13700.0	nM	PMID[497275]
NPT2	Others	Unspecified		IC50	=	2400.0	nM	PMID[497275]
NPT2	Others	Unspecified		Inhibition	=	45.1	%	PMID[497275]
NPT2	Others	Unspecified		Inhibition	=	96.2	%	PMID[497275]

☑ 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 NPC24589 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	470
0.1-0.2	6416
0.2-0.3	24124
0.3-0.4	9727
0.4-0.5	1635
0.5-0.6	207
0.6-0.7	66
0.7-0.8	43
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9819	High Similarity	NPC78941
0.9819	High Similarity	NPC282458
0.9106	High Similarity	NPC5802
0.9056	High Similarity	NPC157821
0.905	High Similarity	NPC276373
0.8314	Intermediate Similarity	NPC290959
0.7892	Intermediate Similarity	NPC309832
0.7892	Intermediate Similarity	NPC219313
0.7831	Intermediate Similarity	NPC189068
0.7771	Intermediate Similarity	NPC156461
0.7771	Intermediate Similarity	NPC21448
0.7771	Intermediate Similarity	NPC107374
0.7744	Intermediate Similarity	NPC317821
0.7725	Intermediate Similarity	NPC164665
0.7684	Intermediate Similarity	NPC325906
0.7679	Intermediate Similarity	NPC269827
0.7651	Intermediate Similarity	NPC229974
0.7627	Intermediate Similarity	NPC324484
0.7616	Intermediate Similarity	NPC302778
0.7616	Intermediate Similarity	NPC212551
0.7572	Intermediate Similarity	NPC174802
0.7571	Intermediate Similarity	NPC323091
0.753	Intermediate Similarity	NPC209525
0.753	Intermediate Similarity	NPC161659
0.7529	Intermediate Similarity	NPC224076
0.7527	Intermediate Similarity	NPC313897
0.7514	Intermediate Similarity	NPC130586
0.7514	Intermediate Similarity	NPC164952
0.75	Intermediate Similarity	NPC85689
0.75	Intermediate Similarity	NPC211025
0.75	Intermediate Similarity	NPC185991
0.7486	Intermediate Similarity	NPC226245
0.7486	Intermediate Similarity	NPC239737
0.7457	Intermediate Similarity	NPC321814
0.7457	Intermediate Similarity	NPC472816
0.744	Intermediate Similarity	NPC314152
0.7399	Intermediate Similarity	NPC161224
0.7386	Intermediate Similarity	NPC316618
0.7384	Intermediate Similarity	NPC136349
0.7365	Intermediate Similarity	NPC129756
0.7341	Intermediate Similarity	NPC150853
0.7326	Intermediate Similarity	NPC121222
0.7257	Intermediate Similarity	NPC328479
0.7257	Intermediate Similarity	NPC207633
0.7247	Intermediate Similarity	NPC195140
0.7243	Intermediate Similarity	NPC326529
0.7204	Intermediate Similarity	NPC324198
0.7204	Intermediate Similarity	NPC319100
0.7135	Intermediate Similarity	NPC313514
0.712	Intermediate Similarity	NPC326082
0.7112	Intermediate Similarity	NPC189261
0.7101	Intermediate Similarity	NPC33996
0.7095	Intermediate Similarity	NPC311197
0.7095	Intermediate Similarity	NPC313754
0.7095	Intermediate Similarity	NPC54320
0.7039	Intermediate Similarity	NPC52238
0.7	Intermediate Similarity	NPC93365
0.6982	Remote Similarity	NPC320818
0.6919	Remote Similarity	NPC261595
0.6882	Remote Similarity	NPC324033
0.6882	Remote Similarity	NPC321458
0.6778	Remote Similarity	NPC321052
0.6494	Remote Similarity	NPC61198
0.6484	Remote Similarity	NPC326694
0.6437	Remote Similarity	NPC262926
0.642	Remote Similarity	NPC30326
0.6389	Remote Similarity	NPC274384
0.6389	Remote Similarity	NPC89147
0.6354	Remote Similarity	NPC232408
0.6354	Remote Similarity	NPC64705
0.6333	Remote Similarity	NPC251233
0.6333	Remote Similarity	NPC211820
0.6327	Remote Similarity	NPC164845
0.6301	Remote Similarity	NPC246193
0.6298	Remote Similarity	NPC317746
0.6298	Remote Similarity	NPC177169
0.6286	Remote Similarity	NPC319221
0.6243	Remote Similarity	NPC318590
0.6239	Remote Similarity	NPC21461
0.623	Remote Similarity	NPC14590
0.6229	Remote Similarity	NPC324009
0.6222	Remote Similarity	NPC186619
0.6188	Remote Similarity	NPC315642
0.6188	Remote Similarity	NPC74306
0.617	Remote Similarity	NPC472834
0.6138	Remote Similarity	NPC472833
0.6126	Remote Similarity	NPC472832
0.6126	Remote Similarity	NPC18308
0.6096	Remote Similarity	NPC160666
0.6081	Remote Similarity	NPC250178
0.6051	Remote Similarity	NPC33382
0.6029	Remote Similarity	NPC265111
0.602	Remote Similarity	NPC125659
0.602	Remote Similarity	NPC168702
0.6017	Remote Similarity	NPC158055
0.599	Remote Similarity	NPC473585
0.596	Remote Similarity	NPC222174
0.5953	Remote Similarity	NPC103388
0.5846	Remote Similarity	NPC321393
0.5843	Remote Similarity	NPC104011
0.5826	Remote Similarity	NPC107160
0.5814	Remote Similarity	NPC327579
0.5812	Remote Similarity	NPC473646
0.5806	Remote Similarity	NPC217656
0.5793	Remote Similarity	NPC476564
0.5778	Remote Similarity	NPC57279
0.5775	Remote Similarity	NPC89139
0.5749	Remote Similarity	NPC150447
0.5739	Remote Similarity	NPC248007
0.5706	Remote Similarity	NPC174114
0.5706	Remote Similarity	NPC87981
0.5684	Remote Similarity	NPC244700
0.5676	Remote Similarity	NPC296437
0.5668	Remote Similarity	NPC476433
0.5668	Remote Similarity	NPC476528
0.565	Remote Similarity	NPC180493
0.5645	Remote Similarity	NPC470266
0.5638	Remote Similarity	NPC474986
0.5638	Remote Similarity	NPC476520
0.5638	Remote Similarity	NPC476522
0.5638	Remote Similarity	NPC324815
0.5638	Remote Similarity	NPC476013
0.5632	Remote Similarity	NPC476408
0.5608	Remote Similarity	NPC476521

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 NPC24589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1061
0.2-0.3	3290
0.3-0.4	2873
0.4-0.5	1391
0.5-0.6	265
0.6-0.7	88
0.7-0.8	25
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8222	Intermediate Similarity	NPD5683	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD5684	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD5682	Phase 3
0.8023	Intermediate Similarity	NPD3083	Approved
0.7929	Intermediate Similarity	NPD3107	Discontinued
0.7895	Intermediate Similarity	NPD2646	Discontinued
0.7771	Intermediate Similarity	NPD249	Approved
0.7771	Intermediate Similarity	NPD250	Approved
0.7684	Intermediate Similarity	NPD1777	Approved
0.7684	Intermediate Similarity	NPD1776	Approved
0.7679	Intermediate Similarity	NPD195	Approved
0.7679	Intermediate Similarity	NPD186	Discovery
0.7616	Intermediate Similarity	NPD1369	Phase 2
0.7586	Intermediate Similarity	NPD2624	Phase 2
0.7584	Intermediate Similarity	NPD7988	Suspended
0.7572	Intermediate Similarity	NPD339	Approved
0.7529	Intermediate Similarity	NPD169	Phase 2
0.7527	Intermediate Similarity	NPD5666	Phase 2
0.7514	Intermediate Similarity	NPD1750	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD338	Approved
0.75	Intermediate Similarity	NPD283	Approved
0.7444	Intermediate Similarity	NPD2647	Phase 3
0.744	Intermediate Similarity	NPD185	Approved
0.7414	Intermediate Similarity	NPD242	Approved
0.7386	Intermediate Similarity	NPD1732	Phase 3
0.7384	Intermediate Similarity	NPD548	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD166	Approved
0.7341	Intermediate Similarity	NPD3708	Phase 2
0.7321	Intermediate Similarity	NPD193	Suspended
0.7263	Intermediate Similarity	NPD6417	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7158	Phase 1
0.7204	Intermediate Similarity	NPD4171	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7138	Phase 2
0.7095	Intermediate Similarity	NPD219	Phase 3
0.7095	Intermediate Similarity	NPD220	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD217	Approved
0.7095	Intermediate Similarity	NPD216	Approved
0.7095	Intermediate Similarity	NPD218	Approved
0.7	Intermediate Similarity	NPD4716	Approved
0.7	Intermediate Similarity	NPD546	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1412	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4744	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD214	Approved
0.6927	Remote Similarity	NPD213	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3696	Approved
0.6919	Remote Similarity	NPD3695	Approved
0.6919	Remote Similarity	NPD247	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4240	Approved
0.6886	Remote Similarity	NPD248	Discontinued
0.6751	Remote Similarity	NPD2630	Approved
0.6751	Remote Similarity	NPD2631	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD2632	Approved
0.6722	Remote Similarity	NPD7842	Phase 2
0.6718	Remote Similarity	NPD1692	Approved
0.6627	Remote Similarity	NPD9633	Phase 3
0.6623	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD9632	Phase 3
0.6568	Remote Similarity	NPD870	Clinical (unspecified phase)
0.655	Remote Similarity	NPD4054	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8375	Approved
0.6538	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD549	Approved
0.6494	Remote Similarity	NPD252	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.645	Remote Similarity	NPD9408	Phase 3
0.6429	Remote Similarity	NPD2876	Phase 3
0.6429	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7323	Phase 2
0.6402	Remote Similarity	NPD2902	Phase 2
0.6402	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2824	Phase 2
0.6359	Remote Similarity	NPD5080	Phase 2
0.633	Remote Similarity	NPD4074	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD5079	Phase 2
0.6313	Remote Similarity	NPD1430	Approved
0.6313	Remote Similarity	NPD1431	Approved
0.6304	Remote Similarity	NPD3085	Phase 1
0.627	Remote Similarity	NPD3086	Phase 3
0.6255	Remote Similarity	NPD6023	Discontinued
0.625	Remote Similarity	NPD194	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD536	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD582	Approved
0.6175	Remote Similarity	NPD1730	Discontinued
0.6145	Remote Similarity	NPD1808	Phase 1
0.6124	Remote Similarity	NPD1120	Approved
0.6124	Remote Similarity	NPD1121	Approved
0.612	Remote Similarity	NPD171	Discontinued
0.61	Remote Similarity	NPD1046	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD231	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD9605	Phase 3
0.6017	Remote Similarity	NPD6840	Approved
0.6009	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD4495	Phase 1
0.6009	Remote Similarity	NPD4458	Phase 2
0.5959	Remote Similarity	NPD5321	Phase 3
0.5956	Remote Similarity	NPD2253	Discontinued
0.5944	Remote Similarity	NPD535	Approved
0.5922	Remote Similarity	NPD1063	Phase 2
0.59	Remote Similarity	NPD8250	Phase 2
0.5899	Remote Similarity	NPD282	Approved
0.5897	Remote Similarity	NPD8409	Suspended
0.5889	Remote Similarity	NPD1119	Phase 2
0.5855	Remote Similarity	NPD5337	Phase 1
0.5855	Remote Similarity	NPD5336	Phase 1
0.5848	Remote Similarity	NPD9606	Approved
0.5842	Remote Similarity	NPD353	Discontinued
0.5833	Remote Similarity	NPD1058	Discontinued
0.5833	Remote Similarity	NPD5486	Discontinued
0.5816	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD9607	Approved
0.5806	Remote Similarity	NPD4714	Approved
0.5806	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD34	Approved
0.5806	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD5458	Discontinued
0.5746	Remote Similarity	NPD209	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD9084	Phase 2
0.5738	Remote Similarity	NPD6112	Approved
0.5732	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.573	Remote Similarity	NPD1128	Approved
0.573	Remote Similarity	NPD1127	Approved
0.5678	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD9584	Phase 2
0.5665	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.565	Remote Similarity	NPD78	Approved
0.565	Remote Similarity	NPD9544	Approved
0.5639	Remote Similarity	NPD8271	Discontinued
0.5636	Remote Similarity	NPD7103	Approved
0.5618	Remote Similarity	NPD281	Approved
0.5604	Remote Similarity	NPD547	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