NPASS Compound

Structure

NPC472285 OpenBabel07101718322D 24 26 0 0 1 0 0 0 0 0999 V2000 -4.2346 -2.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1006 -1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3686 -1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1006 -0.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 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 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0322 0.5862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0839 1.4826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6254 -0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3686 -0.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2346 -0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2749 2.0704 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6386 1.6637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0267 0.4817 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 -1.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9975 1.8893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3795 3.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4476 2.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 14 2 0 0 0 0 4 15 2 0 0 0 0 5 6 1 0 0 0 0 5 13 2 0 0 0 0 6 16 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 21 2 0 0 0 0 11 17 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 1 0 0 0 18 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.14
Volume:	332.914
LogP:	0.739
LogD:	0.512
LogS:	-1.714
# Rotatable Bonds:	7
TPSA:	98.48
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.525
Synthetic Accessibility Score:	3.325
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.934
MDCK Permeability:	3.8056102766859112e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.139
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.361
Plasma Protein Binding (PPB):	47.323116302490234%
Volume Distribution (VD):	1.21
Pgp-substrate:	55.47370147705078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.28
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.091
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.303
CYP2D6-inhibitor:	0.374
CYP2D6-substrate:	0.857
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	2.325
Half-life (T1/2):	0.969

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.166
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.164
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.048
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC472285

Natural Product ID:	NPC472285
*Common Name:**	ZRBCSTRGKLTTKW-MSOLQXFVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZRBCSTRGKLTTKW-MSOLQXFVSA-N
Standard InCHI:	InChI=1S/C18H20N2O4/c21-10-13-5-6-16(18(24)17(23)11-22)20(13)8-7-12-9-19-15-4-2-1-3-14(12)15/h1-6,9-10,17-19,22-24H,7-8,11H2/t17-,18+/m1/s1
SMILES:	C1=CC=C2C(=C1)C(=CN2)CCN3C(=CC=C3C(C(CO)O)O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357674
PubChem CID:	n.a.
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
NPO33301	jiangella gansuensis	Species	Jiangellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25412141]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	60700.0	nM	PMID[523162]

☑ 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 NPC472285 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	356
0.1-0.2	2678
0.2-0.3	13490
0.3-0.4	16535
0.4-0.5	4911
0.5-0.6	2044
0.6-0.7	2090
0.7-0.8	571
0.8-0.85	20
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.867	High Similarity	NPC82370
0.8382	Intermediate Similarity	NPC244741
0.8325	Intermediate Similarity	NPC36405
0.831	Intermediate Similarity	NPC229893
0.8259	Intermediate Similarity	NPC131887
0.8199	Intermediate Similarity	NPC312645
0.8168	Intermediate Similarity	NPC472284
0.8146	Intermediate Similarity	NPC165599
0.8145	Intermediate Similarity	NPC15801
0.8143	Intermediate Similarity	NPC89508
0.8098	Intermediate Similarity	NPC57398
0.809	Intermediate Similarity	NPC154339
0.809	Intermediate Similarity	NPC83111
0.806	Intermediate Similarity	NPC267343
0.803	Intermediate Similarity	NPC315555
0.8009	Intermediate Similarity	NPC118940
0.8	Intermediate Similarity	NPC276657
0.799	Intermediate Similarity	NPC278434
0.7972	Intermediate Similarity	NPC229348
0.7941	Intermediate Similarity	NPC227582
0.7928	Intermediate Similarity	NPC70155
0.7907	Intermediate Similarity	NPC264285
0.7902	Intermediate Similarity	NPC67288
0.7895	Intermediate Similarity	NPC472286
0.7895	Intermediate Similarity	NPC472287
0.7892	Intermediate Similarity	NPC316411
0.7867	Intermediate Similarity	NPC162860
0.7861	Intermediate Similarity	NPC321708
0.7861	Intermediate Similarity	NPC209917
0.7857	Intermediate Similarity	NPC88008
0.7857	Intermediate Similarity	NPC183777
0.7857	Intermediate Similarity	NPC111275
0.7857	Intermediate Similarity	NPC46225
0.7854	Intermediate Similarity	NPC476818
0.7854	Intermediate Similarity	NPC141454
0.7844	Intermediate Similarity	NPC16352
0.784	Intermediate Similarity	NPC151976
0.7839	Intermediate Similarity	NPC207851
0.7838	Intermediate Similarity	NPC267853
0.7826	Intermediate Similarity	NPC252338
0.782	Intermediate Similarity	NPC127677
0.782	Intermediate Similarity	NPC171787
0.7817	Intermediate Similarity	NPC283219
0.7803	Intermediate Similarity	NPC244897
0.7783	Intermediate Similarity	NPC478158
0.7778	Intermediate Similarity	NPC74413
0.7773	Intermediate Similarity	NPC54420
0.7767	Intermediate Similarity	NPC478157
0.7767	Intermediate Similarity	NPC477979
0.776	Intermediate Similarity	NPC102423
0.7758	Intermediate Similarity	NPC315062
0.7757	Intermediate Similarity	NPC219087
0.7751	Intermediate Similarity	NPC260900
0.7751	Intermediate Similarity	NPC328596
0.7751	Intermediate Similarity	NPC328318
0.7751	Intermediate Similarity	NPC476874
0.774	Intermediate Similarity	NPC470497
0.7731	Intermediate Similarity	NPC204491
0.7729	Intermediate Similarity	NPC470499
0.7727	Intermediate Similarity	NPC126709
0.7727	Intermediate Similarity	NPC248041
0.7723	Intermediate Similarity	NPC207686
0.7723	Intermediate Similarity	NPC17059
0.7714	Intermediate Similarity	NPC98715
0.7706	Intermediate Similarity	NPC107836
0.7703	Intermediate Similarity	NPC471944
0.7703	Intermediate Similarity	NPC300183
0.7703	Intermediate Similarity	NPC475506
0.7696	Intermediate Similarity	NPC476460
0.7696	Intermediate Similarity	NPC138370
0.7692	Intermediate Similarity	NPC474767
0.7689	Intermediate Similarity	NPC225821
0.7677	Intermediate Similarity	NPC284775
0.7677	Intermediate Similarity	NPC145885
0.7677	Intermediate Similarity	NPC84827
0.7677	Intermediate Similarity	NPC14113
0.7674	Intermediate Similarity	NPC87856
0.7673	Intermediate Similarity	NPC235684
0.7671	Intermediate Similarity	NPC14686
0.7669	Intermediate Similarity	NPC258048
0.7667	Intermediate Similarity	NPC193761
0.7667	Intermediate Similarity	NPC476073
0.7667	Intermediate Similarity	NPC155143
0.7665	Intermediate Similarity	NPC149155
0.7665	Intermediate Similarity	NPC203468
0.7665	Intermediate Similarity	NPC110500
0.7664	Intermediate Similarity	NPC123839
0.7656	Intermediate Similarity	NPC131718
0.7656	Intermediate Similarity	NPC315491
0.7656	Intermediate Similarity	NPC45459
0.7656	Intermediate Similarity	NPC213308
0.7653	Intermediate Similarity	NPC314957
0.7653	Intermediate Similarity	NPC266249
0.7653	Intermediate Similarity	NPC258062
0.765	Intermediate Similarity	NPC71037
0.7644	Intermediate Similarity	NPC89987
0.7644	Intermediate Similarity	NPC149708
0.7639	Intermediate Similarity	NPC267965
0.7626	Intermediate Similarity	NPC269270
0.7626	Intermediate Similarity	NPC267885
0.7624	Intermediate Similarity	NPC241025
0.7623	Intermediate Similarity	NPC192712
0.7621	Intermediate Similarity	NPC477549
0.7617	Intermediate Similarity	NPC271862
0.7617	Intermediate Similarity	NPC61038
0.7614	Intermediate Similarity	NPC313791
0.7612	Intermediate Similarity	NPC48938
0.7612	Intermediate Similarity	NPC159125
0.7612	Intermediate Similarity	NPC469358
0.7604	Intermediate Similarity	NPC230869
0.76	Intermediate Similarity	NPC475969
0.76	Intermediate Similarity	NPC475859
0.76	Intermediate Similarity	NPC474877
0.7598	Intermediate Similarity	NPC75544
0.7598	Intermediate Similarity	NPC221873
0.7598	Intermediate Similarity	NPC213629
0.7593	Intermediate Similarity	NPC110182
0.7589	Intermediate Similarity	NPC33949
0.7585	Intermediate Similarity	NPC202812
0.7578	Intermediate Similarity	NPC319232
0.7578	Intermediate Similarity	NPC24370
0.7577	Intermediate Similarity	NPC297642
0.7569	Intermediate Similarity	NPC132211
0.7569	Intermediate Similarity	NPC203614
0.7562	Intermediate Similarity	NPC314394
0.756	Intermediate Similarity	NPC473640
0.756	Intermediate Similarity	NPC171317
0.7559	Intermediate Similarity	NPC317373
0.7559	Intermediate Similarity	NPC175602
0.7558	Intermediate Similarity	NPC54744
0.7556	Intermediate Similarity	NPC470730
0.7556	Intermediate Similarity	NPC477176
0.7556	Intermediate Similarity	NPC470729
0.7556	Intermediate Similarity	NPC477175
0.7551	Intermediate Similarity	NPC78020
0.755	Intermediate Similarity	NPC55772
0.7548	Intermediate Similarity	NPC292361
0.7546	Intermediate Similarity	NPC320968
0.7544	Intermediate Similarity	NPC57453
0.7537	Intermediate Similarity	NPC163421
0.7537	Intermediate Similarity	NPC15102
0.7537	Intermediate Similarity	NPC188387
0.7536	Intermediate Similarity	NPC304203
0.7535	Intermediate Similarity	NPC223791
0.7535	Intermediate Similarity	NPC107077
0.7534	Intermediate Similarity	NPC27041
0.7533	Intermediate Similarity	NPC63279
0.7524	Intermediate Similarity	NPC100321
0.7523	Intermediate Similarity	NPC474412
0.7523	Intermediate Similarity	NPC270918
0.7522	Intermediate Similarity	NPC477177
0.7512	Intermediate Similarity	NPC75634
0.7512	Intermediate Similarity	NPC207020
0.7512	Intermediate Similarity	NPC327592
0.7511	Intermediate Similarity	NPC194740
0.75	Intermediate Similarity	NPC39370
0.75	Intermediate Similarity	NPC5145
0.75	Intermediate Similarity	NPC62749
0.75	Intermediate Similarity	NPC281049
0.749	Intermediate Similarity	NPC74619
0.7489	Intermediate Similarity	NPC471192
0.7489	Intermediate Similarity	NPC63031
0.7489	Intermediate Similarity	NPC473186
0.7489	Intermediate Similarity	NPC196718
0.7489	Intermediate Similarity	NPC165743
0.7488	Intermediate Similarity	NPC477003
0.7487	Intermediate Similarity	NPC311276
0.7487	Intermediate Similarity	NPC40779
0.7478	Intermediate Similarity	NPC326363
0.7477	Intermediate Similarity	NPC207866
0.7476	Intermediate Similarity	NPC474916
0.7475	Intermediate Similarity	NPC470498
0.7468	Intermediate Similarity	NPC314882
0.7465	Intermediate Similarity	NPC294375
0.7461	Intermediate Similarity	NPC469762
0.7456	Intermediate Similarity	NPC323752
0.7455	Intermediate Similarity	NPC141428
0.7451	Intermediate Similarity	NPC62510
0.7449	Intermediate Similarity	NPC42372
0.7442	Intermediate Similarity	NPC283117
0.7441	Intermediate Similarity	NPC472296
0.7441	Intermediate Similarity	NPC477045
0.7441	Intermediate Similarity	NPC293917
0.7441	Intermediate Similarity	NPC472297
0.7438	Intermediate Similarity	NPC102755
0.7432	Intermediate Similarity	NPC272174
0.743	Intermediate Similarity	NPC473376
0.743	Intermediate Similarity	NPC132539
0.7429	Intermediate Similarity	NPC156704
0.7429	Intermediate Similarity	NPC74153
0.7424	Intermediate Similarity	NPC325976
0.7419	Intermediate Similarity	NPC303951
0.7417	Intermediate Similarity	NPC478006
0.7415	Intermediate Similarity	NPC94752
0.7413	Intermediate Similarity	NPC59269
0.7412	Intermediate Similarity	NPC102593
0.7411	Intermediate Similarity	NPC54988
0.7409	Intermediate Similarity	NPC469785
0.7403	Intermediate Similarity	NPC101350
0.7402	Intermediate Similarity	NPC228835

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 NPC472285 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	607
0.2-0.3	902
0.3-0.4	1700
0.4-0.5	2777
0.5-0.6	1992
0.6-0.7	856
0.7-0.8	116
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD5901	Discontinued
0.8155	Intermediate Similarity	NPD7001	Phase 3
0.801	Intermediate Similarity	NPD3178	Discontinued
0.799	Intermediate Similarity	NPD2510	Approved
0.799	Intermediate Similarity	NPD2509	Approved
0.7962	Intermediate Similarity	NPD7470	Discontinued
0.7885	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD5426	Phase 3
0.7789	Intermediate Similarity	NPD2092	Phase 2
0.7789	Intermediate Similarity	NPD2094	Phase 2
0.7789	Intermediate Similarity	NPD2095	Phase 2
0.7778	Intermediate Similarity	NPD6999	Discontinued
0.7778	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2096	Phase 2
0.775	Intermediate Similarity	NPD2091	Phase 2
0.7746	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD482	Approved
0.7665	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD484	Approved
0.765	Intermediate Similarity	NPD3394	Approved
0.765	Intermediate Similarity	NPD3393	Approved
0.765	Intermediate Similarity	NPD3389	Approved
0.7626	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD750	Phase 2
0.7512	Intermediate Similarity	NPD6595	Phase 3
0.75	Intermediate Similarity	NPD8289	Discontinued
0.7488	Intermediate Similarity	NPD7665	Phase 2
0.7488	Intermediate Similarity	NPD7666	Phase 3
0.7487	Intermediate Similarity	NPD5065	Approved
0.7477	Intermediate Similarity	NPD3794	Approved
0.7477	Intermediate Similarity	NPD3795	Approved
0.7468	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4948	Discontinued
0.7444	Intermediate Similarity	NPD6995	Phase 1
0.7441	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4852	Phase 2
0.7431	Intermediate Similarity	NPD8093	Discontinued
0.743	Intermediate Similarity	NPD3947	Discontinued
0.7421	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7944	Discontinued
0.7402	Intermediate Similarity	NPD1096	Discontinued
0.7395	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5017	Discontinued
0.7364	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6242	Discontinued
0.7349	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7603	Discontinued
0.7342	Intermediate Similarity	NPD5482	Discontinued
0.7337	Intermediate Similarity	NPD1575	Approved
0.7337	Intermediate Similarity	NPD1573	Approved
0.7321	Intermediate Similarity	NPD6665	Discontinued
0.7317	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6165	Phase 2
0.7313	Intermediate Similarity	NPD4845	Discontinued
0.7313	Intermediate Similarity	NPD6164	Phase 2
0.7297	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7688	Phase 1
0.7286	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD2844	Phase 3
0.7281	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8097	Phase 3
0.7273	Intermediate Similarity	NPD8096	Phase 3
0.7273	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD6987	Phase 1
0.7265	Intermediate Similarity	NPD7878	Phase 2
0.7264	Intermediate Similarity	NPD7948	Phase 1
0.7264	Intermediate Similarity	NPD5003	Discontinued
0.725	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6530	Approved
0.7243	Intermediate Similarity	NPD6531	Approved
0.7241	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8094	Discontinued
0.723	Intermediate Similarity	NPD7946	Pre-registration
0.7227	Intermediate Similarity	NPD5475	Discontinued
0.7204	Intermediate Similarity	NPD802	Phase 2
0.7202	Intermediate Similarity	NPD1392	Approved
0.72	Intermediate Similarity	NPD3280	Approved
0.7198	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8272	Phase 2
0.7189	Intermediate Similarity	NPD8098	Approved
0.7188	Intermediate Similarity	NPD5632	Approved
0.7184	Intermediate Similarity	NPD5596	Phase 2
0.7176	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5612	Discontinued
0.7171	Intermediate Similarity	NPD6452	Discontinued
0.7167	Intermediate Similarity	NPD3006	Discontinued
0.7156	Intermediate Similarity	NPD6770	Approved
0.7156	Intermediate Similarity	NPD2008	Discontinued
0.715	Intermediate Similarity	NPD7777	Approved
0.715	Intermediate Similarity	NPD53	Approved
0.715	Intermediate Similarity	NPD7778	Approved
0.7136	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7970	Approved
0.713	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5479	Discontinued
0.7087	Intermediate Similarity	NPD1643	Phase 3
0.7085	Intermediate Similarity	NPD6456	Discontinued
0.7083	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD7558	Phase 2
0.7081	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2144	Approved
0.7072	Intermediate Similarity	NPD5067	Phase 2
0.7072	Intermediate Similarity	NPD5066	Phase 2
0.7067	Intermediate Similarity	NPD2813	Phase 3
0.7067	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6176	Phase 1
0.7062	Intermediate Similarity	NPD2565	Phase 2
0.7062	Intermediate Similarity	NPD2564	Approved
0.7059	Intermediate Similarity	NPD4506	Discontinued
0.7056	Intermediate Similarity	NPD5450	Discontinued
0.7054	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7817	Phase 1
0.705	Intermediate Similarity	NPD1631	Approved
0.7048	Intermediate Similarity	NPD1996	Discontinued
0.7042	Intermediate Similarity	NPD1038	Approved
0.704	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4076	Approved
0.7039	Intermediate Similarity	NPD4079	Approved
0.7032	Intermediate Similarity	NPD8114	Approved
0.7032	Intermediate Similarity	NPD8115	Approved
0.7032	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5022	Discontinued
0.7022	Intermediate Similarity	NPD8160	Phase 2
0.702	Intermediate Similarity	NPD7181	Phase 3
0.7017	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4558	Phase 2
0.7009	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4601	Approved
0.7005	Intermediate Similarity	NPD4600	Approved
0.7	Intermediate Similarity	NPD7957	Phase 1
0.7	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3003	Approved
0.6995	Remote Similarity	NPD1326	Approved
0.6995	Remote Similarity	NPD1325	Approved
0.6991	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3506	Approved
0.699	Remote Similarity	NPD3505	Approved
0.6987	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD8072	Approved
0.6977	Remote Similarity	NPD4848	Phase 1
0.6977	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7727	Phase 2
0.6972	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3038	Discontinued
0.697	Remote Similarity	NPD7711	Discontinued
0.6968	Remote Similarity	NPD8322	Phase 2
0.6966	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD5138	Approved
0.6965	Remote Similarity	NPD5140	Approved
0.6964	Remote Similarity	NPD3330	Phase 1
0.6964	Remote Similarity	NPD3917	Approved
0.6964	Remote Similarity	NPD2411	Approved
0.6964	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3918	Approved
0.6958	Remote Similarity	NPD7921	Approved
0.6955	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2336	Approved
0.6941	Remote Similarity	NPD8073	Approved
0.694	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7952	Approved
0.6936	Remote Similarity	NPD7953	Approved
0.6936	Remote Similarity	NPD7950	Approved
0.6936	Remote Similarity	NPD7791	Approved
0.6936	Remote Similarity	NPD7789	Approved
0.6936	Remote Similarity	NPD7951	Approved
0.6936	Remote Similarity	NPD7790	Approved
0.6936	Remote Similarity	NPD4373	Phase 2
0.6934	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3243	Approved
0.6932	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4602	Approved
0.693	Remote Similarity	NPD7618	Phase 3
0.693	Remote Similarity	NPD7619	Phase 3
0.6927	Remote Similarity	NPD4501	Approved
0.6927	Remote Similarity	NPD4500	Approved
0.6923	Remote Similarity	NPD5898	Approved
0.6923	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5897	Approved
0.6923	Remote Similarity	NPD5899	Approved
0.692	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.692	Remote Similarity	NPD3915	Approved
0.6916	Remote Similarity	NPD3404	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