NPASS Compound

Structure

CID327477 OpenBabel06191716192D 21 22 0 0 1 0 0 0 0 0999 V2000 4.8564 1.5180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6165 1.2392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1165 2.7781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8074 1.8270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6485 0.5398 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0032 0.5909 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6974 0.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7953 -0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3916 -0.1293 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4255 1.8270 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1165 2.7781 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 2.9543 0.9000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4895 -0.7473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8443 -0.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5385 -1.0563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 9 1 0 0 0 0 2 8 1 0 0 0 0 3 7 2 0 0 0 0 3 14 1 0 0 0 0 4 8 2 0 0 0 0 4 15 1 0 0 0 0 5 14 2 0 0 0 0 5 16 1 0 0 0 0 6 15 2 0 0 0 0 6 17 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 6 0 0 0 10 2 1 6 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 18 2 3 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.13
Volume:	275.528
LogP:	-2.82
LogD:	-2.421
LogS:	-0.913
# Rotatable Bonds:	8
TPSA:	149.78
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	3.619
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.816
MDCK Permeability:	2.852990519386367e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.916
Plasma Protein Binding (PPB):	10.749615669250488%
Volume Distribution (VD):	0.376
Pgp-substrate:	94.7978744506836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.325
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.19
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	2.357
Half-life (T1/2):	0.94

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.147
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.817
Carcinogencity:	0.001
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC327477

Natural Product ID:	NPC327477
*Common Name:**	His-His
IUPAC Name:	(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-(1H-imidazol-5-yl)propanoic acid
Synonyms:	His-His
Standard InCHIKey:	SGCGMORCWLEJNZ-UWVGGRQHSA-N
Standard InCHI:	InChI=1S/C12H16N6O3/c13-9(1-7-3-14-5-16-7)11(19)18-10(12(20)21)2-8-4-15-6-17-8/h3-6,9-10H,1-2,13H2,(H,14,16)(H,15,17)(H,18,19)(H,20,21)/t9-,10-/m0/s1
SMILES:	OC(=O)[C@@H](N=C([C@H](Cc1cnc[nH]1)N)O)Cc1cnc[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL377872
PubChem CID:	6993105 6993104
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004830] Dipeptides

*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
NPO30193	Mycoplasma genitalium	Species	Mycoplasmataceae	Bacteria	n.a.	n.a.	n.a.	PMID[22817898]

☑ 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
EC50	1
IC50	1
Others	3

Activity Type	# Activity
Individual Protein	4
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	EC50	=	370000.0	nM	PMID[459971]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	max activation	=	132.0	%	PMID[459971]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	IC50	=	400000.0	nM	PMID[459971]
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	Ratio	=	350.0	n.a.	PMID[459971]
NPT21154	SINGLE PROTEIN	General amino-acid permease GAP1	Saccharomyces cerevisiae	Inhibition	=	15.0	%	PMID[459972]

☑ 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 NPC327477 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	475
0.1-0.2	30816
0.2-0.3	5766
0.3-0.4	3481
0.4-0.5	1718
0.5-0.6	354
0.6-0.7	54
0.7-0.8	16
0.8-0.85	5
0.85-0.9	7
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9624	High Similarity	NPC286696
0.9478	High Similarity	NPC185903
0.9398	High Similarity	NPC237812
0.9398	High Similarity	NPC18223
0.9023	High Similarity	NPC235501
0.8978	High Similarity	NPC210947
0.8824	High Similarity	NPC126634
0.8767	High Similarity	NPC60537
0.8603	High Similarity	NPC25465
0.8333	Intermediate Similarity	NPC470138
0.8309	Intermediate Similarity	NPC180462
0.8276	Intermediate Similarity	NPC174020
0.8227	Intermediate Similarity	NPC470140
0.8182	Intermediate Similarity	NPC470139
0.7899	Intermediate Similarity	NPC15566
0.7687	Intermediate Similarity	NPC327613
0.7514	Intermediate Similarity	NPC313504
0.72	Intermediate Similarity	NPC470141
0.7183	Intermediate Similarity	NPC470142
0.7143	Intermediate Similarity	NPC111132
0.7037	Intermediate Similarity	NPC155498
0.6618	Remote Similarity	NPC326248
0.6618	Remote Similarity	NPC187191
0.6579	Remote Similarity	NPC243319
0.6522	Remote Similarity	NPC197068
0.6497	Remote Similarity	NPC238945
0.6493	Remote Similarity	NPC9639
0.6467	Remote Similarity	NPC201900
0.6453	Remote Similarity	NPC323244
0.6449	Remote Similarity	NPC273327
0.6386	Remote Similarity	NPC282531
0.6335	Remote Similarity	NPC315642
0.6335	Remote Similarity	NPC74306
0.6329	Remote Similarity	NPC328924
0.6324	Remote Similarity	NPC210123
0.6263	Remote Similarity	NPC282247
0.6258	Remote Similarity	NPC246193
0.6235	Remote Similarity	NPC8590
0.6232	Remote Similarity	NPC69843
0.6168	Remote Similarity	NPC171393
0.6168	Remote Similarity	NPC295452
0.6162	Remote Similarity	NPC54981
0.6162	Remote Similarity	NPC477417
0.6162	Remote Similarity	NPC477419
0.6149	Remote Similarity	NPC472790
0.6141	Remote Similarity	NPC477118
0.6108	Remote Similarity	NPC477120
0.6102	Remote Similarity	NPC290959
0.6099	Remote Similarity	NPC40530
0.6099	Remote Similarity	NPC314281
0.6091	Remote Similarity	NPC476524
0.6077	Remote Similarity	NPC477119
0.602	Remote Similarity	NPC473376
0.601	Remote Similarity	NPC71238
0.6	Remote Similarity	NPC473646
0.5936	Remote Similarity	NPC477420
0.5936	Remote Similarity	NPC477418
0.5932	Remote Similarity	NPC324484
0.5906	Remote Similarity	NPC207633
0.5906	Remote Similarity	NPC313547
0.5899	Remote Similarity	NPC325906
0.5894	Remote Similarity	NPC68938
0.5886	Remote Similarity	NPC124276
0.5877	Remote Similarity	NPC156003
0.5867	Remote Similarity	NPC54537
0.585	Remote Similarity	NPC476525
0.5845	Remote Similarity	NPC293163
0.5802	Remote Similarity	NPC262926
0.5789	Remote Similarity	NPC321708
0.5784	Remote Similarity	NPC54744
0.5771	Remote Similarity	NPC239737
0.5771	Remote Similarity	NPC116555
0.5767	Remote Similarity	NPC320818
0.5767	Remote Similarity	NPC61198
0.5759	Remote Similarity	NPC144223
0.5728	Remote Similarity	NPC177996
0.5728	Remote Similarity	NPC147983
0.5724	Remote Similarity	NPC59314
0.5723	Remote Similarity	NPC321052
0.5686	Remote Similarity	NPC278549
0.5684	Remote Similarity	NPC476527
0.5684	Remote Similarity	NPC62749
0.5679	Remote Similarity	NPC57279
0.5677	Remote Similarity	NPC74619
0.5655	Remote Similarity	NPC229974
0.5654	Remote Similarity	NPC313514
0.5629	Remote Similarity	NPC209525
0.5629	Remote Similarity	NPC161659
0.5629	Remote Similarity	NPC41958
0.5625	Remote Similarity	NPC267811
0.5622	Remote Similarity	NPC149155
0.5622	Remote Similarity	NPC203468
0.5622	Remote Similarity	NPC110500
0.5614	Remote Similarity	NPC42483
0.561	Remote Similarity	NPC320968
0.5608	Remote Similarity	NPC270834
0.5607	Remote Similarity	NPC326694
0.5606	Remote Similarity	NPC293917

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 NPC327477 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1762
0.2-0.3	2921
0.3-0.4	2281
0.4-0.5	1594
0.5-0.6	387
0.6-0.7	26
0.7-0.8	9
0.8-0.85	6
0.85-0.9	2
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9398	High Similarity	NPD9133	Approved
0.9254	High Similarity	NPD9628	Approved
0.9197	High Similarity	NPD1451	Approved
0.8921	High Similarity	NPD9183	Clinical (unspecified phase)
0.8794	High Similarity	NPD9627	Approved
0.8767	High Similarity	NPD2180	Approved
0.8699	High Similarity	NPD1731	Clinical (unspecified phase)
0.8649	High Similarity	NPD2604	Approved
0.8444	Intermediate Similarity	NPD300	Approved
0.8421	Intermediate Similarity	NPD3130	Discontinued
0.8278	Intermediate Similarity	NPD3697	Discontinued
0.8125	Intermediate Similarity	NPD875	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD3108	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5342	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD3105	Discontinued
0.7722	Intermediate Similarity	NPD5768	Phase 2
0.7319	Intermediate Similarity	NPD9132	Discontinued
0.7255	Intermediate Similarity	NPD568	Approved
0.7255	Intermediate Similarity	NPD567	Approved
0.7255	Intermediate Similarity	NPD566	Approved
0.7143	Intermediate Similarity	NPD8862	Approved
0.7143	Intermediate Similarity	NPD8861	Approved
0.7143	Intermediate Similarity	NPD8859	Approved
0.6923	Remote Similarity	NPD3706	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1807	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1388	Phase 1
0.6803	Remote Similarity	NPD1389	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1390	Phase 1
0.6702	Remote Similarity	NPD8261	Discontinued
0.6702	Remote Similarity	NPD7465	Suspended
0.6667	Remote Similarity	NPD3708	Phase 2
0.6596	Remote Similarity	NPD3497	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD576	Discontinued
0.6579	Remote Similarity	NPD9081	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD8641	Approved
0.6471	Remote Similarity	NPD1249	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD8292	Phase 2
0.6335	Remote Similarity	NPD582	Approved
0.631	Remote Similarity	NPD8113	Phase 2
0.6271	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8271	Discontinued
0.6215	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD1808	Phase 1
0.6139	Remote Similarity	NPD209	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD2618	Phase 1
0.6135	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD8629	Discontinued
0.61	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD536	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD2456	Phase 2
0.6087	Remote Similarity	NPD2457	Phase 2
0.6062	Remote Similarity	NPD1121	Approved
0.6062	Remote Similarity	NPD1120	Approved
0.6054	Remote Similarity	NPD7245	Approved
0.6054	Remote Similarity	NPD7246	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7842	Phase 2
0.6026	Remote Similarity	NPD870	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD459	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD1335	Approved
0.5965	Remote Similarity	NPD1029	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD1030	Approved
0.5965	Remote Similarity	NPD1027	Approved
0.596	Remote Similarity	NPD7834	Approved
0.5943	Remote Similarity	NPD8119	Discontinued
0.593	Remote Similarity	NPD7981	Discontinued
0.5922	Remote Similarity	NPD245	Suspended
0.5916	Remote Similarity	NPD460	Discontinued
0.5915	Remote Similarity	NPD1118	Discontinued
0.5899	Remote Similarity	NPD1776	Approved
0.5899	Remote Similarity	NPD1777	Approved
0.5896	Remote Similarity	NPD1303	Phase 1
0.5894	Remote Similarity	NPD4414	Discontinued
0.5879	Remote Similarity	NPD1430	Approved
0.5879	Remote Similarity	NPD1431	Approved
0.5876	Remote Similarity	NPD1122	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD757	Phase 3
0.5867	Remote Similarity	NPD4458	Phase 2
0.5867	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD3405	Phase 3
0.5858	Remote Similarity	NPD775	Approved
0.5855	Remote Similarity	NPD9360	Approved
0.5829	Remote Similarity	NPD2008	Discontinued
0.5829	Remote Similarity	NPD276	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD1600	Suspended
0.5821	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD3593	Approved
0.5805	Remote Similarity	NPD695	Discontinued
0.5802	Remote Similarity	NPD194	Clinical (unspecified phase)
0.58	Remote Similarity	NPD796	Phase 2
0.578	Remote Similarity	NPD1369	Phase 2
0.578	Remote Similarity	NPD1750	Clinical (unspecified phase)
0.5777	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.5777	Remote Similarity	NPD8257	Approved
0.5777	Remote Similarity	NPD8256	Approved
0.5776	Remote Similarity	NPD547	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD2138	Approved
0.5775	Remote Similarity	NPD2137	Approved
0.5771	Remote Similarity	NPD2624	Phase 2
0.5767	Remote Similarity	NPD252	Clinical (unspecified phase)
0.5759	Remote Similarity	NPD515	Phase 1
0.5756	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.5756	Remote Similarity	NPD7970	Approved
0.575	Remote Similarity	NPD9632	Phase 3
0.5744	Remote Similarity	NPD2880	Discontinued
0.5739	Remote Similarity	NPD1290	Phase 2
0.5737	Remote Similarity	NPD6418	Phase 1
0.5732	Remote Similarity	NPD579	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD3353	Approved
0.5724	Remote Similarity	NPD8837	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD341	Approved
0.5724	Remote Similarity	NPD340	Approved
0.5723	Remote Similarity	NPD1355	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD1354	Approved
0.5723	Remote Similarity	NPD1356	Approved
0.5721	Remote Similarity	NPD8105	Discontinued
0.5721	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD8075	Discontinued
0.5707	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.5705	Remote Similarity	NPD8955	Approved
0.5705	Remote Similarity	NPD8954	Approved
0.57	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.5693	Remote Similarity	NPD2443	Approved
0.5693	Remote Similarity	NPD2442	Approved
0.5691	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD1368	Approved
0.5684	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD1732	Phase 3
0.5682	Remote Similarity	NPD2646	Discontinued
0.5679	Remote Similarity	NPD545	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD1042	Clinical (unspecified phase)
0.5661	Remote Similarity	NPD2091	Phase 2
0.5661	Remote Similarity	NPD2096	Phase 2
0.5659	Remote Similarity	NPD2411	Approved
0.5655	Remote Similarity	NPD2179	Discontinued
0.5654	Remote Similarity	NPD7138	Phase 2
0.5652	Remote Similarity	NPD248	Discontinued
0.5649	Remote Similarity	NPD237	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD3410	Approved
0.5644	Remote Similarity	NPD3411	Phase 2
0.5644	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD2134	Approved
0.5635	Remote Similarity	NPD2135	Approved
0.5635	Remote Similarity	NPD2136	Approved
0.5629	Remote Similarity	NPD549	Approved
0.5629	Remote Similarity	NPD193	Suspended
0.5622	Remote Similarity	NPD482	Approved
0.5619	Remote Similarity	NPD996	Phase 2
0.5619	Remote Similarity	NPD6210	Phase 3
0.5619	Remote Similarity	NPD2127	Suspended
0.5619	Remote Similarity	NPD994	Phase 2
0.5617	Remote Similarity	NPD9650	Phase 3
0.5614	Remote Similarity	NPD9724	Phase 1
0.5614	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.5613	Remote Similarity	NPD307	Approved
0.561	Remote Similarity	NPD1119	Phase 2
0.561	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5608	Remote Similarity	NPD2094	Phase 2
0.5608	Remote Similarity	NPD2092	Phase 2
0.5608	Remote Similarity	NPD2095	Phase 2
0.5607	Remote Similarity	NPD6164	Phase 2
0.5607	Remote Similarity	NPD6165	Phase 2
0.5606	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5602	Remote Similarity	NPD2793	Discontinued

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