NPASS Compound

Structure

NPC177056 OpenBabel07101719242D 33 35 0 0 1 0 0 0 0 0999 V2000 -2.9941 -2.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3125 -2.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -0.8736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4553 2.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8601 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7916 2.0350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2635 -2.7788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9941 -1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1045 -1.4917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3849 1.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8601 -0.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0067 -2.1097 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9941 0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 -0.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8477 -0.8225 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 5.9577 -2.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 -0.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7261 -1.0477 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.1535 -1.1826 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7987 -1.1315 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 -2.7861 1.9305 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4714 -3.7570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2620 -1.0477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6398 0.1556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1656 -3.3969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7009 -1.7496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 0.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 4 26 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 21 1 0 0 0 0 8 33 1 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 10 2 1 1 0 0 0 10 17 1 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 13 7 1 6 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 16 28 1 0 0 0 0 17 24 2 3 0 0 0 17 29 1 0 0 0 0 18 25 2 0 0 0 0 18 33 1 0 0 0 0 19 30 2 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 3 0 0 0 20 32 1 0 0 0 0 21 3 1 1 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.14
Volume:	445.741
LogP:	0.254
LogD:	0.662
LogS:	-1.822
# Rotatable Bonds:	9
TPSA:	162.48
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	4.592
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.612
MDCK Permeability:	3.6638055007642834e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.67
20% Bioavailability (F20%):	0.091
30% Bioavailability (F30%):	0.121

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279
Plasma Protein Binding (PPB):	75.38162994384766%
Volume Distribution (VD):	1.999
Pgp-substrate:	25.05379867553711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.239
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.193
CYP2C9-inhibitor:	0.075
CYP2C9-substrate:	0.303
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.281
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	2.083
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.301
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.08
Skin Sensitization:	0.099
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.496

Download Data

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

Natural Product: NPC177056

Natural Product ID:	NPC177056
*Common Name:**	(S)-2-((R)-2-((R)-2-(6-Chloro-4-Hydroxy-1,5-Dimethyl-1H-Indol-3-Yl)-4-Methyl-4,5-Dihydrooxazole-4-Carboxamido)Propanamido)-3-Hydroxypropanoic Acid
IUPAC Name:	(2S)-2-[[(2R)-2-[[(4R)-2-(6-chloro-4-hydroxy-1,5-dimethylindol-3-yl)-4-methyl-5H-1,3-oxazole-4-carbonyl]amino]propanoyl]amino]-3-hydroxypropanoic acid
Synonyms:
Standard InCHIKey:	OTAMFIXIIUUMKV-JGMWFTNYSA-N
Standard InCHI:	InChI=1S/C21H25ClN4O7/c1-9-12(22)5-14-15(16(9)28)11(6-26(14)4)18-25-21(3,8-33-18)20(32)23-10(2)17(29)24-13(7-27)19(30)31/h5-6,10,13,27-28H,7-8H2,1-4H3,(H,23,32)(H,24,29)(H,30,31)/t10-,13+,21-/m1/s1
SMILES:	Cc1c(cc2c(c(cn2C)C2=N[C@](C)(CO2)C(=N[C@H](C)C(=N[C@@H](CO)C(=O)O)O)O)c1O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1082187
PubChem CID:	46182908
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:0004831] Oligopeptides

*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
NPO32835	Streptomyces sp. Sp080513GE-23	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20146504]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	1000000.0	nM	PMID[507374]

☑ 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 NPC177056 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	408
0.1-0.2	3180
0.2-0.3	13882
0.3-0.4	14835
0.4-0.5	6523
0.5-0.6	2799
0.6-0.7	1066
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9573	High Similarity	NPC300114
0.7149	Intermediate Similarity	NPC220852
0.7061	Intermediate Similarity	NPC285343
0.7	Intermediate Similarity	NPC125597
0.6971	Remote Similarity	NPC319232
0.6971	Remote Similarity	NPC24370
0.6953	Remote Similarity	NPC11464
0.6947	Remote Similarity	NPC156704
0.6939	Remote Similarity	NPC323198
0.6923	Remote Similarity	NPC28945
0.691	Remote Similarity	NPC469589
0.6892	Remote Similarity	NPC46580
0.6875	Remote Similarity	NPC473317
0.687	Remote Similarity	NPC323752
0.6856	Remote Similarity	NPC315491
0.6856	Remote Similarity	NPC45459
0.684	Remote Similarity	NPC200836
0.684	Remote Similarity	NPC475774
0.6833	Remote Similarity	NPC128115
0.6814	Remote Similarity	NPC106937
0.6807	Remote Similarity	NPC3207
0.6807	Remote Similarity	NPC170114
0.6803	Remote Similarity	NPC110151
0.6803	Remote Similarity	NPC473185
0.6802	Remote Similarity	NPC62510
0.6798	Remote Similarity	NPC243834
0.6798	Remote Similarity	NPC70956
0.6781	Remote Similarity	NPC476106
0.6766	Remote Similarity	NPC174672
0.6765	Remote Similarity	NPC470549
0.6754	Remote Similarity	NPC13880
0.6754	Remote Similarity	NPC242209
0.6754	Remote Similarity	NPC251090
0.6752	Remote Similarity	NPC88008
0.6751	Remote Similarity	NPC316981
0.6736	Remote Similarity	NPC60621
0.6736	Remote Similarity	NPC310118
0.6736	Remote Similarity	NPC2395
0.6724	Remote Similarity	NPC193761
0.6724	Remote Similarity	NPC476874
0.6723	Remote Similarity	NPC470931
0.6722	Remote Similarity	NPC313804
0.6722	Remote Similarity	NPC315804
0.6721	Remote Similarity	NPC235885
0.672	Remote Similarity	NPC15801
0.6709	Remote Similarity	NPC472111
0.6696	Remote Similarity	NPC171171
0.6696	Remote Similarity	NPC306376
0.6695	Remote Similarity	NPC53144
0.6694	Remote Similarity	NPC132642
0.6694	Remote Similarity	NPC174760
0.6693	Remote Similarity	NPC474183
0.6682	Remote Similarity	NPC320394
0.6682	Remote Similarity	NPC190007
0.6681	Remote Similarity	NPC472098
0.668	Remote Similarity	NPC314270
0.6667	Remote Similarity	NPC152768
0.6667	Remote Similarity	NPC307963
0.6667	Remote Similarity	NPC469734
0.6667	Remote Similarity	NPC330009
0.6667	Remote Similarity	NPC148183
0.6653	Remote Similarity	NPC469592
0.6653	Remote Similarity	NPC471080
0.6653	Remote Similarity	NPC475910
0.6653	Remote Similarity	NPC39679
0.6652	Remote Similarity	NPC475085
0.6652	Remote Similarity	NPC291535
0.6652	Remote Similarity	NPC475112
0.6652	Remote Similarity	NPC314002
0.6652	Remote Similarity	NPC94943
0.6641	Remote Similarity	NPC314882
0.664	Remote Similarity	NPC99891
0.664	Remote Similarity	NPC316411
0.6638	Remote Similarity	NPC475841
0.6638	Remote Similarity	NPC474145
0.6638	Remote Similarity	NPC213308
0.6626	Remote Similarity	NPC150239
0.6626	Remote Similarity	NPC477533
0.6624	Remote Similarity	NPC174758
0.6614	Remote Similarity	NPC473187
0.6612	Remote Similarity	NPC264285
0.6612	Remote Similarity	NPC469594
0.6611	Remote Similarity	NPC112206
0.6611	Remote Similarity	NPC202605
0.661	Remote Similarity	NPC193777
0.6607	Remote Similarity	NPC204717
0.6606	Remote Similarity	NPC211997
0.6599	Remote Similarity	NPC244536
0.6598	Remote Similarity	NPC477532
0.6597	Remote Similarity	NPC303951
0.6596	Remote Similarity	NPC329708
0.6596	Remote Similarity	NPC118832
0.6596	Remote Similarity	NPC47059
0.6596	Remote Similarity	NPC165349
0.6596	Remote Similarity	NPC274291
0.6596	Remote Similarity	NPC264166
0.6587	Remote Similarity	NPC473183
0.6586	Remote Similarity	NPC267853
0.6586	Remote Similarity	NPC14288
0.6586	Remote Similarity	NPC315062
0.6584	Remote Similarity	NPC74360
0.6584	Remote Similarity	NPC193267
0.6584	Remote Similarity	NPC213530
0.6583	Remote Similarity	NPC229348
0.6583	Remote Similarity	NPC74562
0.6583	Remote Similarity	NPC151781
0.6583	Remote Similarity	NPC317752
0.6583	Remote Similarity	NPC316181
0.6583	Remote Similarity	NPC478074
0.6581	Remote Similarity	NPC295898
0.658	Remote Similarity	NPC77555
0.658	Remote Similarity	NPC224928
0.6579	Remote Similarity	NPC92111
0.6574	Remote Similarity	NPC263937
0.6574	Remote Similarity	NPC94428
0.6574	Remote Similarity	NPC473184
0.657	Remote Similarity	NPC169402
0.6569	Remote Similarity	NPC23294
0.6568	Remote Similarity	NPC472287
0.6568	Remote Similarity	NPC472286
0.6562	Remote Similarity	NPC220765
0.6562	Remote Similarity	NPC212535
0.6562	Remote Similarity	NPC78609
0.6561	Remote Similarity	NPC134586
0.6561	Remote Similarity	NPC470784
0.656	Remote Similarity	NPC244897
0.6559	Remote Similarity	NPC214980
0.6552	Remote Similarity	NPC472435
0.6552	Remote Similarity	NPC102008
0.655	Remote Similarity	NPC99666
0.6546	Remote Similarity	NPC322135
0.6546	Remote Similarity	NPC326363
0.6546	Remote Similarity	NPC95240
0.6543	Remote Similarity	NPC303658
0.6543	Remote Similarity	NPC247803
0.6542	Remote Similarity	NPC264176
0.6542	Remote Similarity	NPC318299
0.654	Remote Similarity	NPC53344
0.654	Remote Similarity	NPC472436
0.654	Remote Similarity	NPC478006
0.654	Remote Similarity	NPC316403
0.6535	Remote Similarity	NPC477861
0.6535	Remote Similarity	NPC76748
0.6534	Remote Similarity	NPC473105
0.6532	Remote Similarity	NPC186351
0.6532	Remote Similarity	NPC96890
0.6529	Remote Similarity	NPC469928
0.6529	Remote Similarity	NPC74969
0.6527	Remote Similarity	NPC85273
0.6527	Remote Similarity	NPC5145
0.6525	Remote Similarity	NPC285558
0.6522	Remote Similarity	NPC184680
0.6522	Remote Similarity	NPC104712
0.6518	Remote Similarity	NPC71037
0.6516	Remote Similarity	NPC469938
0.6516	Remote Similarity	NPC473179
0.6515	Remote Similarity	NPC266931
0.6511	Remote Similarity	NPC155143
0.6511	Remote Similarity	NPC211813
0.6511	Remote Similarity	NPC470678
0.6509	Remote Similarity	NPC153042
0.6506	Remote Similarity	NPC100547
0.6504	Remote Similarity	NPC16352
0.65	Remote Similarity	NPC87413
0.6498	Remote Similarity	NPC284141
0.6496	Remote Similarity	NPC11017
0.6496	Remote Similarity	NPC470785
0.6496	Remote Similarity	NPC121772
0.6496	Remote Similarity	NPC470497
0.6494	Remote Similarity	NPC54803
0.6494	Remote Similarity	NPC321592
0.6493	Remote Similarity	NPC478010
0.6491	Remote Similarity	NPC296527
0.6489	Remote Similarity	NPC469358
0.6488	Remote Similarity	NPC478157
0.6488	Remote Similarity	NPC116238
0.6485	Remote Similarity	NPC478158
0.6481	Remote Similarity	NPC149708
0.6481	Remote Similarity	NPC72211
0.6481	Remote Similarity	NPC473640
0.648	Remote Similarity	NPC223409
0.6476	Remote Similarity	NPC235684
0.6475	Remote Similarity	NPC189079
0.6475	Remote Similarity	NPC473041
0.6473	Remote Similarity	NPC202768
0.6473	Remote Similarity	NPC87856
0.6473	Remote Similarity	NPC296482
0.6473	Remote Similarity	NPC48353
0.6473	Remote Similarity	NPC151976
0.6473	Remote Similarity	NPC53069
0.6471	Remote Similarity	NPC183777
0.6468	Remote Similarity	NPC475506
0.6468	Remote Similarity	NPC232727
0.6466	Remote Similarity	NPC124920
0.6466	Remote Similarity	NPC34580
0.6466	Remote Similarity	NPC304307
0.6466	Remote Similarity	NPC118559
0.6466	Remote Similarity	NPC192712
0.6466	Remote Similarity	NPC261251
0.6462	Remote Similarity	NPC477630

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 NPC177056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	679
0.2-0.3	998
0.3-0.4	1823
0.4-0.5	3139
0.5-0.6	1819
0.6-0.7	478
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7378	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD1229	Phase 2
0.7294	Intermediate Similarity	NPD7673	Phase 3
0.7254	Intermediate Similarity	NPD7576	Discontinued
0.7227	Intermediate Similarity	NPD3259	Approved
0.7166	Intermediate Similarity	NPD4349	Approved
0.7166	Intermediate Similarity	NPD4350	Approved
0.7117	Intermediate Similarity	NPD4528	Approved
0.7117	Intermediate Similarity	NPD4529	Approved
0.7117	Intermediate Similarity	NPD4526	Approved
0.7082	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7218	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1392	Approved
0.6969	Remote Similarity	NPD8463	Approved
0.6951	Remote Similarity	NPD4454	Phase 2
0.6943	Remote Similarity	NPD3928	Approved
0.6943	Remote Similarity	NPD3931	Approved
0.6923	Remote Similarity	NPD5450	Discontinued
0.6917	Remote Similarity	NPD7219	Approved
0.6917	Remote Similarity	NPD7221	Approved
0.6906	Remote Similarity	NPD1213	Phase 3
0.6868	Remote Similarity	NPD7691	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD3258	Approved
0.6856	Remote Similarity	NPD484	Approved
0.6853	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7069	Discontinued
0.6814	Remote Similarity	NPD802	Phase 2
0.6813	Remote Similarity	NPD4875	Phase 3
0.6813	Remote Similarity	NPD4876	Phase 3
0.6807	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7558	Phase 2
0.6793	Remote Similarity	NPD2615	Phase 3
0.6793	Remote Similarity	NPD2616	Phase 3
0.6784	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7001	Phase 3
0.678	Remote Similarity	NPD7470	Discontinued
0.6774	Remote Similarity	NPD2077	Approved
0.6774	Remote Similarity	NPD2076	Approved
0.6773	Remote Similarity	NPD6790	Phase 1
0.6769	Remote Similarity	NPD2727	Phase 2
0.6763	Remote Similarity	NPD3280	Approved
0.6758	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD3330	Phase 1
0.6736	Remote Similarity	NPD5612	Discontinued
0.6735	Remote Similarity	NPD4328	Approved
0.6733	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4418	Discontinued
0.6709	Remote Similarity	NPD3003	Approved
0.6707	Remote Similarity	NPD7555	Discontinued
0.6706	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3257	Approved
0.6693	Remote Similarity	NPD6154	Approved
0.6681	Remote Similarity	NPD7222	Phase 2
0.6681	Remote Similarity	NPD7452	Approved
0.6681	Remote Similarity	NPD7453	Approved
0.668	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1768	Approved
0.6667	Remote Similarity	NPD1038	Approved
0.6667	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6494	Phase 2
0.6654	Remote Similarity	NPD5482	Discontinued
0.6652	Remote Similarity	NPD7948	Phase 1
0.6652	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6736	Discontinued
0.6638	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7169	Suspended
0.6625	Remote Similarity	NPD4897	Phase 2
0.6623	Remote Similarity	NPD9689	Approved
0.6615	Remote Similarity	NPD8102	Discontinued
0.6614	Remote Similarity	NPD6735	Approved
0.6612	Remote Similarity	NPD3354	Phase 2
0.6608	Remote Similarity	NPD2565	Phase 2
0.6608	Remote Similarity	NPD2564	Approved
0.6606	Remote Similarity	NPD2144	Approved
0.6602	Remote Similarity	NPD7659	Discontinued
0.66	Remote Similarity	NPD4373	Phase 2
0.6599	Remote Similarity	NPD4086	Phase 1
0.6598	Remote Similarity	NPD5506	Approved
0.6598	Remote Similarity	NPD5507	Approved
0.6596	Remote Similarity	NPD4037	Approved
0.6596	Remote Similarity	NPD4036	Approved
0.6596	Remote Similarity	NPD32	Approved
0.6596	Remote Similarity	NPD4122	Approved
0.6596	Remote Similarity	NPD4035	Approved
0.6596	Remote Similarity	NPD31	Approved
0.6596	Remote Similarity	NPD4039	Approved
0.6596	Remote Similarity	NPD4033	Approved
0.6596	Remote Similarity	NPD4038	Approved
0.6596	Remote Similarity	NPD4034	Approved
0.6595	Remote Similarity	NPD9688	Approved
0.6595	Remote Similarity	NPD9687	Approved
0.6588	Remote Similarity	NPD7413	Phase 3
0.6583	Remote Similarity	NPD3243	Approved
0.6582	Remote Similarity	NPD2916	Discontinued
0.6582	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6975	Discontinued
0.6579	Remote Similarity	NPD4699	Discontinued
0.6569	Remote Similarity	NPD5066	Phase 2
0.6569	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5067	Phase 2
0.6568	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7426	Phase 1
0.6556	Remote Similarity	NPD5902	Approved
0.6556	Remote Similarity	NPD6709	Phase 3
0.6556	Remote Similarity	NPD5903	Approved
0.6552	Remote Similarity	NPD7778	Approved
0.6552	Remote Similarity	NPD7777	Approved
0.6552	Remote Similarity	NPD53	Approved
0.6546	Remote Similarity	NPD4952	Phase 3
0.6546	Remote Similarity	NPD8512	Phase 3
0.6546	Remote Similarity	NPD7567	Approved
0.6545	Remote Similarity	NPD750	Phase 2
0.6543	Remote Similarity	NPD5632	Approved
0.6543	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD5488	Discontinued
0.6535	Remote Similarity	NPD6281	Approved
0.6535	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8430	Approved
0.6522	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.652	Remote Similarity	NPD2383	Phase 1
0.6518	Remote Similarity	NPD3038	Discontinued
0.6518	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4203	Approved
0.6518	Remote Similarity	NPD4204	Approved
0.6513	Remote Similarity	NPD7963	Phase 3
0.651	Remote Similarity	NPD7417	Discontinued
0.6509	Remote Similarity	NPD5003	Discontinued
0.6502	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7944	Discontinued
0.6494	Remote Similarity	NPD4427	Phase 2
0.649	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD5891	Approved
0.6481	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6569	Phase 2
0.6478	Remote Similarity	NPD3601	Discontinued
0.6475	Remote Similarity	NPD6985	Discontinued
0.6473	Remote Similarity	NPD6452	Discontinued
0.6473	Remote Similarity	NPD3816	Phase 1
0.6473	Remote Similarity	NPD3815	Phase 1
0.6468	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD8363	Approved
0.6468	Remote Similarity	NPD8364	Approved
0.6464	Remote Similarity	NPD8244	Phase 2
0.6462	Remote Similarity	NPD8101	Phase 3
0.6461	Remote Similarity	NPD7112	Discontinued
0.6461	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4343	Phase 1
0.6457	Remote Similarity	NPD4344	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5901	Discontinued
0.6456	Remote Similarity	NPD4795	Phase 2
0.6453	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.645	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6455	Phase 3
0.6448	Remote Similarity	NPD7214	Phase 3
0.6447	Remote Similarity	NPD8429	Approved
0.6447	Remote Similarity	NPD3119	Phase 1
0.6447	Remote Similarity	NPD8427	Approved
0.6447	Remote Similarity	NPD8466	Approved
0.6447	Remote Similarity	NPD8428	Approved
0.6447	Remote Similarity	NPD8465	Approved
0.6447	Remote Similarity	NPD8467	Approved
0.6447	Remote Similarity	NPD3120	Approved
0.6446	Remote Similarity	NPD5944	Phase 1
0.6446	Remote Similarity	NPD5945	Phase 1
0.6444	Remote Similarity	NPD2509	Approved
0.6444	Remote Similarity	NPD2510	Approved
0.6444	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.644	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1856	Discontinued
0.6437	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD8356	Approved
0.6434	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8326	Phase 3
0.6434	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8325	Phase 3
0.6429	Remote Similarity	NPD5530	Phase 1
0.6429	Remote Similarity	NPD7957	Phase 1
0.6429	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD7603	Discontinued
0.6426	Remote Similarity	NPD7674	Phase 3
0.6426	Remote Similarity	NPD7675	Phase 3
0.6426	Remote Similarity	NPD2305	Discontinued
0.6426	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4771	Phase 2
0.6421	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD2094	Phase 2
0.6416	Remote Similarity	NPD2092	Phase 2
0.6416	Remote Similarity	NPD2095	Phase 2
0.6414	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7589	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