NPASS Compound

Structure

NPC300114 OpenBabel07101718182D 32 34 0 0 1 0 0 0 0 0999 V2000 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 -2.9941 -1.0477 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 3.1045 -1.4917 0.0000 C 0 0 2 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 -1.3849 1.1215 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 -0.5477 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 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 3 25 1 0 0 0 0 4 10 2 0 0 0 0 4 13 1 0 0 0 0 5 10 1 0 0 0 0 5 14 2 0 0 0 0 6 11 2 0 0 0 0 6 25 1 0 0 0 0 7 26 1 0 0 0 0 8 20 1 0 0 0 0 8 32 1 0 0 0 0 9 1 1 1 0 0 0 9 16 1 0 0 0 0 9 22 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 7 1 6 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 15 2 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 16 23 2 3 0 0 0 16 28 1 0 0 0 0 17 24 2 0 0 0 0 17 32 1 0 0 0 0 18 29 2 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 3 0 0 0 19 31 1 0 0 0 0 20 2 1 1 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.13
Volume:	428.445
LogP:	0.042
LogD:	0.306
LogS:	-1.788
# 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:	0.273
Synthetic Accessibility Score:	4.481
Fsp3:	0.4
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:	-5.732
MDCK Permeability:	5.360733212000923e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.653
20% Bioavailability (F20%):	0.418
30% Bioavailability (F30%):	0.164

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.391
Plasma Protein Binding (PPB):	72.93000030517578%
Volume Distribution (VD):	1.84
Pgp-substrate:	37.150150299072266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.295
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.143
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.225
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	2.006
Half-life (T1/2):	0.81

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.393
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.091
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.418

Download Data

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

Natural Product: NPC300114

Natural Product ID:	NPC300114
*Common Name:**	(S)-2-((R)-2-((R)-2-(6-Chloro-4-Hydroxy-1-Methyl-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-methylindol-3-yl)-4-methyl-5H-1,3-oxazole-4-carbonyl]amino]propanoyl]amino]-3-hydroxypropanoic acid
Synonyms:
Standard InCHIKey:	NKNDHRJPCHKCQG-GNGCRJPWSA-N
Standard InCHI:	InChI=1S/C20H23ClN4O7/c1-9(16(28)23-12(7-26)18(29)30)22-19(31)20(2)8-32-17(24-20)11-6-25(3)13-4-10(21)5-14(27)15(11)13/h4-6,9,12,26-27H,7-8H2,1-3H3,(H,22,31)(H,23,28)(H,29,30)/t9-,12+,20-/m1/s1
SMILES:	OC[C@@H](C(=O)O)N=C([C@H](N=C([C@@]1(C)COC(=N1)c1cn(c2c1c(O)cc(c2)Cl)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080328
PubChem CID:	46182909
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	=	2500000.0	nM	PMID[506428]

☑ 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 NPC300114 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	400
0.1-0.2	3193
0.2-0.3	13608
0.3-0.4	13042
0.4-0.5	8056
0.5-0.6	3060
0.6-0.7	1318
0.7-0.8	18
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	NPC177056
0.7373	Intermediate Similarity	NPC220852
0.728	Intermediate Similarity	NPC285343
0.7222	Intermediate Similarity	NPC125597
0.7191	Intermediate Similarity	NPC24370
0.7191	Intermediate Similarity	NPC319232
0.7182	Intermediate Similarity	NPC156704
0.7155	Intermediate Similarity	NPC323198
0.7143	Intermediate Similarity	NPC200836
0.7137	Intermediate Similarity	NPC28945
0.7137	Intermediate Similarity	NPC469589
0.713	Intermediate Similarity	NPC46580
0.7124	Intermediate Similarity	NPC128115
0.7123	Intermediate Similarity	NPC106937
0.7094	Intermediate Similarity	NPC473317
0.7085	Intermediate Similarity	NPC315491
0.7085	Intermediate Similarity	NPC45459
0.7083	Intermediate Similarity	NPC323752
0.7067	Intermediate Similarity	NPC475774
0.7061	Intermediate Similarity	NPC174672
0.7059	Intermediate Similarity	NPC242209
0.7059	Intermediate Similarity	NPC13880
0.7031	Intermediate Similarity	NPC11464
0.7017	Intermediate Similarity	NPC110151
0.7009	Intermediate Similarity	NPC315804
0.7009	Intermediate Similarity	NPC313804
0.6982	Remote Similarity	NPC251090
0.6974	Remote Similarity	NPC88008
0.697	Remote Similarity	NPC316981
0.6966	Remote Similarity	NPC314270
0.6959	Remote Similarity	NPC62510
0.6953	Remote Similarity	NPC148183
0.6953	Remote Similarity	NPC152768
0.6949	Remote Similarity	NPC310118
0.6949	Remote Similarity	NPC60621
0.693	Remote Similarity	NPC472111
0.6927	Remote Similarity	NPC171171
0.6926	Remote Similarity	NPC15801
0.692	Remote Similarity	NPC306376
0.6916	Remote Similarity	NPC53144
0.6912	Remote Similarity	NPC320394
0.6898	Remote Similarity	NPC474183
0.6897	Remote Similarity	NPC472098
0.6892	Remote Similarity	NPC307963
0.6881	Remote Similarity	NPC314002
0.688	Remote Similarity	NPC170114
0.6878	Remote Similarity	NPC2395
0.6875	Remote Similarity	NPC244536
0.6872	Remote Similarity	NPC193761
0.6872	Remote Similarity	NPC476874
0.6867	Remote Similarity	NPC471080
0.6867	Remote Similarity	NPC469592
0.6858	Remote Similarity	NPC213308
0.6856	Remote Similarity	NPC472286
0.6856	Remote Similarity	NPC475841
0.6856	Remote Similarity	NPC472287
0.6856	Remote Similarity	NPC474145
0.6842	Remote Similarity	NPC99891
0.684	Remote Similarity	NPC174758
0.6838	Remote Similarity	NPC470549
0.6838	Remote Similarity	NPC314882
0.6837	Remote Similarity	NPC96890
0.6835	Remote Similarity	NPC204717
0.6826	Remote Similarity	NPC316403
0.6824	Remote Similarity	NPC202605
0.6824	Remote Similarity	NPC112206
0.6822	Remote Similarity	NPC264285
0.6822	Remote Similarity	NPC469594
0.6812	Remote Similarity	NPC264166
0.6812	Remote Similarity	NPC274291
0.6812	Remote Similarity	NPC165349
0.6812	Remote Similarity	NPC329708
0.6812	Remote Similarity	NPC47059
0.6812	Remote Similarity	NPC118832
0.6811	Remote Similarity	NPC472435
0.6802	Remote Similarity	NPC92111
0.68	Remote Similarity	NPC77555
0.6798	Remote Similarity	NPC295898
0.6797	Remote Similarity	NPC472436
0.6795	Remote Similarity	NPC151781
0.6795	Remote Similarity	NPC74562
0.6795	Remote Similarity	NPC316181
0.6793	Remote Similarity	NPC213530
0.6793	Remote Similarity	NPC193267
0.6793	Remote Similarity	NPC74360
0.6792	Remote Similarity	NPC235885
0.679	Remote Similarity	NPC14288
0.6789	Remote Similarity	NPC220765
0.6784	Remote Similarity	NPC121772
0.6776	Remote Similarity	NPC316411
0.6771	Remote Similarity	NPC99666
0.6763	Remote Similarity	NPC214980
0.6761	Remote Similarity	NPC470784
0.676	Remote Similarity	NPC78609
0.6759	Remote Similarity	NPC211997
0.6757	Remote Similarity	NPC76748
0.6753	Remote Similarity	NPC53344
0.6752	Remote Similarity	NPC264176
0.6751	Remote Similarity	NPC303658
0.6749	Remote Similarity	NPC95240
0.6749	Remote Similarity	NPC326363
0.6749	Remote Similarity	NPC322135
0.6744	Remote Similarity	NPC469938
0.6743	Remote Similarity	NPC71037
0.6739	Remote Similarity	NPC285558
0.6738	Remote Similarity	NPC5145
0.6738	Remote Similarity	NPC85273
0.6737	Remote Similarity	NPC74969
0.6737	Remote Similarity	NPC3207
0.6737	Remote Similarity	NPC330009
0.6736	Remote Similarity	NPC473185
0.6732	Remote Similarity	NPC478006
0.6726	Remote Similarity	NPC267928
0.6726	Remote Similarity	NPC243834
0.6726	Remote Similarity	NPC70956
0.6725	Remote Similarity	NPC211813
0.6725	Remote Similarity	NPC470678
0.6724	Remote Similarity	NPC287208
0.6724	Remote Similarity	NPC475910
0.6723	Remote Similarity	NPC229348
0.6723	Remote Similarity	NPC266931
0.6721	Remote Similarity	NPC267853
0.6721	Remote Similarity	NPC184680
0.6721	Remote Similarity	NPC315062
0.6713	Remote Similarity	NPC134586
0.6712	Remote Similarity	NPC296527
0.6712	Remote Similarity	NPC469358
0.6708	Remote Similarity	NPC16352
0.6708	Remote Similarity	NPC100547
0.6698	Remote Similarity	NPC471178
0.6698	Remote Similarity	NPC474409
0.6697	Remote Similarity	NPC194040
0.6696	Remote Similarity	NPC102008
0.6694	Remote Similarity	NPC470785
0.6694	Remote Similarity	NPC54803
0.6694	Remote Similarity	NPC244897
0.6694	Remote Similarity	NPC321592
0.6693	Remote Similarity	NPC472434
0.6682	Remote Similarity	NPC62069
0.6682	Remote Similarity	NPC283152
0.6681	Remote Similarity	NPC232727
0.6681	Remote Similarity	NPC202768
0.6681	Remote Similarity	NPC296482
0.6681	Remote Similarity	NPC183777
0.6681	Remote Similarity	NPC53069
0.668	Remote Similarity	NPC223409
0.6679	Remote Similarity	NPC478010
0.6667	Remote Similarity	NPC274982
0.6667	Remote Similarity	NPC124920
0.6667	Remote Similarity	NPC476581
0.6667	Remote Similarity	NPC475070
0.6667	Remote Similarity	NPC36229
0.6667	Remote Similarity	NPC16452
0.6667	Remote Similarity	NPC34580
0.6667	Remote Similarity	NPC118559
0.6667	Remote Similarity	NPC304307
0.6667	Remote Similarity	NPC261251
0.6667	Remote Similarity	NPC288349
0.6667	Remote Similarity	NPC186351
0.6654	Remote Similarity	NPC477630
0.6654	Remote Similarity	NPC477635
0.6653	Remote Similarity	NPC478074
0.6653	Remote Similarity	NPC104712
0.6653	Remote Similarity	NPC260434
0.6652	Remote Similarity	NPC82548
0.6652	Remote Similarity	NPC470931
0.6652	Remote Similarity	NPC155143
0.6652	Remote Similarity	NPC224928
0.6652	Remote Similarity	NPC295158
0.6651	Remote Similarity	NPC263439
0.6651	Remote Similarity	NPC72980
0.6641	Remote Similarity	NPC315467
0.664	Remote Similarity	NPC325976
0.664	Remote Similarity	NPC182222
0.6639	Remote Similarity	NPC314954
0.6639	Remote Similarity	NPC472285
0.6638	Remote Similarity	NPC476106
0.6638	Remote Similarity	NPC470497
0.6638	Remote Similarity	NPC249040
0.6637	Remote Similarity	NPC32771
0.6637	Remote Similarity	NPC326634
0.6626	Remote Similarity	NPC214142
0.6625	Remote Similarity	NPC472099
0.6625	Remote Similarity	NPC174760
0.6625	Remote Similarity	NPC132642
0.6625	Remote Similarity	NPC54066
0.6624	Remote Similarity	NPC478157
0.6624	Remote Similarity	NPC478158
0.6623	Remote Similarity	NPC317572
0.6623	Remote Similarity	NPC149708
0.6623	Remote Similarity	NPC476098
0.6623	Remote Similarity	NPC473640
0.6623	Remote Similarity	NPC472284
0.6622	Remote Similarity	NPC235684
0.6614	Remote Similarity	NPC91868
0.6614	Remote Similarity	NPC63971
0.661	Remote Similarity	NPC151976
0.661	Remote Similarity	NPC96405
0.661	Remote Similarity	NPC128084
0.661	Remote Similarity	NPC87856

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 NPC300114 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	646
0.2-0.3	950
0.3-0.4	1586
0.4-0.5	3156
0.5-0.6	1963
0.6-0.7	627
0.7-0.8	17
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
0.7545	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1229	Phase 2
0.7457	Intermediate Similarity	NPD3259	Approved
0.7371	Intermediate Similarity	NPD7673	Phase 3
0.7361	Intermediate Similarity	NPD4526	Approved
0.7361	Intermediate Similarity	NPD4529	Approved
0.7361	Intermediate Similarity	NPD4528	Approved
0.7313	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD1392	Approved
0.7257	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD3928	Approved
0.7252	Intermediate Similarity	NPD3931	Approved
0.719	Intermediate Similarity	NPD7576	Discontinued
0.7177	Intermediate Similarity	NPD8463	Approved
0.7172	Intermediate Similarity	NPD4349	Approved
0.7172	Intermediate Similarity	NPD4350	Approved
0.7167	Intermediate Similarity	NPD4454	Phase 2
0.7143	Intermediate Similarity	NPD1213	Phase 3
0.7126	Intermediate Similarity	NPD5450	Discontinued
0.7123	Intermediate Similarity	NPD802	Phase 2
0.7085	Intermediate Similarity	NPD484	Approved
0.7083	Intermediate Similarity	NPD7558	Phase 2
0.7082	Intermediate Similarity	NPD3258	Approved
0.7064	Intermediate Similarity	NPD7219	Approved
0.7064	Intermediate Similarity	NPD7221	Approved
0.7026	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4875	Phase 3
0.702	Intermediate Similarity	NPD4876	Phase 3
0.7014	Intermediate Similarity	NPD2076	Approved
0.7014	Intermediate Similarity	NPD2077	Approved
0.7009	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD3003	Approved
0.7004	Intermediate Similarity	NPD7001	Phase 3
0.6988	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD3280	Approved
0.6964	Remote Similarity	NPD1768	Approved
0.6963	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5612	Discontinued
0.6946	Remote Similarity	NPD4328	Approved
0.6939	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4418	Discontinued
0.6926	Remote Similarity	NPD7470	Discontinued
0.691	Remote Similarity	NPD3257	Approved
0.6908	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7453	Approved
0.69	Remote Similarity	NPD7222	Phase 2
0.69	Remote Similarity	NPD7452	Approved
0.6898	Remote Similarity	NPD6154	Approved
0.6897	Remote Similarity	NPD7069	Discontinued
0.6892	Remote Similarity	NPD1038	Approved
0.6881	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4086	Phase 1
0.6875	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7948	Phase 1
0.6872	Remote Similarity	NPD4373	Phase 2
0.6856	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7413	Phase 3
0.6853	Remote Similarity	NPD5482	Discontinued
0.6853	Remote Similarity	NPD5067	Phase 2
0.6853	Remote Similarity	NPD5066	Phase 2
0.6838	Remote Similarity	NPD5903	Approved
0.6838	Remote Similarity	NPD5902	Approved
0.6838	Remote Similarity	NPD4897	Phase 2
0.6837	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7426	Phase 1
0.6822	Remote Similarity	NPD5632	Approved
0.6822	Remote Similarity	NPD3354	Phase 2
0.682	Remote Similarity	NPD4203	Approved
0.682	Remote Similarity	NPD4204	Approved
0.6818	Remote Similarity	NPD4952	Phase 3
0.6818	Remote Similarity	NPD2383	Phase 1
0.6816	Remote Similarity	NPD6735	Approved
0.6813	Remote Similarity	NPD8102	Discontinued
0.6812	Remote Similarity	NPD31	Approved
0.6812	Remote Similarity	NPD4039	Approved
0.6812	Remote Similarity	NPD4122	Approved
0.6812	Remote Similarity	NPD4038	Approved
0.6812	Remote Similarity	NPD32	Approved
0.6812	Remote Similarity	NPD4034	Approved
0.6812	Remote Similarity	NPD4036	Approved
0.6812	Remote Similarity	NPD4035	Approved
0.6812	Remote Similarity	NPD4037	Approved
0.6812	Remote Similarity	NPD4033	Approved
0.6809	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5506	Approved
0.6807	Remote Similarity	NPD5507	Approved
0.6806	Remote Similarity	NPD7691	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2616	Phase 3
0.6795	Remote Similarity	NPD3243	Approved
0.6795	Remote Similarity	NPD2615	Phase 3
0.6783	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7963	Phase 3
0.6751	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6985	Discontinued
0.6749	Remote Similarity	NPD7567	Approved
0.6749	Remote Similarity	NPD8512	Phase 3
0.6741	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6494	Phase 2
0.6725	Remote Similarity	NPD6975	Discontinued
0.6724	Remote Similarity	NPD2916	Discontinued
0.6709	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD8356	Approved
0.6707	Remote Similarity	NPD6790	Phase 1
0.6707	Remote Similarity	NPD7417	Discontinued
0.6698	Remote Similarity	NPD750	Phase 2
0.6697	Remote Similarity	NPD6452	Discontinued
0.6696	Remote Similarity	NPD7777	Approved
0.6696	Remote Similarity	NPD6569	Phase 2
0.6696	Remote Similarity	NPD7778	Approved
0.6696	Remote Similarity	NPD53	Approved
0.6696	Remote Similarity	NPD2727	Phase 2
0.6694	Remote Similarity	NPD7675	Phase 3
0.6694	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7674	Phase 3
0.6693	Remote Similarity	NPD7169	Suspended
0.6681	Remote Similarity	NPD3816	Phase 1
0.6681	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD3815	Phase 1
0.6667	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7659	Discontinued
0.6667	Remote Similarity	NPD8430	Approved
0.6667	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4795	Phase 2
0.6654	Remote Similarity	NPD8255	Phase 2
0.6654	Remote Similarity	NPD8101	Phase 3
0.6653	Remote Similarity	NPD4343	Phase 1
0.6653	Remote Similarity	NPD4344	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD5945	Phase 1
0.6653	Remote Similarity	NPD7194	Discontinued
0.6653	Remote Similarity	NPD5944	Phase 1
0.6652	Remote Similarity	NPD5003	Discontinued
0.6652	Remote Similarity	NPD2509	Approved
0.6652	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD2510	Approved
0.6652	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4699	Discontinued
0.6639	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7555	Discontinued
0.6639	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1856	Discontinued
0.6637	Remote Similarity	NPD3395	Approved
0.6637	Remote Similarity	NPD3396	Approved
0.6637	Remote Similarity	NPD7944	Discontinued
0.6637	Remote Similarity	NPD4427	Phase 2
0.6627	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5875	Approved
0.6627	Remote Similarity	NPD5878	Approved
0.6626	Remote Similarity	NPD7603	Discontinued
0.6623	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD9689	Approved
0.6621	Remote Similarity	NPD5897	Approved
0.6621	Remote Similarity	NPD5899	Approved
0.6621	Remote Similarity	NPD5898	Approved
0.6617	Remote Similarity	NPD6709	Phase 3
0.6612	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7548	Discontinued
0.6612	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3330	Phase 1
0.6607	Remote Similarity	NPD6281	Approved
0.6607	Remote Similarity	NPD2564	Approved
0.6607	Remote Similarity	NPD2565	Phase 2
0.6595	Remote Similarity	NPD3397	Phase 2
0.6594	Remote Similarity	NPD9687	Approved
0.6594	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD9688	Approved
0.6594	Remote Similarity	NPD6999	Discontinued
0.6585	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.658	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2952	Discontinued
0.6577	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4889	Approved
0.657	Remote Similarity	NPD6736	Discontinued
0.6569	Remote Similarity	NPD8326	Phase 3
0.6569	Remote Similarity	NPD8325	Phase 3
0.6569	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3570	Phase 2
0.6565	Remote Similarity	NPD1739	Approved
0.6565	Remote Similarity	NPD1740	Approved
0.6565	Remote Similarity	NPD2305	Discontinued
0.6564	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2095	Phase 2
0.6561	Remote Similarity	NPD2094	Phase 2
0.6561	Remote Similarity	NPD2092	Phase 2
0.6561	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5596	Phase 2
0.6559	Remote Similarity	NPD7797	Approved
0.6559	Remote Similarity	NPD7796	Approved
0.6559	Remote Similarity	NPD7705	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7706	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8246	Approved
0.655	Remote Similarity	NPD8247	Approved
0.6549	Remote Similarity	NPD5317	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