NPASS Compound

Structure

NPC94752 OpenBabel07101718332D 33 35 0 0 1 0 0 0 0 0999 V2000 -6.1779 -3.8166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8178 -5.5108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1487 -6.2539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2435 -3.1928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2946 -0.5476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3164 -0.3397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6036 -1.4986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 -1.0828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9344 -2.2418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5306 -4.3518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5088 -4.5597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 -2.0339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8615 -5.0949 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5962 -3.7281 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9271 -4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8833 -4.8870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1705 -6.0460 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -4.2633 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 -2.5743 -3.9360 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 -5.4223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2142 -5.6302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 28 1 0 0 0 0 4 31 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 20 2 0 0 0 0 11 20 1 0 0 0 0 12 22 2 0 0 0 0 13 23 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 30 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 23 30 1 0 0 0 0 24 16 1 1 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 25 17 1 1 0 0 0 25 26 1 0 0 0 0 25 31 1 0 0 0 0 26 29 2 3 0 0 0 26 32 1 0 0 0 0 27 31 1 0 0 0 0 27 33 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.28
Volume:	487.718
LogP:	3.822
LogD:	3.923
LogS:	-3.389
# Rotatable Bonds:	13
TPSA:	77.23
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	3.103
Fsp3:	0.407
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.777
MDCK Permeability:	5.570062785409391e-05
Pgp-inhibitor:	0.74
Pgp-substrate:	0.492
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.53
Plasma Protein Binding (PPB):	88.93212127685547%
Volume Distribution (VD):	1.936
Pgp-substrate:	9.745194435119629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.216
CYP1A2-substrate:	0.445
CYP2C19-inhibitor:	0.935
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.737
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.9
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.958
CYP3A4-substrate:	0.587

ADMET: Excretion

Clearance (CL):	8.258
Half-life (T1/2):	0.784

ADMET: Toxicity

hERG Blockers:	0.522
Human Hepatotoxicity (H-HT):	0.821
Drug-inuced Liver Injury (DILI):	0.224
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.457
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.075
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.114

Download Data

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

Natural Product: NPC94752

Natural Product ID:	NPC94752
*Common Name:**	Xenortide B
IUPAC Name:	(2S)-N-[(2S)-1-[2-(1H-indol-3-yl)ethylamino]-1-oxo-3-phenylpropan-2-yl]-N,4-dimethyl-2-(methylamino)pentanamide
Synonyms:
Standard InCHIKey:	SOIIKURIVIWMKK-DQEYMECFSA-N
Standard InCHI:	InChI=1S/C27H36N4O2/c1-19(2)16-24(28-3)27(33)31(4)25(17-20-10-6-5-7-11-20)26(32)29-15-14-21-18-30-23-13-9-8-12-22(21)23/h5-13,18-19,24-25,28,30H,14-17H2,1-4H3,(H,29,32)/t24-,25-/m0/s1
SMILES:	CC(C)C[C@@H](C(=O)N(C)[C@@H](Cc1ccccc1)C(=NCCc1c[nH]c2ccccc12)O)NC
Synthetic Gene Cluster:	BGC0000465;
ChEMBL Identifier:	CHEMBL486287
PubChem CID:	24900169
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
NPO33013	xenorhabdus nematophilus	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18491867]
NPO8987	Xenorhabdus nematophila	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25080196]
NPO8987	Xenorhabdus nematophila	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	6

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	13690.0	nM	PMID[471277]
NPT176	Organism	Artemia salina	Artemia salina	IC50	=	200.0	ug.mL-1	PMID[471276]
NPT2258	Organism	Plasmodium falciparum NF54	Plasmodium falciparum NF54	IC50	=	760.0	nM	PMID[471277]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	111200.0	nM	PMID[471277]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	11700.0	nM	PMID[471277]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	1570.0	nM	PMID[471277]

☑ 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 NPC94752 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	314
0.1-0.2	2813
0.2-0.3	16473
0.3-0.4	15615
0.4-0.5	2618
0.5-0.6	2452
0.6-0.7	1466
0.7-0.8	782
0.8-0.85	125
0.85-0.9	33
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9302	High Similarity	NPC213629
0.9294	High Similarity	NPC228835
0.9101	High Similarity	NPC171317
0.9059	High Similarity	NPC11126
0.8914	High Similarity	NPC17059
0.8913	High Similarity	NPC54420
0.884	High Similarity	NPC293917
0.8817	High Similarity	NPC162860
0.8785	High Similarity	NPC473640
0.8772	High Similarity	NPC469938
0.8743	High Similarity	NPC165495
0.8743	High Similarity	NPC475506
0.8736	High Similarity	NPC100321
0.8717	High Similarity	NPC478158
0.8703	High Similarity	NPC473376
0.8698	High Similarity	NPC160105
0.8696	High Similarity	NPC155143
0.8677	High Similarity	NPC75634
0.8621	High Similarity	NPC126709
0.8621	High Similarity	NPC248041
0.8606	High Similarity	NPC469760
0.8606	High Similarity	NPC259644
0.8606	High Similarity	NPC469765
0.8606	High Similarity	NPC469763
0.8606	High Similarity	NPC469786
0.8606	High Similarity	NPC25008
0.8606	High Similarity	NPC73952
0.8588	High Similarity	NPC474561
0.8588	High Similarity	NPC49954
0.8579	High Similarity	NPC110602
0.8579	High Similarity	NPC31385
0.8579	High Similarity	NPC75726
0.8563	High Similarity	NPC14113
0.8563	High Similarity	NPC145885
0.8563	High Similarity	NPC84827
0.8556	High Similarity	NPC117244
0.8556	High Similarity	NPC473763
0.8554	High Similarity	NPC70922
0.8554	High Similarity	NPC212376
0.8554	High Similarity	NPC75540
0.8554	High Similarity	NPC211572
0.8554	High Similarity	NPC80597
0.8549	High Similarity	NPC281049
0.8547	High Similarity	NPC321708
0.8538	High Similarity	NPC63751
0.8519	High Similarity	NPC223791
0.8519	High Similarity	NPC107077
0.8514	High Similarity	NPC213468
0.8514	High Similarity	NPC283219
0.8506	High Similarity	NPC267885
0.8497	Intermediate Similarity	NPC314603
0.849	Intermediate Similarity	NPC478157
0.8466	Intermediate Similarity	NPC91179
0.8454	Intermediate Similarity	NPC477714
0.8452	Intermediate Similarity	NPC469762
0.8448	Intermediate Similarity	NPC149155
0.8448	Intermediate Similarity	NPC110500
0.8448	Intermediate Similarity	NPC203468
0.8429	Intermediate Similarity	NPC320968
0.8415	Intermediate Similarity	NPC294693
0.8412	Intermediate Similarity	NPC282231
0.8393	Intermediate Similarity	NPC469785
0.8385	Intermediate Similarity	NPC471194
0.8385	Intermediate Similarity	NPC153980
0.8385	Intermediate Similarity	NPC471193
0.8385	Intermediate Similarity	NPC6865
0.8363	Intermediate Similarity	NPC311276
0.8353	Intermediate Similarity	NPC279918
0.8352	Intermediate Similarity	NPC59269
0.8342	Intermediate Similarity	NPC54744
0.8342	Intermediate Similarity	NPC300183
0.8333	Intermediate Similarity	NPC72956
0.8333	Intermediate Similarity	NPC235684
0.8324	Intermediate Similarity	NPC201700
0.8308	Intermediate Similarity	NPC477715
0.8278	Intermediate Similarity	NPC99939
0.8278	Intermediate Similarity	NPC308931
0.8278	Intermediate Similarity	NPC15102
0.8256	Intermediate Similarity	NPC194640
0.8251	Intermediate Similarity	NPC243716
0.8242	Intermediate Similarity	NPC314372
0.8218	Intermediate Similarity	NPC78020
0.8212	Intermediate Similarity	NPC233936
0.8202	Intermediate Similarity	NPC219336
0.8201	Intermediate Similarity	NPC476874
0.8191	Intermediate Similarity	NPC470497
0.8182	Intermediate Similarity	NPC470499
0.8163	Intermediate Similarity	NPC471192
0.8161	Intermediate Similarity	NPC54988
0.8159	Intermediate Similarity	NPC319232
0.8159	Intermediate Similarity	NPC24370
0.8155	Intermediate Similarity	NPC24678
0.8155	Intermediate Similarity	NPC105818
0.815	Intermediate Similarity	NPC40779
0.815	Intermediate Similarity	NPC64216
0.8146	Intermediate Similarity	NPC183662
0.8146	Intermediate Similarity	NPC217372
0.8146	Intermediate Similarity	NPC15573
0.8128	Intermediate Similarity	NPC262898
0.8121	Intermediate Similarity	NPC190296
0.8118	Intermediate Similarity	NPC195239
0.8118	Intermediate Similarity	NPC157828
0.81	Intermediate Similarity	NPC155444
0.8079	Intermediate Similarity	NPC161861
0.8075	Intermediate Similarity	NPC11445
0.8075	Intermediate Similarity	NPC179701
0.8068	Intermediate Similarity	NPC194411
0.8059	Intermediate Similarity	NPC200214
0.8056	Intermediate Similarity	NPC16659
0.8045	Intermediate Similarity	NPC68354
0.8045	Intermediate Similarity	NPC248454
0.8039	Intermediate Similarity	NPC326363
0.8033	Intermediate Similarity	NPC62749
0.8033	Intermediate Similarity	NPC474707
0.8024	Intermediate Similarity	NPC470440
0.8023	Intermediate Similarity	NPC299594
0.8022	Intermediate Similarity	NPC477003
0.8011	Intermediate Similarity	NPC47190
0.8	Intermediate Similarity	NPC469779
0.8	Intermediate Similarity	NPC469783
0.8	Intermediate Similarity	NPC469784
0.8	Intermediate Similarity	NPC469768
0.8	Intermediate Similarity	NPC265710
0.8	Intermediate Similarity	NPC248462
0.8	Intermediate Similarity	NPC469767
0.8	Intermediate Similarity	NPC469761
0.8	Intermediate Similarity	NPC469780
0.799	Intermediate Similarity	NPC191382
0.799	Intermediate Similarity	NPC56109
0.7989	Intermediate Similarity	NPC265576
0.798	Intermediate Similarity	NPC470732
0.798	Intermediate Similarity	NPC470731
0.7977	Intermediate Similarity	NPC135141
0.7977	Intermediate Similarity	NPC92796
0.7957	Intermediate Similarity	NPC476460
0.7956	Intermediate Similarity	NPC300688
0.7956	Intermediate Similarity	NPC469896
0.7952	Intermediate Similarity	NPC469766
0.7951	Intermediate Similarity	NPC69843
0.7946	Intermediate Similarity	NPC173028
0.7946	Intermediate Similarity	NPC65215
0.7944	Intermediate Similarity	NPC111275
0.7944	Intermediate Similarity	NPC64436
0.7944	Intermediate Similarity	NPC473380
0.7944	Intermediate Similarity	NPC151939
0.7944	Intermediate Similarity	NPC240088
0.7941	Intermediate Similarity	NPC53947
0.7939	Intermediate Similarity	NPC73767
0.7937	Intermediate Similarity	NPC227582
0.7933	Intermediate Similarity	NPC37423
0.7933	Intermediate Similarity	NPC275305
0.7931	Intermediate Similarity	NPC131718
0.7923	Intermediate Similarity	NPC323752
0.7917	Intermediate Similarity	NPC159856
0.7917	Intermediate Similarity	NPC193761
0.7912	Intermediate Similarity	NPC71037
0.7901	Intermediate Similarity	NPC55772
0.7895	Intermediate Similarity	NPC131887
0.7892	Intermediate Similarity	NPC204565
0.7892	Intermediate Similarity	NPC317030
0.7885	Intermediate Similarity	NPC325976
0.788	Intermediate Similarity	NPC133003
0.788	Intermediate Similarity	NPC280290
0.7876	Intermediate Similarity	NPC317701
0.7874	Intermediate Similarity	NPC230869
0.7869	Intermediate Similarity	NPC163055
0.7864	Intermediate Similarity	NPC477176
0.7864	Intermediate Similarity	NPC470730
0.7864	Intermediate Similarity	NPC470729
0.7864	Intermediate Similarity	NPC477175
0.7861	Intermediate Similarity	NPC285469
0.7847	Intermediate Similarity	NPC478028
0.7846	Intermediate Similarity	NPC323927
0.7845	Intermediate Similarity	NPC284775
0.7841	Intermediate Similarity	NPC271734
0.7831	Intermediate Similarity	NPC110126
0.7826	Intermediate Similarity	NPC474877
0.7826	Intermediate Similarity	NPC475969
0.7826	Intermediate Similarity	NPC475859
0.7826	Intermediate Similarity	NPC472294
0.7826	Intermediate Similarity	NPC477177
0.7824	Intermediate Similarity	NPC471957
0.7824	Intermediate Similarity	NPC476073
0.7818	Intermediate Similarity	NPC84911
0.7812	Intermediate Similarity	NPC252338
0.7807	Intermediate Similarity	NPC95783
0.7802	Intermediate Similarity	NPC215795
0.7802	Intermediate Similarity	NPC176199
0.7795	Intermediate Similarity	NPC475288
0.7788	Intermediate Similarity	NPC165743
0.7788	Intermediate Similarity	NPC89987
0.7784	Intermediate Similarity	NPC98715
0.7778	Intermediate Similarity	NPC474177
0.7778	Intermediate Similarity	NPC321911
0.7773	Intermediate Similarity	NPC478029
0.7772	Intermediate Similarity	NPC470205
0.7772	Intermediate Similarity	NPC471944
0.7772	Intermediate Similarity	NPC48938
0.7771	Intermediate Similarity	NPC56765
0.7771	Intermediate Similarity	NPC206819

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 NPC94752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	496
0.2-0.3	963
0.3-0.4	1447
0.4-0.5	2288
0.5-0.6	2265
0.6-0.7	1233
0.7-0.8	234
0.8-0.85	34
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8913	High Similarity	NPD8493	Clinical (unspecified phase)
0.884	High Similarity	NPD7621	Clinical (unspecified phase)
0.8827	High Similarity	NPD7618	Phase 3
0.8827	High Similarity	NPD7619	Phase 3
0.8793	High Similarity	NPD5728	Clinical (unspecified phase)
0.8602	High Similarity	NPD8272	Phase 2
0.8596	High Similarity	NPD3961	Discontinued
0.8511	High Similarity	NPD6838	Clinical (unspecified phase)
0.8488	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8454	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD482	Approved
0.8441	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD7470	Discontinued
0.8415	Intermediate Similarity	NPD7944	Discontinued
0.84	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD8093	Discontinued
0.8385	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8371	Intermediate Similarity	NPD2094	Phase 2
0.8371	Intermediate Similarity	NPD2092	Phase 2
0.8371	Intermediate Similarity	NPD2095	Phase 2
0.8362	Intermediate Similarity	NPD6595	Phase 3
0.8343	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD2091	Phase 2
0.8324	Intermediate Similarity	NPD2096	Phase 2
0.8308	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD4075	Phase 2
0.8286	Intermediate Similarity	NPD750	Phase 2
0.8239	Intermediate Similarity	NPD5065	Approved
0.8226	Intermediate Similarity	NPD6664	Approved
0.8187	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD8431	Approved
0.8177	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD8094	Discontinued
0.8146	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8119	Intermediate Similarity	NPD7731	Approved
0.8119	Intermediate Similarity	NPD7730	Approved
0.8114	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8109	Intermediate Similarity	NPD7271	Approved
0.8101	Intermediate Similarity	NPD4076	Approved
0.8101	Intermediate Similarity	NPD4079	Approved
0.8073	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD7957	Phase 1
0.8069	Intermediate Similarity	NPD7603	Discontinued
0.8063	Intermediate Similarity	NPD8072	Approved
0.8045	Intermediate Similarity	NPD3506	Approved
0.8045	Intermediate Similarity	NPD3505	Approved
0.8045	Intermediate Similarity	NPD2144	Approved
0.8039	Intermediate Similarity	NPD7824	Approved
0.8033	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD8322	Phase 2
0.802	Intermediate Similarity	NPD7970	Approved
0.802	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD3038	Discontinued
0.801	Intermediate Similarity	NPD7952	Approved
0.801	Intermediate Similarity	NPD7789	Approved
0.801	Intermediate Similarity	NPD7791	Approved
0.801	Intermediate Similarity	NPD7950	Approved
0.801	Intermediate Similarity	NPD7953	Approved
0.801	Intermediate Similarity	NPD7790	Approved
0.801	Intermediate Similarity	NPD7951	Approved
0.801	Intermediate Similarity	NPD8073	Approved
0.799	Intermediate Similarity	NPD7780	Approved
0.799	Intermediate Similarity	NPD7781	Approved
0.7944	Intermediate Similarity	NPD4181	Approved
0.794	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD786	Approved
0.7935	Intermediate Similarity	NPD6217	Discontinued
0.7933	Intermediate Similarity	NPD4128	Approved
0.7927	Intermediate Similarity	NPD5426	Phase 3
0.7908	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7711	Discontinued
0.7882	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD1722	Approved
0.7841	Intermediate Similarity	NPD3583	Phase 2
0.7806	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6771	Discontinued
0.7778	Intermediate Similarity	NPD3100	Discontinued
0.7772	Intermediate Similarity	NPD7817	Phase 1
0.7758	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD7948	Phase 1
0.7744	Intermediate Similarity	NPD8114	Approved
0.7744	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD8115	Approved
0.7742	Intermediate Similarity	NPD7026	Phase 2
0.7742	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3323	Discontinued
0.7733	Intermediate Similarity	NPD4463	Approved
0.7733	Intermediate Similarity	NPD4462	Approved
0.773	Intermediate Similarity	NPD7564	Discontinued
0.773	Intermediate Similarity	NPD6178	Phase 3
0.773	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6665	Discontinued
0.7709	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD5017	Discontinued
0.7663	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD5901	Discontinued
0.7632	Intermediate Similarity	NPD4922	Phase 2
0.7629	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4638	Approved
0.7611	Intermediate Similarity	NPD4640	Approved
0.7611	Intermediate Similarity	NPD4639	Approved
0.7609	Intermediate Similarity	NPD8386	Phase 2
0.7596	Intermediate Similarity	NPD6044	Discontinued
0.7596	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7727	Phase 2
0.7588	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD6999	Discontinued
0.7568	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD8289	Discontinued
0.7543	Intermediate Similarity	NPD2837	Discontinued
0.7538	Intermediate Similarity	NPD484	Approved
0.7529	Intermediate Similarity	NPD2172	Phase 1
0.7528	Intermediate Similarity	NPD2511	Approved
0.7527	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2641	Approved
0.7514	Intermediate Similarity	NPD4703	Approved
0.7514	Intermediate Similarity	NPD4326	Phase 2
0.7514	Intermediate Similarity	NPD2640	Approved
0.7514	Intermediate Similarity	NPD4702	Approved
0.75	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7308	Discontinued
0.7475	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD8169	Discontinued
0.7473	Intermediate Similarity	NPD1326	Approved
0.7473	Intermediate Similarity	NPD1325	Approved
0.7471	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD7665	Phase 2
0.745	Intermediate Similarity	NPD7666	Phase 3
0.7449	Intermediate Similarity	NPD4601	Approved
0.7449	Intermediate Similarity	NPD4600	Approved
0.7448	Intermediate Similarity	NPD5505	Discontinued
0.7446	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5140	Approved
0.7444	Intermediate Similarity	NPD5138	Approved
0.7438	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7001	Phase 3
0.7433	Intermediate Similarity	NPD3178	Discontinued
0.7432	Intermediate Similarity	NPD3610	Approved
0.7432	Intermediate Similarity	NPD3609	Approved
0.743	Intermediate Similarity	NPD1403	Approved
0.743	Intermediate Similarity	NPD1404	Approved
0.743	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6165	Phase 2
0.7429	Intermediate Similarity	NPD6164	Phase 2
0.7424	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD5021	Discontinued
0.7418	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD8256	Approved
0.7415	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD8257	Approved
0.7407	Intermediate Similarity	NPD5555	Phase 1
0.7394	Intermediate Similarity	NPD3320	Approved
0.7394	Intermediate Similarity	NPD3318	Approved
0.7394	Intermediate Similarity	NPD3319	Phase 1
0.7391	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8026	Phase 1
0.7385	Intermediate Similarity	NPD2880	Discontinued
0.7374	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6268	Phase 1
0.7371	Intermediate Similarity	NPD8641	Approved
0.7371	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7717	Approved
0.7368	Intermediate Similarity	NPD7716	Approved
0.7363	Intermediate Similarity	NPD2639	Approved
0.7363	Intermediate Similarity	NPD2642	Approved
0.7358	Intermediate Similarity	NPD3404	Approved
0.7356	Intermediate Similarity	NPD7469	Discontinued
0.7354	Intermediate Similarity	NPD7482	Phase 2
0.7354	Intermediate Similarity	NPD7483	Phase 2
0.7347	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5254	Discontinued
0.7336	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5105	Approved
0.7302	Intermediate Similarity	NPD5106	Approved
0.7287	Intermediate Similarity	NPD6452	Discontinued
0.7286	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7187	Phase 2
0.7283	Intermediate Similarity	NPD3717	Discontinued
0.7277	Intermediate Similarity	NPD2510	Approved
0.7277	Intermediate Similarity	NPD2509	Approved
0.7277	Intermediate Similarity	NPD5809	Phase 3
0.7273	Intermediate Similarity	NPD8122	Approved
0.7273	Intermediate Similarity	NPD8123	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