NPASS Compound

Structure

NPC71684 OpenBabel07101718192D 30 31 0 0 1 0 0 0 0 0999 V2000 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 26 1 0 0 0 0 4 28 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 22 17 1 6 0 0 0 22 25 1 0 0 0 0 22 26 1 0 0 0 0 23 18 1 6 0 0 0 23 24 1 0 0 0 0 23 28 1 0 0 0 0 24 27 2 3 0 0 0 24 29 1 0 0 0 0 25 28 1 0 0 0 0 25 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	409.27
Volume:	453.322
LogP:	3.694
LogD:	3.951
LogS:	-3.348
# Rotatable Bonds:	13
TPSA:	61.44
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.6
Synthetic Accessibility Score:	2.873
Fsp3:	0.44
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.824
MDCK Permeability:	9.955303539754823e-05
Pgp-inhibitor:	0.602
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.541
Plasma Protein Binding (PPB):	89.21686553955078%
Volume Distribution (VD):	2.373
Pgp-substrate:	9.937562942504883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.389
CYP2D6-inhibitor:	0.841
CYP2D6-substrate:	0.729
CYP3A4-inhibitor:	0.94
CYP3A4-substrate:	0.726

ADMET: Excretion

Clearance (CL):	9.175
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.349
Human Hepatotoxicity (H-HT):	0.812
Drug-inuced Liver Injury (DILI):	0.216
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.061
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.09

Download Data

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

Natural Product: NPC71684

Natural Product ID:	NPC71684
*Common Name:**	Xenortide A
IUPAC Name:	(2S)-N,4-dimethyl-2-(methylamino)-N-[(2S)-1-oxo-3-phenyl-1-(2-phenylethylamino)propan-2-yl]pentanamide
Synonyms:
Standard InCHIKey:	UAFFXYUNGBKFSK-GOTSBHOMSA-N
Standard InCHI:	InChI=1S/C25H35N3O2/c1-19(2)17-22(26-3)25(30)28(4)23(18-21-13-9-6-10-14-21)24(29)27-16-15-20-11-7-5-8-12-20/h5-14,19,22-23,26H,15-18H2,1-4H3,(H,27,29)/t22-,23-/m0/s1
SMILES:	CC(C)C[C@@H](C(=O)N(C)[C@@H](Cc1ccccc1)C(=NCCc1ccccc1)O)NC
Synthetic Gene Cluster:	BGC0000465;
ChEMBL Identifier:	CHEMBL486084
PubChem CID:	24900168
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	=	115500.0	nM	PMID[555281]
NPT176	Organism	Artemia salina	Artemia salina	IC50	=	200.0	ug.mL-1	PMID[555280]
NPT2258	Organism	Plasmodium falciparum NF54	Plasmodium falciparum NF54	IC50	=	19200.0	nM	PMID[555281]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	124500.0	nM	PMID[555281]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	22500.0	nM	PMID[555281]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	46400.0	nM	PMID[555281]

☑ 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 NPC71684 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	127
0.1-0.2	1152
0.2-0.3	8910
0.3-0.4	17952
0.4-0.5	11316
0.5-0.6	2273
0.6-0.7	653
0.7-0.8	275
0.8-0.85	25
0.85-0.9	7
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9304	High Similarity	NPC470545
0.9224	High Similarity	NPC470546
0.9217	High Similarity	NPC470544
0.8828	High Similarity	NPC132636
0.8699	High Similarity	NPC101719
0.864	High Similarity	NPC473322
0.864	High Similarity	NPC111428
0.8618	High Similarity	NPC222466
0.8559	High Similarity	NPC33742
0.8475	Intermediate Similarity	NPC276949
0.8475	Intermediate Similarity	NPC35850
0.8468	Intermediate Similarity	NPC22746
0.8417	Intermediate Similarity	NPC239357
0.8387	Intermediate Similarity	NPC6975
0.8359	Intermediate Similarity	NPC255447
0.8333	Intermediate Similarity	NPC477937
0.8293	Intermediate Similarity	NPC200964
0.8226	Intermediate Similarity	NPC202521
0.822	Intermediate Similarity	NPC319579
0.819	Intermediate Similarity	NPC327481
0.8145	Intermediate Similarity	NPC476990
0.814	Intermediate Similarity	NPC200589
0.8125	Intermediate Similarity	NPC319766
0.8115	Intermediate Similarity	NPC285926
0.8115	Intermediate Similarity	NPC315276
0.8115	Intermediate Similarity	NPC14672
0.8083	Intermediate Similarity	NPC474584
0.8077	Intermediate Similarity	NPC130309
0.8045	Intermediate Similarity	NPC127741
0.8016	Intermediate Similarity	NPC252878
0.7958	Intermediate Similarity	NPC469903
0.7956	Intermediate Similarity	NPC315266
0.7953	Intermediate Similarity	NPC46427
0.7941	Intermediate Similarity	NPC161069
0.7895	Intermediate Similarity	NPC141050
0.7863	Intermediate Similarity	NPC300315
0.784	Intermediate Similarity	NPC220698
0.7826	Intermediate Similarity	NPC209509
0.7797	Intermediate Similarity	NPC67043
0.7797	Intermediate Similarity	NPC473418
0.7794	Intermediate Similarity	NPC239762
0.7794	Intermediate Similarity	NPC163392
0.7778	Intermediate Similarity	NPC68865
0.7762	Intermediate Similarity	NPC473002
0.774	Intermediate Similarity	NPC469902
0.774	Intermediate Similarity	NPC469243
0.774	Intermediate Similarity	NPC473003
0.7714	Intermediate Similarity	NPC138775
0.7692	Intermediate Similarity	NPC122590
0.7692	Intermediate Similarity	NPC473341
0.7687	Intermediate Similarity	NPC287401
0.7674	Intermediate Similarity	NPC474082
0.7674	Intermediate Similarity	NPC175726
0.7674	Intermediate Similarity	NPC35996
0.7664	Intermediate Similarity	NPC476259
0.7652	Intermediate Similarity	NPC469666
0.7647	Intermediate Similarity	NPC471265
0.7647	Intermediate Similarity	NPC471264
0.763	Intermediate Similarity	NPC248283
0.7627	Intermediate Similarity	NPC164859
0.7619	Intermediate Similarity	NPC471527
0.7619	Intermediate Similarity	NPC475544
0.7609	Intermediate Similarity	NPC168113
0.7609	Intermediate Similarity	NPC269398
0.7609	Intermediate Similarity	NPC263493
0.7603	Intermediate Similarity	NPC324850
0.7589	Intermediate Similarity	NPC311658
0.7589	Intermediate Similarity	NPC16188
0.7584	Intermediate Similarity	NPC223207
0.7583	Intermediate Similarity	NPC45033
0.7565	Intermediate Similarity	NPC25565
0.7561	Intermediate Similarity	NPC329011
0.7559	Intermediate Similarity	NPC314992
0.7554	Intermediate Similarity	NPC139326
0.7554	Intermediate Similarity	NPC468984
0.7554	Intermediate Similarity	NPC197682
0.7554	Intermediate Similarity	NPC176226
0.7554	Intermediate Similarity	NPC77905
0.7551	Intermediate Similarity	NPC62104
0.7551	Intermediate Similarity	NPC1390
0.7535	Intermediate Similarity	NPC105717
0.7533	Intermediate Similarity	NPC471771
0.7533	Intermediate Similarity	NPC290755
0.7533	Intermediate Similarity	NPC304074
0.7518	Intermediate Similarity	NPC314114
0.7518	Intermediate Similarity	NPC262077
0.75	Intermediate Similarity	NPC475439
0.75	Intermediate Similarity	NPC52748
0.75	Intermediate Similarity	NPC473501
0.75	Intermediate Similarity	NPC311242
0.75	Intermediate Similarity	NPC233702
0.7483	Intermediate Similarity	NPC2501
0.7483	Intermediate Similarity	NPC254798
0.7482	Intermediate Similarity	NPC476989
0.7482	Intermediate Similarity	NPC469427
0.7482	Intermediate Similarity	NPC469426
0.7481	Intermediate Similarity	NPC246079
0.7481	Intermediate Similarity	NPC325479
0.7478	Intermediate Similarity	NPC303045
0.7478	Intermediate Similarity	NPC161972
0.7466	Intermediate Similarity	NPC473580
0.7464	Intermediate Similarity	NPC178662
0.7464	Intermediate Similarity	NPC476133
0.7464	Intermediate Similarity	NPC470884
0.7464	Intermediate Similarity	NPC89489
0.7464	Intermediate Similarity	NPC92784
0.7464	Intermediate Similarity	NPC98424
0.746	Intermediate Similarity	NPC197470
0.7447	Intermediate Similarity	NPC316008
0.7447	Intermediate Similarity	NPC313867
0.7447	Intermediate Similarity	NPC5620
0.7445	Intermediate Similarity	NPC314835
0.7438	Intermediate Similarity	NPC473498
0.7434	Intermediate Similarity	NPC469904
0.7432	Intermediate Similarity	NPC287757
0.7432	Intermediate Similarity	NPC469898
0.7432	Intermediate Similarity	NPC319320
0.7431	Intermediate Similarity	NPC7817
0.7431	Intermediate Similarity	NPC475168
0.7417	Intermediate Similarity	NPC275467
0.7402	Intermediate Similarity	NPC2265
0.7394	Intermediate Similarity	NPC314358
0.7386	Intermediate Similarity	NPC198254
0.7386	Intermediate Similarity	NPC274198
0.7376	Intermediate Similarity	NPC476978
0.7376	Intermediate Similarity	NPC315283
0.7376	Intermediate Similarity	NPC314388
0.7373	Intermediate Similarity	NPC12730
0.7372	Intermediate Similarity	NPC474473
0.7353	Intermediate Similarity	NPC326966
0.7351	Intermediate Similarity	NPC22883
0.7351	Intermediate Similarity	NPC5719
0.7351	Intermediate Similarity	NPC210377
0.7351	Intermediate Similarity	NPC217804
0.7351	Intermediate Similarity	NPC63931
0.7351	Intermediate Similarity	NPC189116
0.7329	Intermediate Similarity	NPC286551
0.7329	Intermediate Similarity	NPC202198
0.7324	Intermediate Similarity	NPC322878
0.7313	Intermediate Similarity	NPC239990
0.7313	Intermediate Similarity	NPC152850
0.7313	Intermediate Similarity	NPC89923
0.7313	Intermediate Similarity	NPC71933
0.7313	Intermediate Similarity	NPC105114
0.731	Intermediate Similarity	NPC324081
0.7308	Intermediate Similarity	NPC27833
0.7303	Intermediate Similarity	NPC15068
0.7293	Intermediate Similarity	NPC474479
0.7292	Intermediate Similarity	NPC471820
0.7292	Intermediate Similarity	NPC471821
0.729	Intermediate Similarity	NPC475532
0.7288	Intermediate Similarity	NPC322598
0.7286	Intermediate Similarity	NPC46098
0.7286	Intermediate Similarity	NPC307357
0.7286	Intermediate Similarity	NPC268841
0.7279	Intermediate Similarity	NPC470902
0.7273	Intermediate Similarity	NPC276506
0.726	Intermediate Similarity	NPC300443
0.7255	Intermediate Similarity	NPC63040
0.7255	Intermediate Similarity	NPC328649
0.7244	Intermediate Similarity	NPC165285
0.7241	Intermediate Similarity	NPC129666
0.7241	Intermediate Similarity	NPC13470
0.7239	Intermediate Similarity	NPC136453
0.723	Intermediate Similarity	NPC476268
0.7226	Intermediate Similarity	NPC257390
0.7222	Intermediate Similarity	NPC329761
0.7222	Intermediate Similarity	NPC135121
0.7222	Intermediate Similarity	NPC225648
0.7222	Intermediate Similarity	NPC145113
0.7219	Intermediate Similarity	NPC73655
0.7219	Intermediate Similarity	NPC241794
0.7217	Intermediate Similarity	NPC226438
0.7214	Intermediate Similarity	NPC313694
0.7214	Intermediate Similarity	NPC242159
0.7211	Intermediate Similarity	NPC56685
0.7209	Intermediate Similarity	NPC169328
0.7208	Intermediate Similarity	NPC280022
0.7203	Intermediate Similarity	NPC201244
0.7203	Intermediate Similarity	NPC10781
0.7203	Intermediate Similarity	NPC293628
0.7203	Intermediate Similarity	NPC477217
0.7203	Intermediate Similarity	NPC122493
0.7197	Intermediate Similarity	NPC196243
0.7192	Intermediate Similarity	NPC473491
0.719	Intermediate Similarity	NPC471317
0.719	Intermediate Similarity	NPC61004
0.7176	Intermediate Similarity	NPC477061
0.7176	Intermediate Similarity	NPC45777
0.7164	Intermediate Similarity	NPC47667
0.7154	Intermediate Similarity	NPC310467
0.7154	Intermediate Similarity	NPC237420
0.7153	Intermediate Similarity	NPC81026
0.7153	Intermediate Similarity	NPC157311
0.7152	Intermediate Similarity	NPC469901
0.7152	Intermediate Similarity	NPC473001
0.7133	Intermediate Similarity	NPC197743
0.7133	Intermediate Similarity	NPC297145
0.7131	Intermediate Similarity	NPC88267
0.7131	Intermediate Similarity	NPC194390

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 NPC71684 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	112
0.1-0.2	330
0.2-0.3	783
0.3-0.4	1734
0.4-0.5	3495
0.5-0.6	1991
0.6-0.7	564
0.7-0.8	130
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9016	High Similarity	NPD5339	Clinical (unspecified phase)
0.8512	High Similarity	NPD4504	Clinical (unspecified phase)
0.8473	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD4677	Discontinued
0.8359	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.8281	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD7720	Phase 2
0.8154	Intermediate Similarity	NPD5581	Approved
0.814	Intermediate Similarity	NPD5263	Approved
0.811	Intermediate Similarity	NPD5367	Discontinued
0.8095	Intermediate Similarity	NPD3071	Approved
0.8095	Intermediate Similarity	NPD3073	Approved
0.8095	Intermediate Similarity	NPD3072	Approved
0.8074	Intermediate Similarity	NPD8076	Discontinued
0.8045	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD6623	Phase 3
0.8016	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.8016	Intermediate Similarity	NPD4761	Approved
0.8016	Intermediate Similarity	NPD4762	Approved
0.8	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD6901	Phase 3
0.7971	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6073	Approved
0.7907	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7130	Phase 3
0.7863	Intermediate Similarity	NPD4676	Approved
0.7852	Intermediate Similarity	NPD6294	Approved
0.7852	Intermediate Similarity	NPD6295	Approved
0.7846	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD3040	Approved
0.7786	Intermediate Similarity	NPD4177	Approved
0.7786	Intermediate Similarity	NPD4175	Approved
0.7754	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD6681	Discovery
0.773	Intermediate Similarity	NPD6088	Approved
0.7721	Intermediate Similarity	NPD6852	Discontinued
0.771	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD4151	Approved
0.7704	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5725	Approved
0.7647	Intermediate Similarity	NPD8173	Phase 2
0.7647	Intermediate Similarity	NPD8172	Phase 2
0.763	Intermediate Similarity	NPD5323	Approved
0.7623	Intermediate Similarity	NPD3643	Approved
0.7623	Intermediate Similarity	NPD3644	Approved
0.7623	Intermediate Similarity	NPD3642	Approved
0.7612	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD5299	Approved
0.7611	Intermediate Similarity	NPD1814	Approved
0.7611	Intermediate Similarity	NPD1812	Approved
0.76	Intermediate Similarity	NPD7508	Discontinued
0.7594	Intermediate Similarity	NPD4125	Approved
0.7589	Intermediate Similarity	NPD8323	Discontinued
0.7574	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD8643	Discontinued
0.7571	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD2217	Approved
0.7559	Intermediate Similarity	NPD2218	Phase 2
0.7556	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD2088	Approved
0.7554	Intermediate Similarity	NPD2087	Approved
0.7538	Intermediate Similarity	NPD2584	Suspended
0.7537	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1967	Approved
0.7518	Intermediate Similarity	NPD8125	Discontinued
0.7518	Intermediate Similarity	NPD1968	Approved
0.75	Intermediate Similarity	NPD999	Phase 2
0.75	Intermediate Similarity	NPD4153	Approved
0.75	Intermediate Similarity	NPD5296	Approved
0.75	Intermediate Similarity	NPD5717	Approved
0.7483	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1330	Phase 2
0.7465	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD1348	Approved
0.7447	Intermediate Similarity	NPD5024	Approved
0.7445	Intermediate Similarity	NPD3908	Approved
0.7442	Intermediate Similarity	NPD7342	Discontinued
0.7434	Intermediate Similarity	NPD7485	Phase 3
0.7434	Intermediate Similarity	NPD7484	Phase 3
0.7426	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD3626	Phase 3
0.7388	Intermediate Similarity	NPD7828	Discontinued
0.7379	Intermediate Similarity	NPD7303	Discontinued
0.7344	Intermediate Similarity	NPD3806	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4126	Approved
0.7299	Intermediate Similarity	NPD5747	Discontinued
0.7297	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3125	Approved
0.7279	Intermediate Similarity	NPD2045	Approved
0.7279	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2043	Approved
0.7279	Intermediate Similarity	NPD2051	Approved
0.7279	Intermediate Similarity	NPD2048	Approved
0.7279	Intermediate Similarity	NPD2046	Approved
0.7279	Intermediate Similarity	NPD2047	Approved
0.7279	Intermediate Similarity	NPD2044	Approved
0.7279	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD21	Approved
0.7266	Intermediate Similarity	NPD3123	Discovery
0.7266	Intermediate Similarity	NPD5162	Approved
0.726	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5716	Approved
0.725	Intermediate Similarity	NPD4119	Approved
0.7246	Intermediate Similarity	NPD8416	Discontinued
0.7246	Intermediate Similarity	NPD8265	Approved
0.7244	Intermediate Similarity	NPD747	Discontinued
0.7241	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2014	Approved
0.7241	Intermediate Similarity	NPD2013	Approved
0.7241	Intermediate Similarity	NPD2016	Approved
0.7239	Intermediate Similarity	NPD3029	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7450	Phase 2
0.7234	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4214	Discontinued
0.7213	Intermediate Similarity	NPD1040	Phase 2
0.7209	Intermediate Similarity	NPD7522	Discontinued
0.7203	Intermediate Similarity	NPD9566	Approved
0.7192	Intermediate Similarity	NPD5941	Approved
0.7192	Intermediate Similarity	NPD4432	Discontinued
0.7192	Intermediate Similarity	NPD5942	Approved
0.7183	Intermediate Similarity	NPD2022	Approved
0.7167	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5630	Phase 1
0.7164	Intermediate Similarity	NPD5578	Approved
0.7164	Intermediate Similarity	NPD6792	Phase 3
0.7164	Intermediate Similarity	NPD2031	Discontinued
0.7164	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD8315	Phase 1
0.7155	Intermediate Similarity	NPD6690	Approved
0.7154	Intermediate Similarity	NPD6093	Discontinued
0.7153	Intermediate Similarity	NPD5298	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7613	Discontinued
0.7143	Intermediate Similarity	NPD5230	Approved
0.7143	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5229	Approved
0.7143	Intermediate Similarity	NPD5335	Discontinued
0.7132	Intermediate Similarity	NPD5759	Approved
0.7109	Intermediate Similarity	NPD3551	Approved
0.7095	Intermediate Similarity	NPD7131	Phase 3
0.7089	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD480	Approved
0.7083	Intermediate Similarity	NPD5264	Approved
0.7083	Intermediate Similarity	NPD5265	Approved
0.7078	Intermediate Similarity	NPD8303	Discontinued
0.7054	Intermediate Similarity	NPD4031	Approved
0.7054	Intermediate Similarity	NPD4032	Approved
0.7047	Intermediate Similarity	NPD4647	Approved
0.7047	Intermediate Similarity	NPD4648	Approved
0.7047	Intermediate Similarity	NPD4646	Approved
0.7042	Intermediate Similarity	NPD4158	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7599	Phase 2
0.7031	Intermediate Similarity	NPD3598	Phase 3
0.7029	Intermediate Similarity	NPD4794	Discontinued
0.7027	Intermediate Similarity	NPD5748	Phase 2
0.702	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7105	Phase 1
0.7014	Intermediate Similarity	NPD2437	Approved
0.7014	Intermediate Similarity	NPD2436	Approved
0.7014	Intermediate Similarity	NPD6119	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5614	Approved
0.7007	Intermediate Similarity	NPD5613	Approved
0.7	Intermediate Similarity	NPD4117	Approved
0.6993	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7600	Phase 2
0.6986	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5981	Approved
0.697	Remote Similarity	NPD1922	Discontinued
0.6954	Remote Similarity	NPD2891	Approved
0.6935	Remote Similarity	NPD1766	Approved
0.6935	Remote Similarity	NPD1767	Approved
0.6935	Remote Similarity	NPD1763	Approved
0.6935	Remote Similarity	NPD1765	Approved
0.6935	Remote Similarity	NPD1761	Approved
0.6934	Remote Similarity	NPD3588	Discontinued
0.6929	Remote Similarity	NPD4254	Approved
0.6929	Remote Similarity	NPD941	Approved
0.6929	Remote Similarity	NPD4253	Approved
0.6923	Remote Similarity	NPD6865	Phase 2
0.6923	Remote Similarity	NPD6864	Phase 2
0.6923	Remote Similarity	NPD3480	Approved
0.6918	Remote Similarity	NPD6676	Phase 2
0.6917	Remote Similarity	NPD6806	Phase 1
0.6917	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5638	Approved
0.6906	Remote Similarity	NPD3136	Phase 2
0.6901	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1370	Approved
0.6899	Remote Similarity	NPD1374	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