NPASS Compound

Structure

NPC476414 OpenBabel07101719122D 30 31 0 0 1 0 0 0 0 0999 V2000 -1.0327 4.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4921 3.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0108 4.7601 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 -0.8660 3.5000 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 -0.8660 1.5000 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 0.9230 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 4.5388 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 2.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6443 5.3479 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.8198 5.3479 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.0799 4.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -3.2709 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 3.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 3.8090 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 -2.0108 1.2399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 16 1 0 0 0 0 6 20 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 30 1 0 0 0 0 9 10 1 0 0 0 0 9 11 2 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 25 2 0 0 0 0 14 16 1 0 0 0 0 14 22 2 0 0 0 0 14 26 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 27 30 1 0 0 0 0 28 30 2 0 0 0 0 29 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	569.99
Volume:	422.005
LogP:	-0.649
LogD:	-0.169
LogS:	-1.73
# Rotatable Bonds:	11
TPSA:	159.12
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	4.102
Fsp3:	0.562
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.724
MDCK Permeability:	1.0980744264088571e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.427
Human Intestinal Absorption (HIA):	0.978
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.742
Plasma Protein Binding (PPB):	70.68266296386719%
Volume Distribution (VD):	1.776
Pgp-substrate:	49.55617141723633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.573
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.185
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.388
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	2.889
Half-life (T1/2):	0.45

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.092
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.321
Skin Sensitization:	0.193
Carcinogencity:	0.439
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.481

Download Data

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

Natural Product: NPC476414

Natural Product ID:	NPC476414
*Common Name:**	Mauritamide C
IUPAC Name:	2-[[2-amino-4-[3-[(4,5-dibromo-1-methylpyrrole-2-carbonyl)amino]propyl]-3-ethyl-5-oxoimidazol-4-yl]amino]ethanesulfonic acid
Synonyms:	Mauritamide C
Standard InCHIKey:	XDWMDZGQJUBHGC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H24Br2N6O5S/c1-3-24-15(19)22-14(26)16(24,21-7-8-30(27,28)29)5-4-6-20-13(25)11-9-10(17)12(18)23(11)2/h9,21H,3-8H2,1-2H3,(H,20,25)(H2,19,22,26)(H,27,28,29)
SMILES:	CCN1C(=N)N=C(C1(CCCNC(=O)c1cc(c(n1C)Br)Br)NCCS(=O)(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598107
PubChem CID:	46232063
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:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO33334	agelas sponges	Species	Agelasidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[20061160]

☑ 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
MIC	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	98.6	%	PMID[536286]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	35000.0	nM	PMID[536286]

☑ 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 NPC476414 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	976
0.1-0.2	16091
0.2-0.3	17900
0.3-0.4	3181
0.4-0.5	3352
0.5-0.6	1072
0.6-0.7	79
0.7-0.8	38
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9942	High Similarity	NPC476413
0.8713	High Similarity	NPC306160
0.8497	Intermediate Similarity	NPC476418
0.8352	Intermediate Similarity	NPC469814
0.8325	Intermediate Similarity	NPC469716
0.8268	Intermediate Similarity	NPC97106
0.8122	Intermediate Similarity	NPC136441
0.8079	Intermediate Similarity	NPC206148
0.7968	Intermediate Similarity	NPC112489
0.7958	Intermediate Similarity	NPC46811
0.7956	Intermediate Similarity	NPC28096
0.7956	Intermediate Similarity	NPC227489
0.7956	Intermediate Similarity	NPC476421
0.7956	Intermediate Similarity	NPC226835
0.7955	Intermediate Similarity	NPC27296
0.7872	Intermediate Similarity	NPC46022
0.7857	Intermediate Similarity	NPC54214
0.7814	Intermediate Similarity	NPC80528
0.774	Intermediate Similarity	NPC474236
0.7684	Intermediate Similarity	NPC111566
0.7684	Intermediate Similarity	NPC63571
0.766	Intermediate Similarity	NPC184932
0.766	Intermediate Similarity	NPC472861
0.7644	Intermediate Similarity	NPC310633
0.7637	Intermediate Similarity	NPC474383
0.7626	Intermediate Similarity	NPC9635
0.7574	Intermediate Similarity	NPC476524
0.7486	Intermediate Similarity	NPC73687
0.7449	Intermediate Similarity	NPC19342
0.7448	Intermediate Similarity	NPC476423
0.7416	Intermediate Similarity	NPC469717
0.7402	Intermediate Similarity	NPC476525
0.735	Intermediate Similarity	NPC19696
0.735	Intermediate Similarity	NPC136957
0.7345	Intermediate Similarity	NPC260041
0.734	Intermediate Similarity	NPC271927
0.733	Intermediate Similarity	NPC314281
0.733	Intermediate Similarity	NPC40530
0.7302	Intermediate Similarity	NPC37268
0.7286	Intermediate Similarity	NPC476526
0.7286	Intermediate Similarity	NPC48117
0.7286	Intermediate Similarity	NPC329765
0.7283	Intermediate Similarity	NPC473706
0.725	Intermediate Similarity	NPC475286
0.725	Intermediate Similarity	NPC174281
0.7196	Intermediate Similarity	NPC469976
0.7172	Intermediate Similarity	NPC210123
0.7143	Intermediate Similarity	NPC109158
0.7128	Intermediate Similarity	NPC474696
0.7069	Intermediate Similarity	NPC150592
0.6914	Remote Similarity	NPC20021
0.6818	Remote Similarity	NPC270834
0.6811	Remote Similarity	NPC52110
0.68	Remote Similarity	NPC476527
0.6791	Remote Similarity	NPC298288
0.6719	Remote Similarity	NPC2414
0.6695	Remote Similarity	NPC66642
0.662	Remote Similarity	NPC469715
0.6579	Remote Similarity	NPC142688
0.6545	Remote Similarity	NPC475736
0.6425	Remote Similarity	NPC243716
0.6393	Remote Similarity	NPC472288
0.6372	Remote Similarity	NPC473376
0.6364	Remote Similarity	NPC474180
0.6364	Remote Similarity	NPC188821
0.6341	Remote Similarity	NPC263117
0.6341	Remote Similarity	NPC125181
0.6341	Remote Similarity	NPC242872
0.6339	Remote Similarity	NPC474195
0.6335	Remote Similarity	NPC472260
0.6321	Remote Similarity	NPC474389
0.6303	Remote Similarity	NPC77061
0.63	Remote Similarity	NPC474196
0.6269	Remote Similarity	NPC33229
0.6188	Remote Similarity	NPC50562
0.6166	Remote Similarity	NPC321939
0.6161	Remote Similarity	NPC67658
0.6158	Remote Similarity	NPC476419
0.6146	Remote Similarity	NPC91179
0.6143	Remote Similarity	NPC54744
0.6131	Remote Similarity	NPC233380
0.6126	Remote Similarity	NPC320968
0.6114	Remote Similarity	NPC476817
0.6108	Remote Similarity	NPC291517
0.6099	Remote Similarity	NPC110602
0.6099	Remote Similarity	NPC31385
0.6099	Remote Similarity	NPC471194
0.6099	Remote Similarity	NPC153980
0.6099	Remote Similarity	NPC75726
0.6099	Remote Similarity	NPC6865
0.6099	Remote Similarity	NPC471193
0.6095	Remote Similarity	NPC213629
0.6093	Remote Similarity	NPC171317
0.6068	Remote Similarity	NPC16659
0.6065	Remote Similarity	NPC477004
0.6059	Remote Similarity	NPC288074
0.6054	Remote Similarity	NPC72956
0.6049	Remote Similarity	NPC473380
0.6049	Remote Similarity	NPC240088
0.6048	Remote Similarity	NPC17059
0.6047	Remote Similarity	NPC262898
0.6022	Remote Similarity	NPC23215
0.6019	Remote Similarity	NPC265710
0.6011	Remote Similarity	NPC71236
0.6009	Remote Similarity	NPC477167
0.6009	Remote Similarity	NPC156003
0.6009	Remote Similarity	NPC304187
0.6009	Remote Similarity	NPC473342
0.6009	Remote Similarity	NPC477166
0.6	Remote Similarity	NPC243633
0.6	Remote Similarity	NPC175150
0.6	Remote Similarity	NPC94752
0.6	Remote Similarity	NPC179701
0.6	Remote Similarity	NPC162268
0.5991	Remote Similarity	NPC71238
0.5989	Remote Similarity	NPC292434
0.5989	Remote Similarity	NPC200397
0.5989	Remote Similarity	NPC14448
0.5989	Remote Similarity	NPC195704
0.5989	Remote Similarity	NPC167200
0.5989	Remote Similarity	NPC138596
0.5989	Remote Similarity	NPC98156
0.5989	Remote Similarity	NPC64661
0.5981	Remote Similarity	NPC228835
0.5979	Remote Similarity	NPC13432
0.5973	Remote Similarity	NPC471191
0.5952	Remote Similarity	NPC133003
0.5947	Remote Similarity	NPC471192
0.5947	Remote Similarity	NPC147983
0.5947	Remote Similarity	NPC177996
0.5941	Remote Similarity	NPC109447
0.5939	Remote Similarity	NPC168209
0.5934	Remote Similarity	NPC201831
0.5934	Remote Similarity	NPC17487
0.5929	Remote Similarity	NPC470703
0.5915	Remote Similarity	NPC69843
0.5911	Remote Similarity	NPC54981
0.5909	Remote Similarity	NPC477108
0.5909	Remote Similarity	NPC477107
0.5909	Remote Similarity	NPC477109
0.5905	Remote Similarity	NPC64216
0.5885	Remote Similarity	NPC470702
0.5885	Remote Similarity	NPC473218
0.588	Remote Similarity	NPC294693
0.5879	Remote Similarity	NPC475870
0.5874	Remote Similarity	NPC186068
0.5871	Remote Similarity	NPC253687
0.5869	Remote Similarity	NPC209917
0.5865	Remote Similarity	NPC165743
0.5865	Remote Similarity	NPC11126
0.5864	Remote Similarity	NPC209281
0.5864	Remote Similarity	NPC302717
0.5864	Remote Similarity	NPC48171
0.5864	Remote Similarity	NPC286529
0.5864	Remote Similarity	NPC74928
0.5864	Remote Similarity	NPC244087
0.5864	Remote Similarity	NPC98864
0.5864	Remote Similarity	NPC205604
0.5864	Remote Similarity	NPC3698
0.5864	Remote Similarity	NPC97230
0.5864	Remote Similarity	NPC129753
0.5864	Remote Similarity	NPC12831
0.5864	Remote Similarity	NPC77582
0.5864	Remote Similarity	NPC169308
0.5864	Remote Similarity	NPC59839
0.5857	Remote Similarity	NPC159125
0.5856	Remote Similarity	NPC88115
0.5845	Remote Similarity	NPC293917
0.5841	Remote Similarity	NPC268966
0.584	Remote Similarity	NPC63279
0.5833	Remote Similarity	NPC114033
0.5833	Remote Similarity	NPC101130
0.5833	Remote Similarity	NPC129412
0.5833	Remote Similarity	NPC58268
0.5825	Remote Similarity	NPC64055
0.5823	Remote Similarity	NPC474877
0.5823	Remote Similarity	NPC475859
0.5823	Remote Similarity	NPC475969
0.5817	Remote Similarity	NPC14849
0.5816	Remote Similarity	NPC297642
0.5812	Remote Similarity	NPC19170
0.5808	Remote Similarity	NPC470731
0.5808	Remote Similarity	NPC470732
0.5804	Remote Similarity	NPC54420
0.5799	Remote Similarity	NPC248782
0.5799	Remote Similarity	NPC473640
0.5797	Remote Similarity	NPC469529
0.5794	Remote Similarity	NPC327095
0.5794	Remote Similarity	NPC312942
0.5792	Remote Similarity	NPC475506
0.5789	Remote Similarity	NPC478030
0.5781	Remote Similarity	NPC470730
0.5781	Remote Similarity	NPC477175
0.5781	Remote Similarity	NPC470729
0.5781	Remote Similarity	NPC477176
0.5779	Remote Similarity	NPC75135
0.5776	Remote Similarity	NPC272174
0.5775	Remote Similarity	NPC17273
0.5775	Remote Similarity	NPC135601
0.5775	Remote Similarity	NPC141612

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 NPC476414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1058
0.2-0.3	1739
0.3-0.4	2367
0.4-0.5	2924
0.5-0.6	819
0.6-0.7	21
0.7-0.8	0
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
0.7044	Intermediate Similarity	NPD7459	Phase 2
0.6618	Remote Similarity	NPD2290	Phase 3
0.6618	Remote Similarity	NPD2289	Phase 3
0.6524	Remote Similarity	NPD2405	Phase 3
0.6509	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5686	Approved
0.6456	Remote Similarity	NPD5685	Approved
0.6409	Remote Similarity	NPD7970	Approved
0.6409	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD1096	Discontinued
0.6313	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8169	Discontinued
0.6275	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7817	Phase 1
0.6233	Remote Similarity	NPD5017	Discontinued
0.6222	Remote Similarity	NPD5198	Approved
0.6222	Remote Similarity	NPD5199	Approved
0.6209	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD6173	Approved
0.6157	Remote Similarity	NPD4963	Approved
0.6157	Remote Similarity	NPD4962	Approved
0.615	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4960	Approved
0.6136	Remote Similarity	NPD4959	Approved
0.6117	Remote Similarity	NPD3178	Discontinued
0.6111	Remote Similarity	NPD4961	Approved
0.6109	Remote Similarity	NPD3968	Approved
0.6094	Remote Similarity	NPD5935	Discontinued
0.6091	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD3411	Phase 2
0.6018	Remote Similarity	NPD3410	Approved
0.6009	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD6369	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8272	Phase 2
0.6	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD3967	Approved
0.5964	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.5953	Remote Similarity	NPD953	Approved
0.5947	Remote Similarity	NPD3353	Approved
0.5946	Remote Similarity	NPD4415	Approved
0.5936	Remote Similarity	NPD3890	Phase 2
0.5936	Remote Similarity	NPD3891	Phase 2
0.5933	Remote Similarity	NPD1745	Approved
0.5932	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD5643	Phase 2
0.5919	Remote Similarity	NPD2442	Approved
0.5919	Remote Similarity	NPD2443	Approved
0.5919	Remote Similarity	NPD7232	Discontinued
0.5917	Remote Similarity	NPD3292	Discontinued
0.5913	Remote Similarity	NPD6210	Phase 3
0.5913	Remote Similarity	NPD3989	Phase 3
0.5905	Remote Similarity	NPD7716	Approved
0.5905	Remote Similarity	NPD7717	Approved
0.5895	Remote Similarity	NPD1623	Approved
0.5891	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD3990	Phase 3
0.5875	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.587	Remote Similarity	NPD1031	Discontinued
0.5867	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD7727	Phase 2
0.5856	Remote Similarity	NPD8114	Approved
0.5856	Remote Similarity	NPD8115	Approved
0.5853	Remote Similarity	NPD7027	Phase 3
0.5845	Remote Similarity	NPD4091	Approved
0.5845	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD510	Phase 1
0.5833	Remote Similarity	NPD2547	Discontinued
0.5833	Remote Similarity	NPD460	Discontinued
0.583	Remote Similarity	NPD7568	Phase 1
0.583	Remote Similarity	NPD4904	Approved
0.5826	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD1952	Discontinued
0.5822	Remote Similarity	NPD1600	Suspended
0.5822	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD5510	Approved
0.5817	Remote Similarity	NPD4092	Approved
0.5813	Remote Similarity	NPD4887	Discontinued
0.5787	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD4903	Approved
0.5785	Remote Similarity	NPD2893	Phase 3
0.5785	Remote Similarity	NPD2130	Discontinued
0.5785	Remote Similarity	NPD4905	Approved
0.5785	Remote Similarity	NPD4906	Approved
0.5782	Remote Similarity	NPD2137	Approved
0.5782	Remote Similarity	NPD2138	Approved
0.5778	Remote Similarity	NPD6487	Approved
0.5778	Remote Similarity	NPD6486	Approved
0.5771	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD2367	Phase 2
0.5769	Remote Similarity	NPD6752	Phase 1
0.5769	Remote Similarity	NPD6753	Phase 1
0.5766	Remote Similarity	NPD3497	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD1631	Approved
0.5763	Remote Similarity	NPD6165	Phase 2
0.5763	Remote Similarity	NPD6164	Phase 2
0.576	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD2408	Discontinued
0.5748	Remote Similarity	NPD5461	Discontinued
0.5747	Remote Similarity	NPD2912	Approved
0.5747	Remote Similarity	NPD2911	Approved
0.5742	Remote Similarity	NPD3996	Approved
0.5742	Remote Similarity	NPD3993	Approved
0.5742	Remote Similarity	NPD3992	Approved
0.5742	Remote Similarity	NPD3991	Approved
0.5742	Remote Similarity	NPD3994	Approved
0.5742	Remote Similarity	NPD3995	Approved
0.5741	Remote Similarity	NPD1658	Discontinued
0.5741	Remote Similarity	NPD3517	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD2892	Phase 1
0.5728	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD1575	Approved
0.5728	Remote Similarity	NPD1573	Approved
0.5721	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD3522	Approved
0.5721	Remote Similarity	NPD2847	Phase 2
0.5714	Remote Similarity	NPD3998	Approved
0.5714	Remote Similarity	NPD3999	Approved
0.5714	Remote Similarity	NPD981	Phase 2
0.5714	Remote Similarity	NPD3997	Approved
0.5708	Remote Similarity	NPD6579	Phase 2
0.5707	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD3915	Approved
0.5689	Remote Similarity	NPD2008	Discontinued
0.5683	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD1174	Phase 2
0.5678	Remote Similarity	NPD2180	Approved
0.5677	Remote Similarity	NPD3918	Approved
0.5677	Remote Similarity	NPD3917	Approved
0.5677	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.5677	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD750	Phase 2
0.5673	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD7888	Approved
0.5672	Remote Similarity	NPD7887	Approved
0.5667	Remote Similarity	NPD5840	Discontinued
0.5664	Remote Similarity	NPD1506	Discontinued
0.5663	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD8261	Discontinued
0.5656	Remote Similarity	NPD4397	Phase 1
0.5656	Remote Similarity	NPD4364	Phase 1
0.5652	Remote Similarity	NPD5679	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD1657	Approved
0.5647	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD2813	Phase 3
0.5647	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.5646	Remote Similarity	NPD3108	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD3380	Phase 3
0.5644	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD3379	Phase 2
0.5642	Remote Similarity	NPD6665	Discontinued
0.5642	Remote Similarity	NPD3288	Approved
0.564	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.5637	Remote Similarity	NPD8026	Phase 1
0.5634	Remote Similarity	NPD5092	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD438	Approved
0.5631	Remote Similarity	NPD439	Approved
0.5631	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD5611	Phase 2
0.5628	Remote Similarity	NPD971	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD7026	Phase 2
0.5628	Remote Similarity	NPD5809	Phase 3
0.5627	Remote Similarity	NPD6153	Approved
0.5625	Remote Similarity	NPD6268	Phase 1
0.5625	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.5622	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.5622	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.5622	Remote Similarity	NPD6470	Phase 3
0.5622	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.562	Remote Similarity	NPD8159	Discontinued
0.5619	Remote Similarity	NPD6044	Discontinued
0.5619	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD2222	Discontinued
0.5619	Remote Similarity	NPD5906	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD1630	Approved
0.5614	Remote Similarity	NPD4520	Approved
0.5613	Remote Similarity	NPD1643	Phase 3
0.5611	Remote Similarity	NPD2880	Discontinued
0.5609	Remote Similarity	NPD7656	Approved
0.5609	Remote Similarity	NPD7657	Approved
0.5607	Remote Similarity	NPD7482	Phase 2
0.5607	Remote Similarity	NPD7483	Phase 2
0.5607	Remote Similarity	NPD721	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