NPASS Compound

Structure

NPC63571 OpenBabel07101718222D 38 41 0 0 0 0 0 0 0 0999 V2000 3.3317 -0.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5227 0.5759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2749 2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2453 0.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0839 1.4826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0234 1.5173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5861 1.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4476 3.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 1.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6112 0.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3292 1.8774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0724 1.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7201 1.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4476 2.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0234 -0.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9225 2.7910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2634 1.7961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8065 1.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9865 2.7514 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 8.6112 0.7083 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.3074 1.6695 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 7.3324 -1.0518 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.4225 3.6570 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.9865 2.7514 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3498 1.3893 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9975 1.8893 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3987 3.5605 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.0724 0.2083 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9280 2.6864 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3987 1.9424 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 5.3679 2.7906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7020 0.3070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 4 1 0 0 0 0 2 12 1 0 0 0 0 3 5 1 0 0 0 0 3 9 2 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 10 1 0 0 0 0 6 13 2 0 0 0 0 7 11 1 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 8 31 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 10 23 1 0 0 0 0 11 18 2 0 0 0 0 11 24 1 0 0 0 0 12 16 2 0 0 0 0 12 34 1 0 0 0 0 13 19 1 0 0 0 0 13 32 1 0 0 0 0 14 20 1 0 0 0 0 14 33 1 0 0 0 0 15 35 1 0 0 0 0 16 36 1 0 0 0 0 17 25 1 0 0 0 0 17 32 1 0 0 0 0 18 26 1 0 0 0 0 18 33 1 0 0 0 0 19 29 1 0 0 0 0 19 37 2 0 0 0 0 20 30 1 0 0 0 0 20 38 2 0 0 0 0 21 27 2 0 0 0 0 21 31 1 0 0 0 0 21 35 1 0 0 0 0 22 28 2 0 0 0 0 22 34 1 0 0 0 0 22 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	771.85
Volume:	527.887
LogP:	2.85
LogD:	3.08
LogS:	-3.077
# Rotatable Bonds:	11
TPSA:	200.97
# H-Bond Aceptor:	12
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.09
Synthetic Accessibility Score:	4.458
Fsp3:	0.136
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:	-5.88
MDCK Permeability:	1.504524152551312e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.996
20% Bioavailability (F20%):	0.238
30% Bioavailability (F30%):	0.602

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	97.7164306640625%
Volume Distribution (VD):	0.457
Pgp-substrate:	4.783073425292969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.291
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.553
CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.578
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.513

ADMET: Excretion

Clearance (CL):	1.647
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.969
Human Hepatotoxicity (H-HT):	0.999
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.404
Rat Oral Acute Toxicity:	0.986
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.252
Carcinogencity:	0.888
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC63571

Natural Product ID:	NPC63571
*Common Name:**	Nagelamide C
IUPAC Name:	N-[(E)-3-[2-amino-4-[(Z)-1-(2-amino-1H-imidazol-5-yl)-3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]prop-1-enyl]-1H-imidazol-5-yl]prop-2-enyl]-4,5-dibromo-1H-pyrrole-2-carboxamide
Synonyms:	Nagelamide C
Standard InCHIKey:	HVSCSPHJFJDZCZ-BARZBYPCSA-N
Standard InCHI:	InChI=1S/C22H20Br4N10O2/c23-10-6-13(32-17(10)25)19(37)29-4-1-2-12-16(36-22(28)34-12)9(15-8-31-21(27)35-15)3-5-30-20(38)14-7-11(24)18(26)33-14/h1-3,6-8,32-33H,4-5H2,(H,29,37)(H,30,38)(H3,27,31,35)(H3,28,34,36)/b2-1+,9-3-
SMILES:	C(=Cc1c(/C(=CCNC(=O)c2cc(c(Br)[nH]2)Br)/c2c[nH]c(=N)[nH]2)[nH]c(=N)[nH]1)/CNC(=O)c1cc(c(Br)[nH]1)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1162469
PubChem CID:	11491208
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000436] Azoles [CHEMONTID:0000078] Imidazoles [CHEMONTID:0002310] Substituted imidazoles [CHEMONTID:0002628] Trisubstituted imidazoles [CHEMONTID:0002631] 2,4,5-trisubstituted imidazoles

*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
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332839]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562840]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19209898]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584409]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	4.17	ug.mL-1	PMID[550729]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	33.3	ug.mL-1	PMID[550729]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	33.3	ug.mL-1	PMID[550729]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[550729]

☑ 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 NPC63571 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	2428
0.1-0.2	17212
0.2-0.3	16391
0.3-0.4	2716
0.4-0.5	2397
0.5-0.6	1260
0.6-0.7	221
0.7-0.8	48
0.8-0.85	4
0.85-0.9	11
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.982	High Similarity	NPC310633
0.976	High Similarity	NPC111566
0.9422	High Similarity	NPC19342
0.9162	High Similarity	NPC9635
0.905	High Similarity	NPC19696
0.905	High Similarity	NPC136957
0.903	High Similarity	NPC206148
0.8939	High Similarity	NPC475286
0.8939	High Similarity	NPC174281
0.8883	High Similarity	NPC48117
0.8883	High Similarity	NPC476526
0.8883	High Similarity	NPC329765
0.8798	High Similarity	NPC469716
0.8439	Intermediate Similarity	NPC54214
0.8436	Intermediate Similarity	NPC476527
0.8363	Intermediate Similarity	NPC73687
0.8359	Intermediate Similarity	NPC469717
0.8229	Intermediate Similarity	NPC28096
0.8229	Intermediate Similarity	NPC476421
0.8229	Intermediate Similarity	NPC227489
0.8192	Intermediate Similarity	NPC136441
0.815	Intermediate Similarity	NPC476418
0.8125	Intermediate Similarity	NPC226835
0.8125	Intermediate Similarity	NPC469976
0.8011	Intermediate Similarity	NPC472861
0.8011	Intermediate Similarity	NPC184932
0.799	Intermediate Similarity	NPC476524
0.799	Intermediate Similarity	NPC476525
0.7877	Intermediate Similarity	NPC80528
0.7833	Intermediate Similarity	NPC97106
0.7826	Intermediate Similarity	NPC469814
0.7811	Intermediate Similarity	NPC260041
0.7735	Intermediate Similarity	NPC37268
0.7684	Intermediate Similarity	NPC476414
0.768	Intermediate Similarity	NPC271927
0.7636	Intermediate Similarity	NPC150592
0.7632	Intermediate Similarity	NPC476413
0.7576	Intermediate Similarity	NPC20021
0.7568	Intermediate Similarity	NPC40530
0.7568	Intermediate Similarity	NPC314281
0.746	Intermediate Similarity	NPC112489
0.746	Intermediate Similarity	NPC46022
0.7459	Intermediate Similarity	NPC474696
0.7416	Intermediate Similarity	NPC27296
0.7403	Intermediate Similarity	NPC2414
0.7396	Intermediate Similarity	NPC210123
0.7303	Intermediate Similarity	NPC474236
0.7253	Intermediate Similarity	NPC306160
0.7231	Intermediate Similarity	NPC188821
0.7231	Intermediate Similarity	NPC474180
0.7213	Intermediate Similarity	NPC474383
0.7211	Intermediate Similarity	NPC270834
0.7194	Intermediate Similarity	NPC46811
0.7172	Intermediate Similarity	NPC474389
0.7101	Intermediate Similarity	NPC470703
0.7053	Intermediate Similarity	NPC470702
0.7053	Intermediate Similarity	NPC473218
0.7049	Intermediate Similarity	NPC473706
0.7022	Intermediate Similarity	NPC66642
0.7	Intermediate Similarity	NPC472260
0.6965	Remote Similarity	NPC477004
0.6927	Remote Similarity	NPC16659
0.6911	Remote Similarity	NPC240088
0.6911	Remote Similarity	NPC473380
0.6875	Remote Similarity	NPC265710
0.6872	Remote Similarity	NPC476423
0.6845	Remote Similarity	NPC233380
0.6828	Remote Similarity	NPC253687
0.6787	Remote Similarity	NPC474357
0.6773	Remote Similarity	NPC470323
0.6765	Remote Similarity	NPC77241
0.6765	Remote Similarity	NPC13456
0.6765	Remote Similarity	NPC166209
0.6765	Remote Similarity	NPC269203
0.6742	Remote Similarity	NPC267078
0.6742	Remote Similarity	NPC935
0.673	Remote Similarity	NPC469715
0.6716	Remote Similarity	NPC220797
0.6716	Remote Similarity	NPC474318
0.6716	Remote Similarity	NPC153123
0.6716	Remote Similarity	NPC201266
0.6716	Remote Similarity	NPC268744
0.6716	Remote Similarity	NPC475914
0.6701	Remote Similarity	NPC133003
0.6686	Remote Similarity	NPC23215
0.6686	Remote Similarity	NPC291517
0.6667	Remote Similarity	NPC50562
0.6667	Remote Similarity	NPC474195
0.6651	Remote Similarity	NPC475736
0.665	Remote Similarity	NPC477003
0.6636	Remote Similarity	NPC67658
0.6621	Remote Similarity	NPC474196
0.6617	Remote Similarity	NPC476460
0.6606	Remote Similarity	NPC156003
0.66	Remote Similarity	NPC473666
0.6599	Remote Similarity	NPC470205
0.6587	Remote Similarity	NPC317701
0.6576	Remote Similarity	NPC52110
0.6567	Remote Similarity	NPC324091
0.6554	Remote Similarity	NPC138596
0.6554	Remote Similarity	NPC195704
0.6554	Remote Similarity	NPC98156
0.6554	Remote Similarity	NPC200397
0.6554	Remote Similarity	NPC64661
0.6554	Remote Similarity	NPC167200
0.6554	Remote Similarity	NPC292434
0.6554	Remote Similarity	NPC14448
0.6546	Remote Similarity	NPC186068
0.654	Remote Similarity	NPC116555
0.6526	Remote Similarity	NPC247987
0.6524	Remote Similarity	NPC142688
0.6515	Remote Similarity	NPC117027
0.65	Remote Similarity	NPC169308
0.65	Remote Similarity	NPC209281
0.65	Remote Similarity	NPC48171
0.65	Remote Similarity	NPC12831
0.65	Remote Similarity	NPC286529
0.65	Remote Similarity	NPC205604
0.65	Remote Similarity	NPC244087
0.65	Remote Similarity	NPC97230
0.65	Remote Similarity	NPC3698
0.65	Remote Similarity	NPC17273
0.65	Remote Similarity	NPC59839
0.65	Remote Similarity	NPC77582
0.65	Remote Similarity	NPC141612
0.65	Remote Similarity	NPC135601
0.65	Remote Similarity	NPC302717
0.65	Remote Similarity	NPC74928
0.65	Remote Similarity	NPC129753
0.6495	Remote Similarity	NPC161861
0.6482	Remote Similarity	NPC21429
0.6471	Remote Similarity	NPC75135
0.6464	Remote Similarity	NPC101130
0.6464	Remote Similarity	NPC129412
0.6464	Remote Similarity	NPC58268
0.6464	Remote Similarity	NPC114033
0.6455	Remote Similarity	NPC243633
0.6455	Remote Similarity	NPC175150
0.6452	Remote Similarity	NPC267811
0.645	Remote Similarity	NPC99939
0.645	Remote Similarity	NPC308931
0.6417	Remote Similarity	NPC232798
0.6398	Remote Similarity	NPC473376
0.6394	Remote Similarity	NPC237414
0.6393	Remote Similarity	NPC168209
0.6392	Remote Similarity	NPC471943
0.6386	Remote Similarity	NPC473946
0.6382	Remote Similarity	NPC307191
0.6343	Remote Similarity	NPC477413
0.6333	Remote Similarity	NPC472288
0.6329	Remote Similarity	NPC102592
0.6329	Remote Similarity	NPC79356
0.6313	Remote Similarity	NPC284775
0.6313	Remote Similarity	NPC282247
0.6311	Remote Similarity	NPC304203
0.631	Remote Similarity	NPC471655
0.6293	Remote Similarity	NPC243716
0.6287	Remote Similarity	NPC474258
0.6283	Remote Similarity	NPC69843
0.6268	Remote Similarity	NPC171317
0.6263	Remote Similarity	NPC151635
0.625	Remote Similarity	NPC79777
0.625	Remote Similarity	NPC88110
0.625	Remote Similarity	NPC234403
0.625	Remote Similarity	NPC91179
0.6244	Remote Similarity	NPC477611
0.6238	Remote Similarity	NPC110158
0.6232	Remote Similarity	NPC326422
0.6225	Remote Similarity	NPC17059
0.6223	Remote Similarity	NPC17487
0.6223	Remote Similarity	NPC201831
0.6221	Remote Similarity	NPC320968
0.6211	Remote Similarity	NPC33229
0.6197	Remote Similarity	NPC477107
0.6197	Remote Similarity	NPC477108
0.6197	Remote Similarity	NPC477109
0.6193	Remote Similarity	NPC471193
0.6193	Remote Similarity	NPC471194
0.619	Remote Similarity	NPC109158
0.6186	Remote Similarity	NPC274981
0.6184	Remote Similarity	NPC477166
0.6184	Remote Similarity	NPC473342
0.6184	Remote Similarity	NPC477167
0.6184	Remote Similarity	NPC304187
0.6183	Remote Similarity	NPC204141
0.6169	Remote Similarity	NPC477042
0.6164	Remote Similarity	NPC54744
0.6158	Remote Similarity	NPC108011
0.6154	Remote Similarity	NPC17751
0.6154	Remote Similarity	NPC280864
0.6147	Remote Similarity	NPC72956
0.6143	Remote Similarity	NPC272174
0.6131	Remote Similarity	NPC469529
0.6126	Remote Similarity	NPC298288
0.6126	Remote Similarity	NPC477815
0.6124	Remote Similarity	NPC71236
0.6122	Remote Similarity	NPC109447
0.6119	Remote Similarity	NPC153980
0.6119	Remote Similarity	NPC6865
0.6119	Remote Similarity	NPC11126

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 NPC63571 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	1186
0.2-0.3	1972
0.3-0.4	2133
0.4-0.5	1984
0.5-0.6	1231
0.6-0.7	203
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7526	Intermediate Similarity	NPD7459	Phase 2
0.699	Remote Similarity	NPD5685	Approved
0.699	Remote Similarity	NPD5686	Approved
0.6733	Remote Similarity	NPD2289	Phase 3
0.6733	Remote Similarity	NPD2290	Phase 3
0.6699	Remote Similarity	NPD2442	Approved
0.6699	Remote Similarity	NPD2443	Approved
0.6667	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5643	Phase 2
0.6509	Remote Similarity	NPD2408	Discontinued
0.6493	Remote Similarity	NPD1506	Discontinued
0.6471	Remote Similarity	NPD460	Discontinued
0.6468	Remote Similarity	NPD5198	Approved
0.6468	Remote Similarity	NPD5199	Approved
0.6445	Remote Similarity	NPD2008	Discontinued
0.6432	Remote Similarity	NPD1600	Suspended
0.6425	Remote Similarity	NPD1982	Phase 1
0.6415	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.639	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6579	Phase 2
0.6337	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2405	Phase 3
0.6305	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD2880	Discontinued
0.6293	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD2411	Approved
0.6267	Remote Similarity	NPD7656	Approved
0.6267	Remote Similarity	NPD7657	Approved
0.6256	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5446	Phase 2
0.621	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7970	Approved
0.62	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD6470	Phase 3
0.6193	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD3319	Phase 1
0.6188	Remote Similarity	NPD3318	Approved
0.6188	Remote Similarity	NPD3320	Approved
0.6186	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD2367	Phase 2
0.6179	Remote Similarity	NPD5017	Discontinued
0.6158	Remote Similarity	NPD1031	Discontinued
0.6157	Remote Similarity	NPD6459	Phase 2
0.6154	Remote Similarity	NPD8256	Approved
0.6154	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8257	Approved
0.6146	Remote Similarity	NPD3246	Discontinued
0.6143	Remote Similarity	NPD1952	Discontinued
0.614	Remote Similarity	NPD3967	Approved
0.6124	Remote Similarity	NPD5853	Phase 3
0.6124	Remote Similarity	NPD5855	Phase 3
0.6114	Remote Similarity	NPD465	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3410	Approved
0.6111	Remote Similarity	NPD3411	Phase 2
0.6104	Remote Similarity	NPD6465	Phase 2
0.6103	Remote Similarity	NPD7817	Phase 1
0.6103	Remote Similarity	NPD3890	Phase 2
0.6103	Remote Similarity	NPD3891	Phase 2
0.6101	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD5854	Approved
0.6073	Remote Similarity	NPD4863	Approved
0.6071	Remote Similarity	NPD6210	Phase 3
0.607	Remote Similarity	NPD7865	Approved
0.6065	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD3178	Discontinued
0.6058	Remote Similarity	NPD1658	Discontinued
0.6055	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD3968	Approved
0.6053	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD438	Approved
0.6041	Remote Similarity	NPD439	Approved
0.6039	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD5973	Phase 2
0.6029	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD5974	Approved
0.6026	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1096	Discontinued
0.6	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6268	Phase 1
0.6	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7716	Approved
0.5991	Remote Similarity	NPD6664	Approved
0.5991	Remote Similarity	NPD6271	Approved
0.5991	Remote Similarity	NPD7717	Approved
0.5983	Remote Similarity	NPD6164	Phase 2
0.5983	Remote Similarity	NPD6165	Phase 2
0.5982	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD7406	Phase 2
0.5972	Remote Similarity	NPD7618	Phase 3
0.5972	Remote Similarity	NPD7619	Phase 3
0.5964	Remote Similarity	NPD3353	Approved
0.5962	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD3077	Approved
0.5961	Remote Similarity	NPD3079	Approved
0.5961	Remote Similarity	NPD3078	Approved
0.5961	Remote Similarity	NPD3076	Approved
0.596	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD1003	Phase 2
0.5956	Remote Similarity	NPD272	Approved
0.5952	Remote Similarity	NPD4922	Phase 2
0.5952	Remote Similarity	NPD1896	Approved
0.5945	Remote Similarity	NPD7208	Approved
0.5945	Remote Similarity	NPD7207	Approved
0.5945	Remote Similarity	NPD7209	Approved
0.5943	Remote Similarity	NPD7027	Phase 3
0.5942	Remote Similarity	NPD7026	Phase 2
0.5939	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD5962	Phase 2
0.5922	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.5919	Remote Similarity	NPD4395	Phase 1
0.5913	Remote Similarity	NPD4988	Discontinued
0.5913	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD3041	Approved
0.5905	Remote Similarity	NPD2892	Phase 1
0.5891	Remote Similarity	NPD4883	Approved
0.5891	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.589	Remote Similarity	NPD8322	Phase 2
0.5874	Remote Similarity	NPD2363	Discontinued
0.5872	Remote Similarity	NPD4299	Phase 1
0.5872	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD6828	Phase 2
0.5869	Remote Similarity	NPD1871	Approved
0.5865	Remote Similarity	NPD4940	Approved
0.586	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD3915	Approved
0.5855	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3927	Phase 2
0.5854	Remote Similarity	NPD5473	Discontinued
0.5848	Remote Similarity	NPD2547	Discontinued
0.5845	Remote Similarity	NPD5489	Phase 1
0.5845	Remote Similarity	NPD5491	Phase 3
0.5841	Remote Similarity	NPD1623	Approved
0.5837	Remote Similarity	NPD8317	Phase 2
0.5837	Remote Similarity	NPD8316	Phase 2
0.5837	Remote Similarity	NPD5935	Discontinued
0.583	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.583	Remote Similarity	NPD3917	Approved
0.583	Remote Similarity	NPD3918	Approved
0.5826	Remote Similarity	NPD4558	Phase 2
0.5825	Remote Similarity	NPD1895	Discontinued
0.5821	Remote Similarity	NPD1575	Approved
0.5821	Remote Similarity	NPD1573	Approved
0.582	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.5819	Remote Similarity	NPD7887	Approved
0.5819	Remote Similarity	NPD7888	Approved
0.5814	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7175	Phase 1
0.581	Remote Similarity	NPD5016	Approved
0.5808	Remote Similarity	NPD6771	Discontinued
0.5806	Remote Similarity	NPD7727	Phase 2
0.5806	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.5803	Remote Similarity	NPD3835	Phase 3
0.5803	Remote Similarity	NPD3833	Phase 3
0.58	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.5799	Remote Similarity	NPD8098	Approved
0.5799	Remote Similarity	NPD5426	Phase 3
0.5798	Remote Similarity	NPD9599	Approved
0.5798	Remote Similarity	NPD2222	Discontinued
0.5796	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD2061	Approved
0.5792	Remote Similarity	NPD7232	Discontinued
0.5789	Remote Similarity	NPD1996	Discontinued
0.5789	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4075	Phase 2
0.5784	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD6753	Phase 1
0.5783	Remote Similarity	NPD6752	Phase 1
0.578	Remote Similarity	NPD2879	Approved
0.578	Remote Similarity	NPD2881	Approved
0.5777	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.5777	Remote Similarity	NPD3989	Phase 3
0.5777	Remote Similarity	NPD5508	Phase 1
0.5775	Remote Similarity	NPD3460	Discontinued
0.5773	Remote Similarity	NPD7568	Phase 1
0.5773	Remote Similarity	NPD3248	Phase 1
0.5773	Remote Similarity	NPD2128	Phase 1
0.5769	Remote Similarity	NPD7564	Discontinued
0.5766	Remote Similarity	NPD5510	Approved
0.5764	Remote Similarity	NPD3868	Phase 1
0.5764	Remote Similarity	NPD4854	Phase 3
0.5762	Remote Similarity	NPD3961	Discontinued
0.5759	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.5759	Remote Similarity	NPD8096	Phase 3
0.5759	Remote Similarity	NPD8097	Phase 3
0.5755	Remote Similarity	NPD3517	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.575	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5749	Remote Similarity	NPD4649	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