NPASS Compound

Structure

NPC310633 OpenBabel07101719252D 38 41 0 0 1 0 0 0 0 0999 V2000 2.7024 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7024 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4394 -1.5134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2024 -2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1085 -2.2565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7902 -5.3558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4771 -3.2530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7400 -3.4814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 -1.7213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7413 -5.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3431 -2.7530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2024 -4.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7339 -2.5838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1522 -2.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7413 -4.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1352 -1.7748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2024 -4.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7558 -2.7918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7989 -3.9814 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 6.5503 -5.6346 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -7.2566 -3.1597 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.5503 -3.4590 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.8043 -1.0317 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.6079 -4.5692 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7024 -3.6808 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0866 -2.0486 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1522 -4.2904 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7902 -3.7378 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1407 -1.6703 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7989 -2.9814 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 2.7024 -5.4128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4468 -3.7428 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 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 3 1 6 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:	773.87
Volume:	530.524
LogP:	2.595
LogD:	2.877
LogS:	-3.239
# Rotatable Bonds:	12
TPSA:	200.64
# H-Bond Aceptor:	12
# H-Bond Donor:	10
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.109
Synthetic Accessibility Score:	4.223
Fsp3:	0.182
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:	-5.86
MDCK Permeability:	9.682035852165427e-06
Pgp-inhibitor:	1.0
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.995
20% Bioavailability (F20%):	0.157
30% Bioavailability (F30%):	0.1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	97.12574768066406%
Volume Distribution (VD):	0.847
Pgp-substrate:	5.533583641052246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.191
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.639
CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.5
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	2.541
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.978
Human Hepatotoxicity (H-HT):	0.998
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.743
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.237
Carcinogencity:	0.886
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC310633

Natural Product ID:	NPC310633
*Common Name:**	Nagelamide A
IUPAC Name:	N-[(3S)-3-[2-amino-4-[(E)-3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]prop-1-enyl]-1H-imidazol-5-yl]-3-(2-amino-1H-imidazol-5-yl)propyl]-4,5-dibromo-1H-pyrrole-2-carboxamide
Synonyms:
Standard InCHIKey:	QLDOUIZDLPGMQO-VWCDRPFISA-N
Standard InCHI:	InChI=1S/C22H22Br4N10O2/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/h1-2,6-9,32-33H,3-5H2,(H,29,37)(H,30,38)(H3,27,31,35)(H3,28,34,36)/b2-1+/t9-/m0/s1
SMILES:	C(=Cc1c([C@@H](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:	CHEMBL1162467
PubChem CID:	11411715
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	=	2.08	ug.mL-1	PMID[476973]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16.7	ug.mL-1	PMID[476973]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	33.3	ug.mL-1	PMID[476973]
NPT2	Others	Unspecified		IC50	=	48000.0	nM	PMID[476973]

☑ 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 NPC310633 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	1714
0.1-0.2	16388
0.2-0.3	17643
0.3-0.4	2778
0.4-0.5	2484
0.5-0.6	1351
0.6-0.7	266
0.7-0.8	47
0.8-0.85	3
0.85-0.9	11
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.994	High Similarity	NPC111566
0.982	High Similarity	NPC63571
0.9593	High Similarity	NPC19342
0.9326	High Similarity	NPC9635
0.9213	High Similarity	NPC19696
0.9213	High Similarity	NPC136957
0.9101	High Similarity	NPC174281
0.9101	High Similarity	NPC475286
0.9045	High Similarity	NPC476526
0.9045	High Similarity	NPC48117
0.9045	High Similarity	NPC329765
0.8976	High Similarity	NPC206148
0.875	High Similarity	NPC469716
0.8596	High Similarity	NPC476527
0.8505	High Similarity	NPC469717
0.8391	Intermediate Similarity	NPC54214
0.8314	Intermediate Similarity	NPC73687
0.8182	Intermediate Similarity	NPC476421
0.8182	Intermediate Similarity	NPC469976
0.8182	Intermediate Similarity	NPC28096
0.8182	Intermediate Similarity	NPC227489
0.8146	Intermediate Similarity	NPC136441
0.8135	Intermediate Similarity	NPC476524
0.8135	Intermediate Similarity	NPC476525
0.8103	Intermediate Similarity	NPC476418
0.8079	Intermediate Similarity	NPC226835
0.7967	Intermediate Similarity	NPC184932
0.7967	Intermediate Similarity	NPC472861
0.7833	Intermediate Similarity	NPC80528
0.779	Intermediate Similarity	NPC97106
0.7784	Intermediate Similarity	NPC469814
0.7765	Intermediate Similarity	NPC260041
0.7692	Intermediate Similarity	NPC37268
0.7644	Intermediate Similarity	NPC476414
0.7637	Intermediate Similarity	NPC271927
0.7592	Intermediate Similarity	NPC476413
0.759	Intermediate Similarity	NPC150592
0.753	Intermediate Similarity	NPC20021
0.7527	Intermediate Similarity	NPC314281
0.7527	Intermediate Similarity	NPC40530
0.7421	Intermediate Similarity	NPC112489
0.7421	Intermediate Similarity	NPC46022
0.7418	Intermediate Similarity	NPC474696
0.7374	Intermediate Similarity	NPC27296
0.7363	Intermediate Similarity	NPC2414
0.7358	Intermediate Similarity	NPC210123
0.7263	Intermediate Similarity	NPC474236
0.7213	Intermediate Similarity	NPC306160
0.7194	Intermediate Similarity	NPC188821
0.7194	Intermediate Similarity	NPC474180
0.7174	Intermediate Similarity	NPC474383
0.7173	Intermediate Similarity	NPC270834
0.7157	Intermediate Similarity	NPC46811
0.7143	Intermediate Similarity	NPC66642
0.7136	Intermediate Similarity	NPC474389
0.7067	Intermediate Similarity	NPC470703
0.7019	Intermediate Similarity	NPC470702
0.7019	Intermediate Similarity	NPC473218
0.7011	Intermediate Similarity	NPC473706
0.6961	Remote Similarity	NPC472260
0.6931	Remote Similarity	NPC477004
0.6923	Remote Similarity	NPC476423
0.6891	Remote Similarity	NPC16659
0.6875	Remote Similarity	NPC473380
0.6875	Remote Similarity	NPC240088
0.6839	Remote Similarity	NPC265710
0.6809	Remote Similarity	NPC233380
0.6791	Remote Similarity	NPC253687
0.6757	Remote Similarity	NPC474357
0.6742	Remote Similarity	NPC470323
0.6732	Remote Similarity	NPC13456
0.6732	Remote Similarity	NPC269203
0.6732	Remote Similarity	NPC77241
0.6732	Remote Similarity	NPC166209
0.6712	Remote Similarity	NPC267078
0.6712	Remote Similarity	NPC935
0.6698	Remote Similarity	NPC469715
0.6683	Remote Similarity	NPC153123
0.6683	Remote Similarity	NPC201266
0.6683	Remote Similarity	NPC475914
0.6683	Remote Similarity	NPC220797
0.6683	Remote Similarity	NPC268744
0.6683	Remote Similarity	NPC474318
0.6667	Remote Similarity	NPC133003
0.6648	Remote Similarity	NPC291517
0.6648	Remote Similarity	NPC23215
0.6636	Remote Similarity	NPC50562
0.6636	Remote Similarity	NPC474195
0.662	Remote Similarity	NPC475736
0.6616	Remote Similarity	NPC477003
0.6611	Remote Similarity	NPC58268
0.6611	Remote Similarity	NPC101130
0.6611	Remote Similarity	NPC114033
0.6611	Remote Similarity	NPC129412
0.6605	Remote Similarity	NPC67658
0.6591	Remote Similarity	NPC474196
0.6584	Remote Similarity	NPC476460
0.6577	Remote Similarity	NPC156003
0.6567	Remote Similarity	NPC473666
0.6566	Remote Similarity	NPC470205
0.6555	Remote Similarity	NPC317701
0.6541	Remote Similarity	NPC52110
0.6535	Remote Similarity	NPC324091
0.6517	Remote Similarity	NPC138596
0.6517	Remote Similarity	NPC195704
0.6517	Remote Similarity	NPC64661
0.6517	Remote Similarity	NPC292434
0.6517	Remote Similarity	NPC14448
0.6517	Remote Similarity	NPC98156
0.6517	Remote Similarity	NPC200397
0.6517	Remote Similarity	NPC167200
0.6513	Remote Similarity	NPC186068
0.6509	Remote Similarity	NPC116555
0.6492	Remote Similarity	NPC247987
0.6489	Remote Similarity	NPC142688
0.6482	Remote Similarity	NPC117027
0.6468	Remote Similarity	NPC17273
0.6468	Remote Similarity	NPC141612
0.6468	Remote Similarity	NPC135601
0.6464	Remote Similarity	NPC12831
0.6464	Remote Similarity	NPC59839
0.6464	Remote Similarity	NPC97230
0.6464	Remote Similarity	NPC3698
0.6464	Remote Similarity	NPC286529
0.6464	Remote Similarity	NPC302717
0.6464	Remote Similarity	NPC209281
0.6464	Remote Similarity	NPC48171
0.6464	Remote Similarity	NPC74928
0.6464	Remote Similarity	NPC205604
0.6464	Remote Similarity	NPC169308
0.6464	Remote Similarity	NPC77582
0.6464	Remote Similarity	NPC129753
0.6464	Remote Similarity	NPC244087
0.6462	Remote Similarity	NPC161861
0.645	Remote Similarity	NPC21429
0.6445	Remote Similarity	NPC473376
0.6442	Remote Similarity	NPC237414
0.6425	Remote Similarity	NPC243633
0.6425	Remote Similarity	NPC175150
0.6422	Remote Similarity	NPC267811
0.6418	Remote Similarity	NPC308931
0.6418	Remote Similarity	NPC99939
0.6383	Remote Similarity	NPC232798
0.6364	Remote Similarity	NPC168209
0.6359	Remote Similarity	NPC471943
0.6355	Remote Similarity	NPC473946
0.635	Remote Similarity	NPC307191
0.6349	Remote Similarity	NPC75135
0.6341	Remote Similarity	NPC243716
0.6327	Remote Similarity	NPC69843
0.6316	Remote Similarity	NPC171317
0.6313	Remote Similarity	NPC477413
0.6298	Remote Similarity	NPC472288
0.6298	Remote Similarity	NPC79356
0.6298	Remote Similarity	NPC102592
0.6294	Remote Similarity	NPC477611
0.6284	Remote Similarity	NPC282247
0.6281	Remote Similarity	NPC284775
0.628	Remote Similarity	NPC304203
0.6277	Remote Similarity	NPC471655
0.6267	Remote Similarity	NPC320968
0.6266	Remote Similarity	NPC17487
0.6266	Remote Similarity	NPC201831
0.6256	Remote Similarity	NPC474258
0.6239	Remote Similarity	NPC477107
0.6239	Remote Similarity	NPC477108
0.6239	Remote Similarity	NPC477109
0.6231	Remote Similarity	NPC151635
0.6219	Remote Similarity	NPC477042
0.6219	Remote Similarity	NPC91179
0.6219	Remote Similarity	NPC234403
0.6219	Remote Similarity	NPC79777
0.6219	Remote Similarity	NPC88110
0.621	Remote Similarity	NPC54744
0.6207	Remote Similarity	NPC110158
0.6202	Remote Similarity	NPC326422
0.6195	Remote Similarity	NPC17059
0.6178	Remote Similarity	NPC33229
0.6173	Remote Similarity	NPC109447
0.6165	Remote Similarity	NPC213629
0.6164	Remote Similarity	NPC471194
0.6164	Remote Similarity	NPC471193
0.6158	Remote Similarity	NPC109158
0.6154	Remote Similarity	NPC477167
0.6154	Remote Similarity	NPC477166
0.6154	Remote Similarity	NPC274981
0.6154	Remote Similarity	NPC473342
0.6154	Remote Similarity	NPC304187
0.615	Remote Similarity	NPC204141
0.6146	Remote Similarity	NPC94752
0.6127	Remote Similarity	NPC108011
0.6127	Remote Similarity	NPC228835
0.6122	Remote Similarity	NPC17751
0.6122	Remote Similarity	NPC280864
0.6119	Remote Similarity	NPC72956
0.6116	Remote Similarity	NPC272174
0.61	Remote Similarity	NPC469529
0.6094	Remote Similarity	NPC298288
0.6094	Remote Similarity	NPC477815
0.6091	Remote Similarity	NPC6865

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 NPC310633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	1145
0.2-0.3	1901
0.3-0.4	2153
0.4-0.5	1999
0.5-0.6	1308
0.6-0.7	245
0.7-0.8	16
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
0.7487	Intermediate Similarity	NPD7459	Phase 2
0.6869	Remote Similarity	NPD5686	Approved
0.6869	Remote Similarity	NPD5685	Approved
0.67	Remote Similarity	NPD2289	Phase 3
0.67	Remote Similarity	NPD2290	Phase 3
0.6667	Remote Similarity	NPD2442	Approved
0.6667	Remote Similarity	NPD2443	Approved
0.6635	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD5643	Phase 2
0.6479	Remote Similarity	NPD2408	Discontinued
0.6462	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD1506	Discontinued
0.6439	Remote Similarity	NPD460	Discontinued
0.6438	Remote Similarity	NPD5198	Approved
0.6438	Remote Similarity	NPD5199	Approved
0.6415	Remote Similarity	NPD2008	Discontinued
0.6402	Remote Similarity	NPD1600	Suspended
0.6394	Remote Similarity	NPD1982	Phase 1
0.6359	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2880	Discontinued
0.6341	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6579	Phase 2
0.633	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD2411	Approved
0.6305	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD2405	Phase 3
0.6262	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7656	Approved
0.6239	Remote Similarity	NPD7657	Approved
0.6205	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD8256	Approved
0.6199	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD8257	Approved
0.619	Remote Similarity	NPD5446	Phase 2
0.619	Remote Similarity	NPD1952	Discontinued
0.6182	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7970	Approved
0.6171	Remote Similarity	NPD6470	Phase 3
0.6169	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD3318	Approved
0.6158	Remote Similarity	NPD3319	Phase 1
0.6158	Remote Similarity	NPD3320	Approved
0.6157	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.615	Remote Similarity	NPD2367	Phase 2
0.615	Remote Similarity	NPD7817	Phase 1
0.615	Remote Similarity	NPD5017	Discontinued
0.6129	Remote Similarity	NPD6459	Phase 2
0.6124	Remote Similarity	NPD1031	Discontinued
0.6117	Remote Similarity	NPD3246	Discontinued
0.6111	Remote Similarity	NPD3967	Approved
0.6101	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5855	Phase 3
0.6095	Remote Similarity	NPD5853	Phase 3
0.6085	Remote Similarity	NPD465	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD3411	Phase 2
0.6083	Remote Similarity	NPD3410	Approved
0.6078	Remote Similarity	NPD6465	Phase 2
0.6077	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD3891	Phase 2
0.6075	Remote Similarity	NPD3890	Phase 2
0.6073	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD5854	Approved
0.6054	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD4863	Approved
0.6044	Remote Similarity	NPD6210	Phase 3
0.604	Remote Similarity	NPD7865	Approved
0.6038	Remote Similarity	NPD6664	Approved
0.6037	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6035	Remote Similarity	NPD7716	Approved
0.6035	Remote Similarity	NPD7717	Approved
0.6029	Remote Similarity	NPD1658	Discontinued
0.6029	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD3178	Discontinued
0.6027	Remote Similarity	NPD3968	Approved
0.6021	Remote Similarity	NPD971	Clinical (unspecified phase)
0.601	Remote Similarity	NPD439	Approved
0.601	Remote Similarity	NPD438	Approved
0.601	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5974	Approved
0.6	Remote Similarity	NPD5973	Phase 2
0.5979	Remote Similarity	NPD175	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD6268	Phase 1
0.5972	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD1096	Discontinued
0.5963	Remote Similarity	NPD6271	Approved
0.5962	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6165	Phase 2
0.5957	Remote Similarity	NPD6164	Phase 2
0.5956	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7406	Phase 2
0.5943	Remote Similarity	NPD7618	Phase 3
0.5943	Remote Similarity	NPD7619	Phase 3
0.5938	Remote Similarity	NPD3353	Approved
0.5933	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD3076	Approved
0.5931	Remote Similarity	NPD3078	Approved
0.5931	Remote Similarity	NPD3079	Approved
0.5931	Remote Similarity	NPD3077	Approved
0.593	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD272	Approved
0.5924	Remote Similarity	NPD4922	Phase 2
0.5924	Remote Similarity	NPD1896	Approved
0.5919	Remote Similarity	NPD2363	Discontinued
0.5917	Remote Similarity	NPD7209	Approved
0.5917	Remote Similarity	NPD7207	Approved
0.5917	Remote Similarity	NPD7208	Approved
0.5915	Remote Similarity	NPD7027	Phase 3
0.5913	Remote Similarity	NPD7026	Phase 2
0.5913	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5473	Discontinued
0.5902	Remote Similarity	NPD5962	Phase 2
0.5901	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4395	Phase 1
0.5885	Remote Similarity	NPD4988	Discontinued
0.5882	Remote Similarity	NPD3041	Approved
0.588	Remote Similarity	NPD8317	Phase 2
0.588	Remote Similarity	NPD8316	Phase 2
0.5879	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD2892	Phase 1
0.5873	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD1573	Approved
0.5871	Remote Similarity	NPD1575	Approved
0.5864	Remote Similarity	NPD8322	Phase 2
0.5862	Remote Similarity	NPD4883	Approved
0.5862	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD1003	Phase 2
0.5845	Remote Similarity	NPD5426	Phase 3
0.5845	Remote Similarity	NPD4299	Phase 1
0.5845	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5845	Remote Similarity	NPD8098	Approved
0.5845	Remote Similarity	NPD8169	Discontinued
0.5842	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6828	Phase 2
0.5841	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD1871	Approved
0.5837	Remote Similarity	NPD4940	Approved
0.5833	Remote Similarity	NPD4075	Phase 2
0.583	Remote Similarity	NPD3915	Approved
0.5826	Remote Similarity	NPD2879	Approved
0.5826	Remote Similarity	NPD2881	Approved
0.5825	Remote Similarity	NPD3927	Phase 2
0.5822	Remote Similarity	NPD2547	Discontinued
0.5822	Remote Similarity	NPD3460	Discontinued
0.5818	Remote Similarity	NPD5489	Phase 1
0.5818	Remote Similarity	NPD5491	Phase 3
0.5815	Remote Similarity	NPD1623	Approved
0.5811	Remote Similarity	NPD5510	Approved
0.581	Remote Similarity	NPD3961	Discontinued
0.5804	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD3917	Approved
0.5804	Remote Similarity	NPD8097	Phase 3
0.5804	Remote Similarity	NPD3918	Approved
0.5804	Remote Similarity	NPD8096	Phase 3
0.5802	Remote Similarity	NPD4558	Phase 2
0.5801	Remote Similarity	NPD5987	Approved
0.5801	Remote Similarity	NPD5986	Approved
0.5797	Remote Similarity	NPD1895	Discontinued
0.5794	Remote Similarity	NPD7887	Approved
0.5794	Remote Similarity	NPD7888	Approved
0.5787	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD7175	Phase 1
0.5782	Remote Similarity	NPD5016	Approved
0.5781	Remote Similarity	NPD6986	Phase 1
0.578	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.578	Remote Similarity	NPD7727	Phase 2
0.5779	Remote Similarity	NPD6771	Discontinued
0.5777	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD3833	Phase 3
0.5773	Remote Similarity	NPD3835	Phase 3
0.5773	Remote Similarity	NPD8114	Approved
0.5773	Remote Similarity	NPD5000	Phase 2
0.5773	Remote Similarity	NPD8115	Approved
0.5771	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.5767	Remote Similarity	NPD2222	Discontinued
0.5767	Remote Similarity	NPD9599	Approved
0.5767	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7232	Discontinued
0.5765	Remote Similarity	NPD2061	Approved
0.5764	Remote Similarity	NPD1996	Discontinued
0.5762	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD803	Phase 1
0.5761	Remote Similarity	NPD809	Discontinued
0.5758	Remote Similarity	NPD6753	Phase 1
0.5758	Remote Similarity	NPD6752	Phase 1
0.5758	Remote Similarity	NPD6849	Phase 2
0.5758	Remote Similarity	NPD6850	Phase 2
0.5756	Remote Similarity	NPD4385	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