NPASS Compound

Structure

NPC475735 OpenBabel07101719242D 26 27 0 0 0 0 0 0 0 0999 V2000 4.3301 -0.5000 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 3.4641 1.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 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 2.5981 -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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 9 1 0 0 0 0 2 15 1 0 0 0 0 3 4 1 0 0 0 0 3 9 1 0 0 0 0 4 21 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 22 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 21 2 3 0 0 0 17 25 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	547.86
Volume:	379.389
LogP:	3.924
LogD:	2.758
LogS:	-3.948
# Rotatable Bonds:	7
TPSA:	102.15
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.247
Synthetic Accessibility Score:	2.734
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.889
MDCK Permeability:	1.729743780742865e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.429
20% Bioavailability (F20%):	0.076
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	99.79024505615234%
Volume Distribution (VD):	0.282
Pgp-substrate:	1.1351374387741089%

ADMET: Metabolism

CYP1A2-inhibitor:	0.879
CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.941
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.933
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.93
CYP2D6-substrate:	0.487
CYP3A4-inhibitor:	0.611
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	0.744
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.268
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.586
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.286
Maximum Recommended Daily Dose:	0.362
Skin Sensitization:	0.855
Carcinogencity:	0.172
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC475735

Natural Product ID:	NPC475735
*Common Name:**	Hemibastadin 2
IUPAC Name:	(2Z)-N-[2-(3-bromo-4-hydroxyphenyl)ethyl]-3-(3,5-dibromo-4-hydroxyphenyl)-2-hydroxyiminopropanamide
Synonyms:	Hemibastadin 2
Standard InCHIKey:	QFAQAERRJYHBMR-HMAPJEAMSA-N
Standard InCHI:	InChI=1S/C17H15Br3N2O4/c18-11-5-9(1-2-15(11)23)3-4-21-17(25)14(22-26)8-10-6-12(19)16(24)13(20)7-10/h1-2,5-7,23-24,26H,3-4,8H2,(H,21,25)/b22-14-
SMILES:	C1=CC(=C(C=C1CCNC(=O)C(=NO)CC2=CC(=C(C(=C2)Br)O)Br)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513467
PubChem CID:	15338207
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0002320] Halophenols [CHEMONTID:0002764] Bromophenols [CHEMONTID:0002768] O-bromophenols

*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
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[2089117]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23249297]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Bismarck archipelago	n.a.	PMID[7623047]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[8904842]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988595]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	3.12	ug	PMID[475737]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.12	ug	PMID[475737]

☑ 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 NPC475735 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	276
0.1-0.2	3007
0.2-0.3	13470
0.3-0.4	6536
0.4-0.5	13673
0.5-0.6	4886
0.6-0.7	720
0.7-0.8	103
0.8-0.85	16
0.85-0.9	6
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9758	High Similarity	NPC474091
0.916	High Similarity	NPC309667
0.903	High Similarity	NPC474128
0.9008	High Similarity	NPC71888
0.9008	High Similarity	NPC120114
0.8923	High Similarity	NPC473724
0.8593	High Similarity	NPC474587
0.8593	High Similarity	NPC475132
0.855	High Similarity	NPC202776
0.8529	High Similarity	NPC475293
0.8521	High Similarity	NPC258222
0.8462	Intermediate Similarity	NPC475432
0.8433	Intermediate Similarity	NPC474753
0.8433	Intermediate Similarity	NPC166624
0.837	Intermediate Similarity	NPC163810
0.837	Intermediate Similarity	NPC184465
0.8288	Intermediate Similarity	NPC156311
0.8284	Intermediate Similarity	NPC99280
0.8231	Intermediate Similarity	NPC473738
0.8145	Intermediate Similarity	NPC473358
0.8129	Intermediate Similarity	NPC197045
0.8031	Intermediate Similarity	NPC115803
0.8014	Intermediate Similarity	NPC109968
0.7984	Intermediate Similarity	NPC311737
0.7984	Intermediate Similarity	NPC38458
0.7984	Intermediate Similarity	NPC471495
0.7953	Intermediate Similarity	NPC59387
0.792	Intermediate Similarity	NPC54543
0.7907	Intermediate Similarity	NPC82963
0.7872	Intermediate Similarity	NPC213471
0.7847	Intermediate Similarity	NPC78530
0.784	Intermediate Similarity	NPC153690
0.784	Intermediate Similarity	NPC24101
0.784	Intermediate Similarity	NPC96224
0.7838	Intermediate Similarity	NPC47672
0.7785	Intermediate Similarity	NPC469979
0.7763	Intermediate Similarity	NPC123848
0.7736	Intermediate Similarity	NPC126128
0.7736	Intermediate Similarity	NPC298981
0.7736	Intermediate Similarity	NPC207819
0.7736	Intermediate Similarity	NPC473462
0.7736	Intermediate Similarity	NPC110454
0.7724	Intermediate Similarity	NPC135349
0.7692	Intermediate Similarity	NPC317254
0.7682	Intermediate Similarity	NPC233926
0.768	Intermediate Similarity	NPC231705
0.7673	Intermediate Similarity	NPC226001
0.766	Intermediate Similarity	NPC303993
0.7638	Intermediate Similarity	NPC258056
0.7635	Intermediate Similarity	NPC20755
0.7615	Intermediate Similarity	NPC118202
0.761	Intermediate Similarity	NPC225130
0.7594	Intermediate Similarity	NPC268572
0.7593	Intermediate Similarity	NPC214188
0.7593	Intermediate Similarity	NPC74618
0.7593	Intermediate Similarity	NPC301941
0.7581	Intermediate Similarity	NPC178902
0.7578	Intermediate Similarity	NPC474149
0.7518	Intermediate Similarity	NPC213414
0.7483	Intermediate Similarity	NPC470472
0.7481	Intermediate Similarity	NPC94217
0.748	Intermediate Similarity	NPC142297
0.7469	Intermediate Similarity	NPC290534
0.7467	Intermediate Similarity	NPC76412
0.7463	Intermediate Similarity	NPC283760
0.7423	Intermediate Similarity	NPC475396
0.741	Intermediate Similarity	NPC144823
0.7405	Intermediate Similarity	NPC471488
0.7388	Intermediate Similarity	NPC122009
0.7376	Intermediate Similarity	NPC474087
0.7372	Intermediate Similarity	NPC296202
0.7365	Intermediate Similarity	NPC82741
0.7365	Intermediate Similarity	NPC473409
0.7365	Intermediate Similarity	NPC141405
0.7361	Intermediate Similarity	NPC470471
0.7353	Intermediate Similarity	NPC471486
0.7333	Intermediate Similarity	NPC38483
0.7319	Intermediate Similarity	NPC105999
0.7313	Intermediate Similarity	NPC283468
0.7308	Intermediate Similarity	NPC471487
0.7305	Intermediate Similarity	NPC471591
0.7305	Intermediate Similarity	NPC325651
0.7305	Intermediate Similarity	NPC473892
0.7305	Intermediate Similarity	NPC475658
0.7299	Intermediate Similarity	NPC7830
0.7273	Intermediate Similarity	NPC33244
0.726	Intermediate Similarity	NPC470470
0.7254	Intermediate Similarity	NPC478071
0.7246	Intermediate Similarity	NPC49172
0.7231	Intermediate Similarity	NPC473372
0.7226	Intermediate Similarity	NPC284078
0.7206	Intermediate Similarity	NPC43275
0.7203	Intermediate Similarity	NPC326966
0.7203	Intermediate Similarity	NPC11449
0.716	Intermediate Similarity	NPC470951
0.7153	Intermediate Similarity	NPC244866
0.7151	Intermediate Similarity	NPC469721
0.7143	Intermediate Similarity	NPC309808
0.712	Intermediate Similarity	NPC107619
0.7103	Intermediate Similarity	NPC243404
0.7103	Intermediate Similarity	NPC267237
0.7091	Intermediate Similarity	NPC475615
0.709	Intermediate Similarity	NPC142599
0.708	Intermediate Similarity	NPC319950
0.7069	Intermediate Similarity	NPC469731
0.7066	Intermediate Similarity	NPC475283
0.7066	Intermediate Similarity	NPC152205
0.705	Intermediate Similarity	NPC474862
0.705	Intermediate Similarity	NPC27581
0.7037	Intermediate Similarity	NPC37302
0.7027	Intermediate Similarity	NPC474673
0.7008	Intermediate Similarity	NPC155847
0.7008	Intermediate Similarity	NPC289381
0.6993	Remote Similarity	NPC122359
0.6993	Remote Similarity	NPC159987
0.6993	Remote Similarity	NPC78061
0.6972	Remote Similarity	NPC110131
0.6972	Remote Similarity	NPC220311
0.6966	Remote Similarity	NPC114102
0.6966	Remote Similarity	NPC45191
0.6944	Remote Similarity	NPC271808
0.6933	Remote Similarity	NPC168861
0.6929	Remote Similarity	NPC125732
0.6913	Remote Similarity	NPC214988
0.6906	Remote Similarity	NPC180207
0.6906	Remote Similarity	NPC263835
0.6905	Remote Similarity	NPC33168
0.6901	Remote Similarity	NPC272463
0.6901	Remote Similarity	NPC95733
0.6901	Remote Similarity	NPC62101
0.6883	Remote Similarity	NPC296085
0.688	Remote Similarity	NPC151715
0.6875	Remote Similarity	NPC251571
0.6875	Remote Similarity	NPC13004
0.6867	Remote Similarity	NPC471236
0.6867	Remote Similarity	NPC476989
0.6867	Remote Similarity	NPC197766
0.6855	Remote Similarity	NPC45040
0.6853	Remote Similarity	NPC29477
0.6849	Remote Similarity	NPC275538
0.6831	Remote Similarity	NPC211218
0.6828	Remote Similarity	NPC478147
0.6825	Remote Similarity	NPC26244
0.6824	Remote Similarity	NPC471328
0.6816	Remote Similarity	NPC156055
0.6803	Remote Similarity	NPC214869
0.6794	Remote Similarity	NPC211551
0.6781	Remote Similarity	NPC474614
0.6781	Remote Similarity	NPC195749
0.6781	Remote Similarity	NPC52029
0.6781	Remote Similarity	NPC35961
0.6779	Remote Similarity	NPC6913
0.6779	Remote Similarity	NPC6570
0.6779	Remote Similarity	NPC64205
0.6774	Remote Similarity	NPC71629
0.6772	Remote Similarity	NPC473388
0.6761	Remote Similarity	NPC471314
0.6761	Remote Similarity	NPC471315
0.6759	Remote Similarity	NPC296712
0.6759	Remote Similarity	NPC477839
0.6757	Remote Similarity	NPC300678
0.6746	Remote Similarity	NPC128062
0.6738	Remote Similarity	NPC83279
0.6716	Remote Similarity	NPC290566
0.6716	Remote Similarity	NPC145638
0.6713	Remote Similarity	NPC307020
0.6712	Remote Similarity	NPC155838
0.6694	Remote Similarity	NPC172128
0.6693	Remote Similarity	NPC274678
0.6692	Remote Similarity	NPC91461
0.6692	Remote Similarity	NPC40258
0.6692	Remote Similarity	NPC7686
0.669	Remote Similarity	NPC136543
0.669	Remote Similarity	NPC142577
0.669	Remote Similarity	NPC301713
0.6689	Remote Similarity	NPC471237
0.6689	Remote Similarity	NPC177967
0.6667	Remote Similarity	NPC246591
0.6667	Remote Similarity	NPC303370
0.6667	Remote Similarity	NPC41801
0.6667	Remote Similarity	NPC216468
0.6667	Remote Similarity	NPC51333
0.6667	Remote Similarity	NPC252817
0.6667	Remote Similarity	NPC132078
0.6667	Remote Similarity	NPC78119
0.6647	Remote Similarity	NPC259071
0.6647	Remote Similarity	NPC77435
0.6645	Remote Similarity	NPC16188
0.6644	Remote Similarity	NPC186898
0.6642	Remote Similarity	NPC76400
0.6641	Remote Similarity	NPC216520
0.6641	Remote Similarity	NPC132271
0.6641	Remote Similarity	NPC82664
0.6641	Remote Similarity	NPC292730
0.6641	Remote Similarity	NPC68055
0.6622	Remote Similarity	NPC257390
0.6621	Remote Similarity	NPC476249
0.6618	Remote Similarity	NPC163674
0.6618	Remote Similarity	NPC227553
0.6618	Remote Similarity	NPC166837

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 NPC475735 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	853
0.2-0.3	1109
0.3-0.4	2429
0.4-0.5	3225
0.5-0.6	1210
0.6-0.7	148
0.7-0.8	6
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
0.7622	Intermediate Similarity	NPD1169	Approved
0.75	Intermediate Similarity	NPD9718	Approved
0.741	Intermediate Similarity	NPD7451	Discontinued
0.7353	Intermediate Similarity	NPD3421	Phase 3
0.7194	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1223	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2234	Approved
0.7015	Intermediate Similarity	NPD2228	Approved
0.7015	Intermediate Similarity	NPD2229	Approved
0.7	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD9608	Approved
0.6977	Remote Similarity	NPD9610	Approved
0.6913	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3136	Phase 2
0.688	Remote Similarity	NPD2933	Approved
0.688	Remote Similarity	NPD2934	Approved
0.6867	Remote Similarity	NPD7450	Phase 2
0.6825	Remote Similarity	NPD2859	Approved
0.6825	Remote Similarity	NPD2860	Approved
0.6803	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2372	Approved
0.6763	Remote Similarity	NPD5303	Approved
0.6763	Remote Similarity	NPD5304	Approved
0.6761	Remote Similarity	NPD2562	Approved
0.6761	Remote Similarity	NPD2561	Approved
0.6716	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD4093	Discontinued
0.6713	Remote Similarity	NPD4659	Approved
0.6711	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2183	Approved
0.6688	Remote Similarity	NPD2184	Approved
0.6667	Remote Similarity	NPD5310	Approved
0.6667	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3020	Approved
0.6667	Remote Similarity	NPD5311	Approved
0.6644	Remote Similarity	NPD6346	Approved
0.6643	Remote Similarity	NPD1759	Phase 1
0.6623	Remote Similarity	NPD3552	Approved
0.6623	Remote Similarity	NPD3554	Approved
0.6623	Remote Similarity	NPD3555	Approved
0.6623	Remote Similarity	NPD3553	Approved
0.6621	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3053	Approved
0.6621	Remote Similarity	NPD4103	Phase 2
0.6621	Remote Similarity	NPD3055	Approved
0.6597	Remote Similarity	NPD1669	Approved
0.6593	Remote Similarity	NPD1792	Phase 2
0.6581	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD318	Approved
0.6571	Remote Similarity	NPD1758	Phase 1
0.6571	Remote Similarity	NPD317	Approved
0.6569	Remote Similarity	NPD9377	Approved
0.6569	Remote Similarity	NPD9379	Approved
0.6556	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.65	Remote Similarity	NPD9568	Approved
0.6494	Remote Similarity	NPD7978	Discontinued
0.6493	Remote Similarity	NPD1444	Approved
0.6493	Remote Similarity	NPD1445	Approved
0.6478	Remote Similarity	NPD7303	Discontinued
0.6474	Remote Similarity	NPD2802	Phase 3
0.6467	Remote Similarity	NPD7477	Discontinued
0.6467	Remote Similarity	NPD2674	Phase 3
0.6466	Remote Similarity	NPD9244	Approved
0.6454	Remote Similarity	NPD16	Approved
0.6454	Remote Similarity	NPD856	Approved
0.6452	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD821	Approved
0.6434	Remote Similarity	NPD2668	Approved
0.6434	Remote Similarity	NPD2667	Approved
0.6423	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1980	Approved
0.6389	Remote Similarity	NPD1983	Approved
0.6389	Remote Similarity	NPD1981	Approved
0.6369	Remote Similarity	NPD3400	Discontinued
0.6364	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6407	Approved
0.6358	Remote Similarity	NPD6405	Approved
0.6357	Remote Similarity	NPD9614	Approved
0.6357	Remote Similarity	NPD9618	Approved
0.635	Remote Similarity	NPD3021	Approved
0.635	Remote Similarity	NPD3022	Approved
0.634	Remote Similarity	NPD2568	Approved
0.634	Remote Similarity	NPD5314	Approved
0.6336	Remote Similarity	NPD9273	Approved
0.6333	Remote Similarity	NPD5156	Approved
0.6333	Remote Similarity	NPD5155	Approved
0.6328	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD1751	Approved
0.6316	Remote Similarity	NPD3059	Approved
0.6316	Remote Similarity	NPD3061	Approved
0.6316	Remote Similarity	NPD3062	Approved
0.6312	Remote Similarity	NPD255	Approved
0.6312	Remote Similarity	NPD256	Approved
0.6309	Remote Similarity	NPD3636	Approved
0.6309	Remote Similarity	NPD3635	Approved
0.6309	Remote Similarity	NPD3637	Approved
0.6291	Remote Similarity	NPD3145	Approved
0.6291	Remote Similarity	NPD3144	Approved
0.6291	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.629	Remote Similarity	NPD111	Approved
0.6276	Remote Similarity	NPD3143	Discontinued
0.6268	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD2605	Approved
0.6267	Remote Similarity	NPD3595	Approved
0.6267	Remote Similarity	NPD2606	Approved
0.6267	Remote Similarity	NPD3594	Approved
0.6259	Remote Similarity	NPD6583	Phase 3
0.6259	Remote Similarity	NPD6582	Phase 2
0.625	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2195	Approved
0.6242	Remote Similarity	NPD7495	Discontinued
0.6242	Remote Similarity	NPD8019	Approved
0.6242	Remote Similarity	NPD2194	Approved
0.6241	Remote Similarity	NPD475	Phase 2
0.6241	Remote Similarity	NPD1791	Approved
0.6241	Remote Similarity	NPD1793	Approved
0.6241	Remote Similarity	NPD3028	Approved
0.6241	Remote Similarity	NPD1242	Phase 1
0.6234	Remote Similarity	NPD3054	Approved
0.6234	Remote Similarity	NPD3052	Approved
0.6233	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD9615	Approved
0.6224	Remote Similarity	NPD9613	Approved
0.6224	Remote Similarity	NPD9616	Approved
0.6222	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD9381	Approved
0.6207	Remote Similarity	NPD9384	Approved
0.6203	Remote Similarity	NPD2459	Approved
0.6203	Remote Similarity	NPD2458	Approved
0.6203	Remote Similarity	NPD2460	Phase 3
0.62	Remote Similarity	NPD4993	Discontinued
0.619	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD7554	Discontinued
0.6181	Remote Similarity	NPD316	Approved
0.6174	Remote Similarity	NPD1129	Approved
0.6174	Remote Similarity	NPD1133	Approved
0.6174	Remote Similarity	NPD1135	Approved
0.6174	Remote Similarity	NPD1131	Approved
0.6174	Remote Similarity	NPD1134	Approved
0.6164	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD6331	Phase 2
0.6149	Remote Similarity	NPD9622	Approved
0.6149	Remote Similarity	NPD3359	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4656	Approved
0.6148	Remote Similarity	NPD4658	Approved
0.6144	Remote Similarity	NPD839	Approved
0.6144	Remote Similarity	NPD840	Approved
0.614	Remote Similarity	NPD4010	Discontinued
0.614	Remote Similarity	NPD1161	Approved
0.6135	Remote Similarity	NPD7523	Phase 3
0.6135	Remote Similarity	NPD7131	Phase 3
0.6133	Remote Similarity	NPD6584	Phase 3
0.6118	Remote Similarity	NPD1024	Discontinued
0.6111	Remote Similarity	NPD4123	Phase 3
0.6111	Remote Similarity	NPD3985	Discontinued
0.6111	Remote Similarity	NPD2874	Phase 2
0.6111	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD1555	Discontinued
0.6099	Remote Similarity	NPD2497	Approved
0.6099	Remote Similarity	NPD2496	Approved
0.6096	Remote Similarity	NPD2286	Discontinued
0.6093	Remote Similarity	NPD9569	Approved
0.6087	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD7438	Suspended
0.6084	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD6072	Discontinued
0.6081	Remote Similarity	NPD2232	Approved
0.6081	Remote Similarity	NPD2230	Approved
0.6081	Remote Similarity	NPD2233	Approved
0.6078	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD6690	Approved
0.6074	Remote Similarity	NPD4817	Approved
0.6074	Remote Similarity	NPD940	Approved
0.6074	Remote Similarity	NPD846	Approved
0.6074	Remote Similarity	NPD4818	Approved
0.6071	Remote Similarity	NPD2296	Approved
0.6067	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD4108	Discontinued
0.604	Remote Similarity	NPD3685	Discontinued
0.6038	Remote Similarity	NPD7153	Discontinued
0.6029	Remote Similarity	NPD3682	Approved
0.6029	Remote Similarity	NPD4229	Approved
0.6029	Remote Similarity	NPD4231	Approved
0.6029	Remote Similarity	NPD1542	Approved
0.6029	Remote Similarity	NPD3680	Approved
0.6026	Remote Similarity	NPD2157	Approved
0.6026	Remote Similarity	NPD9620	Approved
0.6026	Remote Similarity	NPD9621	Approved
0.6026	Remote Similarity	NPD9619	Approved
0.6013	Remote Similarity	NPD1538	Phase 1
0.6013	Remote Similarity	NPD1519	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