NPASS Compound

Structure

NPC474091 OpenBabel07101718222D 25 26 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 -0.8660 -1.5000 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 0.0000 -1.0000 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 -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 -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 -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 3 2 0 0 0 0 1 10 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 20 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 21 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 20 2 3 0 0 0 17 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	469.95
Volume:	360.105
LogP:	3.425
LogD:	2.84
LogS:	-3.86
# Rotatable Bonds:	7
TPSA:	102.15
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.294
Synthetic Accessibility Score:	2.608
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.786
MDCK Permeability:	1.7491187463747337e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.111
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	98.8958969116211%
Volume Distribution (VD):	0.371
Pgp-substrate:	0.8723015785217285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.896
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.931
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.928
CYP2D6-substrate:	0.699
CYP3A4-inhibitor:	0.601
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	1.037
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.247
Drug-inuced Liver Injury (DILI):	0.703
AMES Toxicity:	0.171
Rat Oral Acute Toxicity:	0.272
Maximum Recommended Daily Dose:	0.176
Skin Sensitization:	0.835
Carcinogencity:	0.298
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC474091

Natural Product ID:	NPC474091
*Common Name:**	Hemibastadin 1
IUPAC Name:	(2Z)-3-(3-bromo-4-hydroxyphenyl)-N-[2-(3-bromo-4-hydroxyphenyl)ethyl]-2-hydroxyiminopropanamide
Synonyms:	Hemibastadin 1
Standard InCHIKey:	XEBJFQMMTPIWKF-STZFKDTASA-N
Standard InCHI:	InChI=1S/C17H16Br2N2O4/c18-12-7-10(1-3-15(12)22)5-6-20-17(24)14(21-25)9-11-2-4-16(23)13(19)8-11/h1-4,7-8,22-23,25H,5-6,9H2,(H,20,24)/b21-14-
SMILES:	O/N=C(C(=NCCc1ccc(c(c1)Br)O)O)/Cc1ccc(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460971
PubChem CID:	15338206
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	3
Others	1

Activity Type	# Activity
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	12.5	ug	PMID[514296]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	50.0	ug	PMID[514296]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.56	ug	PMID[514296]
NPT2	Others	Unspecified		Inhibition	=	5.0	%	PMID[514297]

☑ 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 NPC474091 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	269
0.1-0.2	2887
0.2-0.3	13252
0.3-0.4	6325
0.4-0.5	13623
0.5-0.6	5373
0.6-0.7	829
0.7-0.8	110
0.8-0.85	14
0.85-0.9	9
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9758	High Similarity	NPC475735
0.9242	High Similarity	NPC474128
0.9225	High Similarity	NPC120114
0.9225	High Similarity	NPC71888
0.9141	High Similarity	NPC473724
0.9084	High Similarity	NPC309667
0.8797	High Similarity	NPC474587
0.8797	High Similarity	NPC475132
0.8731	High Similarity	NPC475293
0.8652	High Similarity	NPC475432
0.8615	High Similarity	NPC202776
0.8571	High Similarity	NPC163810
0.8496	Intermediate Similarity	NPC166624
0.8496	Intermediate Similarity	NPC474753
0.8451	Intermediate Similarity	NPC258222
0.8433	Intermediate Similarity	NPC184465
0.8414	Intermediate Similarity	NPC473738
0.8321	Intermediate Similarity	NPC197045
0.8219	Intermediate Similarity	NPC156311
0.8189	Intermediate Similarity	NPC311737
0.8189	Intermediate Similarity	NPC38458
0.811	Intermediate Similarity	NPC82963
0.8074	Intermediate Similarity	NPC99280
0.8049	Intermediate Similarity	NPC96224
0.8049	Intermediate Similarity	NPC24101
0.8049	Intermediate Similarity	NPC471495
0.8016	Intermediate Similarity	NPC59387
0.7945	Intermediate Similarity	NPC109968
0.7933	Intermediate Similarity	NPC123848
0.792	Intermediate Similarity	NPC473358
0.7903	Intermediate Similarity	NPC153690
0.7891	Intermediate Similarity	NPC317254
0.7886	Intermediate Similarity	NPC231705
0.7842	Intermediate Similarity	NPC303993
0.784	Intermediate Similarity	NPC258056
0.7812	Intermediate Similarity	NPC115803
0.7812	Intermediate Similarity	NPC118202
0.7808	Intermediate Similarity	NPC20755
0.7801	Intermediate Similarity	NPC213471
0.7786	Intermediate Similarity	NPC268572
0.7778	Intermediate Similarity	NPC78530
0.7778	Intermediate Similarity	NPC474149
0.7771	Intermediate Similarity	NPC225130
0.777	Intermediate Similarity	NPC47672
0.7722	Intermediate Similarity	NPC469979
0.7698	Intermediate Similarity	NPC54543
0.768	Intermediate Similarity	NPC142297
0.7673	Intermediate Similarity	NPC473462
0.7673	Intermediate Similarity	NPC298981
0.7673	Intermediate Similarity	NPC110454
0.7673	Intermediate Similarity	NPC207819
0.7673	Intermediate Similarity	NPC126128
0.7655	Intermediate Similarity	NPC135349
0.7652	Intermediate Similarity	NPC283760
0.7642	Intermediate Similarity	NPC178902
0.7625	Intermediate Similarity	NPC290534
0.7616	Intermediate Similarity	NPC233926
0.761	Intermediate Similarity	NPC226001
0.7576	Intermediate Similarity	NPC122009
0.7531	Intermediate Similarity	NPC301941
0.7531	Intermediate Similarity	NPC74618
0.7531	Intermediate Similarity	NPC214188
0.75	Intermediate Similarity	NPC283468
0.7482	Intermediate Similarity	NPC325651
0.7429	Intermediate Similarity	NPC474087
0.7426	Intermediate Similarity	NPC296202
0.7415	Intermediate Similarity	NPC470472
0.74	Intermediate Similarity	NPC76412
0.7394	Intermediate Similarity	NPC49172
0.7388	Intermediate Similarity	NPC38483
0.7388	Intermediate Similarity	NPC43275
0.7376	Intermediate Similarity	NPC326966
0.7364	Intermediate Similarity	NPC471487
0.7362	Intermediate Similarity	NPC475396
0.7353	Intermediate Similarity	NPC7830
0.7349	Intermediate Similarity	NPC144823
0.7324	Intermediate Similarity	NPC244866
0.7319	Intermediate Similarity	NPC213414
0.7305	Intermediate Similarity	NPC473409
0.7305	Intermediate Similarity	NPC141405
0.7305	Intermediate Similarity	NPC82741
0.7305	Intermediate Similarity	NPC470951
0.7292	Intermediate Similarity	NPC470471
0.7287	Intermediate Similarity	NPC473372
0.7279	Intermediate Similarity	NPC284078
0.7273	Intermediate Similarity	NPC267237
0.7273	Intermediate Similarity	NPC94217
0.7246	Intermediate Similarity	NPC475658
0.7246	Intermediate Similarity	NPC471591
0.7246	Intermediate Similarity	NPC473892
0.7239	Intermediate Similarity	NPC475615
0.7226	Intermediate Similarity	NPC474862
0.7218	Intermediate Similarity	NPC37302
0.7212	Intermediate Similarity	NPC152205
0.7212	Intermediate Similarity	NPC475283
0.7197	Intermediate Similarity	NPC471488
0.7197	Intermediate Similarity	NPC309808
0.7192	Intermediate Similarity	NPC470470
0.7177	Intermediate Similarity	NPC107619
0.7153	Intermediate Similarity	NPC471486
0.7153	Intermediate Similarity	NPC243404
0.7143	Intermediate Similarity	NPC142599
0.7133	Intermediate Similarity	NPC45191
0.7133	Intermediate Similarity	NPC114102
0.7132	Intermediate Similarity	NPC319950
0.7122	Intermediate Similarity	NPC105999
0.7113	Intermediate Similarity	NPC271808
0.7101	Intermediate Similarity	NPC27581
0.7097	Intermediate Similarity	NPC33168
0.7095	Intermediate Similarity	NPC168861
0.7093	Intermediate Similarity	NPC469721
0.708	Intermediate Similarity	NPC263835
0.7075	Intermediate Similarity	NPC214988
0.7073	Intermediate Similarity	NPC151715
0.7071	Intermediate Similarity	NPC95733
0.7071	Intermediate Similarity	NPC62101
0.7068	Intermediate Similarity	NPC33244
0.7063	Intermediate Similarity	NPC478071
0.7063	Intermediate Similarity	NPC155847
0.7063	Intermediate Similarity	NPC289381
0.7042	Intermediate Similarity	NPC251571
0.7042	Intermediate Similarity	NPC78061
0.7042	Intermediate Similarity	NPC159987
0.7042	Intermediate Similarity	NPC122359
0.7027	Intermediate Similarity	NPC476989
0.7021	Intermediate Similarity	NPC220311
0.7021	Intermediate Similarity	NPC29477
0.7016	Intermediate Similarity	NPC26244
0.7014	Intermediate Similarity	NPC275538
0.7014	Intermediate Similarity	NPC11449
0.7011	Intermediate Similarity	NPC469731
0.7	Intermediate Similarity	NPC211218
0.6993	Remote Similarity	NPC478147
0.6984	Remote Similarity	NPC125732
0.6977	Remote Similarity	NPC211551
0.6966	Remote Similarity	NPC214869
0.696	Remote Similarity	NPC473388
0.6959	Remote Similarity	NPC474673
0.6944	Remote Similarity	NPC52029
0.6944	Remote Similarity	NPC35961
0.6944	Remote Similarity	NPC195749
0.6939	Remote Similarity	NPC6570
0.6939	Remote Similarity	NPC64205
0.6939	Remote Similarity	NPC6913
0.6929	Remote Similarity	NPC471315
0.6929	Remote Similarity	NPC471314
0.6923	Remote Similarity	NPC296712
0.6923	Remote Similarity	NPC477839
0.6911	Remote Similarity	NPC45040
0.6906	Remote Similarity	NPC83279
0.6901	Remote Similarity	NPC110131
0.6885	Remote Similarity	NPC172128
0.6879	Remote Similarity	NPC307020
0.6875	Remote Similarity	NPC40258
0.6875	Remote Similarity	NPC91461
0.6875	Remote Similarity	NPC155838
0.6875	Remote Similarity	NPC7686
0.6857	Remote Similarity	NPC142577
0.6853	Remote Similarity	NPC301713
0.685	Remote Similarity	NPC216468
0.685	Remote Similarity	NPC51333
0.685	Remote Similarity	NPC78119
0.685	Remote Similarity	NPC132078
0.6838	Remote Similarity	NPC303370
0.6835	Remote Similarity	NPC252817
0.6835	Remote Similarity	NPC41801
0.6831	Remote Similarity	NPC272463
0.6828	Remote Similarity	NPC474614
0.6825	Remote Similarity	NPC82664
0.6825	Remote Similarity	NPC216520
0.6825	Remote Similarity	NPC292730
0.6825	Remote Similarity	NPC132271
0.6818	Remote Similarity	NPC296085
0.6815	Remote Similarity	NPC76400
0.6806	Remote Similarity	NPC186898
0.6803	Remote Similarity	NPC300678
0.68	Remote Similarity	NPC128062
0.6797	Remote Similarity	NPC213730
0.6797	Remote Similarity	NPC16188
0.6791	Remote Similarity	NPC166837
0.6783	Remote Similarity	NPC476249
0.6781	Remote Similarity	NPC257390
0.6767	Remote Similarity	NPC290566
0.6767	Remote Similarity	NPC145638
0.676	Remote Similarity	NPC156055
0.6755	Remote Similarity	NPC212850
0.6755	Remote Similarity	NPC83289
0.6755	Remote Similarity	NPC189724
0.6748	Remote Similarity	NPC280347
0.6748	Remote Similarity	NPC177420
0.6746	Remote Similarity	NPC274678
0.6744	Remote Similarity	NPC96275
0.6743	Remote Similarity	NPC65714
0.6738	Remote Similarity	NPC136543
0.6736	Remote Similarity	NPC476353
0.6735	Remote Similarity	NPC328070
0.6735	Remote Similarity	NPC471953
0.6733	Remote Similarity	NPC41473
0.6733	Remote Similarity	NPC312770
0.6733	Remote Similarity	NPC14600

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 NPC474091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	835
0.2-0.3	1098
0.3-0.4	2322
0.4-0.5	3273
0.5-0.6	1259
0.6-0.7	191
0.7-0.8	8
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
0.7591	Intermediate Similarity	NPD7451	Discontinued
0.7537	Intermediate Similarity	NPD3421	Phase 3
0.7431	Intermediate Similarity	NPD1169	Approved
0.7372	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD9718	Approved
0.7197	Intermediate Similarity	NPD2234	Approved
0.7197	Intermediate Similarity	NPD2228	Approved
0.7197	Intermediate Similarity	NPD2229	Approved
0.7183	Intermediate Similarity	NPD1223	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2934	Approved
0.7073	Intermediate Similarity	NPD2933	Approved
0.7063	Intermediate Similarity	NPD3136	Phase 2
0.705	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD9610	Approved
0.7031	Intermediate Similarity	NPD9608	Approved
0.7027	Intermediate Similarity	NPD7450	Phase 2
0.7016	Intermediate Similarity	NPD2859	Approved
0.7016	Intermediate Similarity	NPD2860	Approved
0.6966	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2372	Approved
0.6934	Remote Similarity	NPD5304	Approved
0.6934	Remote Similarity	NPD5303	Approved
0.6929	Remote Similarity	NPD2561	Approved
0.6929	Remote Similarity	NPD2562	Approved
0.6884	Remote Similarity	NPD4093	Discontinued
0.6879	Remote Similarity	NPD4659	Approved
0.6867	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3020	Approved
0.6839	Remote Similarity	NPD2184	Approved
0.6839	Remote Similarity	NPD2183	Approved
0.6835	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5311	Approved
0.6831	Remote Similarity	NPD5310	Approved
0.6812	Remote Similarity	NPD1759	Phase 1
0.6803	Remote Similarity	NPD6346	Approved
0.6783	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3053	Approved
0.6783	Remote Similarity	NPD3055	Approved
0.6783	Remote Similarity	NPD4103	Phase 2
0.6779	Remote Similarity	NPD3553	Approved
0.6779	Remote Similarity	NPD3552	Approved
0.6779	Remote Similarity	NPD3555	Approved
0.6779	Remote Similarity	NPD3554	Approved
0.6767	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1792	Phase 2
0.6761	Remote Similarity	NPD1669	Approved
0.6739	Remote Similarity	NPD1758	Phase 1
0.6732	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1445	Approved
0.6667	Remote Similarity	NPD1444	Approved
0.6645	Remote Similarity	NPD7978	Discontinued
0.6624	Remote Similarity	NPD7303	Discontinued
0.6622	Remote Similarity	NPD7477	Discontinued
0.6622	Remote Similarity	NPD2674	Phase 3
0.6619	Remote Similarity	NPD317	Approved
0.6619	Remote Similarity	NPD856	Approved
0.6619	Remote Similarity	NPD318	Approved
0.6619	Remote Similarity	NPD16	Approved
0.6618	Remote Similarity	NPD9379	Approved
0.6618	Remote Similarity	NPD821	Approved
0.6618	Remote Similarity	NPD9377	Approved
0.6601	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2667	Approved
0.6596	Remote Similarity	NPD2668	Approved
0.6549	Remote Similarity	NPD1980	Approved
0.6549	Remote Similarity	NPD1983	Approved
0.6549	Remote Similarity	NPD1981	Approved
0.6547	Remote Similarity	NPD9568	Approved
0.6538	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3021	Approved
0.6519	Remote Similarity	NPD3022	Approved
0.6516	Remote Similarity	NPD3400	Discontinued
0.651	Remote Similarity	NPD6407	Approved
0.651	Remote Similarity	NPD6405	Approved
0.649	Remote Similarity	NPD2568	Approved
0.649	Remote Similarity	NPD5314	Approved
0.6486	Remote Similarity	NPD5156	Approved
0.6486	Remote Similarity	NPD5155	Approved
0.6479	Remote Similarity	NPD1751	Approved
0.6471	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3061	Approved
0.6467	Remote Similarity	NPD3062	Approved
0.6467	Remote Similarity	NPD3059	Approved
0.6463	Remote Similarity	NPD3636	Approved
0.6463	Remote Similarity	NPD3635	Approved
0.6463	Remote Similarity	NPD3637	Approved
0.6443	Remote Similarity	NPD3145	Approved
0.6443	Remote Similarity	NPD3144	Approved
0.6443	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD3143	Discontinued
0.6429	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD2605	Approved
0.6419	Remote Similarity	NPD3595	Approved
0.6419	Remote Similarity	NPD2606	Approved
0.6419	Remote Similarity	NPD3594	Approved
0.6416	Remote Similarity	NPD2802	Phase 3
0.6414	Remote Similarity	NPD6583	Phase 3
0.6414	Remote Similarity	NPD6582	Phase 2
0.6412	Remote Similarity	NPD3028	Approved
0.6406	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD1791	Approved
0.6403	Remote Similarity	NPD9614	Approved
0.6403	Remote Similarity	NPD1793	Approved
0.6403	Remote Similarity	NPD9618	Approved
0.6395	Remote Similarity	NPD2194	Approved
0.6395	Remote Similarity	NPD2195	Approved
0.6392	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD9273	Approved
0.6382	Remote Similarity	NPD3052	Approved
0.6382	Remote Similarity	NPD3054	Approved
0.638	Remote Similarity	NPD7495	Discontinued
0.638	Remote Similarity	NPD8019	Approved
0.6378	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD256	Approved
0.6357	Remote Similarity	NPD255	Approved
0.6351	Remote Similarity	NPD4993	Discontinued
0.6346	Remote Similarity	NPD2458	Approved
0.6346	Remote Similarity	NPD2459	Approved
0.6346	Remote Similarity	NPD2460	Phase 3
0.6345	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD111	Approved
0.6329	Remote Similarity	NPD7554	Discontinued
0.6327	Remote Similarity	NPD1135	Approved
0.6327	Remote Similarity	NPD1129	Approved
0.6327	Remote Similarity	NPD1134	Approved
0.6327	Remote Similarity	NPD1133	Approved
0.6327	Remote Similarity	NPD1131	Approved
0.6316	Remote Similarity	NPD4658	Approved
0.6316	Remote Similarity	NPD4656	Approved
0.6306	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6331	Phase 2
0.6291	Remote Similarity	NPD839	Approved
0.6291	Remote Similarity	NPD840	Approved
0.6289	Remote Similarity	NPD3359	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD1242	Phase 1
0.6286	Remote Similarity	NPD475	Phase 2
0.6284	Remote Similarity	NPD6584	Phase 3
0.6273	Remote Similarity	NPD7523	Phase 3
0.6273	Remote Similarity	NPD7131	Phase 3
0.6272	Remote Similarity	NPD4010	Discontinued
0.6269	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD9244	Approved
0.6268	Remote Similarity	NPD9613	Approved
0.6268	Remote Similarity	NPD9616	Approved
0.6268	Remote Similarity	NPD9615	Approved
0.6267	Remote Similarity	NPD1024	Discontinued
0.6259	Remote Similarity	NPD2496	Approved
0.6259	Remote Similarity	NPD2497	Approved
0.6259	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9381	Approved
0.625	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3985	Discontinued
0.625	Remote Similarity	NPD2874	Phase 2
0.625	Remote Similarity	NPD6690	Approved
0.625	Remote Similarity	NPD4123	Phase 3
0.625	Remote Similarity	NPD9384	Approved
0.625	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD940	Approved
0.6241	Remote Similarity	NPD4818	Approved
0.6241	Remote Similarity	NPD4817	Approved
0.6241	Remote Similarity	NPD846	Approved
0.6233	Remote Similarity	NPD2233	Approved
0.6233	Remote Similarity	NPD2230	Approved
0.6233	Remote Similarity	NPD2232	Approved
0.6225	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD316	Approved
0.622	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6072	Discontinued
0.622	Remote Similarity	NPD7438	Suspended
0.6216	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD4108	Discontinued
0.6194	Remote Similarity	NPD3682	Approved
0.6194	Remote Similarity	NPD4231	Approved
0.6194	Remote Similarity	NPD4229	Approved
0.6194	Remote Similarity	NPD3680	Approved
0.619	Remote Similarity	NPD9622	Approved
0.619	Remote Similarity	NPD3685	Discontinued
0.6178	Remote Similarity	NPD7153	Discontinued
0.6169	Remote Similarity	NPD2157	Approved
0.6154	Remote Similarity	NPD2161	Phase 2
0.6154	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1725	Approved
0.6154	Remote Similarity	NPD6360	Discontinued
0.6149	Remote Similarity	NPD2922	Phase 1
0.6149	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD4739	Approved
0.6144	Remote Similarity	NPD4445	Approved
0.6144	Remote Similarity	NPD1555	Discontinued
0.6139	Remote Similarity	NPD3060	Approved
0.6138	Remote Similarity	NPD2286	Discontinued

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