NPASS Compound

Structure

NPC109968 OpenBabel07101718192D 34 35 0 0 0 0 0 0 0 0999 V2000 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6603 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6603 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0622 4.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 -0.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.3301 2.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.7942 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.5263 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.5263 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5263 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7942 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 29 1 0 0 0 0 3 33 1 0 0 0 0 4 9 1 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 27 1 0 0 0 0 9 29 1 0 0 0 0 10 34 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 19 2 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 28 2 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 27 2 3 0 0 0 23 30 1 0 0 0 0 28 31 1 0 0 0 0 29 32 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	662.96
Volume:	502.952
LogP:	3.37
LogD:	1.266
LogS:	-1.649
# Rotatable Bonds:	13
TPSA:	103.21
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.109
Synthetic Accessibility Score:	3.069
Fsp3:	0.391
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:	-5.408
MDCK Permeability:	1.8046994227916002e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.685
20% Bioavailability (F20%):	0.881
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	97.33089447021484%
Volume Distribution (VD):	1.395
Pgp-substrate:	1.922363042831421%

ADMET: Metabolism

CYP1A2-inhibitor:	0.648
CYP1A2-substrate:	0.586
CYP2C19-inhibitor:	0.754
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.524
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.848
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	1.243
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.376
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.081
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.176
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.049
Carcinogencity:	0.434
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC109968

Natural Product ID:	NPC109968
*Common Name:**	Purpureamine J
IUPAC Name:	3-[2,6-dibromo-4-[2-[[(2E)-3-(3-bromo-4-methoxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyl]phenoxy]-N,N-dimethylpropan-1-amine oxide
Synonyms:	Purpureamine J
Standard InCHIKey:	FRLHXVVWMAEBOU-VFCFBJKWSA-N
Standard InCHI:	InChI=1S/C23H28Br3N3O5/c1-29(2,32)9-4-10-34-22-18(25)12-16(13-19(22)26)7-8-27-23(30)20(28-31)14-15-5-6-21(33-3)17(24)11-15/h5-6,11-13,31H,4,7-10,14H2,1-3H3,(H,27,30)/b28-20+
SMILES:	O/N=C(/C(=NCCc1cc(Br)c(c(c1)Br)OCCCN(=O)(C)C)O)Cc1ccc(c(c1)Br)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464284
PubChem CID:	6400896
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO33394	druinella sp.	Species	n.a.	n.a.	n.a.	Fujian, China	n.a.	PMID[12502317]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	ID50	=	6.77	ug ml-1	PMID[540258]
NPT111	Cell Line	K562	Homo sapiens	ID50	=	5.97	ug ml-1	PMID[540258]

☑ 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 NPC109968 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	217
0.1-0.2	2417
0.2-0.3	12626
0.3-0.4	5592
0.4-0.5	12307
0.5-0.6	8517
0.6-0.7	874
0.7-0.8	122
0.8-0.85	10
0.85-0.9	7
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC258222
0.906	High Similarity	NPC156311
0.8733	High Similarity	NPC47672
0.863	High Similarity	NPC474128
0.8562	High Similarity	NPC233926
0.8514	High Similarity	NPC135349
0.8267	Intermediate Similarity	NPC78530
0.8235	Intermediate Similarity	NPC76412
0.8169	Intermediate Similarity	NPC110131
0.8014	Intermediate Similarity	NPC475735
0.7945	Intermediate Similarity	NPC474091
0.7756	Intermediate Similarity	NPC296085
0.7706	Intermediate Similarity	NPC475396
0.7682	Intermediate Similarity	NPC470471
0.7643	Intermediate Similarity	NPC71629
0.7633	Intermediate Similarity	NPC469979
0.7603	Intermediate Similarity	NPC272463
0.7588	Intermediate Similarity	NPC298981
0.7588	Intermediate Similarity	NPC207819
0.7588	Intermediate Similarity	NPC473462
0.7588	Intermediate Similarity	NPC110454
0.7588	Intermediate Similarity	NPC126128
0.7586	Intermediate Similarity	NPC473892
0.7586	Intermediate Similarity	NPC475658
0.7582	Intermediate Similarity	NPC213471
0.7582	Intermediate Similarity	NPC470470
0.7582	Intermediate Similarity	NPC474673
0.7564	Intermediate Similarity	NPC470472
0.7533	Intermediate Similarity	NPC473724
0.7529	Intermediate Similarity	NPC259071
0.7529	Intermediate Similarity	NPC226001
0.7529	Intermediate Similarity	NPC77435
0.7516	Intermediate Similarity	NPC309667
0.75	Intermediate Similarity	NPC477255
0.7483	Intermediate Similarity	NPC474753
0.7472	Intermediate Similarity	NPC227953
0.7471	Intermediate Similarity	NPC225130
0.7457	Intermediate Similarity	NPC301941
0.7457	Intermediate Similarity	NPC214188
0.7457	Intermediate Similarity	NPC74618
0.7443	Intermediate Similarity	NPC473409
0.7443	Intermediate Similarity	NPC141405
0.7443	Intermediate Similarity	NPC82741
0.7434	Intermediate Similarity	NPC163810
0.7429	Intermediate Similarity	NPC121571
0.7429	Intermediate Similarity	NPC8093
0.7414	Intermediate Similarity	NPC477254
0.7386	Intermediate Similarity	NPC471591
0.7386	Intermediate Similarity	NPC120114
0.7386	Intermediate Similarity	NPC71888
0.7386	Intermediate Similarity	NPC303993
0.7372	Intermediate Similarity	NPC212850
0.7372	Intermediate Similarity	NPC83289
0.7372	Intermediate Similarity	NPC189724
0.7341	Intermediate Similarity	NPC290534
0.7333	Intermediate Similarity	NPC202866
0.733	Intermediate Similarity	NPC49172
0.7308	Intermediate Similarity	NPC128877
0.729	Intermediate Similarity	NPC474587
0.729	Intermediate Similarity	NPC475132
0.7288	Intermediate Similarity	NPC144823
0.7278	Intermediate Similarity	NPC308571
0.7278	Intermediate Similarity	NPC474678
0.7278	Intermediate Similarity	NPC471338
0.726	Intermediate Similarity	NPC263835
0.7247	Intermediate Similarity	NPC147847
0.7244	Intermediate Similarity	NPC475293
0.7239	Intermediate Similarity	NPC469711
0.7238	Intermediate Similarity	NPC469721
0.7238	Intermediate Similarity	NPC475843
0.7191	Intermediate Similarity	NPC174607
0.7188	Intermediate Similarity	NPC247298
0.7184	Intermediate Similarity	NPC475615
0.7179	Intermediate Similarity	NPC470249
0.7158	Intermediate Similarity	NPC469731
0.7143	Intermediate Similarity	NPC274732
0.7135	Intermediate Similarity	NPC471337
0.7134	Intermediate Similarity	NPC197045
0.7124	Intermediate Similarity	NPC99280
0.7105	Intermediate Similarity	NPC202776
0.7099	Intermediate Similarity	NPC245974
0.7097	Intermediate Similarity	NPC184465
0.7075	Intermediate Similarity	NPC43275
0.7056	Intermediate Similarity	NPC470951
0.7043	Intermediate Similarity	NPC123140
0.7032	Intermediate Similarity	NPC166624
0.7032	Intermediate Similarity	NPC470392
0.703	Intermediate Similarity	NPC475432
0.7027	Intermediate Similarity	NPC321133
0.6968	Remote Similarity	NPC11449
0.6966	Remote Similarity	NPC475283
0.6966	Remote Similarity	NPC152205
0.6962	Remote Similarity	NPC470248
0.6923	Remote Similarity	NPC471953
0.6923	Remote Similarity	NPC247018
0.6923	Remote Similarity	NPC97870
0.6923	Remote Similarity	NPC307123
0.6908	Remote Similarity	NPC95733
0.6908	Remote Similarity	NPC62101
0.6885	Remote Similarity	NPC248822
0.6875	Remote Similarity	NPC471336
0.6875	Remote Similarity	NPC470746
0.6875	Remote Similarity	NPC40321
0.6864	Remote Similarity	NPC473738
0.6863	Remote Similarity	NPC29477
0.6846	Remote Similarity	NPC256369
0.6842	Remote Similarity	NPC211218
0.6832	Remote Similarity	NPC470709
0.68	Remote Similarity	NPC471308
0.68	Remote Similarity	NPC53596
0.68	Remote Similarity	NPC17388
0.68	Remote Similarity	NPC289330
0.68	Remote Similarity	NPC160120
0.6792	Remote Similarity	NPC475828
0.6776	Remote Similarity	NPC471314
0.6776	Remote Similarity	NPC471315
0.6774	Remote Similarity	NPC159987
0.6774	Remote Similarity	NPC122359
0.6774	Remote Similarity	NPC78061
0.6759	Remote Similarity	NPC166837
0.6752	Remote Similarity	NPC114102
0.6748	Remote Similarity	NPC470247
0.6742	Remote Similarity	NPC143450
0.6737	Remote Similarity	NPC156055
0.6701	Remote Similarity	NPC471339
0.6687	Remote Similarity	NPC235633
0.6687	Remote Similarity	NPC132771
0.6667	Remote Similarity	NPC116562
0.6667	Remote Similarity	NPC251571
0.6667	Remote Similarity	NPC470250
0.6667	Remote Similarity	NPC26524
0.6667	Remote Similarity	NPC254700
0.6647	Remote Similarity	NPC20755
0.6623	Remote Similarity	NPC328267
0.6622	Remote Similarity	NPC115803
0.6608	Remote Similarity	NPC56635
0.6604	Remote Similarity	NPC214869
0.6603	Remote Similarity	NPC301713
0.6597	Remote Similarity	NPC473450
0.6582	Remote Similarity	NPC35961
0.6582	Remote Similarity	NPC195902
0.6582	Remote Similarity	NPC195749
0.6582	Remote Similarity	NPC52029
0.6582	Remote Similarity	NPC135173
0.6581	Remote Similarity	NPC213414
0.6577	Remote Similarity	NPC303370
0.6577	Remote Similarity	NPC317254
0.6573	Remote Similarity	NPC470393
0.6561	Remote Similarity	NPC153990
0.6554	Remote Similarity	NPC59387
0.655	Remote Similarity	NPC471335
0.6548	Remote Similarity	NPC115144
0.6548	Remote Similarity	NPC277857
0.6538	Remote Similarity	NPC320242
0.6536	Remote Similarity	NPC83279
0.6528	Remote Similarity	NPC231705
0.6527	Remote Similarity	NPC313414
0.6519	Remote Similarity	NPC155838
0.651	Remote Similarity	NPC118202
0.6507	Remote Similarity	NPC258056
0.6503	Remote Similarity	NPC204848
0.6503	Remote Similarity	NPC41473
0.6503	Remote Similarity	NPC14600
0.6503	Remote Similarity	NPC312770
0.6503	Remote Similarity	NPC160607
0.6503	Remote Similarity	NPC38079
0.6503	Remote Similarity	NPC108875
0.65	Remote Similarity	NPC130595
0.65	Remote Similarity	NPC93882
0.6497	Remote Similarity	NPC218323
0.6494	Remote Similarity	NPC123848
0.6494	Remote Similarity	NPC475326
0.649	Remote Similarity	NPC38458
0.649	Remote Similarity	NPC311737
0.649	Remote Similarity	NPC323948
0.6474	Remote Similarity	NPC236265
0.6471	Remote Similarity	NPC41801
0.6463	Remote Similarity	NPC299583
0.6463	Remote Similarity	NPC474149
0.6463	Remote Similarity	NPC473358
0.6463	Remote Similarity	NPC210086
0.646	Remote Similarity	NPC313737
0.646	Remote Similarity	NPC6854
0.646	Remote Similarity	NPC169766
0.646	Remote Similarity	NPC285078
0.6456	Remote Similarity	NPC186898
0.6456	Remote Similarity	NPC280736
0.6452	Remote Similarity	NPC296202
0.645	Remote Similarity	NPC324081
0.6438	Remote Similarity	NPC309982
0.6424	Remote Similarity	NPC258992
0.6424	Remote Similarity	NPC82963
0.642	Remote Similarity	NPC218530
0.6416	Remote Similarity	NPC212699
0.6416	Remote Similarity	NPC207675
0.6415	Remote Similarity	NPC283079
0.6412	Remote Similarity	NPC471032
0.6412	Remote Similarity	NPC470935
0.641	Remote Similarity	NPC105999
0.6407	Remote Similarity	NPC178466

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 NPC109968 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	704
0.2-0.3	1226
0.3-0.4	2090
0.4-0.5	2895
0.5-0.6	1636
0.6-0.7	427
0.7-0.8	19
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
0.7415	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD821	Approved
0.7117	Intermediate Similarity	NPD2184	Approved
0.7117	Intermediate Similarity	NPD2183	Approved
0.7086	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2667	Approved
0.7027	Intermediate Similarity	NPD2668	Approved
0.6981	Remote Similarity	NPD1725	Approved
0.6923	Remote Similarity	NPD1423	Approved
0.6923	Remote Similarity	NPD5745	Approved
0.6923	Remote Similarity	NPD7477	Discontinued
0.6852	Remote Similarity	NPD2459	Approved
0.6852	Remote Similarity	NPD2458	Approved
0.6852	Remote Similarity	NPD2460	Phase 3
0.6832	Remote Similarity	NPD3656	Approved
0.6824	Remote Similarity	NPD5773	Approved
0.6824	Remote Similarity	NPD5772	Approved
0.6795	Remote Similarity	NPD5746	Approved
0.6792	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4993	Discontinued
0.6768	Remote Similarity	NPD3692	Discontinued
0.6766	Remote Similarity	NPD7131	Phase 3
0.6732	Remote Similarity	NPD3685	Discontinued
0.6732	Remote Similarity	NPD6583	Phase 3
0.6732	Remote Similarity	NPD6582	Phase 2
0.6706	Remote Similarity	NPD6072	Discontinued
0.6687	Remote Similarity	NPD7153	Discontinued
0.6687	Remote Similarity	NPD2157	Approved
0.6687	Remote Similarity	NPD3054	Approved
0.6687	Remote Similarity	NPD6087	Phase 1
0.6687	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3052	Approved
0.6667	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1712	Approved
0.6667	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2161	Phase 2
0.6647	Remote Similarity	NPD2874	Phase 2
0.6647	Remote Similarity	NPD4123	Phase 3
0.6646	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3596	Phase 2
0.6624	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2428	Approved
0.6623	Remote Similarity	NPD2429	Approved
0.6623	Remote Similarity	NPD1669	Approved
0.6607	Remote Similarity	NPD7526	Approved
0.6607	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD52	Approved
0.6606	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6331	Phase 2
0.6605	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6584	Phase 3
0.6582	Remote Similarity	NPD5163	Phase 2
0.6579	Remote Similarity	NPD2556	Approved
0.6579	Remote Similarity	NPD2554	Approved
0.6558	Remote Similarity	NPD2230	Approved
0.6558	Remote Similarity	NPD2233	Approved
0.6558	Remote Similarity	NPD2232	Approved
0.6556	Remote Similarity	NPD6581	Approved
0.6556	Remote Similarity	NPD2486	Discontinued
0.6556	Remote Similarity	NPD6580	Approved
0.6554	Remote Similarity	NPD7608	Discontinued
0.6548	Remote Similarity	NPD6419	Discontinued
0.6548	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7019	Approved
0.6548	Remote Similarity	NPD7020	Approved
0.6548	Remote Similarity	NPD3985	Discontinued
0.6545	Remote Similarity	NPD44	Approved
0.6545	Remote Similarity	NPD6364	Approved
0.6541	Remote Similarity	NPD1039	Discontinued
0.6541	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1817	Approved
0.6538	Remote Similarity	NPD4098	Discontinued
0.6538	Remote Similarity	NPD1818	Approved
0.6538	Remote Similarity	NPD1819	Approved
0.6538	Remote Similarity	NPD1820	Approved
0.6536	Remote Similarity	NPD3421	Phase 3
0.6514	Remote Similarity	NPD8070	Approved
0.6513	Remote Similarity	NPD2595	Approved
0.6513	Remote Similarity	NPD6382	Discontinued
0.6513	Remote Similarity	NPD2594	Approved
0.6513	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6380	Phase 1
0.6503	Remote Similarity	NPD2802	Phase 3
0.65	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2674	Phase 3
0.6494	Remote Similarity	NPD7318	Phase 3
0.6485	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3167	Approved
0.6478	Remote Similarity	NPD3179	Approved
0.6478	Remote Similarity	NPD3180	Approved
0.6478	Remote Similarity	NPD3164	Approved
0.6478	Remote Similarity	NPD3166	Approved
0.6478	Remote Similarity	NPD3165	Approved
0.6474	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2122	Discontinued
0.6467	Remote Similarity	NPD2557	Approved
0.6463	Remote Similarity	NPD3156	Discontinued
0.6453	Remote Similarity	NPD4678	Approved
0.6453	Remote Similarity	NPD4675	Approved
0.6452	Remote Similarity	NPD2231	Phase 2
0.6452	Remote Similarity	NPD2235	Phase 2
0.6446	Remote Similarity	NPD4162	Approved
0.6446	Remote Similarity	NPD4237	Approved
0.6446	Remote Similarity	NPD4236	Phase 3
0.6442	Remote Similarity	NPD696	Discontinued
0.6429	Remote Similarity	NPD3294	Phase 2
0.6424	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.642	Remote Similarity	NPD654	Phase 3
0.6412	Remote Similarity	NPD6390	Discontinued
0.6412	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD3444	Approved
0.6405	Remote Similarity	NPD3049	Approved
0.6405	Remote Similarity	NPD3445	Approved
0.6405	Remote Similarity	NPD3443	Approved
0.6398	Remote Similarity	NPD4475	Approved
0.6398	Remote Similarity	NPD839	Approved
0.6398	Remote Similarity	NPD4474	Approved
0.6398	Remote Similarity	NPD840	Approved
0.6395	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7018	Phase 2
0.6384	Remote Similarity	NPD6862	Phase 2
0.6379	Remote Similarity	NPD7317	Phase 3
0.6358	Remote Similarity	NPD2238	Phase 2
0.6358	Remote Similarity	NPD3140	Approved
0.6358	Remote Similarity	NPD3142	Approved
0.6353	Remote Similarity	NPD4739	Approved
0.6353	Remote Similarity	NPD3536	Discontinued
0.6348	Remote Similarity	NPD1411	Approved
0.6347	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5267	Discontinued
0.6335	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD3145	Approved
0.6335	Remote Similarity	NPD3144	Approved
0.6333	Remote Similarity	NPD2229	Approved
0.6333	Remote Similarity	NPD2228	Approved
0.6333	Remote Similarity	NPD2234	Approved
0.6331	Remote Similarity	NPD6667	Approved
0.6331	Remote Similarity	NPD6666	Approved
0.6329	Remote Similarity	NPD1794	Approved
0.6328	Remote Similarity	NPD8031	Discontinued
0.6327	Remote Similarity	NPD2684	Approved
0.6322	Remote Similarity	NPD7438	Suspended
0.6316	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7484	Phase 3
0.6313	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD5649	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7485	Phase 3
0.6306	Remote Similarity	NPD6539	Approved
0.6306	Remote Similarity	NPD6543	Approved
0.6306	Remote Similarity	NPD6542	Approved
0.6306	Remote Similarity	NPD4129	Approved
0.6306	Remote Similarity	NPD6540	Phase 3
0.6303	Remote Similarity	NPD4108	Discontinued
0.6296	Remote Similarity	NPD7265	Discontinued
0.6296	Remote Similarity	NPD2245	Discovery
0.6294	Remote Similarity	NPD7213	Phase 3
0.6294	Remote Similarity	NPD7212	Phase 2
0.6291	Remote Similarity	NPD595	Approved
0.6291	Remote Similarity	NPD593	Approved
0.629	Remote Similarity	NPD3337	Discontinued
0.6289	Remote Similarity	NPD2987	Approved
0.6289	Remote Similarity	NPD2990	Approved
0.6289	Remote Similarity	NPD3690	Phase 2
0.6289	Remote Similarity	NPD3691	Phase 2
0.6286	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD4010	Discontinued
0.6273	Remote Similarity	NPD1024	Discontinued
0.6273	Remote Similarity	NPD9718	Approved
0.6267	Remote Similarity	NPD7843	Approved
0.6266	Remote Similarity	NPD6538	Approved
0.6266	Remote Similarity	NPD6541	Approved
0.6265	Remote Similarity	NPD4477	Approved
0.6265	Remote Similarity	NPD6032	Approved
0.6265	Remote Similarity	NPD2239	Approved
0.6265	Remote Similarity	NPD4476	Approved
0.6265	Remote Similarity	NPD2240	Approved
0.6264	Remote Similarity	NPD3679	Phase 2
0.6259	Remote Similarity	NPD5373	Approved
0.6259	Remote Similarity	NPD5374	Approved
0.6258	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD7447	Phase 1
0.6257	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD2504	Approved
0.6257	Remote Similarity	NPD2505	Approved
0.6257	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5289	Phase 2
0.625	Remote Similarity	NPD7972	Discontinued
0.625	Remote Similarity	NPD2250	Discontinued
0.6242	Remote Similarity	NPD2200	Suspended
0.6235	Remote Similarity	NPD5756	Phase 2
0.6235	Remote Similarity	NPD1048	Approved
0.6235	Remote Similarity	NPD5295	Discontinued
0.6235	Remote Similarity	NPD5718	Phase 2

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