NPASS Compound

Structure

NPC156311 OpenBabel07101719132D 32 33 0 0 0 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 4.0000 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 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 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 -3.4641 1.0000 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 -6.9282 4.0000 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 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -7.7942 4.5000 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 5.5000 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 0.8660 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 4.5000 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 1 26 1 0 0 0 0 2 31 1 0 0 0 0 3 7 1 0 0 0 0 3 9 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 20 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 26 1 0 0 0 0 8 27 1 0 0 0 0 9 32 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 28 2 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 22 27 2 3 0 0 0 22 29 1 0 0 0 0 28 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	632.95
Volume:	476.866
LogP:	4.313
LogD:	3.127
LogS:	-4.384
# Rotatable Bonds:	13
TPSA:	92.18
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.136
Synthetic Accessibility Score:	2.745
Fsp3:	0.364
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:	-5.003
MDCK Permeability:	1.6576666894252412e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.142
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	97.38540649414062%
Volume Distribution (VD):	2.23
Pgp-substrate:	2.3971760272979736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.86
CYP1A2-substrate:	0.532
CYP2C19-inhibitor:	0.94
CYP2C19-substrate:	0.408
CYP2C9-inhibitor:	0.801
CYP2C9-substrate:	0.589
CYP2D6-inhibitor:	0.956
CYP2D6-substrate:	0.801
CYP3A4-inhibitor:	0.962
CYP3A4-substrate:	0.477

ADMET: Excretion

Clearance (CL):	1.045
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.838
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.4
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.365
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.342
Carcinogencity:	0.105
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.177

Download Data

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

Natural Product: NPC156311

Natural Product ID:	NPC156311
*Common Name:**	Purpureamine I
IUPAC Name:	(2E)-3-(3-bromo-4-methoxyphenyl)-N-[2-[3,5-dibromo-4-[3-(methylamino)propoxy]phenyl]ethyl]-2-hydroxyiminopropanamide
Synonyms:	Purpuramine-1; Purpureamine I
Standard InCHIKey:	QNWJAZMBGXECMI-TURZUDJPSA-N
Standard InCHI:	InChI=1S/C22H26Br3N3O4/c1-26-7-3-9-32-21-17(24)11-15(12-18(21)25)6-8-27-22(29)19(28-30)13-14-4-5-20(31-2)16(23)10-14/h4-5,10-12,26,30H,3,6-9,13H2,1-2H3,(H,27,29)/b28-19+
SMILES:	CNCCCOc1c(Br)cc(cc1Br)CCN=C(/C(=N/O)/Cc1ccc(c(c1)Br)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465039
PubChem CID:	11764681
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]
NPO33308	psammaplysilla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15844952]
NPO40724	Pseudoceratina cf. verrucosa	Strain	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28085276]

☑ 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	=	1.7	ug ml-1	PMID[543132]
NPT111	Cell Line	K562	Homo sapiens	ID50	=	1.24	ug ml-1	PMID[543132]

☑ 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 NPC156311 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	230
0.1-0.2	2544
0.2-0.3	12953
0.3-0.4	5039
0.4-0.5	13541
0.5-0.6	7530
0.6-0.7	722
0.7-0.8	113
0.8-0.85	13
0.85-0.9	3
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9586	High Similarity	NPC258222
0.9388	High Similarity	NPC47672
0.9329	High Similarity	NPC233926
0.906	High Similarity	NPC109968
0.9041	High Similarity	NPC78530
0.8993	High Similarity	NPC76412
0.8904	High Similarity	NPC474128
0.8658	High Similarity	NPC135349
0.8411	Intermediate Similarity	NPC470472
0.8311	Intermediate Similarity	NPC470471
0.8288	Intermediate Similarity	NPC475735
0.8219	Intermediate Similarity	NPC474091
0.82	Intermediate Similarity	NPC470470
0.8125	Intermediate Similarity	NPC272463
0.8079	Intermediate Similarity	NPC474673
0.8069	Intermediate Similarity	NPC110131
0.8061	Intermediate Similarity	NPC477255
0.7965	Intermediate Similarity	NPC8093
0.7965	Intermediate Similarity	NPC259071
0.7965	Intermediate Similarity	NPC121571
0.7965	Intermediate Similarity	NPC77435
0.7941	Intermediate Similarity	NPC475396
0.7908	Intermediate Similarity	NPC128877
0.7898	Intermediate Similarity	NPC296085
0.7898	Intermediate Similarity	NPC227953
0.7871	Intermediate Similarity	NPC308571
0.787	Intermediate Similarity	NPC469979
0.7849	Intermediate Similarity	NPC477254
0.7843	Intermediate Similarity	NPC213471
0.7824	Intermediate Similarity	NPC126128
0.7824	Intermediate Similarity	NPC110454
0.7824	Intermediate Similarity	NPC473462
0.7824	Intermediate Similarity	NPC207819
0.7824	Intermediate Similarity	NPC298981
0.7816	Intermediate Similarity	NPC475658
0.7816	Intermediate Similarity	NPC473892
0.7812	Intermediate Similarity	NPC469711
0.78	Intermediate Similarity	NPC473724
0.7797	Intermediate Similarity	NPC471338
0.7797	Intermediate Similarity	NPC474678
0.7785	Intermediate Similarity	NPC71629
0.7778	Intermediate Similarity	NPC309667
0.7765	Intermediate Similarity	NPC226001
0.7753	Intermediate Similarity	NPC475843
0.7727	Intermediate Similarity	NPC197045
0.7706	Intermediate Similarity	NPC225130
0.7688	Intermediate Similarity	NPC301941
0.7688	Intermediate Similarity	NPC214188
0.7688	Intermediate Similarity	NPC74618
0.767	Intermediate Similarity	NPC141405
0.767	Intermediate Similarity	NPC473409
0.767	Intermediate Similarity	NPC82741
0.7654	Intermediate Similarity	NPC202866
0.7647	Intermediate Similarity	NPC303993
0.7647	Intermediate Similarity	NPC120114
0.7647	Intermediate Similarity	NPC71888
0.7637	Intermediate Similarity	NPC471337
0.7614	Intermediate Similarity	NPC174607
0.7614	Intermediate Similarity	NPC471591
0.7572	Intermediate Similarity	NPC290534
0.7571	Intermediate Similarity	NPC147847
0.7557	Intermediate Similarity	NPC49172
0.7548	Intermediate Similarity	NPC475132
0.7548	Intermediate Similarity	NPC474587
0.7541	Intermediate Similarity	NPC123140
0.7534	Intermediate Similarity	NPC263835
0.7516	Intermediate Similarity	NPC247018
0.7516	Intermediate Similarity	NPC212850
0.7516	Intermediate Similarity	NPC307123
0.7516	Intermediate Similarity	NPC474753
0.7516	Intermediate Similarity	NPC83289
0.7516	Intermediate Similarity	NPC189724
0.7516	Intermediate Similarity	NPC97870
0.7514	Intermediate Similarity	NPC144823
0.75	Intermediate Similarity	NPC475293
0.7468	Intermediate Similarity	NPC163810
0.7459	Intermediate Similarity	NPC469721
0.745	Intermediate Similarity	NPC328267
0.7414	Intermediate Similarity	NPC475615
0.7386	Intermediate Similarity	NPC99280
0.7377	Intermediate Similarity	NPC469731
0.7354	Intermediate Similarity	NPC471336
0.7354	Intermediate Similarity	NPC470746
0.7347	Intermediate Similarity	NPC43275
0.7329	Intermediate Similarity	NPC247298
0.7278	Intermediate Similarity	NPC470951
0.7273	Intermediate Similarity	NPC475432
0.7239	Intermediate Similarity	NPC245974
0.7226	Intermediate Similarity	NPC11449
0.7198	Intermediate Similarity	NPC248822
0.7195	Intermediate Similarity	NPC20755
0.7191	Intermediate Similarity	NPC475283
0.7191	Intermediate Similarity	NPC152205
0.7179	Intermediate Similarity	NPC471953
0.7179	Intermediate Similarity	NPC166624
0.7173	Intermediate Similarity	NPC471339
0.7172	Intermediate Similarity	NPC26524
0.7171	Intermediate Similarity	NPC95733
0.7171	Intermediate Similarity	NPC62101
0.7161	Intermediate Similarity	NPC135173
0.7152	Intermediate Similarity	NPC235633
0.7143	Intermediate Similarity	NPC202776
0.7134	Intermediate Similarity	NPC184465
0.7124	Intermediate Similarity	NPC320242
0.7124	Intermediate Similarity	NPC29477
0.7123	Intermediate Similarity	NPC115803
0.7114	Intermediate Similarity	NPC256369
0.7107	Intermediate Similarity	NPC470249
0.7105	Intermediate Similarity	NPC211218
0.7101	Intermediate Similarity	NPC473738
0.707	Intermediate Similarity	NPC274732
0.707	Intermediate Similarity	NPC470392
0.7067	Intermediate Similarity	NPC321133
0.7055	Intermediate Similarity	NPC59387
0.7039	Intermediate Similarity	NPC471314
0.7039	Intermediate Similarity	NPC471315
0.7032	Intermediate Similarity	NPC122359
0.7032	Intermediate Similarity	NPC78061
0.7032	Intermediate Similarity	NPC159987
0.7006	Intermediate Similarity	NPC114102
0.7005	Intermediate Similarity	NPC471335
0.6984	Remote Similarity	NPC473450
0.6975	Remote Similarity	NPC168861
0.6966	Remote Similarity	NPC143450
0.6947	Remote Similarity	NPC156055
0.6943	Remote Similarity	NPC474087
0.6937	Remote Similarity	NPC237227
0.6928	Remote Similarity	NPC132771
0.6923	Remote Similarity	NPC251571
0.6908	Remote Similarity	NPC318357
0.6903	Remote Similarity	NPC136112
0.6903	Remote Similarity	NPC141739
0.6894	Remote Similarity	NPC470248
0.6887	Remote Similarity	NPC283760
0.6879	Remote Similarity	NPC22014
0.6859	Remote Similarity	NPC301713
0.6855	Remote Similarity	NPC214869
0.6852	Remote Similarity	NPC214988
0.6852	Remote Similarity	NPC231163
0.6852	Remote Similarity	NPC318591
0.6846	Remote Similarity	NPC303370
0.6842	Remote Similarity	NPC56635
0.6842	Remote Similarity	NPC53596
0.6842	Remote Similarity	NPC471308
0.6842	Remote Similarity	NPC160120
0.6842	Remote Similarity	NPC17388
0.6842	Remote Similarity	NPC289330
0.6839	Remote Similarity	NPC213414
0.6835	Remote Similarity	NPC52029
0.6835	Remote Similarity	NPC35961
0.6835	Remote Similarity	NPC195749
0.6829	Remote Similarity	NPC204546
0.6828	Remote Similarity	NPC97811
0.6813	Remote Similarity	NPC267237
0.6811	Remote Similarity	NPC246591
0.681	Remote Similarity	NPC40321
0.6803	Remote Similarity	NPC166837
0.68	Remote Similarity	NPC254700
0.6797	Remote Similarity	NPC83279
0.6786	Remote Similarity	NPC277857
0.6786	Remote Similarity	NPC115144
0.6772	Remote Similarity	NPC155838
0.6768	Remote Similarity	NPC470709
0.6766	Remote Similarity	NPC313414
0.6757	Remote Similarity	NPC96275
0.6755	Remote Similarity	NPC323948
0.6755	Remote Similarity	NPC38458
0.6755	Remote Similarity	NPC311737
0.6748	Remote Similarity	NPC312770
0.6748	Remote Similarity	NPC160607
0.6748	Remote Similarity	NPC14600
0.6748	Remote Similarity	NPC204848
0.6748	Remote Similarity	NPC41473
0.6736	Remote Similarity	NPC42383
0.6735	Remote Similarity	NPC473358
0.6732	Remote Similarity	NPC41801
0.6731	Remote Similarity	NPC236265
0.6724	Remote Similarity	NPC123848
0.671	Remote Similarity	NPC296202
0.671	Remote Similarity	NPC116562
0.671	Remote Similarity	NPC298486
0.6709	Remote Similarity	NPC186898
0.6707	Remote Similarity	NPC299583
0.6705	Remote Similarity	NPC287757
0.6705	Remote Similarity	NPC319320
0.6689	Remote Similarity	NPC82963
0.6687	Remote Similarity	NPC470247
0.6687	Remote Similarity	NPC326966
0.6686	Remote Similarity	NPC203424
0.6686	Remote Similarity	NPC206372
0.6667	Remote Similarity	NPC271808
0.6667	Remote Similarity	NPC325651
0.6667	Remote Similarity	NPC105999
0.6667	Remote Similarity	NPC471321
0.6667	Remote Similarity	NPC471306
0.6647	Remote Similarity	NPC212699
0.6647	Remote Similarity	NPC471032
0.6647	Remote Similarity	NPC207675
0.6647	Remote Similarity	NPC178466
0.6647	Remote Similarity	NPC63628

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 NPC156311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	668
0.2-0.3	1215
0.3-0.4	2003
0.4-0.5	3057
0.5-0.6	1574
0.6-0.7	455
0.7-0.8	27
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
0.7703	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2459	Approved
0.7643	Intermediate Similarity	NPD2460	Phase 3
0.7643	Intermediate Similarity	NPD2458	Approved
0.7516	Intermediate Similarity	NPD1423	Approved
0.7484	Intermediate Similarity	NPD3054	Approved
0.7484	Intermediate Similarity	NPD3052	Approved
0.7451	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2428	Approved
0.745	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2429	Approved
0.7415	Intermediate Similarity	NPD2554	Approved
0.7415	Intermediate Similarity	NPD2556	Approved
0.7407	Intermediate Similarity	NPD2874	Phase 2
0.7386	Intermediate Similarity	NPD5163	Phase 2
0.7346	Intermediate Similarity	NPD6087	Phase 1
0.7301	Intermediate Similarity	NPD3985	Discontinued
0.7233	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3049	Approved
0.7222	Intermediate Similarity	NPD821	Approved
0.7205	Intermediate Similarity	NPD4162	Approved
0.7179	Intermediate Similarity	NPD7477	Discontinued
0.7143	Intermediate Similarity	NPD7153	Discontinued
0.7124	Intermediate Similarity	NPD1820	Approved
0.7124	Intermediate Similarity	NPD1819	Approved
0.7124	Intermediate Similarity	NPD1817	Approved
0.7124	Intermediate Similarity	NPD1818	Approved
0.7099	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3536	Discontinued
0.7067	Intermediate Similarity	NPD2668	Approved
0.7067	Intermediate Similarity	NPD2667	Approved
0.7051	Intermediate Similarity	NPD3164	Approved
0.7051	Intermediate Similarity	NPD3167	Approved
0.7051	Intermediate Similarity	NPD3165	Approved
0.7051	Intermediate Similarity	NPD3166	Approved
0.7051	Intermediate Similarity	NPD3179	Approved
0.7051	Intermediate Similarity	NPD3180	Approved
0.7048	Intermediate Similarity	NPD7526	Approved
0.7048	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD52	Approved
0.7048	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2184	Approved
0.7048	Intermediate Similarity	NPD2183	Approved
0.7041	Intermediate Similarity	NPD6072	Discontinued
0.7039	Intermediate Similarity	NPD2231	Phase 2
0.7039	Intermediate Similarity	NPD2235	Phase 2
0.7037	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6419	Discontinued
0.6962	Remote Similarity	NPD3530	Approved
0.6962	Remote Similarity	NPD3531	Approved
0.6962	Remote Similarity	NPD3532	Approved
0.6957	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6179	Discontinued
0.6936	Remote Similarity	NPD8031	Discontinued
0.6923	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4993	Discontinued
0.6918	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7485	Phase 3
0.6914	Remote Similarity	NPD1725	Approved
0.6914	Remote Similarity	NPD7484	Phase 3
0.6914	Remote Similarity	NPD3156	Discontinued
0.6905	Remote Similarity	NPD7131	Phase 3
0.6903	Remote Similarity	NPD1794	Approved
0.6892	Remote Similarity	NPD593	Approved
0.6892	Remote Similarity	NPD595	Approved
0.689	Remote Similarity	NPD5062	Approved
0.689	Remote Similarity	NPD5061	Approved
0.689	Remote Similarity	NPD3060	Approved
0.6886	Remote Similarity	NPD7020	Approved
0.6886	Remote Similarity	NPD7019	Approved
0.6883	Remote Similarity	NPD6583	Phase 3
0.6883	Remote Similarity	NPD1669	Approved
0.6883	Remote Similarity	NPD6582	Phase 2
0.6875	Remote Similarity	NPD7608	Discontinued
0.6859	Remote Similarity	NPD7451	Discontinued
0.6855	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5745	Approved
0.6852	Remote Similarity	NPD2156	Approved
0.6852	Remote Similarity	NPD2154	Approved
0.6852	Remote Similarity	NPD6380	Phase 1
0.6852	Remote Similarity	NPD2155	Approved
0.6848	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6331	Phase 2
0.6832	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2561	Approved
0.6818	Remote Similarity	NPD2562	Approved
0.6815	Remote Similarity	NPD2250	Discontinued
0.681	Remote Similarity	NPD2239	Approved
0.681	Remote Similarity	NPD2240	Approved
0.6807	Remote Similarity	NPD5160	Discontinued
0.6807	Remote Similarity	NPD2677	Approved
0.6805	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3596	Phase 2
0.6786	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2505	Approved
0.6786	Remote Similarity	NPD2504	Approved
0.6786	Remote Similarity	NPD4123	Phase 3
0.6774	Remote Similarity	NPD3685	Discontinued
0.6774	Remote Similarity	NPD4129	Approved
0.6772	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2614	Approved
0.6768	Remote Similarity	NPD3656	Approved
0.6763	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5772	Approved
0.6763	Remote Similarity	NPD5773	Approved
0.6752	Remote Similarity	NPD6584	Phase 3
0.675	Remote Similarity	NPD3162	Approved
0.675	Remote Similarity	NPD839	Approved
0.675	Remote Similarity	NPD3163	Approved
0.675	Remote Similarity	NPD2245	Discovery
0.675	Remote Similarity	NPD840	Approved
0.6746	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5746	Approved
0.673	Remote Similarity	NPD9718	Approved
0.6728	Remote Similarity	NPD2157	Approved
0.6725	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3560	Approved
0.6724	Remote Similarity	NPD3557	Approved
0.6724	Remote Similarity	NPD3558	Approved
0.6724	Remote Similarity	NPD3556	Approved
0.6721	Remote Similarity	NPD2802	Phase 3
0.6711	Remote Similarity	NPD6580	Approved
0.6711	Remote Similarity	NPD6581	Approved
0.6711	Remote Similarity	NPD2486	Discontinued
0.6709	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1712	Approved
0.6707	Remote Similarity	NPD2161	Phase 2
0.6707	Remote Similarity	NPD3692	Discontinued
0.6706	Remote Similarity	NPD6031	Approved
0.6706	Remote Similarity	NPD6030	Approved
0.6705	Remote Similarity	NPD5355	Approved
0.6705	Remote Similarity	NPD5356	Approved
0.6688	Remote Similarity	NPD4098	Discontinued
0.6688	Remote Similarity	NPD3568	Approved
0.6688	Remote Similarity	NPD3567	Approved
0.6688	Remote Similarity	NPD3421	Phase 3
0.6687	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6364	Approved
0.6687	Remote Similarity	NPD1039	Discontinued
0.6687	Remote Similarity	NPD3554	Approved
0.6687	Remote Similarity	NPD3555	Approved
0.6687	Remote Similarity	NPD44	Approved
0.6687	Remote Similarity	NPD3553	Approved
0.6687	Remote Similarity	NPD3552	Approved
0.6686	Remote Similarity	NPD4180	Approved
0.6686	Remote Similarity	NPD4179	Approved
0.6683	Remote Similarity	NPD3336	Discovery
0.6667	Remote Similarity	NPD2595	Approved
0.6667	Remote Similarity	NPD6382	Discontinued
0.6667	Remote Similarity	NPD2594	Approved
0.6667	Remote Similarity	NPD5267	Discontinued
0.6667	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2215	Approved
0.6648	Remote Similarity	NPD4083	Discontinued
0.6648	Remote Similarity	NPD2216	Approved
0.6648	Remote Similarity	NPD8070	Approved
0.6647	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3691	Phase 2
0.6646	Remote Similarity	NPD558	Phase 2
0.6646	Remote Similarity	NPD3690	Phase 2
0.6629	Remote Similarity	NPD3511	Discontinued
0.6627	Remote Similarity	NPD4598	Approved
0.6627	Remote Similarity	NPD4597	Approved
0.6627	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2653	Approved
0.6625	Remote Similarity	NPD3136	Phase 2
0.6624	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2557	Approved
0.661	Remote Similarity	NPD5709	Phase 3
0.6609	Remote Similarity	NPD5722	Discontinued
0.6604	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD2233	Approved
0.6603	Remote Similarity	NPD2230	Approved
0.6603	Remote Similarity	NPD2232	Approved
0.6591	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4678	Approved
0.659	Remote Similarity	NPD4675	Approved
0.659	Remote Similarity	NPD1009	Approved
0.6585	Remote Similarity	NPD1536	Approved
0.6581	Remote Similarity	NPD3294	Phase 2
0.6573	Remote Similarity	NPD1411	Approved
0.6573	Remote Similarity	NPD4666	Phase 3
0.657	Remote Similarity	NPD3686	Approved
0.657	Remote Similarity	NPD3687	Approved
0.6566	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD3443	Approved
0.6558	Remote Similarity	NPD3444	Approved
0.6558	Remote Similarity	NPD3445	Approved
0.6552	Remote Similarity	NPD7438	Suspended
0.655	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4108	Discontinued
0.6543	Remote Similarity	NPD6405	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