NPASS Compound

Structure

NPC470470 OpenBabel07101719242D 28 28 0 0 0 0 0 0 0 0999 V2000 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -1.7321 -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 0.0000 -1.0000 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 -3.4641 -3.0000 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 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 -10.3923 -12.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -9.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -5.5000 0.0000 N 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 -3.4641 -4.0000 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 1 28 1 0 0 0 0 2 3 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 8 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 19 1 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 26 2 3 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	518.09
Volume:	432.872
LogP:	1.747
LogD:	1.157
LogS:	-2.507
# Rotatable Bonds:	16
TPSA:	88.41
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.211
Synthetic Accessibility Score:	2.57
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.964
MDCK Permeability:	7.54753682485898e-06
Pgp-inhibitor:	0.066
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	71.30997467041016%
Volume Distribution (VD):	0.848
Pgp-substrate:	52.87709045410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.308
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.198
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.203
CYP2D6-inhibitor:	0.5
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	1.571
Half-life (T1/2):	0.312

ADMET: Toxicity

hERG Blockers:	0.607
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.819
Maximum Recommended Daily Dose:	0.538
Skin Sensitization:	0.924
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC470470

Natural Product ID:	NPC470470
*Common Name:**	Ianthelliformisamine A
IUPAC Name:	(E)-N-[3-[4-(3-aminopropylamino)butylamino]propyl]-3-(3,5-dibromo-4-methoxyphenyl)prop-2-enamide
Synonyms:	Ianthelliformisamine A
Standard InCHIKey:	KVQQKKIHZWAGNU-VOTSOKGWSA-N
Standard InCHI:	InChI=1S/C20H32Br2N4O2/c1-28-20-17(21)14-16(15-18(20)22)6-7-19(27)26-13-5-12-25-10-3-2-9-24-11-4-8-23/h6-7,14-15,24-25H,2-5,8-13,23H2,1H3,(H,26,27)/b7-6+
SMILES:	COC1=C(C=C(C=C1Br)C=CC(=O)NCCCNCCCCNCCCN)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047172
PubChem CID:	59051760
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0002810] Cinnamic acid amides

*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
NPO32712	suberea ianthelliformis	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22515429]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
MIC	5
Others	4

Activity Type	# Activity
Organism	8
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	IC50	=	6800.0	nM	PMID[503858]
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	MIC	=	35000.0	nM	PMID[503858]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Inhibition	=	77.0	%	PMID[503858]
NPT2	Others	Unspecified		Activity	=	12.5	uM	PMID[503859]
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	MIC	=	200000.0	nM	PMID[503859]
NPT2	Others	Unspecified		Activity	>	100.0	uM	PMID[503859]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	>	100.0	uM	PMID[503859]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>	200000.0	nM	PMID[503859]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	200000.0	nM	PMID[503859]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	200000.0	nM	PMID[503859]

☑ 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 NPC470470 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	216
0.1-0.2	3112
0.2-0.3	13557
0.3-0.4	6230
0.4-0.5	14451
0.5-0.6	4601
0.6-0.7	460
0.7-0.8	60
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9845	High Similarity	NPC470471
0.9627	High Similarity	NPC470472
0.8873	High Similarity	NPC76412
0.8652	High Similarity	NPC78530
0.8521	High Similarity	NPC135349
0.8322	Intermediate Similarity	NPC233926
0.8243	Intermediate Similarity	NPC47672
0.82	Intermediate Similarity	NPC156311
0.8042	Intermediate Similarity	NPC213471
0.7956	Intermediate Similarity	NPC272463
0.7899	Intermediate Similarity	NPC110131
0.7877	Intermediate Similarity	NPC474128
0.7862	Intermediate Similarity	NPC128877
0.7832	Intermediate Similarity	NPC303993
0.7823	Intermediate Similarity	NPC308571
0.7815	Intermediate Similarity	NPC258222
0.7793	Intermediate Similarity	NPC474673
0.7655	Intermediate Similarity	NPC235633
0.7647	Intermediate Similarity	NPC469711
0.7582	Intermediate Similarity	NPC109968
0.7576	Intermediate Similarity	NPC166837
0.7552	Intermediate Similarity	NPC99280
0.7551	Intermediate Similarity	NPC197045
0.7537	Intermediate Similarity	NPC115803
0.75	Intermediate Similarity	NPC296085
0.75	Intermediate Similarity	NPC71629
0.7431	Intermediate Similarity	NPC135173
0.7362	Intermediate Similarity	NPC477255
0.7353	Intermediate Similarity	NPC303370
0.7333	Intermediate Similarity	NPC59387
0.731	Intermediate Similarity	NPC474087
0.7289	Intermediate Similarity	NPC143450
0.7278	Intermediate Similarity	NPC477254
0.726	Intermediate Similarity	NPC475735
0.7248	Intermediate Similarity	NPC470249
0.7214	Intermediate Similarity	NPC263835
0.7193	Intermediate Similarity	NPC77435
0.7193	Intermediate Similarity	NPC259071
0.7192	Intermediate Similarity	NPC474091
0.7143	Intermediate Similarity	NPC473724
0.7143	Intermediate Similarity	NPC256369
0.7143	Intermediate Similarity	NPC43275
0.7143	Intermediate Similarity	NPC227953
0.7133	Intermediate Similarity	NPC470248
0.7133	Intermediate Similarity	NPC309667
0.7095	Intermediate Similarity	NPC97870
0.7095	Intermediate Similarity	NPC307123
0.7095	Intermediate Similarity	NPC247018
0.7093	Intermediate Similarity	NPC121571
0.7093	Intermediate Similarity	NPC8093
0.7063	Intermediate Similarity	NPC116562
0.705	Intermediate Similarity	NPC258992
0.7047	Intermediate Similarity	NPC163810
0.7027	Intermediate Similarity	NPC11449
0.7014	Intermediate Similarity	NPC211218
0.7013	Intermediate Similarity	NPC470247
0.7007	Intermediate Similarity	NPC471321
0.7007	Intermediate Similarity	NPC471306
0.7006	Intermediate Similarity	NPC202866
0.7006	Intermediate Similarity	NPC20755
0.7	Intermediate Similarity	NPC120114
0.7	Intermediate Similarity	NPC71888
0.6992	Remote Similarity	NPC42383
0.698	Remote Similarity	NPC474753
0.698	Remote Similarity	NPC274732
0.6966	Remote Similarity	NPC62101
0.6966	Remote Similarity	NPC95733
0.6963	Remote Similarity	NPC146530
0.6949	Remote Similarity	NPC471338
0.6949	Remote Similarity	NPC474678
0.6939	Remote Similarity	NPC186898
0.6932	Remote Similarity	NPC248822
0.6928	Remote Similarity	NPC40321
0.6923	Remote Similarity	NPC83279
0.6918	Remote Similarity	NPC320242
0.691	Remote Similarity	NPC475843
0.6906	Remote Similarity	NPC471337
0.6901	Remote Similarity	NPC283760
0.6892	Remote Similarity	NPC271808
0.6889	Remote Similarity	NPC142297
0.6871	Remote Similarity	NPC251466
0.6871	Remote Similarity	NPC301713
0.6867	Remote Similarity	NPC158078
0.6867	Remote Similarity	NPC471953
0.686	Remote Similarity	NPC475396
0.6853	Remote Similarity	NPC53596
0.6853	Remote Similarity	NPC17388
0.6853	Remote Similarity	NPC160120
0.6853	Remote Similarity	NPC289330
0.6853	Remote Similarity	NPC471308
0.6838	Remote Similarity	NPC97811
0.6838	Remote Similarity	NPC309982
0.6828	Remote Similarity	NPC298486
0.6824	Remote Similarity	NPC291449
0.6824	Remote Similarity	NPC202776
0.6824	Remote Similarity	NPC122359
0.6824	Remote Similarity	NPC153990
0.6824	Remote Similarity	NPC159987
0.6824	Remote Similarity	NPC78061
0.6824	Remote Similarity	NPC41331
0.6824	Remote Similarity	NPC251571
0.6818	Remote Similarity	NPC470250
0.6803	Remote Similarity	NPC246133
0.6803	Remote Similarity	NPC170583
0.6803	Remote Similarity	NPC207541
0.6803	Remote Similarity	NPC152186
0.6803	Remote Similarity	NPC29477
0.6803	Remote Similarity	NPC71105
0.6803	Remote Similarity	NPC182147
0.6797	Remote Similarity	NPC474587
0.6797	Remote Similarity	NPC475132
0.6784	Remote Similarity	NPC469979
0.6781	Remote Similarity	NPC328267
0.6779	Remote Similarity	NPC155838
0.6774	Remote Similarity	NPC470709
0.6761	Remote Similarity	NPC473892
0.6761	Remote Similarity	NPC475658
0.6761	Remote Similarity	NPC174607
0.6761	Remote Similarity	NPC323948
0.6757	Remote Similarity	NPC156944
0.6755	Remote Similarity	NPC166624
0.6753	Remote Similarity	NPC475293
0.6752	Remote Similarity	NPC79076
0.6744	Remote Similarity	NPC473462
0.6744	Remote Similarity	NPC110454
0.6744	Remote Similarity	NPC298981
0.6744	Remote Similarity	NPC126128
0.6744	Remote Similarity	NPC207819
0.6739	Remote Similarity	NPC473358
0.6736	Remote Similarity	NPC321133
0.6736	Remote Similarity	NPC41801
0.6735	Remote Similarity	NPC300955
0.6733	Remote Similarity	NPC195749
0.6733	Remote Similarity	NPC35961
0.6733	Remote Similarity	NPC52029
0.6732	Remote Similarity	NPC237227
0.6723	Remote Similarity	NPC147847
0.6721	Remote Similarity	NPC123140
0.6721	Remote Similarity	NPC473450
0.6714	Remote Similarity	NPC26524
0.6711	Remote Similarity	NPC99798
0.6711	Remote Similarity	NPC184465
0.6711	Remote Similarity	NPC157740
0.6691	Remote Similarity	NPC231705
0.6689	Remote Similarity	NPC136112
0.6689	Remote Similarity	NPC141739
0.6686	Remote Similarity	NPC226001
0.6667	Remote Similarity	NPC212850
0.6667	Remote Similarity	NPC246974
0.6667	Remote Similarity	NPC189724
0.6667	Remote Similarity	NPC54543
0.6667	Remote Similarity	NPC147247
0.6667	Remote Similarity	NPC83289
0.6667	Remote Similarity	NPC217277
0.6667	Remote Similarity	NPC258056
0.6645	Remote Similarity	NPC214869
0.6644	Remote Similarity	NPC218323
0.6642	Remote Similarity	NPC186469
0.6629	Remote Similarity	NPC301941
0.6629	Remote Similarity	NPC214188
0.6629	Remote Similarity	NPC246591
0.6629	Remote Similarity	NPC74618
0.6628	Remote Similarity	NPC225130
0.6623	Remote Similarity	NPC470706
0.6622	Remote Similarity	NPC213414
0.662	Remote Similarity	NPC317254
0.6619	Remote Similarity	NPC474149
0.6601	Remote Similarity	NPC6854
0.6601	Remote Similarity	NPC285078
0.6601	Remote Similarity	NPC313737
0.6599	Remote Similarity	NPC471314
0.6599	Remote Similarity	NPC471315
0.6594	Remote Similarity	NPC471495
0.6594	Remote Similarity	NPC96224
0.6594	Remote Similarity	NPC24101
0.6593	Remote Similarity	NPC178902
0.6593	Remote Similarity	NPC192596
0.6587	Remote Similarity	NPC22014
0.6579	Remote Similarity	NPC308885
0.6579	Remote Similarity	NPC255550
0.6579	Remote Similarity	NPC114102
0.6561	Remote Similarity	NPC471336
0.6561	Remote Similarity	NPC470746
0.6558	Remote Similarity	NPC473463
0.6556	Remote Similarity	NPC469977
0.6554	Remote Similarity	NPC13020
0.6554	Remote Similarity	NPC105999
0.6554	Remote Similarity	NPC140359
0.6536	Remote Similarity	NPC93882
0.6536	Remote Similarity	NPC82741
0.6536	Remote Similarity	NPC130595
0.6536	Remote Similarity	NPC141405
0.6536	Remote Similarity	NPC473409
0.6528	Remote Similarity	NPC120075
0.6522	Remote Similarity	NPC245974
0.6519	Remote Similarity	NPC51633
0.6519	Remote Similarity	NPC323204
0.6514	Remote Similarity	NPC290534
0.651	Remote Similarity	NPC236265
0.6507	Remote Similarity	NPC180207

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 NPC470470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	720
0.2-0.3	1284
0.3-0.4	2502
0.4-0.5	3055
0.5-0.6	1196
0.6-0.7	249
0.7-0.8	4
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
0.7403	Intermediate Similarity	NPD2183	Approved
0.7403	Intermediate Similarity	NPD2184	Approved
0.7095	Intermediate Similarity	NPD1423	Approved
0.7034	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1819	Approved
0.6918	Remote Similarity	NPD1817	Approved
0.6918	Remote Similarity	NPD1820	Approved
0.6918	Remote Similarity	NPD1818	Approved
0.6906	Remote Similarity	NPD595	Approved
0.6906	Remote Similarity	NPD593	Approved
0.6903	Remote Similarity	NPD2458	Approved
0.6903	Remote Similarity	NPD2459	Approved
0.6903	Remote Similarity	NPD2460	Phase 3
0.6899	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3166	Approved
0.6846	Remote Similarity	NPD3179	Approved
0.6846	Remote Similarity	NPD3167	Approved
0.6846	Remote Similarity	NPD3165	Approved
0.6846	Remote Similarity	NPD3164	Approved
0.6846	Remote Similarity	NPD5163	Phase 2
0.6846	Remote Similarity	NPD9718	Approved
0.6846	Remote Similarity	NPD3180	Approved
0.6842	Remote Similarity	NPD3052	Approved
0.6842	Remote Similarity	NPD3054	Approved
0.6824	Remote Similarity	NPD4993	Discontinued
0.68	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1009	Approved
0.6783	Remote Similarity	NPD3049	Approved
0.6781	Remote Similarity	NPD2429	Approved
0.6781	Remote Similarity	NPD2428	Approved
0.6736	Remote Similarity	NPD2556	Approved
0.6736	Remote Similarity	NPD2668	Approved
0.6736	Remote Similarity	NPD2667	Approved
0.6736	Remote Similarity	NPD2554	Approved
0.6731	Remote Similarity	NPD7153	Discontinued
0.673	Remote Similarity	NPD6087	Phase 1
0.671	Remote Similarity	NPD3156	Discontinued
0.6689	Remote Similarity	NPD1794	Approved
0.6687	Remote Similarity	NPD3985	Discontinued
0.6667	Remote Similarity	NPD1669	Approved
0.6667	Remote Similarity	NPD1411	Approved
0.6645	Remote Similarity	NPD6380	Phase 1
0.6645	Remote Similarity	NPD840	Approved
0.6645	Remote Similarity	NPD839	Approved
0.6643	Remote Similarity	NPD16	Approved
0.6643	Remote Similarity	NPD856	Approved
0.6643	Remote Similarity	NPD821	Approved
0.6623	Remote Similarity	NPD6179	Discontinued
0.66	Remote Similarity	NPD2250	Discontinued
0.6584	Remote Similarity	NPD2505	Approved
0.6584	Remote Similarity	NPD2504	Approved
0.6584	Remote Similarity	NPD6419	Discontinued
0.6584	Remote Similarity	NPD2874	Phase 2
0.6582	Remote Similarity	NPD3060	Approved
0.6579	Remote Similarity	NPD3145	Approved
0.6579	Remote Similarity	NPD1039	Discontinued
0.6579	Remote Similarity	NPD3144	Approved
0.6564	Remote Similarity	NPD5267	Discontinued
0.6545	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5481	Discontinued
0.6541	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2245	Discovery
0.6536	Remote Similarity	NPD3163	Approved
0.6536	Remote Similarity	NPD3162	Approved
0.6536	Remote Similarity	NPD2674	Phase 3
0.6533	Remote Similarity	NPD7451	Discontinued
0.6519	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2240	Approved
0.6497	Remote Similarity	NPD2239	Approved
0.6494	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2561	Approved
0.6486	Remote Similarity	NPD2230	Approved
0.6486	Remote Similarity	NPD2233	Approved
0.6486	Remote Similarity	NPD2232	Approved
0.6486	Remote Similarity	NPD2562	Approved
0.6486	Remote Similarity	NPD2235	Phase 2
0.6486	Remote Similarity	NPD2231	Phase 2
0.6478	Remote Similarity	NPD6364	Approved
0.6478	Remote Similarity	NPD44	Approved
0.6478	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4162	Approved
0.6458	Remote Similarity	NPD3596	Phase 2
0.645	Remote Similarity	NPD8031	Discontinued
0.6443	Remote Similarity	NPD6582	Phase 2
0.6443	Remote Similarity	NPD3685	Discontinued
0.6443	Remote Similarity	NPD6583	Phase 3
0.6443	Remote Similarity	NPD4129	Approved
0.6442	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD52	Approved
0.6442	Remote Similarity	NPD7526	Approved
0.6438	Remote Similarity	NPD6382	Discontinued
0.6429	Remote Similarity	NPD3530	Approved
0.6429	Remote Similarity	NPD3532	Approved
0.6429	Remote Similarity	NPD3531	Approved
0.6429	Remote Similarity	NPD5745	Approved
0.6425	Remote Similarity	NPD3336	Discovery
0.6414	Remote Similarity	NPD317	Approved
0.6414	Remote Similarity	NPD318	Approved
0.641	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7131	Phase 3
0.64	Remote Similarity	NPD5311	Approved
0.64	Remote Similarity	NPD5310	Approved
0.6392	Remote Similarity	NPD1725	Approved
0.638	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.638	Remote Similarity	NPD3536	Discontinued
0.6375	Remote Similarity	NPD5289	Phase 2
0.6369	Remote Similarity	NPD3553	Approved
0.6369	Remote Similarity	NPD3552	Approved
0.6369	Remote Similarity	NPD3554	Approved
0.6369	Remote Similarity	NPD3555	Approved
0.6364	Remote Similarity	NPD5718	Phase 2
0.6364	Remote Similarity	NPD592	Approved
0.6364	Remote Similarity	NPD594	Approved
0.6358	Remote Similarity	NPD3567	Approved
0.6358	Remote Similarity	NPD5756	Phase 2
0.6358	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD3568	Approved
0.6358	Remote Similarity	NPD4083	Discontinued
0.6352	Remote Similarity	NPD3656	Approved
0.6341	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.634	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD3560	Approved
0.6331	Remote Similarity	NPD3556	Approved
0.6331	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD3558	Approved
0.6331	Remote Similarity	NPD3557	Approved
0.6329	Remote Similarity	NPD2156	Approved
0.6329	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD1169	Approved
0.6329	Remote Similarity	NPD2155	Approved
0.6329	Remote Similarity	NPD2154	Approved
0.6329	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD2595	Approved
0.6327	Remote Similarity	NPD2594	Approved
0.6327	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD7477	Discontinued
0.6323	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7905	Discontinued
0.6316	Remote Similarity	NPD6584	Phase 3
0.631	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD2653	Approved
0.6306	Remote Similarity	NPD2157	Approved
0.6304	Remote Similarity	NPD9608	Approved
0.6304	Remote Similarity	NPD9610	Approved
0.6299	Remote Similarity	NPD5746	Approved
0.6299	Remote Similarity	NPD3136	Phase 2
0.6296	Remote Similarity	NPD3692	Discontinued
0.6291	Remote Similarity	NPD2922	Phase 1
0.6291	Remote Similarity	NPD196	Phase 1
0.6287	Remote Similarity	NPD3679	Phase 2
0.6286	Remote Similarity	NPD5373	Approved
0.6286	Remote Similarity	NPD5374	Approved
0.6282	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD1712	Approved
0.6259	Remote Similarity	NPD6581	Approved
0.6259	Remote Similarity	NPD2486	Discontinued
0.6259	Remote Similarity	NPD6580	Approved
0.6259	Remote Similarity	NPD316	Approved
0.625	Remote Similarity	NPD3053	Approved
0.625	Remote Similarity	NPD1135	Approved
0.625	Remote Similarity	NPD1133	Approved
0.625	Remote Similarity	NPD1131	Approved
0.625	Remote Similarity	NPD3055	Approved
0.625	Remote Similarity	NPD1134	Approved
0.625	Remote Similarity	NPD1129	Approved
0.625	Remote Similarity	NPD1232	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1035	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6072	Discontinued
0.625	Remote Similarity	NPD1318	Phase 2
0.6243	Remote Similarity	NPD7484	Phase 3
0.6243	Remote Similarity	NPD7485	Phase 3
0.6242	Remote Similarity	NPD3421	Phase 3
0.6242	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD2684	Approved
0.6235	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD600	Approved
0.6234	Remote Similarity	NPD596	Approved
0.6234	Remote Similarity	NPD2614	Approved
0.6228	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4108	Discontinued
0.622	Remote Similarity	NPD7598	Phase 2
0.622	Remote Similarity	NPD1786	Approved
0.622	Remote Similarity	NPD1785	Approved
0.622	Remote Similarity	NPD1787	Approved
0.6218	Remote Similarity	NPD6407	Approved
0.6218	Remote Similarity	NPD6405	Approved
0.6218	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD1798	Approved
0.6216	Remote Similarity	NPD1797	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