NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	566.27
Volume:	547.584
LogP:	0.467
LogD:	0.034
LogS:	-3.029
# Rotatable Bonds:	4
TPSA:	190.28
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.201
Synthetic Accessibility Score:	5.648
Fsp3:	0.828
Lipinski Rule-of-5:	Rejected
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:	-6.724
MDCK Permeability:	5.565508399740793e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.89
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.231
Plasma Protein Binding (PPB):	53.27521514892578%
Volume Distribution (VD):	0.464
Pgp-substrate:	30.610170364379883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.408
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	2.084
Half-life (T1/2):	0.575

ADMET: Toxicity

hERG Blockers:	0.24
Human Hepatotoxicity (H-HT):	0.407
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.655
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.427
Carcinogencity:	0.87
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC70485

Natural Product ID:	NPC70485
*Common Name:**	Purpuroine D
IUPAC Name:	(2R)-4-(2,4-dibromo-6-iodophenoxy)-2-(trimethylazaniumyl)butanoate
Synonyms:	Purpuroine D
Standard InCHIKey:	RVCDCTOZQNXIPD-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C13H16Br2INO3/c1-17(2,3)11(13(18)19)4-5-20-12-9(15)6-8(14)7-10(12)16/h6-7,11H,4-5H2,1-3H3/t11-/m1/s1
SMILES:	Brc1cc(Br)c(c(c1)I)OCC[C@@H]([N+](C)(C)C)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204068
PubChem CID:	71454035
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0002404] Alpha amino acids [CHEMONTID:0004145] D-alpha-amino acids

*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
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924179]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23131412]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	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
IC50	5

Activity Type	# Activity
Individual Protein	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[506516]
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	=	0.94	ug.mL-1	PMID[506516]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC50	=	25.56	ug.mL-1	PMID[506516]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	19.03	ug.mL-1	PMID[506516]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	=	1.45	ug.mL-1	PMID[506516]

☑ 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 NPC70485 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	203
0.1-0.2	4061
0.2-0.3	13794
0.3-0.4	8204
0.4-0.5	15116
0.5-0.6	1204
0.6-0.7	106
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC280736
0.96	High Similarity	NPC195902
0.8099	Intermediate Similarity	NPC142803
0.7817	Intermediate Similarity	NPC40321
0.7517	Intermediate Similarity	NPC470709
0.7338	Intermediate Similarity	NPC110131
0.7092	Intermediate Similarity	NPC124776
0.6984	Remote Similarity	NPC313918
0.6954	Remote Similarity	NPC308571
0.6917	Remote Similarity	NPC95977
0.6899	Remote Similarity	NPC319933
0.6871	Remote Similarity	NPC243404
0.6846	Remote Similarity	NPC470248
0.6846	Remote Similarity	NPC470249
0.6838	Remote Similarity	NPC221301
0.6788	Remote Similarity	NPC162294
0.6783	Remote Similarity	NPC272463
0.6774	Remote Similarity	NPC71629
0.6774	Remote Similarity	NPC296085
0.6755	Remote Similarity	NPC470250
0.6755	Remote Similarity	NPC128877
0.6739	Remote Similarity	NPC264379
0.6709	Remote Similarity	NPC47672
0.6688	Remote Similarity	NPC135349
0.6687	Remote Similarity	NPC233926
0.6643	Remote Similarity	NPC71186
0.6643	Remote Similarity	NPC116562
0.6541	Remote Similarity	NPC258222
0.6503	Remote Similarity	NPC170824
0.6488	Remote Similarity	NPC477255
0.6478	Remote Similarity	NPC76412
0.6471	Remote Similarity	NPC474673
0.6447	Remote Similarity	NPC235633
0.6443	Remote Similarity	NPC135173
0.6398	Remote Similarity	NPC469711
0.6369	Remote Similarity	NPC78530
0.6358	Remote Similarity	NPC470392
0.6345	Remote Similarity	NPC235166
0.6345	Remote Similarity	NPC88733
0.6345	Remote Similarity	NPC173511
0.634	Remote Similarity	NPC470471
0.6335	Remote Similarity	NPC109968
0.6294	Remote Similarity	NPC104124
0.628	Remote Similarity	NPC156311
0.6259	Remote Similarity	NPC230013
0.6259	Remote Similarity	NPC197576
0.6259	Remote Similarity	NPC68350
0.6259	Remote Similarity	NPC131940
0.6259	Remote Similarity	NPC81149
0.6258	Remote Similarity	NPC470470
0.625	Remote Similarity	NPC44270
0.625	Remote Similarity	NPC477254
0.625	Remote Similarity	NPC86007
0.6216	Remote Similarity	NPC1744
0.6216	Remote Similarity	NPC163019
0.6207	Remote Similarity	NPC180207
0.6207	Remote Similarity	NPC41232
0.6207	Remote Similarity	NPC63317
0.6203	Remote Similarity	NPC470247
0.6184	Remote Similarity	NPC11449
0.6176	Remote Similarity	NPC17537
0.6176	Remote Similarity	NPC473855
0.6174	Remote Similarity	NPC320242
0.6174	Remote Similarity	NPC136112
0.6174	Remote Similarity	NPC141739
0.6165	Remote Similarity	NPC307039
0.6165	Remote Similarity	NPC132725
0.6164	Remote Similarity	NPC153580
0.6164	Remote Similarity	NPC56634
0.6164	Remote Similarity	NPC226737
0.6164	Remote Similarity	NPC47769
0.6164	Remote Similarity	NPC299939
0.6164	Remote Similarity	NPC196371
0.6145	Remote Similarity	NPC80337
0.6131	Remote Similarity	NPC176971
0.6122	Remote Similarity	NPC137922
0.6122	Remote Similarity	NPC40302
0.6103	Remote Similarity	NPC283546
0.6089	Remote Similarity	NPC8093
0.6089	Remote Similarity	NPC121571
0.6087	Remote Similarity	NPC157473
0.6087	Remote Similarity	NPC151530
0.6081	Remote Similarity	NPC25134
0.6081	Remote Similarity	NPC97157
0.6081	Remote Similarity	NPC64130
0.6081	Remote Similarity	NPC175520
0.6081	Remote Similarity	NPC295879
0.6081	Remote Similarity	NPC159866
0.6077	Remote Similarity	NPC230539
0.6069	Remote Similarity	NPC191194
0.6062	Remote Similarity	NPC470472
0.6058	Remote Similarity	NPC128730
0.6051	Remote Similarity	NPC213471
0.6044	Remote Similarity	NPC248822
0.6033	Remote Similarity	NPC475843
0.6014	Remote Similarity	NPC41594
0.6014	Remote Similarity	NPC474375
0.6013	Remote Similarity	NPC317741
0.6013	Remote Similarity	NPC318984
0.6013	Remote Similarity	NPC197239
0.6013	Remote Similarity	NPC326860
0.6013	Remote Similarity	NPC282087
0.6013	Remote Similarity	NPC259800
0.6013	Remote Similarity	NPC241086
0.6013	Remote Similarity	NPC318028
0.6013	Remote Similarity	NPC328137
0.6011	Remote Similarity	NPC64066
0.6	Remote Similarity	NPC107101
0.6	Remote Similarity	NPC77435
0.6	Remote Similarity	NPC259071
0.5987	Remote Similarity	NPC78061
0.5987	Remote Similarity	NPC122359
0.5987	Remote Similarity	NPC159987
0.5978	Remote Similarity	NPC474678
0.5978	Remote Similarity	NPC471338
0.5976	Remote Similarity	NPC214239
0.5974	Remote Similarity	NPC178301
0.5956	Remote Similarity	NPC307425
0.5944	Remote Similarity	NPC26524
0.5942	Remote Similarity	NPC238115
0.5942	Remote Similarity	NPC473393
0.5938	Remote Similarity	NPC204546
0.5935	Remote Similarity	NPC274732
0.5935	Remote Similarity	NPC247018
0.5935	Remote Similarity	NPC307123
0.5935	Remote Similarity	NPC97870
0.5935	Remote Similarity	NPC259017
0.5935	Remote Similarity	NPC474753
0.5929	Remote Similarity	NPC291837
0.5924	Remote Similarity	NPC102245
0.5921	Remote Similarity	NPC45728
0.5918	Remote Similarity	NPC234956
0.5912	Remote Similarity	NPC179686
0.5906	Remote Similarity	NPC23837
0.5899	Remote Similarity	NPC326447
0.5894	Remote Similarity	NPC236265
0.5887	Remote Similarity	NPC259554
0.5878	Remote Similarity	NPC318429
0.5868	Remote Similarity	NPC235033
0.5868	Remote Similarity	NPC471235
0.5868	Remote Similarity	NPC73132
0.586	Remote Similarity	NPC303993
0.585	Remote Similarity	NPC159916
0.585	Remote Similarity	NPC293424
0.5847	Remote Similarity	NPC147847
0.5845	Remote Similarity	NPC88868
0.5845	Remote Similarity	NPC231251
0.5845	Remote Similarity	NPC25067
0.5844	Remote Similarity	NPC283079
0.5839	Remote Similarity	NPC474128
0.5828	Remote Similarity	NPC255253
0.5828	Remote Similarity	NPC105999
0.5814	Remote Similarity	NPC252149
0.5811	Remote Similarity	NPC98748
0.5806	Remote Similarity	NPC206183
0.5806	Remote Similarity	NPC227953
0.5806	Remote Similarity	NPC222684
0.5795	Remote Similarity	NPC90245
0.5793	Remote Similarity	NPC189908
0.5792	Remote Similarity	NPC174607
0.5789	Remote Similarity	NPC471337
0.5789	Remote Similarity	NPC473450
0.5789	Remote Similarity	NPC213414
0.5787	Remote Similarity	NPC143450
0.5787	Remote Similarity	NPC475976
0.5786	Remote Similarity	NPC307682
0.5786	Remote Similarity	NPC1065
0.5781	Remote Similarity	NPC125306
0.5775	Remote Similarity	NPC149545
0.5775	Remote Similarity	NPC202866
0.5772	Remote Similarity	NPC193193
0.5772	Remote Similarity	NPC31314
0.5767	Remote Similarity	NPC81026
0.576	Remote Similarity	NPC124576
0.5755	Remote Similarity	NPC109637
0.575	Remote Similarity	NPC318591
0.575	Remote Similarity	NPC231163
0.5733	Remote Similarity	NPC322569
0.5725	Remote Similarity	NPC51633
0.5724	Remote Similarity	NPC328267
0.5724	Remote Similarity	NPC320287
0.5723	Remote Similarity	NPC472923
0.5723	Remote Similarity	NPC196708
0.5722	Remote Similarity	NPC475120
0.5714	Remote Similarity	NPC33717
0.5714	Remote Similarity	NPC186617
0.5707	Remote Similarity	NPC123140
0.5706	Remote Similarity	NPC266741
0.5705	Remote Similarity	NPC256369
0.5695	Remote Similarity	NPC26285
0.5694	Remote Similarity	NPC233238
0.5694	Remote Similarity	NPC245552
0.5693	Remote Similarity	NPC471576
0.5685	Remote Similarity	NPC87563
0.5685	Remote Similarity	NPC235250
0.5683	Remote Similarity	NPC192596
0.5682	Remote Similarity	NPC473693
0.5682	Remote Similarity	NPC471568
0.568	Remote Similarity	NPC470710
0.5679	Remote Similarity	NPC81137

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 NPC70485 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	910
0.2-0.3	2356
0.3-0.4	3026
0.4-0.5	2073
0.5-0.6	598
0.6-0.7	42
0.7-0.8	0
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
0.6917	Remote Similarity	NPD2671	Approved
0.6917	Remote Similarity	NPD2673	Approved
0.6853	Remote Similarity	NPD1318	Phase 2
0.6781	Remote Similarity	NPD5746	Approved
0.6692	Remote Similarity	NPD5373	Approved
0.6692	Remote Similarity	NPD5374	Approved
0.6689	Remote Similarity	NPD5745	Approved
0.6623	Remote Similarity	NPD5689	Approved
0.6623	Remote Similarity	NPD5688	Approved
0.6622	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6032	Approved
0.649	Remote Similarity	NPD4618	Approved
0.649	Remote Similarity	NPD4622	Approved
0.6479	Remote Similarity	NPD1798	Approved
0.6479	Remote Similarity	NPD1797	Approved
0.6429	Remote Similarity	NPD2239	Approved
0.6429	Remote Similarity	NPD2240	Approved
0.6419	Remote Similarity	NPD2237	Approved
0.6338	Remote Similarity	NPD1102	Approved
0.6338	Remote Similarity	NPD1103	Approved
0.6306	Remote Similarity	NPD4487	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD9718	Approved
0.6225	Remote Similarity	NPD5163	Phase 2
0.6224	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD1393	Approved
0.6204	Remote Similarity	NPD9624	Approved
0.6197	Remote Similarity	NPD2557	Approved
0.6181	Remote Similarity	NPD7534	Approved
0.6181	Remote Similarity	NPD7533	Approved
0.6174	Remote Similarity	NPD1818	Approved
0.6174	Remote Similarity	NPD1820	Approved
0.6174	Remote Similarity	NPD1819	Approved
0.6174	Remote Similarity	NPD1817	Approved
0.6174	Remote Similarity	NPD1794	Approved
0.6164	Remote Similarity	NPD3447	Discontinued
0.6159	Remote Similarity	NPD2052	Approved
0.6154	Remote Similarity	NPD3596	Phase 2
0.6144	Remote Similarity	NPD4870	Approved
0.6138	Remote Similarity	NPD2595	Approved
0.6138	Remote Similarity	NPD2594	Approved
0.6133	Remote Similarity	NPD7018	Phase 2
0.6121	Remote Similarity	NPD22	Approved
0.6121	Remote Similarity	NPD2053	Approved
0.609	Remote Similarity	NPD1520	Approved
0.609	Remote Similarity	NPD1536	Approved
0.609	Remote Similarity	NPD1521	Approved
0.6084	Remote Similarity	NPD2513	Approved
0.6074	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD6581	Approved
0.6069	Remote Similarity	NPD6580	Approved
0.6056	Remote Similarity	NPD592	Approved
0.6056	Remote Similarity	NPD594	Approved
0.6048	Remote Similarity	NPD3007	Approved
0.6048	Remote Similarity	NPD2515	Approved
0.6038	Remote Similarity	NPD2897	Discontinued
0.6027	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD6382	Discontinued
0.6026	Remote Similarity	NPD2987	Approved
0.6026	Remote Similarity	NPD2990	Approved
0.6013	Remote Similarity	NPD3167	Approved
0.6013	Remote Similarity	NPD1538	Phase 1
0.6013	Remote Similarity	NPD1537	Approved
0.6013	Remote Similarity	NPD1522	Approved
0.6013	Remote Similarity	NPD3164	Approved
0.6013	Remote Similarity	NPD1523	Approved
0.6013	Remote Similarity	NPD3180	Approved
0.6013	Remote Similarity	NPD3179	Approved
0.6013	Remote Similarity	NPD4476	Approved
0.6013	Remote Similarity	NPD1519	Approved
0.6013	Remote Similarity	NPD3165	Approved
0.6013	Remote Similarity	NPD3166	Approved
0.6013	Remote Similarity	NPD4477	Approved
0.5987	Remote Similarity	NPD2250	Discontinued
0.5987	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD2496	Approved
0.5986	Remote Similarity	NPD2497	Approved
0.5976	Remote Similarity	NPD2676	Approved
0.5976	Remote Similarity	NPD2675	Approved
0.5976	Remote Similarity	NPD2183	Approved
0.5976	Remote Similarity	NPD2184	Approved
0.596	Remote Similarity	NPD4098	Discontinued
0.596	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD1894	Discontinued
0.5946	Remote Similarity	NPD155	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD1423	Approved
0.5935	Remote Similarity	NPD2245	Discovery
0.5933	Remote Similarity	NPD6583	Phase 3
0.5933	Remote Similarity	NPD6582	Phase 2
0.5924	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5585	Approved
0.5918	Remote Similarity	NPD3445	Approved
0.5918	Remote Similarity	NPD3443	Approved
0.5918	Remote Similarity	NPD3444	Approved
0.5901	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD3134	Approved
0.5897	Remote Similarity	NPD3142	Approved
0.5897	Remote Similarity	NPD3140	Approved
0.5897	Remote Similarity	NPD756	Suspended
0.5894	Remote Similarity	NPD196	Phase 1
0.5893	Remote Similarity	NPD6677	Suspended
0.589	Remote Similarity	NPD6667	Approved
0.589	Remote Similarity	NPD6666	Approved
0.5882	Remote Similarity	NPD4993	Discontinued
0.5878	Remote Similarity	NPD2556	Approved
0.5878	Remote Similarity	NPD1010	Approved
0.5878	Remote Similarity	NPD9365	Approved
0.5878	Remote Similarity	NPD2554	Approved
0.5875	Remote Similarity	NPD3656	Approved
0.5874	Remote Similarity	NPD769	Approved
0.5871	Remote Similarity	NPD1048	Approved
0.5871	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD1358	Approved
0.5854	Remote Similarity	NPD2114	Discontinued
0.5844	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD7131	Phase 3
0.5833	Remote Similarity	NPD3162	Approved
0.5833	Remote Similarity	NPD3163	Approved
0.5828	Remote Similarity	NPD6540	Phase 3
0.5828	Remote Similarity	NPD6539	Approved
0.5828	Remote Similarity	NPD1420	Approved
0.5828	Remote Similarity	NPD6543	Approved
0.5828	Remote Similarity	NPD6542	Approved
0.5828	Remote Similarity	NPD1421	Approved
0.5822	Remote Similarity	NPD5291	Approved
0.5822	Remote Similarity	NPD5292	Approved
0.5818	Remote Similarity	NPD3146	Approved
0.5818	Remote Similarity	NPD3536	Discontinued
0.5818	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD6584	Phase 3
0.5813	Remote Similarity	NPD1725	Approved
0.5811	Remote Similarity	NPD3049	Approved
0.58	Remote Similarity	NPD776	Approved
0.5796	Remote Similarity	NPD2203	Discontinued
0.5796	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.5796	Remote Similarity	NPD4101	Phase 1
0.5793	Remote Similarity	NPD595	Approved
0.5793	Remote Similarity	NPD593	Approved
0.5789	Remote Similarity	NPD6541	Approved
0.5789	Remote Similarity	NPD6538	Approved
0.5786	Remote Similarity	NPD2200	Suspended
0.5772	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD1778	Approved
0.5767	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD5356	Approved
0.5765	Remote Similarity	NPD5355	Approved
0.575	Remote Similarity	NPD2155	Approved
0.575	Remote Similarity	NPD2154	Approved
0.575	Remote Similarity	NPD2156	Approved
0.5743	Remote Similarity	NPD2486	Discontinued
0.5741	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD4475	Approved
0.5732	Remote Similarity	NPD3532	Approved
0.5732	Remote Similarity	NPD3530	Approved
0.5732	Remote Similarity	NPD3531	Approved
0.5732	Remote Similarity	NPD4474	Approved
0.5731	Remote Similarity	NPD7972	Discontinued
0.5724	Remote Similarity	NPD2428	Approved
0.5724	Remote Similarity	NPD4359	Approved
0.5724	Remote Similarity	NPD2429	Approved
0.5724	Remote Similarity	NPD3685	Discontinued
0.5723	Remote Similarity	NPD3052	Approved
0.5723	Remote Similarity	NPD2224	Approved
0.5723	Remote Similarity	NPD2653	Approved
0.5723	Remote Similarity	NPD3054	Approved
0.5723	Remote Similarity	NPD2223	Approved
0.5714	Remote Similarity	NPD1422	Approved
0.5714	Remote Similarity	NPD3687	Approved
0.5714	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3686	Approved
0.5706	Remote Similarity	NPD5890	Approved
0.5706	Remote Similarity	NPD6386	Approved
0.5706	Remote Similarity	NPD6385	Approved
0.5706	Remote Similarity	NPD5889	Approved
0.5698	Remote Similarity	NPD5353	Approved
0.5697	Remote Similarity	NPD5295	Discontinued
0.5695	Remote Similarity	NPD1535	Discovery
0.5691	Remote Similarity	NPD1298	Discontinued
0.5689	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD6808	Phase 2
0.568	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.568	Remote Similarity	NPD2649	Approved
0.568	Remote Similarity	NPD2651	Approved
0.5677	Remote Similarity	NPD455	Discontinued
0.5673	Remote Similarity	NPD6280	Approved
0.5673	Remote Similarity	NPD6279	Approved
0.5669	Remote Similarity	NPD7294	Phase 1
0.5669	Remote Similarity	NPD1336	Approved
0.5667	Remote Similarity	NPD2667	Approved
0.5667	Remote Similarity	NPD2668	Approved
0.5664	Remote Similarity	NPD5240	Approved
0.5664	Remote Similarity	NPD556	Approved
0.5664	Remote Similarity	NPD5236	Approved
0.5664	Remote Similarity	NPD5239	Approved
0.5664	Remote Similarity	NPD5237	Approved
0.5664	Remote Similarity	NPD5235	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