NPASS Compound

Structure

NPC476408 OpenBabel07101719522D 32 35 0 0 1 0 0 0 0 0999 V2000 6.6962 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0516 -2.8840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4320 -5.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6667 -4.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.3660 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.4757 -5.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7847 -6.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1449 -4.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.7629 -6.5657 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.1230 -4.8715 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.1156 -7.1009 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6449 -3.7976 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 7.5622 -5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.4246 -8.0520 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 2 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 30 1 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 31 1 0 0 0 0 16 27 2 0 0 0 0 16 28 1 0 0 0 0 17 30 2 0 0 0 0 17 31 1 0 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 23 29 1 0 0 0 0 24 28 2 0 0 0 0 24 30 1 0 0 0 0 29 32 1 0 0 0 0 M CHG 2 30 1 32 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	437.32
Volume:	471.982
LogP:	4.282
LogD:	5.335
LogS:	-4.426
# Rotatable Bonds:	5
TPSA:	72.91
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.401
Synthetic Accessibility Score:	5.019
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.212
MDCK Permeability:	6.1399268815875985e-06
Pgp-inhibitor:	0.158
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.64
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.268
Plasma Protein Binding (PPB):	76.81441497802734%
Volume Distribution (VD):	1.323
Pgp-substrate:	31.360248565673828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.217
CYP2C19-inhibitor:	0.272
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.772
CYP2D6-inhibitor:	0.931
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.7
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	5.475
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.889
Drug-inuced Liver Injury (DILI):	0.12
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.623
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.052
Carcinogencity:	0.031
Eye Corrosion:	0.004
Eye Irritation:	0.105
Respiratory Toxicity:	0.816

Download Data

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

Natural Product: NPC476408

Natural Product ID:	NPC476408
*Common Name:**	QDOMHYWIMJTPLY-ZHZNLTMTSA-N
IUPAC Name:	n.a.
Synonyms:	Ageloxime-D
Standard InCHIKey:	QDOMHYWIMJTPLY-ZHZNLTMTSA-N
Standard InCHI:	InChI=1S/C26H39N5O.ClH/c1-18(12-15-31-17-30(6)24-22(31)23(29-32)27-16-28-24)8-10-20-19(2)9-11-21-25(3,4)13-7-14-26(20,21)5;/h12,16-17,20-21H,2,7-11,13-15H2,1,3-6H3,(H-,27,28,29,32);1H/b18-12+;/t20-,21-,26+;/m1./s1
SMILES:	[O-]Nc1ncnc2c1n(C/C=C(/CC[C@@H]1C(=C)CC[C@H]3[C@@]1(C)CCCC3(C)C)C)c[n+]2C.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL597102
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO33334	agelas sponges	Species	Agelasidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[20061160]

☑ 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	1
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	4.2	%	PMID[491851]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	12500.0	nM	PMID[491851]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	45000.0	nM	PMID[491851]

☑ 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 NPC476408 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	841
0.1-0.2	17040
0.2-0.3	19098
0.3-0.4	3635
0.4-0.5	1753
0.5-0.6	282
0.6-0.7	23
0.7-0.8	6
0.8-0.85	4
0.85-0.9	5
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC476433
0.9701	High Similarity	NPC476528
0.9485	High Similarity	NPC476013
0.9485	High Similarity	NPC476522
0.9485	High Similarity	NPC474986
0.9478	High Similarity	NPC296437
0.9416	High Similarity	NPC476521
0.9407	High Similarity	NPC470266
0.9343	High Similarity	NPC476520
0.8811	High Similarity	NPC244700
0.8725	High Similarity	NPC18308
0.8725	High Similarity	NPC472832
0.8707	High Similarity	NPC472834
0.8649	High Similarity	NPC472833
0.8472	Intermediate Similarity	NPC89139
0.8276	Intermediate Similarity	NPC217656
0.7927	Intermediate Similarity	NPC473585
0.7738	Intermediate Similarity	NPC265111
0.7059	Intermediate Similarity	NPC317054
0.694	Remote Similarity	NPC87981
0.694	Remote Similarity	NPC174114
0.6903	Remote Similarity	NPC167285
0.6795	Remote Similarity	NPC226184
0.6795	Remote Similarity	NPC76544
0.6776	Remote Similarity	NPC57279
0.6629	Remote Similarity	NPC164845
0.6547	Remote Similarity	NPC476564
0.6429	Remote Similarity	NPC104011
0.6429	Remote Similarity	NPC18335
0.6352	Remote Similarity	NPC33996
0.6319	Remote Similarity	NPC4837
0.6319	Remote Similarity	NPC312187
0.6312	Remote Similarity	NPC129756
0.6294	Remote Similarity	NPC239737
0.6284	Remote Similarity	NPC68938
0.6173	Remote Similarity	NPC317821
0.6131	Remote Similarity	NPC150853
0.6129	Remote Similarity	NPC313514
0.6115	Remote Similarity	NPC246193
0.6111	Remote Similarity	NPC313897
0.6105	Remote Similarity	NPC93365
0.6082	Remote Similarity	NPC469308
0.6074	Remote Similarity	NPC209525
0.6074	Remote Similarity	NPC161659
0.6044	Remote Similarity	NPC477119
0.6012	Remote Similarity	NPC476219
0.6	Remote Similarity	NPC314152
0.6	Remote Similarity	NPC229974
0.5988	Remote Similarity	NPC189068
0.5988	Remote Similarity	NPC469975
0.596	Remote Similarity	NPC189314
0.5952	Remote Similarity	NPC309832
0.5952	Remote Similarity	NPC219313
0.5932	Remote Similarity	NPC225018
0.5928	Remote Similarity	NPC21448
0.5928	Remote Similarity	NPC156461
0.5928	Remote Similarity	NPC107374
0.592	Remote Similarity	NPC476297
0.5909	Remote Similarity	NPC300238
0.5897	Remote Similarity	NPC248007
0.5893	Remote Similarity	NPC164665
0.5882	Remote Similarity	NPC136349
0.5858	Remote Similarity	NPC269827
0.5851	Remote Similarity	NPC477118
0.5843	Remote Similarity	NPC470203
0.5829	Remote Similarity	NPC120070
0.5824	Remote Similarity	NPC121222
0.582	Remote Similarity	NPC477120
0.5815	Remote Similarity	NPC189261
0.5814	Remote Similarity	NPC470111
0.5814	Remote Similarity	NPC114209
0.5814	Remote Similarity	NPC161224
0.5795	Remote Similarity	NPC195140
0.5787	Remote Similarity	NPC158055
0.5787	Remote Similarity	NPC470204
0.578	Remote Similarity	NPC328479
0.5753	Remote Similarity	NPC476099
0.5747	Remote Similarity	NPC212551
0.5747	Remote Similarity	NPC302778
0.5723	Remote Similarity	NPC85689
0.5723	Remote Similarity	NPC211025
0.5723	Remote Similarity	NPC185991
0.5714	Remote Similarity	NPC174802
0.5714	Remote Similarity	NPC8590
0.5714	Remote Similarity	NPC108011
0.5705	Remote Similarity	NPC139776
0.5694	Remote Similarity	NPC250178
0.569	Remote Similarity	NPC472816
0.569	Remote Similarity	NPC321814
0.5682	Remote Similarity	NPC224076
0.5678	Remote Similarity	NPC276373
0.5657	Remote Similarity	NPC130586
0.5657	Remote Similarity	NPC164952
0.5652	Remote Similarity	NPC14330
0.565	Remote Similarity	NPC226245
0.565	Remote Similarity	NPC5802
0.5632	Remote Similarity	NPC24589
0.5631	Remote Similarity	NPC471603
0.5628	Remote Similarity	NPC290959
0.5622	Remote Similarity	NPC157821
0.5617	Remote Similarity	NPC287876
0.5616	Remote Similarity	NPC476561
0.5611	Remote Similarity	NPC122141
0.5602	Remote Similarity	NPC115595
0.56	Remote Similarity	NPC207633

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 NPC476408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	1074
0.2-0.3	3205
0.3-0.4	2252
0.4-0.5	1597
0.5-0.6	617
0.6-0.7	63
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
0.7181	Intermediate Similarity	NPD1058	Discontinued
0.6905	Remote Similarity	NPD1313	Approved
0.6627	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7158	Phase 1
0.6623	Remote Similarity	NPD870	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1333	Phase 3
0.6595	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4902	Discontinued
0.6517	Remote Similarity	NPD5962	Phase 2
0.6494	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD1015	Phase 2
0.6491	Remote Similarity	NPD1016	Phase 2
0.649	Remote Similarity	NPD9408	Phase 3
0.6486	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1215	Discontinued
0.6471	Remote Similarity	NPD9633	Phase 3
0.6461	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4240	Approved
0.645	Remote Similarity	NPD2927	Phase 3
0.6429	Remote Similarity	NPD8836	Approved
0.6429	Remote Similarity	NPD248	Discontinued
0.6416	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD2456	Phase 2
0.6409	Remote Similarity	NPD2457	Phase 2
0.6406	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6129	Phase 2
0.6379	Remote Similarity	NPD6794	Approved
0.6378	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6816	Phase 3
0.6344	Remote Similarity	NPD4615	Phase 2
0.6344	Remote Similarity	NPD7722	Suspended
0.6343	Remote Similarity	NPD2333	Discontinued
0.6333	Remote Similarity	NPD5508	Phase 1
0.6322	Remote Similarity	NPD8120	Approved
0.6322	Remote Similarity	NPD8121	Phase 3
0.6313	Remote Similarity	NPD7111	Discontinued
0.6292	Remote Similarity	NPD3799	Suspended
0.6292	Remote Similarity	NPD7006	Approved
0.629	Remote Similarity	NPD6761	Discontinued
0.6289	Remote Similarity	NPD7323	Phase 2
0.6286	Remote Similarity	NPD2647	Phase 3
0.6278	Remote Similarity	NPD5730	Phase 2
0.6278	Remote Similarity	NPD40	Phase 2
0.6276	Remote Similarity	NPD3860	Discontinued
0.6273	Remote Similarity	NPD3696	Approved
0.6273	Remote Similarity	NPD3695	Approved
0.6272	Remote Similarity	NPD2524	Discontinued
0.6266	Remote Similarity	NPD4763	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4352	Phase 1
0.6257	Remote Similarity	NPD6619	Phase 3
0.6257	Remote Similarity	NPD3431	Approved
0.6257	Remote Similarity	NPD3430	Approved
0.625	Remote Similarity	NPD799	Phase 1
0.625	Remote Similarity	NPD6721	Phase 1
0.625	Remote Similarity	NPD2793	Discontinued
0.625	Remote Similarity	NPD2591	Phase 2
0.6236	Remote Similarity	NPD5996	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5463	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4568	Phase 2
0.6222	Remote Similarity	NPD3041	Approved
0.622	Remote Similarity	NPD171	Discontinued
0.6211	Remote Similarity	NPD5462	Discontinued
0.6209	Remote Similarity	NPD2523	Phase 2
0.6209	Remote Similarity	NPD2526	Phase 2
0.6199	Remote Similarity	NPD5969	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD6469	Phase 3
0.6178	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD2451	Phase 2
0.6173	Remote Similarity	NPD2452	Phase 2
0.6173	Remote Similarity	NPD7445	Phase 1
0.6173	Remote Similarity	NPD2453	Phase 2
0.6173	Remote Similarity	NPD2450	Phase 2
0.617	Remote Similarity	NPD6577	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6192	Phase 3
0.6154	Remote Similarity	NPD5012	Phase 2
0.6145	Remote Similarity	NPD5324	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD4612	Discontinued
0.6136	Remote Similarity	NPD3889	Approved
0.6129	Remote Similarity	NPD7138	Phase 2
0.6127	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD2876	Phase 3
0.612	Remote Similarity	NPD1637	Clinical (unspecified phase)
0.612	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD3107	Discontinued
0.6117	Remote Similarity	NPD6849	Phase 2
0.6117	Remote Similarity	NPD6850	Phase 2
0.6111	Remote Similarity	NPD7297	Phase 2
0.6108	Remote Similarity	NPD4182	Phase 3
0.6108	Remote Similarity	NPD4183	Phase 3
0.6105	Remote Similarity	NPD546	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD2646	Discontinued
0.6102	Remote Similarity	NPD4213	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD1892	Phase 2
0.6099	Remote Similarity	NPD3409	Phase 1
0.6099	Remote Similarity	NPD1893	Phase 2
0.6089	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6828	Phase 2
0.6087	Remote Similarity	NPD4441	Phase 2
0.6085	Remote Similarity	NPD2839	Phase 2
0.6082	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6151	Phase 2
0.6077	Remote Similarity	NPD5943	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD5843	Discontinued
0.6077	Remote Similarity	NPD2406	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5684	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5683	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5682	Phase 3
0.6074	Remote Similarity	NPD193	Suspended
0.6073	Remote Similarity	NPD3362	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD2818	Discontinued
0.6061	Remote Similarity	NPD6521	Phase 3
0.6061	Remote Similarity	NPD6520	Phase 3
0.6061	Remote Similarity	NPD2824	Phase 2
0.605	Remote Similarity	NPD4863	Approved
0.6045	Remote Similarity	NPD509	Phase 3
0.6043	Remote Similarity	NPD6418	Phase 1
0.6042	Remote Similarity	NPD3830	Phase 1
0.6036	Remote Similarity	NPD3708	Phase 2
0.602	Remote Similarity	NPD2364	Suspended
0.6019	Remote Similarity	NPD4854	Phase 3
0.6011	Remote Similarity	NPD7504	Discontinued
0.601	Remote Similarity	NPD5885	Approved
0.601	Remote Similarity	NPD3905	Phase 3
0.6	Remote Similarity	NPD185	Approved
0.6	Remote Similarity	NPD4142	Discontinued
0.5989	Remote Similarity	NPD5642	Approved
0.5989	Remote Similarity	NPD2963	Phase 1
0.5988	Remote Similarity	NPD3612	Phase 2
0.5988	Remote Similarity	NPD1257	Approved
0.5981	Remote Similarity	NPD6352	Phase 2
0.5979	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4716	Approved
0.5978	Remote Similarity	NPD702	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD1690	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD306	Approved
0.5969	Remote Similarity	NPD5486	Discontinued
0.5966	Remote Similarity	NPD1288	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD174	Discontinued
0.596	Remote Similarity	NPD8833	Approved
0.596	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.596	Remote Similarity	NPD8831	Approved
0.596	Remote Similarity	NPD6271	Approved
0.5959	Remote Similarity	NPD2880	Discontinued
0.5957	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7988	Suspended
0.5951	Remote Similarity	NPD6470	Phase 3
0.5947	Remote Similarity	NPD7709	Discontinued
0.5946	Remote Similarity	NPD4744	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7164	Discontinued
0.5941	Remote Similarity	NPD2902	Phase 2
0.5941	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD418	Approved
0.593	Remote Similarity	NPD1030	Approved
0.593	Remote Similarity	NPD1027	Approved
0.593	Remote Similarity	NPD1029	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD166	Approved
0.5928	Remote Similarity	NPD250	Approved
0.5928	Remote Similarity	NPD249	Approved
0.5924	Remote Similarity	NPD3432	Approved
0.592	Remote Similarity	NPD4990	Clinical (unspecified phase)
0.592	Remote Similarity	NPD3405	Phase 3
0.5909	Remote Similarity	NPD7103	Approved
0.5907	Remote Similarity	NPD7935	Phase 2
0.5907	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD5757	Discontinued
0.5897	Remote Similarity	NPD9084	Phase 2
0.5896	Remote Similarity	NPD2128	Phase 1
0.5892	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD3265	Phase 1
0.5888	Remote Similarity	NPD2879	Approved
0.5888	Remote Similarity	NPD2881	Approved
0.5888	Remote Similarity	NPD2807	Discontinued
0.5882	Remote Similarity	NPD2318	Discontinued
0.5882	Remote Similarity	NPD548	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD5458	Discontinued
0.5873	Remote Similarity	NPD7394	Phase 2
0.587	Remote Similarity	NPD2731	Phase 2
0.587	Remote Similarity	NPD4155	Approved
0.5869	Remote Similarity	NPD8004	Discontinued
0.5868	Remote Similarity	NPD9704	Approved
0.5868	Remote Similarity	NPD3706	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD1658	Discontinued
0.5864	Remote Similarity	NPD9484	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD1303	Phase 1
0.5862	Remote Similarity	NPD3906	Approved
0.586	Remote Similarity	NPD1895	Discontinued
0.586	Remote Similarity	NPD1674	Clinical (unspecified phase)
0.586	Remote Similarity	NPD1675	Phase 1
0.5858	Remote Similarity	NPD195	Approved
0.5858	Remote Similarity	NPD186	Discovery

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