NPASS Compound

Structure

NPC230539 OpenBabel07101718312D 24 26 0 0 1 0 0 0 0 0999 V2000 1.1723 2.7058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1756 3.3501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6756 2.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6756 0.7520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6756 0.7520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6756 2.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 2.4271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3633 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1756 -0.1140 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.1756 1.6180 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.3633 2.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8968 3.3781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1723 0.5302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1756 3.3501 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 24 1 0 0 0 0 12 20 1 0 0 0 0 12 21 2 0 0 0 0 13 14 1 0 0 0 0 13 16 1 1 0 0 0 14 19 1 0 0 0 0 14 22 1 1 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 15 23 2 0 0 0 0 16 5 1 6 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	459.96
Volume:	342.162
LogP:	2.063
LogD:	1.664
LogS:	-3.879
# Rotatable Bonds:	2
TPSA:	70.08
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	4.626
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.703
MDCK Permeability:	1.8583921701065265e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.586
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	89.85320281982422%
Volume Distribution (VD):	1.028
Pgp-substrate:	19.970550537109375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.81
CYP2C19-inhibitor:	0.193
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.526
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	2.958
Half-life (T1/2):	0.349

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.319
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.203
Carcinogencity:	0.425
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.005

Download Data

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

Natural Product: NPC230539

Natural Product ID:	NPC230539
*Common Name:**	Amathaspiramide B
IUPAC Name:	(5S,8R,9R)-9-(2,4-dibromo-5-methoxyphenyl)-8-hydroxy-1,7-dimethyl-1,7-diazaspiro[4.4]nonane-2,6-dione
Synonyms:
Standard InCHIKey:	MLOALGRVDHEDCC-LZWOXQAQSA-N
Standard InCHI:	InChI=1S/C16H18Br2N2O4/c1-19-14(22)13(8-6-11(24-3)10(18)7-9(8)17)16(15(19)23)5-4-12(21)20(16)2/h6-7,13-14,22H,4-5H2,1-3H3/t13-,14+,16-/m0/s1
SMILES:	COc1cc(c(cc1Br)Br)[C@H]1[C@@H](O)N(C(=O)[C@@]21CCC(=O)N2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491701
PubChem CID:	10671715
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000218] Pyrrolidines [CHEMONTID:0002336] Phenylpyrrolidines

*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
NPO3299	Amathia wilsoni	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346946]
NPO3299	Amathia wilsoni	Species	Vesiculariidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	12.5	ug.mL-1	PMID[514805]

☑ 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 NPC230539 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	289
0.1-0.2	1469
0.2-0.3	7566
0.3-0.4	11037
0.4-0.5	17073
0.5-0.6	4860
0.6-0.7	393
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC80337
0.9538	High Similarity	NPC64066
0.9096	High Similarity	NPC102245
0.731	Intermediate Similarity	NPC470248
0.7225	Intermediate Similarity	NPC470250
0.7209	Intermediate Similarity	NPC470249
0.7052	Intermediate Similarity	NPC235633
0.6866	Remote Similarity	NPC473941
0.6853	Remote Similarity	NPC102760
0.6834	Remote Similarity	NPC147847
0.6816	Remote Similarity	NPC470247
0.6798	Remote Similarity	NPC470709
0.6784	Remote Similarity	NPC174607
0.6782	Remote Similarity	NPC227953
0.6766	Remote Similarity	NPC248822
0.6763	Remote Similarity	NPC135173
0.6754	Remote Similarity	NPC469505
0.6751	Remote Similarity	NPC167763
0.6751	Remote Similarity	NPC470903
0.6751	Remote Similarity	NPC470112
0.6737	Remote Similarity	NPC469479
0.6735	Remote Similarity	NPC475120
0.6734	Remote Similarity	NPC259071
0.6734	Remote Similarity	NPC77435
0.6722	Remote Similarity	NPC308571
0.6703	Remote Similarity	NPC469711
0.67	Remote Similarity	NPC474678
0.67	Remote Similarity	NPC471338
0.6684	Remote Similarity	NPC472923
0.6667	Remote Similarity	NPC475843
0.6667	Remote Similarity	NPC471337
0.665	Remote Similarity	NPC204970
0.663	Remote Similarity	NPC324081
0.6615	Remote Similarity	NPC475688
0.6599	Remote Similarity	NPC475421
0.6598	Remote Similarity	NPC477255
0.6587	Remote Similarity	NPC473450
0.6585	Remote Similarity	NPC202866
0.6576	Remote Similarity	NPC296085
0.6567	Remote Similarity	NPC8093
0.6567	Remote Similarity	NPC121571
0.6559	Remote Similarity	NPC262166
0.655	Remote Similarity	NPC477254
0.6505	Remote Similarity	NPC59827
0.6505	Remote Similarity	NPC184933
0.6502	Remote Similarity	NPC230098
0.65	Remote Similarity	NPC99723
0.6488	Remote Similarity	NPC319549
0.6486	Remote Similarity	NPC71629
0.6473	Remote Similarity	NPC33256
0.6471	Remote Similarity	NPC283207
0.6464	Remote Similarity	NPC40321
0.6456	Remote Similarity	NPC94499
0.6453	Remote Similarity	NPC4910
0.6444	Remote Similarity	NPC106606
0.6436	Remote Similarity	NPC299806
0.6422	Remote Similarity	NPC246591
0.6418	Remote Similarity	NPC474745
0.6411	Remote Similarity	NPC477527
0.6392	Remote Similarity	NPC254700
0.6387	Remote Similarity	NPC319320
0.6387	Remote Similarity	NPC287757
0.6383	Remote Similarity	NPC56685
0.6383	Remote Similarity	NPC258222
0.6378	Remote Similarity	NPC476002
0.6374	Remote Similarity	NPC128877
0.6373	Remote Similarity	NPC329731
0.6372	Remote Similarity	NPC470746
0.6372	Remote Similarity	NPC471336
0.6368	Remote Similarity	NPC474325
0.6364	Remote Similarity	NPC164608
0.635	Remote Similarity	NPC304675
0.6345	Remote Similarity	NPC100566
0.6345	Remote Similarity	NPC328494
0.6343	Remote Similarity	NPC110131
0.6341	Remote Similarity	NPC162694
0.6333	Remote Similarity	NPC293624
0.633	Remote Similarity	NPC214239
0.6324	Remote Similarity	NPC475981
0.6324	Remote Similarity	NPC474746
0.6324	Remote Similarity	NPC276120
0.6319	Remote Similarity	NPC194359
0.6319	Remote Similarity	NPC474673
0.6319	Remote Similarity	NPC28641
0.6318	Remote Similarity	NPC237044
0.6318	Remote Similarity	NPC35680
0.6311	Remote Similarity	NPC64140
0.6311	Remote Similarity	NPC174122
0.6311	Remote Similarity	NPC174629
0.6298	Remote Similarity	NPC65714
0.6296	Remote Similarity	NPC261934
0.6296	Remote Similarity	NPC202198
0.6296	Remote Similarity	NPC5194
0.6293	Remote Similarity	NPC96275
0.6281	Remote Similarity	NPC474708
0.6279	Remote Similarity	NPC195787
0.6279	Remote Similarity	NPC246140
0.6276	Remote Similarity	NPC473502
0.6276	Remote Similarity	NPC320104
0.6274	Remote Similarity	NPC123140
0.6269	Remote Similarity	NPC133817
0.6269	Remote Similarity	NPC476443
0.6268	Remote Similarity	NPC80514
0.6263	Remote Similarity	NPC47672
0.6263	Remote Similarity	NPC181653
0.6263	Remote Similarity	NPC68967
0.6263	Remote Similarity	NPC190332
0.6262	Remote Similarity	NPC234069
0.6257	Remote Similarity	NPC189908
0.6256	Remote Similarity	NPC165797
0.6256	Remote Similarity	NPC249274
0.6256	Remote Similarity	NPC4304
0.6256	Remote Similarity	NPC205167
0.625	Remote Similarity	NPC251439
0.6244	Remote Similarity	NPC234772
0.6239	Remote Similarity	NPC122886
0.6238	Remote Similarity	NPC474470
0.6238	Remote Similarity	NPC149962
0.6238	Remote Similarity	NPC308709
0.6238	Remote Similarity	NPC32064
0.6233	Remote Similarity	NPC477666
0.6232	Remote Similarity	NPC29531
0.6231	Remote Similarity	NPC266176
0.6231	Remote Similarity	NPC82533
0.6231	Remote Similarity	NPC158148
0.6231	Remote Similarity	NPC475845
0.6231	Remote Similarity	NPC290759
0.6228	Remote Similarity	NPC74216
0.6226	Remote Similarity	NPC123859
0.6222	Remote Similarity	NPC71539
0.6222	Remote Similarity	NPC250960
0.6219	Remote Similarity	NPC475976
0.6215	Remote Similarity	NPC475747
0.6215	Remote Similarity	NPC286135
0.6211	Remote Similarity	NPC226514
0.6211	Remote Similarity	NPC109968
0.6209	Remote Similarity	NPC144314
0.6209	Remote Similarity	NPC109580
0.6209	Remote Similarity	NPC471592
0.6205	Remote Similarity	NPC10653
0.6205	Remote Similarity	NPC318525
0.6205	Remote Similarity	NPC59028
0.6205	Remote Similarity	NPC475697
0.6205	Remote Similarity	NPC92191
0.6204	Remote Similarity	NPC80472
0.6203	Remote Similarity	NPC16188
0.6201	Remote Similarity	NPC195902
0.62	Remote Similarity	NPC476227
0.62	Remote Similarity	NPC26108
0.6197	Remote Similarity	NPC242728
0.6197	Remote Similarity	NPC138830
0.6195	Remote Similarity	NPC206061
0.6195	Remote Similarity	NPC138083
0.6193	Remote Similarity	NPC218614
0.6193	Remote Similarity	NPC302597
0.619	Remote Similarity	NPC471563
0.6181	Remote Similarity	NPC474324
0.6181	Remote Similarity	NPC57812
0.6181	Remote Similarity	NPC252960
0.6181	Remote Similarity	NPC298186
0.6181	Remote Similarity	NPC301189
0.618	Remote Similarity	NPC280736
0.6179	Remote Similarity	NPC50548
0.6179	Remote Similarity	NPC100863
0.6172	Remote Similarity	NPC196231
0.6171	Remote Similarity	NPC471335
0.617	Remote Similarity	NPC9373
0.6169	Remote Similarity	NPC470739
0.6169	Remote Similarity	NPC225597
0.6169	Remote Similarity	NPC477640
0.6167	Remote Similarity	NPC257390
0.6166	Remote Similarity	NPC233926
0.6166	Remote Similarity	NPC156311
0.6162	Remote Similarity	NPC186617
0.6162	Remote Similarity	NPC231198
0.6161	Remote Similarity	NPC470646
0.6157	Remote Similarity	NPC470484
0.6154	Remote Similarity	NPC474811
0.6154	Remote Similarity	NPC118099
0.6154	Remote Similarity	NPC241794
0.6154	Remote Similarity	NPC151706
0.6154	Remote Similarity	NPC474855
0.6154	Remote Similarity	NPC9687
0.6154	Remote Similarity	NPC141440
0.6154	Remote Similarity	NPC293377
0.6154	Remote Similarity	NPC79465
0.6154	Remote Similarity	NPC475598
0.6154	Remote Similarity	NPC260045
0.6154	Remote Similarity	NPC474787
0.6154	Remote Similarity	NPC90194
0.6154	Remote Similarity	NPC76785
0.6154	Remote Similarity	NPC474535
0.6154	Remote Similarity	NPC475318
0.6154	Remote Similarity	NPC273907
0.6154	Remote Similarity	NPC476102
0.6154	Remote Similarity	NPC49577
0.615	Remote Similarity	NPC135349
0.615	Remote Similarity	NPC58766
0.615	Remote Similarity	NPC79076
0.615	Remote Similarity	NPC267414

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 NPC230539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	641
0.2-0.3	1398
0.3-0.4	2687
0.4-0.5	2987
0.5-0.6	1195
0.6-0.7	50
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
0.7062	Intermediate Similarity	NPD7280	Phase 3
0.7062	Intermediate Similarity	NPD7281	Phase 3
0.6828	Remote Similarity	NPD7248	Discontinued
0.6596	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD2184	Approved
0.6595	Remote Similarity	NPD2183	Approved
0.6579	Remote Similarity	NPD5967	Approved
0.6513	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2245	Discovery
0.6488	Remote Similarity	NPD7296	Approved
0.6484	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD4010	Discontinued
0.6462	Remote Similarity	NPD4166	Phase 2
0.6436	Remote Similarity	NPD4210	Discontinued
0.6422	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6297	Approved
0.6383	Remote Similarity	NPD1670	Discontinued
0.6382	Remote Similarity	NPD5313	Approved
0.6382	Remote Similarity	NPD5312	Approved
0.6368	Remote Similarity	NPD6875	Approved
0.6368	Remote Similarity	NPD6876	Approved
0.6364	Remote Similarity	NPD3158	Phase 1
0.6364	Remote Similarity	NPD3157	Approved
0.6359	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6851	Approved
0.6355	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6853	Approved
0.6345	Remote Similarity	NPD5137	Approved
0.6337	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7131	Phase 3
0.6296	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD1298	Discontinued
0.6278	Remote Similarity	NPD2238	Phase 2
0.6269	Remote Similarity	NPD5773	Approved
0.6269	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5772	Approved
0.625	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7110	Phase 1
0.6238	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD4236	Phase 3
0.6183	Remote Similarity	NPD4237	Approved
0.6181	Remote Similarity	NPD6687	Approved
0.6181	Remote Similarity	NPD6688	Approved
0.6176	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6666	Approved
0.617	Remote Similarity	NPD6667	Approved
0.615	Remote Similarity	NPD7810	Phase 3
0.615	Remote Similarity	NPD5754	Discontinued
0.615	Remote Similarity	NPD7811	Phase 3
0.6138	Remote Similarity	NPD5297	Approved
0.6133	Remote Similarity	NPD5745	Approved
0.6126	Remote Similarity	NPD3641	Approved
0.6126	Remote Similarity	NPD3639	Approved
0.6126	Remote Similarity	NPD3640	Phase 3
0.6111	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD2667	Approved
0.6092	Remote Similarity	NPD2668	Approved
0.6089	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD7177	Discontinued
0.6087	Remote Similarity	NPD743	Approved
0.608	Remote Similarity	NPD2233	Approved
0.608	Remote Similarity	NPD7485	Phase 3
0.608	Remote Similarity	NPD7484	Phase 3
0.608	Remote Similarity	NPD2232	Approved
0.608	Remote Similarity	NPD2230	Approved
0.6075	Remote Similarity	NPD8095	Phase 1
0.6068	Remote Similarity	NPD3337	Discontinued
0.6067	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD824	Approved
0.6061	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6315	Phase 2
0.6059	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7432	Phase 2
0.6032	Remote Similarity	NPD2219	Phase 1
0.6029	Remote Similarity	NPD4157	Discontinued
0.6022	Remote Similarity	NPD5746	Approved
0.6021	Remote Similarity	NPD7020	Approved
0.6021	Remote Similarity	NPD7019	Approved
0.6011	Remote Similarity	NPD2654	Approved
0.6009	Remote Similarity	NPD4040	Phase 1
0.6	Remote Similarity	NPD6385	Approved
0.6	Remote Similarity	NPD6386	Approved
0.599	Remote Similarity	NPD2968	Approved
0.599	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.599	Remote Similarity	NPD2971	Approved
0.599	Remote Similarity	NPD7613	Discontinued
0.599	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD2974	Approved
0.5981	Remote Similarity	NPD2973	Approved
0.5981	Remote Similarity	NPD2975	Approved
0.5981	Remote Similarity	NPD5564	Approved
0.598	Remote Similarity	NPD6042	Phase 2
0.598	Remote Similarity	NPD42	Phase 2
0.5972	Remote Similarity	NPD2490	Approved
0.5972	Remote Similarity	NPD4580	Approved
0.5972	Remote Similarity	NPD6505	Approved
0.5972	Remote Similarity	NPD6504	Approved
0.5972	Remote Similarity	NPD2488	Approved
0.597	Remote Similarity	NPD7315	Approved
0.597	Remote Similarity	NPD3051	Approved
0.5969	Remote Similarity	NPD4227	Discontinued
0.5969	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6618	Phase 2
0.5956	Remote Similarity	NPD7086	Phase 2
0.5955	Remote Similarity	NPD1421	Approved
0.5955	Remote Similarity	NPD1420	Approved
0.5951	Remote Similarity	NPD5484	Approved
0.5951	Remote Similarity	NPD5485	Approved
0.5947	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD3692	Discontinued
0.5946	Remote Similarity	NPD8172	Phase 2
0.5946	Remote Similarity	NPD8173	Phase 2
0.5946	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD7905	Discontinued
0.5941	Remote Similarity	NPD2969	Approved
0.5941	Remote Similarity	NPD2970	Approved
0.5939	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD3146	Approved
0.5934	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD6620	Discovery
0.592	Remote Similarity	NPD2516	Approved
0.592	Remote Similarity	NPD6107	Approved
0.5918	Remote Similarity	NPD4772	Phase 2
0.5918	Remote Similarity	NPD4773	Phase 2
0.5918	Remote Similarity	NPD4424	Discontinued
0.5917	Remote Similarity	NPD6863	Phase 2
0.5916	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD2560	Approved
0.5909	Remote Similarity	NPD8161	Suspended
0.5909	Remote Similarity	NPD2563	Approved
0.5899	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7827	Phase 1
0.5891	Remote Similarity	NPD6071	Discontinued
0.5891	Remote Similarity	NPD2517	Approved
0.5891	Remote Similarity	NPD7608	Discontinued
0.5889	Remote Similarity	NPD1318	Phase 2
0.5888	Remote Similarity	NPD7669	Phase 3
0.5888	Remote Similarity	NPD6844	Discontinued
0.588	Remote Similarity	NPD4420	Approved
0.5874	Remote Similarity	NPD5557	Phase 1
0.5874	Remote Similarity	NPD4956	Approved
0.5872	Remote Similarity	NPD2494	Approved
0.5872	Remote Similarity	NPD2493	Approved
0.5871	Remote Similarity	NPD2904	Discontinued
0.587	Remote Similarity	NPD6997	Phase 2
0.5864	Remote Similarity	NPD4583	Approved
0.5864	Remote Similarity	NPD5241	Discontinued
0.5864	Remote Similarity	NPD4582	Approved
0.586	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.586	Remote Similarity	NPD5582	Discontinued
0.586	Remote Similarity	NPD5725	Approved
0.586	Remote Similarity	NPD4361	Phase 2
0.5855	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD6032	Approved
0.585	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD9718	Approved
0.5846	Remote Similarity	NPD3686	Approved
0.5846	Remote Similarity	NPD3687	Approved
0.5845	Remote Similarity	NPD5006	Approved
0.5845	Remote Similarity	NPD5005	Approved
0.5845	Remote Similarity	NPD3057	Approved
0.5842	Remote Similarity	NPD3060	Approved
0.5838	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2489	Approved
0.5833	Remote Similarity	NPD7124	Phase 2
0.5833	Remote Similarity	NPD6894	Phase 1
0.5833	Remote Similarity	NPD4481	Phase 3
0.5833	Remote Similarity	NPD27	Approved
0.5829	Remote Similarity	NPD6896	Approved
0.5829	Remote Similarity	NPD4434	Approved
0.5829	Remote Similarity	NPD6895	Approved
0.5825	Remote Similarity	NPD6390	Discontinued
0.5824	Remote Similarity	NPD4177	Approved
0.5824	Remote Similarity	NPD4175	Approved
0.5818	Remote Similarity	NPD4004	Approved
0.5818	Remote Similarity	NPD4002	Approved
0.5817	Remote Similarity	NPD5039	Approved
0.5817	Remote Similarity	NPD7038	Approved
0.5817	Remote Similarity	NPD7039	Approved
0.5816	Remote Similarity	NPD2651	Approved
0.5816	Remote Similarity	NPD2649	Approved
0.5815	Remote Similarity	NPD5718	Phase 2
0.5808	Remote Similarity	NPD5355	Approved
0.5808	Remote Similarity	NPD5356	Approved
0.5805	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7291	Discontinued
0.5802	Remote Similarity	NPD4435	Approved
0.5801	Remote Similarity	NPD4098	Discontinued
0.5799	Remote Similarity	NPD3450	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