NPASS Compound

Structure

NPC64066 OpenBabel07101718292D 22 24 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 -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 -0.5878 -0.8090 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 -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 0.0000 -0.0000 0.0000 N 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 -0.8968 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 22 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 5 18 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 12 1 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 1 0 0 0 13 19 1 0 0 0 0 13 20 1 1 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 14 21 2 0 0 0 0 15 4 1 6 0 0 0 15 18 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	431.97
Volume:	318.712
LogP:	2.209
LogD:	1.678
LogS:	-3.295
# Rotatable Bonds:	2
TPSA:	61.8
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	4.546
Fsp3:	0.533
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:	-4.915
MDCK Permeability:	1.9346865883562714e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.298
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.643

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.544
Plasma Protein Binding (PPB):	89.11149597167969%
Volume Distribution (VD):	2.377
Pgp-substrate:	17.270410537719727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.16
CYP1A2-substrate:	0.775
CYP2C19-inhibitor:	0.104
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.566
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.629
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	2.409
Half-life (T1/2):	0.353

ADMET: Toxicity

hERG Blockers:	0.156
Human Hepatotoxicity (H-HT):	0.294
Drug-inuced Liver Injury (DILI):	0.134
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.613
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.339
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.249

Download Data

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

Natural Product: NPC64066

Natural Product ID:	NPC64066
*Common Name:**	Amathaspiramide C
IUPAC Name:	(5S,8R,9R)-9-(2,4-dibromo-5-methoxyphenyl)-8-hydroxy-7-methyl-1,7-diazaspiro[4.4]nonan-6-one
Synonyms:	Amathaspiramide C
Standard InCHIKey:	ZNKJMNWJZBGNNZ-GUTXKFCHSA-N
Standard InCHI:	InChI=1S/C15H18Br2N2O3/c1-19-13(20)12(15(14(19)21)4-3-5-18-15)8-6-11(22-2)10(17)7-9(8)16/h6-7,12-13,18,20H,3-5H2,1-2H3/t12-,13+,15-/m0/s1
SMILES:	COc1cc(c(cc1Br)Br)[C@H]1[C@@H](O)N(C(=O)[C@@]21CCCN2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523642
PubChem CID:	10694112
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[551853]

☑ 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 NPC64066 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	283
0.1-0.2	1532
0.2-0.3	8942
0.3-0.4	9709
0.4-0.5	18316
0.5-0.6	3623
0.6-0.7	280
0.7-0.8	7
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9649	High Similarity	NPC80337
0.9538	High Similarity	NPC230539
0.8994	High Similarity	NPC102245
0.7471	Intermediate Similarity	NPC235633
0.7225	Intermediate Similarity	NPC470248
0.7176	Intermediate Similarity	NPC135173
0.7143	Intermediate Similarity	NPC470250
0.7126	Intermediate Similarity	NPC470249
0.7119	Intermediate Similarity	NPC308571
0.7088	Intermediate Similarity	NPC469711
0.702	Intermediate Similarity	NPC147847
0.697	Remote Similarity	NPC174607
0.6965	Remote Similarity	NPC227953
0.6919	Remote Similarity	NPC259071
0.6919	Remote Similarity	NPC77435
0.6881	Remote Similarity	NPC471338
0.6881	Remote Similarity	NPC474678
0.6866	Remote Similarity	NPC248822
0.6847	Remote Similarity	NPC475843
0.6845	Remote Similarity	NPC471337
0.6788	Remote Similarity	NPC477255
0.6765	Remote Similarity	NPC202866
0.6763	Remote Similarity	NPC473450
0.676	Remote Similarity	NPC128877
0.675	Remote Similarity	NPC8093
0.675	Remote Similarity	NPC121571
0.674	Remote Similarity	NPC470247
0.6734	Remote Similarity	NPC477254
0.6722	Remote Similarity	NPC470709
0.665	Remote Similarity	NPC283207
0.6617	Remote Similarity	NPC102760
0.6617	Remote Similarity	NPC299806
0.6611	Remote Similarity	NPC474673
0.6601	Remote Similarity	NPC246591
0.6559	Remote Similarity	NPC324081
0.6553	Remote Similarity	NPC473941
0.6542	Remote Similarity	NPC470746
0.6542	Remote Similarity	NPC471336
0.6522	Remote Similarity	NPC79076
0.6517	Remote Similarity	NPC470903
0.6517	Remote Similarity	NPC167763
0.6517	Remote Similarity	NPC470112
0.6513	Remote Similarity	NPC469505
0.65	Remote Similarity	NPC475120
0.6497	Remote Similarity	NPC474087
0.6495	Remote Similarity	NPC469479
0.6471	Remote Similarity	NPC96275
0.6455	Remote Similarity	NPC47672
0.6445	Remote Similarity	NPC123140
0.6443	Remote Similarity	NPC472923
0.6442	Remote Similarity	NPC80514
0.644	Remote Similarity	NPC233926
0.6425	Remote Similarity	NPC204970
0.6417	Remote Similarity	NPC296085
0.6393	Remote Similarity	NPC40321
0.6382	Remote Similarity	NPC475688
0.6368	Remote Similarity	NPC475421
0.6355	Remote Similarity	NPC99723
0.6354	Remote Similarity	NPC156311
0.6351	Remote Similarity	NPC100863
0.6335	Remote Similarity	NPC471335
0.633	Remote Similarity	NPC71629
0.6321	Remote Similarity	NPC287757
0.6321	Remote Similarity	NPC319320
0.6319	Remote Similarity	NPC470471
0.6316	Remote Similarity	NPC56685
0.6316	Remote Similarity	NPC262166
0.6296	Remote Similarity	NPC246140
0.6296	Remote Similarity	NPC195787
0.6289	Remote Similarity	NPC160931
0.6289	Remote Similarity	NPC37205
0.6286	Remote Similarity	NPC59827
0.6286	Remote Similarity	NPC184933
0.6281	Remote Similarity	NPC328494
0.628	Remote Similarity	NPC230098
0.6271	Remote Similarity	NPC110131
0.6268	Remote Similarity	NPC319549
0.6263	Remote Similarity	NPC76412
0.6256	Remote Similarity	NPC33256
0.6256	Remote Similarity	NPC122886
0.625	Remote Similarity	NPC470470
0.6239	Remote Similarity	NPC471339
0.6238	Remote Similarity	NPC94499
0.6237	Remote Similarity	NPC204546
0.6232	Remote Similarity	NPC4910
0.6215	Remote Similarity	NPC272463
0.6214	Remote Similarity	NPC473007
0.6209	Remote Similarity	NPC243626
0.6197	Remote Similarity	NPC477527
0.6196	Remote Similarity	NPC106606
0.6195	Remote Similarity	NPC474745
0.6193	Remote Similarity	NPC478075
0.6182	Remote Similarity	NPC197125
0.6178	Remote Similarity	NPC214239
0.6175	Remote Similarity	NPC87714
0.617	Remote Similarity	NPC78530
0.6162	Remote Similarity	NPC194359
0.6162	Remote Similarity	NPC254700
0.6162	Remote Similarity	NPC28641
0.6161	Remote Similarity	NPC314083
0.6158	Remote Similarity	NPC143450
0.6154	Remote Similarity	NPC329731
0.615	Remote Similarity	NPC476002
0.6146	Remote Similarity	NPC226514
0.6146	Remote Similarity	NPC474325
0.6146	Remote Similarity	NPC258222
0.614	Remote Similarity	NPC477551
0.614	Remote Similarity	NPC242728
0.6139	Remote Similarity	NPC164608
0.6136	Remote Similarity	NPC477160
0.6135	Remote Similarity	NPC138083
0.6133	Remote Similarity	NPC195902
0.6131	Remote Similarity	NPC320104
0.6127	Remote Similarity	NPC304675
0.6124	Remote Similarity	NPC162694
0.6122	Remote Similarity	NPC476443
0.6122	Remote Similarity	NPC133817
0.6121	Remote Similarity	NPC477552
0.6121	Remote Similarity	NPC477550
0.6119	Remote Similarity	NPC100566
0.6114	Remote Similarity	NPC68967
0.6111	Remote Similarity	NPC280736
0.6111	Remote Similarity	NPC249274
0.6106	Remote Similarity	NPC475981
0.6106	Remote Similarity	NPC474746
0.6106	Remote Similarity	NPC276120
0.6106	Remote Similarity	NPC219397
0.6105	Remote Similarity	NPC189908
0.6098	Remote Similarity	NPC237044
0.6098	Remote Similarity	NPC35680
0.6096	Remote Similarity	NPC251439
0.6095	Remote Similarity	NPC473008
0.6095	Remote Similarity	NPC174629
0.6091	Remote Similarity	NPC241794
0.6085	Remote Similarity	NPC65714
0.6085	Remote Similarity	NPC470472
0.6082	Remote Similarity	NPC244509
0.6082	Remote Similarity	NPC476268
0.607	Remote Similarity	NPC46009
0.607	Remote Similarity	NPC475123
0.607	Remote Similarity	NPC475204
0.6068	Remote Similarity	NPC197335
0.6065	Remote Similarity	NPC138830
0.6062	Remote Similarity	NPC261934
0.6062	Remote Similarity	NPC5194
0.6062	Remote Similarity	NPC202198
0.6062	Remote Similarity	NPC470082
0.6059	Remote Similarity	NPC474708
0.6058	Remote Similarity	NPC129885
0.6054	Remote Similarity	NPC109580
0.6053	Remote Similarity	NPC125852
0.605	Remote Similarity	NPC328649
0.605	Remote Similarity	NPC473502
0.6047	Remote Similarity	NPC293624
0.6044	Remote Similarity	NPC234772
0.604	Remote Similarity	NPC191557
0.604	Remote Similarity	NPC190332
0.604	Remote Similarity	NPC181653
0.604	Remote Similarity	NPC89831
0.6039	Remote Similarity	NPC314659
0.6032	Remote Similarity	NPC125861
0.603	Remote Similarity	NPC205167
0.603	Remote Similarity	NPC63931
0.603	Remote Similarity	NPC165797
0.603	Remote Similarity	NPC4304
0.603	Remote Similarity	NPC135006
0.6028	Remote Similarity	NPC308709
0.6028	Remote Similarity	NPC149962
0.6027	Remote Similarity	NPC477666
0.6026	Remote Similarity	NPC250960
0.6026	Remote Similarity	NPC71539
0.6022	Remote Similarity	NPC242159
0.6022	Remote Similarity	NPC313694
0.6021	Remote Similarity	NPC9373
0.602	Remote Similarity	NPC129486
0.602	Remote Similarity	NPC280022
0.6019	Remote Similarity	NPC474470
0.6019	Remote Similarity	NPC64140
0.6019	Remote Similarity	NPC29531
0.6019	Remote Similarity	NPC474059
0.6019	Remote Similarity	NPC123859
0.6019	Remote Similarity	NPC32064
0.6019	Remote Similarity	NPC174122
0.6011	Remote Similarity	NPC70485
0.6011	Remote Similarity	NPC116562
0.601	Remote Similarity	NPC475845
0.601	Remote Similarity	NPC290759
0.601	Remote Similarity	NPC158148
0.601	Remote Similarity	NPC90245
0.601	Remote Similarity	NPC82533
0.601	Remote Similarity	NPC266176
0.6009	Remote Similarity	NPC470485
0.6009	Remote Similarity	NPC318525
0.6009	Remote Similarity	NPC1464
0.6009	Remote Similarity	NPC10653
0.6009	Remote Similarity	NPC286135
0.6	Remote Similarity	NPC144314
0.6	Remote Similarity	NPC79465
0.6	Remote Similarity	NPC80472
0.6	Remote Similarity	NPC118099

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 NPC64066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	619
0.2-0.3	1390
0.3-0.4	2605
0.4-0.5	3108
0.5-0.6	1201
0.6-0.7	49
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
0.6818	Remote Similarity	NPD7281	Phase 3
0.6818	Remote Similarity	NPD7280	Phase 3
0.68	Remote Similarity	NPD2245	Discovery
0.6667	Remote Similarity	NPD7248	Discontinued
0.6649	Remote Similarity	NPD4166	Phase 2
0.6633	Remote Similarity	NPD1298	Discontinued
0.6583	Remote Similarity	NPD6297	Approved
0.6559	Remote Similarity	NPD3157	Approved
0.6559	Remote Similarity	NPD3158	Phase 1
0.6535	Remote Similarity	NPD6851	Approved
0.6535	Remote Similarity	NPD6853	Approved
0.6531	Remote Similarity	NPD5137	Approved
0.6526	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD2183	Approved
0.6436	Remote Similarity	NPD2184	Approved
0.634	Remote Similarity	NPD5967	Approved
0.6324	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD7296	Approved
0.6268	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7485	Phase 3
0.6263	Remote Similarity	NPD7484	Phase 3
0.6244	Remote Similarity	NPD6315	Phase 2
0.6231	Remote Similarity	NPD4010	Discontinued
0.623	Remote Similarity	NPD1670	Discontinued
0.6202	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4210	Discontinued
0.6158	Remote Similarity	NPD5313	Approved
0.6158	Remote Similarity	NPD6042	Phase 2
0.6158	Remote Similarity	NPD5312	Approved
0.6158	Remote Similarity	NPD42	Phase 2
0.6154	Remote Similarity	NPD4227	Discontinued
0.6146	Remote Similarity	NPD7131	Phase 3
0.6143	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD6618	Phase 2
0.6134	Remote Similarity	NPD6875	Approved
0.6134	Remote Similarity	NPD6876	Approved
0.6133	Remote Similarity	NPD9718	Approved
0.612	Remote Similarity	NPD2238	Phase 2
0.6117	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD6620	Discovery
0.6101	Remote Similarity	NPD4040	Phase 1
0.6089	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD2651	Approved
0.6082	Remote Similarity	NPD2649	Approved
0.6062	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7669	Phase 3
0.6054	Remote Similarity	NPD5725	Approved
0.6054	Remote Similarity	NPD7827	Phase 1
0.6051	Remote Similarity	NPD1009	Approved
0.6048	Remote Similarity	NPD4157	Discontinued
0.6042	Remote Similarity	NPD7019	Approved
0.6042	Remote Similarity	NPD7020	Approved
0.6041	Remote Similarity	NPD5773	Approved
0.6041	Remote Similarity	NPD5772	Approved
0.6039	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD3060	Approved
0.6031	Remote Similarity	NPD3686	Approved
0.6031	Remote Similarity	NPD3687	Approved
0.6028	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD4177	Approved
0.6022	Remote Similarity	NPD743	Approved
0.6022	Remote Similarity	NPD4175	Approved
0.6021	Remote Similarity	NPD6666	Approved
0.6021	Remote Similarity	NPD6667	Approved
0.602	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7110	Phase 1
0.602	Remote Similarity	NPD6107	Approved
0.601	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD6863	Phase 2
0.6	Remote Similarity	NPD824	Approved
0.6	Remote Similarity	NPD5754	Discontinued
0.599	Remote Similarity	NPD5356	Approved
0.599	Remote Similarity	NPD7039	Approved
0.599	Remote Similarity	NPD7038	Approved
0.599	Remote Similarity	NPD5355	Approved
0.5989	Remote Similarity	NPD600	Approved
0.5989	Remote Similarity	NPD596	Approved
0.5989	Remote Similarity	NPD4676	Approved
0.598	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD3639	Approved
0.5979	Remote Similarity	NPD3641	Approved
0.5979	Remote Similarity	NPD3640	Phase 3
0.5978	Remote Similarity	NPD3163	Approved
0.5978	Remote Similarity	NPD3162	Approved
0.597	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.597	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD2677	Approved
0.5968	Remote Similarity	NPD6073	Approved
0.5967	Remote Similarity	NPD859	Approved
0.5967	Remote Similarity	NPD858	Approved
0.5962	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD6688	Approved
0.5961	Remote Similarity	NPD6687	Approved
0.596	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.596	Remote Similarity	NPD2978	Approved
0.596	Remote Similarity	NPD2977	Approved
0.5959	Remote Similarity	NPD1424	Approved
0.5959	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD2240	Approved
0.5957	Remote Similarity	NPD2239	Approved
0.5951	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.595	Remote Similarity	NPD1309	Phase 2
0.595	Remote Similarity	NPD1307	Phase 2
0.5947	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD4237	Approved
0.5947	Remote Similarity	NPD4236	Phase 3
0.5945	Remote Similarity	NPD7811	Phase 3
0.5945	Remote Similarity	NPD7810	Phase 3
0.5944	Remote Similarity	NPD196	Phase 1
0.5938	Remote Similarity	NPD2120	Phase 2
0.5934	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.5933	Remote Similarity	NPD3337	Discontinued
0.5932	Remote Similarity	NPD2668	Approved
0.5932	Remote Similarity	NPD2667	Approved
0.5928	Remote Similarity	NPD7613	Discontinued
0.5922	Remote Similarity	NPD2233	Approved
0.5922	Remote Similarity	NPD3072	Approved
0.5922	Remote Similarity	NPD2230	Approved
0.5922	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD2232	Approved
0.5922	Remote Similarity	NPD3073	Approved
0.5922	Remote Similarity	NPD3071	Approved
0.5915	Remote Similarity	NPD7668	Phase 2
0.5913	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD5297	Approved
0.5902	Remote Similarity	NPD5263	Approved
0.5892	Remote Similarity	NPD554	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD5745	Approved
0.5891	Remote Similarity	NPD1411	Approved
0.589	Remote Similarity	NPD6238	Discontinued
0.5889	Remote Similarity	NPD1421	Approved
0.5889	Remote Similarity	NPD1420	Approved
0.5885	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3054	Approved
0.5882	Remote Similarity	NPD3052	Approved
0.5879	Remote Similarity	NPD602	Approved
0.5879	Remote Similarity	NPD599	Approved
0.5879	Remote Similarity	NPD558	Phase 2
0.5876	Remote Similarity	NPD2874	Phase 2
0.5874	Remote Similarity	NPD7177	Discontinued
0.5872	Remote Similarity	NPD8095	Phase 1
0.587	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.5866	Remote Similarity	NPD4761	Approved
0.5866	Remote Similarity	NPD4762	Approved
0.5864	Remote Similarity	NPD4162	Approved
0.5864	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD593	Approved
0.5862	Remote Similarity	NPD595	Approved
0.5859	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD2971	Approved
0.5857	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD2968	Approved
0.5857	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD3122	Phase 3
0.5855	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7432	Phase 2
0.585	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD8303	Discontinued
0.5841	Remote Similarity	NPD2488	Approved
0.5841	Remote Similarity	NPD2490	Approved
0.5838	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD1330	Phase 2
0.5838	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3051	Approved
0.5833	Remote Similarity	NPD2235	Phase 2
0.5833	Remote Similarity	NPD2231	Phase 2
0.5833	Remote Similarity	NPD7608	Discontinued
0.5833	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD1318	Phase 2
0.5819	Remote Similarity	NPD316	Approved
0.5817	Remote Similarity	NPD5557	Phase 1
0.5806	Remote Similarity	NPD1130	Approved
0.5806	Remote Similarity	NPD1136	Approved
0.5806	Remote Similarity	NPD839	Approved
0.5806	Remote Similarity	NPD1132	Approved
0.5806	Remote Similarity	NPD840	Approved
0.5806	Remote Similarity	NPD7086	Phase 2
0.5805	Remote Similarity	NPD2970	Approved
0.5805	Remote Similarity	NPD2969	Approved
0.5803	Remote Similarity	NPD2219	Phase 1
0.5803	Remote Similarity	NPD3692	Discontinued
0.5803	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.5799	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD2653	Approved
0.5797	Remote Similarity	NPD2163	Approved
0.5795	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD8031	Discontinued
0.5792	Remote Similarity	NPD7905	Discontinued
0.5789	Remote Similarity	NPD3156	Discontinued
0.5785	Remote Similarity	NPD7174	Clinical (unspecified phase)

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