NPASS Compound

Structure

NPC473252 OpenBabel07101718322D 25 27 0 0 1 0 0 0 0 0999 V2000 6.3916 -0.1293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9975 0.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6485 0.5398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6974 0.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3102 2.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9543 0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3127 2.6976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8701 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8751 1.7984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4326 1.0405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0032 0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4351 0.9698 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9975 0.0707 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5574 -0.7579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -1.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 18 1 0 0 0 0 3 4 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 1 1 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 6 0 0 0 15 22 1 1 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 1 0 0 0 18 25 1 0 0 0 0 19 15 1 1 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	351.2
Volume:	358.549
LogP:	3.107
LogD:	3.001
LogS:	-3.643
# Rotatable Bonds:	7
TPSA:	95.86
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.366
Synthetic Accessibility Score:	4.778
Fsp3:	0.789
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.647
MDCK Permeability:	3.168839612044394e-05
Pgp-inhibitor:	0.076
Pgp-substrate:	0.16
Human Intestinal Absorption (HIA):	0.589
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.703
Plasma Protein Binding (PPB):	87.90557098388672%
Volume Distribution (VD):	0.789
Pgp-substrate:	13.93126392364502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.834
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.146
CYP2C9-substrate:	0.17
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.704
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	10.819
Half-life (T1/2):	0.346

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.235
Maximum Recommended Daily Dose:	0.287
Skin Sensitization:	0.281
Carcinogencity:	0.891
Eye Corrosion:	0.005
Eye Irritation:	0.02
Respiratory Toxicity:	0.414

Download Data

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

Natural Product: NPC473252

Natural Product ID:	NPC473252
*Common Name:**	Cinnabaramide B
IUPAC Name:	(1S,2R,5R)-5-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-2-(1-hydroxyhexyl)-1-methyl-7-oxa-4-azabicyclo[3.2.0]heptane-3,6-dione
Synonyms:
Standard InCHIKey:	YZIAPUWXZJLPJK-MOEJHERCSA-N
Standard InCHI:	InChI=1S/C19H29NO5/c1-3-4-6-11-13(21)14-16(23)20-19(17(24)25-18(14,19)2)15(22)12-9-7-5-8-10-12/h7,9,12-15,21-22H,3-6,8,10-11H2,1-2H3,(H,20,23)/t12-,13?,14+,15+,18+,19+/m1/s1
SMILES:	CCCCCC(C1C(=O)NC2(C1(OC2=O)C)C(C3CCCC=C3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387140
PubChem CID:	16109811
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

*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
NPO32890	terrestrial streptomycete	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17249727]

☑ 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
Others	1

Activity Type	# Activity
Others	1
PROTEIN COMPLEX	19

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24354	PROTEIN COMPLEX	20S proteasome	Homo sapiens	IC50	=	245.0	nM	PMID[512248]
NPT35	Others	n.a.		Stability	=	50.0	%	PMID[512248]

☑ 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 NPC473252 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	98
0.1-0.2	592
0.2-0.3	4755
0.3-0.4	20464
0.4-0.5	11431
0.5-0.6	5154
0.6-0.7	186
0.7-0.8	6
0.8-0.85	5
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC14537
0.9485	High Similarity	NPC473224
0.9381	High Similarity	NPC234542
0.9175	High Similarity	NPC123141
0.9135	High Similarity	NPC12270
0.8378	Intermediate Similarity	NPC201968
0.8198	Intermediate Similarity	NPC50694
0.7596	Intermediate Similarity	NPC226513
0.7281	Intermediate Similarity	NPC474725
0.7257	Intermediate Similarity	NPC475800
0.7193	Intermediate Similarity	NPC70235
0.717	Intermediate Similarity	NPC314500
0.7019	Intermediate Similarity	NPC475753
0.7018	Intermediate Similarity	NPC472615
0.6991	Remote Similarity	NPC215988
0.6981	Remote Similarity	NPC256902
0.6981	Remote Similarity	NPC118193
0.693	Remote Similarity	NPC472616
0.687	Remote Similarity	NPC271269
0.6838	Remote Similarity	NPC473578
0.6796	Remote Similarity	NPC474312
0.6796	Remote Similarity	NPC47135
0.6792	Remote Similarity	NPC86005
0.6783	Remote Similarity	NPC74035
0.6757	Remote Similarity	NPC180722
0.6757	Remote Similarity	NPC195645
0.6757	Remote Similarity	NPC165332
0.6752	Remote Similarity	NPC307903
0.6752	Remote Similarity	NPC140251
0.6752	Remote Similarity	NPC475150
0.6724	Remote Similarity	NPC154601
0.6696	Remote Similarity	NPC474563
0.6696	Remote Similarity	NPC475438
0.6695	Remote Similarity	NPC133729
0.6694	Remote Similarity	NPC471645
0.6667	Remote Similarity	NPC251330
0.6667	Remote Similarity	NPC469865
0.6667	Remote Similarity	NPC39290
0.6667	Remote Similarity	NPC159369
0.6667	Remote Similarity	NPC97577
0.6641	Remote Similarity	NPC204556
0.6636	Remote Similarity	NPC477959
0.6585	Remote Similarity	NPC147707
0.6581	Remote Similarity	NPC475918
0.6577	Remote Similarity	NPC5418
0.6545	Remote Similarity	NPC36491
0.6542	Remote Similarity	NPC258824
0.6532	Remote Similarity	NPC471121
0.6532	Remote Similarity	NPC9714
0.6532	Remote Similarity	NPC471118
0.6529	Remote Similarity	NPC1111
0.6529	Remote Similarity	NPC261750
0.6508	Remote Similarity	NPC23963
0.65	Remote Similarity	NPC122926
0.65	Remote Similarity	NPC113012
0.65	Remote Similarity	NPC127578
0.65	Remote Similarity	NPC46764
0.65	Remote Similarity	NPC476290
0.648	Remote Similarity	NPC323532
0.6462	Remote Similarity	NPC477793
0.6462	Remote Similarity	NPC329919
0.6455	Remote Similarity	NPC313670
0.6452	Remote Similarity	NPC471120
0.6452	Remote Similarity	NPC471117
0.6442	Remote Similarity	NPC103634
0.6417	Remote Similarity	NPC329305
0.6417	Remote Similarity	NPC474891
0.6408	Remote Similarity	NPC11796
0.6408	Remote Similarity	NPC218817
0.6404	Remote Similarity	NPC4834
0.6404	Remote Similarity	NPC167380
0.6393	Remote Similarity	NPC476269
0.6393	Remote Similarity	NPC60432
0.6379	Remote Similarity	NPC474873
0.6379	Remote Similarity	NPC316250
0.6378	Remote Similarity	NPC469515
0.6373	Remote Similarity	NPC469514
0.6372	Remote Similarity	NPC54905
0.6372	Remote Similarity	NPC314009
0.6371	Remote Similarity	NPC30196
0.6357	Remote Similarity	NPC469494
0.6355	Remote Similarity	NPC295799
0.6328	Remote Similarity	NPC80150
0.6328	Remote Similarity	NPC273185
0.6325	Remote Similarity	NPC469598
0.6325	Remote Similarity	NPC474747
0.6321	Remote Similarity	NPC474252
0.632	Remote Similarity	NPC6531
0.632	Remote Similarity	NPC316325
0.632	Remote Similarity	NPC476190
0.6316	Remote Similarity	NPC469528
0.6316	Remote Similarity	NPC473859
0.6316	Remote Similarity	NPC475503
0.6316	Remote Similarity	NPC469369
0.6316	Remote Similarity	NPC121857
0.6311	Remote Similarity	NPC120776
0.6311	Remote Similarity	NPC240170
0.6311	Remote Similarity	NPC281296
0.6311	Remote Similarity	NPC29501
0.6306	Remote Similarity	NPC473448
0.6303	Remote Similarity	NPC101106
0.6303	Remote Similarity	NPC135216
0.6296	Remote Similarity	NPC475206
0.6283	Remote Similarity	NPC473314
0.6276	Remote Similarity	NPC315809
0.6276	Remote Similarity	NPC314050
0.6273	Remote Similarity	NPC193386
0.6273	Remote Similarity	NPC202672
0.6271	Remote Similarity	NPC475945
0.6271	Remote Similarity	NPC475871
0.6271	Remote Similarity	NPC4620
0.627	Remote Similarity	NPC106791
0.627	Remote Similarity	NPC201889
0.6269	Remote Similarity	NPC314361
0.6263	Remote Similarity	NPC199557
0.6262	Remote Similarity	NPC69469
0.6261	Remote Similarity	NPC40812
0.626	Remote Similarity	NPC273215
0.626	Remote Similarity	NPC279383
0.626	Remote Similarity	NPC268327
0.626	Remote Similarity	NPC7797
0.626	Remote Similarity	NPC295444
0.626	Remote Similarity	NPC66108
0.625	Remote Similarity	NPC127526
0.625	Remote Similarity	NPC300312
0.625	Remote Similarity	NPC121200
0.625	Remote Similarity	NPC184463
0.625	Remote Similarity	NPC319473
0.625	Remote Similarity	NPC472430
0.625	Remote Similarity	NPC261607
0.625	Remote Similarity	NPC111114
0.6239	Remote Similarity	NPC477994
0.6239	Remote Similarity	NPC474742
0.6239	Remote Similarity	NPC477993
0.6239	Remote Similarity	NPC472753
0.6239	Remote Similarity	NPC116575
0.6238	Remote Similarity	NPC167145
0.6238	Remote Similarity	NPC326024
0.6231	Remote Similarity	NPC314512
0.6231	Remote Similarity	NPC313342
0.6231	Remote Similarity	NPC314451
0.6231	Remote Similarity	NPC313333
0.6228	Remote Similarity	NPC475659
0.6226	Remote Similarity	NPC191711
0.6222	Remote Similarity	NPC76999
0.6218	Remote Similarity	NPC119329
0.6218	Remote Similarity	NPC220964
0.6218	Remote Similarity	NPC475676
0.6216	Remote Similarity	NPC295312
0.6216	Remote Similarity	NPC117405
0.6216	Remote Similarity	NPC52198
0.6212	Remote Similarity	NPC476957
0.621	Remote Similarity	NPC106479
0.6207	Remote Similarity	NPC187761
0.6207	Remote Similarity	NPC261377
0.6207	Remote Similarity	NPC83895
0.6207	Remote Similarity	NPC477854
0.6207	Remote Similarity	NPC308567
0.6207	Remote Similarity	NPC255592
0.6204	Remote Similarity	NPC474776
0.6198	Remote Similarity	NPC287572
0.6198	Remote Similarity	NPC471636
0.6195	Remote Similarity	NPC476049
0.6195	Remote Similarity	NPC212486
0.6195	Remote Similarity	NPC475912
0.6194	Remote Similarity	NPC139585
0.619	Remote Similarity	NPC188010
0.619	Remote Similarity	NPC113363
0.6186	Remote Similarity	NPC128501
0.6186	Remote Similarity	NPC472754
0.6186	Remote Similarity	NPC477198
0.6186	Remote Similarity	NPC72401
0.6186	Remote Similarity	NPC325339
0.6182	Remote Similarity	NPC472614
0.6182	Remote Similarity	NPC179659
0.6179	Remote Similarity	NPC475608
0.6179	Remote Similarity	NPC21713
0.6176	Remote Similarity	NPC75318
0.6176	Remote Similarity	NPC330016
0.6174	Remote Similarity	NPC477853
0.6172	Remote Similarity	NPC310467
0.6168	Remote Similarity	NPC7414
0.6165	Remote Similarity	NPC164476
0.6165	Remote Similarity	NPC471471
0.6161	Remote Similarity	NPC478003
0.6161	Remote Similarity	NPC476004
0.6161	Remote Similarity	NPC474761
0.6161	Remote Similarity	NPC478004
0.6161	Remote Similarity	NPC166554
0.6161	Remote Similarity	NPC158388
0.616	Remote Similarity	NPC470540
0.616	Remote Similarity	NPC476813
0.616	Remote Similarity	NPC476814
0.6154	Remote Similarity	NPC469871
0.6154	Remote Similarity	NPC107668
0.6154	Remote Similarity	NPC288876
0.6154	Remote Similarity	NPC474718
0.6154	Remote Similarity	NPC54705
0.6154	Remote Similarity	NPC469870
0.6154	Remote Similarity	NPC280498

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 NPC473252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	104
0.1-0.2	643
0.2-0.3	3661
0.3-0.4	3428
0.4-0.5	1072
0.5-0.6	214
0.6-0.7	27
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9135	High Similarity	NPD1719	Phase 1
0.6923	Remote Similarity	NPD6421	Discontinued
0.6923	Remote Similarity	NPD6420	Discontinued
0.6894	Remote Similarity	NPD6333	Approved
0.6894	Remote Similarity	NPD6334	Approved
0.6796	Remote Similarity	NPD7345	Approved
0.6789	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5779	Approved
0.6789	Remote Similarity	NPD5778	Approved
0.6757	Remote Similarity	NPD7839	Suspended
0.6733	Remote Similarity	NPD3732	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6545	Remote Similarity	NPD6411	Approved
0.6538	Remote Similarity	NPD5369	Approved
0.6512	Remote Similarity	NPD8074	Phase 3
0.6476	Remote Similarity	NPD6435	Approved
0.646	Remote Similarity	NPD4228	Discovery
0.6396	Remote Similarity	NPD7983	Approved
0.6389	Remote Similarity	NPD5786	Approved
0.6364	Remote Similarity	NPD6914	Discontinued
0.632	Remote Similarity	NPD7500	Approved
0.6303	Remote Similarity	NPD4211	Phase 1
0.6286	Remote Similarity	NPD5368	Approved
0.6281	Remote Similarity	NPD6413	Approved
0.6231	Remote Similarity	NPD8342	Approved
0.6231	Remote Similarity	NPD8341	Approved
0.6231	Remote Similarity	NPD8299	Approved
0.6231	Remote Similarity	NPD8340	Approved
0.619	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD8451	Approved
0.6168	Remote Similarity	NPD4270	Approved
0.6168	Remote Similarity	NPD4269	Approved
0.6136	Remote Similarity	NPD8448	Approved
0.6119	Remote Similarity	NPD8390	Approved
0.6119	Remote Similarity	NPD8392	Approved
0.6119	Remote Similarity	NPD8391	Approved
0.6111	Remote Similarity	NPD7154	Phase 3
0.6087	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD2204	Approved
0.6031	Remote Similarity	NPD7642	Approved
0.6016	Remote Similarity	NPD7641	Discontinued
0.6	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5363	Approved
0.5981	Remote Similarity	NPD4821	Approved
0.5981	Remote Similarity	NPD4252	Approved
0.5981	Remote Similarity	NPD4820	Approved
0.5981	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4819	Approved
0.5981	Remote Similarity	NPD4822	Approved
0.5965	Remote Similarity	NPD7637	Suspended
0.5963	Remote Similarity	NPD5362	Discontinued
0.5954	Remote Similarity	NPD8080	Discontinued
0.5952	Remote Similarity	NPD1376	Discontinued
0.5946	Remote Similarity	NPD4249	Approved
0.5943	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7830	Approved
0.5909	Remote Similarity	NPD7829	Approved
0.5893	Remote Similarity	NPD4250	Approved
0.5893	Remote Similarity	NPD4251	Approved
0.5878	Remote Similarity	NPD6908	Approved
0.5878	Remote Similarity	NPD6909	Approved
0.5877	Remote Similarity	NPD6698	Approved
0.5877	Remote Similarity	NPD46	Approved
0.5877	Remote Similarity	NPD5785	Approved
0.587	Remote Similarity	NPD4738	Phase 2
0.5841	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD8415	Approved
0.5821	Remote Similarity	NPD8273	Phase 1
0.5814	Remote Similarity	NPD7505	Discontinued
0.5797	Remote Similarity	NPD2613	Approved
0.5794	Remote Similarity	NPD4271	Approved
0.5794	Remote Similarity	NPD4268	Approved
0.5794	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD3089	Approved
0.5786	Remote Similarity	NPD2574	Discontinued
0.5786	Remote Similarity	NPD3088	Approved
0.5786	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD4746	Phase 3
0.5786	Remote Similarity	NPD2566	Approved
0.5786	Remote Similarity	NPD3616	Approved
0.5786	Remote Similarity	NPD2571	Approved
0.5786	Remote Similarity	NPD2570	Approved
0.5786	Remote Similarity	NPD3087	Approved
0.5786	Remote Similarity	NPD2573	Approved
0.5786	Remote Similarity	NPD3614	Approved
0.5786	Remote Similarity	NPD4745	Approved
0.5786	Remote Similarity	NPD3090	Approved
0.5786	Remote Similarity	NPD3615	Approved
0.5781	Remote Similarity	NPD2652	Approved
0.5781	Remote Similarity	NPD2650	Approved
0.5763	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD8516	Approved
0.5758	Remote Similarity	NPD8513	Phase 3
0.5758	Remote Similarity	NPD8515	Approved
0.5758	Remote Similarity	NPD8517	Approved
0.575	Remote Similarity	NPD6404	Discontinued
0.5748	Remote Similarity	NPD6053	Discontinued
0.5738	Remote Similarity	NPD2259	Approved
0.5738	Remote Similarity	NPD2258	Approved
0.5726	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD4685	Phase 3
0.5704	Remote Similarity	NPD4686	Approved
0.5704	Remote Similarity	NPD4684	Phase 3
0.5682	Remote Similarity	NPD6319	Approved
0.568	Remote Similarity	NPD6881	Approved
0.568	Remote Similarity	NPD6899	Approved
0.5674	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD7128	Approved
0.5645	Remote Similarity	NPD5739	Approved
0.5645	Remote Similarity	NPD6675	Approved
0.5645	Remote Similarity	NPD5357	Phase 1
0.5645	Remote Similarity	NPD6402	Approved
0.5641	Remote Similarity	NPD6399	Phase 3
0.5639	Remote Similarity	NPD5981	Approved
0.5639	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD857	Phase 3
0.5635	Remote Similarity	NPD8305	Approved
0.5635	Remote Similarity	NPD8306	Approved
0.5635	Remote Similarity	NPD6012	Approved
0.5635	Remote Similarity	NPD6013	Approved
0.5635	Remote Similarity	NPD6014	Approved
0.563	Remote Similarity	NPD2609	Approved
0.563	Remote Similarity	NPD3131	Approved
0.563	Remote Similarity	NPD4215	Approved
0.563	Remote Similarity	NPD2612	Approved
0.563	Remote Similarity	NPD3132	Approved
0.563	Remote Similarity	NPD2610	Approved
0.563	Remote Similarity	NPD4218	Approved
0.563	Remote Similarity	NPD2608	Approved
0.563	Remote Similarity	NPD4217	Approved
0.563	Remote Similarity	NPD4216	Approved
0.563	Remote Similarity	NPD2611	Approved
0.562	Remote Similarity	NPD8336	Approved
0.562	Remote Similarity	NPD8337	Approved
0.56	Remote Similarity	NPD467	Phase 1
0.56	Remote Similarity	NPD5701	Approved
0.56	Remote Similarity	NPD7899	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