NPASS Compound

Structure

NPC72715 OpenBabel07101718192D 29 33 0 0 1 0 0 0 0 0999 V2000 5.3436 -0.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0135 1.0190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5701 -5.2534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1924 1.3243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4776 0.0190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0862 0.1278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6116 -2.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4776 -1.9810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7455 -1.9810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7455 1.0190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6116 0.5190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2771 -2.2234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6207 -1.4469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4776 -0.9810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8795 0.5190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3113 -4.2875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9336 0.3584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6548 -1.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5700 -2.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0183 -1.2574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7455 -0.9810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3960 -2.6717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0523 -0.9986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6116 -0.4810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8795 -0.4810 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6223 -3.9291 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5629 -0.4188 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9406 -3.5103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 14 2 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 24 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 25 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 1 0 0 0 16 26 2 0 0 0 0 16 28 1 0 0 0 0 17 27 2 0 0 0 0 17 29 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 20 23 2 0 0 0 0 20 27 1 0 0 0 0 21 24 1 1 0 0 0 21 25 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 5 1 6 0 0 0 25 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.25
Volume:	421.929
LogP:	5.912
LogD:	4.761
LogS:	-5.479
# Rotatable Bonds:	2
TPSA:	52.06
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	4.56
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.732
MDCK Permeability:	1.729045106912963e-05
Pgp-inhibitor:	0.927
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.225

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.536
Plasma Protein Binding (PPB):	89.86412811279297%
Volume Distribution (VD):	2.881
Pgp-substrate:	5.717864513397217%

ADMET: Metabolism

CYP1A2-inhibitor:	0.629
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.244
CYP2C19-substrate:	0.213
CYP2C9-inhibitor:	0.479
CYP2C9-substrate:	0.37
CYP2D6-inhibitor:	0.167
CYP2D6-substrate:	0.293
CYP3A4-inhibitor:	0.347
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	5.164
Half-life (T1/2):	0.075

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.963
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.235
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.816
Carcinogencity:	0.753
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC72715

Natural Product ID:	NPC72715
*Common Name:**	5-Epi-Nakijinol D
IUPAC Name:	8-[[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]-2,6-dimethyl-[1,3]oxazolo[4,5-f][1,3]benzoxazole
Synonyms:
Standard InCHIKey:	UQMYTHPQNRLUNZ-UCIAGXJNSA-N
Standard InCHI:	InChI=1S/C25H32N2O2/c1-14-8-7-9-21-24(14,5)11-10-15(2)25(21,6)13-18-22-19(26-16(3)28-22)12-20-23(18)29-17(4)27-20/h8,12,15,21H,7,9-11,13H2,1-6H3/t15-,21+,24-,25+/m0/s1
SMILES:	Cc1oc2c(n1)cc1c(c2C[C@]2(C)[C@@H](C)CC[C@@]3([C@H]2CCC=C3C)C)oc(n1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109403
PubChem CID:	76324843
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000302] Benzoxazoles

*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
NPO13603	Dactylospongia metachromia	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479418]
NPO13603	Dactylospongia metachromia	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[33387695]
NPO13603	Dactylospongia metachromia	Species	Thorectidae	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
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	>	10000.0	nM	PMID[500914]

☑ 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 NPC72715 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	779
0.1-0.2	2823
0.2-0.3	11327
0.3-0.4	8314
0.4-0.5	12898
0.5-0.6	6034
0.6-0.7	459
0.7-0.8	55
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8465	Intermediate Similarity	NPC230683
0.8238	Intermediate Similarity	NPC209981
0.792	Intermediate Similarity	NPC470042
0.776	Intermediate Similarity	NPC282346
0.772	Intermediate Similarity	NPC185197
0.7719	Intermediate Similarity	NPC38237
0.7375	Intermediate Similarity	NPC140296
0.7293	Intermediate Similarity	NPC196449
0.7293	Intermediate Similarity	NPC314222
0.7269	Intermediate Similarity	NPC220408
0.7265	Intermediate Similarity	NPC474428
0.7233	Intermediate Similarity	NPC137353
0.7229	Intermediate Similarity	NPC72905
0.7208	Intermediate Similarity	NPC216612
0.72	Intermediate Similarity	NPC142385
0.7194	Intermediate Similarity	NPC203373
0.7161	Intermediate Similarity	NPC324361
0.7113	Intermediate Similarity	NPC131885
0.7107	Intermediate Similarity	NPC314633
0.7054	Intermediate Similarity	NPC120513
0.7045	Intermediate Similarity	NPC196718
0.7045	Intermediate Similarity	NPC102593
0.7019	Intermediate Similarity	NPC101312
0.6987	Remote Similarity	NPC16066
0.6983	Remote Similarity	NPC469439
0.6962	Remote Similarity	NPC269367
0.6953	Remote Similarity	NPC173250
0.6942	Remote Similarity	NPC298436
0.6932	Remote Similarity	NPC477587
0.6932	Remote Similarity	NPC477589
0.6923	Remote Similarity	NPC472589
0.6914	Remote Similarity	NPC161801
0.6914	Remote Similarity	NPC1608
0.6911	Remote Similarity	NPC472588
0.6898	Remote Similarity	NPC205372
0.6877	Remote Similarity	NPC477586
0.6877	Remote Similarity	NPC477590
0.6877	Remote Similarity	NPC477585
0.6877	Remote Similarity	NPC477588
0.6857	Remote Similarity	NPC251071
0.6853	Remote Similarity	NPC34770
0.6834	Remote Similarity	NPC67401
0.6824	Remote Similarity	NPC166712
0.6802	Remote Similarity	NPC97746
0.6797	Remote Similarity	NPC208364
0.6744	Remote Similarity	NPC58209
0.6733	Remote Similarity	NPC217176
0.6694	Remote Similarity	NPC322482
0.669	Remote Similarity	NPC207620
0.668	Remote Similarity	NPC280799
0.668	Remote Similarity	NPC168922
0.668	Remote Similarity	NPC329631
0.6667	Remote Similarity	NPC474688
0.6667	Remote Similarity	NPC288987
0.6667	Remote Similarity	NPC160100
0.6667	Remote Similarity	NPC169716
0.6667	Remote Similarity	NPC188400
0.6654	Remote Similarity	NPC119134
0.6653	Remote Similarity	NPC146418
0.664	Remote Similarity	NPC473186
0.664	Remote Similarity	NPC233334
0.664	Remote Similarity	NPC471004
0.664	Remote Similarity	NPC225279
0.6601	Remote Similarity	NPC289905
0.6601	Remote Similarity	NPC316065
0.66	Remote Similarity	NPC473449
0.6592	Remote Similarity	NPC473833
0.6588	Remote Similarity	NPC90875
0.6588	Remote Similarity	NPC39370
0.6586	Remote Similarity	NPC144452
0.656	Remote Similarity	NPC94842
0.6557	Remote Similarity	NPC473180
0.6541	Remote Similarity	NPC318068
0.6541	Remote Similarity	NPC53534
0.6529	Remote Similarity	NPC470280
0.6516	Remote Similarity	NPC187501
0.6516	Remote Similarity	NPC220337
0.6515	Remote Similarity	NPC302807
0.6513	Remote Similarity	NPC124313
0.6506	Remote Similarity	NPC215837
0.6504	Remote Similarity	NPC326930
0.6504	Remote Similarity	NPC475301
0.6504	Remote Similarity	NPC286195
0.65	Remote Similarity	NPC207283
0.65	Remote Similarity	NPC84164
0.6493	Remote Similarity	NPC129897
0.6481	Remote Similarity	NPC328928
0.648	Remote Similarity	NPC198503
0.6479	Remote Similarity	NPC478083
0.6473	Remote Similarity	NPC6786
0.6466	Remote Similarity	NPC244543
0.6463	Remote Similarity	NPC232225
0.6463	Remote Similarity	NPC39500
0.6462	Remote Similarity	NPC475844
0.6462	Remote Similarity	NPC148889
0.6457	Remote Similarity	NPC274640
0.6448	Remote Similarity	NPC166722
0.6431	Remote Similarity	NPC24019
0.6423	Remote Similarity	NPC304837
0.6423	Remote Similarity	NPC476258
0.6421	Remote Similarity	NPC471978
0.6418	Remote Similarity	NPC13603
0.6417	Remote Similarity	NPC478078
0.6415	Remote Similarity	NPC165964
0.6412	Remote Similarity	NPC15406
0.641	Remote Similarity	NPC471979
0.641	Remote Similarity	NPC227824
0.6409	Remote Similarity	NPC240384
0.6408	Remote Similarity	NPC199667
0.6407	Remote Similarity	NPC191489
0.6407	Remote Similarity	NPC89549
0.6398	Remote Similarity	NPC49672
0.6391	Remote Similarity	NPC183537
0.6386	Remote Similarity	NPC169402
0.6381	Remote Similarity	NPC53255
0.6381	Remote Similarity	NPC49547
0.6381	Remote Similarity	NPC85879
0.638	Remote Similarity	NPC172355
0.6379	Remote Similarity	NPC132751
0.6378	Remote Similarity	NPC470018
0.6375	Remote Similarity	NPC323969
0.6371	Remote Similarity	NPC116238
0.6371	Remote Similarity	NPC108342
0.637	Remote Similarity	NPC472436
0.6367	Remote Similarity	NPC473181
0.636	Remote Similarity	NPC184408
0.636	Remote Similarity	NPC46561
0.6353	Remote Similarity	NPC26543
0.6353	Remote Similarity	NPC257851
0.6353	Remote Similarity	NPC325683
0.6353	Remote Similarity	NPC74575
0.6353	Remote Similarity	NPC476828
0.6346	Remote Similarity	NPC189903
0.6346	Remote Similarity	NPC182907
0.6343	Remote Similarity	NPC471015
0.6341	Remote Similarity	NPC473639
0.6337	Remote Similarity	NPC152620
0.6335	Remote Similarity	NPC208084
0.633	Remote Similarity	NPC77878
0.633	Remote Similarity	NPC473188
0.633	Remote Similarity	NPC133609
0.6329	Remote Similarity	NPC230403
0.6328	Remote Similarity	NPC194740
0.6326	Remote Similarity	NPC180668
0.6326	Remote Similarity	NPC148896
0.6326	Remote Similarity	NPC471013
0.6324	Remote Similarity	NPC210434
0.6316	Remote Similarity	NPC270515
0.6314	Remote Similarity	NPC100734
0.6314	Remote Similarity	NPC88923
0.6314	Remote Similarity	NPC37924
0.6314	Remote Similarity	NPC315634
0.6312	Remote Similarity	NPC124300
0.6311	Remote Similarity	NPC45190
0.6311	Remote Similarity	NPC300156
0.6308	Remote Similarity	NPC473187
0.6302	Remote Similarity	NPC120239
0.6298	Remote Similarity	NPC475816
0.6298	Remote Similarity	NPC41501
0.6295	Remote Similarity	NPC309919
0.6293	Remote Similarity	NPC141053
0.6292	Remote Similarity	NPC10904
0.629	Remote Similarity	NPC310211
0.629	Remote Similarity	NPC308137
0.6288	Remote Similarity	NPC291609
0.6286	Remote Similarity	NPC321428
0.6286	Remote Similarity	NPC193238
0.6282	Remote Similarity	NPC288854
0.6279	Remote Similarity	NPC474701
0.6278	Remote Similarity	NPC475315
0.6278	Remote Similarity	NPC17437
0.6278	Remote Similarity	NPC324619
0.6275	Remote Similarity	NPC470020
0.6275	Remote Similarity	NPC477219
0.6273	Remote Similarity	NPC258048
0.6272	Remote Similarity	NPC471303
0.6269	Remote Similarity	NPC476220
0.6269	Remote Similarity	NPC160113
0.6265	Remote Similarity	NPC236668
0.6261	Remote Similarity	NPC475190
0.6261	Remote Similarity	NPC315631
0.626	Remote Similarity	NPC131486
0.6259	Remote Similarity	NPC478080
0.6259	Remote Similarity	NPC472435
0.6255	Remote Similarity	NPC223189
0.6255	Remote Similarity	NPC322800
0.6255	Remote Similarity	NPC168135
0.625	Remote Similarity	NPC473540
0.625	Remote Similarity	NPC113455
0.6245	Remote Similarity	NPC174760
0.6245	Remote Similarity	NPC189079
0.6245	Remote Similarity	NPC150239
0.6245	Remote Similarity	NPC70340
0.6241	Remote Similarity	NPC310618
0.6241	Remote Similarity	NPC475533
0.624	Remote Similarity	NPC146976
0.624	Remote Similarity	NPC278525
0.6235	Remote Similarity	NPC51388
0.6235	Remote Similarity	NPC476826
0.6235	Remote Similarity	NPC476831

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 NPC72715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	432
0.1-0.2	636
0.2-0.3	1133
0.3-0.4	2397
0.4-0.5	2958
0.5-0.6	1412
0.6-0.7	173
0.7-0.8	9
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
0.7543	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD2778	Approved
0.7382	Intermediate Similarity	NPD3945	Discontinued
0.7373	Intermediate Similarity	NPD6974	Phase 3
0.7325	Intermediate Similarity	NPD2779	Approved
0.7314	Intermediate Similarity	NPD5924	Discontinued
0.7288	Intermediate Similarity	NPD5443	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD5850	Phase 3
0.722	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1505	Phase 2
0.7143	Intermediate Similarity	NPD1867	Approved
0.7126	Intermediate Similarity	NPD2951	Discontinued
0.7106	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3250	Phase 1
0.7034	Intermediate Similarity	NPD2081	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7417	Discontinued
0.6827	Remote Similarity	NPD5479	Discontinued
0.6827	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3507	Phase 2
0.6781	Remote Similarity	NPD772	Phase 3
0.6761	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3392	Approved
0.6721	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7180	Phase 3
0.6707	Remote Similarity	NPD3263	Phase 3
0.6693	Remote Similarity	NPD7853	Phase 2
0.668	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3809	Discontinued
0.6653	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7031	Phase 1
0.6639	Remote Similarity	NPD5293	Phase 2
0.6628	Remote Similarity	NPD6716	Phase 1
0.6615	Remote Similarity	NPD5817	Discontinued
0.6611	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6104	Discontinued
0.6598	Remote Similarity	NPD7467	Discontinued
0.6591	Remote Similarity	NPD5532	Phase 2
0.6576	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1955	Discontinued
0.6564	Remote Similarity	NPD4322	Discontinued
0.6564	Remote Similarity	NPD7022	Phase 2
0.6559	Remote Similarity	NPD4429	Discontinued
0.6555	Remote Similarity	NPD6321	Discontinued
0.6555	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6745	Discontinued
0.6537	Remote Similarity	NPD4368	Phase 2
0.6535	Remote Similarity	NPD1466	Phase 3
0.6535	Remote Similarity	NPD1467	Approved
0.652	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.652	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD8357	Approved
0.6518	Remote Similarity	NPD6719	Approved
0.6515	Remote Similarity	NPD6245	Phase 2
0.6498	Remote Similarity	NPD3006	Discontinued
0.6496	Remote Similarity	NPD5022	Discontinued
0.6494	Remote Similarity	NPD7279	Phase 2
0.6494	Remote Similarity	NPD7278	Phase 2
0.6491	Remote Similarity	NPD5857	Phase 3
0.649	Remote Similarity	NPD5866	Approved
0.6483	Remote Similarity	NPD5512	Phase 3
0.6462	Remote Similarity	NPD6790	Phase 1
0.6455	Remote Similarity	NPD8461	Discontinued
0.6449	Remote Similarity	NPD6220	Phase 3
0.6449	Remote Similarity	NPD5416	Discontinued
0.6449	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1898	Discontinued
0.6437	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD4952	Phase 3
0.6431	Remote Similarity	NPD1659	Phase 1
0.6426	Remote Similarity	NPD7395	Discontinued
0.642	Remote Similarity	NPD5429	Discontinued
0.6415	Remote Similarity	NPD5482	Discontinued
0.6412	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6530	Approved
0.6407	Remote Similarity	NPD6531	Approved
0.6407	Remote Similarity	NPD7708	Approved
0.6405	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD7206	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7924	Phase 2
0.6387	Remote Similarity	NPD7925	Phase 2
0.6379	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD3257	Approved
0.6371	Remote Similarity	NPD1638	Discovery
0.6364	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.636	Remote Similarity	NPD5632	Approved
0.636	Remote Similarity	NPD7886	Phase 2
0.636	Remote Similarity	NPD7885	Phase 2
0.6357	Remote Similarity	NPD4373	Phase 2
0.6353	Remote Similarity	NPD6475	Phase 2
0.6352	Remote Similarity	NPD7043	Discontinued
0.6348	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4846	Phase 2
0.6345	Remote Similarity	NPD6550	Discontinued
0.6339	Remote Similarity	NPD3925	Approved
0.6335	Remote Similarity	NPD3258	Approved
0.6333	Remote Similarity	NPD6874	Approved
0.6328	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6209	Approved
0.6314	Remote Similarity	NPD7803	Approved
0.631	Remote Similarity	NPD6242	Discontinued
0.6302	Remote Similarity	NPD5488	Discontinued
0.6298	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD6568	Discontinued
0.6289	Remote Similarity	NPD7994	Phase 2
0.6285	Remote Similarity	NPD4923	Phase 1
0.6283	Remote Similarity	NPD8463	Approved
0.6279	Remote Similarity	NPD7688	Phase 1
0.6278	Remote Similarity	NPD8358	Approved
0.6275	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.627	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6376	Discontinued
0.6255	Remote Similarity	NPD4989	Phase 2
0.625	Remote Similarity	NPD7392	Phase 2
0.625	Remote Similarity	NPD7490	Discontinued
0.6236	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD8016	Phase 3
0.623	Remote Similarity	NPD6198	Phase 1
0.623	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4328	Approved
0.6221	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6208	Remote Similarity	NPD6347	Phase 2
0.6206	Remote Similarity	NPD2884	Phase 1
0.6201	Remote Similarity	NPD5922	Phase 3
0.6194	Remote Similarity	NPD3853	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.6189	Remote Similarity	NPD1483	Discontinued
0.618	Remote Similarity	NPD8100	Phase 3
0.6179	Remote Similarity	NPD5499	Approved
0.6175	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD6169	Phase 1
0.6174	Remote Similarity	NPD4613	Phase 2
0.6166	Remote Similarity	NPD1926	Approved
0.6163	Remote Similarity	NPD5513	Phase 2
0.6163	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6962	Phase 2
0.6154	Remote Similarity	NPD8067	Phase 3
0.6151	Remote Similarity	NPD9243	Approved
0.6148	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD5256	Discontinued
0.6142	Remote Similarity	NPD3875	Discontinued
0.6138	Remote Similarity	NPD4465	Phase 2
0.6138	Remote Similarity	NPD4467	Phase 2
0.6137	Remote Similarity	NPD5450	Discontinued
0.6134	Remote Similarity	NPD8102	Discontinued
0.6134	Remote Similarity	NPD4369	Phase 2
0.6131	Remote Similarity	NPD7955	Approved
0.6131	Remote Similarity	NPD7956	Approved
0.613	Remote Similarity	NPD3746	Discontinued
0.6124	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5640	Discontinued
0.6124	Remote Similarity	NPD7051	Phase 3
0.6122	Remote Similarity	NPD7627	Approved
0.6122	Remote Similarity	NPD7626	Approved
0.6116	Remote Similarity	NPD5003	Discontinued
0.6115	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD7673	Phase 3
0.6113	Remote Similarity	NPD8403	Phase 1
0.6111	Remote Similarity	NPD8101	Phase 3
0.6107	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7592	Phase 2
0.6103	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7292	Approved
0.61	Remote Similarity	NPD4418	Discontinued
0.61	Remote Similarity	NPD3259	Approved
0.6096	Remote Similarity	NPD7069	Discontinued
0.6089	Remote Similarity	NPD7452	Approved
0.6089	Remote Similarity	NPD7222	Phase 2
0.6089	Remote Similarity	NPD7453	Approved
0.6085	Remote Similarity	NPD7681	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD7654	Discontinued
0.6075	Remote Similarity	NPD6825	Phase 1
0.607	Remote Similarity	NPD6995	Phase 1
0.6063	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8479	Phase 2
0.6054	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5459	Phase 2
0.605	Remote Similarity	NPD6393	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