NPASS Compound

Structure

NPC147707 OpenBabel07101718242D 26 27 0 0 1 0 0 0 0 0999 V2000 3.6246 -4.7382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1085 -6.3266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3894 -2.2558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8665 -0.3244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7904 -4.1422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9909 -5.0854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8733 -3.8442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2443 -2.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3612 -1.7708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3612 0.1577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4254 0.6346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9080 -5.3834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6728 -2.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8665 -1.2887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1963 -1.2887 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1963 -0.3244 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5262 -1.2887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6452 -0.7166 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4821 0.8351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5262 -0.3244 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0314 -1.7708 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7016 -1.7708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0314 0.1577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6911 -1.7708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0899 1.7160 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 15 1 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 14 21 2 3 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 1 0 0 0 16 23 1 1 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 6 0 0 0 18 26 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 20 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	363.2
Volume:	379.129
LogP:	1.945
LogD:	1.744
LogS:	-3.794
# Rotatable Bonds:	6
TPSA:	92.7
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.577
Synthetic Accessibility Score:	4.982
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.946
MDCK Permeability:	1.1665032616292592e-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.914
20% Bioavailability (F20%):	0.839
30% Bioavailability (F30%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.812
Plasma Protein Binding (PPB):	75.28399658203125%
Volume Distribution (VD):	0.934
Pgp-substrate:	16.244516372680664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.354
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.197
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.254
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	5.508
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.589
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.265
Rat Oral Acute Toxicity:	0.526
Maximum Recommended Daily Dose:	0.141
Skin Sensitization:	0.352
Carcinogencity:	0.099
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC147707

Natural Product ID:	NPC147707
*Common Name:**	(+)-Miliusane V
IUPAC Name:	N-[(1R,5R,8R,9S)-1-[(1E)-2,6-dimethylhepta-1,5-dienyl]-9-hydroxy-3,6-dioxo-2-oxaspiro[4.5]decan-8-yl]acetamide
Synonyms:	(+)-Miliusane V
Standard InCHIKey:	IFURIYNUZYASFB-ROJMHPMNSA-N
Standard InCHI:	InChI=1S/C20H29NO5/c1-12(2)6-5-7-13(3)8-18-20(11-19(25)26-18)10-16(23)15(9-17(20)24)21-14(4)22/h6,8,15-16,18,23H,5,7,9-11H2,1-4H3,(H,21,22)/b13-8+/t15-,16+,18-,20+/m1/s1
SMILES:	C/C(=C[C@H]1OC(=O)C[C@@]21C[C@H](O)[C@@H](CC2=O)N=C(O)C)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL201503
PubChem CID:	11624740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO22093	Miliusa sinensis	Species	Annonaceae	Eukaryota	dried leaves, twigs, and flowers	Vietnam	n.a.	PMID[16420055]
NPO22093	Miliusa sinensis	Species	Annonaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	55000.0	nM	PMID[483069]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	>	55000.0	nM	PMID[483069]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	>	55000.0	nM	PMID[483069]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	55000.0	nM	PMID[483069]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	55000.0	nM	PMID[483069]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	52290.0	nM	PMID[483069]

☑ 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 NPC147707 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	93
0.1-0.2	624
0.2-0.3	2988
0.3-0.4	16484
0.4-0.5	13168
0.5-0.6	8362
0.6-0.7	962
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7658	Intermediate Similarity	NPC21302
0.7658	Intermediate Similarity	NPC11396
0.7589	Intermediate Similarity	NPC17326
0.7589	Intermediate Similarity	NPC134454
0.748	Intermediate Similarity	NPC9714
0.7297	Intermediate Similarity	NPC207641
0.7297	Intermediate Similarity	NPC233437
0.7287	Intermediate Similarity	NPC204556
0.7167	Intermediate Similarity	NPC70235
0.7099	Intermediate Similarity	NPC329919
0.7099	Intermediate Similarity	NPC477793
0.6985	Remote Similarity	NPC472430
0.6975	Remote Similarity	NPC215988
0.6917	Remote Similarity	NPC471471
0.6917	Remote Similarity	NPC164476
0.6903	Remote Similarity	NPC473455
0.6829	Remote Similarity	NPC474725
0.6814	Remote Similarity	NPC87306
0.681	Remote Similarity	NPC214694
0.6803	Remote Similarity	NPC475800
0.6791	Remote Similarity	NPC121601
0.6788	Remote Similarity	NPC472428
0.6786	Remote Similarity	NPC473248
0.6777	Remote Similarity	NPC119329
0.6744	Remote Similarity	NPC35037
0.6724	Remote Similarity	NPC250075
0.6721	Remote Similarity	NPC271269
0.6694	Remote Similarity	NPC110989
0.6667	Remote Similarity	NPC82931
0.6667	Remote Similarity	NPC210729
0.6667	Remote Similarity	NPC172365
0.6639	Remote Similarity	NPC203659
0.6639	Remote Similarity	NPC23364
0.6622	Remote Similarity	NPC265699
0.6619	Remote Similarity	NPC145899
0.6613	Remote Similarity	NPC475150
0.6612	Remote Similarity	NPC225353
0.6607	Remote Similarity	NPC155873
0.6594	Remote Similarity	NPC76999
0.6585	Remote Similarity	NPC469607
0.6585	Remote Similarity	NPC154601
0.6585	Remote Similarity	NPC473252
0.6583	Remote Similarity	NPC306856
0.6583	Remote Similarity	NPC473224
0.6583	Remote Similarity	NPC474718
0.6579	Remote Similarity	NPC202672
0.6579	Remote Similarity	NPC153570
0.6577	Remote Similarity	NPC52923
0.6577	Remote Similarity	NPC187497
0.6577	Remote Similarity	NPC100612
0.6577	Remote Similarity	NPC174336
0.6577	Remote Similarity	NPC113620
0.6577	Remote Similarity	NPC475599
0.656	Remote Similarity	NPC218602
0.6557	Remote Similarity	NPC469895
0.6557	Remote Similarity	NPC474775
0.6555	Remote Similarity	NPC70145
0.6555	Remote Similarity	NPC91695
0.6555	Remote Similarity	NPC474343
0.6552	Remote Similarity	NPC30515
0.6552	Remote Similarity	NPC314500
0.6547	Remote Similarity	NPC75318
0.6541	Remote Similarity	NPC280498
0.6538	Remote Similarity	NPC476952
0.6532	Remote Similarity	NPC251330
0.6532	Remote Similarity	NPC230541
0.6532	Remote Similarity	NPC271562
0.6529	Remote Similarity	NPC472753
0.6529	Remote Similarity	NPC171759
0.6528	Remote Similarity	NPC475892
0.6525	Remote Similarity	NPC243680
0.6525	Remote Similarity	NPC200788
0.6522	Remote Similarity	NPC78008
0.6522	Remote Similarity	NPC295312
0.6518	Remote Similarity	NPC38569
0.6518	Remote Similarity	NPC163615
0.6515	Remote Similarity	NPC23963
0.651	Remote Similarity	NPC475527
0.6508	Remote Similarity	NPC478209
0.6504	Remote Similarity	NPC14537
0.65	Remote Similarity	NPC234542
0.65	Remote Similarity	NPC141191
0.6496	Remote Similarity	NPC179746
0.6496	Remote Similarity	NPC475912
0.6496	Remote Similarity	NPC81419
0.6484	Remote Similarity	NPC9848
0.6484	Remote Similarity	NPC312017
0.648	Remote Similarity	NPC476802
0.648	Remote Similarity	NPC89171
0.648	Remote Similarity	NPC189075
0.648	Remote Similarity	NPC275539
0.6475	Remote Similarity	NPC469606
0.6475	Remote Similarity	NPC478156
0.6475	Remote Similarity	NPC474709
0.6475	Remote Similarity	NPC273005
0.6475	Remote Similarity	NPC472754
0.6475	Remote Similarity	NPC31058
0.6471	Remote Similarity	NPC185553
0.6471	Remote Similarity	NPC473859
0.6471	Remote Similarity	NPC476957
0.6466	Remote Similarity	NPC106510
0.6466	Remote Similarity	NPC51004
0.6466	Remote Similarity	NPC158488
0.6466	Remote Similarity	NPC71533
0.6466	Remote Similarity	NPC232202
0.6458	Remote Similarity	NPC475152
0.6458	Remote Similarity	NPC475394
0.6458	Remote Similarity	NPC475584
0.6452	Remote Similarity	NPC478208
0.6449	Remote Similarity	NPC139585
0.6449	Remote Similarity	NPC475472
0.6446	Remote Similarity	NPC117685
0.6446	Remote Similarity	NPC288876
0.6441	Remote Similarity	NPC81386
0.6441	Remote Similarity	NPC474035
0.6434	Remote Similarity	NPC117712
0.6429	Remote Similarity	NPC474243
0.6429	Remote Similarity	NPC141350
0.6429	Remote Similarity	NPC42662
0.6423	Remote Similarity	NPC4620
0.6423	Remote Similarity	NPC474165
0.6423	Remote Similarity	NPC472755
0.6423	Remote Similarity	NPC475871
0.6423	Remote Similarity	NPC69171
0.6423	Remote Similarity	NPC475945
0.6423	Remote Similarity	NPC475321
0.6417	Remote Similarity	NPC4834
0.6417	Remote Similarity	NPC476344
0.6417	Remote Similarity	NPC169205
0.6414	Remote Similarity	NPC193753
0.6414	Remote Similarity	NPC160222
0.6412	Remote Similarity	NPC470276
0.641	Remote Similarity	NPC20713
0.641	Remote Similarity	NPC208886
0.641	Remote Similarity	NPC12172
0.641	Remote Similarity	NPC184463
0.6406	Remote Similarity	NPC469865
0.6403	Remote Similarity	NPC73829
0.6403	Remote Similarity	NPC119794
0.64	Remote Similarity	NPC110496
0.6397	Remote Similarity	NPC476951
0.6393	Remote Similarity	NPC475099
0.6393	Remote Similarity	NPC471412
0.6391	Remote Similarity	NPC242692
0.6387	Remote Similarity	NPC90121
0.6387	Remote Similarity	NPC36954
0.6387	Remote Similarity	NPC275960
0.6387	Remote Similarity	NPC150041
0.6387	Remote Similarity	NPC475659
0.6387	Remote Similarity	NPC14961
0.6387	Remote Similarity	NPC48803
0.6387	Remote Similarity	NPC193645
0.6387	Remote Similarity	NPC471142
0.6387	Remote Similarity	NPC270013
0.6385	Remote Similarity	NPC476710
0.6385	Remote Similarity	NPC476711
0.6379	Remote Similarity	NPC307411
0.6379	Remote Similarity	NPC474032
0.6378	Remote Similarity	NPC472666
0.6372	Remote Similarity	NPC219966
0.6371	Remote Similarity	NPC472756
0.6371	Remote Similarity	NPC258532
0.6371	Remote Similarity	NPC100487
0.6371	Remote Similarity	NPC475676
0.6371	Remote Similarity	NPC239162
0.6371	Remote Similarity	NPC220964
0.6364	Remote Similarity	NPC216478
0.6357	Remote Similarity	NPC478212
0.6357	Remote Similarity	NPC120420
0.6356	Remote Similarity	NPC475302
0.6356	Remote Similarity	NPC476300
0.6356	Remote Similarity	NPC212486
0.6356	Remote Similarity	NPC199543
0.635	Remote Similarity	NPC477352
0.6349	Remote Similarity	NPC322903
0.6349	Remote Similarity	NPC94377
0.6341	Remote Similarity	NPC164551
0.6341	Remote Similarity	NPC149371
0.6341	Remote Similarity	NPC474747
0.6341	Remote Similarity	NPC162973
0.6341	Remote Similarity	NPC183571
0.6341	Remote Similarity	NPC235369
0.6338	Remote Similarity	NPC230889
0.6336	Remote Similarity	NPC476712
0.6336	Remote Similarity	NPC98249
0.6336	Remote Similarity	NPC476190
0.6336	Remote Similarity	NPC53396
0.6336	Remote Similarity	NPC469684
0.6336	Remote Similarity	NPC476713
0.6333	Remote Similarity	NPC142529
0.6333	Remote Similarity	NPC202833
0.6333	Remote Similarity	NPC126156
0.6333	Remote Similarity	NPC91771
0.6333	Remote Similarity	NPC476315
0.6333	Remote Similarity	NPC230800
0.6328	Remote Similarity	NPC21713
0.6328	Remote Similarity	NPC188738
0.6328	Remote Similarity	NPC475608
0.6325	Remote Similarity	NPC474761
0.6325	Remote Similarity	NPC51486

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 NPC147707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	90
0.1-0.2	525
0.2-0.3	2888
0.3-0.4	3825
0.4-0.5	1413
0.5-0.6	375
0.6-0.7	34
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
0.664	Remote Similarity	NPD6421	Discontinued
0.6579	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2258	Approved
0.6557	Remote Similarity	NPD2259	Approved
0.6525	Remote Similarity	NPD6333	Approved
0.6525	Remote Similarity	NPD6334	Approved
0.6387	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6914	Discontinued
0.6333	Remote Similarity	NPD4228	Discovery
0.6324	Remote Similarity	NPD8451	Approved
0.6312	Remote Similarity	NPD8415	Approved
0.6299	Remote Similarity	NPD6413	Approved
0.6296	Remote Similarity	NPD7642	Approved
0.6277	Remote Similarity	NPD8074	Phase 3
0.6277	Remote Similarity	NPD8448	Approved
0.6269	Remote Similarity	NPD8444	Approved
0.625	Remote Similarity	NPD6420	Discontinued
0.6218	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6921	Approved
0.6143	Remote Similarity	NPD8390	Approved
0.6143	Remote Similarity	NPD8392	Approved
0.6143	Remote Similarity	NPD8391	Approved
0.6131	Remote Similarity	NPD8299	Approved
0.6131	Remote Similarity	NPD8342	Approved
0.6131	Remote Similarity	NPD8340	Approved
0.6131	Remote Similarity	NPD8341	Approved
0.6107	Remote Similarity	NPD1376	Discontinued
0.6087	Remote Similarity	NPD8273	Phase 1
0.6083	Remote Similarity	NPD5778	Approved
0.6083	Remote Similarity	NPD5779	Approved
0.6077	Remote Similarity	NPD2204	Approved
0.6077	Remote Similarity	NPD1719	Phase 1
0.6066	Remote Similarity	NPD7839	Suspended
0.6065	Remote Similarity	NPD8414	Discontinued
0.6058	Remote Similarity	NPD7830	Approved
0.6058	Remote Similarity	NPD7829	Approved
0.6054	Remote Similarity	NPD8384	Approved
0.6045	Remote Similarity	NPD7641	Discontinued
0.6034	Remote Similarity	NPD619	Phase 3
0.6029	Remote Similarity	NPD8269	Approved
0.6029	Remote Similarity	NPD8268	Approved
0.6029	Remote Similarity	NPD8267	Approved
0.6029	Remote Similarity	NPD8266	Approved
0.6	Remote Similarity	NPD7983	Approved
0.6	Remote Similarity	NPD6371	Approved
0.5983	Remote Similarity	NPD5786	Approved
0.597	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.597	Remote Similarity	NPD7500	Approved
0.5968	Remote Similarity	NPD4225	Approved
0.5968	Remote Similarity	NPD7638	Approved
0.5938	Remote Similarity	NPD4211	Phase 1
0.592	Remote Similarity	NPD7639	Approved
0.592	Remote Similarity	NPD8418	Phase 2
0.592	Remote Similarity	NPD7640	Approved
0.5917	Remote Similarity	NPD5785	Approved
0.5917	Remote Similarity	NPD6698	Approved
0.5917	Remote Similarity	NPD46	Approved
0.5913	Remote Similarity	NPD7345	Approved
0.5912	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5282	Discontinued
0.5897	Remote Similarity	NPD1694	Approved
0.5874	Remote Similarity	NPD7260	Phase 2
0.587	Remote Similarity	NPD8080	Discontinued
0.5868	Remote Similarity	NPD6411	Approved
0.5846	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD6686	Approved
0.5833	Remote Similarity	NPD6845	Suspended
0.5826	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.582	Remote Similarity	NPD6399	Phase 3
0.5806	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD6908	Approved
0.5797	Remote Similarity	NPD6909	Approved
0.5769	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7518	Approved
0.5766	Remote Similarity	NPD7517	Approved
0.5766	Remote Similarity	NPD7519	Approved
0.5725	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD7147	Phase 3
0.5724	Remote Similarity	NPD2613	Approved
0.5702	Remote Similarity	NPD6101	Approved
0.5702	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD6008	Approved
0.5683	Remote Similarity	NPD8517	Approved
0.5683	Remote Similarity	NPD8515	Approved
0.5683	Remote Similarity	NPD8513	Phase 3
0.5683	Remote Similarity	NPD8516	Approved
0.5682	Remote Similarity	NPD6373	Approved
0.5682	Remote Similarity	NPD6372	Approved
0.5663	Remote Similarity	NPD7315	Approved
0.5641	Remote Similarity	NPD4270	Approved
0.5641	Remote Similarity	NPD4269	Approved
0.5641	Remote Similarity	NPD6435	Approved
0.5641	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD7902	Approved
0.563	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7319	Approved
0.562	Remote Similarity	NPD618	Clinical (unspecified phase)
0.562	Remote Similarity	NPD7115	Discovery
0.5612	Remote Similarity	NPD6319	Approved
0.561	Remote Similarity	NPD7637	Suspended
0.5608	Remote Similarity	NPD4745	Approved
0.5608	Remote Similarity	NPD4746	Phase 3
0.5608	Remote Similarity	NPD3616	Approved
0.5608	Remote Similarity	NPD2571	Approved
0.5608	Remote Similarity	NPD2566	Approved
0.5608	Remote Similarity	NPD3090	Approved
0.5608	Remote Similarity	NPD3089	Approved
0.5608	Remote Similarity	NPD2574	Discontinued
0.5608	Remote Similarity	NPD2573	Approved
0.5608	Remote Similarity	NPD3614	Approved
0.5608	Remote Similarity	NPD3615	Approved
0.5608	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5608	Remote Similarity	NPD3087	Approved
0.5608	Remote Similarity	NPD3088	Approved
0.5608	Remote Similarity	NPD2570	Approved
0.5603	Remote Similarity	NPD7604	Phase 2

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