NPASS Compound

Structure

CID96406 OpenBabel06191715432D 26 28 0 0 0 0 0 0 0 0999 V2000 5.4041 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2701 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1361 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0021 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8682 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1002 -5.5170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1002 -5.5170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7342 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4092 -4.5659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7912 -4.5659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6002 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6002 -3.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.4662 -2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 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 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 11 2 0 0 0 0 8 12 2 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 23 1 0 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.21
Volume:	384.947
LogP:	4.981
LogD:	3.996
LogS:	-5.428
# Rotatable Bonds:	10
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	2.454
Fsp3:	0.5
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:	-4.831
MDCK Permeability:	2.9335558792809024e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.295

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246
Plasma Protein Binding (PPB):	97.921142578125%
Volume Distribution (VD):	1.062
Pgp-substrate:	1.4879378080368042%

ADMET: Metabolism

CYP1A2-inhibitor:	0.949
CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	0.899
CYP2C19-substrate:	0.236
CYP2C9-inhibitor:	0.578
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	7.656
Half-life (T1/2):	0.349

ADMET: Toxicity

hERG Blockers:	0.944
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.232
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.269
Skin Sensitization:	0.973
Carcinogencity:	0.603
Eye Corrosion:	0.096
Eye Irritation:	0.366
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC96406

Natural Product ID:	NPC96406
*Common Name:**	11-(Benzo[D][1,3]Dioxol-5-Yl)-1-(Pyrrolidin-1-Yl)Undeca-2,10-Dien-1-One
IUPAC Name:	(2E,10E)-11-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylundeca-2,10-dien-1-one
Synonyms:
Standard InCHIKey:	VZDKNTSKFORBBF-MKICQXMISA-N
Standard InCHI:	InChI=1S/C22H29NO3/c24-22(23-15-9-10-16-23)12-8-6-4-2-1-3-5-7-11-19-13-14-20-21(17-19)26-18-25-20/h7-8,11-14,17H,1-6,9-10,15-16,18H2/b11-7+,12-8+
SMILES:	C(CCC/C=C/C(=O)N1CCCC1)CC/C=C/c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338736
PubChem CID:	10760681
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	whole plant	Luxi County, Yunnan Province, China	2008-OCT	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	8
Others	1

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	27550.0	nM	PMID[448957]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	30680.0	nM	PMID[448957]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	=	36890.0	nM	PMID[448957]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[448957]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[448957]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	23180.0	nM	PMID[448957]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	27320.0	nM	PMID[448957]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20870.0	nM	PMID[448957]
NPT2	Others	Unspecified		Ratio IC50	=	1.3	n.a.	PMID[448957]

☑ 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 NPC96406 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	245
0.1-0.2	1545
0.2-0.3	7219
0.3-0.4	11501
0.4-0.5	6776
0.5-0.6	12231
0.6-0.7	2828
0.7-0.8	314
0.8-0.85	7
0.85-0.9	3
0.9-0.95	16
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC137172
0.9922	High Similarity	NPC145446
0.9921	High Similarity	NPC328419
0.9921	High Similarity	NPC193673
0.9921	High Similarity	NPC45783
0.9921	High Similarity	NPC103947
0.9921	High Similarity	NPC94280
0.9921	High Similarity	NPC159150
0.9845	High Similarity	NPC95366
0.9845	High Similarity	NPC248505
0.9764	High Similarity	NPC217574
0.9466	High Similarity	NPC99078
0.9457	High Similarity	NPC318862
0.9394	High Similarity	NPC220923
0.9394	High Similarity	NPC252107
0.9389	High Similarity	NPC255817
0.9389	High Similarity	NPC205178
0.9389	High Similarity	NPC196609
0.9389	High Similarity	NPC136330
0.9389	High Similarity	NPC73883
0.9389	High Similarity	NPC251454
0.9389	High Similarity	NPC277042
0.9389	High Similarity	NPC230698
0.9313	High Similarity	NPC167096
0.9248	High Similarity	NPC470707
0.9248	High Similarity	NPC28641
0.9248	High Similarity	NPC194359
0.8824	High Similarity	NPC225745
0.8815	High Similarity	NPC180647
0.875	High Similarity	NPC469808
0.8582	High Similarity	NPC244338
0.8493	Intermediate Similarity	NPC471073
0.8493	Intermediate Similarity	NPC270811
0.8378	Intermediate Similarity	NPC169742
0.8357	Intermediate Similarity	NPC231572
0.8188	Intermediate Similarity	NPC470708
0.8168	Intermediate Similarity	NPC69670
0.8156	Intermediate Similarity	NPC113236
0.8156	Intermediate Similarity	NPC214036
0.8138	Intermediate Similarity	NPC469978
0.8108	Intermediate Similarity	NPC223125
0.8077	Intermediate Similarity	NPC111225
0.8015	Intermediate Similarity	NPC199209
0.8015	Intermediate Similarity	NPC212643
0.8	Intermediate Similarity	NPC223124
0.8	Intermediate Similarity	NPC231198
0.7985	Intermediate Similarity	NPC114845
0.7956	Intermediate Similarity	NPC251466
0.7956	Intermediate Similarity	NPC156944
0.7933	Intermediate Similarity	NPC474852
0.7929	Intermediate Similarity	NPC118419
0.7926	Intermediate Similarity	NPC256167
0.7919	Intermediate Similarity	NPC470088
0.7899	Intermediate Similarity	NPC291449
0.7899	Intermediate Similarity	NPC99798
0.7899	Intermediate Similarity	NPC191302
0.7899	Intermediate Similarity	NPC41331
0.7899	Intermediate Similarity	NPC157740
0.7895	Intermediate Similarity	NPC57501
0.7891	Intermediate Similarity	NPC31279
0.7883	Intermediate Similarity	NPC71105
0.7883	Intermediate Similarity	NPC152186
0.7883	Intermediate Similarity	NPC182147
0.7883	Intermediate Similarity	NPC170583
0.7883	Intermediate Similarity	NPC207541
0.7883	Intermediate Similarity	NPC246133
0.7842	Intermediate Similarity	NPC147247
0.7842	Intermediate Similarity	NPC469977
0.7842	Intermediate Similarity	NPC246974
0.7832	Intermediate Similarity	NPC7018
0.7832	Intermediate Similarity	NPC416184
0.7826	Intermediate Similarity	NPC218323
0.7817	Intermediate Similarity	NPC473463
0.7812	Intermediate Similarity	NPC127326
0.781	Intermediate Similarity	NPC300955
0.7786	Intermediate Similarity	NPC470706
0.777	Intermediate Similarity	NPC64948
0.777	Intermediate Similarity	NPC172403
0.7762	Intermediate Similarity	NPC11147
0.7721	Intermediate Similarity	NPC301641
0.7721	Intermediate Similarity	NPC80241
0.7692	Intermediate Similarity	NPC284855
0.7692	Intermediate Similarity	NPC282477
0.7662	Intermediate Similarity	NPC78733
0.7662	Intermediate Similarity	NPC76079
0.7655	Intermediate Similarity	NPC193528
0.7628	Intermediate Similarity	NPC106786
0.7626	Intermediate Similarity	NPC85830
0.7616	Intermediate Similarity	NPC475959
0.7595	Intermediate Similarity	NPC59567
0.7591	Intermediate Similarity	NPC193484
0.7574	Intermediate Similarity	NPC344161
0.7536	Intermediate Similarity	NPC298486
0.7535	Intermediate Similarity	NPC476748
0.7534	Intermediate Similarity	NPC230968
0.7534	Intermediate Similarity	NPC102260
0.7533	Intermediate Similarity	NPC145304
0.7532	Intermediate Similarity	NPC148898
0.7532	Intermediate Similarity	NPC210148
0.7532	Intermediate Similarity	NPC233029
0.7518	Intermediate Similarity	NPC286683
0.7517	Intermediate Similarity	NPC475828
0.7516	Intermediate Similarity	NPC86469
0.7516	Intermediate Similarity	NPC241055
0.75	Intermediate Similarity	NPC31311
0.75	Intermediate Similarity	NPC266425
0.75	Intermediate Similarity	NPC234392
0.7483	Intermediate Similarity	NPC477694
0.7483	Intermediate Similarity	NPC477705
0.7483	Intermediate Similarity	NPC166184
0.7481	Intermediate Similarity	NPC179309
0.7468	Intermediate Similarity	NPC215829
0.7468	Intermediate Similarity	NPC97072
0.7451	Intermediate Similarity	NPC469540
0.7451	Intermediate Similarity	NPC469539
0.7447	Intermediate Similarity	NPC213711
0.7447	Intermediate Similarity	NPC40352
0.7439	Intermediate Similarity	NPC308267
0.7432	Intermediate Similarity	NPC178290
0.7431	Intermediate Similarity	NPC477706
0.7426	Intermediate Similarity	NPC277460
0.7425	Intermediate Similarity	NPC102760
0.7415	Intermediate Similarity	NPC254610
0.7413	Intermediate Similarity	NPC160193
0.7407	Intermediate Similarity	NPC268317
0.7396	Intermediate Similarity	NPC471650
0.7394	Intermediate Similarity	NPC158737
0.7394	Intermediate Similarity	NPC177167
0.7388	Intermediate Similarity	NPC294941
0.7383	Intermediate Similarity	NPC275150
0.7383	Intermediate Similarity	NPC278076
0.7381	Intermediate Similarity	NPC83511
0.7376	Intermediate Similarity	NPC120066
0.7372	Intermediate Similarity	NPC119949
0.7358	Intermediate Similarity	NPC165797
0.7357	Intermediate Similarity	NPC249788
0.7355	Intermediate Similarity	NPC119669
0.7353	Intermediate Similarity	NPC280001
0.7353	Intermediate Similarity	NPC120075
0.7353	Intermediate Similarity	NPC185738
0.7353	Intermediate Similarity	NPC33271
0.7347	Intermediate Similarity	NPC307682
0.7346	Intermediate Similarity	NPC474324
0.7346	Intermediate Similarity	NPC57812
0.7343	Intermediate Similarity	NPC158471
0.7343	Intermediate Similarity	NPC57119
0.7343	Intermediate Similarity	NPC226862
0.7343	Intermediate Similarity	NPC165128
0.7338	Intermediate Similarity	NPC211296
0.7333	Intermediate Similarity	NPC181905
0.7333	Intermediate Similarity	NPC138438
0.7333	Intermediate Similarity	NPC908
0.7329	Intermediate Similarity	NPC306669
0.7329	Intermediate Similarity	NPC205915
0.7329	Intermediate Similarity	NPC168409
0.7325	Intermediate Similarity	NPC216459
0.7325	Intermediate Similarity	NPC41178
0.7325	Intermediate Similarity	NPC93593
0.7325	Intermediate Similarity	NPC138487
0.7317	Intermediate Similarity	NPC67978
0.7317	Intermediate Similarity	NPC303581
0.7315	Intermediate Similarity	NPC318575
0.7301	Intermediate Similarity	NPC475845
0.7296	Intermediate Similarity	NPC477080
0.7287	Intermediate Similarity	NPC292792
0.7279	Intermediate Similarity	NPC19890
0.7279	Intermediate Similarity	NPC110958
0.7278	Intermediate Similarity	NPC116007
0.7278	Intermediate Similarity	NPC146288
0.7273	Intermediate Similarity	NPC59907
0.7273	Intermediate Similarity	NPC37144
0.7267	Intermediate Similarity	NPC320104
0.7267	Intermediate Similarity	NPC218614
0.7266	Intermediate Similarity	NPC12714
0.7266	Intermediate Similarity	NPC471877
0.7266	Intermediate Similarity	NPC310905
0.7261	Intermediate Similarity	NPC292003
0.7256	Intermediate Similarity	NPC474708
0.7254	Intermediate Similarity	NPC17348
0.7246	Intermediate Similarity	NPC37858
0.7244	Intermediate Similarity	NPC476579
0.7241	Intermediate Similarity	NPC233224
0.7241	Intermediate Similarity	NPC271208
0.7241	Intermediate Similarity	NPC171550
0.7241	Intermediate Similarity	NPC134764
0.723	Intermediate Similarity	NPC231884
0.723	Intermediate Similarity	NPC42793
0.723	Intermediate Similarity	NPC167944
0.7222	Intermediate Similarity	NPC247972
0.7208	Intermediate Similarity	NPC95075
0.7208	Intermediate Similarity	NPC253883
0.7208	Intermediate Similarity	NPC90844
0.7203	Intermediate Similarity	NPC301713
0.7203	Intermediate Similarity	NPC274356
0.7202	Intermediate Similarity	NPC149285
0.72	Intermediate Similarity	NPC314682
0.7195	Intermediate Similarity	NPC158148
0.7195	Intermediate Similarity	NPC266176
0.7195	Intermediate Similarity	NPC475686
0.7195	Intermediate Similarity	NPC290759

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 NPC96406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	740
0.2-0.3	1129
0.3-0.4	2574
0.4-0.5	2636
0.5-0.6	1441
0.6-0.7	417
0.7-0.8	38
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9389	High Similarity	NPD2492	Phase 1
0.8207	Intermediate Similarity	NPD5297	Approved
0.8069	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4210	Discontinued
0.7589	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5718	Phase 2
0.747	Intermediate Similarity	NPD7281	Phase 3
0.747	Intermediate Similarity	NPD7280	Phase 3
0.7468	Intermediate Similarity	NPD824	Approved
0.7419	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1357	Approved
0.7353	Intermediate Similarity	NPD5536	Phase 2
0.7347	Intermediate Similarity	NPD743	Approved
0.7338	Intermediate Similarity	NPD3705	Approved
0.7338	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4237	Approved
0.7333	Intermediate Similarity	NPD4236	Phase 3
0.732	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3146	Approved
0.7319	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2653	Approved
0.7267	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1421	Approved
0.7234	Intermediate Similarity	NPD1420	Approved
0.723	Intermediate Similarity	NPD6895	Approved
0.723	Intermediate Similarity	NPD6896	Approved
0.7229	Intermediate Similarity	NPD3885	Approved
0.7181	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7110	Phase 1
0.7152	Intermediate Similarity	NPD6873	Phase 2
0.7152	Intermediate Similarity	NPD6385	Approved
0.7152	Intermediate Similarity	NPD6386	Approved
0.7125	Intermediate Similarity	NPD5977	Approved
0.7125	Intermediate Similarity	NPD5978	Approved
0.7124	Intermediate Similarity	NPD2219	Phase 1
0.7114	Intermediate Similarity	NPD6111	Discontinued
0.7089	Intermediate Similarity	NPD6875	Approved
0.7089	Intermediate Similarity	NPD6876	Approved
0.7075	Intermediate Similarity	NPD2674	Phase 3
0.7075	Intermediate Similarity	NPD2245	Discovery
0.7073	Intermediate Similarity	NPD4166	Phase 2
0.7063	Intermediate Similarity	NPD2978	Approved
0.7063	Intermediate Similarity	NPD2977	Approved
0.7059	Intermediate Similarity	NPD5283	Phase 1
0.7037	Intermediate Similarity	NPD5604	Discontinued
0.7032	Intermediate Similarity	NPD4357	Discontinued
0.7007	Intermediate Similarity	NPD3145	Approved
0.7007	Intermediate Similarity	NPD3144	Approved
0.7006	Intermediate Similarity	NPD1670	Discontinued
0.7	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1358	Approved
0.6974	Remote Similarity	NPD1375	Discontinued
0.695	Remote Similarity	NPD2667	Approved
0.695	Remote Similarity	NPD2668	Approved
0.6948	Remote Similarity	NPD5481	Discontinued
0.6933	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3134	Approved
0.6914	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3140	Approved
0.6913	Remote Similarity	NPD3142	Approved
0.6912	Remote Similarity	NPD228	Approved
0.6908	Remote Similarity	NPD2161	Phase 2
0.6903	Remote Similarity	NPD5241	Discontinued
0.6899	Remote Similarity	NPD3639	Approved
0.6899	Remote Similarity	NPD3640	Phase 3
0.6899	Remote Similarity	NPD3641	Approved
0.6897	Remote Similarity	NPD3349	Phase 2
0.6889	Remote Similarity	NPD5457	Discontinued
0.6883	Remote Similarity	NPD3060	Approved
0.6883	Remote Similarity	NPD4162	Approved
0.6879	Remote Similarity	NPD4584	Approved
0.6879	Remote Similarity	NPD4739	Approved
0.6859	Remote Similarity	NPD2120	Phase 2
0.6859	Remote Similarity	NPD7124	Phase 2
0.6854	Remote Similarity	NPD5582	Discontinued
0.6852	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7018	Phase 2
0.6828	Remote Similarity	NPD2922	Phase 1
0.6824	Remote Similarity	NPD5746	Approved
0.6818	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2233	Approved
0.6806	Remote Similarity	NPD2232	Approved
0.6806	Remote Similarity	NPD2230	Approved
0.6795	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5976	Discontinued
0.679	Remote Similarity	NPD7248	Discontinued
0.6786	Remote Similarity	NPD3596	Phase 2
0.6786	Remote Similarity	NPD2898	Approved
0.6779	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5177	Phase 3
0.6757	Remote Similarity	NPD4207	Discontinued
0.6753	Remote Similarity	NPD3656	Approved
0.675	Remote Similarity	NPD3687	Approved
0.675	Remote Similarity	NPD3686	Approved
0.6748	Remote Similarity	NPD5772	Approved
0.6748	Remote Similarity	NPD5773	Approved
0.6748	Remote Similarity	NPD4585	Approved
0.6735	Remote Similarity	NPD7905	Discontinued
0.6733	Remote Similarity	NPD3532	Approved
0.6733	Remote Similarity	NPD3530	Approved
0.6733	Remote Similarity	NPD3531	Approved
0.6733	Remote Similarity	NPD5745	Approved
0.6732	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5754	Discontinued
0.673	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6618	Phase 2
0.6724	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5163	Phase 2
0.671	Remote Similarity	NPD7153	Discontinued
0.671	Remote Similarity	NPD7037	Approved
0.6708	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4017	Approved
0.6707	Remote Similarity	NPD2560	Approved
0.6707	Remote Similarity	NPD5353	Approved
0.6707	Remote Similarity	NPD2563	Approved
0.6703	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1725	Approved
0.6687	Remote Similarity	NPD6031	Approved
0.6687	Remote Similarity	NPD6030	Approved
0.6686	Remote Similarity	NPD6297	Approved
0.6685	Remote Similarity	NPD7296	Approved
0.6685	Remote Similarity	NPD4420	Approved
0.6667	Remote Similarity	NPD5312	Approved
0.6667	Remote Similarity	NPD1424	Approved
0.6667	Remote Similarity	NPD2654	Approved
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD7119	Phase 2
0.6667	Remote Similarity	NPD5313	Approved
0.6667	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2594	Approved
0.6643	Remote Similarity	NPD6382	Discontinued
0.6643	Remote Similarity	NPD5691	Approved
0.6643	Remote Similarity	NPD2595	Approved
0.663	Remote Similarity	NPD5564	Approved
0.6627	Remote Similarity	NPD5242	Approved
0.6626	Remote Similarity	NPD5090	Approved
0.6626	Remote Similarity	NPD5089	Approved
0.6625	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6331	Phase 2
0.6623	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4108	Discontinued
0.6622	Remote Similarity	NPD6584	Phase 3
0.6621	Remote Similarity	NPD776	Approved
0.6611	Remote Similarity	NPD6493	Phase 3
0.661	Remote Similarity	NPD7291	Discontinued
0.661	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4626	Approved
0.6588	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4481	Phase 3
0.6585	Remote Similarity	NPD3383	Approved
0.6585	Remote Similarity	NPD3384	Approved
0.6585	Remote Similarity	NPD3382	Approved
0.6584	Remote Similarity	NPD4727	Phase 1
0.6584	Remote Similarity	NPD2122	Discontinued
0.6581	Remote Similarity	NPD6032	Approved
0.6579	Remote Similarity	NPD3109	Approved
0.6579	Remote Similarity	NPD3110	Approved
0.6577	Remote Similarity	NPD9494	Approved
0.6577	Remote Similarity	NPD2237	Approved
0.6573	Remote Similarity	NPD6580	Approved
0.6573	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6581	Approved
0.6573	Remote Similarity	NPD2486	Discontinued
0.6562	Remote Similarity	NPD4123	Phase 3
0.6562	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2335	Discontinued
0.6556	Remote Similarity	NPD1336	Approved
0.6556	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1039	Discontinued
0.6556	Remote Similarity	NPD5109	Approved
0.6556	Remote Similarity	NPD5110	Phase 2
0.6556	Remote Similarity	NPD5111	Phase 2
0.6554	Remote Similarity	NPD1817	Approved
0.6554	Remote Similarity	NPD1819	Approved
0.6554	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1820	Approved
0.6554	Remote Similarity	NPD1818	Approved
0.6552	Remote Similarity	NPD3294	Phase 2
0.6552	Remote Similarity	NPD3447	Discontinued
0.6548	Remote Similarity	NPD5677	Discontinued
0.6545	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4859	Phase 1
0.6543	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5295	Discontinued
0.6541	Remote Similarity	NPD5005	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data