NPASS Compound

Structure

NPC472519 OpenBabel07101719152D 21 22 0 0 0 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 10 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 5 1 0 0 0 0 4 10 2 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 17 2 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	293.675
LogP:	1.816
LogD:	1.858
LogS:	-3.371
# Rotatable Bonds:	5
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	2.755
Fsp3:	0.25
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:	-4.675
MDCK Permeability:	1.4514538634102792e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	86.75215911865234%
Volume Distribution (VD):	0.838
Pgp-substrate:	11.868568420410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.792
CYP2C19-substrate:	0.526
CYP2C9-inhibitor:	0.222
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.478
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.299
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	9.933
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.611
Drug-inuced Liver Injury (DILI):	0.191
AMES Toxicity:	0.309
Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.282
Skin Sensitization:	0.33
Carcinogencity:	0.869
Eye Corrosion:	0.012
Eye Irritation:	0.096
Respiratory Toxicity:	0.895

Download Data

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

Natural Product: NPC472519

Natural Product ID:	NPC472519
*Common Name:**	WZYSRODKTAPDMH-ONNFQVAWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WZYSRODKTAPDMH-ONNFQVAWSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-10(9-17)4-5-11-13(19-2)8-14(20-3)12-6-7-15(18)21-16(11)12/h4,6-9H,5H2,1-3H3/b10-4+
SMILES:	CC(=CCC1=C(C=C(C2=C1OC(=O)C=C2)OC)OC)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426672
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins 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
NPO33003	murraya alata	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25621853]

☑ 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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	28300.0	nM	PMID[544169]

☑ 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 NPC472519 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	404
0.1-0.2	1859
0.2-0.3	5109
0.3-0.4	11078
0.4-0.5	6710
0.5-0.6	4682
0.6-0.7	5958
0.7-0.8	4801
0.8-0.85	1295
0.85-0.9	630
0.9-0.95	150
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC201667
0.9669	High Similarity	NPC73413
0.9587	High Similarity	NPC109675
0.9587	High Similarity	NPC472518
0.9587	High Similarity	NPC273772
0.9508	High Similarity	NPC27671
0.9504	High Similarity	NPC96286
0.9504	High Similarity	NPC248429
0.9431	High Similarity	NPC471828
0.9431	High Similarity	NPC471827
0.937	High Similarity	NPC175159
0.9339	High Similarity	NPC163200
0.9339	High Similarity	NPC180006
0.9339	High Similarity	NPC235190
0.9302	High Similarity	NPC229128
0.9297	High Similarity	NPC7526
0.9297	High Similarity	NPC222036
0.9291	High Similarity	NPC472517
0.9286	High Similarity	NPC168710
0.9262	High Similarity	NPC144418
0.9225	High Similarity	NPC47163
0.9225	High Similarity	NPC18804
0.9225	High Similarity	NPC84894
0.9225	High Similarity	NPC287182
0.9225	High Similarity	NPC166672
0.9225	High Similarity	NPC267412
0.9225	High Similarity	NPC260265
0.9225	High Similarity	NPC74655
0.9225	High Similarity	NPC55149
0.9225	High Similarity	NPC307412
0.9225	High Similarity	NPC198381
0.9225	High Similarity	NPC195343
0.9225	High Similarity	NPC164269
0.9225	High Similarity	NPC127888
0.9225	High Similarity	NPC319859
0.9225	High Similarity	NPC100986
0.9219	High Similarity	NPC14248
0.9213	High Similarity	NPC80170
0.9206	High Similarity	NPC185066
0.9206	High Similarity	NPC199204
0.92	High Similarity	NPC471826
0.92	High Similarity	NPC234109
0.92	High Similarity	NPC188327
0.9194	High Similarity	NPC291899
0.9174	High Similarity	NPC298796
0.9174	High Similarity	NPC281356
0.9154	High Similarity	NPC472424
0.9154	High Similarity	NPC86892
0.9154	High Similarity	NPC471625
0.9154	High Similarity	NPC471909
0.9154	High Similarity	NPC281241
0.9147	High Similarity	NPC207002
0.9147	High Similarity	NPC167111
0.9147	High Similarity	NPC133956
0.9147	High Similarity	NPC296624
0.9147	High Similarity	NPC318400
0.9147	High Similarity	NPC471910
0.9147	High Similarity	NPC31849
0.9127	High Similarity	NPC243688
0.9113	High Similarity	NPC173350
0.9113	High Similarity	NPC154176
0.9113	High Similarity	NPC315807
0.9113	High Similarity	NPC290605
0.9113	High Similarity	NPC50720
0.9091	High Similarity	NPC96705
0.9091	High Similarity	NPC152306
0.9091	High Similarity	NPC265547
0.9084	High Similarity	NPC283019
0.9084	High Similarity	NPC160727
0.9084	High Similarity	NPC177281
0.9084	High Similarity	NPC149320
0.9084	High Similarity	NPC283331
0.9084	High Similarity	NPC471630
0.9084	High Similarity	NPC55615
0.9084	High Similarity	NPC128529
0.9084	High Similarity	NPC476455
0.9055	High Similarity	NPC157212
0.904	High Similarity	NPC111347
0.9032	High Similarity	NPC257188
0.9032	High Similarity	NPC13007
0.9032	High Similarity	NPC150214
0.9015	High Similarity	NPC155963
0.9008	High Similarity	NPC469675
0.9	High Similarity	NPC55147
0.9	High Similarity	NPC54503
0.8976	High Similarity	NPC121740
0.8976	High Similarity	NPC258567
0.8976	High Similarity	NPC224774
0.8968	High Similarity	NPC244495
0.8968	High Similarity	NPC93219
0.8947	High Similarity	NPC151946
0.8947	High Similarity	NPC211110
0.8939	High Similarity	NPC26954
0.8939	High Similarity	NPC38099
0.8931	High Similarity	NPC50896
0.8931	High Similarity	NPC224475
0.8931	High Similarity	NPC213173
0.8931	High Similarity	NPC180716
0.8931	High Similarity	NPC326600
0.8931	High Similarity	NPC62366
0.8931	High Similarity	NPC204353
0.8926	High Similarity	NPC128633
0.8923	High Similarity	NPC194277
0.8923	High Similarity	NPC19157
0.8923	High Similarity	NPC469956
0.8915	High Similarity	NPC32463
0.8915	High Similarity	NPC113098
0.8906	High Similarity	NPC60704
0.8906	High Similarity	NPC293642
0.8906	High Similarity	NPC139595
0.8906	High Similarity	NPC469453
0.8898	High Similarity	NPC101894
0.8881	High Similarity	NPC312881
0.8864	High Similarity	NPC472525
0.8864	High Similarity	NPC61499
0.8855	High Similarity	NPC469952
0.8855	High Similarity	NPC469955
0.8855	High Similarity	NPC163557
0.8846	High Similarity	NPC272650
0.8846	High Similarity	NPC29734
0.8846	High Similarity	NPC267336
0.8828	High Similarity	NPC289316
0.8819	High Similarity	NPC202594
0.8819	High Similarity	NPC232692
0.8815	High Similarity	NPC287286
0.8815	High Similarity	NPC152771
0.8815	High Similarity	NPC195357
0.8815	High Similarity	NPC472523
0.881	High Similarity	NPC143725
0.8806	High Similarity	NPC307883
0.8806	High Similarity	NPC279573
0.8806	High Similarity	NPC253616
0.8788	High Similarity	NPC98179
0.8788	High Similarity	NPC253574
0.8769	High Similarity	NPC19242
0.875	High Similarity	NPC163248
0.8731	High Similarity	NPC471068
0.8731	High Similarity	NPC268081
0.8731	High Similarity	NPC306365
0.8731	High Similarity	NPC14697
0.8731	High Similarity	NPC471069
0.8731	High Similarity	NPC232246
0.8731	High Similarity	NPC153818
0.8722	High Similarity	NPC33986
0.8712	High Similarity	NPC469449
0.8712	High Similarity	NPC2363
0.8692	High Similarity	NPC474289
0.8686	High Similarity	NPC119640
0.8686	High Similarity	NPC183646
0.8676	High Similarity	NPC155552
0.8676	High Similarity	NPC183642
0.8676	High Similarity	NPC310370
0.8667	High Similarity	NPC471070
0.8667	High Similarity	NPC471071
0.8667	High Similarity	NPC471072
0.8657	High Similarity	NPC224543
0.8657	High Similarity	NPC78746
0.8657	High Similarity	NPC188380
0.8651	High Similarity	NPC52247
0.8651	High Similarity	NPC187868
0.8647	High Similarity	NPC131950
0.8623	High Similarity	NPC476457
0.8603	High Similarity	NPC71903
0.8603	High Similarity	NPC36414
0.8593	High Similarity	NPC281014
0.8593	High Similarity	NPC184861
0.8593	High Similarity	NPC225106
0.8593	High Similarity	NPC131198
0.8593	High Similarity	NPC294456
0.8593	High Similarity	NPC212124
0.8593	High Similarity	NPC472516
0.8571	High Similarity	NPC472522
0.8571	High Similarity	NPC302107
0.8571	High Similarity	NPC291551
0.8571	High Similarity	NPC205797
0.8571	High Similarity	NPC472524
0.8571	High Similarity	NPC241341
0.8571	High Similarity	NPC233018
0.8571	High Similarity	NPC319378
0.8571	High Similarity	NPC141822
0.8571	High Similarity	NPC241165
0.8571	High Similarity	NPC36437
0.8571	High Similarity	NPC1220
0.8571	High Similarity	NPC142563
0.8551	High Similarity	NPC229916
0.854	High Similarity	NPC138149
0.854	High Similarity	NPC170812
0.854	High Similarity	NPC472515
0.8529	High Similarity	NPC278600
0.8529	High Similarity	NPC270256
0.8529	High Similarity	NPC144512
0.8529	High Similarity	NPC37428
0.8529	High Similarity	NPC137262
0.8529	High Similarity	NPC35501
0.8529	High Similarity	NPC47040
0.8527	High Similarity	NPC168259
0.8525	High Similarity	NPC90903
0.8519	High Similarity	NPC104796
0.8507	High Similarity	NPC184677
0.85	High Similarity	NPC208584

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 NPC472519 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	998
0.2-0.3	1750
0.3-0.4	2690
0.4-0.5	1808
0.5-0.6	1049
0.6-0.7	339
0.7-0.8	93
0.8-0.85	34
0.85-0.9	14
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8651	High Similarity	NPD422	Phase 1
0.8571	High Similarity	NPD5123	Clinical (unspecified phase)
0.8571	High Similarity	NPD5124	Phase 1
0.8473	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1296	Phase 2
0.8346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD920	Approved
0.8227	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD3748	Approved
0.8112	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD2796	Approved
0.8017	Intermediate Similarity	NPD9697	Approved
0.8014	Intermediate Similarity	NPD1652	Phase 2
0.8014	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD5535	Approved
0.7984	Intermediate Similarity	NPD5691	Approved
0.7951	Intermediate Similarity	NPD3134	Approved
0.7941	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD6832	Phase 2
0.7917	Intermediate Similarity	NPD6799	Approved
0.7907	Intermediate Similarity	NPD1548	Phase 1
0.7905	Intermediate Similarity	NPD7411	Suspended
0.7887	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD1358	Approved
0.7852	Intermediate Similarity	NPD6801	Discontinued
0.7836	Intermediate Similarity	NPD2797	Approved
0.7836	Intermediate Similarity	NPD3267	Approved
0.7836	Intermediate Similarity	NPD3266	Approved
0.7832	Intermediate Similarity	NPD3750	Approved
0.7829	Intermediate Similarity	NPD919	Approved
0.7801	Intermediate Similarity	NPD1551	Phase 2
0.78	Intermediate Similarity	NPD7819	Suspended
0.78	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD4908	Phase 1
0.7761	Intermediate Similarity	NPD3225	Approved
0.774	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6599	Discontinued
0.7708	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7768	Phase 2
0.7681	Intermediate Similarity	NPD3268	Approved
0.7669	Intermediate Similarity	NPD1610	Phase 2
0.7656	Intermediate Similarity	NPD1241	Discontinued
0.7652	Intermediate Similarity	NPD4626	Approved
0.7651	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7075	Discontinued
0.7619	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD3496	Discontinued
0.7571	Intermediate Similarity	NPD4307	Phase 2
0.7569	Intermediate Similarity	NPD1549	Phase 2
0.755	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1019	Discontinued
0.7517	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5401	Approved
0.7483	Intermediate Similarity	NPD7033	Discontinued
0.7483	Intermediate Similarity	NPD1510	Phase 2
0.7483	Intermediate Similarity	NPD2799	Discontinued
0.7481	Intermediate Similarity	NPD9717	Approved
0.7467	Intermediate Similarity	NPD1653	Approved
0.7466	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1240	Approved
0.7447	Intermediate Similarity	NPD4060	Phase 1
0.7431	Intermediate Similarity	NPD2935	Discontinued
0.7429	Intermediate Similarity	NPD6798	Discontinued
0.7407	Intermediate Similarity	NPD1611	Approved
0.7403	Intermediate Similarity	NPD3817	Phase 2
0.7402	Intermediate Similarity	NPD2684	Approved
0.7394	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4340	Discontinued
0.7388	Intermediate Similarity	NPD1778	Approved
0.7372	Intermediate Similarity	NPD8651	Approved
0.7368	Intermediate Similarity	NPD4380	Phase 2
0.7365	Intermediate Similarity	NPD6667	Approved
0.7365	Intermediate Similarity	NPD6666	Approved
0.7361	Intermediate Similarity	NPD4308	Phase 3
0.7358	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD4625	Phase 3
0.7347	Intermediate Similarity	NPD4628	Phase 3
0.7343	Intermediate Similarity	NPD1607	Approved
0.7338	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5844	Phase 1
0.7329	Intermediate Similarity	NPD2424	Discontinued
0.7319	Intermediate Similarity	NPD1203	Approved
0.7308	Intermediate Similarity	NPD7843	Approved
0.7305	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2313	Discontinued
0.7299	Intermediate Similarity	NPD4749	Approved
0.729	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1247	Approved
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.726	Intermediate Similarity	NPD6002	Phase 3
0.726	Intermediate Similarity	NPD6004	Phase 3
0.726	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6005	Phase 3
0.726	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD17	Approved
0.7244	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1894	Discontinued
0.7215	Intermediate Similarity	NPD5494	Approved
0.7206	Intermediate Similarity	NPD3847	Discontinued
0.7203	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1613	Approved
0.72	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6559	Discontinued
0.7192	Intermediate Similarity	NPD4476	Approved
0.7192	Intermediate Similarity	NPD4477	Approved
0.7185	Intermediate Similarity	NPD5585	Approved
0.7179	Intermediate Similarity	NPD4288	Approved
0.7179	Intermediate Similarity	NPD5402	Approved
0.7172	Intermediate Similarity	NPD7097	Phase 1
0.7171	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1933	Approved
0.7153	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1091	Approved
0.7143	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5953	Discontinued
0.7133	Intermediate Similarity	NPD6233	Phase 2
0.7125	Intermediate Similarity	NPD7229	Phase 3
0.7117	Intermediate Similarity	NPD7286	Phase 2
0.7113	Intermediate Similarity	NPD3027	Phase 3
0.7111	Intermediate Similarity	NPD9545	Approved
0.7105	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1608	Approved
0.7092	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3018	Phase 2
0.7089	Intermediate Similarity	NPD3749	Approved
0.7086	Intermediate Similarity	NPD7212	Phase 2
0.7086	Intermediate Similarity	NPD7213	Phase 3
0.7083	Intermediate Similarity	NPD2979	Phase 3
0.7083	Intermediate Similarity	NPD4140	Approved
0.7063	Intermediate Similarity	NPD940	Approved
0.7063	Intermediate Similarity	NPD846	Approved
0.7055	Intermediate Similarity	NPD2200	Suspended
0.7054	Intermediate Similarity	NPD290	Approved
0.7051	Intermediate Similarity	NPD1934	Approved
0.7047	Intermediate Similarity	NPD2800	Approved
0.7039	Intermediate Similarity	NPD7447	Phase 1
0.7037	Intermediate Similarity	NPD5536	Phase 2
0.7029	Intermediate Similarity	NPD1281	Approved
0.7027	Intermediate Similarity	NPD5763	Approved
0.7027	Intermediate Similarity	NPD5762	Approved
0.7025	Intermediate Similarity	NPD3882	Suspended
0.7021	Intermediate Similarity	NPD3691	Phase 2
0.7021	Intermediate Similarity	NPD3690	Phase 2
0.702	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2557	Approved
0.7014	Intermediate Similarity	NPD8032	Phase 2
0.7014	Intermediate Similarity	NPD4062	Phase 3
0.7012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2801	Approved
0.7	Intermediate Similarity	NPD7466	Approved
0.6993	Remote Similarity	NPD7095	Approved
0.6993	Remote Similarity	NPD5163	Phase 2
0.6987	Remote Similarity	NPD5890	Approved
0.6987	Remote Similarity	NPD5889	Approved
0.6986	Remote Similarity	NPD6651	Approved
0.6981	Remote Similarity	NPD6971	Discontinued
0.6978	Remote Similarity	NPD3972	Approved
0.6978	Remote Similarity	NPD2981	Phase 2
0.6974	Remote Similarity	NPD1511	Approved
0.6972	Remote Similarity	NPD2237	Approved
0.6972	Remote Similarity	NPD2861	Phase 2
0.697	Remote Similarity	NPD1137	Approved
0.697	Remote Similarity	NPD1139	Approved
0.6968	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3226	Approved
0.6966	Remote Similarity	NPD2203	Discontinued
0.6963	Remote Similarity	NPD3596	Phase 2
0.6959	Remote Similarity	NPD6100	Approved
0.6959	Remote Similarity	NPD6099	Approved
0.6959	Remote Similarity	NPD2438	Suspended
0.6957	Remote Similarity	NPD7199	Phase 2
0.6954	Remote Similarity	NPD3887	Approved
0.6947	Remote Similarity	NPD5451	Approved
0.6946	Remote Similarity	NPD7549	Discontinued
0.6944	Remote Similarity	NPD411	Approved
0.6944	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1651	Approved
0.6933	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2654	Approved
0.6933	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4359	Approved
0.6929	Remote Similarity	NPD2982	Phase 2
0.6929	Remote Similarity	NPD2983	Phase 2
0.6928	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2614	Approved
0.6918	Remote Similarity	NPD4622	Approved
0.6918	Remote Similarity	NPD230	Phase 1
0.6918	Remote Similarity	NPD447	Suspended
0.6918	Remote Similarity	NPD4618	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