NPASS Compound

Structure

NPC107476 OpenBabel07101718312D 24 26 0 0 1 0 0 0 0 0999 V2000 0.2646 -4.8935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3806 -3.6540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6193 2.0531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7263 -2.4447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0506 -2.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2508 -3.3072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0492 1.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8831 0.9049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1008 -1.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7662 -1.7210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0492 -1.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1496 -1.4234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4648 -3.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1008 1.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4818 -0.4815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2125 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4818 0.4815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5660 0.7791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8831 -0.9049 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5660 -0.7791 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0654 -1.1258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2684 1.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8314 -0.7377 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 5 6 1 0 0 0 0 5 10 2 0 0 0 0 6 13 2 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 1 0 0 0 16 19 1 1 0 0 0 16 23 1 0 0 0 0 17 14 1 6 0 0 0 17 18 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 4 1 1 0 0 0 19 23 1 0 0 0 0 20 10 1 6 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.15
Volume:	374.258
LogP:	-1.532
LogD:	-1.243
LogS:	-0.845
# Rotatable Bonds:	8
TPSA:	178.53
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	4.126
Fsp3:	0.647
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.077
MDCK Permeability:	9.668629354564473e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.937
Human Intestinal Absorption (HIA):	0.886
20% Bioavailability (F20%):	0.221
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.297
Plasma Protein Binding (PPB):	26.08499526977539%
Volume Distribution (VD):	0.397
Pgp-substrate:	50.106544494628906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.576
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.145
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	2.399
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.226
Human Hepatotoxicity (H-HT):	0.236
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.375
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC107476

Natural Product ID:	NPC107476
*Common Name:**	JYBJATPZXXGWRQ-JFJONPEWSA-N
IUPAC Name:	n.a.
Synonyms:	Xeniolide-H
Standard InCHIKey:	JYBJATPZXXGWRQ-JFJONPEWSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-13(2)6-5-10-20(12-21)15-9-11-19(4)16(23-19)8-7-14(3)17(15)18(22)24-20/h5-6,10,15-17,21H,3,7-9,11-12H2,1-2,4H3/b10-5+/t15-,16-,17-,19-,20-/m0/s1
SMILES:	CC(=C/C=C/[C@]1(CO)[C@H]2CC[C@@]3(C)[C@H](CCC(=C)[C@@H]2C(=O)O1)O3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463464
PubChem CID:	11002095
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[12502332]
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562830]
NPO14298	Xenia umbellata	Species	Xeniidae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	18.8	ug ml-1	PMID[521704]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	5.33	ug ml-1	PMID[521704]
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.66	ug ml-1	PMID[521704]

☑ 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 NPC107476 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	220
0.1-0.2	1107
0.2-0.3	4341
0.3-0.4	10274
0.4-0.5	14237
0.5-0.6	8112
0.6-0.7	3585
0.7-0.8	775
0.8-0.85	38
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8989	High Similarity	NPC474765
0.8947	High Similarity	NPC475053
0.8817	High Similarity	NPC474035
0.8817	High Similarity	NPC81386
0.8723	High Similarity	NPC14961
0.8723	High Similarity	NPC270013
0.8723	High Similarity	NPC272050
0.871	High Similarity	NPC212486
0.8602	High Similarity	NPC30515
0.8587	High Similarity	NPC473564
0.8511	High Similarity	NPC475912
0.8511	High Similarity	NPC81419
0.8511	High Similarity	NPC179746
0.8495	Intermediate Similarity	NPC476004
0.8495	Intermediate Similarity	NPC51004
0.8495	Intermediate Similarity	NPC474761
0.8478	Intermediate Similarity	NPC202672
0.8462	Intermediate Similarity	NPC116575
0.8444	Intermediate Similarity	NPC474776
0.8438	Intermediate Similarity	NPC476315
0.8404	Intermediate Similarity	NPC184463
0.8404	Intermediate Similarity	NPC208886
0.8404	Intermediate Similarity	NPC12172
0.8387	Intermediate Similarity	NPC307411
0.837	Intermediate Similarity	NPC231889
0.8333	Intermediate Similarity	NPC36954
0.8316	Intermediate Similarity	NPC476049
0.8316	Intermediate Similarity	NPC476300
0.828	Intermediate Similarity	NPC281516
0.8265	Intermediate Similarity	NPC473326
0.8247	Intermediate Similarity	NPC279621
0.8247	Intermediate Similarity	NPC473859
0.8229	Intermediate Similarity	NPC303942
0.8229	Intermediate Similarity	NPC57405
0.8218	Intermediate Similarity	NPC474741
0.8191	Intermediate Similarity	NPC212598
0.8191	Intermediate Similarity	NPC474032
0.8191	Intermediate Similarity	NPC115179
0.8191	Intermediate Similarity	NPC106040
0.8182	Intermediate Similarity	NPC288876
0.8152	Intermediate Similarity	NPC474369
0.8152	Intermediate Similarity	NPC21469
0.8144	Intermediate Similarity	NPC475659
0.8137	Intermediate Similarity	NPC243998
0.8132	Intermediate Similarity	NPC475842
0.8132	Intermediate Similarity	NPC250315
0.8125	Intermediate Similarity	NPC125674
0.8125	Intermediate Similarity	NPC475838
0.8125	Intermediate Similarity	NPC228451
0.8119	Intermediate Similarity	NPC475871
0.8119	Intermediate Similarity	NPC475945
0.8105	Intermediate Similarity	NPC475748
0.81	Intermediate Similarity	NPC473332
0.81	Intermediate Similarity	NPC476270
0.81	Intermediate Similarity	NPC474742
0.8085	Intermediate Similarity	NPC153805
0.8081	Intermediate Similarity	NPC187268
0.8081	Intermediate Similarity	NPC474213
0.8065	Intermediate Similarity	NPC164393
0.8065	Intermediate Similarity	NPC122502
0.8058	Intermediate Similarity	NPC474421
0.8058	Intermediate Similarity	NPC72813
0.8058	Intermediate Similarity	NPC326994
0.8058	Intermediate Similarity	NPC324327
0.8058	Intermediate Similarity	NPC194620
0.8041	Intermediate Similarity	NPC474247
0.802	Intermediate Similarity	NPC474747
0.802	Intermediate Similarity	NPC471148
0.8	Intermediate Similarity	NPC151770
0.8	Intermediate Similarity	NPC295312
0.7981	Intermediate Similarity	NPC169888
0.7981	Intermediate Similarity	NPC474664
0.7981	Intermediate Similarity	NPC327286
0.7981	Intermediate Similarity	NPC233379
0.7981	Intermediate Similarity	NPC14862
0.7981	Intermediate Similarity	NPC55972
0.7979	Intermediate Similarity	NPC186148
0.7979	Intermediate Similarity	NPC248602
0.7979	Intermediate Similarity	NPC475703
0.7979	Intermediate Similarity	NPC179659
0.7979	Intermediate Similarity	NPC160138
0.7961	Intermediate Similarity	NPC9303
0.7961	Intermediate Similarity	NPC223450
0.7961	Intermediate Similarity	NPC16313
0.7959	Intermediate Similarity	NPC471141
0.7959	Intermediate Similarity	NPC304886
0.7957	Intermediate Similarity	NPC304509
0.7957	Intermediate Similarity	NPC47958
0.7957	Intermediate Similarity	NPC149725
0.7957	Intermediate Similarity	NPC137033
0.7941	Intermediate Similarity	NPC4620
0.7935	Intermediate Similarity	NPC272814
0.7935	Intermediate Similarity	NPC231601
0.7935	Intermediate Similarity	NPC11620
0.7921	Intermediate Similarity	NPC474339
0.7921	Intermediate Similarity	NPC164598
0.7917	Intermediate Similarity	NPC62815
0.7917	Intermediate Similarity	NPC316228
0.7917	Intermediate Similarity	NPC475855
0.7917	Intermediate Similarity	NPC473619
0.7917	Intermediate Similarity	NPC313670
0.7917	Intermediate Similarity	NPC473448
0.7912	Intermediate Similarity	NPC474894
0.7905	Intermediate Similarity	NPC38154
0.7905	Intermediate Similarity	NPC15218
0.79	Intermediate Similarity	NPC222303
0.79	Intermediate Similarity	NPC161855
0.7895	Intermediate Similarity	NPC227379
0.7895	Intermediate Similarity	NPC474471
0.7895	Intermediate Similarity	NPC177629
0.7895	Intermediate Similarity	NPC58219
0.7885	Intermediate Similarity	NPC477513
0.7879	Intermediate Similarity	NPC230800
0.7879	Intermediate Similarity	NPC473291
0.7872	Intermediate Similarity	NPC50637
0.7872	Intermediate Similarity	NPC470242
0.7864	Intermediate Similarity	NPC475676
0.7864	Intermediate Similarity	NPC203659
0.7864	Intermediate Similarity	NPC220964
0.7857	Intermediate Similarity	NPC473316
0.7857	Intermediate Similarity	NPC473330
0.7849	Intermediate Similarity	NPC72464
0.7849	Intermediate Similarity	NPC474780
0.7843	Intermediate Similarity	NPC149371
0.7843	Intermediate Similarity	NPC86077
0.7835	Intermediate Similarity	NPC473321
0.7835	Intermediate Similarity	NPC475972
0.7835	Intermediate Similarity	NPC70251
0.7835	Intermediate Similarity	NPC475881
0.7826	Intermediate Similarity	NPC89555
0.7826	Intermediate Similarity	NPC475936
0.7822	Intermediate Similarity	NPC475949
0.7812	Intermediate Similarity	NPC166919
0.7812	Intermediate Similarity	NPC92974
0.7788	Intermediate Similarity	NPC475802
0.7788	Intermediate Similarity	NPC54737
0.7778	Intermediate Similarity	NPC469454
0.7778	Intermediate Similarity	NPC474947
0.7778	Intermediate Similarity	NPC469496
0.7778	Intermediate Similarity	NPC469463
0.7767	Intermediate Similarity	NPC474165
0.7767	Intermediate Similarity	NPC110989
0.7767	Intermediate Similarity	NPC69171
0.7767	Intermediate Similarity	NPC474775
0.7767	Intermediate Similarity	NPC475873
0.7766	Intermediate Similarity	NPC474547
0.7766	Intermediate Similarity	NPC215364
0.7766	Intermediate Similarity	NPC329749
0.7766	Intermediate Similarity	NPC38468
0.7766	Intermediate Similarity	NPC319795
0.7766	Intermediate Similarity	NPC50362
0.7757	Intermediate Similarity	NPC179798
0.7757	Intermediate Similarity	NPC304180
0.7755	Intermediate Similarity	NPC162205
0.7755	Intermediate Similarity	NPC273579
0.7755	Intermediate Similarity	NPC295204
0.7755	Intermediate Similarity	NPC288240
0.7745	Intermediate Similarity	NPC150923
0.7745	Intermediate Similarity	NPC201718
0.7745	Intermediate Similarity	NPC47880
0.7745	Intermediate Similarity	NPC472753
0.7742	Intermediate Similarity	NPC170377
0.7742	Intermediate Similarity	NPC53867
0.7736	Intermediate Similarity	NPC475922
0.7732	Intermediate Similarity	NPC144133
0.7732	Intermediate Similarity	NPC474323
0.7732	Intermediate Similarity	NPC206614
0.7732	Intermediate Similarity	NPC179394
0.7723	Intermediate Similarity	NPC471144
0.7717	Intermediate Similarity	NPC207188
0.7717	Intermediate Similarity	NPC141810
0.7708	Intermediate Similarity	NPC473715
0.7706	Intermediate Similarity	NPC73314
0.7692	Intermediate Similarity	NPC258532
0.7692	Intermediate Similarity	NPC477510
0.7692	Intermediate Similarity	NPC89128
0.7692	Intermediate Similarity	NPC471537
0.7692	Intermediate Similarity	NPC472756
0.7692	Intermediate Similarity	NPC471143
0.7692	Intermediate Similarity	NPC100487
0.7684	Intermediate Similarity	NPC61527
0.7684	Intermediate Similarity	NPC474949
0.7684	Intermediate Similarity	NPC284902
0.7684	Intermediate Similarity	NPC475019
0.7679	Intermediate Similarity	NPC475003
0.7677	Intermediate Similarity	NPC471147
0.7677	Intermediate Similarity	NPC71589
0.7677	Intermediate Similarity	NPC477131
0.7677	Intermediate Similarity	NPC474338
0.767	Intermediate Similarity	NPC183571
0.767	Intermediate Similarity	NPC472754
0.767	Intermediate Similarity	NPC225353
0.767	Intermediate Similarity	NPC303653
0.767	Intermediate Similarity	NPC189609
0.767	Intermediate Similarity	NPC140591
0.767	Intermediate Similarity	NPC235369
0.767	Intermediate Similarity	NPC197835
0.767	Intermediate Similarity	NPC291500
0.7667	Intermediate Similarity	NPC84360
0.7664	Intermediate Similarity	NPC115257

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 NPC107476 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1542
0.2-0.3	3687
0.3-0.4	2508
0.4-0.5	829
0.5-0.6	327
0.6-0.7	65
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
0.7917	Intermediate Similarity	NPD46	Approved
0.7917	Intermediate Similarity	NPD6698	Approved
0.7917	Intermediate Similarity	NPD7838	Discovery
0.7835	Intermediate Similarity	NPD7983	Approved
0.7766	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5779	Approved
0.74	Intermediate Similarity	NPD5778	Approved
0.7383	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6371	Approved
0.7273	Intermediate Similarity	NPD1695	Approved
0.7273	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD8517	Approved
0.7155	Intermediate Similarity	NPD8515	Approved
0.7155	Intermediate Similarity	NPD8513	Phase 3
0.7155	Intermediate Similarity	NPD8516	Approved
0.7087	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5344	Discontinued
0.701	Intermediate Similarity	NPD5362	Discontinued
0.701	Intermediate Similarity	NPD7154	Phase 3
0.6981	Remote Similarity	NPD6648	Approved
0.6979	Remote Similarity	NPD5369	Approved
0.697	Remote Similarity	NPD4249	Approved
0.697	Remote Similarity	NPD5786	Approved
0.6931	Remote Similarity	NPD6101	Approved
0.6931	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4269	Approved
0.6907	Remote Similarity	NPD4270	Approved
0.69	Remote Similarity	NPD4251	Approved
0.69	Remote Similarity	NPD4250	Approved
0.6887	Remote Similarity	NPD4225	Approved
0.6863	Remote Similarity	NPD5785	Approved
0.686	Remote Similarity	NPD8074	Phase 3
0.6857	Remote Similarity	NPD7839	Suspended
0.6847	Remote Similarity	NPD6686	Approved
0.681	Remote Similarity	NPD7115	Discovery
0.6796	Remote Similarity	NPD6411	Approved
0.6786	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6435	Approved
0.6701	Remote Similarity	NPD4820	Approved
0.6701	Remote Similarity	NPD4819	Approved
0.6701	Remote Similarity	NPD4821	Approved
0.6701	Remote Similarity	NPD4252	Approved
0.6701	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4822	Approved
0.67	Remote Similarity	NPD5363	Approved
0.67	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8273	Phase 1
0.6635	Remote Similarity	NPD7637	Suspended
0.6609	Remote Similarity	NPD6053	Discontinued
0.6579	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7638	Approved
0.6566	Remote Similarity	NPD5209	Approved
0.6535	Remote Similarity	NPD1694	Approved
0.6531	Remote Similarity	NPD5368	Approved
0.6526	Remote Similarity	NPD8039	Approved
0.6514	Remote Similarity	NPD7639	Approved
0.6514	Remote Similarity	NPD7640	Approved
0.6504	Remote Similarity	NPD8451	Approved
0.65	Remote Similarity	NPD5331	Approved
0.65	Remote Similarity	NPD5332	Approved
0.6495	Remote Similarity	NPD4271	Approved
0.6495	Remote Similarity	NPD4268	Approved
0.6484	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7830	Approved
0.6475	Remote Similarity	NPD7829	Approved
0.6465	Remote Similarity	NPD4790	Discontinued
0.6452	Remote Similarity	NPD8448	Approved
0.6444	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7524	Approved
0.6404	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6008	Approved
0.6341	Remote Similarity	NPD7642	Approved
0.6337	Remote Similarity	NPD6110	Phase 1
0.6316	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8444	Approved
0.6299	Remote Similarity	NPD8392	Approved
0.6299	Remote Similarity	NPD8390	Approved
0.6299	Remote Similarity	NPD8391	Approved
0.629	Remote Similarity	NPD8341	Approved
0.629	Remote Similarity	NPD8340	Approved
0.629	Remote Similarity	NPD8299	Approved
0.629	Remote Similarity	NPD8342	Approved
0.6271	Remote Similarity	NPD4632	Approved
0.6262	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD7260	Phase 2
0.624	Remote Similarity	NPD7507	Approved
0.6198	Remote Similarity	NPD7641	Discontinued
0.6176	Remote Similarity	NPD6695	Phase 3
0.6154	Remote Similarity	NPD3197	Phase 1
0.6132	Remote Similarity	NPD5370	Suspended
0.6117	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD2204	Approved
0.6098	Remote Similarity	NPD6319	Approved
0.6094	Remote Similarity	NPD7319	Approved
0.6091	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7503	Approved
0.6034	Remote Similarity	NPD6412	Phase 2
0.6019	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5284	Approved
0.6019	Remote Similarity	NPD5281	Approved
0.6	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6009	Approved
0.5966	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD7632	Discontinued
0.596	Remote Similarity	NPD6933	Approved
0.5954	Remote Similarity	NPD6845	Suspended
0.5952	Remote Similarity	NPD7604	Phase 2
0.5943	Remote Similarity	NPD7750	Discontinued
0.5926	Remote Similarity	NPD5207	Approved
0.5922	Remote Similarity	NPD3667	Approved
0.5922	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.592	Remote Similarity	NPD5983	Phase 2
0.5917	Remote Similarity	NPD8297	Approved
0.5906	Remote Similarity	NPD7492	Approved
0.5902	Remote Similarity	NPD2629	Approved
0.59	Remote Similarity	NPD4756	Discovery
0.5897	Remote Similarity	NPD5697	Approved
0.5897	Remote Similarity	NPD6685	Approved
0.5893	Remote Similarity	NPD6083	Phase 2
0.5893	Remote Similarity	NPD6084	Phase 2
0.5882	Remote Similarity	NPD7332	Phase 2
0.5882	Remote Similarity	NPD2067	Discontinued
0.5882	Remote Similarity	NPD6931	Approved
0.5882	Remote Similarity	NPD7514	Phase 3
0.5882	Remote Similarity	NPD6421	Discontinued
0.5882	Remote Similarity	NPD6930	Phase 2
0.5859	Remote Similarity	NPD6616	Approved
0.5856	Remote Similarity	NPD5695	Phase 3
0.5854	Remote Similarity	NPD7500	Approved
0.5849	Remote Similarity	NPD6422	Discontinued
0.5849	Remote Similarity	NPD5279	Phase 3
0.5847	Remote Similarity	NPD6899	Approved
0.5847	Remote Similarity	NPD6881	Approved
0.5847	Remote Similarity	NPD6011	Approved
0.5841	Remote Similarity	NPD5696	Approved
0.584	Remote Similarity	NPD6054	Approved
0.5833	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD6649	Approved
0.5825	Remote Similarity	NPD6902	Approved
0.5814	Remote Similarity	NPD7078	Approved
0.5812	Remote Similarity	NPD5048	Discontinued
0.5812	Remote Similarity	NPD6675	Approved
0.5812	Remote Similarity	NPD7128	Approved
0.5812	Remote Similarity	NPD5739	Approved
0.5812	Remote Similarity	NPD6402	Approved
0.581	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4786	Approved
0.5806	Remote Similarity	NPD7327	Approved
0.5806	Remote Similarity	NPD7909	Approved
0.5806	Remote Similarity	NPD7328	Approved
0.5798	Remote Similarity	NPD6012	Approved
0.5798	Remote Similarity	NPD6013	Approved
0.5798	Remote Similarity	NPD6014	Approved
0.5798	Remote Similarity	NPD6373	Approved
0.5798	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6372	Approved
0.5794	Remote Similarity	NPD6921	Approved
0.5794	Remote Similarity	NPD6015	Approved
0.5794	Remote Similarity	NPD6016	Approved
0.5794	Remote Similarity	NPD8033	Approved
0.5784	Remote Similarity	NPD6929	Approved
0.578	Remote Similarity	NPD3168	Discontinued
0.5776	Remote Similarity	NPD6647	Phase 2
0.5769	Remote Similarity	NPD7736	Approved
0.5766	Remote Similarity	NPD7748	Approved
0.5763	Remote Similarity	NPD5701	Approved
0.576	Remote Similarity	NPD7516	Approved
0.5758	Remote Similarity	NPD6924	Approved
0.5758	Remote Similarity	NPD6926	Approved
0.5755	Remote Similarity	NPD1696	Phase 3
0.5752	Remote Similarity	NPD7902	Approved
0.575	Remote Similarity	NPD6883	Approved
0.575	Remote Similarity	NPD7102	Approved
0.575	Remote Similarity	NPD7290	Approved
0.5748	Remote Similarity	NPD6370	Approved
0.5748	Remote Similarity	NPD5988	Approved
0.5743	Remote Similarity	NPD6932	Approved
0.5736	Remote Similarity	NPD6336	Discontinued
0.5727	Remote Similarity	NPD7515	Phase 2
0.5727	Remote Similarity	NPD5693	Phase 1
0.5727	Remote Similarity	NPD5694	Approved
0.5727	Remote Similarity	NPD7087	Discontinued
0.5726	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD6059	Approved
0.5714	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD8377	Approved
0.5714	Remote Similarity	NPD8294	Approved
0.5714	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD8328	Phase 3
0.5702	Remote Similarity	NPD1719	Phase 1
0.5702	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6847	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