NPASS Compound

Structure

NPC311070 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 -2.8147 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2788 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9487 1.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4128 1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9487 2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 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 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 20 1 6 0 0 0 16 21 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 6 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	4.446
LogD:	3.93
LogS:	-4.103
# Rotatable Bonds:	3
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.752
Synthetic Accessibility Score:	4.491
Fsp3:	0.7
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:	-4.644
MDCK Permeability:	1.8296548660146073e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.426
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.91
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.369
Plasma Protein Binding (PPB):	88.6781234741211%
Volume Distribution (VD):	1.325
Pgp-substrate:	12.9597749710083%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.28
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.363
CYP2C9-inhibitor:	0.41
CYP2C9-substrate:	0.701
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.781
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	13.172
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.865
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.475
Carcinogencity:	0.797
Eye Corrosion:	0.012
Eye Irritation:	0.176
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC311070

Natural Product ID:	NPC311070
*Common Name:**	YIFIMTKQFWTJEA-PFRQMTDMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YIFIMTKQFWTJEA-PFRQMTDMSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13-6-7-17-19(2,3)8-5-9-20(17,4)15(13)11-16(21)14-10-18(22)23-12-14/h10,15-17,21H,1,5-9,11-12H2,2-4H3/t15-,16+,17-,20+/m0/s1
SMILES:	O=C1OCC(=C1)[C@@H](C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586268
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO32474	vitex vestita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26034885]

☑ 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
MIC	46
Others	4

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3
Organism	43

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	GI	=	86.0	%	PMID[484960]
NPT171	Cell Line	MRC5	Homo sapiens	GI	=	34.0	%	PMID[484960]
NPT393	Cell Line	HCT-116	Homo sapiens	GI	=	68.0	%	PMID[484960]
NPT393	Cell Line	HCT-116	Homo sapiens	GI	=	3.0	%	PMID[484960]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	<=	188000.0	nM	PMID[484960]
NPT3145	Organism	Bacillus subtilis subsp. spizizenii ATCC 6633	Bacillus subtilis subsp. spizizenii ATCC 6633	MIC	>	188000.0	nM	PMID[484960]
NPT4843	Organism	Corynebacterium striatum	Corynebacterium striatum	MIC	>	188000.0	nM	PMID[484960]
NPT4075	Organism	Enterococcus avium	Enterococcus avium	MIC	>	188000.0	nM	PMID[484960]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	188000.0	nM	PMID[484960]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	=	50000.0	nM	PMID[484960]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	50000.0	nM	PMID[484960]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	188000.0	nM	PMID[484960]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	<=	188000.0	nM	PMID[484960]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	50000.0	nM	PMID[484960]
NPT4844	Organism	Enterococcus gallinarum	Enterococcus gallinarum	MIC	>	188000.0	nM	PMID[484960]
NPT3721	Organism	Enterococcus hirae	Enterococcus hirae	MIC	>	188000.0	nM	PMID[484960]
NPT4845	Organism	Listeria innocua	Listeria innocua	MIC	>	188000.0	nM	PMID[484960]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	>	188000.0	nM	PMID[484960]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	188000.0	nM	PMID[484960]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	188000.0	nM	PMID[484960]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	188000.0	nM	PMID[484960]
NPT4839	Organism	Staphylococcus intermedius	Staphylococcus intermedius	MIC	>	188000.0	nM	PMID[484960]
NPT4840	Organism	Staphylococcus lugdunensis	Staphylococcus lugdunensis	MIC	>	188000.0	nM	PMID[484960]
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	>	188000.0	nM	PMID[484960]
NPT4428	Organism	Staphylococcus sciuri	Staphylococcus sciuri	MIC	>	188000.0	nM	PMID[484960]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	50000.0	nM	PMID[484960]

☑ 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 NPC311070 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	159
0.1-0.2	1055
0.2-0.3	4208
0.3-0.4	11871
0.4-0.5	11226
0.5-0.6	6874
0.6-0.7	5679
0.7-0.8	1407
0.8-0.85	145
0.85-0.9	60
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.939	High Similarity	NPC472810
0.939	High Similarity	NPC472809
0.9383	High Similarity	NPC131813
0.925	High Similarity	NPC42476
0.9167	High Similarity	NPC78973
0.9059	High Similarity	NPC177037
0.9059	High Similarity	NPC472814
0.9048	High Similarity	NPC470734
0.9012	High Similarity	NPC472377
0.8953	High Similarity	NPC472812
0.8941	High Similarity	NPC182136
0.8851	High Similarity	NPC469697
0.8837	High Similarity	NPC472811
0.8824	High Similarity	NPC50488
0.8824	High Similarity	NPC474396
0.8795	High Similarity	NPC86316
0.8795	High Similarity	NPC106416
0.8795	High Similarity	NPC471795
0.8795	High Similarity	NPC473251
0.8795	High Similarity	NPC42586
0.875	High Similarity	NPC242767
0.8736	High Similarity	NPC205034
0.8736	High Similarity	NPC115021
0.8736	High Similarity	NPC139692
0.8736	High Similarity	NPC152778
0.8736	High Similarity	NPC162615
0.8736	High Similarity	NPC53555
0.8721	High Similarity	NPC310479
0.8721	High Similarity	NPC221111
0.8721	High Similarity	NPC280149
0.8706	High Similarity	NPC474629
0.8706	High Similarity	NPC472378
0.869	High Similarity	NPC329692
0.8652	High Similarity	NPC134072
0.8652	High Similarity	NPC242848
0.8652	High Similarity	NPC234993
0.8652	High Similarity	NPC162346
0.8642	High Similarity	NPC281880
0.8636	High Similarity	NPC298973
0.8636	High Similarity	NPC470255
0.8636	High Similarity	NPC104925
0.8621	High Similarity	NPC72845
0.8621	High Similarity	NPC329842
0.8605	High Similarity	NPC174342
0.8588	High Similarity	NPC312561
0.8588	High Similarity	NPC471796
0.8588	High Similarity	NPC166857
0.8571	High Similarity	NPC30984
0.8571	High Similarity	NPC65661
0.8556	High Similarity	NPC477718
0.8556	High Similarity	NPC477719
0.8556	High Similarity	NPC475709
0.8554	High Similarity	NPC79945
0.8554	High Similarity	NPC474809
0.8539	High Similarity	NPC472441
0.8539	High Similarity	NPC276110
0.8537	High Similarity	NPC170303
0.8537	High Similarity	NPC159148
0.8537	High Similarity	NPC475944
0.8506	High Similarity	NPC477782
0.8506	High Similarity	NPC51486
0.85	High Similarity	NPC189206
0.85	High Similarity	NPC262747
0.8471	Intermediate Similarity	NPC471219
0.8462	Intermediate Similarity	NPC275086
0.8462	Intermediate Similarity	NPC325229
0.8452	Intermediate Similarity	NPC96055
0.8444	Intermediate Similarity	NPC16967
0.8444	Intermediate Similarity	NPC473153
0.8427	Intermediate Similarity	NPC105490
0.8427	Intermediate Similarity	NPC191521
0.8427	Intermediate Similarity	NPC57117
0.8415	Intermediate Similarity	NPC10636
0.8409	Intermediate Similarity	NPC477783
0.8395	Intermediate Similarity	NPC474816
0.8395	Intermediate Similarity	NPC209135
0.8391	Intermediate Similarity	NPC251528
0.8391	Intermediate Similarity	NPC5509
0.8372	Intermediate Similarity	NPC473891
0.837	Intermediate Similarity	NPC477716
0.837	Intermediate Similarity	NPC38855
0.837	Intermediate Similarity	NPC477721
0.8353	Intermediate Similarity	NPC474013
0.8352	Intermediate Similarity	NPC51499
0.8333	Intermediate Similarity	NPC476927
0.8315	Intermediate Similarity	NPC472640
0.8315	Intermediate Similarity	NPC472641
0.8315	Intermediate Similarity	NPC7349
0.8295	Intermediate Similarity	NPC472642
0.8295	Intermediate Similarity	NPC281942
0.8295	Intermediate Similarity	NPC232426
0.828	Intermediate Similarity	NPC477717
0.8276	Intermediate Similarity	NPC93411
0.8261	Intermediate Similarity	NPC159763
0.8261	Intermediate Similarity	NPC278386
0.8261	Intermediate Similarity	NPC278673
0.8261	Intermediate Similarity	NPC124512
0.8261	Intermediate Similarity	NPC474440
0.8242	Intermediate Similarity	NPC165632
0.8235	Intermediate Similarity	NPC102048
0.8235	Intermediate Similarity	NPC471302
0.8235	Intermediate Similarity	NPC306951
0.8235	Intermediate Similarity	NPC32223
0.8222	Intermediate Similarity	NPC324078
0.8214	Intermediate Similarity	NPC200513
0.8214	Intermediate Similarity	NPC256112
0.8214	Intermediate Similarity	NPC155521
0.8214	Intermediate Similarity	NPC471218
0.8214	Intermediate Similarity	NPC471298
0.8214	Intermediate Similarity	NPC2524
0.8202	Intermediate Similarity	NPC141831
0.8202	Intermediate Similarity	NPC477122
0.8191	Intermediate Similarity	NPC475038
0.8191	Intermediate Similarity	NPC109195
0.8191	Intermediate Similarity	NPC472815
0.8182	Intermediate Similarity	NPC79027
0.8172	Intermediate Similarity	NPC16601
0.8172	Intermediate Similarity	NPC324841
0.8171	Intermediate Similarity	NPC184737
0.8152	Intermediate Similarity	NPC231751
0.8152	Intermediate Similarity	NPC73911
0.8152	Intermediate Similarity	NPC474343
0.8132	Intermediate Similarity	NPC209355
0.8118	Intermediate Similarity	NPC321385
0.8118	Intermediate Similarity	NPC474193
0.8118	Intermediate Similarity	NPC471297
0.8118	Intermediate Similarity	NPC477124
0.8118	Intermediate Similarity	NPC23748
0.8118	Intermediate Similarity	NPC12283
0.8111	Intermediate Similarity	NPC472303
0.8105	Intermediate Similarity	NPC471938
0.8095	Intermediate Similarity	NPC40228
0.8095	Intermediate Similarity	NPC229584
0.8095	Intermediate Similarity	NPC14203
0.8085	Intermediate Similarity	NPC303559
0.8085	Intermediate Similarity	NPC11974
0.8072	Intermediate Similarity	NPC80471
0.8072	Intermediate Similarity	NPC5908
0.8072	Intermediate Similarity	NPC100906
0.8072	Intermediate Similarity	NPC110373
0.8068	Intermediate Similarity	NPC104560
0.8068	Intermediate Similarity	NPC291665
0.8049	Intermediate Similarity	NPC132542
0.8049	Intermediate Similarity	NPC283619
0.8046	Intermediate Similarity	NPC475069
0.8046	Intermediate Similarity	NPC175145
0.8023	Intermediate Similarity	NPC474693
0.8023	Intermediate Similarity	NPC318515
0.8023	Intermediate Similarity	NPC126518
0.8023	Intermediate Similarity	NPC471301
0.8022	Intermediate Similarity	NPC201725
0.8022	Intermediate Similarity	NPC474554
0.8021	Intermediate Similarity	NPC471937
0.8	Intermediate Similarity	NPC476081
0.8	Intermediate Similarity	NPC78594
0.8	Intermediate Similarity	NPC323251
0.8	Intermediate Similarity	NPC471914
0.8	Intermediate Similarity	NPC234335
0.8	Intermediate Similarity	NPC289479
0.7979	Intermediate Similarity	NPC117685
0.7979	Intermediate Similarity	NPC472826
0.7979	Intermediate Similarity	NPC476767
0.7979	Intermediate Similarity	NPC201406
0.7979	Intermediate Similarity	NPC251680
0.7979	Intermediate Similarity	NPC474012
0.7979	Intermediate Similarity	NPC476299
0.7978	Intermediate Similarity	NPC262858
0.7978	Intermediate Similarity	NPC82876
0.7978	Intermediate Similarity	NPC146554
0.7978	Intermediate Similarity	NPC472240
0.7978	Intermediate Similarity	NPC473647
0.7976	Intermediate Similarity	NPC469802
0.7976	Intermediate Similarity	NPC268827
0.7957	Intermediate Similarity	NPC208094
0.7957	Intermediate Similarity	NPC253826
0.7957	Intermediate Similarity	NPC205143
0.7957	Intermediate Similarity	NPC53844
0.7952	Intermediate Similarity	NPC239098
0.7938	Intermediate Similarity	NPC472818
0.7935	Intermediate Similarity	NPC471915
0.7935	Intermediate Similarity	NPC111273
0.7931	Intermediate Similarity	NPC476602
0.7931	Intermediate Similarity	NPC472442
0.7931	Intermediate Similarity	NPC163606
0.7931	Intermediate Similarity	NPC35933
0.7931	Intermediate Similarity	NPC475860
0.7931	Intermediate Similarity	NPC473659
0.7931	Intermediate Similarity	NPC109528
0.7931	Intermediate Similarity	NPC329630
0.7931	Intermediate Similarity	NPC52628
0.7931	Intermediate Similarity	NPC189311
0.7931	Intermediate Similarity	NPC474694
0.7917	Intermediate Similarity	NPC187302
0.7917	Intermediate Similarity	NPC97487
0.7917	Intermediate Similarity	NPC120321
0.7917	Intermediate Similarity	NPC112009
0.7917	Intermediate Similarity	NPC10232
0.7917	Intermediate Similarity	NPC196471
0.7917	Intermediate Similarity	NPC45897
0.7917	Intermediate Similarity	NPC189588

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 NPC311070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1286
0.2-0.3	3806
0.3-0.4	2625
0.4-0.5	830
0.5-0.6	235
0.6-0.7	199
0.7-0.8	28
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD4225	Approved
0.8214	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD7640	Approved
0.7979	Intermediate Similarity	NPD7639	Approved
0.7872	Intermediate Similarity	NPD7638	Approved
0.76	Intermediate Similarity	NPD6686	Approved
0.7419	Intermediate Similarity	NPD7637	Suspended
0.7391	Intermediate Similarity	NPD6051	Approved
0.7303	Intermediate Similarity	NPD6695	Phase 3
0.7273	Intermediate Similarity	NPD7632	Discontinued
0.7253	Intermediate Similarity	NPD6409	Approved
0.7253	Intermediate Similarity	NPD5330	Approved
0.7253	Intermediate Similarity	NPD6684	Approved
0.7253	Intermediate Similarity	NPD7146	Approved
0.7253	Intermediate Similarity	NPD7334	Approved
0.7253	Intermediate Similarity	NPD7521	Approved
0.7241	Intermediate Similarity	NPD6929	Approved
0.7222	Intermediate Similarity	NPD3133	Approved
0.7222	Intermediate Similarity	NPD3665	Phase 1
0.7222	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3666	Approved
0.7216	Intermediate Similarity	NPD6083	Phase 2
0.7216	Intermediate Similarity	NPD6084	Phase 2
0.7159	Intermediate Similarity	NPD6931	Approved
0.7159	Intermediate Similarity	NPD6930	Phase 2
0.7143	Intermediate Similarity	NPD1694	Approved
0.7125	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6903	Approved
0.7093	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7748	Approved
0.7065	Intermediate Similarity	NPD3618	Phase 1
0.7059	Intermediate Similarity	NPD6924	Approved
0.7059	Intermediate Similarity	NPD6926	Approved
0.7053	Intermediate Similarity	NPD7515	Phase 2
0.7045	Intermediate Similarity	NPD7645	Phase 2
0.7037	Intermediate Similarity	NPD7115	Discovery
0.7019	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6925	Approved
0.7011	Intermediate Similarity	NPD5776	Phase 2
0.701	Intermediate Similarity	NPD5695	Phase 3
0.7	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD5344	Discontinued
0.6989	Remote Similarity	NPD7750	Discontinued
0.6989	Remote Similarity	NPD7524	Approved
0.6979	Remote Similarity	NPD6399	Phase 3
0.6977	Remote Similarity	NPD7339	Approved
0.6977	Remote Similarity	NPD6942	Approved
0.6972	Remote Similarity	NPD7328	Approved
0.6972	Remote Similarity	NPD7327	Approved
0.697	Remote Similarity	NPD5696	Approved
0.6966	Remote Similarity	NPD7514	Phase 3
0.6966	Remote Similarity	NPD7332	Phase 2
0.6947	Remote Similarity	NPD5785	Approved
0.6932	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7145	Approved
0.6915	Remote Similarity	NPD5737	Approved
0.6915	Remote Similarity	NPD6672	Approved
0.6909	Remote Similarity	NPD7516	Approved
0.6897	Remote Similarity	NPD6933	Approved
0.6893	Remote Similarity	NPD7128	Approved
0.6893	Remote Similarity	NPD5739	Approved
0.6893	Remote Similarity	NPD6675	Approved
0.6893	Remote Similarity	NPD6402	Approved
0.6889	Remote Similarity	NPD6902	Approved
0.6882	Remote Similarity	NPD5279	Phase 3
0.6882	Remote Similarity	NPD4623	Approved
0.6882	Remote Similarity	NPD4519	Discontinued
0.6875	Remote Similarity	NPD5693	Phase 1
0.6869	Remote Similarity	NPD7902	Approved
0.6854	Remote Similarity	NPD4195	Approved
0.6848	Remote Similarity	NPD4786	Approved
0.6847	Remote Similarity	NPD8294	Approved
0.6847	Remote Similarity	NPD8377	Approved
0.6842	Remote Similarity	NPD4753	Phase 2
0.6842	Remote Similarity	NPD5328	Approved
0.6837	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5701	Approved
0.6827	Remote Similarity	NPD5697	Approved
0.6809	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5778	Approved
0.6804	Remote Similarity	NPD5779	Approved
0.6792	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8380	Approved
0.6786	Remote Similarity	NPD8296	Approved
0.6786	Remote Similarity	NPD8379	Approved
0.6786	Remote Similarity	NPD8378	Approved
0.6786	Remote Similarity	NPD8335	Approved
0.6786	Remote Similarity	NPD6923	Approved
0.6786	Remote Similarity	NPD8033	Approved
0.6786	Remote Similarity	NPD6922	Approved
0.6782	Remote Similarity	NPD8264	Approved
0.6778	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7525	Registered
0.6774	Remote Similarity	NPD6893	Approved
0.6774	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6698	Approved
0.6771	Remote Similarity	NPD7838	Discovery
0.6771	Remote Similarity	NPD46	Approved
0.6762	Remote Similarity	NPD7320	Approved
0.6762	Remote Similarity	NPD6881	Approved
0.6762	Remote Similarity	NPD6899	Approved
0.6742	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7154	Phase 3
0.6733	Remote Similarity	NPD6648	Approved
0.6706	Remote Similarity	NPD7144	Approved
0.6706	Remote Similarity	NPD7143	Approved
0.6703	Remote Similarity	NPD6898	Phase 1
0.6701	Remote Similarity	NPD7087	Discontinued
0.6701	Remote Similarity	NPD6411	Approved
0.6701	Remote Similarity	NPD6079	Approved
0.6698	Remote Similarity	NPD6013	Approved
0.6698	Remote Similarity	NPD6014	Approved
0.6698	Remote Similarity	NPD6373	Approved
0.6698	Remote Similarity	NPD6372	Approved
0.6698	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD7503	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.6636	Remote Similarity	NPD7102	Approved
0.6636	Remote Similarity	NPD7290	Approved
0.6633	Remote Similarity	NPD4202	Approved
0.663	Remote Similarity	NPD5209	Approved
0.663	Remote Similarity	NPD4223	Phase 3
0.663	Remote Similarity	NPD4221	Approved
0.6629	Remote Similarity	NPD6932	Approved
0.6628	Remote Similarity	NPD7152	Approved
0.6628	Remote Similarity	NPD7151	Approved
0.6628	Remote Similarity	NPD7150	Approved
0.6604	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD5211	Phase 2
0.6596	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7509	Discontinued
0.6593	Remote Similarity	NPD4822	Approved
0.6593	Remote Similarity	NPD4819	Approved
0.6593	Remote Similarity	NPD4821	Approved
0.6593	Remote Similarity	NPD4695	Discontinued
0.6593	Remote Similarity	NPD4820	Approved
0.6591	Remote Similarity	NPD8039	Approved
0.6585	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6869	Approved
0.6574	Remote Similarity	NPD6847	Approved
0.6574	Remote Similarity	NPD6649	Approved
0.6574	Remote Similarity	NPD8130	Phase 1
0.6574	Remote Similarity	NPD6650	Approved
0.6574	Remote Similarity	NPD6617	Approved
0.6566	Remote Similarity	NPD7900	Approved
0.6566	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5208	Approved
0.6559	Remote Similarity	NPD5362	Discontinued
0.6556	Remote Similarity	NPD4271	Approved
0.6556	Remote Similarity	NPD4268	Approved
0.6552	Remote Similarity	NPD7507	Approved
0.6543	Remote Similarity	NPD4192	Approved
0.6543	Remote Similarity	NPD4191	Approved
0.6543	Remote Similarity	NPD4193	Approved
0.6543	Remote Similarity	NPD4194	Approved
0.6535	Remote Similarity	NPD4755	Approved
0.6514	Remote Similarity	NPD6882	Approved
0.6514	Remote Similarity	NPD6053	Discontinued
0.6514	Remote Similarity	NPD8297	Approved
0.6509	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6412	Phase 2
0.65	Remote Similarity	NPD5210	Approved
0.65	Remote Similarity	NPD4629	Approved
0.6495	Remote Similarity	NPD6101	Approved
0.6495	Remote Similarity	NPD6080	Approved
0.6495	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6673	Approved
0.6495	Remote Similarity	NPD6904	Approved
0.6489	Remote Similarity	NPD4197	Approved
0.6484	Remote Similarity	NPD6683	Phase 2
0.6481	Remote Similarity	NPD6371	Approved
0.6476	Remote Similarity	NPD5141	Approved
0.6471	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3573	Approved
0.6437	Remote Similarity	NPD4243	Approved
0.6436	Remote Similarity	NPD5222	Approved
0.6436	Remote Similarity	NPD5221	Approved
0.6436	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4697	Phase 3
0.6436	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5329	Approved
0.6421	Remote Similarity	NPD5363	Approved
0.6408	Remote Similarity	NPD5286	Approved
0.6408	Remote Similarity	NPD4700	Approved
0.6408	Remote Similarity	NPD4696	Approved
0.6408	Remote Similarity	NPD5285	Approved
0.6387	Remote Similarity	NPD7319	Approved
0.6383	Remote Similarity	NPD5331	Approved
0.6383	Remote Similarity	NPD5332	Approved
0.6374	Remote Similarity	NPD3617	Approved
0.6373	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD5281	Approved
0.6354	Remote Similarity	NPD4689	Approved
0.6354	Remote Similarity	NPD4693	Phase 3

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