NPASS Compound

Structure

NPC472810 OpenBabel07101719152D 24 26 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 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 1 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 0.9781 -0.2079 0.0000 C 0 0 3 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 1.7213 0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 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 12 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 6 0 0 0 15 21 1 6 0 0 0 16 19 1 0 0 0 0 16 20 1 6 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	356.058
LogP:	3.982
LogD:	3.35
LogS:	-3.804
# Rotatable Bonds:	3
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.686
Synthetic Accessibility Score:	4.55
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.932
MDCK Permeability:	1.6988982679322362e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.561
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.673
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	91.06989288330078%
Volume Distribution (VD):	1.333
Pgp-substrate:	11.639184951782227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.204
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.616
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	11.036
Half-life (T1/2):	0.344

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.241
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.827
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.689
Carcinogencity:	0.924
Eye Corrosion:	0.004
Eye Irritation:	0.132
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC472810

Natural Product ID:	NPC472810
*Common Name:**	HYOANESYDNMXHG-QHZHISOMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HYOANESYDNMXHG-QHZHISOMSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-12-6-7-16-19(2,3)8-5-9-20(16,4)14(12)11-15(21)13-10-17(22)24-18(13)23/h10,14-16,18,21,23H,1,5-9,11H2,2-4H3/t14-,15-,16-,18?,20+/m0/s1
SMILES:	O=C1C=C(C(O1)O)[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:	CHEMBL3586263
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	=	67.0	%	PMID[466509]
NPT171	Cell Line	MRC5	Homo sapiens	GI	=	19.0	%	PMID[466509]
NPT393	Cell Line	HCT-116	Homo sapiens	GI	=	90.0	%	PMID[466509]
NPT393	Cell Line	HCT-116	Homo sapiens	GI	=	1.0	%	PMID[466509]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	24000.0	nM	PMID[466509]
NPT3145	Organism	Bacillus subtilis subsp. spizizenii ATCC 6633	Bacillus subtilis subsp. spizizenii ATCC 6633	MIC	=	12000.0	nM	PMID[466509]
NPT4843	Organism	Corynebacterium striatum	Corynebacterium striatum	MIC	=	96000.0	nM	PMID[466509]
NPT4075	Organism	Enterococcus avium	Enterococcus avium	MIC	=	96000.0	nM	PMID[466509]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	96000.0	nM	PMID[466509]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	=	48000.0	nM	PMID[466509]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	96000.0	nM	PMID[466509]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	96000.0	nM	PMID[466509]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	96000.0	nM	PMID[466509]
NPT4844	Organism	Enterococcus gallinarum	Enterococcus gallinarum	MIC	>	96000.0	nM	PMID[466509]
NPT4844	Organism	Enterococcus gallinarum	Enterococcus gallinarum	MIC	=	96000.0	nM	PMID[466509]
NPT3721	Organism	Enterococcus hirae	Enterococcus hirae	MIC	>	96000.0	nM	PMID[466509]
NPT4845	Organism	Listeria innocua	Listeria innocua	MIC	>	96000.0	nM	PMID[466509]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	=	96000.0	nM	PMID[466509]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	48000.0	nM	PMID[466509]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	48000.0	nM	PMID[466509]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	24000.0	nM	PMID[466509]
NPT4839	Organism	Staphylococcus intermedius	Staphylococcus intermedius	MIC	=	24000.0	nM	PMID[466509]
NPT4840	Organism	Staphylococcus lugdunensis	Staphylococcus lugdunensis	MIC	=	48000.0	nM	PMID[466509]
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	=	48000.0	nM	PMID[466509]
NPT4428	Organism	Staphylococcus sciuri	Staphylococcus sciuri	MIC	=	96000.0	nM	PMID[466509]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	24000.0	nM	PMID[466509]

☑ 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 NPC472810 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	177
0.1-0.2	1139
0.2-0.3	4247
0.3-0.4	11594
0.4-0.5	11365
0.5-0.6	6640
0.6-0.7	6101
0.7-0.8	1238
0.8-0.85	145
0.85-0.9	33
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472809
0.9643	High Similarity	NPC470734
0.9535	High Similarity	NPC472812
0.9425	High Similarity	NPC469697
0.9419	High Similarity	NPC472811
0.939	High Similarity	NPC311070
0.9294	High Similarity	NPC474629
0.9213	High Similarity	NPC162346
0.9205	High Similarity	NPC298973
0.9205	High Similarity	NPC470255
0.9205	High Similarity	NPC104925
0.9167	High Similarity	NPC473251
0.9167	High Similarity	NPC42586
0.9111	High Similarity	NPC475709
0.9111	High Similarity	NPC477719
0.9111	High Similarity	NPC477718
0.9101	High Similarity	NPC472441
0.908	High Similarity	NPC477782
0.9059	High Similarity	NPC131813
0.8977	High Similarity	NPC477783
0.8913	High Similarity	NPC477721
0.8913	High Similarity	NPC477716
0.8864	High Similarity	NPC78973
0.8851	High Similarity	NPC472378
0.8824	High Similarity	NPC471302
0.8817	High Similarity	NPC477717
0.881	High Similarity	NPC471298
0.8804	High Similarity	NPC474440
0.8778	High Similarity	NPC324078
0.8764	High Similarity	NPC477122
0.8764	High Similarity	NPC329842
0.875	High Similarity	NPC251528
0.8723	High Similarity	NPC472815
0.871	High Similarity	NPC324841
0.8706	High Similarity	NPC471297
0.8706	High Similarity	NPC42476
0.8605	High Similarity	NPC126518
0.8605	High Similarity	NPC471301
0.8588	High Similarity	NPC323251
0.8571	High Similarity	NPC474554
0.8556	High Similarity	NPC472814
0.8556	High Similarity	NPC177037
0.8506	High Similarity	NPC472442
0.8506	High Similarity	NPC163606
0.8488	Intermediate Similarity	NPC472440
0.8488	Intermediate Similarity	NPC472377
0.8462	Intermediate Similarity	NPC139692
0.8462	Intermediate Similarity	NPC53555
0.8462	Intermediate Similarity	NPC205034
0.8462	Intermediate Similarity	NPC472640
0.8462	Intermediate Similarity	NPC152778
0.8462	Intermediate Similarity	NPC162615
0.8462	Intermediate Similarity	NPC472641
0.8444	Intermediate Similarity	NPC232426
0.8444	Intermediate Similarity	NPC182136
0.8444	Intermediate Similarity	NPC472642
0.8444	Intermediate Similarity	NPC281942
0.8404	Intermediate Similarity	NPC473154
0.8387	Intermediate Similarity	NPC165632
0.8387	Intermediate Similarity	NPC234993
0.8387	Intermediate Similarity	NPC240673
0.8387	Intermediate Similarity	NPC242848
0.8387	Intermediate Similarity	NPC17578
0.8387	Intermediate Similarity	NPC134072
0.837	Intermediate Similarity	NPC477722
0.837	Intermediate Similarity	NPC474555
0.8353	Intermediate Similarity	NPC10636
0.8352	Intermediate Similarity	NPC72845
0.8352	Intermediate Similarity	NPC141831
0.8333	Intermediate Similarity	NPC174342
0.8333	Intermediate Similarity	NPC50488
0.8333	Intermediate Similarity	NPC474396
0.8316	Intermediate Similarity	NPC477720
0.8316	Intermediate Similarity	NPC16601
0.8315	Intermediate Similarity	NPC166857
0.8295	Intermediate Similarity	NPC106416
0.8295	Intermediate Similarity	NPC471795
0.8295	Intermediate Similarity	NPC86316
0.8295	Intermediate Similarity	NPC30984
0.8295	Intermediate Similarity	NPC329630
0.8295	Intermediate Similarity	NPC65661
0.8283	Intermediate Similarity	NPC38948
0.828	Intermediate Similarity	NPC276110
0.8276	Intermediate Similarity	NPC79945
0.8276	Intermediate Similarity	NPC474809
0.8261	Intermediate Similarity	NPC472303
0.8261	Intermediate Similarity	NPC115021
0.8256	Intermediate Similarity	NPC170303
0.8256	Intermediate Similarity	NPC475944
0.8247	Intermediate Similarity	NPC471938
0.8247	Intermediate Similarity	NPC120009
0.8242	Intermediate Similarity	NPC469403
0.8242	Intermediate Similarity	NPC221111
0.8242	Intermediate Similarity	NPC280149
0.8242	Intermediate Similarity	NPC51486
0.8242	Intermediate Similarity	NPC310479
0.8242	Intermediate Similarity	NPC253186
0.8235	Intermediate Similarity	NPC242767
0.8229	Intermediate Similarity	NPC471075
0.8229	Intermediate Similarity	NPC198992
0.8214	Intermediate Similarity	NPC473756
0.8211	Intermediate Similarity	NPC325229
0.8211	Intermediate Similarity	NPC275086
0.8202	Intermediate Similarity	NPC329692
0.8202	Intermediate Similarity	NPC474062
0.82	Intermediate Similarity	NPC206618
0.8191	Intermediate Similarity	NPC470801
0.8191	Intermediate Similarity	NPC16967
0.8191	Intermediate Similarity	NPC473153
0.8182	Intermediate Similarity	NPC475074
0.8182	Intermediate Similarity	NPC470800
0.8172	Intermediate Similarity	NPC105490
0.8172	Intermediate Similarity	NPC191521
0.8172	Intermediate Similarity	NPC57117
0.8163	Intermediate Similarity	NPC471937
0.8152	Intermediate Similarity	NPC289479
0.8152	Intermediate Similarity	NPC78594
0.8144	Intermediate Similarity	NPC121423
0.8144	Intermediate Similarity	NPC471914
0.814	Intermediate Similarity	NPC281880
0.8132	Intermediate Similarity	NPC5509
0.8125	Intermediate Similarity	NPC472826
0.8125	Intermediate Similarity	NPC476767
0.8125	Intermediate Similarity	NPC38855
0.8118	Intermediate Similarity	NPC209135
0.8118	Intermediate Similarity	NPC474816
0.8111	Intermediate Similarity	NPC471796
0.8111	Intermediate Similarity	NPC312561
0.8105	Intermediate Similarity	NPC51499
0.8105	Intermediate Similarity	NPC98112
0.81	Intermediate Similarity	NPC177524
0.81	Intermediate Similarity	NPC219900
0.81	Intermediate Similarity	NPC476765
0.81	Intermediate Similarity	NPC392
0.809	Intermediate Similarity	NPC474013
0.809	Intermediate Similarity	NPC217394
0.8085	Intermediate Similarity	NPC13924
0.8085	Intermediate Similarity	NPC471915
0.8081	Intermediate Similarity	NPC218158
0.8081	Intermediate Similarity	NPC472818
0.8068	Intermediate Similarity	NPC476927
0.8065	Intermediate Similarity	NPC7349
0.8061	Intermediate Similarity	NPC45897
0.8046	Intermediate Similarity	NPC159148
0.8022	Intermediate Similarity	NPC93411
0.8021	Intermediate Similarity	NPC159763
0.8021	Intermediate Similarity	NPC278386
0.8021	Intermediate Similarity	NPC124512
0.8021	Intermediate Similarity	NPC278673
0.8	Intermediate Similarity	NPC262747
0.8	Intermediate Similarity	NPC471219
0.8	Intermediate Similarity	NPC472820
0.8	Intermediate Similarity	NPC471205
0.8	Intermediate Similarity	NPC189206
0.798	Intermediate Similarity	NPC472819
0.7979	Intermediate Similarity	NPC475572
0.7978	Intermediate Similarity	NPC96055
0.7978	Intermediate Similarity	NPC474693
0.7978	Intermediate Similarity	NPC102048
0.7959	Intermediate Similarity	NPC475038
0.7959	Intermediate Similarity	NPC109195
0.7955	Intermediate Similarity	NPC109938
0.7955	Intermediate Similarity	NPC256112
0.7955	Intermediate Similarity	NPC122945
0.7955	Intermediate Similarity	NPC2524
0.7955	Intermediate Similarity	NPC471218
0.7955	Intermediate Similarity	NPC324170
0.7955	Intermediate Similarity	NPC200513
0.7941	Intermediate Similarity	NPC476766
0.7938	Intermediate Similarity	NPC228251
0.7938	Intermediate Similarity	NPC472644
0.7938	Intermediate Similarity	NPC161527
0.7938	Intermediate Similarity	NPC477968
0.7938	Intermediate Similarity	NPC219285
0.7938	Intermediate Similarity	NPC477972
0.7938	Intermediate Similarity	NPC20113
0.7938	Intermediate Similarity	NPC477971
0.7935	Intermediate Similarity	NPC293044
0.7931	Intermediate Similarity	NPC206062
0.7921	Intermediate Similarity	NPC470024
0.7917	Intermediate Similarity	NPC73911
0.7917	Intermediate Similarity	NPC474343
0.7917	Intermediate Similarity	NPC231751
0.7912	Intermediate Similarity	NPC473891
0.79	Intermediate Similarity	NPC82251
0.79	Intermediate Similarity	NPC239961
0.7895	Intermediate Similarity	NPC209355
0.7889	Intermediate Similarity	NPC471300
0.7889	Intermediate Similarity	NPC473659
0.7889	Intermediate Similarity	NPC474694
0.7889	Intermediate Similarity	NPC119001
0.7889	Intermediate Similarity	NPC474860
0.7889	Intermediate Similarity	NPC475860
0.7889	Intermediate Similarity	NPC253604
0.7879	Intermediate Similarity	NPC281378
0.7872	Intermediate Similarity	NPC242069
0.7872	Intermediate Similarity	NPC156553
0.7872	Intermediate Similarity	NPC166346
0.7865	Intermediate Similarity	NPC23748
0.7865	Intermediate Similarity	NPC12283

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 NPC472810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1371
0.2-0.3	3846
0.3-0.4	2553
0.4-0.5	784
0.5-0.6	245
0.6-0.7	186
0.7-0.8	12
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
0.8605	High Similarity	NPD6400	Clinical (unspecified phase)
0.81	Intermediate Similarity	NPD6686	Approved
0.8021	Intermediate Similarity	NPD4225	Approved
0.7955	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7640	Approved
0.7755	Intermediate Similarity	NPD7639	Approved
0.7653	Intermediate Similarity	NPD7638	Approved
0.7431	Intermediate Similarity	NPD7327	Approved
0.7431	Intermediate Similarity	NPD7328	Approved
0.7364	Intermediate Similarity	NPD7516	Approved
0.7297	Intermediate Similarity	NPD8377	Approved
0.7297	Intermediate Similarity	NPD8294	Approved
0.7232	Intermediate Similarity	NPD8378	Approved
0.7232	Intermediate Similarity	NPD8380	Approved
0.7232	Intermediate Similarity	NPD8335	Approved
0.7232	Intermediate Similarity	NPD8033	Approved
0.7232	Intermediate Similarity	NPD8379	Approved
0.7232	Intermediate Similarity	NPD8296	Approved
0.7216	Intermediate Similarity	NPD7637	Suspended
0.7188	Intermediate Similarity	NPD6051	Approved
0.7097	Intermediate Similarity	NPD6695	Phase 3
0.7087	Intermediate Similarity	NPD7632	Discontinued
0.708	Intermediate Similarity	NPD7503	Approved
0.703	Intermediate Similarity	NPD6084	Phase 2
0.703	Intermediate Similarity	NPD6083	Phase 2
0.7021	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7507	Approved
0.6981	Remote Similarity	NPD6412	Phase 2
0.69	Remote Similarity	NPD7748	Approved
0.6875	Remote Similarity	NPD7115	Discovery
0.6875	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD7146	Approved
0.6875	Remote Similarity	NPD5330	Approved
0.6875	Remote Similarity	NPD6684	Approved
0.6875	Remote Similarity	NPD7521	Approved
0.6869	Remote Similarity	NPD7515	Phase 2
0.6852	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6929	Approved
0.6842	Remote Similarity	NPD3133	Approved
0.6842	Remote Similarity	NPD3666	Approved
0.6842	Remote Similarity	NPD3665	Phase 1
0.6832	Remote Similarity	NPD5695	Phase 3
0.6827	Remote Similarity	NPD5344	Discontinued
0.6807	Remote Similarity	NPD7319	Approved
0.6804	Remote Similarity	NPD7750	Discontinued
0.6804	Remote Similarity	NPD7524	Approved
0.68	Remote Similarity	NPD6399	Phase 3
0.6796	Remote Similarity	NPD5696	Approved
0.6774	Remote Similarity	NPD6931	Approved
0.6774	Remote Similarity	NPD6930	Phase 2
0.6771	Remote Similarity	NPD1694	Approved
0.6768	Remote Similarity	NPD5785	Approved
0.6735	Remote Similarity	NPD5737	Approved
0.6735	Remote Similarity	NPD6672	Approved
0.6735	Remote Similarity	NPD6903	Approved
0.6735	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7128	Approved
0.6729	Remote Similarity	NPD6402	Approved
0.6729	Remote Similarity	NPD5739	Approved
0.6729	Remote Similarity	NPD6675	Approved
0.6706	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD3618	Phase 1
0.67	Remote Similarity	NPD5693	Phase 1
0.6699	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5779	Approved
0.6634	Remote Similarity	NPD5778	Approved
0.6632	Remote Similarity	NPD3667	Approved
0.663	Remote Similarity	NPD6925	Approved
0.663	Remote Similarity	NPD5776	Phase 2
0.6606	Remote Similarity	NPD7320	Approved
0.6606	Remote Similarity	NPD6881	Approved
0.6606	Remote Similarity	NPD6899	Approved
0.66	Remote Similarity	NPD46	Approved
0.66	Remote Similarity	NPD6698	Approved
0.66	Remote Similarity	NPD7838	Discovery
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7525	Registered
0.6596	Remote Similarity	NPD7514	Phase 3
0.6596	Remote Similarity	NPD7332	Phase 2
0.6593	Remote Similarity	NPD7339	Approved
0.6593	Remote Similarity	NPD6942	Approved
0.6571	Remote Similarity	NPD6648	Approved
0.6562	Remote Similarity	NPD7154	Phase 3
0.6559	Remote Similarity	NPD7145	Approved
0.6559	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6373	Approved
0.6545	Remote Similarity	NPD6372	Approved
0.6545	Remote Similarity	NPD6012	Approved
0.6545	Remote Similarity	NPD6013	Approved
0.6545	Remote Similarity	NPD6014	Approved
0.6535	Remote Similarity	NPD7087	Discontinued
0.6535	Remote Similarity	NPD6411	Approved
0.6531	Remote Similarity	NPD4623	Approved
0.6531	Remote Similarity	NPD5279	Phase 3
0.6531	Remote Similarity	NPD4519	Discontinued
0.6526	Remote Similarity	NPD6902	Approved
0.6522	Remote Similarity	NPD6933	Approved
0.65	Remote Similarity	NPD5328	Approved
0.6495	Remote Similarity	NPD4786	Approved
0.6489	Remote Similarity	NPD4195	Approved
0.6486	Remote Similarity	NPD7102	Approved
0.6486	Remote Similarity	NPD7290	Approved
0.6486	Remote Similarity	NPD6883	Approved
0.6465	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.646	Remote Similarity	NPD8133	Approved
0.6458	Remote Similarity	NPD5209	Approved
0.6455	Remote Similarity	NPD6011	Approved
0.6449	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD8130	Phase 1
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.6429	Remote Similarity	NPD6847	Approved
0.6429	Remote Similarity	NPD6617	Approved
0.6429	Remote Similarity	NPD6893	Approved
0.6429	Remote Similarity	NPD6869	Approved
0.6421	Remote Similarity	NPD4819	Approved
0.6421	Remote Similarity	NPD4821	Approved
0.6421	Remote Similarity	NPD4822	Approved
0.6421	Remote Similarity	NPD4820	Approved
0.6421	Remote Similarity	NPD4695	Discontinued
0.6413	Remote Similarity	NPD8264	Approved
0.6408	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7900	Approved
0.6404	Remote Similarity	NPD6923	Approved
0.6404	Remote Similarity	NPD6922	Approved
0.6392	Remote Similarity	NPD5362	Discontinued
0.6383	Remote Similarity	NPD4268	Approved
0.6383	Remote Similarity	NPD4271	Approved
0.6381	Remote Similarity	NPD4755	Approved
0.6373	Remote Similarity	NPD6079	Approved
0.6372	Remote Similarity	NPD8297	Approved
0.6372	Remote Similarity	NPD6053	Discontinued
0.6364	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6898	Phase 1
0.6346	Remote Similarity	NPD4629	Approved
0.6346	Remote Similarity	NPD5210	Approved
0.6339	Remote Similarity	NPD6371	Approved
0.6337	Remote Similarity	NPD6080	Approved
0.6337	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6904	Approved
0.6337	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD6673	Approved
0.6333	Remote Similarity	NPD7144	Approved
0.6333	Remote Similarity	NPD7143	Approved
0.633	Remote Similarity	NPD5141	Approved
0.6311	Remote Similarity	NPD4202	Approved
0.6289	Remote Similarity	NPD4223	Phase 3
0.6289	Remote Similarity	NPD4221	Approved
0.6286	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4697	Phase 3
0.6286	Remote Similarity	NPD5222	Approved
0.6286	Remote Similarity	NPD5221	Approved
0.6286	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6932	Approved
0.6264	Remote Similarity	NPD7151	Approved
0.6264	Remote Similarity	NPD7152	Approved
0.6264	Remote Similarity	NPD7150	Approved
0.6263	Remote Similarity	NPD5363	Approved
0.6263	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5286	Approved
0.6262	Remote Similarity	NPD4700	Approved
0.6262	Remote Similarity	NPD4696	Approved
0.6262	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD7509	Discontinued
0.625	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8328	Phase 3
0.6238	Remote Similarity	NPD5208	Approved
0.6237	Remote Similarity	NPD8039	Approved
0.623	Remote Similarity	NPD8293	Discontinued
0.6226	Remote Similarity	NPD5173	Approved
0.6224	Remote Similarity	NPD5331	Approved
0.6224	Remote Similarity	NPD5332	Approved
0.6214	Remote Similarity	NPD8035	Phase 2
0.6214	Remote Similarity	NPD8034	Phase 2
0.6214	Remote Similarity	NPD5284	Approved
0.6214	Remote Similarity	NPD5281	Approved
0.6207	Remote Similarity	NPD6274	Approved
0.6207	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4249	Approved
0.619	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4790	Discontinued
0.6179	Remote Similarity	NPD7736	Approved
0.6176	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6370	Approved
0.6163	Remote Similarity	NPD4193	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