NPASS Compound

Structure

NPC474323 OpenBabel07101718182D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.9726 -2.6765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8136 -3.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1092 -1.0352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4349 -1.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0215 -2.9855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2784 -2.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8605 0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5227 0.5759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 -2.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8387 0.6034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1754 1.5709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 -1.3383 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 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 6 10 1 0 0 0 0 7 13 1 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 18 1 0 0 0 0 9 16 1 0 0 0 0 10 19 1 6 0 0 0 11 17 1 0 0 0 0 12 6 1 6 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 1 0 0 0 14 19 1 6 0 0 0 14 20 1 0 0 0 0 15 11 1 1 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 5 1 6 0 0 0 18 26 1 0 0 0 0 19 23 1 6 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.18
Volume:	365.133
LogP:	1.506
LogD:	0.842
LogS:	-3.006
# Rotatable Bonds:	3
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	6.066
Fsp3:	0.789
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.019
MDCK Permeability:	6.63859027554281e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.281
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.149
Plasma Protein Binding (PPB):	59.08152389526367%
Volume Distribution (VD):	1.422
Pgp-substrate:	53.93051528930664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.748
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.336
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	7.481
Half-life (T1/2):	0.31

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.806
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.291
Maximum Recommended Daily Dose:	0.58
Skin Sensitization:	0.28
Carcinogencity:	0.845
Eye Corrosion:	0.004
Eye Irritation:	0.046
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC474323

Natural Product ID:	NPC474323
*Common Name:**	UFLGQPOBCWRADC-YCIRREICSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UFLGQPOBCWRADC-YCIRREICSA-N
Standard InCHI:	InChI=1S/C19H28O7/c1-9(2)16(21)25-13-7-18(5)8-14(20)19(23,26-18)10(3)6-12-15(13)11(4)17(22)24-12/h9-10,12-15,20,23H,4,6-8H2,1-3,5H3/t10-,12+,13+,14+,15-,18+,19-/m0/s1
SMILES:	CC1CC2C(C(CC3(CC(C1(O3)O)O)C)OC(=O)C(C)C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465253
PubChem CID:	44566955
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides 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
NPO19764	Tithonia diversifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975495]
NPO19764	Tithonia diversifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO19764	Tithonia diversifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO19764	Tithonia diversifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19764	Tithonia diversifolia	Species	Asteraceae	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10.0	ug.mL-1	PMID[558298]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[558298]

☑ 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 NPC474323 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	247
0.1-0.2	1728
0.2-0.3	6058
0.3-0.4	14210
0.4-0.5	9927
0.5-0.6	7536
0.6-0.7	2300
0.7-0.8	650
0.8-0.85	20
0.85-0.9	10
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC206614
0.9524	High Similarity	NPC162071
0.9186	High Similarity	NPC186148
0.908	High Similarity	NPC177629
0.908	High Similarity	NPC58219
0.9022	High Similarity	NPC187268
0.8977	High Similarity	NPC92974
0.8778	High Similarity	NPC12172
0.8778	High Similarity	NPC208886
0.8681	High Similarity	NPC81419
0.8681	High Similarity	NPC179746
0.8587	High Similarity	NPC474338
0.8571	High Similarity	NPC184463
0.8539	High Similarity	NPC190753
0.8478	Intermediate Similarity	NPC212486
0.8478	Intermediate Similarity	NPC475912
0.8444	Intermediate Similarity	NPC202672
0.8427	Intermediate Similarity	NPC475019
0.8427	Intermediate Similarity	NPC474949
0.8409	Intermediate Similarity	NPC474780
0.8387	Intermediate Similarity	NPC190294
0.837	Intermediate Similarity	NPC30515
0.837	Intermediate Similarity	NPC475881
0.837	Intermediate Similarity	NPC70251
0.8352	Intermediate Similarity	NPC473564
0.8352	Intermediate Similarity	NPC307411
0.8316	Intermediate Similarity	NPC471150
0.8316	Intermediate Similarity	NPC474313
0.8315	Intermediate Similarity	NPC329749
0.8315	Intermediate Similarity	NPC47958
0.8315	Intermediate Similarity	NPC149725
0.8315	Intermediate Similarity	NPC304509
0.8298	Intermediate Similarity	NPC36954
0.8298	Intermediate Similarity	NPC14961
0.8298	Intermediate Similarity	NPC472873
0.8298	Intermediate Similarity	NPC270013
0.828	Intermediate Similarity	NPC476300
0.8261	Intermediate Similarity	NPC51004
0.8247	Intermediate Similarity	NPC473332
0.8242	Intermediate Similarity	NPC217983
0.8242	Intermediate Similarity	NPC207114
0.8229	Intermediate Similarity	NPC249171
0.8229	Intermediate Similarity	NPC49833
0.8222	Intermediate Similarity	NPC474762
0.8222	Intermediate Similarity	NPC476015
0.8211	Intermediate Similarity	NPC76862
0.8211	Intermediate Similarity	NPC158416
0.8211	Intermediate Similarity	NPC476009
0.8211	Intermediate Similarity	NPC39859
0.8211	Intermediate Similarity	NPC470883
0.8202	Intermediate Similarity	NPC3464
0.8202	Intermediate Similarity	NPC475963
0.8202	Intermediate Similarity	NPC151176
0.8191	Intermediate Similarity	NPC474035
0.8191	Intermediate Similarity	NPC71589
0.8191	Intermediate Similarity	NPC81386
0.8172	Intermediate Similarity	NPC184063
0.8163	Intermediate Similarity	NPC86077
0.8152	Intermediate Similarity	NPC215556
0.8152	Intermediate Similarity	NPC173926
0.8144	Intermediate Similarity	NPC70865
0.8132	Intermediate Similarity	NPC5130
0.8125	Intermediate Similarity	NPC304445
0.8125	Intermediate Similarity	NPC328562
0.8125	Intermediate Similarity	NPC323421
0.8125	Intermediate Similarity	NPC181151
0.8125	Intermediate Similarity	NPC236580
0.8105	Intermediate Similarity	NPC471141
0.8105	Intermediate Similarity	NPC475900
0.8081	Intermediate Similarity	NPC473148
0.8065	Intermediate Similarity	NPC297474
0.8065	Intermediate Similarity	NPC476004
0.8065	Intermediate Similarity	NPC54065
0.8065	Intermediate Similarity	NPC474761
0.8065	Intermediate Similarity	NPC19087
0.8065	Intermediate Similarity	NPC216284
0.8043	Intermediate Similarity	NPC79549
0.8041	Intermediate Similarity	NPC474213
0.8041	Intermediate Similarity	NPC473326
0.8022	Intermediate Similarity	NPC187661
0.8022	Intermediate Similarity	NPC470242
0.8021	Intermediate Similarity	NPC279621
0.8021	Intermediate Similarity	NPC31645
0.8021	Intermediate Similarity	NPC476315
0.798	Intermediate Similarity	NPC80144
0.7979	Intermediate Similarity	NPC133888
0.7979	Intermediate Similarity	NPC470373
0.7979	Intermediate Similarity	NPC35959
0.7979	Intermediate Similarity	NPC171360
0.7979	Intermediate Similarity	NPC293001
0.7979	Intermediate Similarity	NPC131209
0.7979	Intermediate Similarity	NPC470379
0.7979	Intermediate Similarity	NPC57304
0.7979	Intermediate Similarity	NPC29821
0.7979	Intermediate Similarity	NPC133698
0.7979	Intermediate Similarity	NPC63193
0.7959	Intermediate Similarity	NPC471381
0.7959	Intermediate Similarity	NPC186861
0.7957	Intermediate Similarity	NPC155935
0.7957	Intermediate Similarity	NPC38392
0.7957	Intermediate Similarity	NPC474951
0.7938	Intermediate Similarity	NPC311904
0.7938	Intermediate Similarity	NPC471462
0.7935	Intermediate Similarity	NPC118601
0.7917	Intermediate Similarity	NPC213698
0.7917	Intermediate Similarity	NPC304886
0.7895	Intermediate Similarity	NPC472874
0.7895	Intermediate Similarity	NPC475838
0.7895	Intermediate Similarity	NPC475788
0.7895	Intermediate Similarity	NPC125674
0.7895	Intermediate Similarity	NPC228451
0.7889	Intermediate Similarity	NPC239308
0.7889	Intermediate Similarity	NPC128429
0.7879	Intermediate Similarity	NPC67296
0.7879	Intermediate Similarity	NPC476270
0.7879	Intermediate Similarity	NPC150923
0.7872	Intermediate Similarity	NPC80875
0.7872	Intermediate Similarity	NPC475855
0.7872	Intermediate Similarity	NPC473619
0.7872	Intermediate Similarity	NPC35809
0.7857	Intermediate Similarity	NPC45125
0.7849	Intermediate Similarity	NPC178875
0.7841	Intermediate Similarity	NPC19841
0.7835	Intermediate Similarity	NPC473859
0.7835	Intermediate Similarity	NPC474297
0.7835	Intermediate Similarity	NPC306041
0.7822	Intermediate Similarity	NPC474917
0.7822	Intermediate Similarity	NPC100487
0.7812	Intermediate Similarity	NPC127019
0.7812	Intermediate Similarity	NPC474247
0.7812	Intermediate Similarity	NPC57405
0.7812	Intermediate Similarity	NPC198853
0.7812	Intermediate Similarity	NPC477131
0.7812	Intermediate Similarity	NPC303942
0.7802	Intermediate Similarity	NPC194859
0.7802	Intermediate Similarity	NPC224386
0.78	Intermediate Similarity	NPC320019
0.78	Intermediate Similarity	NPC474747
0.78	Intermediate Similarity	NPC324017
0.78	Intermediate Similarity	NPC471148
0.7789	Intermediate Similarity	NPC155215
0.7789	Intermediate Similarity	NPC469627
0.7789	Intermediate Similarity	NPC475925
0.7789	Intermediate Similarity	NPC329952
0.7789	Intermediate Similarity	NPC122057
0.7789	Intermediate Similarity	NPC473321
0.7778	Intermediate Similarity	NPC288876
0.7778	Intermediate Similarity	NPC246076
0.7778	Intermediate Similarity	NPC103171
0.7767	Intermediate Similarity	NPC475960
0.7766	Intermediate Similarity	NPC474032
0.7766	Intermediate Similarity	NPC151770
0.7766	Intermediate Similarity	NPC295312
0.7755	Intermediate Similarity	NPC111348
0.7755	Intermediate Similarity	NPC161493
0.7753	Intermediate Similarity	NPC474981
0.7745	Intermediate Similarity	NPC54737
0.7745	Intermediate Similarity	NPC44004
0.7745	Intermediate Similarity	NPC243998
0.7742	Intermediate Similarity	NPC231889
0.7742	Intermediate Similarity	NPC160138
0.7742	Intermediate Similarity	NPC248602
0.7732	Intermediate Similarity	NPC170120
0.7732	Intermediate Similarity	NPC52044
0.7732	Intermediate Similarity	NPC224689
0.7732	Intermediate Similarity	NPC475659
0.7732	Intermediate Similarity	NPC163228
0.7732	Intermediate Similarity	NPC167893
0.7732	Intermediate Similarity	NPC476053
0.7732	Intermediate Similarity	NPC67584
0.7732	Intermediate Similarity	NPC107476
0.7723	Intermediate Similarity	NPC475928
0.7723	Intermediate Similarity	NPC61442
0.7723	Intermediate Similarity	NPC475945
0.7723	Intermediate Similarity	NPC475871
0.7723	Intermediate Similarity	NPC124881
0.7717	Intermediate Similarity	NPC21469
0.7717	Intermediate Similarity	NPC255307
0.7717	Intermediate Similarity	NPC204105
0.7717	Intermediate Similarity	NPC284534
0.7717	Intermediate Similarity	NPC300082
0.7708	Intermediate Similarity	NPC295204
0.7708	Intermediate Similarity	NPC60386
0.7708	Intermediate Similarity	NPC288240
0.7708	Intermediate Similarity	NPC473263
0.7708	Intermediate Similarity	NPC258216
0.7708	Intermediate Similarity	NPC162205
0.7708	Intermediate Similarity	NPC473273
0.7708	Intermediate Similarity	NPC473234
0.7708	Intermediate Similarity	NPC308656
0.7708	Intermediate Similarity	NPC273579
0.77	Intermediate Similarity	NPC164598
0.77	Intermediate Similarity	NPC185141
0.77	Intermediate Similarity	NPC110443
0.77	Intermediate Similarity	NPC201718
0.77	Intermediate Similarity	NPC15993
0.77	Intermediate Similarity	NPC474339
0.77	Intermediate Similarity	NPC46998
0.77	Intermediate Similarity	NPC128733
0.77	Intermediate Similarity	NPC47880

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 NPC474323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	2498
0.2-0.3	3796
0.3-0.4	1751
0.4-0.5	554
0.5-0.6	210
0.6-0.7	36
0.7-0.8	1
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
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.75	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1695	Approved
0.7143	Intermediate Similarity	NPD7838	Discovery
0.713	Intermediate Similarity	NPD6371	Approved
0.7103	Intermediate Similarity	NPD6686	Approved
0.703	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6637	Remote Similarity	NPD8133	Approved
0.6602	Remote Similarity	NPD5282	Discontinued
0.6566	Remote Similarity	NPD4249	Approved
0.6542	Remote Similarity	NPD5344	Discontinued
0.6525	Remote Similarity	NPD8516	Approved
0.6525	Remote Similarity	NPD8517	Approved
0.6525	Remote Similarity	NPD8515	Approved
0.6525	Remote Similarity	NPD8513	Phase 3
0.65	Remote Similarity	NPD4251	Approved
0.65	Remote Similarity	NPD4250	Approved
0.6429	Remote Similarity	NPD7154	Phase 3
0.6429	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6053	Discontinued
0.6387	Remote Similarity	NPD8269	Approved
0.6387	Remote Similarity	NPD8267	Approved
0.6387	Remote Similarity	NPD8266	Approved
0.6387	Remote Similarity	NPD8268	Approved
0.6339	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7507	Approved
0.6311	Remote Similarity	NPD5785	Approved
0.63	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5362	Discontinued
0.626	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD6412	Phase 2
0.6228	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5369	Approved
0.619	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD5778	Approved
0.6186	Remote Similarity	NPD7115	Discovery
0.6168	Remote Similarity	NPD7839	Suspended
0.6162	Remote Similarity	NPD6435	Approved
0.616	Remote Similarity	NPD7319	Approved
0.6148	Remote Similarity	NPD7642	Approved
0.6147	Remote Similarity	NPD6648	Approved
0.6139	Remote Similarity	NPD5363	Approved
0.6134	Remote Similarity	NPD7641	Discontinued
0.6122	Remote Similarity	NPD4820	Approved
0.6122	Remote Similarity	NPD4819	Approved
0.6122	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4821	Approved
0.6122	Remote Similarity	NPD4822	Approved
0.6098	Remote Similarity	NPD7492	Approved
0.6077	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7638	Approved
0.6048	Remote Similarity	NPD8451	Approved
0.6048	Remote Similarity	NPD6616	Approved
0.6033	Remote Similarity	NPD6054	Approved
0.6016	Remote Similarity	NPD7830	Approved
0.6016	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD7328	Approved
0.6	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD7078	Approved
0.5984	Remote Similarity	NPD6015	Approved
0.5984	Remote Similarity	NPD8033	Approved
0.5984	Remote Similarity	NPD6016	Approved
0.598	Remote Similarity	NPD1694	Approved
0.5965	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5368	Approved
0.5952	Remote Similarity	NPD7736	Approved
0.595	Remote Similarity	NPD7516	Approved
0.5935	Remote Similarity	NPD6370	Approved
0.5935	Remote Similarity	NPD5988	Approved
0.5932	Remote Similarity	NPD4632	Approved
0.5922	Remote Similarity	NPD5786	Approved
0.5918	Remote Similarity	NPD4271	Approved
0.5918	Remote Similarity	NPD4268	Approved
0.5917	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6009	Approved
0.5905	Remote Similarity	NPD6101	Approved
0.5905	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD8377	Approved
0.5902	Remote Similarity	NPD6059	Approved
0.5902	Remote Similarity	NPD8294	Approved
0.5902	Remote Similarity	NPD6319	Approved
0.5889	Remote Similarity	NPD7909	Approved
0.5888	Remote Similarity	NPD6399	Phase 3
0.5882	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6008	Approved
0.5873	Remote Similarity	NPD8293	Discontinued
0.5859	Remote Similarity	NPD8390	Approved
0.5859	Remote Similarity	NPD8392	Approved
0.5859	Remote Similarity	NPD8391	Approved
0.5854	Remote Similarity	NPD8378	Approved
0.5854	Remote Similarity	NPD7503	Approved
0.5854	Remote Similarity	NPD8380	Approved
0.5854	Remote Similarity	NPD8379	Approved
0.5854	Remote Similarity	NPD8296	Approved
0.5854	Remote Similarity	NPD8444	Approved
0.5854	Remote Similarity	NPD8335	Approved
0.584	Remote Similarity	NPD8341	Approved
0.584	Remote Similarity	NPD8340	Approved
0.584	Remote Similarity	NPD8299	Approved
0.584	Remote Similarity	NPD8342	Approved
0.5806	Remote Similarity	NPD8080	Discontinued
0.58	Remote Similarity	NPD4252	Approved
0.5794	Remote Similarity	NPD8273	Phase 1
0.5794	Remote Similarity	NPD6411	Approved
0.5794	Remote Similarity	NPD8035	Phase 2
0.5794	Remote Similarity	NPD8034	Phase 2
0.5785	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5331	Approved
0.5784	Remote Similarity	NPD5332	Approved
0.5765	Remote Similarity	NPD3730	Approved
0.5765	Remote Similarity	NPD3728	Approved
0.5763	Remote Similarity	NPD2204	Approved
0.576	Remote Similarity	NPD8328	Phase 3
0.5758	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD4238	Approved
0.5758	Remote Similarity	NPD4802	Phase 2
0.5743	Remote Similarity	NPD4790	Discontinued
0.573	Remote Similarity	NPD1145	Discontinued
0.5726	Remote Similarity	NPD6921	Approved
0.5726	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7524	Approved
0.5714	Remote Similarity	NPD6882	Approved
0.5714	Remote Similarity	NPD8297	Approved
0.569	Remote Similarity	NPD5697	Approved
0.5684	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6083	Phase 2
0.5676	Remote Similarity	NPD6084	Phase 2
0.5656	Remote Similarity	NPD7500	Approved
0.5652	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD6845	Suspended
0.5648	Remote Similarity	NPD7637	Suspended
0.5641	Remote Similarity	NPD6899	Approved
0.5641	Remote Similarity	NPD6881	Approved
0.5641	Remote Similarity	NPD7320	Approved
0.5636	Remote Similarity	NPD5695	Phase 3
0.5632	Remote Similarity	NPD2267	Suspended
0.5631	Remote Similarity	NPD6110	Phase 1
0.563	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6650	Approved
0.563	Remote Similarity	NPD6649	Approved
0.5625	Remote Similarity	NPD5696	Approved
0.5615	Remote Similarity	NPD5956	Approved
0.5614	Remote Similarity	NPD8138	Approved
0.5614	Remote Similarity	NPD8084	Approved
0.5614	Remote Similarity	NPD8083	Approved
0.5614	Remote Similarity	NPD8085	Approved
0.5614	Remote Similarity	NPD8139	Approved
0.5614	Remote Similarity	NPD8082	Approved
0.5614	Remote Similarity	NPD7632	Discontinued
0.5614	Remote Similarity	NPD8086	Approved
0.5603	Remote Similarity	NPD5739	Approved
0.5603	Remote Similarity	NPD6402	Approved
0.5603	Remote Similarity	NPD7128	Approved
0.5603	Remote Similarity	NPD6675	Approved
0.56	Remote Similarity	NPD5983	Phase 2

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