NPASS Compound

Structure

NPC469543 OpenBabel07101718222D 40 42 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 2 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 9 2 0 0 0 0 5 14 1 0 0 0 0 6 25 1 0 0 0 0 7 11 2 0 0 0 0 7 36 1 0 0 0 0 8 37 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 5 1 1 0 0 0 10 11 1 0 0 0 0 11 21 1 0 0 0 0 12 6 1 6 0 0 0 12 15 1 0 0 0 0 12 38 1 0 0 0 0 13 8 1 6 0 0 0 13 16 1 0 0 0 0 13 39 1 0 0 0 0 14 26 2 0 0 0 0 14 34 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 1 0 0 0 16 18 1 0 0 0 0 16 28 1 1 0 0 0 17 19 1 0 0 0 0 17 29 1 6 0 0 0 18 20 1 0 0 0 0 18 30 1 6 0 0 0 19 23 1 0 0 0 0 19 31 1 1 0 0 0 20 24 1 0 0 0 0 20 32 1 1 0 0 0 21 33 2 0 0 0 0 21 35 1 0 0 0 0 22 36 1 0 0 0 0 22 40 1 0 0 0 0 23 37 1 6 0 0 0 23 38 1 0 0 0 0 24 39 1 0 0 0 0 24 40 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.2
Volume:	528.089
LogP:	-0.783
LogD:	-0.852
LogS:	-1.031
# Rotatable Bonds:	11
TPSA:	240.36
# H-Bond Aceptor:	16
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.102
Synthetic Accessibility Score:	5.166
Fsp3:	0.75
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.321
MDCK Permeability:	0.0003351737395860255
Pgp-inhibitor:	0.003
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.983
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.25
Plasma Protein Binding (PPB):	32.37324905395508%
Volume Distribution (VD):	0.351
Pgp-substrate:	43.97391891479492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	1.057
Half-life (T1/2):	0.854

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.743
Rat Oral Acute Toxicity:	0.323
Maximum Recommended Daily Dose:	0.122
Skin Sensitization:	0.118
Carcinogencity:	0.79
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.733

Download Data

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

Natural Product: NPC469543

Natural Product ID:	NPC469543
*Common Name:**	Excelside A
IUPAC Name:	methyl (4S,5E)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms:
Standard InCHIKey:	KIYJRYWOZVDCRC-GLYOJDOWSA-N
Standard InCHI:	InChI=1S/C24H36O16/c1-4-9-10(5-14(26)34-2)11(21(33)35-3)7-36-22(9)40-24-20(32)18(30)16(28)13(39-24)8-37-23-19(31)17(29)15(27)12(6-25)38-23/h4,7,10,12-13,15-20,22-25,27-32H,5-6,8H2,1-3H3/b9-4+/t10-,12+,13+,15+,16+,17-,18-,19+,20+,22?,23+,24-/m0/s1
SMILES:	CC=C1C(C(=COC1OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O)C(=O)OC)CC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086876
PubChem CID:	46881041
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO19884	Fraxinus excelsior	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20000781]
NPO19884	Fraxinus excelsior	Species	Oleaceae	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
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	102.5	%	PMID[550457]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	30.9	%	PMID[550457]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	-16.6	%	PMID[550457]

☑ 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 NPC469543 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	206
0.1-0.2	1575
0.2-0.3	5209
0.3-0.4	11427
0.4-0.5	12998
0.5-0.6	8146
0.6-0.7	2797
0.7-0.8	275
0.8-0.85	31
0.85-0.9	22
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC6414
0.9545	High Similarity	NPC303451
0.8958	High Similarity	NPC222062
0.8913	High Similarity	NPC61201
0.8866	High Similarity	NPC197541
0.8866	High Similarity	NPC267869
0.8866	High Similarity	NPC234304
0.8866	High Similarity	NPC284929
0.8866	High Similarity	NPC118761
0.8804	High Similarity	NPC472124
0.8804	High Similarity	NPC472126
0.8804	High Similarity	NPC472125
0.8723	High Similarity	NPC170204
0.8696	High Similarity	NPC65665
0.8696	High Similarity	NPC270908
0.8696	High Similarity	NPC470573
0.8696	High Similarity	NPC216826
0.8696	High Similarity	NPC120021
0.8696	High Similarity	NPC231710
0.8696	High Similarity	NPC117596
0.8696	High Similarity	NPC307699
0.8557	High Similarity	NPC255677
0.8557	High Similarity	NPC306344
0.8557	High Similarity	NPC22149
0.8469	Intermediate Similarity	NPC28304
0.8469	Intermediate Similarity	NPC298255
0.8421	Intermediate Similarity	NPC294293
0.84	Intermediate Similarity	NPC86095
0.8384	Intermediate Similarity	NPC13171
0.8384	Intermediate Similarity	NPC195510
0.8384	Intermediate Similarity	NPC261117
0.8384	Intermediate Similarity	NPC310804
0.8333	Intermediate Similarity	NPC101051
0.8247	Intermediate Similarity	NPC241911
0.8242	Intermediate Similarity	NPC266718
0.8202	Intermediate Similarity	NPC127295
0.8202	Intermediate Similarity	NPC163362
0.82	Intermediate Similarity	NPC250545
0.8191	Intermediate Similarity	NPC285588
0.8152	Intermediate Similarity	NPC470124
0.8125	Intermediate Similarity	NPC320552
0.8119	Intermediate Similarity	NPC197736
0.8105	Intermediate Similarity	NPC327253
0.8058	Intermediate Similarity	NPC254538
0.8058	Intermediate Similarity	NPC474285
0.8041	Intermediate Similarity	NPC159698
0.8021	Intermediate Similarity	NPC110072
0.8021	Intermediate Similarity	NPC477749
0.7979	Intermediate Similarity	NPC118077
0.7979	Intermediate Similarity	NPC475186
0.7938	Intermediate Similarity	NPC472196
0.7938	Intermediate Similarity	NPC472195
0.7938	Intermediate Similarity	NPC238090
0.7938	Intermediate Similarity	NPC320089
0.79	Intermediate Similarity	NPC198422
0.79	Intermediate Similarity	NPC40182
0.7879	Intermediate Similarity	NPC306041
0.7857	Intermediate Similarity	NPC477345
0.7857	Intermediate Similarity	NPC238264
0.7857	Intermediate Similarity	NPC477348
0.7849	Intermediate Similarity	NPC475035
0.7843	Intermediate Similarity	NPC201191
0.7835	Intermediate Similarity	NPC9447
0.7812	Intermediate Similarity	NPC477748
0.7789	Intermediate Similarity	NPC475037
0.7745	Intermediate Similarity	NPC154132
0.7745	Intermediate Similarity	NPC2313
0.7745	Intermediate Similarity	NPC475157
0.7745	Intermediate Similarity	NPC475655
0.7745	Intermediate Similarity	NPC57586
0.7745	Intermediate Similarity	NPC471637
0.7732	Intermediate Similarity	NPC202886
0.7717	Intermediate Similarity	NPC469469
0.7708	Intermediate Similarity	NPC137368
0.77	Intermediate Similarity	NPC475164
0.77	Intermediate Similarity	NPC475593
0.77	Intermediate Similarity	NPC475241
0.77	Intermediate Similarity	NPC473605
0.77	Intermediate Similarity	NPC476066
0.77	Intermediate Similarity	NPC475375
0.77	Intermediate Similarity	NPC54731
0.77	Intermediate Similarity	NPC475540
0.77	Intermediate Similarity	NPC475525
0.77	Intermediate Similarity	NPC473765
0.77	Intermediate Similarity	NPC143446
0.7677	Intermediate Similarity	NPC472198
0.767	Intermediate Similarity	NPC471599
0.7653	Intermediate Similarity	NPC472197
0.7653	Intermediate Similarity	NPC477349
0.7653	Intermediate Similarity	NPC472199
0.7647	Intermediate Similarity	NPC244878
0.7642	Intermediate Similarity	NPC177524
0.7642	Intermediate Similarity	NPC219900
0.7642	Intermediate Similarity	NPC473807
0.7642	Intermediate Similarity	NPC392
0.7634	Intermediate Similarity	NPC251026
0.7619	Intermediate Similarity	NPC476740
0.7619	Intermediate Similarity	NPC476738
0.7596	Intermediate Similarity	NPC27687
0.7579	Intermediate Similarity	NPC477747
0.7579	Intermediate Similarity	NPC477746
0.7579	Intermediate Similarity	NPC475034
0.7576	Intermediate Similarity	NPC280390
0.7573	Intermediate Similarity	NPC20673
0.7573	Intermediate Similarity	NPC219038
0.7553	Intermediate Similarity	NPC473315
0.7553	Intermediate Similarity	NPC142111
0.7551	Intermediate Similarity	NPC473311
0.7551	Intermediate Similarity	NPC118078
0.7549	Intermediate Similarity	NPC151093
0.7526	Intermediate Similarity	NPC470137
0.7526	Intermediate Similarity	NPC248312
0.75	Intermediate Similarity	NPC177013
0.75	Intermediate Similarity	NPC44682
0.75	Intermediate Similarity	NPC71589
0.75	Intermediate Similarity	NPC4899
0.75	Intermediate Similarity	NPC323472
0.75	Intermediate Similarity	NPC25701
0.75	Intermediate Similarity	NPC256368
0.75	Intermediate Similarity	NPC321728
0.75	Intermediate Similarity	NPC163409
0.75	Intermediate Similarity	NPC2003
0.75	Intermediate Similarity	NPC35185
0.75	Intermediate Similarity	NPC474730
0.75	Intermediate Similarity	NPC106668
0.7477	Intermediate Similarity	NPC193765
0.7477	Intermediate Similarity	NPC472507
0.7474	Intermediate Similarity	NPC473308
0.7473	Intermediate Similarity	NPC110813
0.7453	Intermediate Similarity	NPC41681
0.7453	Intermediate Similarity	NPC315070
0.7451	Intermediate Similarity	NPC475332
0.7451	Intermediate Similarity	NPC472290
0.7429	Intermediate Similarity	NPC473816
0.7429	Intermediate Similarity	NPC474581
0.7429	Intermediate Similarity	NPC309398
0.7429	Intermediate Similarity	NPC475367
0.7429	Intermediate Similarity	NPC475928
0.7429	Intermediate Similarity	NPC37240
0.7423	Intermediate Similarity	NPC125142
0.7407	Intermediate Similarity	NPC133625
0.7404	Intermediate Similarity	NPC476611
0.7404	Intermediate Similarity	NPC4637
0.7404	Intermediate Similarity	NPC98859
0.7391	Intermediate Similarity	NPC133377
0.7379	Intermediate Similarity	NPC472015
0.7368	Intermediate Similarity	NPC156089
0.7368	Intermediate Similarity	NPC473500
0.7368	Intermediate Similarity	NPC38295
0.7368	Intermediate Similarity	NPC470313
0.7358	Intermediate Similarity	NPC469869
0.7353	Intermediate Similarity	NPC161293
0.7339	Intermediate Similarity	NPC472508
0.7339	Intermediate Similarity	NPC83005
0.732	Intermediate Similarity	NPC47220
0.732	Intermediate Similarity	NPC186332
0.732	Intermediate Similarity	NPC208473
0.73	Intermediate Similarity	NPC472010
0.73	Intermediate Similarity	NPC470379
0.73	Intermediate Similarity	NPC470373
0.7292	Intermediate Similarity	NPC288471
0.729	Intermediate Similarity	NPC170432
0.7282	Intermediate Similarity	NPC278506
0.7263	Intermediate Similarity	NPC20072
0.7257	Intermediate Similarity	NPC474483
0.7248	Intermediate Similarity	NPC313668
0.7248	Intermediate Similarity	NPC315836
0.7245	Intermediate Similarity	NPC142583
0.7238	Intermediate Similarity	NPC3488
0.7238	Intermediate Similarity	NPC198992
0.7238	Intermediate Similarity	NPC287539
0.7228	Intermediate Similarity	NPC159092
0.7222	Intermediate Similarity	NPC80338
0.7222	Intermediate Similarity	NPC197813
0.7222	Intermediate Similarity	NPC148270
0.7212	Intermediate Similarity	NPC307517
0.7212	Intermediate Similarity	NPC255592
0.7212	Intermediate Similarity	NPC56071
0.7212	Intermediate Similarity	NPC308567
0.7212	Intermediate Similarity	NPC169468
0.7212	Intermediate Similarity	NPC261377
0.7212	Intermediate Similarity	NPC70733
0.7212	Intermediate Similarity	NPC187761
0.7212	Intermediate Similarity	NPC81483
0.7212	Intermediate Similarity	NPC83895
0.7212	Intermediate Similarity	NPC61630
0.7204	Intermediate Similarity	NPC477314
0.72	Intermediate Similarity	NPC177668
0.7193	Intermediate Similarity	NPC475309
0.7193	Intermediate Similarity	NPC13710
0.7184	Intermediate Similarity	NPC288350
0.7184	Intermediate Similarity	NPC256230
0.7184	Intermediate Similarity	NPC255410
0.7184	Intermediate Similarity	NPC173329
0.7174	Intermediate Similarity	NPC326661
0.7174	Intermediate Similarity	NPC229655
0.717	Intermediate Similarity	NPC121423
0.717	Intermediate Similarity	NPC313569
0.7158	Intermediate Similarity	NPC21693
0.7158	Intermediate Similarity	NPC236649

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 NPC469543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1820
0.2-0.3	4099
0.3-0.4	2081
0.4-0.5	682
0.5-0.6	244
0.6-0.7	50
0.7-0.8	4
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
0.7642	Intermediate Similarity	NPD6686	Approved
0.7379	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6698	Approved
0.7374	Intermediate Similarity	NPD46	Approved
0.7117	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8513	Phase 3
0.6864	Remote Similarity	NPD8517	Approved
0.6864	Remote Similarity	NPD8515	Approved
0.6864	Remote Similarity	NPD7503	Approved
0.6864	Remote Similarity	NPD8516	Approved
0.6863	Remote Similarity	NPD7838	Discovery
0.675	Remote Similarity	NPD7830	Approved
0.675	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6639	Remote Similarity	NPD7507	Approved
0.6635	Remote Similarity	NPD7983	Approved
0.6583	Remote Similarity	NPD8444	Approved
0.6552	Remote Similarity	NPD8133	Approved
0.65	Remote Similarity	NPD8294	Approved
0.65	Remote Similarity	NPD8377	Approved
0.648	Remote Similarity	NPD7319	Approved
0.6475	Remote Similarity	NPD8328	Phase 3
0.6471	Remote Similarity	NPD7328	Approved
0.6471	Remote Similarity	NPD7327	Approved
0.646	Remote Similarity	NPD6412	Phase 2
0.6452	Remote Similarity	NPD8448	Approved
0.6446	Remote Similarity	NPD8378	Approved
0.6446	Remote Similarity	NPD8380	Approved
0.6446	Remote Similarity	NPD8379	Approved
0.6446	Remote Similarity	NPD8296	Approved
0.6446	Remote Similarity	NPD8033	Approved
0.6446	Remote Similarity	NPD8335	Approved
0.6436	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7516	Approved
0.6371	Remote Similarity	NPD8451	Approved
0.6341	Remote Similarity	NPD7642	Approved
0.6333	Remote Similarity	NPD7641	Discontinued
0.6325	Remote Similarity	NPD6053	Discontinued
0.632	Remote Similarity	NPD8074	Phase 3
0.6299	Remote Similarity	NPD8390	Approved
0.6299	Remote Similarity	NPD8391	Approved
0.6299	Remote Similarity	NPD8392	Approved
0.6263	Remote Similarity	NPD7329	Approved
0.625	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7839	Suspended
0.6207	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5344	Discontinued
0.616	Remote Similarity	NPD8340	Approved
0.616	Remote Similarity	NPD8341	Approved
0.616	Remote Similarity	NPD8299	Approved
0.616	Remote Similarity	NPD8342	Approved
0.6154	Remote Similarity	NPD4249	Approved
0.6129	Remote Similarity	NPD8080	Discontinued
0.6126	Remote Similarity	NPD7638	Approved
0.6116	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7639	Approved
0.6071	Remote Similarity	NPD7640	Approved
0.6053	Remote Similarity	NPD1407	Approved
0.6048	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7154	Phase 3
0.6017	Remote Similarity	NPD6371	Approved
0.6015	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4225	Approved
0.5979	Remote Similarity	NPD3181	Approved
0.5963	Remote Similarity	NPD5778	Approved
0.5963	Remote Similarity	NPD5779	Approved
0.5905	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6101	Approved
0.5824	Remote Similarity	NPD6123	Approved
0.5821	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD896	Approved
0.5789	Remote Similarity	NPD897	Approved
0.5789	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD898	Approved
0.5789	Remote Similarity	NPD6648	Approved
0.578	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD8337	Approved
0.5769	Remote Similarity	NPD8336	Approved
0.5769	Remote Similarity	NPD7736	Approved
0.5758	Remote Similarity	NPD7260	Phase 2
0.5755	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD6370	Approved
0.5746	Remote Similarity	NPD8415	Approved
0.5727	Remote Similarity	NPD6411	Approved
0.5727	Remote Similarity	NPD7637	Suspended
0.5726	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD8293	Discontinued
0.5686	Remote Similarity	NPD4268	Approved
0.5686	Remote Similarity	NPD4271	Approved
0.5659	Remote Similarity	NPD7492	Approved
0.5656	Remote Similarity	NPD6430	Approved
0.5656	Remote Similarity	NPD6882	Approved
0.5656	Remote Similarity	NPD6429	Approved
0.5643	Remote Similarity	NPD7266	Discontinued
0.562	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.562	Remote Similarity	NPD6421	Discontinued
0.5619	Remote Similarity	NPD6435	Approved
0.5615	Remote Similarity	NPD6616	Approved
0.56	Remote Similarity	NPD6009	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