NPASS Compound

Structure

CID303451 OpenBabel06191716112D 29 30 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 -1.7321 0.0000 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 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 -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 -0.8660 -1.5000 0.0000 C 0 0 2 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 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 1 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 -0.5000 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 -1.7321 -2.0000 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 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 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 25 1 0 0 0 0 3 26 1 0 0 0 0 4 8 2 0 0 0 0 5 12 1 0 0 0 0 6 19 1 0 0 0 0 7 10 2 0 0 0 0 7 27 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 5 1 6 0 0 0 9 10 1 0 0 0 0 10 16 1 0 0 0 0 11 6 1 1 0 0 0 11 13 1 0 0 0 0 11 28 1 0 0 0 0 12 20 2 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 6 0 0 0 14 15 1 0 0 0 0 14 22 1 1 0 0 0 15 18 1 0 0 0 0 15 23 1 6 0 0 0 16 24 2 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 17 29 1 1 0 0 0 18 28 1 0 0 0 0 18 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.15
Volume:	388.918
LogP:	-0.049
LogD:	-0.123
LogS:	-0.939
# Rotatable Bonds:	8
TPSA:	161.21
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	4.612
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.464
MDCK Permeability:	0.00012815537047572434
Pgp-inhibitor:	0.005
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.803
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.319
Plasma Protein Binding (PPB):	25.0942325592041%
Volume Distribution (VD):	0.39
Pgp-substrate:	62.424957275390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.482
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	2.461
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.322
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.958
Rat Oral Acute Toxicity:	0.63
Maximum Recommended Daily Dose:	0.174
Skin Sensitization:	0.456
Carcinogencity:	0.921
Eye Corrosion:	0.004
Eye Irritation:	0.026
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: NPC303451

Natural Product ID:	NPC303451
*Common Name:**	Oleoside Dimethyl Ester
IUPAC Name:	methyl (4S,5Z,6S)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms:	Oleoside Dimethyl Ester
Standard InCHIKey:	KYVUMEGNMQDSHO-ISEXSMSQSA-N
Standard InCHI:	InChI=1S/C18H26O11/c1-4-8-9(5-12(20)25-2)10(16(24)26-3)7-27-17(8)29-18-15(23)14(22)13(21)11(6-19)28-18/h4,7,9,11,13-15,17-19,21-23H,5-6H2,1-3H3/b8-4-/t9-,11+,13+,14-,15+,17-,18-/m0/s1
SMILES:	COC(=O)C[C@H]1/C(=C/C)/[C@@H](OC=C1C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087778
PubChem CID:	14038300
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
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11411539]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787443]
NPO19884	Fraxinus excelsior	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20000781]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18340	Ligustrum lucidum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19884	Fraxinus excelsior	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18340	Ligustrum lucidum	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	4

Activity Type	# Activity
Cell Line	3
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	78.2	%	PMID[451884]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	-7.3	%	PMID[451884]
NPT520	Cell Line	3T3-L1	Mus musculus	Inhibition	=	-81.0	%	PMID[451884]
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	Activity	=	27.9	%	PMID[451884]

☑ 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 NPC303451 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	192
0.1-0.2	1525
0.2-0.3	5295
0.3-0.4	11383
0.4-0.5	13584
0.5-0.6	7774
0.6-0.7	2581
0.7-0.8	300
0.8-0.85	31
0.85-0.9	18
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC6414
0.9545	High Similarity	NPC469543
0.9318	High Similarity	NPC61201
0.9091	High Similarity	NPC117596
0.8925	High Similarity	NPC306344
0.8925	High Similarity	NPC255677
0.8925	High Similarity	NPC22149
0.8901	High Similarity	NPC170204
0.883	High Similarity	NPC298255
0.883	High Similarity	NPC28304
0.8778	High Similarity	NPC472125
0.8778	High Similarity	NPC472124
0.8778	High Similarity	NPC472126
0.8737	High Similarity	NPC310804
0.8737	High Similarity	NPC195510
0.8737	High Similarity	NPC261117
0.8737	High Similarity	NPC222062
0.8737	High Similarity	NPC13171
0.8667	High Similarity	NPC307699
0.8667	High Similarity	NPC470573
0.8667	High Similarity	NPC216826
0.8667	High Similarity	NPC120021
0.8667	High Similarity	NPC231710
0.8667	High Similarity	NPC270908
0.8667	High Similarity	NPC65665
0.8646	High Similarity	NPC267869
0.8646	High Similarity	NPC197541
0.8646	High Similarity	NPC234304
0.8646	High Similarity	NPC284929
0.8646	High Similarity	NPC118761
0.8602	High Similarity	NPC241911
0.8557	High Similarity	NPC86095
0.8542	High Similarity	NPC250545
0.8523	High Similarity	NPC470124
0.8409	Intermediate Similarity	NPC266718
0.8384	Intermediate Similarity	NPC254538
0.8384	Intermediate Similarity	NPC474285
0.8298	Intermediate Similarity	NPC101051
0.828	Intermediate Similarity	NPC320552
0.8261	Intermediate Similarity	NPC327253
0.8211	Intermediate Similarity	NPC306041
0.8202	Intermediate Similarity	NPC475035
0.8191	Intermediate Similarity	NPC294293
0.8172	Intermediate Similarity	NPC9447
0.8172	Intermediate Similarity	NPC477749
0.8161	Intermediate Similarity	NPC127295
0.8161	Intermediate Similarity	NPC163362
0.8132	Intermediate Similarity	NPC475037
0.8085	Intermediate Similarity	NPC472195
0.8085	Intermediate Similarity	NPC472196
0.8085	Intermediate Similarity	NPC238090
0.8043	Intermediate Similarity	NPC137368
0.8	Intermediate Similarity	NPC159698
0.7957	Intermediate Similarity	NPC477748
0.7935	Intermediate Similarity	NPC475186
0.7935	Intermediate Similarity	NPC118077
0.7912	Intermediate Similarity	NPC475034
0.79	Intermediate Similarity	NPC27687
0.7895	Intermediate Similarity	NPC320089
0.7872	Intermediate Similarity	NPC202886
0.7865	Intermediate Similarity	NPC469469
0.7835	Intermediate Similarity	NPC54731
0.7812	Intermediate Similarity	NPC25701
0.7812	Intermediate Similarity	NPC2003
0.78	Intermediate Similarity	NPC177013
0.78	Intermediate Similarity	NPC4899
0.78	Intermediate Similarity	NPC201191
0.78	Intermediate Similarity	NPC471599
0.78	Intermediate Similarity	NPC35185
0.78	Intermediate Similarity	NPC474730
0.78	Intermediate Similarity	NPC106668
0.7789	Intermediate Similarity	NPC472197
0.7789	Intermediate Similarity	NPC472199
0.7778	Intermediate Similarity	NPC244878
0.7778	Intermediate Similarity	NPC251026
0.7766	Intermediate Similarity	NPC285588
0.7755	Intermediate Similarity	NPC472290
0.7723	Intermediate Similarity	NPC37240
0.7723	Intermediate Similarity	NPC475928
0.7723	Intermediate Similarity	NPC197736
0.7717	Intermediate Similarity	NPC477746
0.7717	Intermediate Similarity	NPC477747
0.77	Intermediate Similarity	NPC219038
0.77	Intermediate Similarity	NPC20673
0.7692	Intermediate Similarity	NPC473315
0.7692	Intermediate Similarity	NPC142111
0.7684	Intermediate Similarity	NPC473311
0.7684	Intermediate Similarity	NPC118078
0.7677	Intermediate Similarity	NPC40182
0.7677	Intermediate Similarity	NPC151093
0.7677	Intermediate Similarity	NPC198422
0.7677	Intermediate Similarity	NPC472015
0.766	Intermediate Similarity	NPC470137
0.7653	Intermediate Similarity	NPC161293
0.764	Intermediate Similarity	NPC321728
0.7629	Intermediate Similarity	NPC256368
0.7629	Intermediate Similarity	NPC71589
0.7629	Intermediate Similarity	NPC472198
0.7614	Intermediate Similarity	NPC110813
0.7609	Intermediate Similarity	NPC473308
0.7604	Intermediate Similarity	NPC110072
0.7596	Intermediate Similarity	NPC472507
0.7596	Intermediate Similarity	NPC392
0.7596	Intermediate Similarity	NPC219900
0.7596	Intermediate Similarity	NPC177524
0.7573	Intermediate Similarity	NPC170432
0.7573	Intermediate Similarity	NPC41681
0.7553	Intermediate Similarity	NPC142583
0.7528	Intermediate Similarity	NPC133377
0.7525	Intermediate Similarity	NPC287539
0.7525	Intermediate Similarity	NPC3488
0.7525	Intermediate Similarity	NPC4637
0.7525	Intermediate Similarity	NPC198992
0.7525	Intermediate Similarity	NPC98859
0.75	Intermediate Similarity	NPC229655
0.75	Intermediate Similarity	NPC61630
0.75	Intermediate Similarity	NPC307517
0.75	Intermediate Similarity	NPC326661
0.75	Intermediate Similarity	NPC148270
0.75	Intermediate Similarity	NPC81483
0.75	Intermediate Similarity	NPC169468
0.75	Intermediate Similarity	NPC197813
0.75	Intermediate Similarity	NPC80338
0.7475	Intermediate Similarity	NPC143446
0.7453	Intermediate Similarity	NPC472508
0.7449	Intermediate Similarity	NPC477345
0.7449	Intermediate Similarity	NPC477348
0.7449	Intermediate Similarity	NPC238264
0.7449	Intermediate Similarity	NPC63897
0.7447	Intermediate Similarity	NPC47220
0.7447	Intermediate Similarity	NPC208473
0.7447	Intermediate Similarity	NPC186332
0.7444	Intermediate Similarity	NPC323472
0.7429	Intermediate Similarity	NPC473807
0.7423	Intermediate Similarity	NPC470373
0.7423	Intermediate Similarity	NPC470379
0.7419	Intermediate Similarity	NPC288471
0.7419	Intermediate Similarity	NPC136699
0.7419	Intermediate Similarity	NPC220167
0.7379	Intermediate Similarity	NPC151516
0.7368	Intermediate Similarity	NPC74139
0.7358	Intermediate Similarity	NPC133625
0.7353	Intermediate Similarity	NPC2313
0.7353	Intermediate Similarity	NPC154132
0.7353	Intermediate Similarity	NPC475157
0.7353	Intermediate Similarity	NPC471637
0.7353	Intermediate Similarity	NPC475655
0.7353	Intermediate Similarity	NPC57586
0.7347	Intermediate Similarity	NPC280390
0.7333	Intermediate Similarity	NPC477314
0.7327	Intermediate Similarity	NPC473307
0.732	Intermediate Similarity	NPC177668
0.732	Intermediate Similarity	NPC473619
0.7312	Intermediate Similarity	NPC38295
0.7312	Intermediate Similarity	NPC188717
0.7312	Intermediate Similarity	NPC473500
0.7312	Intermediate Similarity	NPC44261
0.7312	Intermediate Similarity	NPC156089
0.7312	Intermediate Similarity	NPC211455
0.7312	Intermediate Similarity	NPC470313
0.7308	Intermediate Similarity	NPC469869
0.73	Intermediate Similarity	NPC288350
0.73	Intermediate Similarity	NPC475241
0.73	Intermediate Similarity	NPC475593
0.73	Intermediate Similarity	NPC475540
0.73	Intermediate Similarity	NPC475525
0.73	Intermediate Similarity	NPC476066
0.73	Intermediate Similarity	NPC475164
0.73	Intermediate Similarity	NPC256230
0.73	Intermediate Similarity	NPC473765
0.73	Intermediate Similarity	NPC475375
0.73	Intermediate Similarity	NPC473605
0.73	Intermediate Similarity	NPC173329
0.7292	Intermediate Similarity	NPC248312
0.7292	Intermediate Similarity	NPC471755
0.7292	Intermediate Similarity	NPC471756
0.7292	Intermediate Similarity	NPC473151
0.729	Intermediate Similarity	NPC193741
0.729	Intermediate Similarity	NPC83005
0.7283	Intermediate Similarity	NPC21693
0.7283	Intermediate Similarity	NPC280367
0.7283	Intermediate Similarity	NPC236649
0.7282	Intermediate Similarity	NPC121423
0.7273	Intermediate Similarity	NPC475832
0.7273	Intermediate Similarity	NPC475927
0.7264	Intermediate Similarity	NPC110701
0.7253	Intermediate Similarity	NPC179933
0.7245	Intermediate Similarity	NPC477349
0.7245	Intermediate Similarity	NPC473321
0.7245	Intermediate Similarity	NPC472010
0.7238	Intermediate Similarity	NPC476738
0.7238	Intermediate Similarity	NPC127235
0.7238	Intermediate Similarity	NPC239961
0.7238	Intermediate Similarity	NPC476740
0.7238	Intermediate Similarity	NPC82251
0.7234	Intermediate Similarity	NPC70424
0.7234	Intermediate Similarity	NPC243618
0.7228	Intermediate Similarity	NPC474194
0.7228	Intermediate Similarity	NPC153559
0.7228	Intermediate Similarity	NPC476613

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 NPC303451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1951
0.2-0.3	3971
0.3-0.4	2075
0.4-0.5	743
0.5-0.6	212
0.6-0.7	34
0.7-0.8	3
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
0.7596	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.7327	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7838	Discovery
0.6909	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8513	Phase 3
0.681	Remote Similarity	NPD7503	Approved
0.6771	Remote Similarity	NPD6110	Phase 1
0.6733	Remote Similarity	NPD7983	Approved
0.6695	Remote Similarity	NPD7830	Approved
0.6695	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6583	Remote Similarity	NPD7507	Approved
0.6531	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8444	Approved
0.6423	Remote Similarity	NPD7319	Approved
0.6417	Remote Similarity	NPD7642	Approved
0.641	Remote Similarity	NPD7328	Approved
0.641	Remote Similarity	NPD7641	Discontinued
0.641	Remote Similarity	NPD7327	Approved
0.64	Remote Similarity	NPD4249	Approved
0.6396	Remote Similarity	NPD6412	Phase 2
0.6356	Remote Similarity	NPD7516	Approved
0.6337	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD4251	Approved
0.6321	Remote Similarity	NPD7839	Suspended
0.6311	Remote Similarity	NPD8451	Approved
0.6303	Remote Similarity	NPD8294	Approved
0.6303	Remote Similarity	NPD8377	Approved
0.6273	Remote Similarity	NPD1407	Approved
0.6261	Remote Similarity	NPD6053	Discontinued
0.626	Remote Similarity	NPD8448	Approved
0.625	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD8296	Approved
0.625	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD8335	Approved
0.625	Remote Similarity	NPD8379	Approved
0.6239	Remote Similarity	NPD5344	Discontinued
0.6207	Remote Similarity	NPD8133	Approved
0.6204	Remote Similarity	NPD4225	Approved
0.6186	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8328	Phase 3
0.614	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8074	Phase 3
0.6111	Remote Similarity	NPD8392	Approved
0.6111	Remote Similarity	NPD8390	Approved
0.6111	Remote Similarity	NPD8391	Approved
0.61	Remote Similarity	NPD7154	Phase 3
0.6098	Remote Similarity	NPD8342	Approved
0.6098	Remote Similarity	NPD8340	Approved
0.6098	Remote Similarity	NPD8341	Approved
0.6098	Remote Similarity	NPD8299	Approved
0.6087	Remote Similarity	NPD6371	Approved
0.6077	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD8080	Discontinued
0.6055	Remote Similarity	NPD7638	Approved
0.6044	Remote Similarity	NPD898	Approved
0.6044	Remote Similarity	NPD897	Approved
0.6044	Remote Similarity	NPD896	Approved
0.6038	Remote Similarity	NPD5778	Approved
0.6038	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD7639	Approved
0.5984	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7329	Approved
0.5856	Remote Similarity	NPD6648	Approved
0.5849	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7637	Suspended
0.578	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD2204	Approved
0.5758	Remote Similarity	NPD4271	Approved
0.5758	Remote Similarity	NPD4268	Approved
0.5755	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6101	Approved
0.5729	Remote Similarity	NPD3181	Approved
0.5703	Remote Similarity	NPD7736	Approved
0.5692	Remote Similarity	NPD7260	Phase 2
0.5688	Remote Similarity	NPD5282	Discontinued
0.5686	Remote Similarity	NPD6435	Approved
0.5686	Remote Similarity	NPD5209	Approved
0.5686	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.568	Remote Similarity	NPD6370	Approved
0.5678	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6421	Discontinued
0.5657	Remote Similarity	NPD4756	Discovery
0.5656	Remote Similarity	NPD7115	Discovery
0.5656	Remote Similarity	NPD6009	Approved
0.5652	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6411	Approved
0.5647	Remote Similarity	NPD892	Phase 3
0.5647	Remote Similarity	NPD891	Phase 3
0.5647	Remote Similarity	NPD893	Approved
0.5647	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD888	Phase 3
0.5645	Remote Similarity	NPD6319	Approved
0.5644	Remote Similarity	NPD4822	Approved
0.5644	Remote Similarity	NPD4820	Approved
0.5644	Remote Similarity	NPD4821	Approved
0.5644	Remote Similarity	NPD4819	Approved
0.5641	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8293	Discontinued
0.5607	Remote Similarity	NPD1695	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