NPASS Compound

Structure

NPC469985 OpenBabel07101718322D 31 34 0 0 1 0 0 0 0 0999 V2000 2.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4258 3.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0772 2.0965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 -1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 -1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4257 3.6573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2038 2.5835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6182 -0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8653 -0.3880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6397 1.0707 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0108 0.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8868 1.0520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2471 -0.0187 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9386 4.5157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1888 3.5834 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8503 -1.3879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8477 1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9127 2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6547 2.0706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 6 7 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 11 22 1 0 0 0 0 11 30 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 25 2 0 0 0 0 13 30 1 0 0 0 0 14 26 2 0 0 0 0 14 31 1 0 0 0 0 15 6 1 6 0 0 0 16 23 1 1 0 0 0 16 24 1 0 0 0 0 17 23 1 1 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 18 31 1 6 0 0 0 19 22 1 1 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 20 28 1 0 0 0 0 21 24 1 0 0 0 0 21 29 2 0 0 0 0 22 4 1 6 0 0 0 23 5 1 1 0 0 0 24 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.23
Volume:	440.42
LogP:	1.828
LogD:	1.837
LogS:	-4.163
# Rotatable Bonds:	5
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	6.253
Fsp3:	0.792
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:	-5.241
MDCK Permeability:	0.00011122640717076138
Pgp-inhibitor:	0.027
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.865
20% Bioavailability (F20%):	0.184
30% Bioavailability (F30%):	0.514

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.433
Plasma Protein Binding (PPB):	50.78864669799805%
Volume Distribution (VD):	0.918
Pgp-substrate:	56.39092254638672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.541
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.416
CYP3A4-substrate:	0.334

ADMET: Excretion

Clearance (CL):	3.093
Half-life (T1/2):	0.605

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.286
Drug-inuced Liver Injury (DILI):	0.199
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.866
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.057
Carcinogencity:	0.541
Eye Corrosion:	0.005
Eye Irritation:	0.014
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC469985

Natural Product ID:	NPC469985
*Common Name:**	Maoesin E
IUPAC Name:	n.a.
Synonyms:	Maoesin E
Standard InCHIKey:	YLAQTEHVFWEICH-WPRZVXRGSA-N
Standard InCHI:	InChI=1S/C24H34O7/c1-12-15-6-7-16-23(5)17(27)8-9-22(4,11-30-13(2)25)19(23)18(31-14(3)26)21(29)24(16,10-15)20(12)28/h15-20,27-28H,1,6-11H2,2-5H3/t15-,16+,17+,18+,19-,20?,22+,23-,24+/m1/s1
SMILES:	CC(=O)OCC1(CCC(C2(C1C(C(=O)C34C2CCC(C3)C(=C)C4O)OC(=O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641894
PubChem CID:	53325782
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[568665]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[568665]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[568665]

☑ 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 NPC469985 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	223
0.1-0.2	1705
0.2-0.3	5650
0.3-0.4	10497
0.4-0.5	10537
0.5-0.6	5980
0.6-0.7	5554
0.7-0.8	2240
0.8-0.85	201
0.85-0.9	96
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC50535
0.9293	High Similarity	NPC47281
0.92	High Similarity	NPC37600
0.9184	High Similarity	NPC253886
0.9184	High Similarity	NPC121218
0.9109	High Similarity	NPC251824
0.9109	High Similarity	NPC86852
0.901	High Similarity	NPC295366
0.901	High Similarity	NPC28791
0.9	High Similarity	NPC266
0.898	High Similarity	NPC471038
0.8969	High Similarity	NPC329910
0.8942	High Similarity	NPC470281
0.8922	High Similarity	NPC176949
0.8922	High Similarity	NPC201908
0.89	High Similarity	NPC170615
0.8866	High Similarity	NPC470232
0.8866	High Similarity	NPC470229
0.8857	High Similarity	NPC40608
0.8835	High Similarity	NPC211224
0.8812	High Similarity	NPC87927
0.88	High Similarity	NPC39683
0.88	High Similarity	NPC163963
0.88	High Similarity	NPC289148
0.88	High Similarity	NPC46848
0.88	High Similarity	NPC295276
0.88	High Similarity	NPC52899
0.88	High Similarity	NPC75941
0.8788	High Similarity	NPC474793
0.8776	High Similarity	NPC200054
0.8776	High Similarity	NPC29410
0.8763	High Similarity	NPC470385
0.8763	High Similarity	NPC47853
0.8763	High Similarity	NPC475118
0.8763	High Similarity	NPC470386
0.875	High Similarity	NPC198054
0.8725	High Similarity	NPC29705
0.8713	High Similarity	NPC246736
0.8713	High Similarity	NPC148628
0.8713	High Similarity	NPC286519
0.8713	High Similarity	NPC304832
0.8713	High Similarity	NPC88203
0.8713	High Similarity	NPC76866
0.8713	High Similarity	NPC214946
0.8713	High Similarity	NPC275990
0.87	High Similarity	NPC108371
0.87	High Similarity	NPC180733
0.87	High Similarity	NPC37047
0.87	High Similarity	NPC287676
0.87	High Similarity	NPC41971
0.8673	High Similarity	NPC98639
0.8654	High Similarity	NPC94529
0.8646	High Similarity	NPC100313
0.8641	High Similarity	NPC285927
0.8641	High Similarity	NPC265127
0.8627	High Similarity	NPC122811
0.8627	High Similarity	NPC277074
0.8627	High Similarity	NPC209298
0.8614	High Similarity	NPC236585
0.86	High Similarity	NPC28864
0.86	High Similarity	NPC20479
0.86	High Similarity	NPC38296
0.86	High Similarity	NPC98837
0.86	High Similarity	NPC78427
0.86	High Similarity	NPC162459
0.86	High Similarity	NPC16911
0.86	High Similarity	NPC38471
0.8586	High Similarity	NPC234564
0.8586	High Similarity	NPC219353
0.8586	High Similarity	NPC470387
0.8585	High Similarity	NPC94650
0.8558	High Similarity	NPC471246
0.8557	High Similarity	NPC198242
0.8557	High Similarity	NPC211403
0.8557	High Similarity	NPC470230
0.8544	High Similarity	NPC310586
0.8544	High Similarity	NPC98603
0.8515	High Similarity	NPC293866
0.8515	High Similarity	NPC470388
0.8515	High Similarity	NPC94906
0.85	High Similarity	NPC253586
0.8485	Intermediate Similarity	NPC205173
0.8476	Intermediate Similarity	NPC112895
0.8476	Intermediate Similarity	NPC231278
0.8476	Intermediate Similarity	NPC218123
0.8469	Intermediate Similarity	NPC199543
0.8462	Intermediate Similarity	NPC200957
0.8462	Intermediate Similarity	NPC138908
0.8462	Intermediate Similarity	NPC278628
0.8462	Intermediate Similarity	NPC231530
0.8454	Intermediate Similarity	NPC53890
0.8454	Intermediate Similarity	NPC219937
0.8454	Intermediate Similarity	NPC123252
0.8454	Intermediate Similarity	NPC194485
0.8447	Intermediate Similarity	NPC139347
0.8447	Intermediate Similarity	NPC216114
0.8438	Intermediate Similarity	NPC160304
0.8431	Intermediate Similarity	NPC252614
0.8416	Intermediate Similarity	NPC472028
0.8416	Intermediate Similarity	NPC89099
0.84	Intermediate Similarity	NPC13949
0.8396	Intermediate Similarity	NPC471250
0.8384	Intermediate Similarity	NPC469982
0.8384	Intermediate Similarity	NPC280804
0.8381	Intermediate Similarity	NPC166993
0.8367	Intermediate Similarity	NPC250753
0.8365	Intermediate Similarity	NPC84928
0.8365	Intermediate Similarity	NPC96268
0.8351	Intermediate Similarity	NPC471043
0.835	Intermediate Similarity	NPC15396
0.835	Intermediate Similarity	NPC124544
0.8333	Intermediate Similarity	NPC218383
0.8333	Intermediate Similarity	NPC472495
0.8333	Intermediate Similarity	NPC293890
0.8333	Intermediate Similarity	NPC267921
0.8318	Intermediate Similarity	NPC130302
0.8318	Intermediate Similarity	NPC255655
0.8318	Intermediate Similarity	NPC98633
0.8317	Intermediate Similarity	NPC10864
0.8302	Intermediate Similarity	NPC273155
0.83	Intermediate Similarity	NPC263135
0.83	Intermediate Similarity	NPC288906
0.83	Intermediate Similarity	NPC210214
0.8286	Intermediate Similarity	NPC475571
0.8283	Intermediate Similarity	NPC224060
0.8283	Intermediate Similarity	NPC294263
0.8283	Intermediate Similarity	NPC26046
0.8283	Intermediate Similarity	NPC476189
0.8283	Intermediate Similarity	NPC244356
0.8269	Intermediate Similarity	NPC140723
0.8269	Intermediate Similarity	NPC159442
0.8269	Intermediate Similarity	NPC96217
0.8269	Intermediate Similarity	NPC470310
0.8257	Intermediate Similarity	NPC202889
0.8257	Intermediate Similarity	NPC472926
0.8252	Intermediate Similarity	NPC471790
0.8252	Intermediate Similarity	NPC148279
0.8241	Intermediate Similarity	NPC329953
0.8241	Intermediate Similarity	NPC157476
0.8241	Intermediate Similarity	NPC56025
0.8241	Intermediate Similarity	NPC471251
0.8235	Intermediate Similarity	NPC26270
0.8211	Intermediate Similarity	NPC263974
0.8208	Intermediate Similarity	NPC186054
0.82	Intermediate Similarity	NPC191094
0.82	Intermediate Similarity	NPC272635
0.82	Intermediate Similarity	NPC302008
0.82	Intermediate Similarity	NPC169751
0.819	Intermediate Similarity	NPC202793
0.819	Intermediate Similarity	NPC13149
0.819	Intermediate Similarity	NPC301787
0.819	Intermediate Similarity	NPC474558
0.8182	Intermediate Similarity	NPC130840
0.8182	Intermediate Similarity	NPC476168
0.8173	Intermediate Similarity	NPC271980
0.8173	Intermediate Similarity	NPC475803
0.8173	Intermediate Similarity	NPC309388
0.8173	Intermediate Similarity	NPC193934
0.8155	Intermediate Similarity	NPC15390
0.8148	Intermediate Similarity	NPC100908
0.8148	Intermediate Similarity	NPC471093
0.8148	Intermediate Similarity	NPC124053
0.8144	Intermediate Similarity	NPC472497
0.8144	Intermediate Similarity	NPC134197
0.8144	Intermediate Similarity	NPC259009
0.8137	Intermediate Similarity	NPC190080
0.8137	Intermediate Similarity	NPC111187
0.8131	Intermediate Similarity	NPC63841
0.8119	Intermediate Similarity	NPC287354
0.8119	Intermediate Similarity	NPC266431
0.8119	Intermediate Similarity	NPC241047
0.8119	Intermediate Similarity	NPC471624
0.8119	Intermediate Similarity	NPC62407
0.8119	Intermediate Similarity	NPC197158
0.8119	Intermediate Similarity	NPC138245
0.8119	Intermediate Similarity	NPC84018
0.8119	Intermediate Similarity	NPC231060
0.8113	Intermediate Similarity	NPC222833
0.8113	Intermediate Similarity	NPC196528
0.8113	Intermediate Similarity	NPC4115
0.8108	Intermediate Similarity	NPC270958
0.8105	Intermediate Similarity	NPC471037
0.81	Intermediate Similarity	NPC144739
0.81	Intermediate Similarity	NPC473690
0.81	Intermediate Similarity	NPC471902
0.81	Intermediate Similarity	NPC287118
0.81	Intermediate Similarity	NPC472496
0.81	Intermediate Similarity	NPC181594
0.81	Intermediate Similarity	NPC147272
0.8091	Intermediate Similarity	NPC285086
0.8091	Intermediate Similarity	NPC471252
0.8091	Intermediate Similarity	NPC52634
0.8091	Intermediate Similarity	NPC962
0.8081	Intermediate Similarity	NPC80401
0.8077	Intermediate Similarity	NPC14634
0.8077	Intermediate Similarity	NPC71706
0.8073	Intermediate Similarity	NPC29505
0.8073	Intermediate Similarity	NPC470311
0.8061	Intermediate Similarity	NPC16377
0.8058	Intermediate Similarity	NPC109059

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 NPC469985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	2101
0.2-0.3	3967
0.3-0.4	1853
0.4-0.5	532
0.5-0.6	218
0.6-0.7	143
0.7-0.8	114
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8286	Intermediate Similarity	NPD6675	Approved
0.8286	Intermediate Similarity	NPD7128	Approved
0.8286	Intermediate Similarity	NPD6402	Approved
0.8286	Intermediate Similarity	NPD5739	Approved
0.8131	Intermediate Similarity	NPD7320	Approved
0.8131	Intermediate Similarity	NPD6899	Approved
0.8131	Intermediate Similarity	NPD6881	Approved
0.8056	Intermediate Similarity	NPD6372	Approved
0.8056	Intermediate Similarity	NPD6373	Approved
0.8037	Intermediate Similarity	NPD5697	Approved
0.8037	Intermediate Similarity	NPD5701	Approved
0.7982	Intermediate Similarity	NPD7290	Approved
0.7982	Intermediate Similarity	NPD6319	Approved
0.7982	Intermediate Similarity	NPD6883	Approved
0.7982	Intermediate Similarity	NPD7102	Approved
0.7963	Intermediate Similarity	NPD6011	Approved
0.7909	Intermediate Similarity	NPD6617	Approved
0.7909	Intermediate Similarity	NPD6869	Approved
0.7909	Intermediate Similarity	NPD6649	Approved
0.7909	Intermediate Similarity	NPD6650	Approved
0.7909	Intermediate Similarity	NPD8130	Phase 1
0.7909	Intermediate Similarity	NPD6847	Approved
0.7909	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD6013	Approved
0.789	Intermediate Similarity	NPD6012	Approved
0.789	Intermediate Similarity	NPD6014	Approved
0.7863	Intermediate Similarity	NPD7492	Approved
0.7838	Intermediate Similarity	NPD8297	Approved
0.7838	Intermediate Similarity	NPD6882	Approved
0.7826	Intermediate Similarity	NPD6059	Approved
0.7826	Intermediate Similarity	NPD6054	Approved
0.7822	Intermediate Similarity	NPD8034	Phase 2
0.7822	Intermediate Similarity	NPD8035	Phase 2
0.7815	Intermediate Similarity	NPD7736	Approved
0.781	Intermediate Similarity	NPD7639	Approved
0.781	Intermediate Similarity	NPD7640	Approved
0.7798	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6616	Approved
0.7768	Intermediate Similarity	NPD4632	Approved
0.7755	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD7078	Approved
0.7731	Intermediate Similarity	NPD8293	Discontinued
0.7719	Intermediate Similarity	NPD6009	Approved
0.7714	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD6370	Approved
0.7664	Intermediate Similarity	NPD5211	Phase 2
0.7627	Intermediate Similarity	NPD7604	Phase 2
0.7619	Intermediate Similarity	NPD6083	Phase 2
0.7619	Intermediate Similarity	NPD6084	Phase 2
0.7619	Intermediate Similarity	NPD4755	Approved
0.7607	Intermediate Similarity	NPD6015	Approved
0.7607	Intermediate Similarity	NPD5983	Phase 2
0.7607	Intermediate Similarity	NPD6016	Approved
0.7542	Intermediate Similarity	NPD5988	Approved
0.7523	Intermediate Similarity	NPD5141	Approved
0.75	Intermediate Similarity	NPD6336	Discontinued
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD4634	Approved
0.7478	Intermediate Similarity	NPD6274	Approved
0.7477	Intermediate Similarity	NPD5285	Approved
0.7477	Intermediate Similarity	NPD5286	Approved
0.7477	Intermediate Similarity	NPD4700	Approved
0.7477	Intermediate Similarity	NPD4696	Approved
0.7455	Intermediate Similarity	NPD6008	Approved
0.7436	Intermediate Similarity	NPD7100	Approved
0.7436	Intermediate Similarity	NPD7101	Approved
0.7414	Intermediate Similarity	NPD6317	Approved
0.7407	Intermediate Similarity	NPD5223	Approved
0.7404	Intermediate Similarity	NPD6399	Phase 3
0.7396	Intermediate Similarity	NPD6118	Approved
0.7396	Intermediate Similarity	NPD6115	Approved
0.7396	Intermediate Similarity	NPD6114	Approved
0.7396	Intermediate Similarity	NPD6697	Approved
0.7377	Intermediate Similarity	NPD6033	Approved
0.735	Intermediate Similarity	NPD6314	Approved
0.735	Intermediate Similarity	NPD6313	Approved
0.7339	Intermediate Similarity	NPD5226	Approved
0.7339	Intermediate Similarity	NPD5225	Approved
0.7339	Intermediate Similarity	NPD5224	Approved
0.7339	Intermediate Similarity	NPD4633	Approved
0.7339	Intermediate Similarity	NPD7632	Discontinued
0.7333	Intermediate Similarity	NPD8328	Phase 3
0.7317	Intermediate Similarity	NPD7319	Approved
0.7311	Intermediate Similarity	NPD6908	Approved
0.7311	Intermediate Similarity	NPD6909	Approved
0.7304	Intermediate Similarity	NPD8133	Approved
0.7292	Intermediate Similarity	NPD6116	Phase 1
0.7282	Intermediate Similarity	NPD5328	Approved
0.7273	Intermediate Similarity	NPD5174	Approved
0.7273	Intermediate Similarity	NPD4754	Approved
0.7273	Intermediate Similarity	NPD5175	Approved
0.7265	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5695	Phase 3
0.7222	Intermediate Similarity	NPD5696	Approved
0.7213	Intermediate Similarity	NPD7507	Approved
0.72	Intermediate Similarity	NPD4788	Approved
0.7196	Intermediate Similarity	NPD5221	Approved
0.7196	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4697	Phase 3
0.7196	Intermediate Similarity	NPD5222	Approved
0.7188	Intermediate Similarity	NPD6117	Approved
0.7184	Intermediate Similarity	NPD5737	Approved
0.7184	Intermediate Similarity	NPD6672	Approved
0.7179	Intermediate Similarity	NPD6868	Approved
0.717	Intermediate Similarity	NPD7748	Approved
0.7157	Intermediate Similarity	NPD6098	Approved
0.7143	Intermediate Similarity	NPD4767	Approved
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD4768	Approved
0.713	Intermediate Similarity	NPD7902	Approved
0.713	Intermediate Similarity	NPD5173	Approved
0.7115	Intermediate Similarity	NPD6673	Approved
0.7115	Intermediate Similarity	NPD6080	Approved
0.7115	Intermediate Similarity	NPD6904	Approved
0.7083	Intermediate Similarity	NPD3703	Phase 2
0.7075	Intermediate Similarity	NPD4202	Approved
0.7025	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6921	Approved
0.7019	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4729	Approved
0.7018	Intermediate Similarity	NPD4730	Approved
0.7018	Intermediate Similarity	NPD5128	Approved
0.7	Intermediate Similarity	NPD6334	Approved
0.7	Intermediate Similarity	NPD6333	Approved
0.699	Remote Similarity	NPD5330	Approved
0.699	Remote Similarity	NPD7146	Approved
0.699	Remote Similarity	NPD7521	Approved
0.699	Remote Similarity	NPD6409	Approved
0.699	Remote Similarity	NPD6684	Approved
0.699	Remote Similarity	NPD7334	Approved
0.6981	Remote Similarity	NPD5693	Phase 1
0.6979	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7115	Discovery
0.6961	Remote Similarity	NPD4786	Approved
0.6952	Remote Similarity	NPD4753	Phase 2
0.6937	Remote Similarity	NPD1700	Approved
0.693	Remote Similarity	NPD6412	Phase 2
0.6916	Remote Similarity	NPD5778	Approved
0.6916	Remote Similarity	NPD5779	Approved
0.6897	Remote Similarity	NPD5251	Approved
0.6897	Remote Similarity	NPD5249	Phase 3
0.6897	Remote Similarity	NPD5169	Approved
0.6897	Remote Similarity	NPD5248	Approved
0.6897	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5250	Approved
0.6897	Remote Similarity	NPD5247	Approved
0.6897	Remote Similarity	NPD5135	Approved
0.6857	Remote Similarity	NPD6903	Approved
0.6852	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7900	Approved
0.6838	Remote Similarity	NPD5217	Approved
0.6838	Remote Similarity	NPD5216	Approved
0.6838	Remote Similarity	NPD5215	Approved
0.6838	Remote Similarity	NPD5127	Approved
0.6827	Remote Similarity	NPD3618	Phase 1
0.6822	Remote Similarity	NPD6050	Approved
0.6822	Remote Similarity	NPD6411	Approved
0.6822	Remote Similarity	NPD7637	Suspended
0.6796	Remote Similarity	NPD3665	Phase 1
0.6796	Remote Similarity	NPD3133	Approved
0.6796	Remote Similarity	NPD3666	Approved
0.6789	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6053	Discontinued
0.6771	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5777	Approved
0.6771	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3667	Approved
0.6754	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3702	Approved
0.6733	Remote Similarity	NPD7525	Registered
0.6731	Remote Similarity	NPD5329	Approved
0.6729	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7327	Approved
0.6639	Remote Similarity	NPD7328	Approved
0.6636	Remote Similarity	NPD4629	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD5210	Approved
0.6635	Remote Similarity	NPD4197	Approved
0.6607	Remote Similarity	NPD4225	Approved
0.6602	Remote Similarity	NPD6435	Approved
0.6585	Remote Similarity	NPD7516	Approved
0.6581	Remote Similarity	NPD6686	Approved
0.6581	Remote Similarity	NPD5168	Approved
0.6562	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3698	Phase 2
0.6532	Remote Similarity	NPD8294	Approved
0.6532	Remote Similarity	NPD8377	Approved
0.6514	Remote Similarity	NPD5281	Approved
0.6514	Remote Similarity	NPD5284	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