NPASS Compound

Structure

NPC251824 OpenBabel07101719252D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8510 3.7991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2232 3.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1084 -1.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0735 2.8242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4702 2.6351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 -1.8600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5630 1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6236 1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0896 0.9960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 2 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 -2.0291 2.5294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4762 2.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 -2.8600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1133 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3405 2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 27 2 0 0 0 0 12 33 1 0 0 0 0 13 28 2 0 0 0 0 13 34 1 0 0 0 0 14 29 2 0 0 0 0 14 35 1 0 0 0 0 15 8 1 1 0 0 0 16 20 1 0 0 0 0 16 33 1 6 0 0 0 17 24 1 0 0 0 0 17 30 1 6 0 0 0 18 25 1 1 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 19 32 2 0 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 25 1 1 0 0 0 22 26 1 1 0 0 0 22 34 1 0 0 0 0 23 26 1 6 0 0 0 23 35 1 0 0 0 0 25 7 1 1 0 0 0 26 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.24
Volume:	489.956
LogP:	2.068
LogD:	1.491
LogS:	-3.588
# Rotatable Bonds:	6
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.343
Synthetic Accessibility Score:	6.42
Fsp3:	0.769
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:	-5.518
MDCK Permeability:	0.00011641866876743734
Pgp-inhibitor:	0.805
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.072
20% Bioavailability (F20%):	0.171
30% Bioavailability (F30%):	0.546

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	40.244258880615234%
Volume Distribution (VD):	1.16
Pgp-substrate:	54.14971160888672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.128
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	4.271
Half-life (T1/2):	0.274

ADMET: Toxicity

hERG Blockers:	0.341
Human Hepatotoxicity (H-HT):	0.746
Drug-inuced Liver Injury (DILI):	0.71
AMES Toxicity:	0.34
Rat Oral Acute Toxicity:	0.562
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.41
Carcinogencity:	0.114
Eye Corrosion:	0.058
Eye Irritation:	0.013
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC251824

Natural Product ID:	NPC251824
*Common Name:**	Nervonin C
IUPAC Name:	n.a.
Synonyms:	nervonin C
Standard InCHIKey:	GXBBMGOUPZDGKP-PMFMSTFJSA-N
Standard InCHI:	InChI=1S/C26H36O9/c1-11-15-8-16(33-12(2)27)20-25(7)18(31)9-17(30)24(5,6)21(25)19(32)23(35-14(4)29)26(20,10-15)22(11)34-13(3)28/h15-18,20-23,30-31H,1,8-10H2,2-7H3/t15-,16+,17+,18+,20+,21-,22-,23+,25+,26+/m1/s1
SMILES:	C=C1[C@@H]2C[C@@H]([C@H]3[C@]4(C)[C@H](C[C@@H](C(C)(C)[C@H]4C(=O)[C@@H]([C@]3(C2)[C@@H]1OC(=O)C)OC(=O)C)O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512457
PubChem CID:	44577206
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
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345641]
NPO8269	Isodon nervosus	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
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[477027]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[477027]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[477027]

☑ 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 NPC251824 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	240
0.1-0.2	1727
0.2-0.3	5488
0.3-0.4	9702
0.4-0.5	11147
0.5-0.6	6015
0.6-0.7	5789
0.7-0.8	2279
0.8-0.85	239
0.85-0.9	58
0.9-0.95	6
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC86852
0.9898	High Similarity	NPC28791
0.9697	High Similarity	NPC50535
0.9596	High Similarity	NPC47281
0.9592	High Similarity	NPC170615
0.95	High Similarity	NPC295366
0.9293	High Similarity	NPC253886
0.9293	High Similarity	NPC121218
0.9109	High Similarity	NPC469985
0.9029	High Similarity	NPC176949
0.9029	High Similarity	NPC201908
0.8932	High Similarity	NPC37600
0.8911	High Similarity	NPC295276
0.89	High Similarity	NPC28864
0.89	High Similarity	NPC20479
0.89	High Similarity	NPC38296
0.89	High Similarity	NPC98837
0.89	High Similarity	NPC162459
0.89	High Similarity	NPC38471
0.8868	High Similarity	NPC94650
0.8824	High Similarity	NPC275990
0.8812	High Similarity	NPC293866
0.8785	High Similarity	NPC40608
0.8725	High Similarity	NPC46848
0.8713	High Similarity	NPC89099
0.87	High Similarity	NPC200054
0.87	High Similarity	NPC29410
0.8692	High Similarity	NPC470281
0.8673	High Similarity	NPC130840
0.8654	High Similarity	NPC29705
0.8654	High Similarity	NPC301787
0.8641	High Similarity	NPC214946
0.8641	High Similarity	NPC286519
0.8641	High Similarity	NPC148628
0.8641	High Similarity	NPC88203
0.8641	High Similarity	NPC76866
0.8641	High Similarity	NPC304832
0.8641	High Similarity	NPC246736
0.8627	High Similarity	NPC293890
0.8614	High Similarity	NPC10864
0.86	High Similarity	NPC98639
0.8598	High Similarity	NPC124053
0.8571	High Similarity	NPC222833
0.8571	High Similarity	NPC200957
0.8571	High Similarity	NPC138908
0.8558	High Similarity	NPC87927
0.8544	High Similarity	NPC289148
0.8544	High Similarity	NPC52899
0.8544	High Similarity	NPC252614
0.8544	High Similarity	NPC163963
0.8529	High Similarity	NPC471038
0.8519	High Similarity	NPC471251
0.85	High Similarity	NPC3359
0.8491	Intermediate Similarity	NPC166993
0.8485	Intermediate Similarity	NPC198054
0.8476	Intermediate Similarity	NPC310586
0.8447	Intermediate Similarity	NPC287676
0.8431	Intermediate Similarity	NPC274793
0.8411	Intermediate Similarity	NPC112895
0.8411	Intermediate Similarity	NPC231278
0.8411	Intermediate Similarity	NPC94529
0.8411	Intermediate Similarity	NPC273155
0.8411	Intermediate Similarity	NPC218123
0.8411	Intermediate Similarity	NPC211224
0.84	Intermediate Similarity	NPC199543
0.84	Intermediate Similarity	NPC294263
0.8396	Intermediate Similarity	NPC196528
0.8384	Intermediate Similarity	NPC123252
0.8384	Intermediate Similarity	NPC194485
0.8384	Intermediate Similarity	NPC100313
0.8384	Intermediate Similarity	NPC53890
0.8384	Intermediate Similarity	NPC219937
0.8381	Intermediate Similarity	NPC122811
0.8381	Intermediate Similarity	NPC266
0.8365	Intermediate Similarity	NPC39683
0.8365	Intermediate Similarity	NPC236585
0.8364	Intermediate Similarity	NPC202889
0.835	Intermediate Similarity	NPC78427
0.835	Intermediate Similarity	NPC469986
0.835	Intermediate Similarity	NPC16911
0.835	Intermediate Similarity	NPC474793
0.8333	Intermediate Similarity	NPC471250
0.8333	Intermediate Similarity	NPC329910
0.8333	Intermediate Similarity	NPC219353
0.8317	Intermediate Similarity	NPC280804
0.8302	Intermediate Similarity	NPC84928
0.8302	Intermediate Similarity	NPC98603
0.8286	Intermediate Similarity	NPC15396
0.8273	Intermediate Similarity	NPC280782
0.8273	Intermediate Similarity	NPC476964
0.8269	Intermediate Similarity	NPC41971
0.8269	Intermediate Similarity	NPC108371
0.8269	Intermediate Similarity	NPC94906
0.8269	Intermediate Similarity	NPC180733
0.8269	Intermediate Similarity	NPC37047
0.8257	Intermediate Similarity	NPC100908
0.8257	Intermediate Similarity	NPC255655
0.8235	Intermediate Similarity	NPC470229
0.8235	Intermediate Similarity	NPC157686
0.8235	Intermediate Similarity	NPC259042
0.8235	Intermediate Similarity	NPC470232
0.8235	Intermediate Similarity	NPC62407
0.8235	Intermediate Similarity	NPC287354
0.8235	Intermediate Similarity	NPC241047
0.823	Intermediate Similarity	NPC324253
0.8224	Intermediate Similarity	NPC231530
0.8224	Intermediate Similarity	NPC265127
0.8224	Intermediate Similarity	NPC475571
0.8224	Intermediate Similarity	NPC278628
0.8218	Intermediate Similarity	NPC244356
0.8218	Intermediate Similarity	NPC224060
0.8218	Intermediate Similarity	NPC26046
0.8214	Intermediate Similarity	NPC270958
0.8208	Intermediate Similarity	NPC277074
0.8208	Intermediate Similarity	NPC216114
0.8208	Intermediate Similarity	NPC140723
0.8208	Intermediate Similarity	NPC221421
0.8208	Intermediate Similarity	NPC139347
0.8208	Intermediate Similarity	NPC96217
0.8208	Intermediate Similarity	NPC209298
0.82	Intermediate Similarity	NPC46758
0.819	Intermediate Similarity	NPC477053
0.819	Intermediate Similarity	NPC49532
0.819	Intermediate Similarity	NPC75941
0.819	Intermediate Similarity	NPC471790
0.819	Intermediate Similarity	NPC477051
0.819	Intermediate Similarity	NPC477052
0.8182	Intermediate Similarity	NPC160304
0.8182	Intermediate Similarity	NPC157476
0.8173	Intermediate Similarity	NPC476806
0.8173	Intermediate Similarity	NPC476807
0.8173	Intermediate Similarity	NPC474724
0.8173	Intermediate Similarity	NPC472028
0.8163	Intermediate Similarity	NPC472505
0.8155	Intermediate Similarity	NPC292718
0.8155	Intermediate Similarity	NPC234564
0.8155	Intermediate Similarity	NPC169270
0.8155	Intermediate Similarity	NPC306797
0.8155	Intermediate Similarity	NPC111834
0.8155	Intermediate Similarity	NPC13949
0.8148	Intermediate Similarity	NPC471246
0.8142	Intermediate Similarity	NPC473590
0.8137	Intermediate Similarity	NPC475118
0.8137	Intermediate Similarity	NPC469596
0.8137	Intermediate Similarity	NPC47853
0.8137	Intermediate Similarity	NPC470385
0.8137	Intermediate Similarity	NPC272635
0.8137	Intermediate Similarity	NPC148000
0.8137	Intermediate Similarity	NPC169751
0.8137	Intermediate Similarity	NPC225474
0.8137	Intermediate Similarity	NPC470386
0.8113	Intermediate Similarity	NPC124544
0.8113	Intermediate Similarity	NPC477054
0.8103	Intermediate Similarity	NPC222688
0.8095	Intermediate Similarity	NPC470388
0.8095	Intermediate Similarity	NPC218383
0.8081	Intermediate Similarity	NPC472497
0.8081	Intermediate Similarity	NPC472495
0.8077	Intermediate Similarity	NPC473963
0.8077	Intermediate Similarity	NPC111187
0.8077	Intermediate Similarity	NPC190080
0.8077	Intermediate Similarity	NPC253586
0.8073	Intermediate Similarity	NPC208461
0.8073	Intermediate Similarity	NPC476479
0.8073	Intermediate Similarity	NPC289702
0.807	Intermediate Similarity	NPC118638
0.8058	Intermediate Similarity	NPC288906
0.8058	Intermediate Similarity	NPC263135
0.8058	Intermediate Similarity	NPC210214
0.8058	Intermediate Similarity	NPC205173
0.8056	Intermediate Similarity	NPC285927
0.8056	Intermediate Similarity	NPC4115
0.8053	Intermediate Similarity	NPC72772
0.8053	Intermediate Similarity	NPC148458
0.8053	Intermediate Similarity	NPC469794
0.8039	Intermediate Similarity	NPC476189
0.8039	Intermediate Similarity	NPC472496
0.8037	Intermediate Similarity	NPC470310
0.8036	Intermediate Similarity	NPC962
0.8036	Intermediate Similarity	NPC471252
0.8036	Intermediate Similarity	NPC52634
0.8019	Intermediate Similarity	NPC474327
0.8019	Intermediate Similarity	NPC475958
0.8019	Intermediate Similarity	NPC148279
0.8018	Intermediate Similarity	NPC270586
0.8018	Intermediate Similarity	NPC329953
0.8018	Intermediate Similarity	NPC470311
0.8017	Intermediate Similarity	NPC470779
0.8	Intermediate Similarity	NPC469983
0.8	Intermediate Similarity	NPC119036
0.8	Intermediate Similarity	NPC221414
0.7982	Intermediate Similarity	NPC146432
0.7982	Intermediate Similarity	NPC78966
0.7982	Intermediate Similarity	NPC239273
0.7982	Intermediate Similarity	NPC470778
0.7982	Intermediate Similarity	NPC284732
0.7982	Intermediate Similarity	NPC44063
0.7981	Intermediate Similarity	NPC256227
0.7981	Intermediate Similarity	NPC470387
0.7981	Intermediate Similarity	NPC473964

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 NPC251824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	2111
0.2-0.3	3941
0.3-0.4	1845
0.4-0.5	532
0.5-0.6	229
0.6-0.7	144
0.7-0.8	105
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD6373	Approved
0.8333	Intermediate Similarity	NPD6372	Approved
0.8224	Intermediate Similarity	NPD7128	Approved
0.8224	Intermediate Similarity	NPD6675	Approved
0.8224	Intermediate Similarity	NPD5739	Approved
0.8224	Intermediate Similarity	NPD6402	Approved
0.8182	Intermediate Similarity	NPD6650	Approved
0.8182	Intermediate Similarity	NPD6649	Approved
0.8073	Intermediate Similarity	NPD7320	Approved
0.8073	Intermediate Similarity	NPD6899	Approved
0.8073	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD6881	Approved
0.7982	Intermediate Similarity	NPD5697	Approved
0.7982	Intermediate Similarity	NPD5701	Approved
0.7946	Intermediate Similarity	NPD8297	Approved
0.7946	Intermediate Similarity	NPD6882	Approved
0.7928	Intermediate Similarity	NPD6883	Approved
0.7928	Intermediate Similarity	NPD7290	Approved
0.7928	Intermediate Similarity	NPD7102	Approved
0.7857	Intermediate Similarity	NPD8130	Phase 1
0.7857	Intermediate Similarity	NPD6617	Approved
0.7857	Intermediate Similarity	NPD6869	Approved
0.7857	Intermediate Similarity	NPD6847	Approved
0.7838	Intermediate Similarity	NPD6013	Approved
0.7838	Intermediate Similarity	NPD6012	Approved
0.7838	Intermediate Similarity	NPD6014	Approved
0.783	Intermediate Similarity	NPD7638	Approved
0.7778	Intermediate Similarity	NPD6319	Approved
0.7767	Intermediate Similarity	NPD8034	Phase 2
0.7767	Intermediate Similarity	NPD8035	Phase 2
0.7757	Intermediate Similarity	NPD7640	Approved
0.7757	Intermediate Similarity	NPD7639	Approved
0.7748	Intermediate Similarity	NPD6011	Approved
0.7719	Intermediate Similarity	NPD8133	Approved
0.7699	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7507	Approved
0.757	Intermediate Similarity	NPD4755	Approved
0.757	Intermediate Similarity	NPD6083	Phase 2
0.757	Intermediate Similarity	NPD6084	Phase 2
0.7565	Intermediate Similarity	NPD4632	Approved
0.7561	Intermediate Similarity	NPD7319	Approved
0.7525	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7492	Approved
0.7521	Intermediate Similarity	NPD6009	Approved
0.748	Intermediate Similarity	NPD7736	Approved
0.7479	Intermediate Similarity	NPD6059	Approved
0.7479	Intermediate Similarity	NPD6054	Approved
0.7459	Intermediate Similarity	NPD6616	Approved
0.7455	Intermediate Similarity	NPD5211	Phase 2
0.7438	Intermediate Similarity	NPD7604	Phase 2
0.7436	Intermediate Similarity	NPD6274	Approved
0.7431	Intermediate Similarity	NPD5285	Approved
0.7431	Intermediate Similarity	NPD5286	Approved
0.7431	Intermediate Similarity	NPD4700	Approved
0.7431	Intermediate Similarity	NPD4696	Approved
0.7417	Intermediate Similarity	NPD5983	Phase 2
0.7417	Intermediate Similarity	NPD6921	Approved
0.7411	Intermediate Similarity	NPD6008	Approved
0.7398	Intermediate Similarity	NPD7078	Approved
0.7398	Intermediate Similarity	NPD8293	Discontinued
0.7395	Intermediate Similarity	NPD7100	Approved
0.7395	Intermediate Similarity	NPD7101	Approved
0.7358	Intermediate Similarity	NPD6399	Phase 3
0.7355	Intermediate Similarity	NPD6370	Approved
0.7339	Intermediate Similarity	NPD5696	Approved
0.7321	Intermediate Similarity	NPD5141	Approved
0.7317	Intermediate Similarity	NPD6336	Discontinued
0.7311	Intermediate Similarity	NPD6335	Approved
0.7297	Intermediate Similarity	NPD5224	Approved
0.7297	Intermediate Similarity	NPD7632	Discontinued
0.7297	Intermediate Similarity	NPD5226	Approved
0.7297	Intermediate Similarity	NPD5225	Approved
0.7297	Intermediate Similarity	NPD4633	Approved
0.7295	Intermediate Similarity	NPD8328	Phase 3
0.7273	Intermediate Similarity	NPD6908	Approved
0.7273	Intermediate Similarity	NPD6015	Approved
0.7273	Intermediate Similarity	NPD6909	Approved
0.7273	Intermediate Similarity	NPD6016	Approved
0.7257	Intermediate Similarity	NPD4767	Approved
0.7257	Intermediate Similarity	NPD4768	Approved
0.7232	Intermediate Similarity	NPD5174	Approved
0.7232	Intermediate Similarity	NPD5175	Approved
0.7227	Intermediate Similarity	NPD6317	Approved
0.7227	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5695	Phase 3
0.7213	Intermediate Similarity	NPD5988	Approved
0.7207	Intermediate Similarity	NPD5223	Approved
0.7172	Intermediate Similarity	NPD6118	Approved
0.7172	Intermediate Similarity	NPD6115	Approved
0.7172	Intermediate Similarity	NPD6114	Approved
0.7172	Intermediate Similarity	NPD6697	Approved
0.7167	Intermediate Similarity	NPD7327	Approved
0.7167	Intermediate Similarity	NPD6313	Approved
0.7167	Intermediate Similarity	NPD6314	Approved
0.7167	Intermediate Similarity	NPD7328	Approved
0.7156	Intermediate Similarity	NPD4697	Phase 3
0.7155	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD4634	Approved
0.713	Intermediate Similarity	NPD4730	Approved
0.713	Intermediate Similarity	NPD4729	Approved
0.7107	Intermediate Similarity	NPD7516	Approved
0.7103	Intermediate Similarity	NPD5693	Phase 1
0.7091	Intermediate Similarity	NPD7902	Approved
0.708	Intermediate Similarity	NPD4754	Approved
0.7075	Intermediate Similarity	NPD5328	Approved
0.7071	Intermediate Similarity	NPD6116	Phase 1
0.7069	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6053	Discontinued
0.7009	Intermediate Similarity	NPD5248	Approved
0.7009	Intermediate Similarity	NPD5247	Approved
0.7009	Intermediate Similarity	NPD5251	Approved
0.7009	Intermediate Similarity	NPD5249	Phase 3
0.7009	Intermediate Similarity	NPD5250	Approved
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6868	Approved
0.6992	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD8380	Approved
0.6992	Remote Similarity	NPD8296	Approved
0.6992	Remote Similarity	NPD8379	Approved
0.6992	Remote Similarity	NPD8335	Approved
0.6992	Remote Similarity	NPD8378	Approved
0.699	Remote Similarity	NPD4788	Approved
0.6983	Remote Similarity	NPD5128	Approved
0.6983	Remote Similarity	NPD6686	Approved
0.6981	Remote Similarity	NPD5737	Approved
0.6981	Remote Similarity	NPD6672	Approved
0.6972	Remote Similarity	NPD7748	Approved
0.697	Remote Similarity	NPD6117	Approved
0.6952	Remote Similarity	NPD6098	Approved
0.6944	Remote Similarity	NPD6079	Approved
0.6944	Remote Similarity	NPD7515	Phase 2
0.6942	Remote Similarity	NPD7115	Discovery
0.6937	Remote Similarity	NPD5173	Approved
0.6929	Remote Similarity	NPD6033	Approved
0.6923	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4753	Phase 2
0.6916	Remote Similarity	NPD6673	Approved
0.6916	Remote Similarity	NPD6904	Approved
0.6916	Remote Similarity	NPD6080	Approved
0.6911	Remote Similarity	NPD8294	Approved
0.6911	Remote Similarity	NPD8377	Approved
0.6903	Remote Similarity	NPD1700	Approved
0.6897	Remote Similarity	NPD6412	Phase 2
0.6897	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4202	Approved
0.687	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD3703	Phase 2
0.6855	Remote Similarity	NPD8033	Approved
0.6822	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7900	Approved
0.6807	Remote Similarity	NPD5215	Approved
0.6807	Remote Similarity	NPD5216	Approved
0.6807	Remote Similarity	NPD5217	Approved
0.6792	Remote Similarity	NPD7334	Approved
0.6792	Remote Similarity	NPD7146	Approved
0.6792	Remote Similarity	NPD6684	Approved
0.6792	Remote Similarity	NPD5330	Approved
0.6792	Remote Similarity	NPD7521	Approved
0.6792	Remote Similarity	NPD3618	Phase 1
0.6792	Remote Similarity	NPD6409	Approved
0.6768	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4786	Approved
0.6757	Remote Similarity	NPD5210	Approved
0.6757	Remote Similarity	NPD4629	Approved
0.6757	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5135	Approved
0.6723	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6636	Remote Similarity	NPD6050	Approved
0.6604	Remote Similarity	NPD3665	Phase 1
0.6604	Remote Similarity	NPD3133	Approved
0.6604	Remote Similarity	NPD3666	Approved
0.6593	Remote Similarity	NPD6334	Approved
0.6593	Remote Similarity	NPD6333	Approved
0.6587	Remote Similarity	NPD7503	Approved
0.6579	Remote Similarity	NPD4225	Approved
0.6571	Remote Similarity	NPD3667	Approved
0.6571	Remote Similarity	NPD6435	Approved
0.6566	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5777	Approved
0.6566	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5692	Phase 3
0.6542	Remote Similarity	NPD5329	Approved
0.6538	Remote Similarity	NPD7525	Registered
0.6535	Remote Similarity	NPD3702	Approved
0.6515	Remote Similarity	NPD7260	Phase 2
0.6504	Remote Similarity	NPD5167	Approved
0.6486	Remote Similarity	NPD5281	Approved
0.6486	Remote Similarity	NPD7637	Suspended
0.6486	Remote Similarity	NPD5694	Approved
0.6486	Remote Similarity	NPD6411	Approved
0.6486	Remote Similarity	NPD5284	Approved
0.6479	Remote Similarity	NPD7236	Approved
0.6465	Remote Similarity	NPD4789	Approved
0.6465	Remote Similarity	NPD4245	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