NPASS Compound

Structure

NPC156324 OpenBabel07101718232D 26 29 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 -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 -1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 0.0000 C 0 0 0 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 -2.3709 -0.2141 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 -1.2472 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 2 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 1.2650 -1.0088 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5630 -1.1691 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 0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9195 0.3930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8709 -1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6236 -1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3709 -0.2141 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 1.8885 -1.7907 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 1.1420 1.3680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 18 1 0 0 0 0 8 21 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 1 0 0 0 10 19 1 0 0 0 0 11 20 1 1 0 0 0 11 22 1 0 0 0 0 12 9 1 6 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 1 0 0 0 14 15 1 0 0 0 0 14 24 2 0 0 0 0 15 19 1 1 0 0 0 15 20 1 0 0 0 0 16 25 2 0 0 0 0 17 20 1 6 0 0 0 17 26 1 0 0 0 0 18 2 1 1 0 0 0 19 3 1 1 0 0 0 20 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.19
Volume:	365.082
LogP:	0.572
LogD:	0.145
LogS:	-3.29
# Rotatable Bonds:	1
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	6.21
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.883
MDCK Permeability:	3.4420831070747226e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.273
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.779
Plasma Protein Binding (PPB):	64.74675750732422%
Volume Distribution (VD):	0.424
Pgp-substrate:	37.157012939453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.901
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.771
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.415
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	4.225
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.337
Drug-inuced Liver Injury (DILI):	0.382
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.913
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.379
Carcinogencity:	0.115
Eye Corrosion:	0.008
Eye Irritation:	0.022
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC156324

Natural Product ID:	NPC156324
*Common Name:**	Rabdoloxin A
IUPAC Name:	n.a.
Synonyms:	Rabdoloxin A
Standard InCHIKey:	RAYXYTDTYUFFJV-OMNYJYFXSA-N
Standard InCHI:	InChI=1S/C20H28O6/c1-9-12-13(23)14(24)15-19(3)6-4-5-18(2,8-21)10(19)7-11(22)20(15,16(9)25)17(12)26/h10-13,15,17,21-23,26H,1,4-8H2,2-3H3/t10-,11-,12-,13-,15+,17-,18-,19-,20-/m1/s1
SMILES:	OC[C@@]1(C)CCC[C@@]2([C@@H]1C[C@@H](O)[C@]13[C@H]2C(=O)[C@@H]([C@H]([C@H]1O)C(=C)C3=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL549680
PubChem CID:	45271373
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
NPO18028	Isodon scoparius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19072209]
NPO18028	Isodon scoparius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28654256]
NPO18028	Isodon scoparius	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	>	10000.0	nM	PMID[548081]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[548081]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	IC50	>	10000.0	nM	PMID[548081]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[548081]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[548081]

☑ 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 NPC156324 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	232
0.1-0.2	1861
0.2-0.3	6447
0.3-0.4	11163
0.4-0.5	10510
0.5-0.6	6447
0.6-0.7	4686
0.7-0.8	1166
0.8-0.85	88
0.85-0.9	57
0.9-0.95	37
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC55503
0.9674	High Similarity	NPC140242
0.9457	High Similarity	NPC129004
0.9457	High Similarity	NPC153775
0.9457	High Similarity	NPC29247
0.9457	High Similarity	NPC289539
0.9457	High Similarity	NPC104371
0.9457	High Similarity	NPC111524
0.9457	High Similarity	NPC64006
0.9457	High Similarity	NPC215271
0.9457	High Similarity	NPC101233
0.9457	High Similarity	NPC261333
0.9457	High Similarity	NPC91772
0.9457	High Similarity	NPC292374
0.9348	High Similarity	NPC181594
0.9348	High Similarity	NPC144739
0.9271	High Similarity	NPC60947
0.9255	High Similarity	NPC135548
0.9255	High Similarity	NPC264979
0.9239	High Similarity	NPC476168
0.9239	High Similarity	NPC299185
0.9184	High Similarity	NPC84928
0.9175	High Similarity	NPC272472
0.9149	High Similarity	NPC138245
0.9149	High Similarity	NPC231060
0.9149	High Similarity	NPC84018
0.913	High Similarity	NPC149761
0.913	High Similarity	NPC261994
0.913	High Similarity	NPC80401
0.913	High Similarity	NPC180849
0.913	High Similarity	NPC470378
0.9082	High Similarity	NPC216114
0.9043	High Similarity	NPC191094
0.9043	High Similarity	NPC302008
0.899	High Similarity	NPC98603
0.8969	High Similarity	NPC127408
0.8969	High Similarity	NPC291785
0.8936	High Similarity	NPC82138
0.8936	High Similarity	NPC59170
0.8936	High Similarity	NPC59350
0.8878	High Similarity	NPC471790
0.883	High Similarity	NPC278106
0.8804	High Similarity	NPC259009
0.8804	High Similarity	NPC165895
0.8804	High Similarity	NPC153604
0.8804	High Similarity	NPC174619
0.8788	High Similarity	NPC88203
0.8788	High Similarity	NPC246736
0.8788	High Similarity	NPC214946
0.8788	High Similarity	NPC148628
0.8788	High Similarity	NPC286519
0.8788	High Similarity	NPC304832
0.8788	High Similarity	NPC76866
0.875	High Similarity	NPC29112
0.8687	High Similarity	NPC289148
0.8687	High Similarity	NPC52899
0.8687	High Similarity	NPC71706
0.8687	High Similarity	NPC163963
0.8673	High Similarity	NPC288
0.8673	High Similarity	NPC109059
0.866	High Similarity	NPC470387
0.866	High Similarity	NPC13949
0.8632	High Similarity	NPC198242
0.8632	High Similarity	NPC211403
0.8627	High Similarity	NPC176949
0.8627	High Similarity	NPC201908
0.8614	High Similarity	NPC474558
0.86	High Similarity	NPC475803
0.86	High Similarity	NPC309388
0.8587	High Similarity	NPC190704
0.8587	High Similarity	NPC102292
0.8587	High Similarity	NPC471034
0.8586	High Similarity	NPC287676
0.8571	High Similarity	NPC10864
0.8529	High Similarity	NPC4115
0.8526	High Similarity	NPC46758
0.8526	High Similarity	NPC476296
0.8515	High Similarity	NPC87927
0.8515	High Similarity	NPC266
0.85	High Similarity	NPC46848
0.8485	Intermediate Similarity	NPC16911
0.8485	Intermediate Similarity	NPC89099
0.8485	Intermediate Similarity	NPC78427
0.8478	Intermediate Similarity	NPC146683
0.8454	Intermediate Similarity	NPC470386
0.8454	Intermediate Similarity	NPC470385
0.8454	Intermediate Similarity	NPC280804
0.8431	Intermediate Similarity	NPC13149
0.8416	Intermediate Similarity	NPC275990
0.84	Intermediate Similarity	NPC293866
0.8384	Intermediate Similarity	NPC170978
0.837	Intermediate Similarity	NPC291320
0.837	Intermediate Similarity	NPC118800
0.837	Intermediate Similarity	NPC471036
0.8367	Intermediate Similarity	NPC41070
0.8367	Intermediate Similarity	NPC210214
0.8367	Intermediate Similarity	NPC470232
0.8365	Intermediate Similarity	NPC9013
0.8365	Intermediate Similarity	NPC218123
0.8365	Intermediate Similarity	NPC211224
0.8365	Intermediate Similarity	NPC112895
0.8365	Intermediate Similarity	NPC231278
0.835	Intermediate Similarity	NPC12823
0.8333	Intermediate Similarity	NPC100313
0.8317	Intermediate Similarity	NPC295276
0.83	Intermediate Similarity	NPC28864
0.83	Intermediate Similarity	NPC162459
0.83	Intermediate Similarity	NPC20479
0.83	Intermediate Similarity	NPC38296
0.83	Intermediate Similarity	NPC98837
0.83	Intermediate Similarity	NPC471038
0.83	Intermediate Similarity	NPC38471
0.8283	Intermediate Similarity	NPC165616
0.8283	Intermediate Similarity	NPC329910
0.8265	Intermediate Similarity	NPC475118
0.8261	Intermediate Similarity	NPC110780
0.8252	Intermediate Similarity	NPC202793
0.8247	Intermediate Similarity	NPC250753
0.8218	Intermediate Similarity	NPC470388
0.8211	Intermediate Similarity	NPC472497
0.819	Intermediate Similarity	NPC469733
0.819	Intermediate Similarity	NPC469729
0.819	Intermediate Similarity	NPC273155
0.819	Intermediate Similarity	NPC55973
0.8182	Intermediate Similarity	NPC98639
0.8182	Intermediate Similarity	NPC266431
0.8182	Intermediate Similarity	NPC470229
0.8182	Intermediate Similarity	NPC263135
0.8182	Intermediate Similarity	NPC288906
0.8173	Intermediate Similarity	NPC265127
0.8173	Intermediate Similarity	NPC138908
0.8173	Intermediate Similarity	NPC200957
0.8173	Intermediate Similarity	NPC37600
0.8163	Intermediate Similarity	NPC294263
0.8155	Intermediate Similarity	NPC139347
0.8155	Intermediate Similarity	NPC470310
0.8137	Intermediate Similarity	NPC14634
0.8131	Intermediate Similarity	NPC470281
0.8119	Intermediate Similarity	NPC474793
0.8105	Intermediate Similarity	NPC34190
0.81	Intermediate Similarity	NPC200054
0.81	Intermediate Similarity	NPC234564
0.81	Intermediate Similarity	NPC104568
0.81	Intermediate Similarity	NPC29410
0.8095	Intermediate Similarity	NPC469746
0.8095	Intermediate Similarity	NPC166993
0.8095	Intermediate Similarity	NPC471461
0.8095	Intermediate Similarity	NPC165873
0.8095	Intermediate Similarity	NPC67745
0.8081	Intermediate Similarity	NPC47853
0.8077	Intermediate Similarity	NPC47281
0.8056	Intermediate Similarity	NPC40608
0.8056	Intermediate Similarity	NPC473352
0.8039	Intermediate Similarity	NPC15390
0.8037	Intermediate Similarity	NPC473324
0.8037	Intermediate Similarity	NPC471093
0.8021	Intermediate Similarity	NPC57469
0.8021	Intermediate Similarity	NPC472495
0.802	Intermediate Similarity	NPC190080
0.802	Intermediate Similarity	NPC111187
0.8019	Intermediate Similarity	NPC89860
0.8019	Intermediate Similarity	NPC189663
0.8	Intermediate Similarity	NPC142352
0.8	Intermediate Similarity	NPC50535
0.8	Intermediate Similarity	NPC28791
0.8	Intermediate Similarity	NPC295366
0.8	Intermediate Similarity	NPC222833
0.7981	Intermediate Similarity	NPC159442
0.7981	Intermediate Similarity	NPC122811
0.7981	Intermediate Similarity	NPC277074
0.7981	Intermediate Similarity	NPC191892
0.7981	Intermediate Similarity	NPC469985
0.7981	Intermediate Similarity	NPC96217
0.7981	Intermediate Similarity	NPC209298
0.7981	Intermediate Similarity	NPC312900
0.798	Intermediate Similarity	NPC244356
0.798	Intermediate Similarity	NPC224060
0.798	Intermediate Similarity	NPC472496
0.7963	Intermediate Similarity	NPC472928
0.7963	Intermediate Similarity	NPC122339
0.7963	Intermediate Similarity	NPC29505
0.7963	Intermediate Similarity	NPC329953
0.7961	Intermediate Similarity	NPC236585
0.7961	Intermediate Similarity	NPC253886
0.7961	Intermediate Similarity	NPC148279
0.7961	Intermediate Similarity	NPC121218
0.7944	Intermediate Similarity	NPC118721
0.7944	Intermediate Similarity	NPC252679
0.7944	Intermediate Similarity	NPC469744
0.7941	Intermediate Similarity	NPC191565
0.7941	Intermediate Similarity	NPC476294
0.7925	Intermediate Similarity	NPC251824
0.7925	Intermediate Similarity	NPC86852
0.7925	Intermediate Similarity	NPC185
0.7921	Intermediate Similarity	NPC49371
0.7921	Intermediate Similarity	NPC192428
0.7909	Intermediate Similarity	NPC300051
0.7905	Intermediate Similarity	NPC301787
0.7905	Intermediate Similarity	NPC96268
0.79	Intermediate Similarity	NPC245972

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 NPC156324 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	2277
0.2-0.3	4149
0.3-0.4	1588
0.4-0.5	511
0.5-0.6	165
0.6-0.7	137
0.7-0.8	94
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
0.7921	Intermediate Similarity	NPD4697	Phase 3
0.787	Intermediate Similarity	NPD4634	Approved
0.7864	Intermediate Similarity	NPD5285	Approved
0.7864	Intermediate Similarity	NPD5286	Approved
0.7864	Intermediate Similarity	NPD4696	Approved
0.7843	Intermediate Similarity	NPD4755	Approved
0.7745	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD5222	Approved
0.7745	Intermediate Similarity	NPD5221	Approved
0.7714	Intermediate Similarity	NPD5225	Approved
0.7714	Intermediate Similarity	NPD4633	Approved
0.7714	Intermediate Similarity	NPD5226	Approved
0.7714	Intermediate Similarity	NPD5224	Approved
0.7714	Intermediate Similarity	NPD5211	Phase 2
0.7692	Intermediate Similarity	NPD4700	Approved
0.767	Intermediate Similarity	NPD5173	Approved
0.7647	Intermediate Similarity	NPD4629	Approved
0.7647	Intermediate Similarity	NPD5210	Approved
0.7642	Intermediate Similarity	NPD5174	Approved
0.7642	Intermediate Similarity	NPD5175	Approved
0.7619	Intermediate Similarity	NPD5223	Approved
0.757	Intermediate Similarity	NPD5141	Approved
0.7525	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7477	Intermediate Similarity	NPD6650	Approved
0.7455	Intermediate Similarity	NPD6372	Approved
0.7455	Intermediate Similarity	NPD6373	Approved
0.7431	Intermediate Similarity	NPD5697	Approved
0.7423	Intermediate Similarity	NPD4788	Approved
0.7374	Intermediate Similarity	NPD3618	Phase 1
0.7364	Intermediate Similarity	NPD4730	Approved
0.7364	Intermediate Similarity	NPD6899	Approved
0.7364	Intermediate Similarity	NPD4729	Approved
0.7364	Intermediate Similarity	NPD5128	Approved
0.7364	Intermediate Similarity	NPD6881	Approved
0.7339	Intermediate Similarity	NPD6402	Approved
0.7339	Intermediate Similarity	NPD6675	Approved
0.7339	Intermediate Similarity	NPD5739	Approved
0.7339	Intermediate Similarity	NPD4768	Approved
0.7339	Intermediate Similarity	NPD7128	Approved
0.7339	Intermediate Similarity	NPD4767	Approved
0.7327	Intermediate Similarity	NPD4753	Phase 2
0.7315	Intermediate Similarity	NPD4754	Approved
0.7312	Intermediate Similarity	NPD3703	Phase 2
0.7297	Intermediate Similarity	NPD6014	Approved
0.7297	Intermediate Similarity	NPD6012	Approved
0.7297	Intermediate Similarity	NPD6013	Approved
0.7273	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5701	Approved
0.7265	Intermediate Similarity	NPD6319	Approved
0.7265	Intermediate Similarity	NPD6054	Approved
0.7232	Intermediate Similarity	NPD5249	Phase 3
0.7232	Intermediate Similarity	NPD6883	Approved
0.7232	Intermediate Similarity	NPD7102	Approved
0.7232	Intermediate Similarity	NPD5250	Approved
0.7232	Intermediate Similarity	NPD5251	Approved
0.7232	Intermediate Similarity	NPD5247	Approved
0.7232	Intermediate Similarity	NPD5248	Approved
0.7232	Intermediate Similarity	NPD7290	Approved
0.7207	Intermediate Similarity	NPD6011	Approved
0.7207	Intermediate Similarity	NPD7320	Approved
0.7203	Intermediate Similarity	NPD6015	Approved
0.7203	Intermediate Similarity	NPD6016	Approved
0.72	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4632	Approved
0.7184	Intermediate Similarity	NPD8034	Phase 2
0.7184	Intermediate Similarity	NPD8035	Phase 2
0.7172	Intermediate Similarity	NPD4786	Approved
0.7168	Intermediate Similarity	NPD5217	Approved
0.7168	Intermediate Similarity	NPD6847	Approved
0.7168	Intermediate Similarity	NPD6869	Approved
0.7168	Intermediate Similarity	NPD6617	Approved
0.7168	Intermediate Similarity	NPD5215	Approved
0.7168	Intermediate Similarity	NPD8130	Phase 1
0.7168	Intermediate Similarity	NPD5216	Approved
0.7143	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD5988	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7119	Intermediate Similarity	NPD6059	Approved
0.7115	Intermediate Similarity	NPD4202	Approved
0.7105	Intermediate Similarity	NPD8297	Approved
0.7105	Intermediate Similarity	NPD6882	Approved
0.7103	Intermediate Similarity	NPD5696	Approved
0.708	Intermediate Similarity	NPD5169	Approved
0.708	Intermediate Similarity	NPD5135	Approved
0.708	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5168	Approved
0.7054	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7492	Approved
0.7018	Intermediate Similarity	NPD5127	Approved
0.7009	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD3665	Phase 1
0.7	Intermediate Similarity	NPD3666	Approved
0.7	Intermediate Similarity	NPD3133	Approved
0.6992	Remote Similarity	NPD7736	Approved
0.6967	Remote Similarity	NPD6616	Approved
0.6952	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD6274	Approved
0.6911	Remote Similarity	NPD7078	Approved
0.6907	Remote Similarity	NPD6114	Approved
0.6907	Remote Similarity	NPD6697	Approved
0.6907	Remote Similarity	NPD6115	Approved
0.6907	Remote Similarity	NPD6118	Approved
0.6875	Remote Similarity	NPD6008	Approved
0.687	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5279	Phase 3
0.6857	Remote Similarity	NPD7515	Phase 2
0.6852	Remote Similarity	NPD6084	Phase 2
0.6852	Remote Similarity	NPD6083	Phase 2
0.6838	Remote Similarity	NPD5167	Approved
0.6832	Remote Similarity	NPD4197	Approved
0.6809	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5983	Phase 2
0.6774	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8293	Discontinued
0.6774	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4695	Discontinued
0.6765	Remote Similarity	NPD5329	Approved
0.675	Remote Similarity	NPD7101	Approved
0.675	Remote Similarity	NPD7100	Approved
0.6723	Remote Similarity	NPD6317	Approved
0.6723	Remote Similarity	NPD7115	Discovery
0.6702	Remote Similarity	NPD4789	Approved
0.6701	Remote Similarity	NPD6117	Approved
0.6699	Remote Similarity	NPD5690	Phase 2
0.6697	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6639	Remote Similarity	NPD6868	Approved
0.6639	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7638	Approved
0.6634	Remote Similarity	NPD4221	Approved
0.6634	Remote Similarity	NPD4223	Phase 3
0.6633	Remote Similarity	NPD6116	Phase 1
0.6612	Remote Similarity	NPD4522	Approved
0.6607	Remote Similarity	NPD5091	Approved
0.66	Remote Similarity	NPD7525	Registered
0.6596	Remote Similarity	NPD3698	Phase 2
0.6587	Remote Similarity	NPD6033	Approved
0.6583	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7639	Approved
0.6577	Remote Similarity	NPD7640	Approved
0.6574	Remote Similarity	NPD7748	Approved
0.6566	Remote Similarity	NPD3617	Approved
0.656	Remote Similarity	NPD6336	Discontinued
0.6538	Remote Similarity	NPD4694	Approved
0.6538	Remote Similarity	NPD5280	Approved
0.6535	Remote Similarity	NPD7319	Approved
0.6526	Remote Similarity	NPD4244	Approved
0.6526	Remote Similarity	NPD4245	Approved
0.6504	Remote Similarity	NPD6908	Approved
0.6504	Remote Similarity	NPD6909	Approved
0.6495	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4225	Approved
0.6422	Remote Similarity	NPD5282	Discontinued
0.6422	Remote Similarity	NPD7900	Approved
0.6422	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5737	Approved
0.6415	Remote Similarity	NPD6672	Approved
0.6389	Remote Similarity	NPD6411	Approved
0.6381	Remote Similarity	NPD4689	Approved
0.6381	Remote Similarity	NPD4693	Phase 3
0.6381	Remote Similarity	NPD4688	Approved
0.6381	Remote Similarity	NPD4690	Approved
0.6381	Remote Similarity	NPD5205	Approved
0.6381	Remote Similarity	NPD4138	Approved
0.6379	Remote Similarity	NPD6412	Phase 2
0.6371	Remote Similarity	NPD6921	Approved
0.6364	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5360	Phase 3
0.6299	Remote Similarity	NPD7507	Approved
0.6289	Remote Similarity	NPD6081	Approved
0.6269	Remote Similarity	NPD6333	Approved
0.6269	Remote Similarity	NPD6334	Approved
0.6263	Remote Similarity	NPD6942	Approved
0.6263	Remote Similarity	NPD7339	Approved
0.6262	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5284	Approved
0.6239	Remote Similarity	NPD7637	Suspended
0.6239	Remote Similarity	NPD5281	Approved
0.6238	Remote Similarity	NPD3671	Phase 1
0.6228	Remote Similarity	NPD1700	Approved
0.6226	Remote Similarity	NPD7521	Approved
0.6226	Remote Similarity	NPD7334	Approved
0.6226	Remote Similarity	NPD6684	Approved
0.6226	Remote Similarity	NPD6409	Approved
0.6226	Remote Similarity	NPD7146	Approved
0.6226	Remote Similarity	NPD5330	Approved
0.6218	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5764	Clinical (unspecified phase)

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