NPASS Compound

Structure

NPC473523 OpenBabel07101718182D 41 44 0 0 1 0 0 0 0 0999 V2000 -4.7885 -5.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1778 -5.7262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2714 -2.9365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0807 1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 4.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 4.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2959 -1.8710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5299 -4.0697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1982 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6235 0.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1842 -3.3431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8321 -4.9996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9256 -2.2098 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2339 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6235 -1.2799 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6936 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8468 0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8820 -2.4131 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5403 1.4667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.9556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8468 1.4667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6936 1.9556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6936 -0.9778 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8468 0.4889 0.0000 C 0 0 2 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 4.2339 0.4889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 2.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3871 2.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5363 -1.6865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -0.4889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3871 1.9556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 2.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 8 32 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 32 1 0 0 0 0 15 16 1 0 0 0 0 15 31 1 0 0 0 0 16 33 1 0 0 0 0 17 25 2 0 0 0 0 17 28 1 0 0 0 0 19 3 1 6 0 0 0 19 23 1 0 0 0 0 19 26 1 0 0 0 0 20 34 2 0 0 0 0 20 39 1 0 0 0 0 21 35 2 0 0 0 0 21 40 1 0 0 0 0 22 36 2 0 0 0 0 22 41 1 0 0 0 0 23 31 1 1 0 0 0 24 25 1 0 0 0 0 24 31 1 1 0 0 0 25 33 1 0 0 0 0 26 37 1 1 0 0 0 27 30 1 0 0 0 0 27 39 1 1 0 0 0 28 29 1 0 0 0 0 28 40 1 6 0 0 0 29 30 1 0 0 0 0 29 32 1 1 0 0 0 30 41 1 1 0 0 0 31 7 1 1 0 0 0 32 33 1 6 0 0 0 33 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.37
Volume:	604.874
LogP:	4.89
LogD:	4.144
LogS:	-4.658
# Rotatable Bonds:	11
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	5.223
Fsp3:	0.848
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.907
MDCK Permeability:	9.14005795493722e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.62

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	85.7082290649414%
Volume Distribution (VD):	1.726
Pgp-substrate:	3.799412488937378%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.63
CYP2C9-inhibitor:	0.258
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.565
CYP3A4-substrate:	0.593

ADMET: Excretion

Clearance (CL):	2.24
Half-life (T1/2):	0.153

ADMET: Toxicity

hERG Blockers:	0.448
Human Hepatotoxicity (H-HT):	0.814
Drug-inuced Liver Injury (DILI):	0.685
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.34
Skin Sensitization:	0.141
Carcinogencity:	0.105
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC473523

Natural Product ID:	NPC473523
*Common Name:**	Agosterol E
IUPAC Name:	[(3S,4R,5S,6S,9S,10S,13R,14R,17R)-4,6-diacetyloxy-9-hydroxy-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
Synonyms:	Agosterol E
Standard InCHIKey:	NWKRMGGGFWXFNQ-LVHOSSQSSA-N
Standard InCHI:	InChI=1S/C33H52O8/c1-18(2)9-12-26(37)19(3)23-10-11-24-25-17-28(40-21(5)35)29-30(41-22(6)36)27(39-20(4)34)13-14-32(29,8)33(25,38)16-15-31(23,24)7/h17-19,23-24,26-30,37-38H,9-16H2,1-8H3/t19-,23+,24-,26+,27-,28-,29-,30-,31+,32-,33+/m0/s1
SMILES:	CC(CC[C@H]([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@]1(C2=C[C@@H]([C@@H]2[C@]1(C)CC[C@@H]([C@@H]2OC(=O)C)OC(=O)C)OC(=O)C)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444647
PubChem CID:	11813863
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols and derivatives

*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
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510593]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[15568767]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257533]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834155]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	25.0	ug.mL-1	PMID[521294]

☑ 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 NPC473523 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	195
0.1-0.2	1345
0.2-0.3	4296
0.3-0.4	8959
0.4-0.5	12185
0.5-0.6	6228
0.6-0.7	5685
0.7-0.8	3437
0.8-0.85	330
0.85-0.9	27
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC473543
0.9688	High Similarity	NPC475344
0.9688	High Similarity	NPC476471
0.9588	High Similarity	NPC474124
0.9479	High Similarity	NPC230546
0.9381	High Similarity	NPC475617
0.9278	High Similarity	NPC473510
0.9271	High Similarity	NPC210337
0.9167	High Similarity	NPC88009
0.8835	High Similarity	NPC88701
0.8776	High Similarity	NPC276103
0.8776	High Similarity	NPC54248
0.8763	High Similarity	NPC474922
0.875	High Similarity	NPC234335
0.875	High Similarity	NPC173905
0.875	High Similarity	NPC284828
0.875	High Similarity	NPC5475
0.875	High Similarity	NPC472216
0.8738	High Similarity	NPC471205
0.8738	High Similarity	NPC475781
0.8687	High Similarity	NPC475033
0.8687	High Similarity	NPC473244
0.8687	High Similarity	NPC475032
0.8667	High Similarity	NPC472215
0.8667	High Similarity	NPC472214
0.8654	High Similarity	NPC472219
0.8654	High Similarity	NPC472218
0.8654	High Similarity	NPC472217
0.8614	High Similarity	NPC96784
0.8614	High Similarity	NPC155974
0.8614	High Similarity	NPC235920
0.8614	High Similarity	NPC472554
0.8614	High Similarity	NPC11974
0.86	High Similarity	NPC102426
0.86	High Similarity	NPC300179
0.8586	High Similarity	NPC12103
0.8586	High Similarity	NPC288970
0.8586	High Similarity	NPC284194
0.8586	High Similarity	NPC227583
0.8586	High Similarity	NPC221801
0.8586	High Similarity	NPC211810
0.8586	High Similarity	NPC471765
0.8586	High Similarity	NPC98457
0.8586	High Similarity	NPC72204
0.8571	High Similarity	NPC472416
0.8571	High Similarity	NPC472360
0.8558	High Similarity	NPC473586
0.8557	High Similarity	NPC177641
0.8544	High Similarity	NPC85593
0.8544	High Similarity	NPC31430
0.8544	High Similarity	NPC475585
0.8544	High Similarity	NPC474550
0.8544	High Similarity	NPC473577
0.8542	High Similarity	NPC246028
0.8529	High Similarity	NPC472552
0.8515	High Similarity	NPC208358
0.8515	High Similarity	NPC38855
0.85	High Similarity	NPC274793
0.8485	Intermediate Similarity	NPC8774
0.8485	Intermediate Similarity	NPC241047
0.8476	Intermediate Similarity	NPC50124
0.8476	Intermediate Similarity	NPC475263
0.8462	Intermediate Similarity	NPC220217
0.8462	Intermediate Similarity	NPC473199
0.8462	Intermediate Similarity	NPC186668
0.8462	Intermediate Similarity	NPC51719
0.8462	Intermediate Similarity	NPC471206
0.8462	Intermediate Similarity	NPC475290
0.8462	Intermediate Similarity	NPC119855
0.8454	Intermediate Similarity	NPC295668
0.8447	Intermediate Similarity	NPC473694
0.8447	Intermediate Similarity	NPC160583
0.8447	Intermediate Similarity	NPC472821
0.8447	Intermediate Similarity	NPC97487
0.8447	Intermediate Similarity	NPC475334
0.8447	Intermediate Similarity	NPC189588
0.8447	Intermediate Similarity	NPC10232
0.8447	Intermediate Similarity	NPC475623
0.8447	Intermediate Similarity	NPC281378
0.8447	Intermediate Similarity	NPC187302
0.8447	Intermediate Similarity	NPC196471
0.844	Intermediate Similarity	NPC146652
0.844	Intermediate Similarity	NPC470075
0.8431	Intermediate Similarity	NPC222875
0.8431	Intermediate Similarity	NPC268829
0.8431	Intermediate Similarity	NPC295110
0.8431	Intermediate Similarity	NPC25177
0.8431	Intermediate Similarity	NPC247701
0.8431	Intermediate Similarity	NPC289670
0.8431	Intermediate Similarity	NPC49532
0.8416	Intermediate Similarity	NPC477875
0.8416	Intermediate Similarity	NPC470068
0.8416	Intermediate Similarity	NPC470066
0.8416	Intermediate Similarity	NPC470067
0.8416	Intermediate Similarity	NPC477876
0.8416	Intermediate Similarity	NPC247233
0.8411	Intermediate Similarity	NPC470076
0.8411	Intermediate Similarity	NPC475480
0.8411	Intermediate Similarity	NPC473921
0.8411	Intermediate Similarity	NPC475668
0.84	Intermediate Similarity	NPC306797
0.84	Intermediate Similarity	NPC304899
0.84	Intermediate Similarity	NPC253115
0.84	Intermediate Similarity	NPC169270
0.84	Intermediate Similarity	NPC292718
0.84	Intermediate Similarity	NPC111834
0.84	Intermediate Similarity	NPC129569
0.84	Intermediate Similarity	NPC475178
0.84	Intermediate Similarity	NPC471903
0.8396	Intermediate Similarity	NPC475586
0.8396	Intermediate Similarity	NPC154085
0.8396	Intermediate Similarity	NPC296761
0.8396	Intermediate Similarity	NPC125361
0.8396	Intermediate Similarity	NPC43976
0.8396	Intermediate Similarity	NPC51925
0.8384	Intermediate Similarity	NPC105490
0.8384	Intermediate Similarity	NPC65402
0.8384	Intermediate Similarity	NPC127718
0.8384	Intermediate Similarity	NPC182826
0.8384	Intermediate Similarity	NPC105375
0.8384	Intermediate Similarity	NPC144202
0.8381	Intermediate Similarity	NPC122816
0.8381	Intermediate Similarity	NPC33053
0.8367	Intermediate Similarity	NPC219516
0.8367	Intermediate Similarity	NPC210268
0.8365	Intermediate Similarity	NPC288502
0.8365	Intermediate Similarity	NPC181104
0.8365	Intermediate Similarity	NPC152966
0.8365	Intermediate Similarity	NPC75608
0.8365	Intermediate Similarity	NPC201144
0.8365	Intermediate Similarity	NPC103298
0.8365	Intermediate Similarity	NPC475331
0.8365	Intermediate Similarity	NPC475335
0.8365	Intermediate Similarity	NPC93352
0.8365	Intermediate Similarity	NPC80809
0.8365	Intermediate Similarity	NPC121518
0.8364	Intermediate Similarity	NPC203862
0.8364	Intermediate Similarity	NPC93883
0.8364	Intermediate Similarity	NPC152615
0.835	Intermediate Similarity	NPC470053
0.835	Intermediate Similarity	NPC470972
0.835	Intermediate Similarity	NPC475038
0.835	Intermediate Similarity	NPC109195
0.8333	Intermediate Similarity	NPC216595
0.8333	Intermediate Similarity	NPC188968
0.8333	Intermediate Similarity	NPC167974
0.8333	Intermediate Similarity	NPC272223
0.8333	Intermediate Similarity	NPC251680
0.8333	Intermediate Similarity	NPC473567
0.8333	Intermediate Similarity	NPC166857
0.8318	Intermediate Similarity	NPC65155
0.8318	Intermediate Similarity	NPC103627
0.8318	Intermediate Similarity	NPC475563
0.8318	Intermediate Similarity	NPC475134
0.8318	Intermediate Similarity	NPC191439
0.8318	Intermediate Similarity	NPC177047
0.8318	Intermediate Similarity	NPC170974
0.8302	Intermediate Similarity	NPC38217
0.8302	Intermediate Similarity	NPC258323
0.8302	Intermediate Similarity	NPC472988
0.83	Intermediate Similarity	NPC276110
0.83	Intermediate Similarity	NPC476720
0.8286	Intermediate Similarity	NPC60315
0.8286	Intermediate Similarity	NPC472900
0.8286	Intermediate Similarity	NPC472898
0.8286	Intermediate Similarity	NPC472899
0.8286	Intermediate Similarity	NPC88349
0.8283	Intermediate Similarity	NPC7349
0.8283	Intermediate Similarity	NPC38232
0.8283	Intermediate Similarity	NPC27918
0.8283	Intermediate Similarity	NPC27531
0.8273	Intermediate Similarity	NPC207637
0.8273	Intermediate Similarity	NPC99620
0.8273	Intermediate Similarity	NPC5311
0.8273	Intermediate Similarity	NPC310341
0.8273	Intermediate Similarity	NPC193382
0.8273	Intermediate Similarity	NPC199428
0.8269	Intermediate Similarity	NPC471886
0.8269	Intermediate Similarity	NPC36688
0.8269	Intermediate Similarity	NPC471888
0.8269	Intermediate Similarity	NPC471885
0.8269	Intermediate Similarity	NPC471887
0.8265	Intermediate Similarity	NPC220216
0.8257	Intermediate Similarity	NPC962
0.8257	Intermediate Similarity	NPC250109
0.8252	Intermediate Similarity	NPC476132
0.8252	Intermediate Similarity	NPC473160
0.8252	Intermediate Similarity	NPC470054
0.8247	Intermediate Similarity	NPC474668
0.8247	Intermediate Similarity	NPC133588
0.8241	Intermediate Similarity	NPC17791
0.8241	Intermediate Similarity	NPC65167
0.8241	Intermediate Similarity	NPC250481
0.8241	Intermediate Similarity	NPC285410
0.8241	Intermediate Similarity	NPC263827
0.8235	Intermediate Similarity	NPC325229
0.8235	Intermediate Similarity	NPC476895
0.8235	Intermediate Similarity	NPC275086
0.8235	Intermediate Similarity	NPC119036
0.8235	Intermediate Similarity	NPC218107

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 NPC473523 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1510
0.2-0.3	3918
0.3-0.4	2340
0.4-0.5	698
0.5-0.6	237
0.6-0.7	199
0.7-0.8	83
0.8-0.85	3
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	NPD7640	Approved
0.8333	Intermediate Similarity	NPD7639	Approved
0.8235	Intermediate Similarity	NPD7638	Approved
0.8214	Intermediate Similarity	NPD7516	Approved
0.8142	Intermediate Similarity	NPD8377	Approved
0.8142	Intermediate Similarity	NPD8294	Approved
0.8125	Intermediate Similarity	NPD7328	Approved
0.8125	Intermediate Similarity	NPD7327	Approved
0.807	Intermediate Similarity	NPD8380	Approved
0.807	Intermediate Similarity	NPD8378	Approved
0.807	Intermediate Similarity	NPD8379	Approved
0.807	Intermediate Similarity	NPD8033	Approved
0.807	Intermediate Similarity	NPD8335	Approved
0.807	Intermediate Similarity	NPD8296	Approved
0.7913	Intermediate Similarity	NPD7503	Approved
0.7727	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7115	Discovery
0.7679	Intermediate Similarity	NPD8297	Approved
0.7664	Intermediate Similarity	NPD7632	Discontinued
0.7658	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7507	Approved
0.7624	Intermediate Similarity	NPD6051	Approved
0.7604	Intermediate Similarity	NPD7525	Registered
0.76	Intermediate Similarity	NPD7524	Approved
0.757	Intermediate Similarity	NPD5344	Discontinued
0.7547	Intermediate Similarity	NPD4225	Approved
0.7477	Intermediate Similarity	NPD6686	Approved
0.7475	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7319	Approved
0.7456	Intermediate Similarity	NPD8133	Approved
0.7455	Intermediate Similarity	NPD6675	Approved
0.7455	Intermediate Similarity	NPD7128	Approved
0.7455	Intermediate Similarity	NPD6402	Approved
0.7455	Intermediate Similarity	NPD5739	Approved
0.7411	Intermediate Similarity	NPD6373	Approved
0.7411	Intermediate Similarity	NPD6372	Approved
0.7404	Intermediate Similarity	NPD6399	Phase 3
0.7387	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6695	Phase 3
0.7373	Intermediate Similarity	NPD6319	Approved
0.7321	Intermediate Similarity	NPD7320	Approved
0.7321	Intermediate Similarity	NPD6899	Approved
0.7321	Intermediate Similarity	NPD6881	Approved
0.7315	Intermediate Similarity	NPD6648	Approved
0.7308	Intermediate Similarity	NPD7637	Suspended
0.7304	Intermediate Similarity	NPD4632	Approved
0.7281	Intermediate Similarity	NPD6649	Approved
0.7281	Intermediate Similarity	NPD6650	Approved
0.7281	Intermediate Similarity	NPD8130	Phase 1
0.7257	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7750	Discontinued
0.7255	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5701	Approved
0.7232	Intermediate Similarity	NPD5697	Approved
0.7217	Intermediate Similarity	NPD6882	Approved
0.7193	Intermediate Similarity	NPD7290	Approved
0.7193	Intermediate Similarity	NPD7102	Approved
0.7193	Intermediate Similarity	NPD6883	Approved
0.7168	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.7131	Intermediate Similarity	NPD7492	Approved
0.713	Intermediate Similarity	NPD6083	Phase 2
0.713	Intermediate Similarity	NPD6869	Approved
0.713	Intermediate Similarity	NPD6617	Approved
0.713	Intermediate Similarity	NPD6084	Phase 2
0.713	Intermediate Similarity	NPD6847	Approved
0.7119	Intermediate Similarity	NPD6009	Approved
0.7105	Intermediate Similarity	NPD6013	Approved
0.7105	Intermediate Similarity	NPD6014	Approved
0.7105	Intermediate Similarity	NPD6012	Approved
0.7097	Intermediate Similarity	NPD7736	Approved
0.7083	Intermediate Similarity	NPD7339	Approved
0.7083	Intermediate Similarity	NPD6054	Approved
0.7083	Intermediate Similarity	NPD6059	Approved
0.7083	Intermediate Similarity	NPD6942	Approved
0.708	Intermediate Similarity	NPD6412	Phase 2
0.7073	Intermediate Similarity	NPD6616	Approved
0.7071	Intermediate Similarity	NPD6930	Phase 2
0.7071	Intermediate Similarity	NPD6931	Approved
0.7069	Intermediate Similarity	NPD6053	Discontinued
0.7049	Intermediate Similarity	NPD7604	Phase 2
0.7027	Intermediate Similarity	NPD5211	Phase 2
0.7025	Intermediate Similarity	NPD5983	Phase 2
0.7018	Intermediate Similarity	NPD6011	Approved
0.7016	Intermediate Similarity	NPD7078	Approved
0.7009	Intermediate Similarity	NPD7748	Approved
0.6991	Remote Similarity	NPD6008	Approved
0.6983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4755	Approved
0.6972	Remote Similarity	NPD7902	Approved
0.697	Remote Similarity	NPD6929	Approved
0.697	Remote Similarity	NPD7645	Phase 2
0.6967	Remote Similarity	NPD6370	Approved
0.6961	Remote Similarity	NPD4786	Approved
0.6952	Remote Similarity	NPD5328	Approved
0.6937	Remote Similarity	NPD4159	Approved
0.6935	Remote Similarity	NPD6336	Discontinued
0.6916	Remote Similarity	NPD4202	Approved
0.6903	Remote Similarity	NPD5141	Approved
0.69	Remote Similarity	NPD7514	Phase 3
0.6893	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7838	Discovery
0.6885	Remote Similarity	NPD6016	Approved
0.6885	Remote Similarity	NPD6015	Approved
0.6885	Remote Similarity	NPD8516	Approved
0.6885	Remote Similarity	NPD8517	Approved
0.6885	Remote Similarity	NPD8513	Phase 3
0.6885	Remote Similarity	NPD8515	Approved
0.6847	Remote Similarity	NPD5286	Approved
0.6847	Remote Similarity	NPD4700	Approved
0.6847	Remote Similarity	NPD4696	Approved
0.6847	Remote Similarity	NPD5285	Approved
0.6837	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5988	Approved
0.6827	Remote Similarity	NPD3618	Phase 1
0.6822	Remote Similarity	NPD6079	Approved
0.6822	Remote Similarity	NPD7087	Discontinued
0.6822	Remote Similarity	NPD7515	Phase 2
0.6789	Remote Similarity	NPD5695	Phase 3
0.6774	Remote Similarity	NPD8328	Phase 3
0.6768	Remote Similarity	NPD6925	Approved
0.6768	Remote Similarity	NPD5776	Phase 2
0.6765	Remote Similarity	NPD3667	Approved
0.6757	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5696	Approved
0.6752	Remote Similarity	NPD4634	Approved
0.675	Remote Similarity	NPD6274	Approved
0.6733	Remote Similarity	NPD7332	Phase 2
0.6731	Remote Similarity	NPD6893	Approved
0.6729	Remote Similarity	NPD46	Approved
0.6729	Remote Similarity	NPD6698	Approved
0.6726	Remote Similarity	NPD5225	Approved
0.6726	Remote Similarity	NPD5226	Approved
0.6726	Remote Similarity	NPD5224	Approved
0.6726	Remote Similarity	NPD4633	Approved
0.6721	Remote Similarity	NPD7100	Approved
0.6721	Remote Similarity	NPD7101	Approved
0.67	Remote Similarity	NPD7145	Approved
0.6698	Remote Similarity	NPD5737	Approved
0.6698	Remote Similarity	NPD6672	Approved
0.6697	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7900	Approved
0.6696	Remote Similarity	NPD4767	Approved
0.6696	Remote Similarity	NPD4768	Approved
0.6695	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6902	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6639	Remote Similarity	NPD6335	Approved
0.6637	Remote Similarity	NPD5223	Approved
0.6636	Remote Similarity	NPD4753	Phase 2
0.6636	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6924	Approved
0.6633	Remote Similarity	NPD6926	Approved
0.6614	Remote Similarity	NPD8074	Phase 3
0.6613	Remote Similarity	NPD6921	Approved
0.6613	Remote Similarity	NPD6909	Approved
0.6613	Remote Similarity	NPD6908	Approved
0.661	Remote Similarity	NPD6371	Approved
0.6606	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD5779	Approved
0.66	Remote Similarity	NPD6932	Approved
0.6598	Remote Similarity	NPD4243	Approved
0.6594	Remote Similarity	NPD7625	Phase 1
0.6581	Remote Similarity	NPD4729	Approved
0.6581	Remote Similarity	NPD4730	Approved
0.6577	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5222	Approved
0.6577	Remote Similarity	NPD4697	Phase 3
0.6577	Remote Similarity	NPD5221	Approved
0.6571	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6033	Approved
0.6557	Remote Similarity	NPD6317	Approved
0.6542	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6903	Approved
0.6535	Remote Similarity	NPD6118	Approved
0.6535	Remote Similarity	NPD6115	Approved
0.6535	Remote Similarity	NPD6114	Approved
0.6535	Remote Similarity	NPD6697	Approved
0.6522	Remote Similarity	NPD4754	Approved
0.6518	Remote Similarity	NPD5173	Approved
0.6514	Remote Similarity	NPD7983	Approved
0.6509	Remote Similarity	NPD6098	Approved
0.6508	Remote Similarity	NPD6067	Discontinued
0.6505	Remote Similarity	NPD6898	Phase 1
0.6504	Remote Similarity	NPD6313	Approved
0.6504	Remote Similarity	NPD6314	Approved
0.6496	Remote Similarity	NPD7899	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