NPASS Compound

Structure

NPC473543 OpenBabel07101718182D 43 46 0 0 1 0 0 0 0 0999 V2000 4.7931 -5.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4980 -1.8916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7578 -3.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2736 -2.9393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 4.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 4.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2971 -1.8728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4480 -4.4806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2013 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6260 0.3024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1882 -3.3463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8005 -2.8225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9285 -2.2120 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2380 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1456 -3.5498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6260 -1.2812 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6952 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8476 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8858 -2.4155 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5428 1.4681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.9574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8476 1.4681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6952 1.9574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6952 -0.9787 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8476 0.4894 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 -4.2380 0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 2.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 2.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5407 -1.6881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 1.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 2.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 9 34 1 0 0 0 0 10 24 2 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 29 1 0 0 0 0 14 34 1 0 0 0 0 15 16 1 0 0 0 0 15 33 1 0 0 0 0 16 35 1 0 0 0 0 17 24 1 0 0 0 0 17 28 1 0 0 0 0 18 27 2 0 0 0 0 18 30 1 0 0 0 0 19 24 1 0 0 0 0 20 4 1 1 0 0 0 20 25 1 0 0 0 0 20 28 1 0 0 0 0 21 36 2 0 0 0 0 21 41 1 0 0 0 0 22 37 2 0 0 0 0 22 42 1 0 0 0 0 23 38 2 0 0 0 0 23 43 1 0 0 0 0 25 33 1 6 0 0 0 26 27 1 0 0 0 0 26 33 1 6 0 0 0 27 35 1 0 0 0 0 28 39 1 6 0 0 0 29 32 1 0 0 0 0 29 41 1 6 0 0 0 30 31 1 0 0 0 0 30 42 1 1 0 0 0 31 32 1 0 0 0 0 31 34 1 6 0 0 0 32 43 1 6 0 0 0 33 8 1 6 0 0 0 34 35 1 1 0 0 0 35 40 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.38
Volume:	636.83
LogP:	4.84
LogD:	4.213
LogS:	-4.983
# 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:	0.207
Synthetic Accessibility Score:	5.484
Fsp3:	0.8
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:	-4.943
MDCK Permeability:	8.280462498078123e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.273
Human Intestinal Absorption (HIA):	0.162
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	84.45113372802734%
Volume Distribution (VD):	1.605
Pgp-substrate:	4.510761737823486%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.628
CYP2C9-inhibitor:	0.271
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.296
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.76
CYP3A4-substrate:	0.741

ADMET: Excretion

Clearance (CL):	2.585
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.404
Human Hepatotoxicity (H-HT):	0.915
Drug-inuced Liver Injury (DILI):	0.699
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.906
Maximum Recommended Daily Dose:	0.839
Skin Sensitization:	0.112
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC473543

Natural Product ID:	NPC473543
*Common Name:**	Agosterol E3
IUPAC Name:	[(3S,4R,5S,6S,9S,10S,13R,14R,17R)-4,6-diacetyloxy-9-hydroxy-17-[(E,2S,3R)-3-hydroxy-5-propan-2-ylhept-5-en-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 E3
Standard InCHIKey:	JFZZWXFXZSOMDK-ZAJFTKRUSA-N
Standard InCHI:	InChI=1S/C35H54O8/c1-10-24(19(2)3)17-28(39)20(4)25-11-12-26-27-18-30(42-22(6)37)31-32(43-23(7)38)29(41-21(5)36)13-14-34(31,9)35(27,40)16-15-33(25,26)8/h10,18-20,25-26,28-32,39-40H,11-17H2,1-9H3/b24-10+/t20-,25+,26-,28+,29-,30-,31-,32-,33+,34-,35+/m0/s1
SMILES:	CC=C(CC(C(C)C1CCC2C1(CCC3(C2=CC(C4C3(CCC(C4OC(=O)C)OC(=O)C)C)OC(=O)C)O)C)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445053
PubChem CID:	11814050
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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	=	14.0	ug.mL-1	PMID[506299]

☑ 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 NPC473543 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	197
0.1-0.2	1343
0.2-0.3	4161
0.3-0.4	8380
0.4-0.5	12599
0.5-0.6	6473
0.6-0.7	5729
0.7-0.8	3422
0.8-0.85	349
0.85-0.9	34
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC473523
0.9792	High Similarity	NPC476471
0.9792	High Similarity	NPC475344
0.9691	High Similarity	NPC474124
0.9485	High Similarity	NPC475617
0.9381	High Similarity	NPC230546
0.9381	High Similarity	NPC473510
0.9175	High Similarity	NPC210337
0.9072	High Similarity	NPC88009
0.8878	High Similarity	NPC276103
0.8878	High Similarity	NPC54248
0.8866	High Similarity	NPC474922
0.8854	High Similarity	NPC234335
0.8846	High Similarity	NPC173905
0.8846	High Similarity	NPC284828
0.8846	High Similarity	NPC5475
0.8846	High Similarity	NPC472216
0.8835	High Similarity	NPC475781
0.8788	High Similarity	NPC475032
0.8788	High Similarity	NPC473244
0.8788	High Similarity	NPC475033
0.8762	High Similarity	NPC472214
0.8762	High Similarity	NPC472215
0.875	High Similarity	NPC472219
0.875	High Similarity	NPC472218
0.875	High Similarity	NPC88701
0.875	High Similarity	NPC472217
0.8713	High Similarity	NPC472554
0.8713	High Similarity	NPC155974
0.8687	High Similarity	NPC288970
0.8687	High Similarity	NPC98457
0.8687	High Similarity	NPC221801
0.8687	High Similarity	NPC227583
0.8687	High Similarity	NPC284194
0.8687	High Similarity	NPC12103
0.8687	High Similarity	NPC471765
0.8687	High Similarity	NPC211810
0.8687	High Similarity	NPC72204
0.8673	High Similarity	NPC472416
0.8673	High Similarity	NPC472360
0.866	High Similarity	NPC177641
0.8654	High Similarity	NPC471205
0.8654	High Similarity	NPC473586
0.8646	High Similarity	NPC246028
0.8641	High Similarity	NPC474550
0.8641	High Similarity	NPC473577
0.8641	High Similarity	NPC475585
0.8627	High Similarity	NPC472552
0.8614	High Similarity	NPC208358
0.8614	High Similarity	NPC38855
0.8586	High Similarity	NPC8774
0.8571	High Similarity	NPC50124
0.8571	High Similarity	NPC475263
0.8558	High Similarity	NPC475290
0.8558	High Similarity	NPC119855
0.8558	High Similarity	NPC220217
0.8557	High Similarity	NPC295668
0.8544	High Similarity	NPC473694
0.8544	High Similarity	NPC475334
0.8544	High Similarity	NPC475623
0.8532	High Similarity	NPC470075
0.8532	High Similarity	NPC146652
0.8529	High Similarity	NPC11974
0.8529	High Similarity	NPC235920
0.8529	High Similarity	NPC96784
0.8515	High Similarity	NPC470067
0.8515	High Similarity	NPC102426
0.8515	High Similarity	NPC300179
0.8515	High Similarity	NPC470068
0.8515	High Similarity	NPC470066
0.8515	High Similarity	NPC247233
0.8505	High Similarity	NPC475480
0.8505	High Similarity	NPC475668
0.8505	High Similarity	NPC470076
0.8505	High Similarity	NPC473921
0.85	High Similarity	NPC304899
0.85	High Similarity	NPC129569
0.85	High Similarity	NPC471903
0.85	High Similarity	NPC475178
0.85	High Similarity	NPC253115
0.8491	Intermediate Similarity	NPC475586
0.8485	Intermediate Similarity	NPC182826
0.8485	Intermediate Similarity	NPC65402
0.8485	Intermediate Similarity	NPC105375
0.8485	Intermediate Similarity	NPC127718
0.8476	Intermediate Similarity	NPC33053
0.8462	Intermediate Similarity	NPC85593
0.8462	Intermediate Similarity	NPC75608
0.8462	Intermediate Similarity	NPC80809
0.8462	Intermediate Similarity	NPC121518
0.8462	Intermediate Similarity	NPC152966
0.8462	Intermediate Similarity	NPC201144
0.8462	Intermediate Similarity	NPC288502
0.8462	Intermediate Similarity	NPC475331
0.8462	Intermediate Similarity	NPC475335
0.8462	Intermediate Similarity	NPC181104
0.8462	Intermediate Similarity	NPC103298
0.8462	Intermediate Similarity	NPC31430
0.8462	Intermediate Similarity	NPC93352
0.8455	Intermediate Similarity	NPC203862
0.8447	Intermediate Similarity	NPC470972
0.8447	Intermediate Similarity	NPC470053
0.8431	Intermediate Similarity	NPC188968
0.8416	Intermediate Similarity	NPC274793
0.8411	Intermediate Similarity	NPC475134
0.8411	Intermediate Similarity	NPC177047
0.8411	Intermediate Similarity	NPC475563
0.84	Intermediate Similarity	NPC241047
0.84	Intermediate Similarity	NPC276110
0.8381	Intermediate Similarity	NPC471206
0.8381	Intermediate Similarity	NPC186668
0.8381	Intermediate Similarity	NPC472900
0.8381	Intermediate Similarity	NPC472898
0.8381	Intermediate Similarity	NPC60315
0.8381	Intermediate Similarity	NPC88349
0.8381	Intermediate Similarity	NPC51719
0.8381	Intermediate Similarity	NPC473199
0.8381	Intermediate Similarity	NPC472899
0.8367	Intermediate Similarity	NPC220216
0.8365	Intermediate Similarity	NPC160583
0.8365	Intermediate Similarity	NPC189588
0.8365	Intermediate Similarity	NPC97487
0.8365	Intermediate Similarity	NPC10232
0.8365	Intermediate Similarity	NPC196471
0.8365	Intermediate Similarity	NPC472821
0.8365	Intermediate Similarity	NPC36688
0.8365	Intermediate Similarity	NPC281378
0.8365	Intermediate Similarity	NPC187302
0.8364	Intermediate Similarity	NPC207637
0.8351	Intermediate Similarity	NPC474668
0.835	Intermediate Similarity	NPC49532
0.835	Intermediate Similarity	NPC470054
0.835	Intermediate Similarity	NPC476132
0.835	Intermediate Similarity	NPC222875
0.835	Intermediate Similarity	NPC25177
0.835	Intermediate Similarity	NPC247701
0.835	Intermediate Similarity	NPC289670
0.835	Intermediate Similarity	NPC268829
0.835	Intermediate Similarity	NPC295110
0.8333	Intermediate Similarity	NPC477875
0.8333	Intermediate Similarity	NPC476895
0.8333	Intermediate Similarity	NPC477876
0.8333	Intermediate Similarity	NPC17791
0.8333	Intermediate Similarity	NPC6391
0.8333	Intermediate Similarity	NPC474970
0.8333	Intermediate Similarity	NPC218107
0.8318	Intermediate Similarity	NPC154085
0.8318	Intermediate Similarity	NPC40728
0.8318	Intermediate Similarity	NPC296761
0.8318	Intermediate Similarity	NPC125361
0.8318	Intermediate Similarity	NPC51925
0.8318	Intermediate Similarity	NPC43976
0.8318	Intermediate Similarity	NPC472901
0.8317	Intermediate Similarity	NPC210717
0.8317	Intermediate Similarity	NPC111834
0.8317	Intermediate Similarity	NPC292718
0.8317	Intermediate Similarity	NPC306797
0.8317	Intermediate Similarity	NPC103165
0.8317	Intermediate Similarity	NPC475304
0.8317	Intermediate Similarity	NPC169270
0.8304	Intermediate Similarity	NPC477071
0.8304	Intermediate Similarity	NPC5883
0.8304	Intermediate Similarity	NPC475041
0.8304	Intermediate Similarity	NPC29639
0.8304	Intermediate Similarity	NPC304260
0.8304	Intermediate Similarity	NPC44899
0.8302	Intermediate Similarity	NPC472390
0.8302	Intermediate Similarity	NPC122816
0.83	Intermediate Similarity	NPC144202
0.83	Intermediate Similarity	NPC119562
0.83	Intermediate Similarity	NPC279410
0.83	Intermediate Similarity	NPC105490
0.8288	Intermediate Similarity	NPC93883
0.8288	Intermediate Similarity	NPC152615
0.8286	Intermediate Similarity	NPC470768
0.8283	Intermediate Similarity	NPC219516
0.8283	Intermediate Similarity	NPC124374
0.8283	Intermediate Similarity	NPC210268
0.8283	Intermediate Similarity	NPC41554
0.8283	Intermediate Similarity	NPC97404
0.8269	Intermediate Similarity	NPC11956
0.8269	Intermediate Similarity	NPC475038
0.8269	Intermediate Similarity	NPC109195
0.8265	Intermediate Similarity	NPC261320
0.8265	Intermediate Similarity	NPC473647
0.8265	Intermediate Similarity	NPC470361
0.8257	Intermediate Similarity	NPC473567
0.8257	Intermediate Similarity	NPC470025
0.8257	Intermediate Similarity	NPC321272
0.8257	Intermediate Similarity	NPC216595
0.8257	Intermediate Similarity	NPC317460
0.8257	Intermediate Similarity	NPC328074
0.8257	Intermediate Similarity	NPC470063
0.8252	Intermediate Similarity	NPC477971
0.8252	Intermediate Similarity	NPC79303
0.8252	Intermediate Similarity	NPC272223
0.8252	Intermediate Similarity	NPC228251
0.8252	Intermediate Similarity	NPC477968
0.8252	Intermediate Similarity	NPC20113
0.8252	Intermediate Similarity	NPC251680

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 NPC473543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1513
0.2-0.3	3803
0.3-0.4	2389
0.4-0.5	757
0.5-0.6	240
0.6-0.7	202
0.7-0.8	81
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8252	Intermediate Similarity	NPD7640	Approved
0.8252	Intermediate Similarity	NPD7639	Approved
0.8158	Intermediate Similarity	NPD8033	Approved
0.8155	Intermediate Similarity	NPD7638	Approved
0.8142	Intermediate Similarity	NPD7516	Approved
0.807	Intermediate Similarity	NPD8377	Approved
0.807	Intermediate Similarity	NPD8294	Approved
0.8053	Intermediate Similarity	NPD7328	Approved
0.8053	Intermediate Similarity	NPD7327	Approved
0.8	Intermediate Similarity	NPD8296	Approved
0.8	Intermediate Similarity	NPD8378	Approved
0.8	Intermediate Similarity	NPD8335	Approved
0.8	Intermediate Similarity	NPD8380	Approved
0.8	Intermediate Similarity	NPD8379	Approved
0.7845	Intermediate Similarity	NPD7503	Approved
0.7807	Intermediate Similarity	NPD7115	Discovery
0.77	Intermediate Similarity	NPD7524	Approved
0.7664	Intermediate Similarity	NPD5344	Discontinued
0.7658	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD4225	Approved
0.7611	Intermediate Similarity	NPD8297	Approved
0.7593	Intermediate Similarity	NPD7632	Discontinued
0.7589	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD7507	Approved
0.7576	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6051	Approved
0.7526	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD6399	Phase 3
0.7475	Intermediate Similarity	NPD6695	Phase 3
0.7411	Intermediate Similarity	NPD6686	Approved
0.7407	Intermediate Similarity	NPD6648	Approved
0.7404	Intermediate Similarity	NPD7637	Suspended
0.7398	Intermediate Similarity	NPD7319	Approved
0.7391	Intermediate Similarity	NPD8133	Approved
0.7387	Intermediate Similarity	NPD7128	Approved
0.7387	Intermediate Similarity	NPD6675	Approved
0.7387	Intermediate Similarity	NPD6402	Approved
0.7387	Intermediate Similarity	NPD5739	Approved
0.7353	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7750	Discontinued
0.7345	Intermediate Similarity	NPD6373	Approved
0.7345	Intermediate Similarity	NPD6372	Approved
0.7321	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6319	Approved
0.7257	Intermediate Similarity	NPD7320	Approved
0.7257	Intermediate Similarity	NPD6899	Approved
0.7257	Intermediate Similarity	NPD6881	Approved
0.7241	Intermediate Similarity	NPD4632	Approved
0.7217	Intermediate Similarity	NPD8130	Phase 1
0.7217	Intermediate Similarity	NPD6650	Approved
0.7217	Intermediate Similarity	NPD6649	Approved
0.7193	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6942	Approved
0.7188	Intermediate Similarity	NPD7339	Approved
0.7172	Intermediate Similarity	NPD6930	Phase 2
0.7172	Intermediate Similarity	NPD6931	Approved
0.7168	Intermediate Similarity	NPD5701	Approved
0.7168	Intermediate Similarity	NPD5697	Approved
0.7155	Intermediate Similarity	NPD6053	Discontinued
0.7155	Intermediate Similarity	NPD6882	Approved
0.713	Intermediate Similarity	NPD6883	Approved
0.713	Intermediate Similarity	NPD7290	Approved
0.713	Intermediate Similarity	NPD7102	Approved
0.7105	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8293	Discontinued
0.708	Intermediate Similarity	NPD6008	Approved
0.7075	Intermediate Similarity	NPD8035	Phase 2
0.7075	Intermediate Similarity	NPD8034	Phase 2
0.7073	Intermediate Similarity	NPD7492	Approved
0.7071	Intermediate Similarity	NPD6929	Approved
0.7069	Intermediate Similarity	NPD6847	Approved
0.7069	Intermediate Similarity	NPD6617	Approved
0.7069	Intermediate Similarity	NPD6869	Approved
0.7064	Intermediate Similarity	NPD6083	Phase 2
0.7064	Intermediate Similarity	NPD6084	Phase 2
0.7059	Intermediate Similarity	NPD4786	Approved
0.7059	Intermediate Similarity	NPD6009	Approved
0.7043	Intermediate Similarity	NPD6014	Approved
0.7043	Intermediate Similarity	NPD6013	Approved
0.7043	Intermediate Similarity	NPD6012	Approved
0.704	Intermediate Similarity	NPD7736	Approved
0.7027	Intermediate Similarity	NPD4159	Approved
0.7025	Intermediate Similarity	NPD6054	Approved
0.7025	Intermediate Similarity	NPD6059	Approved
0.7018	Intermediate Similarity	NPD6412	Phase 2
0.7016	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD7514	Phase 3
0.6992	Remote Similarity	NPD7604	Phase 2
0.6981	Remote Similarity	NPD7838	Discovery
0.6967	Remote Similarity	NPD5983	Phase 2
0.6967	Remote Similarity	NPD8513	Phase 3
0.6967	Remote Similarity	NPD8516	Approved
0.6967	Remote Similarity	NPD8517	Approved
0.6967	Remote Similarity	NPD8515	Approved
0.6964	Remote Similarity	NPD5211	Phase 2
0.696	Remote Similarity	NPD7078	Approved
0.6957	Remote Similarity	NPD6011	Approved
0.6944	Remote Similarity	NPD7748	Approved
0.6939	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7087	Discontinued
0.6911	Remote Similarity	NPD6370	Approved
0.6909	Remote Similarity	NPD7902	Approved
0.6909	Remote Similarity	NPD4755	Approved
0.69	Remote Similarity	NPD7645	Phase 2
0.6887	Remote Similarity	NPD5328	Approved
0.688	Remote Similarity	NPD6336	Discontinued
0.6869	Remote Similarity	NPD5776	Phase 2
0.6869	Remote Similarity	NPD6925	Approved
0.6863	Remote Similarity	NPD3667	Approved
0.6852	Remote Similarity	NPD4202	Approved
0.6847	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5141	Approved
0.6832	Remote Similarity	NPD7332	Phase 2
0.6829	Remote Similarity	NPD6015	Approved
0.6829	Remote Similarity	NPD6016	Approved
0.6827	Remote Similarity	NPD6893	Approved
0.6827	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD46	Approved
0.6822	Remote Similarity	NPD6698	Approved
0.68	Remote Similarity	NPD7145	Approved
0.6786	Remote Similarity	NPD4700	Approved
0.6786	Remote Similarity	NPD4696	Approved
0.6786	Remote Similarity	NPD5285	Approved
0.6786	Remote Similarity	NPD5286	Approved
0.678	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5988	Approved
0.6768	Remote Similarity	NPD6933	Approved
0.6765	Remote Similarity	NPD6902	Approved
0.6762	Remote Similarity	NPD3618	Phase 1
0.6759	Remote Similarity	NPD7515	Phase 2
0.6759	Remote Similarity	NPD6079	Approved
0.6735	Remote Similarity	NPD6926	Approved
0.6735	Remote Similarity	NPD6924	Approved
0.6731	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5695	Phase 3
0.672	Remote Similarity	NPD8328	Phase 3
0.67	Remote Similarity	NPD6932	Approved
0.6697	Remote Similarity	NPD5779	Approved
0.6697	Remote Similarity	NPD5778	Approved
0.6696	Remote Similarity	NPD5696	Approved
0.6695	Remote Similarity	NPD4634	Approved
0.6695	Remote Similarity	NPD6371	Approved
0.6694	Remote Similarity	NPD6274	Approved
0.6693	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6638	Remote Similarity	NPD4768	Approved
0.6638	Remote Similarity	NPD4767	Approved
0.6636	Remote Similarity	NPD5737	Approved
0.6636	Remote Similarity	NPD7900	Approved
0.6636	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6672	Approved
0.6609	Remote Similarity	NPD5174	Approved
0.6609	Remote Similarity	NPD5175	Approved
0.6606	Remote Similarity	NPD5693	Phase 1
0.6606	Remote Similarity	NPD7983	Approved
0.6604	Remote Similarity	NPD7334	Approved
0.6604	Remote Similarity	NPD6684	Approved
0.6604	Remote Similarity	NPD6409	Approved
0.6604	Remote Similarity	NPD5330	Approved
0.6604	Remote Similarity	NPD7521	Approved
0.6604	Remote Similarity	NPD7146	Approved
0.6602	Remote Similarity	NPD6898	Phase 1
0.6585	Remote Similarity	NPD6335	Approved
0.6581	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5223	Approved
0.6577	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4753	Phase 2
0.6569	Remote Similarity	NPD6683	Phase 2
0.6566	Remote Similarity	NPD4785	Approved
0.6566	Remote Similarity	NPD4784	Approved
0.656	Remote Similarity	NPD6908	Approved
0.656	Remote Similarity	NPD6921	Approved
0.656	Remote Similarity	NPD6909	Approved
0.6547	Remote Similarity	NPD7625	Phase 1
0.6542	Remote Similarity	NPD4251	Approved
0.6542	Remote Similarity	NPD4250	Approved
0.6531	Remote Similarity	NPD4243	Approved
0.6525	Remote Similarity	NPD4730	Approved
0.6525	Remote Similarity	NPD4729	Approved
0.6518	Remote Similarity	NPD5221	Approved
0.6518	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4697	Phase 3
0.6518	Remote Similarity	NPD5222	Approved
0.6512	Remote Similarity	NPD6033	Approved
0.6509	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4819	Approved
0.6505	Remote Similarity	NPD7509	Discontinued
0.6505	Remote Similarity	NPD4822	Approved
0.6505	Remote Similarity	NPD4820	Approved
0.6505	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4821	Approved
0.6505	Remote Similarity	NPD4748	Discontinued
0.6504	Remote Similarity	NPD6317	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