NPASS Compound

Structure

NPC475617 OpenBabel07101719522D 38 41 0 0 1 0 0 0 0 0999 V2000 -5.7633 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1161 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 -4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7852 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 -2.2248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 30 1 0 0 0 0 14 20 2 0 0 0 0 14 26 1 0 0 0 0 15 25 1 0 0 0 0 15 31 1 0 0 0 0 17 3 1 6 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 32 2 0 0 0 0 18 37 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 31 1 1 0 0 0 22 31 1 1 0 0 0 23 34 1 1 0 0 0 24 29 1 0 0 0 0 24 35 1 1 0 0 0 25 27 1 0 0 0 0 25 36 1 6 0 0 0 26 28 1 0 0 0 0 26 37 1 6 0 0 0 27 30 1 1 0 0 0 28 29 1 0 0 0 0 28 30 1 1 0 0 0 29 38 1 1 0 0 0 30 6 1 1 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.36
Volume:	564.128
LogP:	4.253
LogD:	4.229
LogS:	-4.031
# Rotatable Bonds:	9
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	5.28
Fsp3:	0.871
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:	-4.785
MDCK Permeability:	8.759822958381847e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.497
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.811

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	89.48839569091797%
Volume Distribution (VD):	1.48
Pgp-substrate:	3.01153826713562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.388
CYP2C9-inhibitor:	0.223
CYP2C9-substrate:	0.159
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.523
CYP3A4-substrate:	0.32

ADMET: Excretion

Clearance (CL):	2.897
Half-life (T1/2):	0.468

ADMET: Toxicity

hERG Blockers:	0.124
Human Hepatotoxicity (H-HT):	0.932
Drug-inuced Liver Injury (DILI):	0.787
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.117
Carcinogencity:	0.014
Eye Corrosion:	0.014
Eye Irritation:	0.031
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC475617

Natural Product ID:	NPC475617
*Common Name:**	Agosterol F
IUPAC Name:	[(3S,4R,5S,6S,9R,10R,11R,13R,14R,17R)-4-acetyloxy-3,11-dihydroxy-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl] acetate
Synonyms:	Agosterol F
Standard InCHIKey:	NOWCAXXOVHJADO-WZFIDRELSA-N
Standard InCHI:	InChI=1S/C31H50O7/c1-16(2)8-11-23(34)17(3)21-9-10-22-20-14-26(37-18(4)32)28-29(38-19(5)33)24(35)12-13-30(28,6)27(20)25(36)15-31(21,22)7/h14,16-17,21-29,34-36H,8-13,15H2,1-7H3/t17-,21+,22-,23+,24-,25+,26-,27+,28-,29-,30+,31+/m0/s1
SMILES:	CC(C)CCC(C(C)C1CCC2C1(CC(C3C2=CC(C4C3(CCC(C4OC(=O)C)O)C)OC(=O)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509385
PubChem CID:	21589702
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:0001110] Tetrahydroxy 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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	16.0	ug.mL-1	PMID[529323]
NPT2	Others	Unspecified		IC50	=	35.0	ug.mL-1	PMID[529323]

☑ 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 NPC475617 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	1263
0.2-0.3	4145
0.3-0.4	8279
0.4-0.5	12625
0.5-0.6	6426
0.6-0.7	5754
0.7-0.8	3513
0.8-0.85	434
0.85-0.9	50
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC474124
0.9684	High Similarity	NPC476471
0.9684	High Similarity	NPC475344
0.957	High Similarity	NPC88009
0.9485	High Similarity	NPC473543
0.9474	High Similarity	NPC473510
0.9468	High Similarity	NPC210337
0.9381	High Similarity	NPC473523
0.9271	High Similarity	NPC230546
0.9263	High Similarity	NPC475033
0.9263	High Similarity	NPC475032
0.914	High Similarity	NPC234335
0.898	High Similarity	NPC155974
0.8922	High Similarity	NPC173905
0.8922	High Similarity	NPC472216
0.8922	High Similarity	NPC5475
0.8922	High Similarity	NPC284828
0.8878	High Similarity	NPC208358
0.8854	High Similarity	NPC8774
0.8788	High Similarity	NPC472554
0.8776	High Similarity	NPC102426
0.8776	High Similarity	NPC300179
0.8763	High Similarity	NPC72204
0.8763	High Similarity	NPC98457
0.8763	High Similarity	NPC54248
0.8763	High Similarity	NPC227583
0.8763	High Similarity	NPC12103
0.8763	High Similarity	NPC471903
0.8763	High Similarity	NPC276103
0.8763	High Similarity	NPC288970
0.875	High Similarity	NPC65402
0.875	High Similarity	NPC474922
0.875	High Similarity	NPC470076
0.875	High Similarity	NPC127718
0.8725	High Similarity	NPC473586
0.8723	High Similarity	NPC246028
0.8713	High Similarity	NPC473577
0.8713	High Similarity	NPC474550
0.8713	High Similarity	NPC475585
0.8713	High Similarity	NPC152966
0.87	High Similarity	NPC472552
0.8687	High Similarity	NPC38855
0.8673	High Similarity	NPC274793
0.8654	High Similarity	NPC472214
0.8654	High Similarity	NPC472215
0.8641	High Similarity	NPC472218
0.8641	High Similarity	NPC88701
0.8641	High Similarity	NPC472217
0.8641	High Similarity	NPC475263
0.8641	High Similarity	NPC472219
0.8627	High Similarity	NPC186668
0.8627	High Similarity	NPC119855
0.8627	High Similarity	NPC88349
0.8627	High Similarity	NPC475290
0.8627	High Similarity	NPC220217
0.8614	High Similarity	NPC472821
0.8614	High Similarity	NPC281378
0.8602	High Similarity	NPC474970
0.86	High Similarity	NPC96784
0.86	High Similarity	NPC289670
0.86	High Similarity	NPC235920
0.86	High Similarity	NPC11974
0.8586	High Similarity	NPC470067
0.8586	High Similarity	NPC470068
0.8586	High Similarity	NPC247233
0.8586	High Similarity	NPC470066
0.8571	High Similarity	NPC211810
0.8571	High Similarity	NPC471765
0.8571	High Similarity	NPC304899
0.8571	High Similarity	NPC253115
0.8571	High Similarity	NPC221801
0.8571	High Similarity	NPC284194
0.8557	High Similarity	NPC472416
0.8557	High Similarity	NPC472360
0.8544	High Similarity	NPC475781
0.8542	High Similarity	NPC219516
0.8542	High Similarity	NPC210268
0.8529	High Similarity	NPC31430
0.8529	High Similarity	NPC93352
0.8529	High Similarity	NPC85593
0.8526	High Similarity	NPC473647
0.8526	High Similarity	NPC261320
0.8519	High Similarity	NPC203862
0.8515	High Similarity	NPC177701
0.8515	High Similarity	NPC154452
0.8515	High Similarity	NPC11956
0.8515	High Similarity	NPC470972
0.85	High Similarity	NPC228251
0.85	High Similarity	NPC477971
0.85	High Similarity	NPC477972
0.85	High Similarity	NPC474190
0.85	High Similarity	NPC161527
0.85	High Similarity	NPC219285
0.85	High Similarity	NPC477968
0.85	High Similarity	NPC20113
0.85	High Similarity	NPC188968
0.8485	Intermediate Similarity	NPC473244
0.8476	Intermediate Similarity	NPC177047
0.8469	Intermediate Similarity	NPC276110
0.8462	Intermediate Similarity	NPC50124
0.8462	Intermediate Similarity	NPC48548
0.8462	Intermediate Similarity	NPC135015
0.8462	Intermediate Similarity	NPC128795
0.8462	Intermediate Similarity	NPC217921
0.8454	Intermediate Similarity	NPC53555
0.8447	Intermediate Similarity	NPC471206
0.8438	Intermediate Similarity	NPC295668
0.8438	Intermediate Similarity	NPC220216
0.8431	Intermediate Similarity	NPC475334
0.8431	Intermediate Similarity	NPC189588
0.8431	Intermediate Similarity	NPC23584
0.8431	Intermediate Similarity	NPC10232
0.8431	Intermediate Similarity	NPC160583
0.8431	Intermediate Similarity	NPC36688
0.8431	Intermediate Similarity	NPC196471
0.8431	Intermediate Similarity	NPC187302
0.8431	Intermediate Similarity	NPC473694
0.8431	Intermediate Similarity	NPC97487
0.8431	Intermediate Similarity	NPC475623
0.8426	Intermediate Similarity	NPC207637
0.8426	Intermediate Similarity	NPC470075
0.8421	Intermediate Similarity	NPC474668
0.8416	Intermediate Similarity	NPC247701
0.8416	Intermediate Similarity	NPC222875
0.8416	Intermediate Similarity	NPC470054
0.8416	Intermediate Similarity	NPC268829
0.8416	Intermediate Similarity	NPC295110
0.8416	Intermediate Similarity	NPC476132
0.8416	Intermediate Similarity	NPC25177
0.8416	Intermediate Similarity	NPC121072
0.8416	Intermediate Similarity	NPC21064
0.8416	Intermediate Similarity	NPC49532
0.84	Intermediate Similarity	NPC477876
0.84	Intermediate Similarity	NPC477875
0.84	Intermediate Similarity	NPC476895
0.8384	Intermediate Similarity	NPC103165
0.8384	Intermediate Similarity	NPC169270
0.8384	Intermediate Similarity	NPC475178
0.8384	Intermediate Similarity	NPC210717
0.8384	Intermediate Similarity	NPC292718
0.8384	Intermediate Similarity	NPC306797
0.8384	Intermediate Similarity	NPC129569
0.8384	Intermediate Similarity	NPC111834
0.8381	Intermediate Similarity	NPC316974
0.8381	Intermediate Similarity	NPC40728
0.8367	Intermediate Similarity	NPC3359
0.8367	Intermediate Similarity	NPC105490
0.8367	Intermediate Similarity	NPC105375
0.8367	Intermediate Similarity	NPC182826
0.8365	Intermediate Similarity	NPC33053
0.8365	Intermediate Similarity	NPC88013
0.8365	Intermediate Similarity	NPC471205
0.8365	Intermediate Similarity	NPC125423
0.8364	Intermediate Similarity	NPC475041
0.8351	Intermediate Similarity	NPC177641
0.8351	Intermediate Similarity	NPC130840
0.8351	Intermediate Similarity	NPC41554
0.8351	Intermediate Similarity	NPC477574
0.8351	Intermediate Similarity	NPC124374
0.8351	Intermediate Similarity	NPC97404
0.835	Intermediate Similarity	NPC75608
0.835	Intermediate Similarity	NPC103298
0.835	Intermediate Similarity	NPC201144
0.835	Intermediate Similarity	NPC475331
0.835	Intermediate Similarity	NPC181104
0.835	Intermediate Similarity	NPC121518
0.835	Intermediate Similarity	NPC288502
0.835	Intermediate Similarity	NPC80809
0.835	Intermediate Similarity	NPC475335
0.8349	Intermediate Similarity	NPC152615
0.8333	Intermediate Similarity	NPC69576
0.8333	Intermediate Similarity	NPC471633
0.8333	Intermediate Similarity	NPC258547
0.8333	Intermediate Similarity	NPC283343
0.8333	Intermediate Similarity	NPC470053
0.8333	Intermediate Similarity	NPC470361
0.8333	Intermediate Similarity	NPC273668
0.8333	Intermediate Similarity	NPC84949
0.8333	Intermediate Similarity	NPC31354
0.8318	Intermediate Similarity	NPC470063
0.8317	Intermediate Similarity	NPC79303
0.8317	Intermediate Similarity	NPC474571
0.8317	Intermediate Similarity	NPC251680
0.8317	Intermediate Similarity	NPC167974
0.8317	Intermediate Similarity	NPC476195
0.8317	Intermediate Similarity	NPC254567
0.8316	Intermediate Similarity	NPC471779
0.8302	Intermediate Similarity	NPC475563
0.8302	Intermediate Similarity	NPC475134
0.83	Intermediate Similarity	NPC26307
0.83	Intermediate Similarity	NPC476893
0.83	Intermediate Similarity	NPC51499
0.83	Intermediate Similarity	NPC261807
0.8298	Intermediate Similarity	NPC266511
0.8298	Intermediate Similarity	NPC35933
0.8286	Intermediate Similarity	NPC38948
0.8286	Intermediate Similarity	NPC311223
0.8283	Intermediate Similarity	NPC476894
0.8283	Intermediate Similarity	NPC241047
0.8273	Intermediate Similarity	NPC218093

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 NPC475617 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1448
0.2-0.3	3789
0.3-0.4	2457
0.4-0.5	769
0.5-0.6	237
0.6-0.7	206
0.7-0.8	83
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD7638	Approved
0.8317	Intermediate Similarity	NPD7640	Approved
0.8317	Intermediate Similarity	NPD7639	Approved
0.8198	Intermediate Similarity	NPD7516	Approved
0.8108	Intermediate Similarity	NPD7328	Approved
0.8108	Intermediate Similarity	NPD7327	Approved
0.8053	Intermediate Similarity	NPD8033	Approved
0.7965	Intermediate Similarity	NPD8377	Approved
0.7965	Intermediate Similarity	NPD8294	Approved
0.7895	Intermediate Similarity	NPD8296	Approved
0.7895	Intermediate Similarity	NPD8380	Approved
0.7895	Intermediate Similarity	NPD8378	Approved
0.7895	Intermediate Similarity	NPD8379	Approved
0.7895	Intermediate Similarity	NPD8335	Approved
0.7895	Intermediate Similarity	NPD7503	Approved
0.787	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD4225	Approved
0.7857	Intermediate Similarity	NPD7115	Discovery
0.7755	Intermediate Similarity	NPD7524	Approved
0.7723	Intermediate Similarity	NPD6399	Phase 3
0.7714	Intermediate Similarity	NPD5344	Discontinued
0.7642	Intermediate Similarity	NPD7632	Discontinued
0.7627	Intermediate Similarity	NPD7507	Approved
0.7615	Intermediate Similarity	NPD6686	Approved
0.76	Intermediate Similarity	NPD6051	Approved
0.7579	Intermediate Similarity	NPD7525	Registered
0.7477	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7637	Suspended
0.7449	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7319	Approved
0.7434	Intermediate Similarity	NPD4632	Approved
0.7431	Intermediate Similarity	NPD6402	Approved
0.7431	Intermediate Similarity	NPD5739	Approved
0.7431	Intermediate Similarity	NPD6675	Approved
0.7431	Intermediate Similarity	NPD7128	Approved
0.7419	Intermediate Similarity	NPD7339	Approved
0.7419	Intermediate Similarity	NPD6942	Approved
0.7364	Intermediate Similarity	NPD6412	Phase 2
0.735	Intermediate Similarity	NPD6319	Approved
0.7347	Intermediate Similarity	NPD6695	Phase 3
0.7345	Intermediate Similarity	NPD8297	Approved
0.7297	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7320	Approved
0.7297	Intermediate Similarity	NPD6881	Approved
0.7297	Intermediate Similarity	NPD6899	Approved
0.729	Intermediate Similarity	NPD6648	Approved
0.7281	Intermediate Similarity	NPD8133	Approved
0.7273	Intermediate Similarity	NPD4786	Approved
0.7232	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6373	Approved
0.7232	Intermediate Similarity	NPD6372	Approved
0.7228	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4159	Approved
0.7207	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5701	Approved
0.7207	Intermediate Similarity	NPD5697	Approved
0.7193	Intermediate Similarity	NPD6053	Discontinued
0.7168	Intermediate Similarity	NPD7290	Approved
0.7168	Intermediate Similarity	NPD7102	Approved
0.7168	Intermediate Similarity	NPD6883	Approved
0.7158	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6008	Approved
0.7115	Intermediate Similarity	NPD8035	Phase 2
0.7115	Intermediate Similarity	NPD8034	Phase 2
0.7113	Intermediate Similarity	NPD6929	Approved
0.7113	Intermediate Similarity	NPD7645	Phase 2
0.7107	Intermediate Similarity	NPD7492	Approved
0.7105	Intermediate Similarity	NPD6869	Approved
0.7105	Intermediate Similarity	NPD8130	Phase 1
0.7105	Intermediate Similarity	NPD6617	Approved
0.7105	Intermediate Similarity	NPD6649	Approved
0.7105	Intermediate Similarity	NPD6847	Approved
0.7105	Intermediate Similarity	NPD6650	Approved
0.7103	Intermediate Similarity	NPD6084	Phase 2
0.7103	Intermediate Similarity	NPD6083	Phase 2
0.7094	Intermediate Similarity	NPD6009	Approved
0.7087	Intermediate Similarity	NPD5328	Approved
0.708	Intermediate Similarity	NPD6014	Approved
0.708	Intermediate Similarity	NPD6013	Approved
0.708	Intermediate Similarity	NPD6012	Approved
0.7071	Intermediate Similarity	NPD3667	Approved
0.7059	Intermediate Similarity	NPD6059	Approved
0.7059	Intermediate Similarity	NPD6054	Approved
0.7059	Intermediate Similarity	NPD7750	Discontinued
0.7049	Intermediate Similarity	NPD6616	Approved
0.7043	Intermediate Similarity	NPD6882	Approved
0.7041	Intermediate Similarity	NPD6930	Phase 2
0.7041	Intermediate Similarity	NPD6931	Approved
0.703	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7604	Phase 2
0.7019	Intermediate Similarity	NPD46	Approved
0.7019	Intermediate Similarity	NPD6698	Approved
0.7019	Intermediate Similarity	NPD7838	Discovery
0.7	Intermediate Similarity	NPD5983	Phase 2
0.6992	Remote Similarity	NPD7078	Approved
0.6992	Remote Similarity	NPD8293	Discontinued
0.6991	Remote Similarity	NPD6011	Approved
0.6981	Remote Similarity	NPD7748	Approved
0.6979	Remote Similarity	NPD6933	Approved
0.6961	Remote Similarity	NPD3618	Phase 1
0.6957	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7515	Phase 2
0.6952	Remote Similarity	NPD6079	Approved
0.6944	Remote Similarity	NPD4755	Approved
0.6944	Remote Similarity	NPD7902	Approved
0.6942	Remote Similarity	NPD6370	Approved
0.6935	Remote Similarity	NPD7736	Approved
0.6911	Remote Similarity	NPD6336	Discontinued
0.6907	Remote Similarity	NPD6925	Approved
0.6907	Remote Similarity	NPD5776	Phase 2
0.6887	Remote Similarity	NPD4202	Approved
0.687	Remote Similarity	NPD4634	Approved
0.6869	Remote Similarity	NPD7514	Phase 3
0.686	Remote Similarity	NPD6015	Approved
0.686	Remote Similarity	NPD6016	Approved
0.6847	Remote Similarity	NPD5211	Phase 2
0.6837	Remote Similarity	NPD7145	Approved
0.6827	Remote Similarity	NPD5737	Approved
0.6827	Remote Similarity	NPD6672	Approved
0.6818	Remote Similarity	NPD5285	Approved
0.6818	Remote Similarity	NPD5286	Approved
0.6818	Remote Similarity	NPD4700	Approved
0.6818	Remote Similarity	NPD4696	Approved
0.6807	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5988	Approved
0.68	Remote Similarity	NPD6902	Approved
0.6796	Remote Similarity	NPD7334	Approved
0.6796	Remote Similarity	NPD7146	Approved
0.6796	Remote Similarity	NPD6684	Approved
0.6796	Remote Similarity	NPD5330	Approved
0.6796	Remote Similarity	NPD7521	Approved
0.6796	Remote Similarity	NPD6409	Approved
0.6792	Remote Similarity	NPD7087	Discontinued
0.6771	Remote Similarity	NPD6926	Approved
0.6771	Remote Similarity	NPD6924	Approved
0.6765	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5695	Phase 3
0.6748	Remote Similarity	NPD8328	Phase 3
0.6735	Remote Similarity	NPD6932	Approved
0.6729	Remote Similarity	NPD5779	Approved
0.6729	Remote Similarity	NPD5778	Approved
0.6727	Remote Similarity	NPD5696	Approved
0.6726	Remote Similarity	NPD5141	Approved
0.6724	Remote Similarity	NPD6371	Approved
0.6723	Remote Similarity	NPD6274	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8513	Phase 3
0.67	Remote Similarity	NPD7332	Phase 2
0.6699	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6893	Approved
0.6697	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5222	Approved
0.6697	Remote Similarity	NPD5221	Approved
0.6697	Remote Similarity	NPD4697	Phase 3
0.6696	Remote Similarity	NPD5225	Approved
0.6696	Remote Similarity	NPD5224	Approved
0.6696	Remote Similarity	NPD5226	Approved
0.6696	Remote Similarity	NPD4633	Approved
0.6694	Remote Similarity	NPD7100	Approved
0.6694	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6640	Phase 3
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6637	Remote Similarity	NPD5174	Approved
0.6637	Remote Similarity	NPD5175	Approved
0.6636	Remote Similarity	NPD5693	Phase 1
0.6636	Remote Similarity	NPD6411	Approved
0.6636	Remote Similarity	NPD5173	Approved
0.6613	Remote Similarity	NPD6067	Discontinued
0.6612	Remote Similarity	NPD6335	Approved
0.6607	Remote Similarity	NPD5223	Approved
0.6606	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4753	Phase 2
0.6602	Remote Similarity	NPD3668	Phase 3
0.6602	Remote Similarity	NPD3665	Phase 1
0.6602	Remote Similarity	NPD3133	Approved
0.6602	Remote Similarity	NPD3666	Approved
0.66	Remote Similarity	NPD6683	Phase 2
0.6598	Remote Similarity	NPD4784	Approved
0.6598	Remote Similarity	NPD4785	Approved
0.6585	Remote Similarity	NPD6908	Approved
0.6585	Remote Similarity	NPD6909	Approved
0.6585	Remote Similarity	NPD6921	Approved
0.6583	Remote Similarity	NPD6868	Approved
0.6571	Remote Similarity	NPD4250	Approved
0.6571	Remote Similarity	NPD4251	Approved
0.6569	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7625	Phase 1
0.6566	Remote Similarity	NPD6116	Phase 1
0.6562	Remote Similarity	NPD7152	Approved
0.6562	Remote Similarity	NPD7151	Approved
0.6562	Remote Similarity	NPD4243	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