NPASS Compound

Structure

CID110149 OpenBabel06191715462D 29 32 0 0 1 0 0 0 0 0999 V2000 -0.0805 -1.7514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3563 3.9084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2254 3.4065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5474 0.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6787 2.9050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8396 2.4209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3555 0.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6764 0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 -0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8397 -1.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5175 2.4204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5173 1.4517 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1940 1.4513 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6767 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8394 1.4522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6779 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8391 -0.4841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1943 2.4200 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3560 2.9045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9681 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 -1.6782 0.9676 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5592 -2.0989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0597 0.9507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5430 -0.4990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5438 -0.5007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0605 2.9196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 10 22 1 0 0 0 0 11 18 1 0 0 0 0 11 23 1 0 0 0 0 12 19 1 0 0 0 0 12 25 2 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 24 1 6 0 0 0 15 20 1 0 0 0 0 15 26 1 6 0 0 0 16 19 1 0 0 0 0 16 27 1 1 0 0 0 17 22 1 1 0 0 0 17 24 1 0 0 0 0 18 24 1 0 0 0 0 18 28 2 0 0 0 0 19 23 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 22 23 1 1 0 0 0 23 5 1 6 0 0 0 24 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.26
Volume:	425.476
LogP:	2.249
LogD:	2.316
LogS:	-4.046
# Rotatable Bonds:	1
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.584
Synthetic Accessibility Score:	5.065
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	1.3400440366240218e-05
Pgp-inhibitor:	0.854
Pgp-substrate:	0.547
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.922
30% Bioavailability (F30%):	0.439

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.85
Plasma Protein Binding (PPB):	61.27422332763672%
Volume Distribution (VD):	0.576
Pgp-substrate:	25.992084503173828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.229
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.304
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.316
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	8.99
Half-life (T1/2):	0.604

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.171
Carcinogencity:	0.802
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC110149

Natural Product ID:	NPC110149
*Common Name:**	Hexanorcucurbitacin F
IUPAC Name:	(2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-acetyl-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
Synonyms:	Hexanorcucurbitacin F
Standard InCHIKey:	LUCBGVQZYRKKHI-KFOIKILMSA-N
Standard InCHI:	InChI=1S/C24H36O5/c1-12(25)19-16(27)10-22(4)17-8-7-13-14(9-15(26)20(29)21(13,2)3)24(17,6)18(28)11-23(19,22)5/h7,14-17,19-20,26-27,29H,8-11H2,1-6H3/t14-,15+,16-,17+,19+,20-,22+,23-,24+/m1/s1
SMILES:	CC(=O)[C@H]1[C@H](O)C[C@@]2([C@]1(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1C[C@H](O)[C@H](C2(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484847
PubChem CID:	23247204
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003058] 20-oxosteroids

*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
NPO12307	Elaeocarpus dolichostylus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6549470]
NPO5523	Picria felterrae	Species	Linderniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5523	Picria felterrae	Species	Linderniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12307	Elaeocarpus dolichostylus	Species	Elaeocarpaceae	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
ED50	2
IC50	2

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[498518]
NPT168	Cell Line	P388	Mus musculus	ED50	>	50.0	ug ml-1	PMID[498518]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[498519]

☑ 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 NPC110149 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	200
0.1-0.2	1311
0.2-0.3	5058
0.3-0.4	12280
0.4-0.5	10162
0.5-0.6	6170
0.6-0.7	5164
0.7-0.8	2133
0.8-0.85	174
0.85-0.9	42
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC165873
0.8913	High Similarity	NPC328313
0.8913	High Similarity	NPC53911
0.8889	High Similarity	NPC191892
0.8817	High Similarity	NPC32830
0.8788	High Similarity	NPC477915
0.8763	High Similarity	NPC190554
0.8713	High Similarity	NPC149047
0.8632	High Similarity	NPC189520
0.8627	High Similarity	NPC220229
0.8627	High Similarity	NPC475060
0.8614	High Similarity	NPC204833
0.8614	High Similarity	NPC209502
0.86	High Similarity	NPC473424
0.8586	High Similarity	NPC15390
0.8557	High Similarity	NPC472485
0.8557	High Similarity	NPC473170
0.8544	High Similarity	NPC217201
0.8529	High Similarity	NPC214264
0.8529	High Similarity	NPC171137
0.8529	High Similarity	NPC152695
0.8529	High Similarity	NPC85829
0.8529	High Similarity	NPC48733
0.8529	High Similarity	NPC50692
0.8529	High Similarity	NPC319077
0.8529	High Similarity	NPC476027
0.8529	High Similarity	NPC97202
0.8529	High Similarity	NPC260268
0.8529	High Similarity	NPC49958
0.8529	High Similarity	NPC296945
0.8529	High Similarity	NPC150531
0.8529	High Similarity	NPC302607
0.8529	High Similarity	NPC202167
0.8515	High Similarity	NPC117185
0.8511	High Similarity	NPC328539
0.8485	Intermediate Similarity	NPC147954
0.8478	Intermediate Similarity	NPC221758
0.8478	Intermediate Similarity	NPC82902
0.8478	Intermediate Similarity	NPC59453
0.8469	Intermediate Similarity	NPC173272
0.8462	Intermediate Similarity	NPC11710
0.8462	Intermediate Similarity	NPC214644
0.8454	Intermediate Similarity	NPC111015
0.8447	Intermediate Similarity	NPC83744
0.8447	Intermediate Similarity	NPC477916
0.8438	Intermediate Similarity	NPC168027
0.8438	Intermediate Similarity	NPC185936
0.8438	Intermediate Similarity	NPC155304
0.8431	Intermediate Similarity	NPC149124
0.8431	Intermediate Similarity	NPC75531
0.8421	Intermediate Similarity	NPC477943
0.8421	Intermediate Similarity	NPC76879
0.8421	Intermediate Similarity	NPC1015
0.8421	Intermediate Similarity	NPC31985
0.8421	Intermediate Similarity	NPC275740
0.8421	Intermediate Similarity	NPC472971
0.8421	Intermediate Similarity	NPC86319
0.8421	Intermediate Similarity	NPC474245
0.8421	Intermediate Similarity	NPC472970
0.8404	Intermediate Similarity	NPC90652
0.8404	Intermediate Similarity	NPC475740
0.8404	Intermediate Similarity	NPC472482
0.8404	Intermediate Similarity	NPC472481
0.8404	Intermediate Similarity	NPC472484
0.8404	Intermediate Similarity	NPC138756
0.8404	Intermediate Similarity	NPC317590
0.84	Intermediate Similarity	NPC83709
0.84	Intermediate Similarity	NPC316964
0.8387	Intermediate Similarity	NPC474218
0.8384	Intermediate Similarity	NPC170978
0.8384	Intermediate Similarity	NPC18509
0.837	Intermediate Similarity	NPC476082
0.837	Intermediate Similarity	NPC278648
0.8367	Intermediate Similarity	NPC200702
0.8367	Intermediate Similarity	NPC469599
0.8367	Intermediate Similarity	NPC48330
0.8365	Intermediate Similarity	NPC329417
0.8351	Intermediate Similarity	NPC470375
0.8351	Intermediate Similarity	NPC470376
0.835	Intermediate Similarity	NPC166607
0.8333	Intermediate Similarity	NPC136801
0.8316	Intermediate Similarity	NPC471722
0.8316	Intermediate Similarity	NPC131470
0.8316	Intermediate Similarity	NPC143767
0.8316	Intermediate Similarity	NPC470417
0.8316	Intermediate Similarity	NPC471724
0.83	Intermediate Similarity	NPC477854
0.8298	Intermediate Similarity	NPC469994
0.8298	Intermediate Similarity	NPC145879
0.8298	Intermediate Similarity	NPC51014
0.8298	Intermediate Similarity	NPC20688
0.8298	Intermediate Similarity	NPC31564
0.8298	Intermediate Similarity	NPC474732
0.8298	Intermediate Similarity	NPC474733
0.8298	Intermediate Similarity	NPC474778
0.8283	Intermediate Similarity	NPC477853
0.8283	Intermediate Similarity	NPC49371
0.8269	Intermediate Similarity	NPC185
0.8269	Intermediate Similarity	NPC144459
0.8265	Intermediate Similarity	NPC245972
0.8265	Intermediate Similarity	NPC196485
0.8265	Intermediate Similarity	NPC166906
0.8261	Intermediate Similarity	NPC151519
0.8252	Intermediate Similarity	NPC477812
0.8252	Intermediate Similarity	NPC160843
0.8235	Intermediate Similarity	NPC185530
0.8235	Intermediate Similarity	NPC193934
0.8235	Intermediate Similarity	NPC271980
0.8229	Intermediate Similarity	NPC186688
0.8229	Intermediate Similarity	NPC474704
0.8229	Intermediate Similarity	NPC77263
0.8229	Intermediate Similarity	NPC69627
0.8229	Intermediate Similarity	NPC250592
0.8229	Intermediate Similarity	NPC475921
0.8229	Intermediate Similarity	NPC469319
0.8229	Intermediate Similarity	NPC229871
0.8224	Intermediate Similarity	NPC280782
0.8218	Intermediate Similarity	NPC144956
0.8211	Intermediate Similarity	NPC298904
0.8211	Intermediate Similarity	NPC58063
0.8211	Intermediate Similarity	NPC57469
0.8211	Intermediate Similarity	NPC474684
0.8211	Intermediate Similarity	NPC96496
0.8211	Intermediate Similarity	NPC142361
0.8208	Intermediate Similarity	NPC76084
0.8208	Intermediate Similarity	NPC235077
0.82	Intermediate Similarity	NPC472073
0.82	Intermediate Similarity	NPC43747
0.82	Intermediate Similarity	NPC472074
0.8191	Intermediate Similarity	NPC470574
0.8191	Intermediate Similarity	NPC469948
0.8191	Intermediate Similarity	NPC202868
0.8182	Intermediate Similarity	NPC317586
0.8182	Intermediate Similarity	NPC472932
0.8182	Intermediate Similarity	NPC266431
0.8182	Intermediate Similarity	NPC470016
0.8173	Intermediate Similarity	NPC231530
0.8173	Intermediate Similarity	NPC278628
0.8163	Intermediate Similarity	NPC477520
0.8163	Intermediate Similarity	NPC109305
0.8163	Intermediate Similarity	NPC472496
0.8163	Intermediate Similarity	NPC69454
0.8163	Intermediate Similarity	NPC475255
0.8163	Intermediate Similarity	NPC206810
0.8163	Intermediate Similarity	NPC82138
0.8155	Intermediate Similarity	NPC26478
0.8152	Intermediate Similarity	NPC474531
0.8148	Intermediate Similarity	NPC108721
0.8148	Intermediate Similarity	NPC73300
0.8144	Intermediate Similarity	NPC171441
0.8144	Intermediate Similarity	NPC180849
0.8144	Intermediate Similarity	NPC48010
0.8144	Intermediate Similarity	NPC183283
0.8144	Intermediate Similarity	NPC320026
0.8125	Intermediate Similarity	NPC242864
0.8125	Intermediate Similarity	NPC472483
0.8125	Intermediate Similarity	NPC193360
0.8125	Intermediate Similarity	NPC158778
0.8119	Intermediate Similarity	NPC114274
0.8105	Intermediate Similarity	NPC72133
0.8105	Intermediate Similarity	NPC472494
0.8105	Intermediate Similarity	NPC94755
0.8105	Intermediate Similarity	NPC472491
0.8105	Intermediate Similarity	NPC473168
0.8105	Intermediate Similarity	NPC155011
0.81	Intermediate Similarity	NPC305483
0.81	Intermediate Similarity	NPC473164
0.81	Intermediate Similarity	NPC140242
0.81	Intermediate Similarity	NPC471463
0.81	Intermediate Similarity	NPC95565
0.81	Intermediate Similarity	NPC192428
0.81	Intermediate Similarity	NPC249954
0.81	Intermediate Similarity	NPC328162
0.81	Intermediate Similarity	NPC96859
0.8095	Intermediate Similarity	NPC220974
0.8085	Intermediate Similarity	NPC472480
0.8085	Intermediate Similarity	NPC329043
0.8085	Intermediate Similarity	NPC321187
0.8085	Intermediate Similarity	NPC214043
0.8085	Intermediate Similarity	NPC161423
0.8085	Intermediate Similarity	NPC227064
0.8085	Intermediate Similarity	NPC85774
0.8085	Intermediate Similarity	NPC58841
0.8081	Intermediate Similarity	NPC472977
0.8081	Intermediate Similarity	NPC472976
0.8081	Intermediate Similarity	NPC474529
0.8077	Intermediate Similarity	NPC137657
0.8077	Intermediate Similarity	NPC284865
0.8065	Intermediate Similarity	NPC110780
0.8065	Intermediate Similarity	NPC212083
0.8061	Intermediate Similarity	NPC63748
0.8061	Intermediate Similarity	NPC154101
0.8061	Intermediate Similarity	NPC23434
0.8061	Intermediate Similarity	NPC212301
0.8061	Intermediate Similarity	NPC86266
0.8061	Intermediate Similarity	NPC272746
0.8061	Intermediate Similarity	NPC110657
0.8061	Intermediate Similarity	NPC473998
0.8061	Intermediate Similarity	NPC476168
0.8058	Intermediate Similarity	NPC473928

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 NPC110149 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1628
0.2-0.3	4126
0.3-0.4	2210
0.4-0.5	550
0.5-0.6	169
0.6-0.7	142
0.7-0.8	126
0.8-0.85	32
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8617	High Similarity	NPD5328	Approved
0.8478	Intermediate Similarity	NPD4786	Approved
0.8438	Intermediate Similarity	NPD6079	Approved
0.8384	Intermediate Similarity	NPD4755	Approved
0.8261	Intermediate Similarity	NPD3667	Approved
0.8218	Intermediate Similarity	NPD4700	Approved
0.8218	Intermediate Similarity	NPD4696	Approved
0.8218	Intermediate Similarity	NPD5286	Approved
0.8218	Intermediate Similarity	NPD5285	Approved
0.8208	Intermediate Similarity	NPD4634	Approved
0.8163	Intermediate Similarity	NPD4202	Approved
0.8137	Intermediate Similarity	NPD5223	Approved
0.8105	Intermediate Similarity	NPD3618	Phase 1
0.81	Intermediate Similarity	NPD5222	Approved
0.81	Intermediate Similarity	NPD5221	Approved
0.81	Intermediate Similarity	NPD4697	Phase 3
0.81	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD3666	Approved
0.8085	Intermediate Similarity	NPD3133	Approved
0.8085	Intermediate Similarity	NPD3665	Phase 1
0.8058	Intermediate Similarity	NPD4633	Approved
0.8058	Intermediate Similarity	NPD5211	Phase 2
0.8058	Intermediate Similarity	NPD5226	Approved
0.8058	Intermediate Similarity	NPD5225	Approved
0.8058	Intermediate Similarity	NPD5224	Approved
0.802	Intermediate Similarity	NPD5173	Approved
0.8	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD5739	Approved
0.8	Intermediate Similarity	NPD7128	Approved
0.7981	Intermediate Similarity	NPD4754	Approved
0.7981	Intermediate Similarity	NPD5174	Approved
0.7981	Intermediate Similarity	NPD5175	Approved
0.7905	Intermediate Similarity	NPD5141	Approved
0.7857	Intermediate Similarity	NPD4753	Phase 2
0.785	Intermediate Similarity	NPD6881	Approved
0.785	Intermediate Similarity	NPD6899	Approved
0.785	Intermediate Similarity	NPD7320	Approved
0.783	Intermediate Similarity	NPD4767	Approved
0.783	Intermediate Similarity	NPD4768	Approved
0.7822	Intermediate Similarity	NPD5210	Approved
0.7822	Intermediate Similarity	NPD4629	Approved
0.78	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD6373	Approved
0.7778	Intermediate Similarity	NPD6372	Approved
0.7757	Intermediate Similarity	NPD5701	Approved
0.7757	Intermediate Similarity	NPD5697	Approved
0.7732	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD8297	Approved
0.7708	Intermediate Similarity	NPD3668	Phase 3
0.7706	Intermediate Similarity	NPD7102	Approved
0.7706	Intermediate Similarity	NPD7290	Approved
0.7706	Intermediate Similarity	NPD6883	Approved
0.7685	Intermediate Similarity	NPD4729	Approved
0.7685	Intermediate Similarity	NPD5128	Approved
0.7685	Intermediate Similarity	NPD6011	Approved
0.7685	Intermediate Similarity	NPD4730	Approved
0.7684	Intermediate Similarity	NPD4221	Approved
0.7684	Intermediate Similarity	NPD4223	Phase 3
0.7658	Intermediate Similarity	NPD4632	Approved
0.7636	Intermediate Similarity	NPD6649	Approved
0.7636	Intermediate Similarity	NPD8130	Phase 1
0.7636	Intermediate Similarity	NPD6650	Approved
0.7636	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6869	Approved
0.7636	Intermediate Similarity	NPD6617	Approved
0.7636	Intermediate Similarity	NPD6847	Approved
0.7629	Intermediate Similarity	NPD5329	Approved
0.7615	Intermediate Similarity	NPD6012	Approved
0.7615	Intermediate Similarity	NPD6014	Approved
0.7615	Intermediate Similarity	NPD6013	Approved
0.7609	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6882	Approved
0.7565	Intermediate Similarity	NPD6319	Approved
0.7565	Intermediate Similarity	NPD6059	Approved
0.7565	Intermediate Similarity	NPD6054	Approved
0.7545	Intermediate Similarity	NPD5251	Approved
0.7545	Intermediate Similarity	NPD5169	Approved
0.7545	Intermediate Similarity	NPD5250	Approved
0.7545	Intermediate Similarity	NPD5248	Approved
0.7545	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5247	Approved
0.7545	Intermediate Similarity	NPD5135	Approved
0.7545	Intermediate Similarity	NPD5249	Phase 3
0.7526	Intermediate Similarity	NPD4197	Approved
0.7525	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD6942	Approved
0.7477	Intermediate Similarity	NPD5217	Approved
0.7477	Intermediate Similarity	NPD5216	Approved
0.7477	Intermediate Similarity	NPD5215	Approved
0.7477	Intermediate Similarity	NPD5127	Approved
0.7474	Intermediate Similarity	NPD7525	Registered
0.7456	Intermediate Similarity	NPD7115	Discovery
0.7449	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6370	Approved
0.7429	Intermediate Similarity	NPD5696	Approved
0.7423	Intermediate Similarity	NPD4788	Approved
0.7374	Intermediate Similarity	NPD6409	Approved
0.7374	Intermediate Similarity	NPD7146	Approved
0.7374	Intermediate Similarity	NPD5205	Approved
0.7374	Intermediate Similarity	NPD5279	Phase 3
0.7374	Intermediate Similarity	NPD4690	Approved
0.7374	Intermediate Similarity	NPD4693	Phase 3
0.7374	Intermediate Similarity	NPD4138	Approved
0.7374	Intermediate Similarity	NPD4688	Approved
0.7374	Intermediate Similarity	NPD6684	Approved
0.7374	Intermediate Similarity	NPD7521	Approved
0.7374	Intermediate Similarity	NPD7334	Approved
0.7374	Intermediate Similarity	NPD4689	Approved
0.7374	Intermediate Similarity	NPD5330	Approved
0.7364	Intermediate Similarity	NPD5168	Approved
0.735	Intermediate Similarity	NPD6016	Approved
0.735	Intermediate Similarity	NPD6015	Approved
0.7339	Intermediate Similarity	NPD6008	Approved
0.7311	Intermediate Similarity	NPD7492	Approved
0.7304	Intermediate Similarity	NPD6009	Approved
0.7288	Intermediate Similarity	NPD5988	Approved
0.7281	Intermediate Similarity	NPD5167	Approved
0.7273	Intermediate Similarity	NPD6412	Phase 2
0.725	Intermediate Similarity	NPD6616	Approved
0.7241	Intermediate Similarity	NPD6335	Approved
0.7228	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6903	Approved
0.7217	Intermediate Similarity	NPD6274	Approved
0.7212	Intermediate Similarity	NPD7748	Approved
0.72	Intermediate Similarity	NPD5690	Phase 2
0.72	Intermediate Similarity	NPD5280	Approved
0.72	Intermediate Similarity	NPD4694	Approved
0.719	Intermediate Similarity	NPD7078	Approved
0.719	Intermediate Similarity	NPD8293	Discontinued
0.7184	Intermediate Similarity	NPD6411	Approved
0.7179	Intermediate Similarity	NPD7101	Approved
0.7179	Intermediate Similarity	NPD7100	Approved
0.7155	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7736	Approved
0.7131	Intermediate Similarity	NPD6033	Approved
0.7103	Intermediate Similarity	NPD7638	Approved
0.7094	Intermediate Similarity	NPD6314	Approved
0.7094	Intermediate Similarity	NPD6313	Approved
0.7083	Intermediate Similarity	NPD7604	Phase 2
0.7069	Intermediate Similarity	NPD6868	Approved
0.7059	Intermediate Similarity	NPD6908	Approved
0.7059	Intermediate Similarity	NPD6909	Approved
0.7059	Intermediate Similarity	NPD6672	Approved
0.7059	Intermediate Similarity	NPD5983	Phase 2
0.7059	Intermediate Similarity	NPD5737	Approved
0.7053	Intermediate Similarity	NPD6933	Approved
0.7041	Intermediate Similarity	NPD4692	Approved
0.7041	Intermediate Similarity	NPD4139	Approved
0.7037	Intermediate Similarity	NPD7639	Approved
0.7037	Intermediate Similarity	NPD7640	Approved
0.703	Intermediate Similarity	NPD6098	Approved
0.7021	Intermediate Similarity	NPD4784	Approved
0.7021	Intermediate Similarity	NPD4785	Approved
0.7019	Intermediate Similarity	NPD5284	Approved
0.7019	Intermediate Similarity	NPD8035	Phase 2
0.7019	Intermediate Similarity	NPD5281	Approved
0.7019	Intermediate Similarity	NPD8034	Phase 2
0.701	Intermediate Similarity	NPD4195	Approved
0.7009	Intermediate Similarity	NPD7902	Approved
0.699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6673	Approved
0.699	Remote Similarity	NPD6904	Approved
0.699	Remote Similarity	NPD6080	Approved
0.699	Remote Similarity	NPD6101	Approved
0.6989	Remote Similarity	NPD4243	Approved
0.6989	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6336	Discontinued
0.6961	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3703	Phase 2
0.6939	Remote Similarity	NPD4695	Discontinued
0.6939	Remote Similarity	NPD4748	Discontinued
0.6935	Remote Similarity	NPD7319	Approved
0.6917	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5091	Approved
0.6907	Remote Similarity	NPD3617	Approved
0.6891	Remote Similarity	NPD4522	Approved
0.6882	Remote Similarity	NPD4245	Approved
0.6882	Remote Similarity	NPD4244	Approved
0.6875	Remote Similarity	NPD6117	Approved
0.6869	Remote Similarity	NPD5369	Approved
0.6863	Remote Similarity	NPD5786	Approved
0.6842	Remote Similarity	NPD6926	Approved
0.6842	Remote Similarity	NPD6924	Approved
0.6837	Remote Similarity	NPD7645	Phase 2
0.6829	Remote Similarity	NPD7507	Approved
0.6804	Remote Similarity	NPD6116	Phase 1
0.68	Remote Similarity	NPD4269	Approved
0.68	Remote Similarity	NPD4270	Approved
0.6789	Remote Similarity	NPD4225	Approved
0.6774	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3698	Phase 2
0.6774	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5368	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