NPASS Compound

Structure

NPC101462 OpenBabel07101719522D 34 37 0 0 1 0 0 0 0 0999 V2000 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 3.0032 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 -2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1871 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9000 3.9543 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 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 -4.3301 -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 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 1 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 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2308 4.6974 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 -5.1962 -2.0000 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 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 25 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 30 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 28 1 0 0 0 0 17 31 1 0 0 0 0 19 3 1 1 0 0 0 19 21 1 0 0 0 0 20 32 1 1 0 0 0 21 29 1 1 0 0 0 22 23 1 0 0 0 0 22 27 1 1 0 0 0 23 28 1 0 0 0 0 24 26 1 0 0 0 0 24 33 1 1 0 0 0 25 28 1 1 0 0 0 25 34 1 0 0 0 0 26 27 1 6 0 0 0 26 30 1 0 0 0 0 27 4 1 1 0 0 0 28 5 1 6 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	523.098
LogP:	5.01
LogD:	4.041
LogS:	-4.351
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	5.323
Fsp3:	0.867
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:	-4.951
MDCK Permeability:	6.6849702307081316e-06
Pgp-inhibitor:	0.992
Pgp-substrate:	0.537
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.373
30% Bioavailability (F30%):	0.189

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	87.01998901367188%
Volume Distribution (VD):	1.095
Pgp-substrate:	3.634666919708252%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.295
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.884
CYP3A4-substrate:	0.635

ADMET: Excretion

Clearance (CL):	6.291
Half-life (T1/2):	0.128

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.72
Maximum Recommended Daily Dose:	0.166
Skin Sensitization:	0.204
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC101462

Natural Product ID:	NPC101462
*Common Name:**	Balsaminol A
IUPAC Name:	(3S,4S,7S,8R,9S,10S,13R,14S,17R)-4-(hydroxymethyl)-17-[(2R,4R)-4-hydroxy-6-methylhept-5-en-2-yl]-4,9,13,14-tetramethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Synonyms:
Standard InCHIKey:	AVFNYXHRDYAHNF-HEVJPHJFSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-18(2)14-20(32)15-19(3)21-10-11-30(7)26-24(33)16-23-22(8-9-25(34)28(23,5)17-31)27(26,4)12-13-29(21,30)6/h14,16,19-22,24-26,31-34H,8-13,15,17H2,1-7H3/t19-,20+,21-,22-,24+,25+,26-,27+,28-,29-,30+/m1/s1
SMILES:	CC(=C[C@@H](C[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3[C@H](C=C4[C@@H](CC[C@@H]([C@]4(C)CO)O)[C@]3(C)CC[C@]12C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078436
PubChem CID:	44607276
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	African	n.a.	PMID[19795842]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20541427]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31339732]
NPO22328	Momordica balsamina	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6
Others	11

Activity Type	# Activity
Cell Line	2
Individual Protein	9
NON-MOLECULAR	2
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	40000.0	nM	PMID[573961]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	40000.0	nM	PMID[573962]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	23500.0	nM	PMID[573962]
NPT2	Others	Unspecified		Selectivity Index	=	2.3	n.a.	PMID[573962]
NPT2	Others	Unspecified		Selectivity Index	=	1.7	n.a.	PMID[573962]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	17100.0	nM	PMID[573962]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12600.0	nM	PMID[573963]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7200.0	nM	PMID[573963]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	47.6	n.a.	PMID[573963]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	1.5	n.a.	PMID[573963]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	766.1	n.a.	PMID[573963]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Flu intensity	=	20.1	n.a.	PMID[573963]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	260.0	n.a.	PMID[573963]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	259.0	n.a.	PMID[573963]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	454.5	n.a.	PMID[573963]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	432.9	n.a.	PMID[573963]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	CI	=	0.503	n.a.	PMID[573963]

☑ 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 NPC101462 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	152
0.1-0.2	1298
0.2-0.3	4959
0.3-0.4	15114
0.4-0.5	8818
0.5-0.6	5876
0.6-0.7	4589
0.7-0.8	1483
0.8-0.85	247
0.85-0.9	95
0.9-0.95	54
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC205845
0.9744	High Similarity	NPC185568
0.962	High Similarity	NPC266511
0.9605	High Similarity	NPC143182
0.9605	High Similarity	NPC84694
0.9605	High Similarity	NPC109546
0.9605	High Similarity	NPC28862
0.9605	High Similarity	NPC47982
0.9605	High Similarity	NPC81306
0.95	High Similarity	NPC6391
0.9487	High Similarity	NPC49964
0.9481	High Similarity	NPC234193
0.9474	High Similarity	NPC474216
0.9383	High Similarity	NPC149224
0.9367	High Similarity	NPC474634
0.9359	High Similarity	NPC209620
0.9359	High Similarity	NPC23852
0.9359	High Similarity	NPC264245
0.9351	High Similarity	NPC30986
0.9351	High Similarity	NPC209430
0.9259	High Similarity	NPC152808
0.9259	High Similarity	NPC261266
0.9259	High Similarity	NPC293287
0.9241	High Similarity	NPC189972
0.9241	High Similarity	NPC50964
0.9231	High Similarity	NPC241290
0.9231	High Similarity	NPC209944
0.9231	High Similarity	NPC164840
0.9221	High Similarity	NPC473943
0.9211	High Similarity	NPC240604
0.9211	High Similarity	NPC321016
0.9211	High Similarity	NPC244488
0.9211	High Similarity	NPC247325
0.9211	High Similarity	NPC300324
0.9211	High Similarity	NPC107059
0.9211	High Similarity	NPC321381
0.9136	High Similarity	NPC274448
0.9125	High Similarity	NPC317458
0.9125	High Similarity	NPC475789
0.9114	High Similarity	NPC470383
0.9114	High Similarity	NPC474752
0.9114	High Similarity	NPC474759
0.9114	High Similarity	NPC474731
0.9114	High Similarity	NPC474683
0.9114	High Similarity	NPC47761
0.9114	High Similarity	NPC82986
0.9114	High Similarity	NPC7505
0.9091	High Similarity	NPC198968
0.9091	High Similarity	NPC318495
0.9091	High Similarity	NPC155986
0.9079	High Similarity	NPC162742
0.9079	High Similarity	NPC136188
0.9079	High Similarity	NPC134847
0.9079	High Similarity	NPC285893
0.9079	High Similarity	NPC22105
0.9079	High Similarity	NPC230301
0.9079	High Similarity	NPC304309
0.9079	High Similarity	NPC28657
0.9079	High Similarity	NPC288035
0.9036	High Similarity	NPC67872
0.9	High Similarity	NPC296701
0.9	High Similarity	NPC30166
0.9	High Similarity	NPC470049
0.9	High Similarity	NPC87489
0.9	High Similarity	NPC218616
0.9	High Similarity	NPC202389
0.8974	High Similarity	NPC87604
0.8974	High Similarity	NPC477522
0.8974	High Similarity	NPC275910
0.8961	High Similarity	NPC113733
0.8961	High Similarity	NPC189883
0.8941	High Similarity	NPC97404
0.8941	High Similarity	NPC41554
0.8929	High Similarity	NPC470361
0.8916	High Similarity	NPC470620
0.8902	High Similarity	NPC318390
0.8902	High Similarity	NPC157257
0.8902	High Similarity	NPC470360
0.8889	High Similarity	NPC470384
0.8875	High Similarity	NPC474531
0.8861	High Similarity	NPC1319
0.8861	High Similarity	NPC328714
0.8846	High Similarity	NPC34019
0.8846	High Similarity	NPC91594
0.8846	High Similarity	NPC214570
0.8831	High Similarity	NPC141071
0.8831	High Similarity	NPC471723
0.8831	High Similarity	NPC257347
0.8824	High Similarity	NPC3345
0.8824	High Similarity	NPC80561
0.8824	High Similarity	NPC329596
0.8824	High Similarity	NPC295668
0.8824	High Similarity	NPC11216
0.8824	High Similarity	NPC204188
0.8824	High Similarity	NPC291484
0.881	High Similarity	NPC474668
0.8795	High Similarity	NPC299068
0.878	High Similarity	NPC238485
0.878	High Similarity	NPC231310
0.878	High Similarity	NPC124172
0.878	High Similarity	NPC474047
0.878	High Similarity	NPC470077
0.8765	High Similarity	NPC470614
0.8765	High Similarity	NPC1272
0.875	High Similarity	NPC102253
0.875	High Similarity	NPC26117
0.875	High Similarity	NPC322313
0.875	High Similarity	NPC236112
0.875	High Similarity	NPC236237
0.8734	High Similarity	NPC477514
0.8734	High Similarity	NPC307965
0.8734	High Similarity	NPC18603
0.8734	High Similarity	NPC167037
0.8734	High Similarity	NPC83351
0.8734	High Similarity	NPC285761
0.8734	High Similarity	NPC76931
0.8734	High Similarity	NPC167891
0.8734	High Similarity	NPC244385
0.8734	High Similarity	NPC6978
0.8734	High Similarity	NPC138621
0.8718	High Similarity	NPC96319
0.8718	High Similarity	NPC73875
0.8718	High Similarity	NPC46160
0.8718	High Similarity	NPC237460
0.8718	High Similarity	NPC134330
0.8718	High Similarity	NPC129165
0.8718	High Similarity	NPC202642
0.8706	High Similarity	NPC146554
0.8706	High Similarity	NPC477606
0.8701	High Similarity	NPC471797
0.8701	High Similarity	NPC469534
0.8701	High Similarity	NPC469533
0.8701	High Similarity	NPC469593
0.869	High Similarity	NPC475313
0.8659	High Similarity	NPC82623
0.8642	High Similarity	NPC476646
0.8625	High Similarity	NPC80530
0.8625	High Similarity	NPC273410
0.8608	High Similarity	NPC477924
0.8608	High Similarity	NPC470711
0.8608	High Similarity	NPC470758
0.8605	High Similarity	NPC48010
0.859	High Similarity	NPC322353
0.859	High Similarity	NPC185536
0.859	High Similarity	NPC118508
0.859	High Similarity	NPC121744
0.8588	High Similarity	NPC471952
0.8588	High Similarity	NPC133588
0.8571	High Similarity	NPC474970
0.8571	High Similarity	NPC474140
0.8571	High Similarity	NPC471799
0.8571	High Similarity	NPC24277
0.8571	High Similarity	NPC139724
0.8554	High Similarity	NPC209802
0.8554	High Similarity	NPC478102
0.8553	High Similarity	NPC34834
0.8539	High Similarity	NPC288970
0.8537	High Similarity	NPC248886
0.8537	High Similarity	NPC201852
0.8537	High Similarity	NPC5985
0.8523	High Similarity	NPC292793
0.8523	High Similarity	NPC477605
0.8519	High Similarity	NPC96362
0.8519	High Similarity	NPC295131
0.8519	High Similarity	NPC13554
0.85	High Similarity	NPC476314
0.85	High Similarity	NPC302041
0.85	High Similarity	NPC205455
0.85	High Similarity	NPC301707
0.85	High Similarity	NPC11908
0.85	High Similarity	NPC85346
0.85	High Similarity	NPC65897
0.85	High Similarity	NPC186191
0.8488	Intermediate Similarity	NPC262858
0.8488	Intermediate Similarity	NPC1015
0.8488	Intermediate Similarity	NPC472240
0.8488	Intermediate Similarity	NPC31985
0.8481	Intermediate Similarity	NPC265588
0.8481	Intermediate Similarity	NPC470362
0.8481	Intermediate Similarity	NPC470749
0.8462	Intermediate Similarity	NPC243342
0.8462	Intermediate Similarity	NPC201048
0.8462	Intermediate Similarity	NPC477138
0.8462	Intermediate Similarity	NPC91858
0.8462	Intermediate Similarity	NPC476366
0.8452	Intermediate Similarity	NPC474349
0.8452	Intermediate Similarity	NPC471224
0.8452	Intermediate Similarity	NPC474189
0.8434	Intermediate Similarity	NPC134481
0.8434	Intermediate Similarity	NPC470558
0.8434	Intermediate Similarity	NPC113978
0.8434	Intermediate Similarity	NPC207013
0.8434	Intermediate Similarity	NPC110778
0.8415	Intermediate Similarity	NPC157655
0.8415	Intermediate Similarity	NPC320525
0.8415	Intermediate Similarity	NPC249423
0.8409	Intermediate Similarity	NPC310013
0.8395	Intermediate Similarity	NPC472463
0.8395	Intermediate Similarity	NPC53744
0.8391	Intermediate Similarity	NPC192437

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 NPC101462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1480
0.2-0.3	4163
0.3-0.4	2367
0.4-0.5	539
0.5-0.6	181
0.6-0.7	176
0.7-0.8	76
0.8-0.85	22
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9079	High Similarity	NPD7339	Approved
0.9079	High Similarity	NPD6942	Approved
0.875	High Similarity	NPD7525	Registered
0.8718	High Similarity	NPD3701	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD6929	Approved
0.8333	Intermediate Similarity	NPD4786	Approved
0.8293	Intermediate Similarity	NPD6931	Approved
0.8293	Intermediate Similarity	NPD6930	Phase 2
0.8228	Intermediate Similarity	NPD6926	Approved
0.8228	Intermediate Similarity	NPD6924	Approved
0.8214	Intermediate Similarity	NPD6695	Phase 3
0.8171	Intermediate Similarity	NPD7645	Phase 2
0.8148	Intermediate Similarity	NPD5776	Phase 2
0.8148	Intermediate Similarity	NPD6925	Approved
0.8118	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD3667	Approved
0.8072	Intermediate Similarity	NPD7514	Phase 3
0.8049	Intermediate Similarity	NPD7145	Approved
0.8025	Intermediate Similarity	NPD6933	Approved
0.8	Intermediate Similarity	NPD4785	Approved
0.8	Intermediate Similarity	NPD4784	Approved
0.7976	Intermediate Similarity	NPD6902	Approved
0.7975	Intermediate Similarity	NPD7150	Approved
0.7975	Intermediate Similarity	NPD4243	Approved
0.7975	Intermediate Similarity	NPD7151	Approved
0.7975	Intermediate Similarity	NPD7152	Approved
0.7949	Intermediate Similarity	NPD6923	Approved
0.7949	Intermediate Similarity	NPD6922	Approved
0.7865	Intermediate Similarity	NPD5328	Approved
0.7857	Intermediate Similarity	NPD7332	Phase 2
0.7848	Intermediate Similarity	NPD7143	Approved
0.7848	Intermediate Similarity	NPD7144	Approved
0.7841	Intermediate Similarity	NPD7524	Approved
0.7841	Intermediate Similarity	NPD7750	Discontinued
0.7831	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6893	Approved
0.7727	Intermediate Similarity	NPD3618	Phase 1
0.7711	Intermediate Similarity	NPD6932	Approved
0.7692	Intermediate Similarity	NPD6079	Approved
0.7683	Intermediate Similarity	NPD8264	Approved
0.7647	Intermediate Similarity	NPD4748	Discontinued
0.7609	Intermediate Similarity	NPD6399	Phase 3
0.7558	Intermediate Similarity	NPD6898	Phase 1
0.7529	Intermediate Similarity	NPD6683	Phase 2
0.7526	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD7087	Discontinued
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7474	Intermediate Similarity	NPD4755	Approved
0.7473	Intermediate Similarity	NPD4753	Phase 2
0.747	Intermediate Similarity	NPD4190	Phase 3
0.747	Intermediate Similarity	NPD5275	Approved
0.7442	Intermediate Similarity	NPD7509	Discontinued
0.7419	Intermediate Similarity	NPD4202	Approved
0.7396	Intermediate Similarity	NPD7638	Approved
0.7374	Intermediate Similarity	NPD5141	Approved
0.7368	Intermediate Similarity	NPD4697	Phase 3
0.7368	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5221	Approved
0.7368	Intermediate Similarity	NPD5222	Approved
0.7326	Intermediate Similarity	NPD4195	Approved
0.732	Intermediate Similarity	NPD4700	Approved
0.732	Intermediate Similarity	NPD5285	Approved
0.732	Intermediate Similarity	NPD5286	Approved
0.732	Intermediate Similarity	NPD4696	Approved
0.7312	Intermediate Similarity	NPD7637	Suspended
0.7292	Intermediate Similarity	NPD5173	Approved
0.7284	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6051	Approved
0.7222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4633	Approved
0.7172	Intermediate Similarity	NPD5226	Approved
0.7172	Intermediate Similarity	NPD5225	Approved
0.7172	Intermediate Similarity	NPD5224	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7129	Intermediate Similarity	NPD5739	Approved
0.7129	Intermediate Similarity	NPD6675	Approved
0.7129	Intermediate Similarity	NPD6402	Approved
0.7129	Intermediate Similarity	NPD7128	Approved
0.7128	Intermediate Similarity	NPD7515	Phase 2
0.7113	Intermediate Similarity	NPD6083	Phase 2
0.7113	Intermediate Similarity	NPD6084	Phase 2
0.7103	Intermediate Similarity	NPD7115	Discovery
0.71	Intermediate Similarity	NPD5175	Approved
0.71	Intermediate Similarity	NPD5174	Approved
0.7083	Intermediate Similarity	NPD5210	Approved
0.7083	Intermediate Similarity	NPD4629	Approved
0.7079	Intermediate Similarity	NPD4223	Phase 3
0.7079	Intermediate Similarity	NPD4221	Approved
0.7071	Intermediate Similarity	NPD5223	Approved
0.7051	Intermediate Similarity	NPD368	Approved
0.7041	Intermediate Similarity	NPD4225	Approved
0.7033	Intermediate Similarity	NPD5329	Approved
0.7021	Intermediate Similarity	NPD7136	Phase 2
0.699	Remote Similarity	NPD7320	Approved
0.699	Remote Similarity	NPD6881	Approved
0.699	Remote Similarity	NPD6899	Approved
0.6961	Remote Similarity	NPD4768	Approved
0.6961	Remote Similarity	NPD4767	Approved
0.6931	Remote Similarity	NPD4754	Approved
0.6923	Remote Similarity	NPD4197	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD6373	Approved
0.69	Remote Similarity	NPD4159	Approved
0.6893	Remote Similarity	NPD5701	Approved
0.6893	Remote Similarity	NPD5697	Approved
0.6869	Remote Similarity	NPD5290	Discontinued
0.6857	Remote Similarity	NPD7102	Approved
0.6857	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD7290	Approved
0.6832	Remote Similarity	NPD7632	Discontinued
0.6827	Remote Similarity	NPD5128	Approved
0.6827	Remote Similarity	NPD4729	Approved
0.6827	Remote Similarity	NPD4730	Approved
0.6818	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4788	Approved
0.6809	Remote Similarity	NPD6672	Approved
0.6809	Remote Similarity	NPD5737	Approved
0.6804	Remote Similarity	NPD7748	Approved
0.6792	Remote Similarity	NPD6847	Approved
0.6792	Remote Similarity	NPD6617	Approved
0.6792	Remote Similarity	NPD6650	Approved
0.6792	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD8130	Phase 1
0.6792	Remote Similarity	NPD6649	Approved
0.6774	Remote Similarity	NPD4138	Approved
0.6774	Remote Similarity	NPD6409	Approved
0.6774	Remote Similarity	NPD4688	Approved
0.6774	Remote Similarity	NPD6684	Approved
0.6774	Remote Similarity	NPD5330	Approved
0.6774	Remote Similarity	NPD7521	Approved
0.6774	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4519	Discontinued
0.6774	Remote Similarity	NPD7146	Approved
0.6774	Remote Similarity	NPD4623	Approved
0.6774	Remote Similarity	NPD4690	Approved
0.6774	Remote Similarity	NPD5205	Approved
0.6774	Remote Similarity	NPD4693	Phase 3
0.6774	Remote Similarity	NPD4689	Approved
0.6774	Remote Similarity	NPD7334	Approved
0.6771	Remote Similarity	NPD8034	Phase 2
0.6771	Remote Similarity	NPD8035	Phase 2
0.6762	Remote Similarity	NPD6014	Approved
0.6762	Remote Similarity	NPD6013	Approved
0.6762	Remote Similarity	NPD6012	Approved
0.6735	Remote Similarity	NPD5695	Phase 3
0.6729	Remote Similarity	NPD8297	Approved
0.6729	Remote Similarity	NPD6882	Approved
0.6711	Remote Similarity	NPD342	Phase 1
0.67	Remote Similarity	NPD5696	Approved
0.6698	Remote Similarity	NPD5251	Approved
0.6698	Remote Similarity	NPD5249	Phase 3
0.6698	Remote Similarity	NPD4634	Approved
0.6698	Remote Similarity	NPD5247	Approved
0.6698	Remote Similarity	NPD5250	Approved
0.6698	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD5216	Approved
0.6636	Remote Similarity	NPD5217	Approved
0.6636	Remote Similarity	NPD5215	Approved
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4723	Approved
0.6632	Remote Similarity	NPD6903	Approved
0.6632	Remote Similarity	NPD4722	Approved
0.6632	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5331	Approved
0.663	Remote Similarity	NPD5332	Approved
0.663	Remote Similarity	NPD5362	Discontinued
0.6629	Remote Similarity	NPD4268	Approved
0.6629	Remote Similarity	NPD3617	Approved
0.6629	Remote Similarity	NPD4271	Approved
0.66	Remote Similarity	NPD7902	Approved
0.6596	Remote Similarity	NPD5280	Approved
0.6596	Remote Similarity	NPD5690	Phase 2
0.6596	Remote Similarity	NPD4694	Approved
0.6593	Remote Similarity	NPD4790	Discontinued
0.6591	Remote Similarity	NPD6117	Approved
0.6588	Remote Similarity	NPD4787	Phase 1
0.6577	Remote Similarity	NPD7328	Approved
0.6577	Remote Similarity	NPD7327	Approved
0.6571	Remote Similarity	NPD6412	Phase 2
0.6559	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8033	Approved
0.6542	Remote Similarity	NPD5169	Approved
0.6542	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5135	Approved
0.6518	Remote Similarity	NPD7516	Approved
0.6517	Remote Similarity	NPD6116	Phase 1
0.6512	Remote Similarity	NPD4809	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