NPASS Compound

Structure

NPC472801 OpenBabel07101718182D 46 51 0 0 1 0 0 0 0 0999 V2000 -3.5640 -1.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6971 -4.4734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9516 -6.0871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8209 -2.8956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2632 -3.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2548 -3.7966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5830 -2.9888 0.0000 C 0 0 0 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5648 -6.2753 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1309 -5.3744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5289 -1.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0263 -5.0899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8237 -2.8209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2604 -3.6472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6915 -4.6229 0.0000 C 0 0 2 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 -4.5620 -6.3501 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6943 -4.5481 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 -5.1254 -5.5238 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 -6.8526 -5.6533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9959 -7.2510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6 10 1 0 0 0 0 6 24 2 0 0 0 0 7 11 2 0 0 0 0 7 24 1 0 0 0 0 8 15 2 0 0 0 0 8 24 1 0 0 0 0 9 13 1 0 0 0 0 9 25 2 0 0 0 0 10 26 2 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 28 1 0 0 0 0 15 33 1 0 0 0 0 16 19 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 17 31 1 0 0 0 0 18 21 1 0 0 0 0 18 32 1 0 0 0 0 19 35 1 0 0 0 0 20 36 1 0 0 0 0 21 37 1 0 0 0 0 22 25 1 0 0 0 0 22 35 1 0 0 0 0 23 38 1 0 0 0 0 23 40 1 0 0 0 0 25 27 1 0 0 0 0 26 41 1 0 0 0 0 27 36 1 6 0 0 0 28 35 1 1 0 0 0 28 37 1 0 0 0 0 29 36 1 6 0 0 0 29 38 1 0 0 0 0 30 37 1 1 0 0 0 30 39 1 0 0 0 0 31 38 1 1 0 0 0 31 42 1 0 0 0 0 32 39 1 1 0 0 0 32 46 1 0 0 0 0 33 43 2 0 0 0 0 33 46 1 0 0 0 0 34 39 1 0 0 0 0 34 44 2 0 0 0 0 34 45 1 0 0 0 0 35 1 1 1 0 0 0 36 2 1 6 0 0 0 37 3 1 1 0 0 0 38 4 1 1 0 0 0 39 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	634.39
Volume:	674.838
LogP:	5.376
LogD:	4.346
LogS:	-4.644
# Rotatable Bonds:	6
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.154
Synthetic Accessibility Score:	5.215
Fsp3:	0.692
Lipinski Rule-of-5:	Rejected
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:	-5.373
MDCK Permeability:	2.0262368707335554e-05
Pgp-inhibitor:	0.172
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.924
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	99.25810241699219%
Volume Distribution (VD):	0.62
Pgp-substrate:	2.604795455932617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.334
CYP2C9-inhibitor:	0.174
CYP2C9-substrate:	0.8
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.263
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	2.294
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.284
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.933
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC472801

Natural Product ID:	NPC472801
*Common Name:**	BCAMKAQICOLQNL-BUSOGWCSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BCAMKAQICOLQNL-BUSOGWCSSA-N
Standard InCHI:	InChI=1S/C39H54O7/c1-35-19-16-30-37(3,21-18-32(39(30,5)34(44)45)46-33(43)15-8-24-6-10-26(41)11-7-24)28(35)14-12-27-25(22-35)9-13-29-36(27,2)20-17-31(42)38(29,4)23-40/h6-11,15,27-32,40-42H,12-14,16-23H2,1-5H3,(H,44,45)/b15-8+/t27-,28-,29+,30+,31+,32-,35-,36+,37+,38+,39+/m0/s1
SMILES:	CC12CCC3C(C1CCC4C(=CCC5C4(CCC(C5(C)CO)O)C)C2)(CCC(C3(C)C(=O)O)OC(=O)C=CC6=CC=C(C=C6)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586196
PubChem CID:	n.a.
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
NPO33505	lycopodiella cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26003344]

☑ 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	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	>	30000.0	nM	PMID[537993]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	>	30000.0	nM	PMID[537993]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	1070.0	nM	PMID[537993]

☑ 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 NPC472801 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	315
0.1-0.2	1251
0.2-0.3	2377
0.3-0.4	4921
0.4-0.5	9354
0.5-0.6	11469
0.6-0.7	11277
0.7-0.8	1594
0.8-0.85	74
0.85-0.9	37
0.9-0.95	26
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9627	High Similarity	NPC22676
0.9627	High Similarity	NPC198621
0.9627	High Similarity	NPC216940
0.9627	High Similarity	NPC475482
0.9624	High Similarity	NPC472804
0.9552	High Similarity	NPC249817
0.9478	High Similarity	NPC173569
0.9478	High Similarity	NPC477874
0.9275	High Similarity	NPC304110
0.9275	High Similarity	NPC27518
0.9185	High Similarity	NPC475457
0.9185	High Similarity	NPC475627
0.9185	High Similarity	NPC475346
0.9185	High Similarity	NPC18982
0.9137	High Similarity	NPC172311
0.913	High Similarity	NPC234548
0.913	High Similarity	NPC248287
0.9078	High Similarity	NPC25491
0.903	High Similarity	NPC86257
0.9007	High Similarity	NPC477873
0.9007	High Similarity	NPC469447
0.8958	High Similarity	NPC325032
0.8958	High Similarity	NPC477483
0.8919	High Similarity	NPC472807
0.8881	High Similarity	NPC53520
0.8872	High Similarity	NPC137416
0.8857	High Similarity	NPC116742
0.8857	High Similarity	NPC139243
0.8841	High Similarity	NPC11266
0.8794	High Similarity	NPC271494
0.8794	High Similarity	NPC470617
0.8794	High Similarity	NPC155192
0.8794	High Similarity	NPC473591
0.8794	High Similarity	NPC470616
0.8723	High Similarity	NPC182249
0.8716	High Similarity	NPC475579
0.8716	High Similarity	NPC473773
0.8705	High Similarity	NPC194970
0.869	High Similarity	NPC8102
0.869	High Similarity	NPC66894
0.8657	High Similarity	NPC265413
0.8657	High Similarity	NPC10154
0.8657	High Similarity	NPC474532
0.8652	High Similarity	NPC471152
0.8649	High Similarity	NPC118033
0.8639	High Similarity	NPC279442
0.8611	High Similarity	NPC235557
0.8581	High Similarity	NPC327962
0.8552	High Similarity	NPC26045
0.8523	High Similarity	NPC473579
0.8523	High Similarity	NPC475454
0.8523	High Similarity	NPC475311
0.8523	High Similarity	NPC473680
0.8514	High Similarity	NPC473719
0.8483	Intermediate Similarity	NPC310621
0.8414	Intermediate Similarity	NPC35212
0.838	Intermediate Similarity	NPC43353
0.8378	Intermediate Similarity	NPC472938
0.8378	Intermediate Similarity	NPC472937
0.8378	Intermediate Similarity	NPC472936
0.8356	Intermediate Similarity	NPC252133
0.8345	Intermediate Similarity	NPC473612
0.8289	Intermediate Similarity	NPC205392
0.8289	Intermediate Similarity	NPC105942
0.8288	Intermediate Similarity	NPC477468
0.8276	Intermediate Similarity	NPC471875
0.8261	Intermediate Similarity	NPC190849
0.8261	Intermediate Similarity	NPC470753
0.8261	Intermediate Similarity	NPC171007
0.8261	Intermediate Similarity	NPC473220
0.8261	Intermediate Similarity	NPC71610
0.8252	Intermediate Similarity	NPC279463
0.825	Intermediate Similarity	NPC472803
0.8247	Intermediate Similarity	NPC469507
0.8243	Intermediate Similarity	NPC307205
0.8235	Intermediate Similarity	NPC478058
0.8214	Intermediate Similarity	NPC131684
0.8212	Intermediate Similarity	NPC87630
0.8212	Intermediate Similarity	NPC208785
0.8212	Intermediate Similarity	NPC116292
0.8212	Intermediate Similarity	NPC472939
0.8212	Intermediate Similarity	NPC35160
0.8212	Intermediate Similarity	NPC162569
0.8212	Intermediate Similarity	NPC145527
0.8212	Intermediate Similarity	NPC179128
0.8212	Intermediate Similarity	NPC470619
0.8212	Intermediate Similarity	NPC470618
0.8212	Intermediate Similarity	NPC267469
0.8188	Intermediate Similarity	NPC275576
0.8188	Intermediate Similarity	NPC470765
0.8188	Intermediate Similarity	NPC320734
0.8176	Intermediate Similarity	NPC477207
0.8158	Intermediate Similarity	NPC140133
0.8153	Intermediate Similarity	NPC266365
0.8146	Intermediate Similarity	NPC477206
0.8143	Intermediate Similarity	NPC469930
0.8129	Intermediate Similarity	NPC169913
0.8121	Intermediate Similarity	NPC169942
0.8112	Intermediate Similarity	NPC476282
0.8112	Intermediate Similarity	NPC203486
0.8108	Intermediate Similarity	NPC204644
0.8108	Intermediate Similarity	NPC477209
0.8105	Intermediate Similarity	NPC48671
0.8099	Intermediate Similarity	NPC18798
0.8092	Intermediate Similarity	NPC247219
0.8085	Intermediate Similarity	NPC288290
0.8075	Intermediate Similarity	NPC471870
0.8074	Intermediate Similarity	NPC42657
0.8054	Intermediate Similarity	NPC474599
0.8052	Intermediate Similarity	NPC474534
0.8052	Intermediate Similarity	NPC474533
0.8043	Intermediate Similarity	NPC198014
0.8042	Intermediate Similarity	NPC165612
0.8039	Intermediate Similarity	NPC261659
0.8027	Intermediate Similarity	NPC295339
0.8027	Intermediate Similarity	NPC79372
0.8026	Intermediate Similarity	NPC264229
0.8026	Intermediate Similarity	NPC253591
0.8026	Intermediate Similarity	NPC146388
0.8026	Intermediate Similarity	NPC46549
0.8014	Intermediate Similarity	NPC477592
0.8014	Intermediate Similarity	NPC118366
0.8013	Intermediate Similarity	NPC470330
0.8013	Intermediate Similarity	NPC477208
0.8	Intermediate Similarity	NPC471935
0.8	Intermediate Similarity	NPC71390
0.8	Intermediate Similarity	NPC471930
0.8	Intermediate Similarity	NPC471929
0.7987	Intermediate Similarity	NPC315772
0.7986	Intermediate Similarity	NPC48929
0.7986	Intermediate Similarity	NPC126516
0.7975	Intermediate Similarity	NPC13989
0.7974	Intermediate Similarity	NPC146014
0.7972	Intermediate Similarity	NPC243305
0.7971	Intermediate Similarity	NPC121168
0.7959	Intermediate Similarity	NPC265335
0.7959	Intermediate Similarity	NPC61590
0.7958	Intermediate Similarity	NPC117899
0.7958	Intermediate Similarity	NPC475138
0.7947	Intermediate Similarity	NPC208293
0.7937	Intermediate Similarity	NPC469395
0.7933	Intermediate Similarity	NPC478164
0.7933	Intermediate Similarity	NPC471876
0.7931	Intermediate Similarity	NPC471864
0.7927	Intermediate Similarity	NPC471871
0.7919	Intermediate Similarity	NPC471444
0.7914	Intermediate Similarity	NPC193698
0.7911	Intermediate Similarity	NPC326084
0.7908	Intermediate Similarity	NPC273358
0.7908	Intermediate Similarity	NPC106524
0.7908	Intermediate Similarity	NPC298647
0.7908	Intermediate Similarity	NPC290695
0.7899	Intermediate Similarity	NPC249340
0.7899	Intermediate Similarity	NPC162935
0.7895	Intermediate Similarity	NPC147250
0.7887	Intermediate Similarity	NPC193203
0.7887	Intermediate Similarity	NPC229894
0.7885	Intermediate Similarity	NPC474622
0.7885	Intermediate Similarity	NPC474621
0.7881	Intermediate Similarity	NPC271607
0.7881	Intermediate Similarity	NPC19862
0.7881	Intermediate Similarity	NPC280717
0.7881	Intermediate Similarity	NPC103910
0.7881	Intermediate Similarity	NPC235195
0.7877	Intermediate Similarity	NPC472372
0.7877	Intermediate Similarity	NPC472374
0.7875	Intermediate Similarity	NPC471873
0.7867	Intermediate Similarity	NPC471971
0.7867	Intermediate Similarity	NPC469855
0.7867	Intermediate Similarity	NPC30846
0.7867	Intermediate Similarity	NPC474300
0.7867	Intermediate Similarity	NPC184935
0.7867	Intermediate Similarity	NPC471972
0.7866	Intermediate Similarity	NPC469772
0.7866	Intermediate Similarity	NPC469776
0.7866	Intermediate Similarity	NPC100925
0.7866	Intermediate Similarity	NPC469778
0.7866	Intermediate Similarity	NPC469774
0.7866	Intermediate Similarity	NPC295941
0.7866	Intermediate Similarity	NPC469777
0.7866	Intermediate Similarity	NPC135334
0.7866	Intermediate Similarity	NPC32723
0.7866	Intermediate Similarity	NPC469773
0.7866	Intermediate Similarity	NPC469775
0.7862	Intermediate Similarity	NPC475449
0.7862	Intermediate Similarity	NPC329913
0.7862	Intermediate Similarity	NPC472591
0.7862	Intermediate Similarity	NPC49742
0.7857	Intermediate Similarity	NPC181334
0.7852	Intermediate Similarity	NPC37992
0.7852	Intermediate Similarity	NPC220496
0.7852	Intermediate Similarity	NPC147542
0.7852	Intermediate Similarity	NPC327916
0.7852	Intermediate Similarity	NPC241349
0.7852	Intermediate Similarity	NPC32749
0.7852	Intermediate Similarity	NPC470035
0.7852	Intermediate Similarity	NPC42262
0.7848	Intermediate Similarity	NPC317580
0.7847	Intermediate Similarity	NPC258073
0.7847	Intermediate Similarity	NPC476847

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 NPC472801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	826
0.2-0.3	1449
0.3-0.4	2593
0.4-0.5	2213
0.5-0.6	1339
0.6-0.7	443
0.7-0.8	23
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8803	High Similarity	NPD8166	Discontinued
0.8099	Intermediate Similarity	NPD6663	Approved
0.8071	Intermediate Similarity	NPD5736	Approved
0.7919	Intermediate Similarity	NPD7003	Approved
0.7895	Intermediate Similarity	NPD6273	Approved
0.7742	Intermediate Similarity	NPD7458	Discontinued
0.7702	Intermediate Similarity	NPD8127	Discontinued
0.7651	Intermediate Similarity	NPD5404	Approved
0.7651	Intermediate Similarity	NPD5406	Approved
0.7651	Intermediate Similarity	NPD5405	Approved
0.7651	Intermediate Similarity	NPD5408	Approved
0.7626	Intermediate Similarity	NPD3019	Approved
0.7626	Intermediate Similarity	NPD2932	Approved
0.7582	Intermediate Similarity	NPD7236	Approved
0.7566	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7768	Phase 2
0.7533	Intermediate Similarity	NPD2935	Discontinued
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD8032	Phase 2
0.7467	Intermediate Similarity	NPD2799	Discontinued
0.7451	Intermediate Similarity	NPD4628	Phase 3
0.7432	Intermediate Similarity	NPD4140	Approved
0.7415	Intermediate Similarity	NPD3764	Approved
0.7372	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3091	Approved
0.7347	Intermediate Similarity	NPD7008	Discontinued
0.7342	Intermediate Similarity	NPD7239	Suspended
0.7329	Intermediate Similarity	NPD7819	Suspended
0.731	Intermediate Similarity	NPD8313	Approved
0.731	Intermediate Similarity	NPD2797	Approved
0.731	Intermediate Similarity	NPD8312	Approved
0.7285	Intermediate Similarity	NPD7097	Phase 1
0.7284	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8150	Discontinued
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7246	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1283	Approved
0.723	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3750	Approved
0.7214	Intermediate Similarity	NPD9493	Approved
0.7203	Intermediate Similarity	NPD3023	Approved
0.7203	Intermediate Similarity	NPD3026	Approved
0.72	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2629	Approved
0.7192	Intermediate Similarity	NPD3094	Phase 2
0.7192	Intermediate Similarity	NPD1470	Approved
0.7192	Intermediate Similarity	NPD1164	Approved
0.7183	Intermediate Similarity	NPD3025	Approved
0.7183	Intermediate Similarity	NPD3024	Approved
0.7181	Intermediate Similarity	NPD6798	Discontinued
0.7181	Intermediate Similarity	NPD3268	Approved
0.7179	Intermediate Similarity	NPD6190	Approved
0.7179	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3092	Approved
0.7153	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7133	Intermediate Similarity	NPD3095	Discontinued
0.7133	Intermediate Similarity	NPD4626	Approved
0.7126	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD8455	Phase 2
0.7115	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4110	Phase 3
0.7114	Intermediate Similarity	NPD7095	Approved
0.7113	Intermediate Similarity	NPD9545	Approved
0.7099	Intermediate Similarity	NPD7411	Suspended
0.7097	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7075	Discontinued
0.7089	Intermediate Similarity	NPD7390	Discontinued
0.7086	Intermediate Similarity	NPD2979	Phase 3
0.7086	Intermediate Similarity	NPD4060	Phase 1
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7078	Intermediate Similarity	NPD2438	Suspended
0.7071	Intermediate Similarity	NPD5951	Approved
0.7066	Intermediate Similarity	NPD6959	Discontinued
0.7063	Intermediate Similarity	NPD5691	Approved
0.7059	Intermediate Similarity	NPD7228	Approved
0.7055	Intermediate Similarity	NPD37	Approved
0.705	Intermediate Similarity	NPD6858	Approved
0.705	Intermediate Similarity	NPD7094	Approved
0.7047	Intermediate Similarity	NPD6832	Phase 2
0.7044	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4380	Phase 2
0.7034	Intermediate Similarity	NPD1281	Approved
0.703	Intermediate Similarity	NPD4965	Approved
0.703	Intermediate Similarity	NPD4966	Approved
0.703	Intermediate Similarity	NPD4967	Phase 2
0.7027	Intermediate Similarity	NPD2798	Approved
0.702	Intermediate Similarity	NPD6233	Phase 2
0.7018	Intermediate Similarity	NPD5844	Phase 1
0.7014	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7033	Discontinued
0.7013	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD6010	Discontinued
0.6994	Remote Similarity	NPD6677	Suspended
0.6975	Remote Similarity	NPD3226	Approved
0.6968	Remote Similarity	NPD4477	Approved
0.6968	Remote Similarity	NPD6100	Approved
0.6968	Remote Similarity	NPD4476	Approved
0.6968	Remote Similarity	NPD6099	Approved
0.6959	Remote Similarity	NPD1203	Approved
0.6959	Remote Similarity	NPD7799	Discontinued
0.6954	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2313	Discontinued
0.6946	Remote Similarity	NPD6234	Discontinued
0.6939	Remote Similarity	NPD5327	Phase 3
0.6937	Remote Similarity	NPD2534	Approved
0.6937	Remote Similarity	NPD2533	Approved
0.6937	Remote Similarity	NPD2532	Approved
0.6933	Remote Similarity	NPD7028	Phase 2
0.6933	Remote Similarity	NPD6599	Discontinued
0.6928	Remote Similarity	NPD7057	Phase 3
0.6928	Remote Similarity	NPD7058	Phase 2
0.6928	Remote Similarity	NPD5735	Approved
0.6923	Remote Similarity	NPD6232	Discontinued
0.6909	Remote Similarity	NPD5760	Phase 2
0.6909	Remote Similarity	NPD5761	Phase 2
0.6908	Remote Similarity	NPD7961	Discontinued
0.6903	Remote Similarity	NPD3748	Approved
0.6903	Remote Similarity	NPD1510	Phase 2
0.6903	Remote Similarity	NPD4308	Phase 3
0.6901	Remote Similarity	NPD4198	Discontinued
0.6899	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3400	Discontinued
0.6879	Remote Similarity	NPD1549	Phase 2
0.6875	Remote Similarity	NPD7741	Discontinued
0.6871	Remote Similarity	NPD9717	Approved
0.6871	Remote Similarity	NPD3972	Approved
0.6863	Remote Similarity	NPD3620	Phase 2
0.6863	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1551	Phase 2
0.6859	Remote Similarity	NPD2531	Phase 2
0.6853	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7427	Discontinued
0.6849	Remote Similarity	NPD3496	Discontinued
0.6848	Remote Similarity	NPD6801	Discontinued
0.6846	Remote Similarity	NPD3266	Approved
0.6846	Remote Similarity	NPD3267	Approved
0.6842	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5909	Discontinued
0.6832	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5585	Approved
0.6828	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1651	Approved
0.6826	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4908	Phase 1
0.6818	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5124	Phase 1
0.6815	Remote Similarity	NPD6002	Phase 3
0.6815	Remote Similarity	NPD6005	Phase 3
0.6815	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5763	Approved
0.6815	Remote Similarity	NPD6004	Phase 3
0.6815	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5762	Approved
0.6815	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5647	Approved
0.6797	Remote Similarity	NPD7715	Approved
0.6797	Remote Similarity	NPD7714	Approved
0.6791	Remote Similarity	NPD3020	Approved
0.6791	Remote Similarity	NPD8320	Phase 1
0.6791	Remote Similarity	NPD8319	Approved
0.6786	Remote Similarity	NPD3749	Approved
0.6786	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1778	Approved
0.6781	Remote Similarity	NPD4059	Approved
0.6781	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6353	Approved
0.6774	Remote Similarity	NPD6653	Approved
0.6774	Remote Similarity	NPD1607	Approved
0.6772	Remote Similarity	NPD4534	Discontinued
0.677	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6647	Phase 2
0.6763	Remote Similarity	NPD74	Approved
0.6763	Remote Similarity	NPD9266	Approved
0.6761	Remote Similarity	NPD1241	Discontinued
0.6761	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1894	Discontinued
0.6757	Remote Similarity	NPD1608	Approved
0.6753	Remote Similarity	NPD1240	Approved
0.6752	Remote Similarity	NPD2796	Approved
0.6748	Remote Similarity	NPD5403	Approved
0.6744	Remote Similarity	NPD6168	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