NPASS Compound

Structure

NPC472803 OpenBabel07101718182D 47 52 0 0 1 0 0 0 0 0999 V2000 -5.8833 4.8715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4379 6.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1642 2.4010 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 -2.6971 4.4734 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 3.4641 5.0000 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 3.4641 3.0000 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 -2.2632 3.7219 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 1.7321 2.0000 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 -3.5289 1.8653 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 3.0000 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 -1.7321 2.0000 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 -3.2604 3.6472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6915 4.6229 0.0000 C 0 0 1 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 -4.8209 2.8956 0.0000 C 0 0 1 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 -5.1254 5.5238 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 -0.8660 1.5000 0.0000 C 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8237 2.8209 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -5.3842 2.0694 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 -2.8928 3.1863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 1 33 1 0 0 0 0 2 33 1 0 0 0 0 7 46 1 0 0 0 0 8 9 2 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 26 1 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 16 1 0 0 0 0 13 28 1 0 0 0 0 14 17 1 0 0 0 0 14 30 1 0 0 0 0 15 34 1 0 0 0 0 16 36 1 0 0 0 0 17 35 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 27 1 0 0 0 0 19 29 1 0 0 0 0 20 34 1 0 0 0 0 20 38 1 0 0 0 0 21 31 1 0 0 0 0 22 23 2 0 0 0 0 22 39 1 0 0 0 0 23 46 1 0 0 0 0 24 34 1 6 0 0 0 24 35 1 0 0 0 0 25 35 1 6 0 0 0 25 37 1 0 0 0 0 26 36 1 1 0 0 0 26 38 1 0 0 0 0 27 33 1 0 0 0 0 27 36 1 1 0 0 0 28 33 1 0 0 0 0 28 40 1 6 0 0 0 29 38 1 1 0 0 0 29 41 1 0 0 0 0 30 37 1 6 0 0 0 30 47 1 0 0 0 0 31 42 2 0 0 0 0 31 47 1 0 0 0 0 32 37 1 0 0 0 0 32 43 2 0 0 0 0 32 44 1 0 0 0 0 34 3 1 6 0 0 0 35 4 1 6 0 0 0 36 5 1 1 0 0 0 37 6 1 1 0 0 0 38 45 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.39
Volume:	680.395
LogP:	4.282
LogD:	3.433
LogS:	-4.281
# Rotatable Bonds:	5
TPSA:	153.75
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.248
Synthetic Accessibility Score:	5.261
Fsp3:	0.789
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.323
MDCK Permeability:	1.4772405847907066e-05
Pgp-inhibitor:	0.939
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.692

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	98.16835021972656%
Volume Distribution (VD):	0.314
Pgp-substrate:	6.183067321777344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.213
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.319
CYP2C9-inhibitor:	0.137
CYP2C9-substrate:	0.649
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.232
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	2.634
Half-life (T1/2):	0.514

ADMET: Toxicity

hERG Blockers:	0.403
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.603
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.836
Carcinogencity:	0.015
Eye Corrosion:	0.004
Eye Irritation:	0.315
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: NPC472803

Natural Product ID:	NPC472803
*Common Name:**	NBJOSEVZMRGBSS-WNRWCFFQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NBJOSEVZMRGBSS-WNRWCFFQSA-N
Standard InCHI:	InChI=1S/C38H56O9/c1-33(2)27-19-29(41)38(45)20-34(3)15-12-25-35(4,24(34)10-11-26(38)36(27,5)16-13-28(33)40)17-14-30(37(25,6)32(43)44)47-31(42)21-8-9-23(46-7)22(39)18-21/h8-9,18,24-30,39-41,45H,10-17,19-20H2,1-7H3,(H,43,44)/t24-,25+,26+,27-,28+,29-,30-,34-,35+,36+,37+,38+/m0/s1
SMILES:	COc1ccc(cc1O)C(=O)O[C@H]1CC[C@]2([C@H]([C@@]1(C)C(=O)O)CC[C@@]1([C@@H]2CC[C@H]2[C@@](C1)(O)[C@@H](O)C[C@@H]1[C@]2(C)CC[C@H](C1(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586198
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	=	9980.0	nM	PMID[479521]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	>	30000.0	nM	PMID[479521]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	980.0	nM	PMID[479521]

☑ 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 NPC472803 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	418
0.1-0.2	1546
0.2-0.3	3122
0.3-0.4	6195
0.4-0.5	9465
0.5-0.6	7816
0.6-0.7	7756
0.7-0.8	6082
0.8-0.85	236
0.85-0.9	53
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9329	High Similarity	NPC266545
0.9329	High Similarity	NPC202428
0.9325	High Similarity	NPC200726
0.9268	High Similarity	NPC177362
0.9245	High Similarity	NPC472807
0.8963	High Similarity	NPC266365
0.8944	High Similarity	NPC62051
0.8938	High Similarity	NPC475579
0.8938	High Similarity	NPC473773
0.8875	High Similarity	NPC118033
0.882	High Similarity	NPC124842
0.8758	High Similarity	NPC473680
0.8758	High Similarity	NPC473579
0.8758	High Similarity	NPC475311
0.8758	High Similarity	NPC475454
0.8743	High Similarity	NPC100420
0.8696	High Similarity	NPC327962
0.8667	High Similarity	NPC268602
0.8655	High Similarity	NPC469776
0.8655	High Similarity	NPC135334
0.8655	High Similarity	NPC469774
0.8655	High Similarity	NPC295941
0.8655	High Similarity	NPC469777
0.8655	High Similarity	NPC469772
0.8655	High Similarity	NPC469773
0.8655	High Similarity	NPC32723
0.8655	High Similarity	NPC469775
0.8655	High Similarity	NPC100925
0.8655	High Similarity	NPC469778
0.865	High Similarity	NPC205392
0.865	High Similarity	NPC105942
0.8631	High Similarity	NPC45943
0.8616	High Similarity	NPC469683
0.8603	High Similarity	NPC475299
0.8598	High Similarity	NPC469888
0.8589	High Similarity	NPC267091
0.8571	High Similarity	NPC477483
0.8571	High Similarity	NPC325032
0.8571	High Similarity	NPC188217
0.8563	High Similarity	NPC472055
0.8563	High Similarity	NPC185617
0.8555	High Similarity	NPC469354
0.8555	High Similarity	NPC294149
0.8555	High Similarity	NPC469438
0.8553	High Similarity	NPC469615
0.8531	High Similarity	NPC96194
0.8531	High Similarity	NPC299855
0.8529	High Similarity	NPC263212
0.8528	High Similarity	NPC243891
0.8528	High Similarity	NPC119252
0.8512	High Similarity	NPC216916
0.8506	High Similarity	NPC478050
0.8503	High Similarity	NPC470339
0.85	High Similarity	NPC307205
0.8497	Intermediate Similarity	NPC316539
0.8497	Intermediate Similarity	NPC98583
0.8494	Intermediate Similarity	NPC470896
0.8494	Intermediate Similarity	NPC471968
0.8494	Intermediate Similarity	NPC473275
0.8488	Intermediate Similarity	NPC180768
0.8488	Intermediate Similarity	NPC476365
0.8485	Intermediate Similarity	NPC305710
0.8483	Intermediate Similarity	NPC189704
0.8476	Intermediate Similarity	NPC48671
0.8471	Intermediate Similarity	NPC471788
0.8466	Intermediate Similarity	NPC145527
0.8466	Intermediate Similarity	NPC470619
0.8466	Intermediate Similarity	NPC208785
0.8466	Intermediate Similarity	NPC470618
0.8462	Intermediate Similarity	NPC476372
0.8462	Intermediate Similarity	NPC476371
0.8457	Intermediate Similarity	NPC469418
0.8457	Intermediate Similarity	NPC472969
0.8452	Intermediate Similarity	NPC476373
0.8452	Intermediate Similarity	NPC24627
0.8447	Intermediate Similarity	NPC75295
0.8439	Intermediate Similarity	NPC472620
0.8439	Intermediate Similarity	NPC100251
0.8439	Intermediate Similarity	NPC65333
0.8438	Intermediate Similarity	NPC25491
0.8436	Intermediate Similarity	NPC475121
0.8436	Intermediate Similarity	NPC476067
0.843	Intermediate Similarity	NPC41494
0.843	Intermediate Similarity	NPC216403
0.843	Intermediate Similarity	NPC186100
0.8424	Intermediate Similarity	NPC295646
0.8421	Intermediate Similarity	NPC469394
0.8421	Intermediate Similarity	NPC296558
0.8421	Intermediate Similarity	NPC469419
0.8421	Intermediate Similarity	NPC472621
0.8418	Intermediate Similarity	NPC473205
0.8418	Intermediate Similarity	NPC473776
0.8415	Intermediate Similarity	NPC257213
0.8415	Intermediate Similarity	NPC249471
0.8415	Intermediate Similarity	NPC473414
0.8415	Intermediate Similarity	NPC256142
0.8415	Intermediate Similarity	NPC242262
0.8415	Intermediate Similarity	NPC237549
0.8415	Intermediate Similarity	NPC472022
0.8415	Intermediate Similarity	NPC304876
0.8415	Intermediate Similarity	NPC158333
0.8415	Intermediate Similarity	NPC472030
0.8415	Intermediate Similarity	NPC265395
0.8415	Intermediate Similarity	NPC1173
0.8415	Intermediate Similarity	NPC472005
0.8412	Intermediate Similarity	NPC291977
0.8412	Intermediate Similarity	NPC223006
0.8412	Intermediate Similarity	NPC134047
0.8412	Intermediate Similarity	NPC272750
0.8412	Intermediate Similarity	NPC173729
0.8409	Intermediate Similarity	NPC108191
0.8409	Intermediate Similarity	NPC93685
0.8405	Intermediate Similarity	NPC279442
0.8405	Intermediate Similarity	NPC476394
0.8405	Intermediate Similarity	NPC98809
0.8402	Intermediate Similarity	NPC87431
0.8402	Intermediate Similarity	NPC469889
0.84	Intermediate Similarity	NPC475054
0.84	Intermediate Similarity	NPC469397
0.8391	Intermediate Similarity	NPC476374
0.8391	Intermediate Similarity	NPC471871
0.8385	Intermediate Similarity	NPC53520
0.8375	Intermediate Similarity	NPC477873
0.8375	Intermediate Similarity	NPC469447
0.8372	Intermediate Similarity	NPC283041
0.8372	Intermediate Similarity	NPC472622
0.8364	Intermediate Similarity	NPC114410
0.8364	Intermediate Similarity	NPC112523
0.8364	Intermediate Similarity	NPC26033
0.8364	Intermediate Similarity	NPC228204
0.8363	Intermediate Similarity	NPC191930
0.8362	Intermediate Similarity	NPC117668
0.8354	Intermediate Similarity	NPC474305
0.8354	Intermediate Similarity	NPC303989
0.8354	Intermediate Similarity	NPC477905
0.8354	Intermediate Similarity	NPC237441
0.8353	Intermediate Similarity	NPC473445
0.8353	Intermediate Similarity	NPC42797
0.8353	Intermediate Similarity	NPC144557
0.8352	Intermediate Similarity	NPC476358
0.8344	Intermediate Similarity	NPC470757
0.8344	Intermediate Similarity	NPC7095
0.8343	Intermediate Similarity	NPC472961
0.8343	Intermediate Similarity	NPC472962
0.8343	Intermediate Similarity	NPC155302
0.8343	Intermediate Similarity	NPC53889
0.8343	Intermediate Similarity	NPC161947
0.8333	Intermediate Similarity	NPC472639
0.8333	Intermediate Similarity	NPC476370
0.8333	Intermediate Similarity	NPC148185
0.8333	Intermediate Similarity	NPC4200
0.8333	Intermediate Similarity	NPC226759
0.8333	Intermediate Similarity	NPC167098
0.8333	Intermediate Similarity	NPC205721
0.8333	Intermediate Similarity	NPC296044
0.8333	Intermediate Similarity	NPC258856
0.8324	Intermediate Similarity	NPC112380
0.8324	Intermediate Similarity	NPC471870
0.8324	Intermediate Similarity	NPC21956
0.8324	Intermediate Similarity	NPC188079
0.8324	Intermediate Similarity	NPC472619
0.8324	Intermediate Similarity	NPC102810
0.8323	Intermediate Similarity	NPC46161
0.8323	Intermediate Similarity	NPC471876
0.8323	Intermediate Similarity	NPC239608
0.8323	Intermediate Similarity	NPC82592
0.8323	Intermediate Similarity	NPC145425
0.8323	Intermediate Similarity	NPC16082
0.8315	Intermediate Similarity	NPC182693
0.8314	Intermediate Similarity	NPC20237
0.8314	Intermediate Similarity	NPC13481
0.8314	Intermediate Similarity	NPC207575
0.8313	Intermediate Similarity	NPC180388
0.8313	Intermediate Similarity	NPC180944
0.8304	Intermediate Similarity	NPC476295
0.8304	Intermediate Similarity	NPC249181
0.8304	Intermediate Similarity	NPC277618
0.8303	Intermediate Similarity	NPC231668
0.8303	Intermediate Similarity	NPC77719
0.8295	Intermediate Similarity	NPC472723
0.8295	Intermediate Similarity	NPC79736
0.8295	Intermediate Similarity	NPC67629
0.8294	Intermediate Similarity	NPC288602
0.8294	Intermediate Similarity	NPC88841
0.8294	Intermediate Similarity	NPC477627
0.8293	Intermediate Similarity	NPC474306
0.8293	Intermediate Similarity	NPC475848
0.8287	Intermediate Similarity	NPC230670
0.8287	Intermediate Similarity	NPC71385
0.8286	Intermediate Similarity	NPC471969
0.8286	Intermediate Similarity	NPC469393
0.8286	Intermediate Similarity	NPC199357
0.8286	Intermediate Similarity	NPC124828
0.8286	Intermediate Similarity	NPC195972
0.8284	Intermediate Similarity	NPC87317
0.8282	Intermediate Similarity	NPC81698
0.8282	Intermediate Similarity	NPC250046
0.8282	Intermediate Similarity	NPC60509
0.8282	Intermediate Similarity	NPC58752
0.8278	Intermediate Similarity	NPC269625

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 NPC472803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	938
0.2-0.3	1869
0.3-0.4	2632
0.4-0.5	1921
0.5-0.6	985
0.6-0.7	346
0.7-0.8	98
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8475	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD7473	Discontinued
0.8199	Intermediate Similarity	NPD8166	Discontinued
0.8187	Intermediate Similarity	NPD8127	Discontinued
0.8166	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD6232	Discontinued
0.8125	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD8312	Approved
0.809	Intermediate Similarity	NPD8313	Approved
0.8079	Intermediate Similarity	NPD7685	Pre-registration
0.8077	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD6166	Phase 2
0.8011	Intermediate Similarity	NPD5844	Phase 1
0.7975	Intermediate Similarity	NPD4628	Phase 3
0.7966	Intermediate Similarity	NPD7074	Phase 3
0.7956	Intermediate Similarity	NPD8434	Phase 2
0.7955	Intermediate Similarity	NPD7228	Approved
0.7917	Intermediate Similarity	NPD7458	Discontinued
0.791	Intermediate Similarity	NPD7054	Approved
0.7882	Intermediate Similarity	NPD1934	Approved
0.7865	Intermediate Similarity	NPD7472	Approved
0.7861	Intermediate Similarity	NPD6234	Discontinued
0.7857	Intermediate Similarity	NPD8150	Discontinued
0.7853	Intermediate Similarity	NPD3818	Discontinued
0.7836	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6190	Approved
0.7778	Intermediate Similarity	NPD37	Approved
0.7765	Intermediate Similarity	NPD4380	Phase 2
0.7746	Intermediate Similarity	NPD4966	Approved
0.7746	Intermediate Similarity	NPD4967	Phase 2
0.7746	Intermediate Similarity	NPD4965	Approved
0.7735	Intermediate Similarity	NPD7808	Phase 3
0.7735	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7819	Suspended
0.7733	Intermediate Similarity	NPD2801	Approved
0.7733	Intermediate Similarity	NPD1465	Phase 2
0.7701	Intermediate Similarity	NPD7075	Discontinued
0.7688	Intermediate Similarity	NPD3817	Phase 2
0.768	Intermediate Similarity	NPD7251	Discontinued
0.7651	Intermediate Similarity	NPD7003	Approved
0.7644	Intermediate Similarity	NPD3882	Suspended
0.7633	Intermediate Similarity	NPD6273	Approved
0.7624	Intermediate Similarity	NPD6797	Phase 2
0.7614	Intermediate Similarity	NPD5494	Approved
0.7586	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6959	Discontinued
0.7565	Intermediate Similarity	NPD7435	Discontinued
0.7551	Intermediate Similarity	NPD8151	Discontinued
0.7543	Intermediate Similarity	NPD7768	Phase 2
0.7542	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7240	Approved
0.7485	Intermediate Similarity	NPD230	Phase 1
0.7471	Intermediate Similarity	NPD2532	Approved
0.7471	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2533	Approved
0.7471	Intermediate Similarity	NPD6801	Discontinued
0.7471	Intermediate Similarity	NPD2534	Approved
0.7457	Intermediate Similarity	NPD6599	Discontinued
0.7436	Intermediate Similarity	NPD7871	Phase 2
0.7436	Intermediate Similarity	NPD7870	Phase 2
0.7429	Intermediate Similarity	NPD5761	Phase 2
0.7429	Intermediate Similarity	NPD8455	Phase 2
0.7429	Intermediate Similarity	NPD5760	Phase 2
0.7425	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7874	Approved
0.7424	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7411	Suspended
0.7412	Intermediate Similarity	NPD1511	Approved
0.741	Intermediate Similarity	NPD2935	Discontinued
0.7409	Intermediate Similarity	NPD6780	Approved
0.7409	Intermediate Similarity	NPD6778	Approved
0.7409	Intermediate Similarity	NPD6776	Approved
0.7409	Intermediate Similarity	NPD6782	Approved
0.7409	Intermediate Similarity	NPD6781	Approved
0.7409	Intermediate Similarity	NPD6777	Approved
0.7409	Intermediate Similarity	NPD6779	Approved
0.7386	Intermediate Similarity	NPD5402	Approved
0.7385	Intermediate Similarity	NPD7698	Approved
0.7385	Intermediate Similarity	NPD7697	Approved
0.7385	Intermediate Similarity	NPD7696	Phase 3
0.7384	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7199	Phase 2
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.7347	Intermediate Similarity	NPD8319	Approved
0.7347	Intermediate Similarity	NPD8320	Phase 1
0.7337	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD9494	Approved
0.7326	Intermediate Similarity	NPD1512	Approved
0.7323	Intermediate Similarity	NPD7701	Phase 2
0.73	Intermediate Similarity	NPD7801	Approved
0.73	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7783	Phase 2
0.7299	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6559	Discontinued
0.7296	Intermediate Similarity	NPD7497	Discontinued
0.7289	Intermediate Similarity	NPD7097	Phase 1
0.7273	Intermediate Similarity	NPD447	Suspended
0.7268	Intermediate Similarity	NPD3751	Discontinued
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2799	Discontinued
0.7245	Intermediate Similarity	NPD6823	Phase 2
0.7238	Intermediate Similarity	NPD3787	Discontinued
0.7235	Intermediate Similarity	NPD4110	Phase 3
0.7235	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6386	Approved
0.7216	Intermediate Similarity	NPD6385	Approved
0.7216	Intermediate Similarity	NPD7700	Phase 2
0.7216	Intermediate Similarity	NPD7699	Phase 2
0.7212	Intermediate Similarity	NPD3620	Phase 2
0.7212	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6799	Approved
0.7208	Intermediate Similarity	NPD7680	Approved
0.7207	Intermediate Similarity	NPD3749	Approved
0.7198	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3764	Approved
0.7184	Intermediate Similarity	NPD5403	Approved
0.7179	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7799	Discontinued
0.7168	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2346	Discontinued
0.7151	Intermediate Similarity	NPD7236	Approved
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6535	Approved
0.715	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7135	Intermediate Similarity	NPD3750	Approved
0.7134	Intermediate Similarity	NPD3027	Phase 3
0.712	Intermediate Similarity	NPD8360	Approved
0.712	Intermediate Similarity	NPD8361	Approved
0.7118	Intermediate Similarity	NPD1549	Phase 2
0.7112	Intermediate Similarity	NPD8368	Discontinued
0.711	Intermediate Similarity	NPD7390	Discontinued
0.7101	Intermediate Similarity	NPD5408	Approved
0.7101	Intermediate Similarity	NPD5405	Approved
0.7101	Intermediate Similarity	NPD6100	Approved
0.7101	Intermediate Similarity	NPD5404	Approved
0.7101	Intermediate Similarity	NPD6099	Approved
0.7101	Intermediate Similarity	NPD5406	Approved
0.7095	Intermediate Similarity	NPD5353	Approved
0.7081	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD8485	Approved
0.7076	Intermediate Similarity	NPD6674	Discontinued
0.7069	Intermediate Similarity	NPD5401	Approved
0.7062	Intermediate Similarity	NPD7028	Phase 2
0.7059	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1653	Approved
0.7045	Intermediate Similarity	NPD7239	Suspended
0.7041	Intermediate Similarity	NPD7033	Discontinued
0.7035	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8435	Approved
0.703	Intermediate Similarity	NPD7095	Approved
0.7024	Intermediate Similarity	NPD1607	Approved
0.7021	Intermediate Similarity	NPD7038	Approved
0.7021	Intermediate Similarity	NPD7039	Approved
0.7011	Intermediate Similarity	NPD5242	Approved
0.7006	Intermediate Similarity	NPD943	Approved
0.7006	Intermediate Similarity	NPD1240	Approved
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2796	Approved
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD8407	Phase 2
0.699	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7177	Discontinued
0.6986	Remote Similarity	NPD7907	Approved
0.6978	Remote Similarity	NPD919	Approved
0.6975	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6355	Discontinued
0.6957	Remote Similarity	NPD8404	Phase 2
0.6957	Remote Similarity	NPD5710	Approved
0.6957	Remote Similarity	NPD5711	Approved
0.6946	Remote Similarity	NPD6663	Approved
0.6946	Remote Similarity	NPD8032	Phase 2
0.6941	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2493	Approved
0.6935	Remote Similarity	NPD2494	Approved
0.6931	Remote Similarity	NPD6765	Approved
0.6931	Remote Similarity	NPD6764	Approved
0.6927	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6873	Phase 2
0.6923	Remote Similarity	NPD6213	Phase 3
0.6923	Remote Similarity	NPD6212	Phase 3
0.6923	Remote Similarity	NPD6651	Approved
0.6923	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8285	Discontinued
0.6919	Remote Similarity	NPD3926	Phase 2
0.6918	Remote Similarity	NPD9545	Approved
0.6915	Remote Similarity	NPD4582	Approved
0.6915	Remote Similarity	NPD4583	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