NPASS Compound

Structure

NPC14116 OpenBabel07101719142D 49 54 0 0 1 0 0 0 0 0999 V2000 1.9490 1.4161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0374 -4.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0183 0.8920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0935 -3.7115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3007 -2.8038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2250 -1.3490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4507 -3.4238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6444 -3.8893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4507 -2.4927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1813 -2.3296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8381 -3.4238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6444 -2.0272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2606 -2.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7618 -1.6017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6317 -3.6271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3914 0.8448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5010 -0.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7368 -1.3583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3157 0.7336 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1477 -4.1760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1018 -0.0353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8381 -2.4927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9205 -1.3242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5213 -3.3527 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0508 -2.9939 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7285 -2.4450 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6825 -0.6333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4957 -0.1799 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0460 -1.8117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6129 -1.5617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9999 -1.1854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0318 -2.0272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9206 -0.1388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4110 -3.0783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3862 -0.9451 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1563 -2.0862 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 -7.4216 -0.7350 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4652 -4.8092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9466 -0.4267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6597 -0.3187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0318 -1.0962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4451 0.6305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1554 -0.4206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8410 -0.3993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4194 -1.9133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9405 -3.2683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3405 -0.5712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2255 -2.4927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 34 1 0 0 0 0 5 34 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 38 2 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 16 37 1 0 0 0 0 17 23 2 0 0 0 0 17 38 1 0 0 0 0 18 46 1 0 0 0 0 19 1 1 6 0 0 0 19 28 1 0 0 0 0 20 39 2 0 0 0 0 20 47 1 0 0 0 0 21 40 2 0 0 0 0 21 48 1 0 0 0 0 22 32 1 0 0 0 0 23 31 1 0 0 0 0 24 15 1 6 0 0 0 24 26 1 0 0 0 0 24 34 1 0 0 0 0 25 36 1 6 0 0 0 25 47 1 0 0 0 0 26 29 1 0 0 0 0 26 34 1 6 0 0 0 27 28 1 0 0 0 0 27 30 1 0 0 0 0 27 37 1 6 0 0 0 28 48 1 6 0 0 0 29 35 1 1 0 0 0 29 36 1 0 0 0 0 30 36 1 1 0 0 0 30 49 1 0 0 0 0 31 41 2 0 0 0 0 31 46 1 0 0 0 0 32 42 2 0 0 0 0 32 49 1 0 0 0 0 33 35 1 0 0 0 0 33 37 1 0 0 0 0 33 43 2 0 0 0 0 35 6 1 1 0 0 0 35 44 1 0 0 0 0 36 18 1 1 0 0 0 37 45 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	677.28
Volume:	675.857
LogP:	4.128
LogD:	3.005
LogS:	-4.083
# Rotatable Bonds:	11
TPSA:	175.62
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	5.292
Fsp3:	0.568
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:	-5.364
MDCK Permeability:	6.087969450163655e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.5
Plasma Protein Binding (PPB):	84.65768432617188%
Volume Distribution (VD):	1.559
Pgp-substrate:	14.438405990600586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.772
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.079
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	5.398
Half-life (T1/2):	0.512

ADMET: Toxicity

hERG Blockers:	0.492
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.104
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.055
Respiratory Toxicity:	0.249

Download Data

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

Natural Product: NPC14116

Natural Product ID:	NPC14116
*Common Name:**	Euphorbialoid B
IUPAC Name:	n.a.
Synonyms:	euphorbialoid B
Standard InCHIKey:	ZBRDJTDBVDPIHK-JHMQMCJESA-N
Standard InCHI:	InChI=1S/C37H43NO11/c1-19-16-37(45)27(28(19)48-21(3)40)30(49-32(42)22-11-8-7-9-12-22)36(18-46-31(41)23-13-10-14-38-17-23)25(47-20(2)39)15-24-26(34(24,4)5)29(36)35(6,44)33(37)43/h7-14,17,19,24-30,44-45H,15-16,18H2,1-6H3/t19-,24-,25+,26-,27+,28-,29-,30+,35-,36+,37+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)C)[C@H]([C@]1(COC(=O)c3cccnc3)[C@@H](C[C@H]3[C@@H]([C@H]1[C@@](C)(C2=O)O)C3(C)C)OC(=O)C)OC(=O)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2030580
PubChem CID:	60168053
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	Roots	Kunming, Yunnan Province, China	2010-JUL	PMID[21928782]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[21928782]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22560584]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7775985]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	15600.0	nM	PMID[531403]

☑ 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 NPC14116 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	363
0.1-0.2	1516
0.2-0.3	3349
0.3-0.4	11891
0.4-0.5	18763
0.5-0.6	5333
0.6-0.7	1227
0.7-0.8	87
0.8-0.85	104
0.85-0.9	55
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC285411
0.995	High Similarity	NPC134384
0.995	High Similarity	NPC311196
0.9333	High Similarity	NPC213143
0.9289	High Similarity	NPC238278
0.9059	High Similarity	NPC470190
0.9034	High Similarity	NPC187494
0.8962	High Similarity	NPC475601
0.8957	High Similarity	NPC328154
0.8957	High Similarity	NPC233727
0.8927	High Similarity	NPC470189
0.8927	High Similarity	NPC40919
0.8925	High Similarity	NPC96801
0.8925	High Similarity	NPC150698
0.8905	High Similarity	NPC477912
0.8883	High Similarity	NPC323551
0.8883	High Similarity	NPC476467
0.8883	High Similarity	NPC280473
0.8852	High Similarity	NPC319556
0.8852	High Similarity	NPC62367
0.8846	High Similarity	NPC62844
0.8846	High Similarity	NPC193361
0.8841	High Similarity	NPC51008
0.8841	High Similarity	NPC41724
0.881	High Similarity	NPC84815
0.881	High Similarity	NPC216428
0.881	High Similarity	NPC301368
0.8804	High Similarity	NPC471016
0.8796	High Similarity	NPC469748
0.8785	High Similarity	NPC124029
0.8785	High Similarity	NPC211920
0.8756	High Similarity	NPC477907
0.8756	High Similarity	NPC470306
0.8756	High Similarity	NPC207531
0.8756	High Similarity	NPC42678
0.8756	High Similarity	NPC477909
0.8738	High Similarity	NPC148860
0.8716	High Similarity	NPC35208
0.8714	High Similarity	NPC475408
0.8714	High Similarity	NPC471014
0.8714	High Similarity	NPC6981
0.8708	High Similarity	NPC4421
0.8708	High Similarity	NPC228331
0.8708	High Similarity	NPC319128
0.8702	High Similarity	NPC472553
0.8692	High Similarity	NPC477902
0.8685	High Similarity	NPC127026
0.8685	High Similarity	NPC127720
0.8673	High Similarity	NPC294579
0.8673	High Similarity	NPC144779
0.8667	High Similarity	NPC477910
0.8645	High Similarity	NPC471980
0.8643	High Similarity	NPC253482
0.8611	High Similarity	NPC146824
0.8598	High Similarity	NPC477911
0.8585	High Similarity	NPC75600
0.8585	High Similarity	NPC6576
0.8585	High Similarity	NPC212768
0.8585	High Similarity	NPC473115
0.8585	High Similarity	NPC473089
0.8585	High Similarity	NPC158020
0.8578	High Similarity	NPC473689
0.8578	High Similarity	NPC477906
0.8578	High Similarity	NPC292416
0.8571	High Similarity	NPC165837
0.8571	High Similarity	NPC475362
0.8558	High Similarity	NPC57797
0.8558	High Similarity	NPC48042
0.8558	High Similarity	NPC472550
0.8558	High Similarity	NPC250807
0.8558	High Similarity	NPC76565
0.8558	High Similarity	NPC304179
0.8551	High Similarity	NPC477903
0.8545	High Similarity	NPC472555
0.8539	High Similarity	NPC320324
0.8539	High Similarity	NPC319880
0.8539	High Similarity	NPC244839
0.8531	High Similarity	NPC264674
0.8527	High Similarity	NPC475648
0.8525	High Similarity	NPC328186
0.8525	High Similarity	NPC475600
0.8525	High Similarity	NPC87152
0.8525	High Similarity	NPC122968
0.8525	High Similarity	NPC476110
0.8525	High Similarity	NPC477787
0.8525	High Similarity	NPC228377
0.8525	High Similarity	NPC475631
0.8519	High Similarity	NPC475137
0.8519	High Similarity	NPC475498
0.8519	High Similarity	NPC473850
0.8519	High Similarity	NPC26881
0.85	High Similarity	NPC237702
0.8486	Intermediate Similarity	NPC470486
0.8486	Intermediate Similarity	NPC471190
0.8486	Intermediate Similarity	NPC475644
0.8486	Intermediate Similarity	NPC471977
0.8462	Intermediate Similarity	NPC475426
0.8462	Intermediate Similarity	NPC475406
0.8451	Intermediate Similarity	NPC477908
0.8451	Intermediate Similarity	NPC206343
0.8439	Intermediate Similarity	NPC470279
0.8433	Intermediate Similarity	NPC477899
0.8433	Intermediate Similarity	NPC477900
0.8426	Intermediate Similarity	NPC477788
0.8426	Intermediate Similarity	NPC235364
0.8423	Intermediate Similarity	NPC38959
0.8423	Intermediate Similarity	NPC327904
0.8421	Intermediate Similarity	NPC63041
0.8419	Intermediate Similarity	NPC477901
0.8409	Intermediate Similarity	NPC316841
0.8409	Intermediate Similarity	NPC475596
0.8409	Intermediate Similarity	NPC475303
0.8394	Intermediate Similarity	NPC473506
0.8381	Intermediate Similarity	NPC472752
0.8371	Intermediate Similarity	NPC30456
0.8364	Intermediate Similarity	NPC91125
0.8296	Intermediate Similarity	NPC327769
0.8278	Intermediate Similarity	NPC289086
0.8253	Intermediate Similarity	NPC475315
0.8253	Intermediate Similarity	NPC324619
0.8214	Intermediate Similarity	NPC170751
0.821	Intermediate Similarity	NPC475533
0.8148	Intermediate Similarity	NPC30570
0.8113	Intermediate Similarity	NPC475835
0.8077	Intermediate Similarity	NPC471015
0.8059	Intermediate Similarity	NPC473833
0.8043	Intermediate Similarity	NPC53255
0.8043	Intermediate Similarity	NPC326930
0.8043	Intermediate Similarity	NPC85879
0.8043	Intermediate Similarity	NPC475301
0.8009	Intermediate Similarity	NPC292517
0.8008	Intermediate Similarity	NPC13603
0.7945	Intermediate Similarity	NPC162812
0.7931	Intermediate Similarity	NPC471013
0.7931	Intermediate Similarity	NPC148896
0.7931	Intermediate Similarity	NPC180668
0.7885	Intermediate Similarity	NPC103230
0.7854	Intermediate Similarity	NPC476090
0.7842	Intermediate Similarity	NPC328928
0.7797	Intermediate Similarity	NPC10904
0.7769	Intermediate Similarity	NPC471978
0.7729	Intermediate Similarity	NPC471004
0.7673	Intermediate Similarity	NPC471979
0.7569	Intermediate Similarity	NPC309498
0.7489	Intermediate Similarity	NPC253314
0.7477	Intermediate Similarity	NPC109922
0.7441	Intermediate Similarity	NPC44354
0.744	Intermediate Similarity	NPC471997
0.7421	Intermediate Similarity	NPC470280
0.7407	Intermediate Similarity	NPC320748
0.7407	Intermediate Similarity	NPC324245
0.7385	Intermediate Similarity	NPC328559
0.7385	Intermediate Similarity	NPC155792
0.7385	Intermediate Similarity	NPC32451
0.7366	Intermediate Similarity	NPC111732
0.7353	Intermediate Similarity	NPC37473
0.7339	Intermediate Similarity	NPC79223
0.7285	Intermediate Similarity	NPC477043
0.7281	Intermediate Similarity	NPC141385
0.7281	Intermediate Similarity	NPC329024
0.7269	Intermediate Similarity	NPC135950
0.7253	Intermediate Similarity	NPC57690
0.7238	Intermediate Similarity	NPC471583
0.7238	Intermediate Similarity	NPC471782
0.722	Intermediate Similarity	NPC156044
0.7215	Intermediate Similarity	NPC103361
0.7197	Intermediate Similarity	NPC278540
0.7189	Intermediate Similarity	NPC146724
0.7173	Intermediate Similarity	NPC70155
0.7169	Intermediate Similarity	NPC317672
0.7169	Intermediate Similarity	NPC59033
0.7167	Intermediate Similarity	NPC235885
0.7137	Intermediate Similarity	NPC267926
0.713	Intermediate Similarity	NPC12944
0.713	Intermediate Similarity	NPC25442
0.7119	Intermediate Similarity	NPC311451
0.711	Intermediate Similarity	NPC21483
0.711	Intermediate Similarity	NPC198205
0.7091	Intermediate Similarity	NPC311054
0.7091	Intermediate Similarity	NPC112752
0.7089	Intermediate Similarity	NPC290529
0.7082	Intermediate Similarity	NPC106593
0.7072	Intermediate Similarity	NPC136573
0.7072	Intermediate Similarity	NPC176371
0.7067	Intermediate Similarity	NPC249614
0.7065	Intermediate Similarity	NPC107287
0.7062	Intermediate Similarity	NPC164340
0.7056	Intermediate Similarity	NPC131273
0.7056	Intermediate Similarity	NPC473441
0.7051	Intermediate Similarity	NPC266192
0.7051	Intermediate Similarity	NPC114974
0.7048	Intermediate Similarity	NPC314834
0.7045	Intermediate Similarity	NPC198390
0.7033	Intermediate Similarity	NPC191310
0.7032	Intermediate Similarity	NPC476212
0.7032	Intermediate Similarity	NPC476205
0.7032	Intermediate Similarity	NPC476206
0.7032	Intermediate Similarity	NPC259791
0.7032	Intermediate Similarity	NPC476256
0.7032	Intermediate Similarity	NPC476257

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 NPC14116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	576
0.2-0.3	712
0.3-0.4	1923
0.4-0.5	3517
0.5-0.6	1808
0.6-0.7	380
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7745	Intermediate Similarity	NPD8468	Phase 2
0.7734	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7678	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7396	Approved
0.7244	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7707	Approved
0.7157	Intermediate Similarity	NPD6635	Approved
0.7105	Intermediate Similarity	NPD3795	Approved
0.7105	Intermediate Similarity	NPD3794	Approved
0.708	Intermediate Similarity	NPD6529	Discontinued
0.7061	Intermediate Similarity	NPD7069	Discontinued
0.7044	Intermediate Similarity	NPD820	Phase 3
0.7042	Intermediate Similarity	NPD5891	Approved
0.7037	Intermediate Similarity	NPD1483	Discontinued
0.7022	Intermediate Similarity	NPD7010	Phase 3
0.7013	Intermediate Similarity	NPD8326	Phase 3
0.7013	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD8325	Phase 3
0.699	Remote Similarity	NPD5088	Discontinued
0.6987	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6987	Phase 1
0.6978	Remote Similarity	NPD3947	Discontinued
0.6943	Remote Similarity	NPD4417	Approved
0.6934	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3389	Approved
0.6897	Remote Similarity	NPD3394	Approved
0.6897	Remote Similarity	NPD3393	Approved
0.6886	Remote Similarity	NPD2510	Approved
0.6886	Remote Similarity	NPD2509	Approved
0.6885	Remote Similarity	NPD7886	Phase 2
0.6885	Remote Similarity	NPD7885	Phase 2
0.6881	Remote Similarity	NPD7234	Approved
0.6881	Remote Similarity	NPD7233	Approved
0.6866	Remote Similarity	NPD9271	Approved
0.6833	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6026	Approved
0.6822	Remote Similarity	NPD4301	Approved
0.6818	Remote Similarity	NPD2336	Approved
0.6814	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6770	Approved
0.68	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD53	Approved
0.6786	Remote Similarity	NPD7778	Approved
0.6786	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7777	Approved
0.6784	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3280	Approved
0.6776	Remote Similarity	NPD6642	Approved
0.6776	Remote Similarity	NPD6641	Approved
0.6766	Remote Similarity	NPD7878	Phase 2
0.6758	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD2831	Approved
0.6724	Remote Similarity	NPD5475	Discontinued
0.6712	Remote Similarity	NPD4376	Phase 3
0.671	Remote Similarity	NPD4506	Discontinued
0.6697	Remote Similarity	NPD8063	Discontinued
0.6696	Remote Similarity	NPD2307	Discontinued
0.6694	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD9075	Approved
0.6683	Remote Similarity	NPD9074	Approved
0.6682	Remote Similarity	NPD4948	Discontinued
0.6667	Remote Similarity	NPD8485	Approved
0.6653	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD4989	Phase 2
0.6639	Remote Similarity	NPD8479	Phase 2
0.6607	Remote Similarity	NPD6361	Phase 2
0.6606	Remote Similarity	NPD8021	Approved
0.6606	Remote Similarity	NPD6791	Phase 2
0.6606	Remote Similarity	NPD8020	Approved
0.6599	Remote Similarity	NPD8409	Suspended
0.6594	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6241	Phase 1
0.6589	Remote Similarity	NPD7708	Approved
0.6579	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7962	Phase 2
0.6574	Remote Similarity	NPD7967	Discontinued
0.6571	Remote Similarity	NPD2511	Approved
0.6567	Remote Similarity	NPD107	Approved
0.6559	Remote Similarity	NPD3006	Discontinued
0.6555	Remote Similarity	NPD1926	Approved
0.6552	Remote Similarity	NPD7803	Approved
0.6549	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD8360	Approved
0.6547	Remote Similarity	NPD8435	Approved
0.6547	Remote Similarity	NPD8361	Approved
0.6545	Remote Similarity	NPD4373	Phase 2
0.6537	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD5901	Discontinued
0.6531	Remote Similarity	NPD6962	Phase 2
0.6531	Remote Similarity	NPD7688	Phase 1
0.6529	Remote Similarity	NPD3925	Approved
0.6529	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7187	Phase 2
0.652	Remote Similarity	NPD6790	Phase 1
0.6516	Remote Similarity	NPD4889	Approved
0.6515	Remote Similarity	NPD6995	Phase 1
0.6515	Remote Similarity	NPD8356	Approved
0.6511	Remote Similarity	NPD7470	Discontinued
0.6509	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD4427	Phase 2
0.6502	Remote Similarity	NPD8289	Discontinued
0.649	Remote Similarity	NPD4952	Phase 3
0.6481	Remote Similarity	NPD7562	Approved
0.6476	Remote Similarity	NPD6226	Phase 3
0.6471	Remote Similarity	NPD5490	Discontinued
0.6471	Remote Similarity	NPD5482	Discontinued
0.6468	Remote Similarity	NPD2896	Discontinued
0.6463	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4528	Approved
0.646	Remote Similarity	NPD4526	Approved
0.646	Remote Similarity	NPD4529	Approved
0.6458	Remote Similarity	NPD7404	Approved
0.6457	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1270	Approved
0.6454	Remote Similarity	NPD7417	Discontinued
0.6448	Remote Similarity	NPD8091	Phase 3
0.6434	Remote Similarity	NPD5640	Discontinued
0.6422	Remote Similarity	NPD5100	Phase 3
0.6422	Remote Similarity	NPD6176	Phase 1
0.6417	Remote Similarity	NPD7395	Discontinued
0.6416	Remote Similarity	NPD6665	Discontinued
0.641	Remote Similarity	NPD3371	Approved
0.6408	Remote Similarity	NPD8430	Approved
0.6402	Remote Similarity	NPD8160	Phase 2
0.6398	Remote Similarity	NPD2581	Approved
0.6398	Remote Similarity	NPD2582	Approved
0.6398	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.639	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7576	Discontinued
0.6388	Remote Similarity	NPD4551	Phase 2
0.6387	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7467	Discontinued
0.638	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD5003	Discontinued
0.6375	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6825	Phase 1
0.6372	Remote Similarity	NPD6446	Discontinued
0.6368	Remote Similarity	NPD7957	Phase 1
0.6368	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6479	Discontinued
0.6364	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5827	Discontinued
0.6364	Remote Similarity	NPD8412	Phase 1
0.636	Remote Similarity	NPD7955	Approved
0.636	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.636	Remote Similarity	NPD7956	Approved
0.6359	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5022	Discontinued
0.6355	Remote Similarity	NPD1631	Approved
0.6352	Remote Similarity	NPD5513	Phase 2
0.6349	Remote Similarity	NPD4429	Discontinued
0.6345	Remote Similarity	NPD5866	Approved
0.6339	Remote Similarity	NPD4375	Approved
0.6337	Remote Similarity	NPD4923	Phase 1
0.6337	Remote Similarity	NPD6298	Discontinued
0.6335	Remote Similarity	NPD5805	Approved
0.6332	Remote Similarity	NPD5512	Phase 3
0.633	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6182	Approved
0.633	Remote Similarity	NPD43	Approved
0.6329	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6276	Discontinued
0.6327	Remote Similarity	NPD6281	Approved
0.6325	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6874	Approved
0.6314	Remote Similarity	NPD7191	Phase 2
0.6312	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3813	Approved
0.6306	Remote Similarity	NPD3178	Discontinued
0.6306	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7021	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD2809	Approved
0.6298	Remote Similarity	NPD7001	Phase 3
0.6298	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1996	Discontinued
0.6295	Remote Similarity	NPD8407	Phase 2
0.6293	Remote Similarity	NPD4600	Approved
0.6293	Remote Similarity	NPD4501	Approved
0.6293	Remote Similarity	NPD4601	Approved
0.6293	Remote Similarity	NPD4500	Approved
0.629	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD3354	Phase 2
0.6281	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7268	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