NPASS Compound

Structure

NPC238278 OpenBabel07101719122D 49 54 0 0 1 0 0 0 0 0999 V2000 -6.0666 2.5423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2212 2.9724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5528 -1.3343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0701 3.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8755 1.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9281 1.2346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1522 2.8177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1073 2.3384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6988 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7560 2.9022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9808 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6988 -1.9616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4276 1.6371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3252 2.5735 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4932 -1.0558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7662 4.1463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1820 2.1820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -1.4712 0.0000 C 0 0 0 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 -4.8042 1.4056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5348 1.8618 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1886 1.9305 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8494 -0.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8494 1.4712 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6988 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2993 1.2481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.9616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6538 2.6979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9808 0.9808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0533 2.4305 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6988 0.9808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2675 2.4623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5481 -1.4712 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2046 -1.7309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7405 5.1268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4358 3.1293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4605 0.6767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5481 -0.4904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3997 2.0052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0287 2.5330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7221 -0.1021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6281 3.6783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8448 1.2017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 -1.4712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2346 1.9281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 8 22 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 20 1 0 0 0 0 11 36 2 0 0 0 0 12 16 1 0 0 0 0 12 35 1 0 0 0 0 13 32 1 0 0 0 0 14 20 2 0 0 0 0 14 36 1 0 0 0 0 15 44 1 0 0 0 0 16 2 1 1 0 0 0 16 25 1 0 0 0 0 17 37 2 0 0 0 0 17 45 1 0 0 0 0 18 38 2 0 0 0 0 18 46 1 0 0 0 0 19 39 2 0 0 0 0 19 49 1 0 0 0 0 20 30 1 0 0 0 0 21 13 1 1 0 0 0 21 23 1 0 0 0 0 21 26 1 0 0 0 0 22 40 2 0 0 0 0 22 47 1 0 0 0 0 23 27 1 0 0 0 0 23 32 1 1 0 0 0 24 25 1 0 0 0 0 24 29 1 0 0 0 0 24 35 1 1 0 0 0 25 47 1 1 0 0 0 26 28 1 0 0 0 0 26 48 1 1 0 0 0 27 33 1 6 0 0 0 27 34 1 0 0 0 0 28 34 1 0 0 0 0 28 41 2 0 0 0 0 29 34 1 6 0 0 0 29 45 1 0 0 0 0 30 42 2 0 0 0 0 30 48 1 0 0 0 0 31 33 1 1 0 0 0 31 35 1 0 0 0 0 31 46 1 0 0 0 0 32 6 1 6 0 0 0 32 49 1 0 0 0 0 33 7 1 6 0 0 0 33 44 1 0 0 0 0 34 15 1 6 0 0 0 35 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	685.27
Volume:	664.119
LogP:	2.267
LogD:	1.494
LogS:	-4.464
# Rotatable Bonds:	12
TPSA:	190.92
# H-Bond Aceptor:	14
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	6.479
Fsp3:	0.686
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:	-5.343
MDCK Permeability:	0.0001231860078405589
Pgp-inhibitor:	0.999
Pgp-substrate:	0.101
Human Intestinal Absorption (HIA):	0.824
20% Bioavailability (F20%):	0.803
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	33.635826110839844%
Volume Distribution (VD):	1.377
Pgp-substrate:	31.85293960571289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.776
CYP3A4-substrate:	0.447

ADMET: Excretion

Clearance (CL):	2.489
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.313
Human Hepatotoxicity (H-HT):	0.937
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.495
Maximum Recommended Daily Dose:	0.114
Skin Sensitization:	0.176
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.314

Download Data

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

Natural Product: NPC238278

Natural Product ID:	NPC238278
*Common Name:**	Euphorbialoid G
IUPAC Name:	n.a.
Synonyms:	euphorbialoid G
Standard InCHIKey:	YAXJAINVCZAYMP-YFJLUURQSA-N
Standard InCHI:	InChI=1S/C35H43NO13/c1-8-22(40)47-25-16(2)12-35(43)24(25)29(45-17(3)37)34-15-44-33(7,31(35)46-18(4)38)27(34)23-21(13-32(23,6)49-19(5)39)26(28(34)41)48-30(42)20-10-9-11-36-14-20/h9-11,14,16,21,23-27,29,31,43H,8,12-13,15H2,1-7H3/t16-,21+,23-,24+,25-,26+,27-,29+,31-,32-,33+,34-,35+/m0/s1
SMILES:	CCC(=O)O[C@H]1[C@@H](C)C[C@]2([C@H]1[C@@H](OC(=O)C)[C@]13CO[C@@]([C@@H]2OC(=O)C)([C@@H]3[C@@H]2[C@H]([C@H](C1=O)OC(=O)c1cccnc1)C[C@]2(C)OC(=O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2030585
PubChem CID:	70681568
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic 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	=	48700.0	nM	PMID[482823]

☑ 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 NPC238278 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	379
0.1-0.2	1596
0.2-0.3	3590
0.3-0.4	12762
0.4-0.5	18210
0.5-0.6	5039
0.6-0.7	892
0.7-0.8	78
0.8-0.85	106
0.85-0.9	29
0.9-0.95	10
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9665	High Similarity	NPC213143
0.9378	High Similarity	NPC233727
0.9336	High Similarity	NPC311196
0.9336	High Similarity	NPC134384
0.9289	High Similarity	NPC285411
0.9289	High Similarity	NPC14116
0.9198	High Similarity	NPC475601
0.9179	High Similarity	NPC193361
0.9179	High Similarity	NPC62844
0.9091	High Similarity	NPC187494
0.907	High Similarity	NPC96801
0.907	High Similarity	NPC150698
0.8986	High Similarity	NPC40919
0.8986	High Similarity	NPC470189
0.8945	High Similarity	NPC35208
0.894	High Similarity	NPC469748
0.8932	High Similarity	NPC470190
0.8852	High Similarity	NPC280473
0.8852	High Similarity	NPC476467
0.8852	High Similarity	NPC323551
0.8843	High Similarity	NPC124029
0.8843	High Similarity	NPC211920
0.8837	High Similarity	NPC328154
0.8821	High Similarity	NPC319556
0.881	High Similarity	NPC51008
0.881	High Similarity	NPC41724
0.8784	High Similarity	NPC253482
0.8774	High Similarity	NPC471016
0.8768	High Similarity	NPC228331
0.8768	High Similarity	NPC319128
0.875	High Similarity	NPC477902
0.8726	High Similarity	NPC470306
0.8726	High Similarity	NPC207531
0.8721	High Similarity	NPC477906
0.871	High Similarity	NPC148860
0.8698	High Similarity	NPC477912
0.8692	High Similarity	NPC301368
0.8692	High Similarity	NPC84815
0.8685	High Similarity	NPC475408
0.8685	High Similarity	NPC471014
0.8679	High Similarity	NPC264674
0.8673	High Similarity	NPC472553
0.8667	High Similarity	NPC475648
0.8645	High Similarity	NPC62367
0.8638	High Similarity	NPC477910
0.8619	High Similarity	NPC472752
0.8605	High Similarity	NPC216428
0.8604	High Similarity	NPC475426
0.8598	High Similarity	NPC6981
0.8584	High Similarity	NPC146824
0.8578	High Similarity	NPC26881
0.8571	High Similarity	NPC127720
0.8571	High Similarity	NPC127026
0.8558	High Similarity	NPC294579
0.8558	High Similarity	NPC144779
0.8551	High Similarity	NPC477909
0.8551	High Similarity	NPC42678
0.8551	High Similarity	NPC477907
0.8545	High Similarity	NPC165837
0.8545	High Similarity	NPC475362
0.8532	High Similarity	NPC57797
0.8532	High Similarity	NPC250807
0.8532	High Similarity	NPC76565
0.8532	High Similarity	NPC471980
0.8531	High Similarity	NPC304179
0.8531	High Similarity	NPC48042
0.8531	High Similarity	NPC472550
0.8525	High Similarity	NPC477903
0.8514	High Similarity	NPC244839
0.8514	High Similarity	NPC320324
0.8514	High Similarity	NPC319880
0.8505	High Similarity	NPC4421
0.8493	Intermediate Similarity	NPC475137
0.8493	Intermediate Similarity	NPC475498
0.8493	Intermediate Similarity	NPC473850
0.8486	Intermediate Similarity	NPC235364
0.8486	Intermediate Similarity	NPC477911
0.8479	Intermediate Similarity	NPC477901
0.8475	Intermediate Similarity	NPC237702
0.8468	Intermediate Similarity	NPC292416
0.8468	Intermediate Similarity	NPC473689
0.8433	Intermediate Similarity	NPC472555
0.8423	Intermediate Similarity	NPC91125
0.8416	Intermediate Similarity	NPC475600
0.8416	Intermediate Similarity	NPC87152
0.8416	Intermediate Similarity	NPC477787
0.8416	Intermediate Similarity	NPC476110
0.8416	Intermediate Similarity	NPC328186
0.8416	Intermediate Similarity	NPC475631
0.8416	Intermediate Similarity	NPC228377
0.8416	Intermediate Similarity	NPC122968
0.8409	Intermediate Similarity	NPC477900
0.8409	Intermediate Similarity	NPC477899
0.84	Intermediate Similarity	NPC38959
0.84	Intermediate Similarity	NPC327904
0.8396	Intermediate Similarity	NPC63041
0.8387	Intermediate Similarity	NPC473115
0.8387	Intermediate Similarity	NPC158020
0.8387	Intermediate Similarity	NPC6576
0.8387	Intermediate Similarity	NPC212768
0.8387	Intermediate Similarity	NPC75600
0.8387	Intermediate Similarity	NPC473089
0.8378	Intermediate Similarity	NPC475644
0.8378	Intermediate Similarity	NPC470486
0.8378	Intermediate Similarity	NPC471190
0.8378	Intermediate Similarity	NPC471977
0.8356	Intermediate Similarity	NPC475406
0.8341	Intermediate Similarity	NPC206343
0.8341	Intermediate Similarity	NPC477908
0.8312	Intermediate Similarity	NPC324619
0.8312	Intermediate Similarity	NPC475315
0.8304	Intermediate Similarity	NPC475303
0.8304	Intermediate Similarity	NPC475596
0.8304	Intermediate Similarity	NPC316841
0.8295	Intermediate Similarity	NPC30570
0.8288	Intermediate Similarity	NPC473506
0.827	Intermediate Similarity	NPC473833
0.8268	Intermediate Similarity	NPC475533
0.8267	Intermediate Similarity	NPC30456
0.8235	Intermediate Similarity	NPC477788
0.8213	Intermediate Similarity	NPC471015
0.8194	Intermediate Similarity	NPC327769
0.8194	Intermediate Similarity	NPC170751
0.8157	Intermediate Similarity	NPC292517
0.8101	Intermediate Similarity	NPC475301
0.8101	Intermediate Similarity	NPC85879
0.8101	Intermediate Similarity	NPC326930
0.8101	Intermediate Similarity	NPC53255
0.8091	Intermediate Similarity	NPC162812
0.8069	Intermediate Similarity	NPC148896
0.8069	Intermediate Similarity	NPC180668
0.8069	Intermediate Similarity	NPC471013
0.8067	Intermediate Similarity	NPC13603
0.8066	Intermediate Similarity	NPC470279
0.7975	Intermediate Similarity	NPC471978
0.7932	Intermediate Similarity	NPC10904
0.7901	Intermediate Similarity	NPC328928
0.7878	Intermediate Similarity	NPC471979
0.7844	Intermediate Similarity	NPC475835
0.7834	Intermediate Similarity	NPC289086
0.7689	Intermediate Similarity	NPC476090
0.7639	Intermediate Similarity	NPC471004
0.7535	Intermediate Similarity	NPC103230
0.75	Intermediate Similarity	NPC141385
0.749	Intermediate Similarity	NPC37473
0.7478	Intermediate Similarity	NPC253314
0.7477	Intermediate Similarity	NPC309498
0.7397	Intermediate Similarity	NPC324245
0.7397	Intermediate Similarity	NPC320748
0.7376	Intermediate Similarity	NPC32451
0.7376	Intermediate Similarity	NPC155792
0.7376	Intermediate Similarity	NPC328559
0.733	Intermediate Similarity	NPC79223
0.7306	Intermediate Similarity	NPC109922
0.7281	Intermediate Similarity	NPC111732
0.7273	Intermediate Similarity	NPC329024
0.7234	Intermediate Similarity	NPC235885
0.7212	Intermediate Similarity	NPC156044
0.7206	Intermediate Similarity	NPC476516
0.7189	Intermediate Similarity	NPC44354
0.7189	Intermediate Similarity	NPC131273
0.7189	Intermediate Similarity	NPC473441
0.7173	Intermediate Similarity	NPC57690
0.7162	Intermediate Similarity	NPC317672
0.7162	Intermediate Similarity	NPC59033
0.7161	Intermediate Similarity	NPC141428
0.7124	Intermediate Similarity	NPC12944
0.7124	Intermediate Similarity	NPC477043
0.7124	Intermediate Similarity	NPC25442
0.7106	Intermediate Similarity	NPC2395
0.7104	Intermediate Similarity	NPC135950
0.7103	Intermediate Similarity	NPC471997
0.7103	Intermediate Similarity	NPC317010
0.7085	Intermediate Similarity	NPC107123
0.7076	Intermediate Similarity	NPC106593
0.7068	Intermediate Similarity	NPC134637
0.7059	Intermediate Similarity	NPC267926
0.7054	Intermediate Similarity	NPC103361
0.7031	Intermediate Similarity	NPC470280
0.702	Intermediate Similarity	NPC471782
0.702	Intermediate Similarity	NPC471583
0.7012	Intermediate Similarity	NPC290529
0.6992	Remote Similarity	NPC140311
0.6991	Remote Similarity	NPC176371
0.6991	Remote Similarity	NPC136573
0.698	Remote Similarity	NPC278540
0.6976	Remote Similarity	NPC476517
0.6975	Remote Similarity	NPC473667
0.6975	Remote Similarity	NPC266192
0.6968	Remote Similarity	NPC114974
0.6955	Remote Similarity	NPC70155
0.6952	Remote Similarity	NPC55744
0.6951	Remote Similarity	NPC476205
0.6951	Remote Similarity	NPC476212
0.6951	Remote Similarity	NPC476206
0.6951	Remote Similarity	NPC476257
0.6951	Remote Similarity	NPC476207
0.6951	Remote Similarity	NPC146724
0.6951	Remote Similarity	NPC476256
0.6951	Remote Similarity	NPC259791

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 NPC238278 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	562
0.2-0.3	790
0.3-0.4	2270
0.4-0.5	3584
0.5-0.6	1490
0.6-0.7	205
0.7-0.8	3
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
0.7731	Intermediate Similarity	NPD8468	Phase 2
0.7718	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7396	Approved
0.7104	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD8325	Phase 3
0.7082	Intermediate Similarity	NPD8326	Phase 3
0.7082	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7707	Approved
0.7039	Intermediate Similarity	NPD820	Phase 3
0.7033	Intermediate Similarity	NPD1483	Discontinued
0.7013	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD3795	Approved
0.6953	Remote Similarity	NPD3794	Approved
0.6905	Remote Similarity	NPD5088	Discontinued
0.6825	Remote Similarity	NPD6635	Approved
0.6822	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8485	Approved
0.681	Remote Similarity	NPD2510	Approved
0.681	Remote Similarity	NPD2509	Approved
0.6781	Remote Similarity	NPD6529	Discontinued
0.6761	Remote Similarity	NPD5891	Approved
0.6753	Remote Similarity	NPD2831	Approved
0.6753	Remote Similarity	NPD3947	Discontinued
0.6747	Remote Similarity	NPD7885	Phase 2
0.6747	Remote Similarity	NPD7886	Phase 2
0.6739	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4506	Discontinued
0.6699	Remote Similarity	NPD9271	Approved
0.6697	Remote Similarity	NPD6642	Approved
0.6697	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6641	Approved
0.6696	Remote Similarity	NPD8435	Approved
0.6695	Remote Similarity	NPD7069	Discontinued
0.6681	Remote Similarity	NPD3394	Approved
0.6681	Remote Similarity	NPD3393	Approved
0.6681	Remote Similarity	NPD3389	Approved
0.6681	Remote Similarity	NPD6987	Phase 1
0.6667	Remote Similarity	NPD2336	Approved
0.6667	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8409	Suspended
0.6653	Remote Similarity	NPD4417	Approved
0.6653	Remote Similarity	NPD4989	Phase 2
0.6652	Remote Similarity	NPD7010	Phase 3
0.6639	Remote Similarity	NPD3280	Approved
0.6639	Remote Similarity	NPD8479	Phase 2
0.6638	Remote Similarity	NPD53	Approved
0.6638	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7777	Approved
0.6638	Remote Similarity	NPD7778	Approved
0.6625	Remote Similarity	NPD7878	Phase 2
0.6624	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD8361	Approved
0.6622	Remote Similarity	NPD8360	Approved
0.6613	Remote Similarity	NPD4373	Phase 2
0.6607	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3925	Approved
0.6592	Remote Similarity	NPD8407	Phase 2
0.659	Remote Similarity	NPD7708	Approved
0.6579	Remote Similarity	NPD4427	Phase 2
0.6578	Remote Similarity	NPD7233	Approved
0.6578	Remote Similarity	NPD7234	Approved
0.6559	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7803	Approved
0.655	Remote Similarity	NPD2307	Discontinued
0.6543	Remote Similarity	NPD4301	Approved
0.6532	Remote Similarity	NPD6962	Phase 2
0.6529	Remote Similarity	NPD6770	Approved
0.6524	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9075	Approved
0.6522	Remote Similarity	NPD9074	Approved
0.6515	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6026	Approved
0.6495	Remote Similarity	NPD2511	Approved
0.6494	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3006	Discontinued
0.6492	Remote Similarity	NPD4952	Phase 3
0.6485	Remote Similarity	NPD8462	Phase 1
0.6478	Remote Similarity	NPD4086	Phase 1
0.6475	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8370	Discontinued
0.646	Remote Similarity	NPD4948	Discontinued
0.6457	Remote Similarity	NPD8368	Discontinued
0.6444	Remote Similarity	NPD5475	Discontinued
0.6443	Remote Similarity	NPD6825	Phase 1
0.6441	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1926	Approved
0.6408	Remote Similarity	NPD107	Approved
0.6392	Remote Similarity	NPD6790	Phase 1
0.6389	Remote Similarity	NPD8329	Phase 3
0.6375	Remote Similarity	NPD7470	Discontinued
0.6371	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5640	Discontinued
0.6364	Remote Similarity	NPD7955	Approved
0.6364	Remote Similarity	NPD7956	Approved
0.636	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7962	Phase 2
0.6348	Remote Similarity	NPD6665	Discontinued
0.6348	Remote Similarity	NPD4376	Phase 3
0.6337	Remote Similarity	NPD8466	Approved
0.6337	Remote Similarity	NPD8465	Approved
0.6337	Remote Similarity	NPD8467	Approved
0.6337	Remote Similarity	NPD8160	Phase 2
0.6335	Remote Similarity	NPD7688	Phase 1
0.6333	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD8063	Discontinued
0.6322	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.632	Remote Similarity	NPD4551	Phase 2
0.632	Remote Similarity	NPD6361	Phase 2
0.6318	Remote Similarity	NPD7967	Discontinued
0.6316	Remote Similarity	NPD6791	Phase 2
0.6316	Remote Similarity	NPD6995	Phase 1
0.6311	Remote Similarity	NPD8404	Phase 2
0.6303	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5866	Approved
0.6278	Remote Similarity	NPD7799	Discontinued
0.6266	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8091	Phase 3
0.6261	Remote Similarity	NPD5901	Discontinued
0.6261	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8356	Approved
0.6245	Remote Similarity	NPD8459	Approved
0.6245	Remote Similarity	NPD8426	Approved
0.6245	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD8460	Approved
0.6245	Remote Similarity	NPD8020	Approved
0.6245	Remote Similarity	NPD8021	Approved
0.6245	Remote Similarity	NPD8425	Approved
0.6239	Remote Similarity	NPD5003	Discontinued
0.6239	Remote Similarity	NPD6206	Phase 1
0.6239	Remote Similarity	NPD3178	Discontinued
0.6232	Remote Similarity	NPD2896	Discontinued
0.6231	Remote Similarity	NPD8375	Approved
0.623	Remote Similarity	NPD4897	Phase 2
0.623	Remote Similarity	NPD5022	Discontinued
0.623	Remote Similarity	NPD8374	Phase 3
0.6228	Remote Similarity	NPD6241	Phase 1
0.6227	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1270	Approved
0.6221	Remote Similarity	NPD5482	Discontinued
0.6218	Remote Similarity	NPD5513	Phase 2
0.6218	Remote Similarity	NPD8427	Approved
0.6218	Remote Similarity	NPD8429	Approved
0.6218	Remote Similarity	NPD6176	Phase 1
0.6218	Remote Similarity	NPD8428	Approved
0.621	Remote Similarity	NPD6298	Discontinued
0.621	Remote Similarity	NPD5506	Approved
0.621	Remote Similarity	NPD1631	Approved
0.621	Remote Similarity	NPD5507	Approved
0.6204	Remote Similarity	NPD5490	Discontinued
0.6202	Remote Similarity	NPD7417	Discontinued
0.6202	Remote Similarity	NPD7576	Discontinued
0.62	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.619	Remote Similarity	NPD2564	Approved
0.619	Remote Similarity	NPD2565	Phase 2
0.6183	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4528	Approved
0.618	Remote Similarity	NPD4529	Approved
0.618	Remote Similarity	NPD4526	Approved
0.6179	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7187	Phase 2
0.6175	Remote Similarity	NPD2581	Approved
0.6175	Remote Similarity	NPD8289	Discontinued
0.6175	Remote Similarity	NPD2582	Approved
0.6171	Remote Similarity	NPD1575	Approved
0.6171	Remote Similarity	NPD1573	Approved
0.6169	Remote Similarity	NPD1996	Discontinued
0.6167	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7001	Phase 3
0.6164	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD751	Clinical (unspecified phase)
0.616	Remote Similarity	NPD4600	Approved
0.616	Remote Similarity	NPD4601	Approved
0.616	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3217	Phase 2
0.6157	Remote Similarity	NPD4889	Approved
0.6151	Remote Similarity	NPD7497	Discontinued
0.6151	Remote Similarity	NPD8430	Approved
0.6147	Remote Similarity	NPD4334	Discontinued
0.6145	Remote Similarity	NPD6276	Discontinued
0.6145	Remote Similarity	NPD5147	Discontinued
0.6145	Remote Similarity	NPD4923	Phase 1
0.6143	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD3371	Approved
0.6141	Remote Similarity	NPD7562	Approved
0.6137	Remote Similarity	NPD4950	Approved
0.613	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7404	Approved
0.6128	Remote Similarity	NPD6226	Phase 3
0.6123	Remote Similarity	NPD5899	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