NPASS Compound

Structure

NPC193361 OpenBabel07101718302D 47 51 0 0 1 0 0 0 0 0999 V2000 -4.1992 -2.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8624 4.0618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1886 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9431 -2.1931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4504 -1.4685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0696 0.1672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5976 0.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0105 -1.6398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3784 1.4376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6315 0.8600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3079 1.5834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5098 2.0555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2520 1.0795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5303 -2.1348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6318 -0.4336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4792 0.7028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4191 -1.8163 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4782 2.7774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2550 -3.0755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9431 -1.2490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5288 -1.6735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7582 -0.0756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3079 0.6393 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3274 1.5834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4846 -0.6079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3909 -0.8726 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5098 0.1672 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2063 0.2943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0114 -0.6531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0113 -1.4585 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1255 0.1672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3691 -0.7664 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3274 0.6393 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9528 -1.3879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3787 0.1439 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5760 3.0557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9101 -3.9544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7608 -0.7769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2456 -2.5742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1451 2.0555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1381 -1.5887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8984 0.9365 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6663 -2.3374 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1377 -0.2951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1255 -0.7769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1095 -0.9779 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 31 1 0 0 0 0 7 31 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 22 1 0 0 0 0 11 12 2 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 35 2 0 0 0 0 14 17 1 0 0 0 0 14 34 1 0 0 0 0 15 22 2 0 0 0 0 15 35 1 0 0 0 0 16 42 1 0 0 0 0 17 1 1 6 0 0 0 17 26 1 0 0 0 0 18 36 2 0 0 0 0 18 43 1 0 0 0 0 19 37 2 0 0 0 0 19 44 1 0 0 0 0 20 38 2 0 0 0 0 20 46 1 0 0 0 0 21 39 2 0 0 0 0 21 47 1 0 0 0 0 22 29 1 0 0 0 0 23 27 1 0 0 0 0 23 31 1 6 0 0 0 24 33 1 0 0 0 0 24 40 2 0 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 25 34 1 6 0 0 0 26 45 1 6 0 0 0 27 32 1 1 0 0 0 27 33 1 0 0 0 0 28 33 1 1 0 0 0 28 43 1 0 0 0 0 29 41 2 0 0 0 0 29 45 1 0 0 0 0 30 32 1 6 0 0 0 30 34 1 0 0 0 0 30 44 1 0 0 0 0 31 46 1 0 0 0 0 32 8 1 6 0 0 0 32 42 1 0 0 0 0 33 16 1 1 0 0 0 34 47 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	655.26
Volume:	643.953
LogP:	2.212
LogD:	1.414
LogS:	-3.914
# Rotatable Bonds:	12
TPSA:	170.69
# H-Bond Aceptor:	13
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	6.161
Fsp3:	0.618
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:	-5.328
MDCK Permeability:	8.278335008071736e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.843
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.393
Plasma Protein Binding (PPB):	41.531517028808594%
Volume Distribution (VD):	1.708
Pgp-substrate:	31.094078063964844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.711
CYP3A4-substrate:	0.469

ADMET: Excretion

Clearance (CL):	2.348
Half-life (T1/2):	0.765

ADMET: Toxicity

hERG Blockers:	0.798
Human Hepatotoxicity (H-HT):	0.986
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.502
Skin Sensitization:	0.845
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC193361

Natural Product ID:	NPC193361
*Common Name:**	Euphorbialoid E
IUPAC Name:	n.a.
Synonyms:	euphorbialoid E
Standard InCHIKey:	XUEVAXNOCWUQGK-QQFHXDICSA-N
Standard InCHI:	InChI=1S/C34H41NO12/c1-17-14-34(47-21(5)39)25(26(17)45-29(41)22-10-9-13-35-15-22)28(43-18(2)36)33-16-42-32(8,30(34)44-19(3)37)27(33)23(11-12-24(33)40)31(6,7)46-20(4)38/h9-13,15,17,23,25-28,30H,14,16H2,1-8H3/t17-,23-,25+,26-,27-,28+,30-,32+,33+,34+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)c1cccnc1)[C@H]([C@]13CO[C@](C)([C@@H]3[C@H](C=CC1=O)C(C)(C)OC(=O)C)[C@@H]2OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2030583
PubChem CID:	60168065
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	=	33700.0	nM	PMID[470644]

☑ 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 NPC193361 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	383
0.1-0.2	1575
0.2-0.3	4706
0.3-0.4	14082
0.4-0.5	16414
0.5-0.6	4437
0.6-0.7	866
0.7-0.8	164
0.8-0.85	31
0.85-0.9	17
0.9-0.95	20
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC62844
0.9536	High Similarity	NPC323551
0.9536	High Similarity	NPC280473
0.9487	High Similarity	NPC51008
0.9487	High Similarity	NPC41724
0.9394	High Similarity	NPC187494
0.9385	High Similarity	NPC470189
0.9385	High Similarity	NPC40919
0.933	High Similarity	NPC470190
0.9307	High Similarity	NPC233727
0.9289	High Similarity	NPC165837
0.9223	High Similarity	NPC213143
0.92	High Similarity	NPC319556
0.9179	High Similarity	NPC238278
0.91	High Similarity	NPC207531
0.9045	High Similarity	NPC476467
0.8846	High Similarity	NPC285411
0.8846	High Similarity	NPC14116
0.8804	High Similarity	NPC311196
0.8804	High Similarity	NPC134384
0.8768	High Similarity	NPC264674
0.866	High Similarity	NPC26881
0.8614	High Similarity	NPC472752
0.8606	High Similarity	NPC477903
0.8578	High Similarity	NPC475601
0.8578	High Similarity	NPC124029
0.8565	High Similarity	NPC235364
0.8558	High Similarity	NPC477901
0.8498	Intermediate Similarity	NPC91125
0.8495	Intermediate Similarity	NPC4421
0.8491	Intermediate Similarity	NPC211920
0.8483	Intermediate Similarity	NPC477900
0.8483	Intermediate Similarity	NPC477902
0.8483	Intermediate Similarity	NPC477899
0.8458	Intermediate Similarity	NPC477906
0.8458	Intermediate Similarity	NPC150698
0.8458	Intermediate Similarity	NPC96801
0.8419	Intermediate Similarity	NPC469748
0.8413	Intermediate Similarity	NPC471016
0.8398	Intermediate Similarity	NPC472553
0.8373	Intermediate Similarity	NPC158020
0.8373	Intermediate Similarity	NPC6576
0.8373	Intermediate Similarity	NPC473115
0.8373	Intermediate Similarity	NPC212768
0.8373	Intermediate Similarity	NPC62367
0.8373	Intermediate Similarity	NPC75600
0.8373	Intermediate Similarity	NPC473089
0.8365	Intermediate Similarity	NPC470306
0.8341	Intermediate Similarity	NPC35208
0.8333	Intermediate Similarity	NPC84815
0.8333	Intermediate Similarity	NPC216428
0.8333	Intermediate Similarity	NPC301368
0.8325	Intermediate Similarity	NPC475408
0.8325	Intermediate Similarity	NPC471014
0.831	Intermediate Similarity	NPC328154
0.8278	Intermediate Similarity	NPC42678
0.8278	Intermediate Similarity	NPC477907
0.8278	Intermediate Similarity	NPC477909
0.8257	Intermediate Similarity	NPC475426
0.8255	Intermediate Similarity	NPC477912
0.8252	Intermediate Similarity	NPC304179
0.8252	Intermediate Similarity	NPC48042
0.8252	Intermediate Similarity	NPC472550
0.8238	Intermediate Similarity	NPC6981
0.823	Intermediate Similarity	NPC319128
0.823	Intermediate Similarity	NPC228331
0.8216	Intermediate Similarity	NPC477788
0.8216	Intermediate Similarity	NPC127720
0.8216	Intermediate Similarity	NPC127026
0.8199	Intermediate Similarity	NPC144779
0.8199	Intermediate Similarity	NPC294579
0.819	Intermediate Similarity	NPC253482
0.819	Intermediate Similarity	NPC477910
0.8186	Intermediate Similarity	NPC148860
0.8178	Intermediate Similarity	NPC57797
0.8178	Intermediate Similarity	NPC76565
0.8178	Intermediate Similarity	NPC250807
0.8178	Intermediate Similarity	NPC471980
0.816	Intermediate Similarity	NPC472555
0.814	Intermediate Similarity	NPC475498
0.814	Intermediate Similarity	NPC475137
0.814	Intermediate Similarity	NPC473850
0.8116	Intermediate Similarity	NPC63041
0.808	Intermediate Similarity	NPC475648
0.8066	Intermediate Similarity	NPC477908
0.8066	Intermediate Similarity	NPC206343
0.8065	Intermediate Similarity	NPC328186
0.8065	Intermediate Similarity	NPC87152
0.8065	Intermediate Similarity	NPC475600
0.8065	Intermediate Similarity	NPC475631
0.8065	Intermediate Similarity	NPC122968
0.8065	Intermediate Similarity	NPC477787
0.8065	Intermediate Similarity	NPC476110
0.8065	Intermediate Similarity	NPC228377
0.8065	Intermediate Similarity	NPC146824
0.8048	Intermediate Similarity	NPC292517
0.8047	Intermediate Similarity	NPC477911
0.8039	Intermediate Similarity	NPC470279
0.8028	Intermediate Similarity	NPC470486
0.8028	Intermediate Similarity	NPC471190
0.8028	Intermediate Similarity	NPC475362
0.8028	Intermediate Similarity	NPC475644
0.8028	Intermediate Similarity	NPC471977
0.8019	Intermediate Similarity	NPC30570
0.7955	Intermediate Similarity	NPC292416
0.7955	Intermediate Similarity	NPC475596
0.7955	Intermediate Similarity	NPC473689
0.7955	Intermediate Similarity	NPC316841
0.7955	Intermediate Similarity	NPC475303
0.7936	Intermediate Similarity	NPC473506
0.7919	Intermediate Similarity	NPC244839
0.7919	Intermediate Similarity	NPC319880
0.7919	Intermediate Similarity	NPC320324
0.7919	Intermediate Similarity	NPC30456
0.7885	Intermediate Similarity	NPC289086
0.7883	Intermediate Similarity	NPC237702
0.7848	Intermediate Similarity	NPC327769
0.7848	Intermediate Similarity	NPC475406
0.7848	Intermediate Similarity	NPC170751
0.7814	Intermediate Similarity	NPC162812
0.7812	Intermediate Similarity	NPC38959
0.7812	Intermediate Similarity	NPC327904
0.7745	Intermediate Similarity	NPC103230
0.7739	Intermediate Similarity	NPC475315
0.7739	Intermediate Similarity	NPC324619
0.7729	Intermediate Similarity	NPC180668
0.7729	Intermediate Similarity	NPC471013
0.7729	Intermediate Similarity	NPC148896
0.7725	Intermediate Similarity	NPC471015
0.7712	Intermediate Similarity	NPC473833
0.7696	Intermediate Similarity	NPC475533
0.7679	Intermediate Similarity	NPC471004
0.7642	Intermediate Similarity	NPC475835
0.7597	Intermediate Similarity	NPC10904
0.7596	Intermediate Similarity	NPC320748
0.7596	Intermediate Similarity	NPC324245
0.7594	Intermediate Similarity	NPC309498
0.7571	Intermediate Similarity	NPC328559
0.7571	Intermediate Similarity	NPC32451
0.7542	Intermediate Similarity	NPC326930
0.7542	Intermediate Similarity	NPC53255
0.7542	Intermediate Similarity	NPC85879
0.7542	Intermediate Similarity	NPC475301
0.7536	Intermediate Similarity	NPC135950
0.7524	Intermediate Similarity	NPC79223
0.7511	Intermediate Similarity	NPC13603
0.7488	Intermediate Similarity	NPC155792
0.7476	Intermediate Similarity	NPC103361
0.7464	Intermediate Similarity	NPC329024
0.7435	Intermediate Similarity	NPC107287
0.7427	Intermediate Similarity	NPC471978
0.7425	Intermediate Similarity	NPC476090
0.7424	Intermediate Similarity	NPC249614
0.7395	Intermediate Similarity	NPC156044
0.7385	Intermediate Similarity	NPC111732
0.7355	Intermediate Similarity	NPC328928
0.7346	Intermediate Similarity	NPC59033
0.7346	Intermediate Similarity	NPC317672
0.7336	Intermediate Similarity	NPC471979
0.7333	Intermediate Similarity	NPC109922
0.7311	Intermediate Similarity	NPC123395
0.7302	Intermediate Similarity	NPC25442
0.7302	Intermediate Similarity	NPC12944
0.7295	Intermediate Similarity	NPC44354
0.7291	Intermediate Similarity	NPC317010
0.7273	Intermediate Similarity	NPC471546
0.7225	Intermediate Similarity	NPC112741
0.7214	Intermediate Similarity	NPC191310
0.72	Intermediate Similarity	NPC253314
0.7149	Intermediate Similarity	NPC37473
0.7143	Intermediate Similarity	NPC141385
0.7095	Intermediate Similarity	NPC469489
0.7067	Intermediate Similarity	NPC282103
0.7042	Intermediate Similarity	NPC259791
0.7042	Intermediate Similarity	NPC476256
0.7042	Intermediate Similarity	NPC476257
0.7042	Intermediate Similarity	NPC476207
0.7042	Intermediate Similarity	NPC476205
0.7042	Intermediate Similarity	NPC476206
0.7042	Intermediate Similarity	NPC476212
0.7042	Intermediate Similarity	NPC476129
0.7009	Intermediate Similarity	NPC108804
0.7009	Intermediate Similarity	NPC476218
0.7	Intermediate Similarity	NPC325775
0.7	Intermediate Similarity	NPC328798
0.6982	Remote Similarity	NPC314834
0.6971	Remote Similarity	NPC327373
0.6968	Remote Similarity	NPC470280
0.6959	Remote Similarity	NPC214428
0.6957	Remote Similarity	NPC471997
0.6948	Remote Similarity	NPC56170
0.6948	Remote Similarity	NPC55493
0.6942	Remote Similarity	NPC476516
0.6938	Remote Similarity	NPC207851
0.692	Remote Similarity	NPC318299
0.6908	Remote Similarity	NPC164340
0.6901	Remote Similarity	NPC138370
0.6901	Remote Similarity	NPC114974
0.6891	Remote Similarity	NPC159630
0.6891	Remote Similarity	NPC230085

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 NPC193361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	578
0.2-0.3	772
0.3-0.4	2202
0.4-0.5	3499
0.5-0.6	1622
0.6-0.7	237
0.7-0.8	7
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
0.8325	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD820	Phase 3
0.7465	Intermediate Similarity	NPD7396	Approved
0.7246	Intermediate Similarity	NPD8468	Phase 2
0.7225	Intermediate Similarity	NPD9271	Approved
0.7202	Intermediate Similarity	NPD2510	Approved
0.7202	Intermediate Similarity	NPD2509	Approved
0.7175	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8326	Phase 3
0.7175	Intermediate Similarity	NPD8325	Phase 3
0.7143	Intermediate Similarity	NPD3947	Discontinued
0.7091	Intermediate Similarity	NPD4506	Discontinued
0.7079	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3394	Approved
0.7054	Intermediate Similarity	NPD3389	Approved
0.7054	Intermediate Similarity	NPD3393	Approved
0.7042	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5088	Discontinued
0.7	Intermediate Similarity	NPD6635	Approved
0.6964	Remote Similarity	NPD3795	Approved
0.6964	Remote Similarity	NPD3794	Approved
0.6962	Remote Similarity	NPD7885	Phase 2
0.6962	Remote Similarity	NPD7886	Phase 2
0.6951	Remote Similarity	NPD4417	Approved
0.6937	Remote Similarity	NPD6529	Discontinued
0.6911	Remote Similarity	NPD107	Approved
0.6909	Remote Similarity	NPD2831	Approved
0.6886	Remote Similarity	NPD6770	Approved
0.6878	Remote Similarity	NPD7010	Phase 3
0.6866	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6641	Approved
0.686	Remote Similarity	NPD6642	Approved
0.6833	Remote Similarity	NPD1483	Discontinued
0.6826	Remote Similarity	NPD4301	Approved
0.6789	Remote Similarity	NPD7777	Approved
0.6789	Remote Similarity	NPD7778	Approved
0.6789	Remote Similarity	NPD53	Approved
0.6783	Remote Similarity	NPD8479	Phase 2
0.677	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD9074	Approved
0.6769	Remote Similarity	NPD7878	Phase 2
0.6769	Remote Similarity	NPD9075	Approved
0.6765	Remote Similarity	NPD3006	Discontinued
0.6744	Remote Similarity	NPD2336	Approved
0.6726	Remote Similarity	NPD5475	Discontinued
0.671	Remote Similarity	NPD3280	Approved
0.6701	Remote Similarity	NPD1270	Approved
0.6695	Remote Similarity	NPD5891	Approved
0.6683	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8409	Suspended
0.6652	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.665	Remote Similarity	NPD2511	Approved
0.6638	Remote Similarity	NPD7707	Approved
0.6621	Remote Similarity	NPD2307	Discontinued
0.6619	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4086	Phase 1
0.6606	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.66	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7708	Approved
0.6575	Remote Similarity	NPD4427	Phase 2
0.6574	Remote Similarity	NPD7233	Approved
0.6574	Remote Similarity	NPD7234	Approved
0.6567	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6176	Phase 1
0.6555	Remote Similarity	NPD4952	Phase 3
0.6552	Remote Similarity	NPD2581	Approved
0.6552	Remote Similarity	NPD2582	Approved
0.6549	Remote Similarity	NPD7803	Approved
0.6545	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD8160	Phase 2
0.6533	Remote Similarity	NPD6987	Phase 1
0.6528	Remote Similarity	NPD4948	Discontinued
0.652	Remote Similarity	NPD8370	Discontinued
0.6516	Remote Similarity	NPD6790	Phase 1
0.6509	Remote Similarity	NPD4989	Phase 2
0.6507	Remote Similarity	NPD7470	Discontinued
0.6496	Remote Similarity	NPD1996	Discontinued
0.6489	Remote Similarity	NPD5513	Phase 2
0.6484	Remote Similarity	NPD6665	Discontinued
0.6484	Remote Similarity	NPD4376	Phase 3
0.6478	Remote Similarity	NPD7069	Discontinued
0.6476	Remote Similarity	NPD3371	Approved
0.6473	Remote Similarity	NPD4373	Phase 2
0.6471	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD8063	Discontinued
0.6466	Remote Similarity	NPD5482	Discontinued
0.6458	Remote Similarity	NPD7688	Phase 1
0.6452	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD3178	Discontinued
0.6435	Remote Similarity	NPD4889	Approved
0.6432	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4500	Approved
0.6429	Remote Similarity	NPD4501	Approved
0.6426	Remote Similarity	NPD4369	Phase 2
0.6422	Remote Similarity	NPD6026	Approved
0.6417	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7404	Approved
0.6382	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD2896	Discontinued
0.6376	Remote Similarity	NPD8423	Phase 2
0.6376	Remote Similarity	NPD8399	Phase 1
0.6372	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8356	Approved
0.6371	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD5003	Discontinued
0.636	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.636	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD1630	Approved
0.6356	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD7956	Approved
0.6353	Remote Similarity	NPD7955	Approved
0.6345	Remote Similarity	NPD4804	Approved
0.6345	Remote Similarity	NPD8375	Approved
0.6341	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.634	Remote Similarity	NPD1926	Approved
0.6336	Remote Similarity	NPD5866	Approved
0.6326	Remote Similarity	NPD1643	Phase 3
0.6323	Remote Similarity	NPD6226	Phase 3
0.6322	Remote Similarity	NPD6962	Phase 2
0.6318	Remote Similarity	NPD4499	Approved
0.6318	Remote Similarity	NPD3925	Approved
0.6316	Remote Similarity	NPD5901	Discontinued
0.6316	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD1032	Phase 2
0.6306	Remote Similarity	NPD4529	Approved
0.6306	Remote Similarity	NPD4526	Approved
0.6306	Remote Similarity	NPD4528	Approved
0.6304	Remote Similarity	NPD7467	Discontinued
0.6303	Remote Similarity	NPD1575	Approved
0.6303	Remote Similarity	NPD1573	Approved
0.6301	Remote Similarity	NPD6825	Phase 1
0.6301	Remote Similarity	NPD8021	Approved
0.6301	Remote Similarity	NPD8020	Approved
0.6295	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD8289	Discontinued
0.6292	Remote Similarity	NPD5640	Discontinued
0.6288	Remote Similarity	NPD7001	Phase 3
0.6283	Remote Similarity	NPD6479	Discontinued
0.6282	Remote Similarity	NPD5293	Phase 2
0.6281	Remote Similarity	NPD4805	Approved
0.6281	Remote Similarity	NPD8374	Phase 3
0.6281	Remote Similarity	NPD5022	Discontinued
0.6274	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4334	Discontinued
0.6271	Remote Similarity	NPD4429	Discontinued
0.6268	Remote Similarity	NPD1631	Approved
0.6266	Remote Similarity	NPD8430	Approved
0.6261	Remote Similarity	NPD7562	Approved
0.6261	Remote Similarity	NPD6298	Discontinued
0.625	Remote Similarity	NPD5899	Approved
0.625	Remote Similarity	NPD5897	Approved
0.625	Remote Similarity	NPD5898	Approved
0.625	Remote Similarity	NPD7576	Discontinued
0.625	Remote Similarity	NPD5072	Discontinued
0.6245	Remote Similarity	NPD8329	Phase 3
0.6244	Remote Similarity	NPD2564	Approved
0.6244	Remote Similarity	NPD2565	Phase 2
0.624	Remote Similarity	NPD7967	Discontinued
0.6239	Remote Similarity	NPD721	Approved
0.6239	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5888	Phase 2
0.6239	Remote Similarity	NPD1096	Discontinued
0.6234	Remote Similarity	NPD6995	Phase 1
0.6233	Remote Similarity	NPD6361	Phase 2
0.6231	Remote Similarity	NPD5450	Discontinued
0.6228	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD6791	Phase 2
0.6223	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD8485	Approved
0.6218	Remote Similarity	NPD6242	Discontinued
0.6215	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD203	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD3259	Approved
0.6197	Remote Similarity	NPD8097	Phase 3
0.6197	Remote Similarity	NPD8096	Phase 3
0.6195	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD4923	Phase 1
0.619	Remote Similarity	NPD6276	Discontinued
0.6187	Remote Similarity	NPD8091	Phase 3
0.6186	Remote Similarity	NPD3238	Discontinued
0.6186	Remote Similarity	NPD7496	Phase 2
0.6186	Remote Similarity	NPD5490	Discontinued
0.6182	Remote Similarity	NPD5444	Phase 1
0.618	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.618	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD1343	Approved
0.6178	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD8283	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