NPASS Compound

Structure

NPC51008 OpenBabel07101718302D 60 65 0 0 1 0 0 0 0 0999 V2000 5.8806 3.4702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8824 3.7153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7723 3.0443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3802 -2.9864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0431 -2.9279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8537 -1.0559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9261 -0.0886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7937 0.9220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9579 -1.3859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9318 3.2685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4929 -4.7215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2040 -4.0617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5660 -4.4356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4738 -2.9581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9881 -3.1161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3501 -3.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6338 -2.4731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1777 1.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7569 2.0399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3139 -2.4731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4738 -1.0180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 -0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0849 3.7878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0612 3.7041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9266 -2.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2814 -2.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0612 -2.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6338 -1.5031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6313 0.3645 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2104 2.1124 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6321 2.3460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4610 0.9220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3360 0.4370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3835 1.2217 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7026 1.5268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8453 -1.8844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7937 -1.0180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7026 -0.6528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0522 -0.5095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9537 0.4370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7569 -0.4370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7569 1.3109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4610 -0.0480 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3139 -1.5031 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5058 4.6618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2770 4.6498 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8939 -2.2574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3804 -2.6867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2811 1.6251 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5564 -1.2247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9537 -1.5031 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 0.6313 2.9864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1343 3.4182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6832 2.1443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9184 -1.5985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5058 -1.3109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5600 -0.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7937 -0.0480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 40 1 0 0 0 0 7 40 1 0 0 0 0 10 32 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 28 2 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 19 2 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 45 2 0 0 0 0 21 29 2 0 0 0 0 21 45 1 0 0 0 0 22 41 1 0 0 0 0 22 44 1 0 0 0 0 23 53 1 0 0 0 0 24 46 2 0 0 0 0 24 54 1 0 0 0 0 25 47 2 0 0 0 0 25 55 1 0 0 0 0 26 48 2 0 0 0 0 26 58 1 0 0 0 0 27 49 2 0 0 0 0 27 59 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 30 34 1 0 0 0 0 30 40 1 1 0 0 0 31 43 1 1 0 0 0 31 54 1 0 0 0 0 32 50 2 0 0 0 0 32 56 1 0 0 0 0 33 35 1 0 0 0 0 33 36 1 0 0 0 0 33 44 1 1 0 0 0 34 42 1 6 0 0 0 34 43 1 0 0 0 0 35 41 1 1 0 0 0 35 56 1 0 0 0 0 36 43 1 6 0 0 0 36 55 1 0 0 0 0 37 51 2 0 0 0 0 37 57 1 0 0 0 0 38 52 2 0 0 0 0 38 60 1 0 0 0 0 39 42 1 6 0 0 0 39 44 1 0 0 0 0 39 57 1 0 0 0 0 40 58 1 0 0 0 0 41 8 1 1 0 0 0 41 60 1 0 0 0 0 42 9 1 1 0 0 0 42 53 1 0 0 0 0 43 23 1 6 0 0 0 44 59 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	833.33
Volume:	824.181
LogP:	3.76
LogD:	1.643
LogS:	-3.99
# Rotatable Bonds:	18
TPSA:	206.22
# H-Bond Aceptor:	16
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	6.429
Fsp3:	0.545
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:	-5.304
MDCK Permeability:	9.997211600420997e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.745
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.765

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	60.04685974121094%
Volume Distribution (VD):	1.812
Pgp-substrate:	19.968658447265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.249
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.57
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	2.908
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.569
Human Hepatotoxicity (H-HT):	0.991
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.132
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC51008

Natural Product ID:	NPC51008
*Common Name:**	Euphorbialoid I
IUPAC Name:	n.a.
Synonyms:	euphorbialoid I
Standard InCHIKey:	XZCDGDWVEIWADN-DHPBHSDQSA-N
Standard InCHI:	InChI=1S/C44H51NO15/c1-10-32(50)56-35-33-36(55-25(3)47)43-23-53-42(9,34(43)30(40(6,7)58-26(4)48)18-19-31(43)54-24(2)46)39(57-37(51)28-15-12-11-13-16-28)44(33,59-27(5)49)22-41(35,8)60-38(52)29-17-14-20-45-21-29/h11-21,30-31,33-36,39H,10,22-23H2,1-9H3/t30-,31+,33+,34-,35+,36+,39+,41+,42+,43+,44+/m0/s1
SMILES:	CCC(=O)O[C@@H]1[C@@H]2[C@@H](OC(=O)C)[C@]34CO[C@@]([C@H]([C@]2(C[C@@]1(C)OC(=O)c1cccnc1)OC(=O)C)OC(=O)c1ccccc1)([C@@H]4[C@H](C=C[C@H]3OC(=O)C)C(OC(=O)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2030587
PubChem CID:	70689979
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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	=	41300.0	nM	PMID[565948]

☑ 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 NPC51008 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	391
0.1-0.2	1545
0.2-0.3	4664
0.3-0.4	14804
0.4-0.5	15845
0.5-0.6	4266
0.6-0.7	942
0.7-0.8	138
0.8-0.85	71
0.85-0.9	22
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC41724
0.9947	High Similarity	NPC280473
0.9947	High Similarity	NPC323551
0.9585	High Similarity	NPC165837
0.9487	High Similarity	NPC62844
0.9487	High Similarity	NPC193361
0.9433	High Similarity	NPC476467
0.9184	High Similarity	NPC470189
0.9184	High Similarity	NPC40919
0.91	High Similarity	NPC187494
0.91	High Similarity	NPC319556
0.9034	High Similarity	NPC213143
0.9031	High Similarity	NPC470190
0.902	High Similarity	NPC233727
0.9	High Similarity	NPC207531
0.8856	High Similarity	NPC4421
0.8841	High Similarity	NPC285411
0.8841	High Similarity	NPC14116
0.881	High Similarity	NPC238278
0.8798	High Similarity	NPC134384
0.8798	High Similarity	NPC311196
0.8762	High Similarity	NPC264674
0.8725	High Similarity	NPC473115
0.8725	High Similarity	NPC6576
0.8725	High Similarity	NPC62367
0.8725	High Similarity	NPC212768
0.8725	High Similarity	NPC473089
0.8725	High Similarity	NPC75600
0.8725	High Similarity	NPC158020
0.8689	High Similarity	NPC477903
0.8683	High Similarity	NPC216428
0.8683	High Similarity	NPC84815
0.8683	High Similarity	NPC301368
0.8676	High Similarity	NPC471016
0.8663	High Similarity	NPC472553
0.8647	High Similarity	NPC235364
0.8641	High Similarity	NPC477901
0.8627	High Similarity	NPC470306
0.8627	High Similarity	NPC477909
0.8627	High Similarity	NPC477907
0.8627	High Similarity	NPC42678
0.8599	High Similarity	NPC477912
0.8585	High Similarity	NPC6981
0.8585	High Similarity	NPC471014
0.8585	High Similarity	NPC475408
0.8565	High Similarity	NPC477900
0.8565	High Similarity	NPC26881
0.8565	High Similarity	NPC477902
0.8565	High Similarity	NPC477899
0.8558	High Similarity	NPC127720
0.8558	High Similarity	NPC477788
0.8558	High Similarity	NPC127026
0.8544	High Similarity	NPC144779
0.8544	High Similarity	NPC294579
0.8524	High Similarity	NPC148860
0.8517	High Similarity	NPC471980
0.8515	High Similarity	NPC304179
0.8515	High Similarity	NPC48042
0.8515	High Similarity	NPC472550
0.8502	High Similarity	NPC472555
0.8488	Intermediate Similarity	NPC319128
0.8483	Intermediate Similarity	NPC124029
0.8476	Intermediate Similarity	NPC328154
0.8447	Intermediate Similarity	NPC477910
0.8429	Intermediate Similarity	NPC57797
0.8429	Intermediate Similarity	NPC76565
0.8429	Intermediate Similarity	NPC250807
0.8424	Intermediate Similarity	NPC472752
0.8406	Intermediate Similarity	NPC477908
0.8406	Intermediate Similarity	NPC206343
0.8404	Intermediate Similarity	NPC91125
0.8398	Intermediate Similarity	NPC228331
0.8396	Intermediate Similarity	NPC122968
0.8396	Intermediate Similarity	NPC87152
0.8396	Intermediate Similarity	NPC476110
0.8396	Intermediate Similarity	NPC475631
0.8396	Intermediate Similarity	NPC228377
0.8396	Intermediate Similarity	NPC475600
0.8396	Intermediate Similarity	NPC328186
0.8396	Intermediate Similarity	NPC477787
0.8396	Intermediate Similarity	NPC211920
0.8389	Intermediate Similarity	NPC473850
0.8389	Intermediate Similarity	NPC475137
0.8389	Intermediate Similarity	NPC475498
0.8381	Intermediate Similarity	NPC477911
0.8374	Intermediate Similarity	NPC63041
0.8364	Intermediate Similarity	NPC477906
0.8357	Intermediate Similarity	NPC470486
0.8357	Intermediate Similarity	NPC471977
0.8357	Intermediate Similarity	NPC471190
0.8357	Intermediate Similarity	NPC475644
0.831	Intermediate Similarity	NPC475601
0.831	Intermediate Similarity	NPC146824
0.8279	Intermediate Similarity	NPC475303
0.8279	Intermediate Similarity	NPC96801
0.8279	Intermediate Similarity	NPC316841
0.8279	Intermediate Similarity	NPC475596
0.8279	Intermediate Similarity	NPC150698
0.8279	Intermediate Similarity	NPC292416
0.8279	Intermediate Similarity	NPC473689
0.8271	Intermediate Similarity	NPC475362
0.8263	Intermediate Similarity	NPC473506
0.8241	Intermediate Similarity	NPC30456
0.8241	Intermediate Similarity	NPC319880
0.8241	Intermediate Similarity	NPC244839
0.8241	Intermediate Similarity	NPC320324
0.8227	Intermediate Similarity	NPC289086
0.8209	Intermediate Similarity	NPC470279
0.8203	Intermediate Similarity	NPC237702
0.8165	Intermediate Similarity	NPC475406
0.8165	Intermediate Similarity	NPC327769
0.8157	Intermediate Similarity	NPC469748
0.8128	Intermediate Similarity	NPC38959
0.8128	Intermediate Similarity	NPC327904
0.8082	Intermediate Similarity	NPC475426
0.8082	Intermediate Similarity	NPC170751
0.8082	Intermediate Similarity	NPC35208
0.8018	Intermediate Similarity	NPC253482
0.7952	Intermediate Similarity	NPC292517
0.7923	Intermediate Similarity	NPC309498
0.7911	Intermediate Similarity	NPC475648
0.7841	Intermediate Similarity	NPC475533
0.784	Intermediate Similarity	NPC30570
0.7822	Intermediate Similarity	NPC103230
0.7807	Intermediate Similarity	NPC475315
0.7807	Intermediate Similarity	NPC324619
0.7804	Intermediate Similarity	NPC162812
0.7799	Intermediate Similarity	NPC475835
0.7797	Intermediate Similarity	NPC180668
0.7797	Intermediate Similarity	NPC471013
0.7797	Intermediate Similarity	NPC148896
0.7719	Intermediate Similarity	NPC476090
0.7682	Intermediate Similarity	NPC475301
0.7682	Intermediate Similarity	NPC85879
0.7682	Intermediate Similarity	NPC53255
0.7682	Intermediate Similarity	NPC326930
0.767	Intermediate Similarity	NPC324245
0.767	Intermediate Similarity	NPC320748
0.7668	Intermediate Similarity	NPC471004
0.7662	Intermediate Similarity	NPC10904
0.765	Intermediate Similarity	NPC13603
0.7644	Intermediate Similarity	NPC328559
0.7644	Intermediate Similarity	NPC32451
0.7639	Intermediate Similarity	NPC471015
0.7617	Intermediate Similarity	NPC111732
0.7596	Intermediate Similarity	NPC79223
0.7553	Intermediate Similarity	NPC473833
0.7536	Intermediate Similarity	NPC329024
0.7513	Intermediate Similarity	NPC107287
0.749	Intermediate Similarity	NPC471978
0.749	Intermediate Similarity	NPC328928
0.7465	Intermediate Similarity	NPC156044
0.7464	Intermediate Similarity	NPC123395
0.7451	Intermediate Similarity	NPC44354
0.7416	Intermediate Similarity	NPC59033
0.7416	Intermediate Similarity	NPC317672
0.7411	Intermediate Similarity	NPC249614
0.7397	Intermediate Similarity	NPC471979
0.7374	Intermediate Similarity	NPC191310
0.7371	Intermediate Similarity	NPC12944
0.7371	Intermediate Similarity	NPC25442
0.7364	Intermediate Similarity	NPC141385
0.7363	Intermediate Similarity	NPC317010
0.7359	Intermediate Similarity	NPC37473
0.7356	Intermediate Similarity	NPC135950
0.7343	Intermediate Similarity	NPC471546
0.7304	Intermediate Similarity	NPC282103
0.7302	Intermediate Similarity	NPC112741
0.7299	Intermediate Similarity	NPC103361
0.723	Intermediate Similarity	NPC155792
0.7189	Intermediate Similarity	NPC470280
0.7171	Intermediate Similarity	NPC207851
0.7156	Intermediate Similarity	NPC109922
0.7136	Intermediate Similarity	NPC318299
0.7129	Intermediate Similarity	NPC138370
0.7123	Intermediate Similarity	NPC314834
0.7104	Intermediate Similarity	NPC317752
0.7067	Intermediate Similarity	NPC325775
0.7067	Intermediate Similarity	NPC328798
0.7059	Intermediate Similarity	NPC164340
0.7056	Intermediate Similarity	NPC160127
0.7056	Intermediate Similarity	NPC50997
0.7044	Intermediate Similarity	NPC84347
0.7039	Intermediate Similarity	NPC327373
0.7035	Intermediate Similarity	NPC253314
0.7027	Intermediate Similarity	NPC229348
0.7024	Intermediate Similarity	NPC471997
0.7014	Intermediate Similarity	NPC55493
0.7	Intermediate Similarity	NPC469489
0.6986	Remote Similarity	NPC315545
0.6986	Remote Similarity	NPC314297
0.6968	Remote Similarity	NPC123839
0.6963	Remote Similarity	NPC230085
0.6963	Remote Similarity	NPC159630
0.6948	Remote Similarity	NPC476205
0.6948	Remote Similarity	NPC476129
0.6948	Remote Similarity	NPC476212
0.6948	Remote Similarity	NPC476207
0.6948	Remote Similarity	NPC476206
0.6948	Remote 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 NPC51008 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	580
0.2-0.3	711
0.3-0.4	2001
0.4-0.5	3462
0.5-0.6	1851
0.6-0.7	298
0.7-0.8	9
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8413	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD7396	Approved
0.7672	Intermediate Similarity	NPD820	Phase 3
0.7532	Intermediate Similarity	NPD8468	Phase 2
0.743	Intermediate Similarity	NPD2509	Approved
0.743	Intermediate Similarity	NPD2510	Approved
0.7356	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD9271	Approved
0.729	Intermediate Similarity	NPD3947	Discontinued
0.7273	Intermediate Similarity	NPD3389	Approved
0.7273	Intermediate Similarity	NPD3393	Approved
0.7273	Intermediate Similarity	NPD3394	Approved
0.726	Intermediate Similarity	NPD3795	Approved
0.726	Intermediate Similarity	NPD3794	Approved
0.7248	Intermediate Similarity	NPD4417	Approved
0.7245	Intermediate Similarity	NPD6635	Approved
0.7243	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4506	Discontinued
0.7176	Intermediate Similarity	NPD7010	Phase 3
0.717	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6529	Discontinued
0.713	Intermediate Similarity	NPD2831	Approved
0.7098	Intermediate Similarity	NPD6770	Approved
0.7065	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4301	Approved
0.7014	Intermediate Similarity	NPD5475	Discontinued
0.7009	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8326	Phase 3
0.7009	Intermediate Similarity	NPD8325	Phase 3
0.6991	Remote Similarity	NPD3280	Approved
0.6985	Remote Similarity	NPD5088	Discontinued
0.6984	Remote Similarity	NPD107	Approved
0.6966	Remote Similarity	NPD5891	Approved
0.6949	Remote Similarity	NPD7885	Phase 2
0.6949	Remote Similarity	NPD7886	Phase 2
0.6916	Remote Similarity	NPD8479	Phase 2
0.6906	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD9075	Approved
0.6839	Remote Similarity	NPD9074	Approved
0.6822	Remote Similarity	NPD3006	Discontinued
0.6808	Remote Similarity	NPD2336	Approved
0.6792	Remote Similarity	NPD7233	Approved
0.6792	Remote Similarity	NPD7234	Approved
0.6784	Remote Similarity	NPD2581	Approved
0.6784	Remote Similarity	NPD2582	Approved
0.6776	Remote Similarity	NPD4376	Phase 3
0.6774	Remote Similarity	NPD7777	Approved
0.6774	Remote Similarity	NPD7778	Approved
0.6774	Remote Similarity	NPD53	Approved
0.6773	Remote Similarity	NPD6176	Phase 1
0.6769	Remote Similarity	NPD1270	Approved
0.6763	Remote Similarity	NPD6641	Approved
0.6763	Remote Similarity	NPD6642	Approved
0.6761	Remote Similarity	NPD8063	Discontinued
0.6759	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3371	Approved
0.6756	Remote Similarity	NPD7069	Discontinued
0.6754	Remote Similarity	NPD7878	Phase 2
0.6745	Remote Similarity	NPD4948	Discontinued
0.6745	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6987	Phase 1
0.673	Remote Similarity	NPD4889	Approved
0.6723	Remote Similarity	NPD7688	Phase 1
0.6716	Remote Similarity	NPD2511	Approved
0.6713	Remote Similarity	NPD4427	Phase 2
0.6711	Remote Similarity	NPD7470	Discontinued
0.6711	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7707	Approved
0.6696	Remote Similarity	NPD1996	Discontinued
0.6682	Remote Similarity	NPD2307	Discontinued
0.6681	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.668	Remote Similarity	NPD1483	Discontinued
0.6667	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD5482	Discontinued
0.6652	Remote Similarity	NPD7404	Approved
0.665	Remote Similarity	NPD6026	Approved
0.6638	Remote Similarity	NPD4989	Phase 2
0.6637	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5513	Phase 2
0.6615	Remote Similarity	NPD2896	Discontinued
0.661	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6226	Phase 3
0.6605	Remote Similarity	NPD4499	Approved
0.6594	Remote Similarity	NPD8160	Phase 2
0.6592	Remote Similarity	NPD5901	Discontinued
0.6592	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4528	Approved
0.659	Remote Similarity	NPD4529	Approved
0.659	Remote Similarity	NPD4526	Approved
0.6589	Remote Similarity	NPD8020	Approved
0.6589	Remote Similarity	NPD8021	Approved
0.6578	Remote Similarity	NPD7467	Discontinued
0.657	Remote Similarity	NPD6790	Phase 1
0.6561	Remote Similarity	NPD4501	Approved
0.6561	Remote Similarity	NPD4500	Approved
0.6561	Remote Similarity	NPD6479	Discontinued
0.6557	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD5640	Discontinued
0.6553	Remote Similarity	NPD8289	Discontinued
0.6544	Remote Similarity	NPD6665	Discontinued
0.6533	Remote Similarity	NPD7562	Approved
0.6529	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6298	Discontinued
0.6518	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD8409	Suspended
0.6514	Remote Similarity	NPD6361	Phase 2
0.6513	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6791	Phase 2
0.6509	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3178	Discontinued
0.6508	Remote Similarity	NPD7708	Approved
0.6507	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD1630	Approved
0.6502	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5003	Discontinued
0.6496	Remote Similarity	NPD8356	Approved
0.6496	Remote Similarity	NPD6995	Phase 1
0.6495	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7001	Phase 3
0.6486	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4952	Phase 3
0.6471	Remote Similarity	NPD5022	Discontinued
0.6471	Remote Similarity	NPD7803	Approved
0.6466	Remote Similarity	NPD4429	Discontinued
0.6463	Remote Similarity	NPD5866	Approved
0.645	Remote Similarity	NPD5490	Discontinued
0.6447	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD1032	Phase 2
0.6442	Remote Similarity	NPD1573	Approved
0.6442	Remote Similarity	NPD1575	Approved
0.6441	Remote Similarity	NPD6999	Discontinued
0.6441	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6276	Discontinued
0.6435	Remote Similarity	NPD5888	Phase 2
0.6432	Remote Similarity	NPD8423	Phase 2
0.6432	Remote Similarity	NPD3386	Phase 2
0.6432	Remote Similarity	NPD8399	Phase 1
0.6423	Remote Similarity	NPD7967	Discontinued
0.6419	Remote Similarity	NPD6241	Phase 1
0.6413	Remote Similarity	NPD6219	Discontinued
0.6411	Remote Similarity	NPD4369	Phase 2
0.641	Remote Similarity	NPD6242	Discontinued
0.641	Remote Similarity	NPD4804	Approved
0.6408	Remote Similarity	NPD1631	Approved
0.6407	Remote Similarity	NPD5293	Phase 2
0.6406	Remote Similarity	NPD5450	Discontinued
0.6406	Remote Similarity	NPD4334	Discontinued
0.6403	Remote Similarity	NPD7956	Approved
0.6403	Remote Similarity	NPD7955	Approved
0.6398	Remote Similarity	NPD3238	Discontinued
0.6394	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD3922	Approved
0.6393	Remote Similarity	NPD3924	Approved
0.6393	Remote Similarity	NPD3923	Approved
0.6393	Remote Similarity	NPD3921	Approved
0.639	Remote Similarity	NPD4373	Phase 2
0.6387	Remote Similarity	NPD8430	Approved
0.6386	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4923	Phase 1
0.6381	Remote Similarity	NPD2076	Approved
0.6381	Remote Similarity	NPD2077	Approved
0.638	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD5072	Discontinued
0.6376	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6962	Phase 2
0.6372	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD3925	Approved
0.6368	Remote Similarity	NPD2753	Discontinued
0.6367	Remote Similarity	NPD7417	Discontinued
0.6367	Remote Similarity	NPD7576	Discontinued
0.6364	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1173	Approved
0.6364	Remote Similarity	NPD3813	Approved
0.6355	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6825	Phase 1
0.6351	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6446	Discontinued
0.6345	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD4805	Approved
0.6344	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7944	Discontinued
0.6326	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5632	Approved
0.6325	Remote Similarity	NPD3354	Phase 2
0.6325	Remote Similarity	NPD1926	Approved
0.6325	Remote Similarity	NPD6578	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