NPASS Compound

Structure

NPC473506 OpenBabel07101718332D 58 63 0 0 1 0 0 0 0 0999 V2000 3.6818 1.5737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8693 0.6217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7436 4.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1613 -1.7342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9824 -2.9447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5303 2.3691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7051 1.2907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7858 -1.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9524 1.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0099 0.5424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0747 1.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4722 2.7711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1898 0.0025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2545 1.4230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9813 2.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9546 2.4829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4547 1.4672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7789 1.1877 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.8875 0.6364 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.1696 3.5526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8291 -1.0144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0306 -2.7035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1982 1.6493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3121 0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9729 1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1965 1.0453 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4554 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3127 -1.2739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4894 1.0453 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5824 0.1424 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9345 -0.6349 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4483 -1.0549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0485 0.4925 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7624 0.0885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4919 -0.0972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4150 2.0026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2185 0.9573 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3748 -0.6853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2059 -0.1968 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8429 -0.5036 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9462 1.9210 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1488 3.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7864 -1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6543 -3.4072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1555 1.8678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5797 -2.2188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6534 -0.3243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5495 -1.0774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3270 2.9806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7607 -1.5882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8780 1.8370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0634 1.9300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5397 -0.0761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2365 -1.7586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9088 0.7110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4253 -0.3612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6143 0.3431 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 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 8 38 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 24 2 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 41 2 0 0 0 0 17 37 1 0 0 0 0 17 51 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 0 0 0 0 19 34 1 0 0 0 0 20 42 2 0 0 0 0 20 52 1 0 0 0 0 21 43 2 0 0 0 0 21 53 1 0 0 0 0 22 44 2 0 0 0 0 22 54 1 0 0 0 0 23 45 2 0 0 0 0 23 55 1 0 0 0 0 24 35 1 0 0 0 0 25 27 2 0 0 0 0 25 36 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 26 37 1 1 0 0 0 27 41 1 0 0 0 0 28 31 1 0 0 0 0 28 32 1 0 0 0 0 28 46 1 6 0 0 0 29 33 1 0 0 0 0 29 52 1 6 0 0 0 30 40 1 1 0 0 0 30 53 1 0 0 0 0 31 38 1 1 0 0 0 31 56 1 0 0 0 0 32 39 1 6 0 0 0 32 54 1 0 0 0 0 33 39 1 6 0 0 0 33 55 1 0 0 0 0 34 47 2 0 0 0 0 34 56 1 0 0 0 0 35 48 2 0 0 0 0 35 57 1 0 0 0 0 36 49 2 0 0 0 0 36 51 1 0 0 0 0 37 7 1 6 0 0 0 37 58 1 0 0 0 0 38 40 1 6 0 0 0 38 50 1 0 0 0 0 39 40 1 6 0 0 0 39 57 1 0 0 0 0 40 58 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	811.27
Volume:	775.214
LogP:	1.825
LogD:	1.173
LogS:	-3.773
# Rotatable Bonds:	11
TPSA:	246.68
# H-Bond Aceptor:	18
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	7.577
Fsp3:	0.55
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:	-5.311
MDCK Permeability:	0.0001258432457689196
Pgp-inhibitor:	1.0
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.657
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	45.97049331665039%
Volume Distribution (VD):	1.452
Pgp-substrate:	25.33770751953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.019
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.1
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.327
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.691
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	3.068
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.991
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.08
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC473506

Natural Product ID:	NPC473506
*Common Name:**	XWKAQZKNPBZWNK-RMJHFGBWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XWKAQZKNPBZWNK-RMJHFGBWSA-N
Standard InCHI:	InChI=1S/C40H45NO17/c1-18-19(2)34(47)56-31-28(46)32(54-22(5)44)39(57-35(48)24-13-10-9-11-14-24)33(55-23(6)45)29(52-20(3)42)26-30(53-21(4)43)40(39,38(31,8)50)58-37(26,7)17-51-36(49)25-15-12-16-41-27(18)25/h9-16,18-19,26,28-33,46,50H,17H2,1-8H3/t18?,19?,26-,28+,29-,30-,31+,32+,33-,37+,38+,39-,40+/m1/s1
SMILES:	CC1C(C(=O)OC2C(C(C3(C(C(C4C(C3(C2(C)O)OC4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C6=CC=CC=C6)OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444119
PubChem CID:	44575771
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids 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
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO14242	Maytenus laevis	Species	Celastraceae	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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	110.1	pg/ml	PMID[521290]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	136.1	pg/ml	PMID[521290]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[521290]

☑ 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 NPC473506 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	335
0.1-0.2	1422
0.2-0.3	3432
0.3-0.4	10895
0.4-0.5	17730
0.5-0.6	6382
0.6-0.7	2125
0.7-0.8	215
0.8-0.85	29
0.85-0.9	41
0.9-0.95	62
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
0.9901	High Similarity	NPC475644
0.9901	High Similarity	NPC471977
0.9901	High Similarity	NPC470486
0.9901	High Similarity	NPC471190
0.9851	High Similarity	NPC475600
0.9851	High Similarity	NPC475631
0.9851	High Similarity	NPC476110
0.9851	High Similarity	NPC87152
0.9756	High Similarity	NPC30456
0.9752	High Similarity	NPC475498
0.9752	High Similarity	NPC475137
0.9707	High Similarity	NPC475303
0.9707	High Similarity	NPC475596
0.9703	High Similarity	NPC76565
0.9657	High Similarity	NPC228377
0.9657	High Similarity	NPC328186
0.9657	High Similarity	NPC122968
0.9657	High Similarity	NPC477787
0.9614	High Similarity	NPC237702
0.9612	High Similarity	NPC473689
0.9612	High Similarity	NPC292416
0.9567	High Similarity	NPC327769
0.9565	High Similarity	NPC244839
0.9565	High Similarity	NPC319880
0.9565	High Similarity	NPC320324
0.9559	High Similarity	NPC473850
0.9517	High Similarity	NPC316841
0.9515	High Similarity	NPC475362
0.951	High Similarity	NPC250807
0.951	High Similarity	NPC57797
0.9505	High Similarity	NPC301368
0.9505	High Similarity	NPC84815
0.9474	High Similarity	NPC170751
0.9474	High Similarity	NPC475406
0.9466	High Similarity	NPC146824
0.9461	High Similarity	NPC477788
0.9455	High Similarity	NPC144779
0.9455	High Similarity	NPC294579
0.9429	High Similarity	NPC38959
0.9429	High Similarity	NPC327904
0.9415	High Similarity	NPC471980
0.9406	High Similarity	NPC6981
0.9406	High Similarity	NPC471014
0.9406	High Similarity	NPC471016
0.9406	High Similarity	NPC475408
0.9369	High Similarity	NPC328154
0.9366	High Similarity	NPC127720
0.9366	High Similarity	NPC127026
0.9356	High Similarity	NPC470306
0.9307	High Similarity	NPC4421
0.9296	High Similarity	NPC253482
0.9289	High Similarity	NPC35208
0.9289	High Similarity	NPC475426
0.9265	High Similarity	NPC62367
0.922	High Similarity	NPC216428
0.9187	High Similarity	NPC211920
0.9183	High Similarity	NPC477902
0.9171	High Similarity	NPC158020
0.9171	High Similarity	NPC6576
0.9171	High Similarity	NPC212768
0.9171	High Similarity	NPC75600
0.9171	High Similarity	NPC473115
0.9171	High Similarity	NPC473089
0.9167	High Similarity	NPC477907
0.9167	High Similarity	NPC477909
0.9167	High Similarity	NPC475648
0.9167	High Similarity	NPC42678
0.9147	High Similarity	NPC150698
0.9147	High Similarity	NPC96801
0.913	High Similarity	NPC477912
0.9095	High Similarity	NPC124029
0.902	High Similarity	NPC472553
0.9005	High Similarity	NPC475601
0.8957	High Similarity	NPC148860
0.8947	High Similarity	NPC477903
0.8942	High Similarity	NPC472555
0.8925	High Similarity	NPC469748
0.8889	High Similarity	NPC477910
0.8879	High Similarity	NPC477906
0.8873	High Similarity	NPC304179
0.8873	High Similarity	NPC48042
0.8873	High Similarity	NPC472550
0.8846	High Similarity	NPC206343
0.8846	High Similarity	NPC477908
0.8841	High Similarity	NPC319128
0.8841	High Similarity	NPC264674
0.8824	High Similarity	NPC63041
0.8815	High Similarity	NPC477911
0.875	High Similarity	NPC228331
0.8732	High Similarity	NPC477899
0.8732	High Similarity	NPC477900
0.8726	High Similarity	NPC235364
0.8717	High Similarity	NPC326930
0.8717	High Similarity	NPC475301
0.8645	High Similarity	NPC26881
0.8632	High Similarity	NPC477901
0.8596	High Similarity	NPC13603
0.8571	High Similarity	NPC328928
0.8565	High Similarity	NPC476467
0.8565	High Similarity	NPC473833
0.8553	High Similarity	NPC53255
0.8553	High Similarity	NPC85879
0.8491	Intermediate Similarity	NPC471978
0.8486	Intermediate Similarity	NPC91125
0.8407	Intermediate Similarity	NPC475533
0.8394	Intermediate Similarity	NPC285411
0.8394	Intermediate Similarity	NPC14116
0.837	Intermediate Similarity	NPC324619
0.837	Intermediate Similarity	NPC475315
0.8363	Intermediate Similarity	NPC476090
0.8356	Intermediate Similarity	NPC311196
0.8356	Intermediate Similarity	NPC134384
0.8305	Intermediate Similarity	NPC471979
0.8302	Intermediate Similarity	NPC280473
0.8302	Intermediate Similarity	NPC323551
0.8288	Intermediate Similarity	NPC238278
0.8282	Intermediate Similarity	NPC148896
0.8282	Intermediate Similarity	NPC180668
0.8282	Intermediate Similarity	NPC471013
0.8268	Intermediate Similarity	NPC471015
0.8263	Intermediate Similarity	NPC51008
0.8263	Intermediate Similarity	NPC41724
0.8246	Intermediate Similarity	NPC472752
0.8243	Intermediate Similarity	NPC213143
0.823	Intermediate Similarity	NPC289086
0.8186	Intermediate Similarity	NPC30570
0.8148	Intermediate Similarity	NPC162812
0.8139	Intermediate Similarity	NPC10904
0.8136	Intermediate Similarity	NPC233727
0.8131	Intermediate Similarity	NPC292517
0.8038	Intermediate Similarity	NPC470279
0.8019	Intermediate Similarity	NPC309498
0.8009	Intermediate Similarity	NPC165837
0.7981	Intermediate Similarity	NPC475835
0.7945	Intermediate Similarity	NPC187494
0.7936	Intermediate Similarity	NPC193361
0.7936	Intermediate Similarity	NPC62844
0.7936	Intermediate Similarity	NPC207531
0.7919	Intermediate Similarity	NPC253314
0.7917	Intermediate Similarity	NPC470189
0.7917	Intermediate Similarity	NPC40919
0.7864	Intermediate Similarity	NPC319556
0.786	Intermediate Similarity	NPC470190
0.783	Intermediate Similarity	NPC32451
0.783	Intermediate Similarity	NPC328559
0.7798	Intermediate Similarity	NPC111732
0.7689	Intermediate Similarity	NPC324245
0.7689	Intermediate Similarity	NPC320748
0.7686	Intermediate Similarity	NPC471004
0.7682	Intermediate Similarity	NPC37473
0.7667	Intermediate Similarity	NPC103230
0.7626	Intermediate Similarity	NPC314834
0.7617	Intermediate Similarity	NPC79223
0.7606	Intermediate Similarity	NPC317672
0.7594	Intermediate Similarity	NPC109922
0.7569	Intermediate Similarity	NPC156044
0.7559	Intermediate Similarity	NPC329024
0.7489	Intermediate Similarity	NPC314297
0.7489	Intermediate Similarity	NPC315545
0.7489	Intermediate Similarity	NPC274842
0.7479	Intermediate Similarity	NPC107123
0.7477	Intermediate Similarity	NPC244856
0.7477	Intermediate Similarity	NPC12944
0.7477	Intermediate Similarity	NPC25442
0.7476	Intermediate Similarity	NPC317010
0.7467	Intermediate Similarity	NPC141385
0.7465	Intermediate Similarity	NPC135950
0.7452	Intermediate Similarity	NPC207851
0.7444	Intermediate Similarity	NPC306644
0.7444	Intermediate Similarity	NPC236424
0.7444	Intermediate Similarity	NPC317752
0.7443	Intermediate Similarity	NPC314855
0.7443	Intermediate Similarity	NPC313345
0.7443	Intermediate Similarity	NPC313796
0.7443	Intermediate Similarity	NPC315638
0.7442	Intermediate Similarity	NPC59033
0.7442	Intermediate Similarity	NPC149708
0.7427	Intermediate Similarity	NPC183537
0.7416	Intermediate Similarity	NPC282103
0.7407	Intermediate Similarity	NPC103361
0.7399	Intermediate Similarity	NPC318299
0.7395	Intermediate Similarity	NPC15406
0.7393	Intermediate Similarity	NPC44354
0.7386	Intermediate Similarity	NPC476516
0.7384	Intermediate Similarity	NPC210296
0.7382	Intermediate Similarity	NPC233334
0.7376	Intermediate Similarity	NPC470280
0.7371	Intermediate Similarity	NPC24019
0.7364	Intermediate Similarity	NPC124313
0.7362	Intermediate Similarity	NPC108342
0.7355	Intermediate Similarity	NPC77878
0.7353	Intermediate Similarity	NPC249614
0.735	Intermediate Similarity	NPC70155
0.7348	Intermediate Similarity	NPC235885
0.7339	Intermediate Similarity	NPC155792
0.7336	Intermediate Similarity	NPC478045
0.7331	Intermediate Similarity	NPC189903
0.7331	Intermediate Similarity	NPC182907
0.7327	Intermediate Similarity	NPC123395
0.7325	Intermediate Similarity	NPC140311

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 NPC473506 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	522
0.2-0.3	634
0.3-0.4	1698
0.4-0.5	3096
0.5-0.6	2237
0.6-0.7	688
0.7-0.8	46
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
0.8489	Intermediate Similarity	NPD8468	Phase 2
0.795	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3794	Approved
0.7763	Intermediate Similarity	NPD3795	Approved
0.7721	Intermediate Similarity	NPD7396	Approved
0.7714	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5891	Approved
0.7546	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2509	Approved
0.7455	Intermediate Similarity	NPD3394	Approved
0.7455	Intermediate Similarity	NPD2510	Approved
0.7455	Intermediate Similarity	NPD3389	Approved
0.7455	Intermediate Similarity	NPD3393	Approved
0.7426	Intermediate Similarity	NPD1483	Discontinued
0.7407	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD3280	Approved
0.7399	Intermediate Similarity	NPD7069	Discontinued
0.7397	Intermediate Similarity	NPD3947	Discontinued
0.7393	Intermediate Similarity	NPD7233	Approved
0.7393	Intermediate Similarity	NPD7234	Approved
0.7352	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8326	Phase 3
0.7345	Intermediate Similarity	NPD8325	Phase 3
0.7345	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7010	Phase 3
0.7281	Intermediate Similarity	NPD7778	Approved
0.7281	Intermediate Similarity	NPD7777	Approved
0.7281	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD53	Approved
0.725	Intermediate Similarity	NPD820	Phase 3
0.724	Intermediate Similarity	NPD6987	Phase 1
0.7237	Intermediate Similarity	NPD7878	Phase 2
0.7222	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD7708	Approved
0.7196	Intermediate Similarity	NPD8063	Discontinued
0.7188	Intermediate Similarity	NPD6529	Discontinued
0.7188	Intermediate Similarity	NPD4506	Discontinued
0.7171	Intermediate Similarity	NPD7803	Approved
0.713	Intermediate Similarity	NPD6770	Approved
0.713	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4417	Approved
0.7124	Intermediate Similarity	NPD5475	Discontinued
0.7108	Intermediate Similarity	NPD7956	Approved
0.7108	Intermediate Similarity	NPD7955	Approved
0.71	Intermediate Similarity	NPD8479	Phase 2
0.7095	Intermediate Similarity	NPD7417	Discontinued
0.7093	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4427	Phase 2
0.7054	Intermediate Similarity	NPD7886	Phase 2
0.7054	Intermediate Similarity	NPD7885	Phase 2
0.7048	Intermediate Similarity	NPD6641	Approved
0.7048	Intermediate Similarity	NPD6642	Approved
0.7043	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8289	Discontinued
0.7019	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD4301	Approved
0.6982	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4948	Discontinued
0.6942	Remote Similarity	NPD6635	Approved
0.6941	Remote Similarity	NPD4528	Approved
0.6941	Remote Similarity	NPD4529	Approved
0.6941	Remote Similarity	NPD4526	Approved
0.6933	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5901	Discontinued
0.6933	Remote Similarity	NPD5022	Discontinued
0.6932	Remote Similarity	NPD8091	Phase 3
0.693	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3006	Discontinued
0.6927	Remote Similarity	NPD2336	Approved
0.6923	Remote Similarity	NPD5003	Discontinued
0.692	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7404	Approved
0.6906	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6962	Phase 2
0.6903	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.69	Remote Similarity	NPD9271	Approved
0.69	Remote Similarity	NPD7470	Discontinued
0.6895	Remote Similarity	NPD4376	Phase 3
0.6894	Remote Similarity	NPD8356	Approved
0.6894	Remote Similarity	NPD6995	Phase 1
0.6885	Remote Similarity	NPD6790	Phase 1
0.6883	Remote Similarity	NPD7707	Approved
0.6883	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6281	Approved
0.687	Remote Similarity	NPD5866	Approved
0.6867	Remote Similarity	NPD7395	Discontinued
0.6857	Remote Similarity	NPD6716	Phase 1
0.6856	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4889	Approved
0.685	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8485	Approved
0.6846	Remote Similarity	NPD4373	Phase 2
0.6844	Remote Similarity	NPD7187	Phase 2
0.6833	Remote Similarity	NPD7688	Phase 1
0.6833	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.683	Remote Similarity	NPD4601	Approved
0.683	Remote Similarity	NPD4600	Approved
0.6828	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7001	Phase 3
0.6828	Remote Similarity	NPD7957	Phase 1
0.6827	Remote Similarity	NPD5482	Discontinued
0.6824	Remote Similarity	NPD4989	Phase 2
0.6818	Remote Similarity	NPD3921	Approved
0.6818	Remote Similarity	NPD3922	Approved
0.6818	Remote Similarity	NPD3923	Approved
0.6818	Remote Similarity	NPD3924	Approved
0.6815	Remote Similarity	NPD6276	Discontinued
0.6808	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7426	Phase 1
0.6807	Remote Similarity	NPD5640	Discontinued
0.6802	Remote Similarity	NPD2307	Discontinued
0.6792	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6999	Discontinued
0.6784	Remote Similarity	NPD2831	Approved
0.6779	Remote Similarity	NPD5088	Discontinued
0.6778	Remote Similarity	NPD8430	Approved
0.6765	Remote Similarity	NPD3925	Approved
0.6757	Remote Similarity	NPD7944	Discontinued
0.6756	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6479	Discontinued
0.6752	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7576	Discontinued
0.6748	Remote Similarity	NPD2581	Approved
0.6748	Remote Similarity	NPD2582	Approved
0.6734	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1575	Approved
0.673	Remote Similarity	NPD1573	Approved
0.6727	Remote Similarity	NPD2565	Phase 2
0.6727	Remote Similarity	NPD8360	Approved
0.6727	Remote Similarity	NPD2564	Approved
0.6727	Remote Similarity	NPD8435	Approved
0.6727	Remote Similarity	NPD8361	Approved
0.6725	Remote Similarity	NPD5429	Discontinued
0.6725	Remote Similarity	NPD7562	Approved
0.6724	Remote Similarity	NPD3816	Phase 1
0.6724	Remote Similarity	NPD3815	Phase 1
0.6723	Remote Similarity	NPD3354	Phase 2
0.6722	Remote Similarity	NPD4952	Phase 3
0.6716	Remote Similarity	NPD9074	Approved
0.6716	Remote Similarity	NPD9075	Approved
0.6713	Remote Similarity	NPD3178	Discontinued
0.6712	Remote Similarity	NPD6361	Phase 2
0.671	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD8160	Phase 2
0.6708	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4086	Phase 1
0.6708	Remote Similarity	NPD7558	Phase 2
0.6708	Remote Similarity	NPD6494	Phase 2
0.6707	Remote Similarity	NPD5488	Discontinued
0.6699	Remote Similarity	NPD6026	Approved
0.6699	Remote Similarity	NPD1631	Approved
0.6698	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8409	Suspended
0.6692	Remote Similarity	NPD8363	Approved
0.6692	Remote Similarity	NPD8364	Approved
0.6683	Remote Similarity	NPD2511	Approved
0.6681	Remote Similarity	NPD5416	Discontinued
0.6681	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.668	Remote Similarity	NPD8463	Approved
0.668	Remote Similarity	NPD6228	Discontinued
0.668	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.668	Remote Similarity	NPD8370	Discontinued
0.6667	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4897	Phase 2
0.6667	Remote Similarity	NPD8467	Approved
0.6667	Remote Similarity	NPD1996	Discontinued
0.6667	Remote Similarity	NPD8465	Approved
0.6667	Remote Similarity	NPD8466	Approved
0.6667	Remote Similarity	NPD6242	Discontinued
0.6653	Remote Similarity	NPD4429	Discontinued
0.6653	Remote Similarity	NPD8102	Discontinued
0.6652	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.664	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3259	Approved
0.6639	Remote Similarity	NPD5507	Approved
0.6639	Remote Similarity	NPD6298	Discontinued
0.6639	Remote Similarity	NPD5506	Approved
0.6638	Remote Similarity	NPD4037	Approved
0.6638	Remote Similarity	NPD4039	Approved
0.6638	Remote Similarity	NPD4035	Approved
0.6638	Remote Similarity	NPD32	Approved
0.6638	Remote Similarity	NPD4122	Approved
0.6638	Remote Similarity	NPD4036	Approved
0.6638	Remote Similarity	NPD4034	Approved
0.6638	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4038	Approved
0.6638	Remote Similarity	NPD31	Approved
0.6638	Remote Similarity	NPD4033	Approved
0.6637	Remote Similarity	NPD6137	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