NPASS Compound

Structure

NPC473089 OpenBabel07101719132D 51 56 0 0 1 0 0 0 0 0999 V2000 0.6532 -1.0298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3800 -4.5345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0155 -2.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5127 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3146 1.8944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2223 3.4018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3980 -1.0705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2223 2.4202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0724 3.8926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6305 -1.6826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2517 -0.0998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9525 -1.5078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0724 1.9294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9226 3.4018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7168 -1.3239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3379 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0145 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6721 -0.8402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5758 -1.8341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5855 -0.0950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5157 0.4062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7376 -0.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3175 -1.1761 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0213 -3.6208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0448 -2.4469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9226 2.4202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5705 -0.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7961 -0.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3385 0.8551 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2747 -1.9395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9226 0.4569 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7155 -1.3868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9754 -0.2480 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8580 0.0279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7727 1.9294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6567 0.0054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3586 0.9138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4572 -0.7288 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7582 -0.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4537 0.1169 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0506 -3.4744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4327 -3.2144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6396 0.9849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6228 2.4202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5104 0.9761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1384 -0.6398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6334 -2.8533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6862 -1.5331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7727 0.9477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8892 -0.6067 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 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 37 1 0 0 0 0 5 37 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 26 2 0 0 0 0 14 26 1 0 0 0 0 15 27 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 40 2 0 0 0 0 19 23 1 0 0 0 0 19 30 1 0 0 0 0 21 28 2 0 0 0 0 21 40 1 0 0 0 0 22 38 1 0 0 0 0 22 46 1 0 0 0 0 23 39 1 6 0 0 0 24 41 2 0 0 0 0 24 47 1 0 0 0 0 25 42 2 0 0 0 0 25 48 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 28 34 1 0 0 0 0 29 20 1 6 0 0 0 29 31 1 0 0 0 0 29 37 1 0 0 0 0 30 32 1 0 0 0 0 30 47 1 6 0 0 0 31 33 1 0 0 0 0 31 49 1 6 0 0 0 32 38 1 6 0 0 0 32 48 1 0 0 0 0 33 38 1 6 0 0 0 33 50 1 0 0 0 0 34 43 2 0 0 0 0 34 46 1 0 0 0 0 35 44 2 0 0 0 0 35 49 1 0 0 0 0 36 45 2 0 0 0 0 36 50 1 0 0 0 0 37 51 1 0 0 0 0 38 39 1 1 0 0 0 39 20 1 6 0 0 0 39 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	699.27
Volume:	702.54
LogP:	4.948
LogD:	3.246
LogS:	-3.715
# Rotatable Bonds:	14
TPSA:	153.62
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	5.888
Fsp3:	0.436
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:	-5.365
MDCK Permeability:	3.0448192774201743e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	90.71863555908203%
Volume Distribution (VD):	2.63
Pgp-substrate:	6.994391441345215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.343
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.861
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.973
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.36

ADMET: Excretion

Clearance (CL):	6.575
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.877
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.559
Carcinogencity:	0.249
Eye Corrosion:	0.003
Eye Irritation:	0.107
Respiratory Toxicity:	0.174

Download Data

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

Natural Product: NPC473089

Natural Product ID:	NPC473089
*Common Name:**	XLDGWIQPEFDDDV-ZVLXBXPZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XLDGWIQPEFDDDV-ZVLXBXPZSA-N
Standard InCHI:	InChI=1S/C39H41NO11/c1-23-19-30(47-24(2)41)32(48-25(3)42)38(22-46-34(43)28-17-12-18-40-21-28)33(50-36(45)27-15-10-7-11-16-27)31(29-20-39(23,38)51-37(29,4)5)49-35(44)26-13-8-6-9-14-26/h6-18,21,23,29-33H,19-20,22H2,1-5H3/t23-,29+,30+,31-,32+,33-,38+,39+/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@@H](C)[C@]23[C@]([C@H]1OC(=O)C)(COC(=O)c1cccnc1)[C@H](OC(=O)c1ccccc1)[C@@H]([C@H](C2)C(O3)(C)C)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609597
PubChem CID:	n.a.
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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25272	Celastrus angulatus	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	77.8	%	PMID[506136]

☑ 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 NPC473089 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	392
0.1-0.2	1561
0.2-0.3	3481
0.3-0.4	10814
0.4-0.5	18400
0.5-0.6	6063
0.6-0.7	1712
0.7-0.8	90
0.8-0.85	56
0.85-0.9	33
0.9-0.95	69
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC212768
1.0	High Similarity	NPC6576
1.0	High Similarity	NPC75600
1.0	High Similarity	NPC473115
1.0	High Similarity	NPC158020
0.9845	High Similarity	NPC4421
0.9797	High Similarity	NPC127720
0.9797	High Similarity	NPC127026
0.9747	High Similarity	NPC471980
0.9646	High Similarity	NPC477903
0.9645	High Similarity	NPC84815
0.9645	High Similarity	NPC301368
0.9543	High Similarity	NPC6981
0.95	High Similarity	NPC477788
0.9495	High Similarity	NPC294579
0.9495	High Similarity	NPC144779
0.9461	High Similarity	NPC475596
0.9461	High Similarity	NPC316841
0.9461	High Similarity	NPC475303
0.9444	High Similarity	NPC471016
0.9415	High Similarity	NPC30456
0.9406	High Similarity	NPC477899
0.9406	High Similarity	NPC477900
0.9406	High Similarity	NPC328154
0.9397	High Similarity	NPC62367
0.9394	High Similarity	NPC470306
0.935	High Similarity	NPC216428
0.9347	High Similarity	NPC471014
0.9347	High Similarity	NPC475408
0.9343	High Similarity	NPC264674
0.9324	High Similarity	NPC475406
0.9314	High Similarity	NPC328186
0.9314	High Similarity	NPC477787
0.9314	High Similarity	NPC228377
0.9314	High Similarity	NPC475631
0.9314	High Similarity	NPC122968
0.9314	High Similarity	NPC211920
0.9314	High Similarity	NPC476110
0.9314	High Similarity	NPC87152
0.9314	High Similarity	NPC475600
0.931	High Similarity	NPC477902
0.9307	High Similarity	NPC235364
0.9296	High Similarity	NPC42678
0.9296	High Similarity	NPC477907
0.9296	High Similarity	NPC477909
0.9279	High Similarity	NPC38959
0.9279	High Similarity	NPC327904
0.9268	High Similarity	NPC470486
0.9268	High Similarity	NPC471190
0.9268	High Similarity	NPC475644
0.9268	High Similarity	NPC471977
0.9257	High Similarity	NPC477912
0.9231	High Similarity	NPC327769
0.922	High Similarity	NPC124029
0.9216	High Similarity	NPC26881
0.9208	High Similarity	NPC477901
0.9179	High Similarity	NPC473689
0.9179	High Similarity	NPC96801
0.9179	High Similarity	NPC292416
0.9179	High Similarity	NPC150698
0.9171	High Similarity	NPC473506
0.9167	High Similarity	NPC57797
0.9167	High Similarity	NPC76565
0.9167	High Similarity	NPC250807
0.9146	High Similarity	NPC472553
0.9135	High Similarity	NPC244839
0.9135	High Similarity	NPC320324
0.9135	High Similarity	NPC319880
0.913	High Similarity	NPC91125
0.9122	High Similarity	NPC475137
0.9122	High Similarity	NPC475498
0.9122	High Similarity	NPC473850
0.9091	High Similarity	NPC237702
0.9078	High Similarity	NPC148860
0.9064	High Similarity	NPC472555
0.9034	High Similarity	NPC475601
0.9034	High Similarity	NPC146824
0.9019	High Similarity	NPC475648
0.8995	High Similarity	NPC472550
0.8995	High Similarity	NPC304179
0.8995	High Similarity	NPC48042
0.8995	High Similarity	NPC477906
0.899	High Similarity	NPC475362
0.8966	High Similarity	NPC206343
0.8966	High Similarity	NPC477908
0.896	High Similarity	NPC319128
0.8932	High Similarity	NPC477911
0.8916	High Similarity	NPC477910
0.8879	High Similarity	NPC253482
0.8868	High Similarity	NPC170751
0.8867	High Similarity	NPC228331
0.8863	High Similarity	NPC469748
0.885	High Similarity	NPC63041
0.8779	High Similarity	NPC35208
0.8779	High Similarity	NPC475426
0.8768	High Similarity	NPC323551
0.8768	High Similarity	NPC280473
0.8725	High Similarity	NPC51008
0.8725	High Similarity	NPC41724
0.87	High Similarity	NPC289086
0.8685	High Similarity	NPC213143
0.8585	High Similarity	NPC14116
0.8585	High Similarity	NPC476467
0.8585	High Similarity	NPC285411
0.8545	High Similarity	NPC311196
0.8545	High Similarity	NPC134384
0.8454	Intermediate Similarity	NPC165837
0.8423	Intermediate Similarity	NPC475533
0.8387	Intermediate Similarity	NPC238278
0.8386	Intermediate Similarity	NPC475315
0.8386	Intermediate Similarity	NPC324619
0.8381	Intermediate Similarity	NPC187494
0.8378	Intermediate Similarity	NPC180668
0.8378	Intermediate Similarity	NPC148896
0.8378	Intermediate Similarity	NPC471013
0.8373	Intermediate Similarity	NPC62844
0.8373	Intermediate Similarity	NPC193361
0.8357	Intermediate Similarity	NPC470189
0.8357	Intermediate Similarity	NPC40919
0.8317	Intermediate Similarity	NPC470279
0.8311	Intermediate Similarity	NPC10904
0.8301	Intermediate Similarity	NPC470190
0.8294	Intermediate Similarity	NPC319556
0.8286	Intermediate Similarity	NPC30570
0.8261	Intermediate Similarity	NPC472752
0.8252	Intermediate Similarity	NPC475835
0.8246	Intermediate Similarity	NPC475301
0.8246	Intermediate Similarity	NPC162812
0.8246	Intermediate Similarity	NPC53255
0.8246	Intermediate Similarity	NPC85879
0.8246	Intermediate Similarity	NPC326930
0.8233	Intermediate Similarity	NPC233727
0.823	Intermediate Similarity	NPC292517
0.821	Intermediate Similarity	NPC13603
0.8202	Intermediate Similarity	NPC471015
0.82	Intermediate Similarity	NPC103230
0.8199	Intermediate Similarity	NPC207531
0.819	Intermediate Similarity	NPC328928
0.8103	Intermediate Similarity	NPC473833
0.8053	Intermediate Similarity	NPC476090
0.8034	Intermediate Similarity	NPC471978
0.8008	Intermediate Similarity	NPC471979
0.7928	Intermediate Similarity	NPC471004
0.7857	Intermediate Similarity	NPC309498
0.7682	Intermediate Similarity	NPC253314
0.7558	Intermediate Similarity	NPC111732
0.7524	Intermediate Similarity	NPC320748
0.7524	Intermediate Similarity	NPC324245
0.75	Intermediate Similarity	NPC328559
0.75	Intermediate Similarity	NPC32451
0.7454	Intermediate Similarity	NPC470280
0.7453	Intermediate Similarity	NPC79223
0.7393	Intermediate Similarity	NPC329024
0.7391	Intermediate Similarity	NPC44354
0.7382	Intermediate Similarity	NPC37473
0.7358	Intermediate Similarity	NPC107287
0.7327	Intermediate Similarity	NPC156044
0.7321	Intermediate Similarity	NPC140311
0.7309	Intermediate Similarity	NPC141385
0.7304	Intermediate Similarity	NPC233334
0.7299	Intermediate Similarity	NPC135950
0.7293	Intermediate Similarity	NPC24019
0.7288	Intermediate Similarity	NPC124313
0.7284	Intermediate Similarity	NPC108342
0.7277	Intermediate Similarity	NPC59033
0.7277	Intermediate Similarity	NPC317672
0.7264	Intermediate Similarity	NPC249614
0.7257	Intermediate Similarity	NPC106593
0.7256	Intermediate Similarity	NPC155792
0.7253	Intermediate Similarity	NPC182907
0.7253	Intermediate Similarity	NPC189903
0.7243	Intermediate Similarity	NPC123395
0.7243	Intermediate Similarity	NPC103361
0.7241	Intermediate Similarity	NPC90875
0.7235	Intermediate Similarity	NPC25442
0.7235	Intermediate Similarity	NPC12944
0.7228	Intermediate Similarity	NPC191310
0.7225	Intermediate Similarity	NPC327699
0.7225	Intermediate Similarity	NPC473667
0.722	Intermediate Similarity	NPC317010
0.722	Intermediate Similarity	NPC471997
0.7213	Intermediate Similarity	NPC191489
0.7203	Intermediate Similarity	NPC207283
0.7203	Intermediate Similarity	NPC84164
0.7198	Intermediate Similarity	NPC70155
0.7166	Intermediate Similarity	NPC315634
0.7166	Intermediate Similarity	NPC88923
0.7166	Intermediate Similarity	NPC100734
0.7163	Intermediate Similarity	NPC282103
0.7162	Intermediate Similarity	NPC318299
0.715	Intermediate Similarity	NPC112741
0.7149	Intermediate Similarity	NPC314834
0.7149	Intermediate Similarity	NPC166722
0.7149	Intermediate Similarity	NPC470020
0.7137	Intermediate Similarity	NPC183537
0.713	Intermediate Similarity	NPC236668
0.713	Intermediate Similarity	NPC317752
0.7124	Intermediate Similarity	NPC22481
0.7123	Intermediate Similarity	NPC471546
0.7113	Intermediate Similarity	NPC107123

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 NPC473089 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	590
0.2-0.3	653
0.3-0.4	1749
0.4-0.5	3239
0.5-0.6	2169
0.6-0.7	486
0.7-0.8	27
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
0.8238	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD8468	Phase 2
0.7725	Intermediate Similarity	NPD7396	Approved
0.7593	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD820	Phase 3
0.7511	Intermediate Similarity	NPD5891	Approved
0.7442	Intermediate Similarity	NPD7010	Phase 3
0.7364	Intermediate Similarity	NPD3795	Approved
0.7364	Intermediate Similarity	NPD3794	Approved
0.736	Intermediate Similarity	NPD6635	Approved
0.7324	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD7885	Phase 2
0.7265	Intermediate Similarity	NPD7886	Phase 2
0.7235	Intermediate Similarity	NPD3947	Discontinued
0.722	Intermediate Similarity	NPD3389	Approved
0.722	Intermediate Similarity	NPD3394	Approved
0.722	Intermediate Similarity	NPD3393	Approved
0.7215	Intermediate Similarity	NPD2509	Approved
0.7215	Intermediate Similarity	NPD2510	Approved
0.7213	Intermediate Similarity	NPD7708	Approved
0.7195	Intermediate Similarity	NPD4417	Approved
0.7166	Intermediate Similarity	NPD7803	Approved
0.7162	Intermediate Similarity	NPD7069	Discontinued
0.715	Intermediate Similarity	NPD9271	Approved
0.7143	Intermediate Similarity	NPD7234	Approved
0.7143	Intermediate Similarity	NPD7233	Approved
0.7137	Intermediate Similarity	NPD4301	Approved
0.7124	Intermediate Similarity	NPD6770	Approved
0.7117	Intermediate Similarity	NPD5475	Discontinued
0.7116	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD4506	Discontinued
0.7102	Intermediate Similarity	NPD7955	Approved
0.7102	Intermediate Similarity	NPD7956	Approved
0.7064	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1483	Discontinued
0.7027	Intermediate Similarity	NPD6529	Discontinued
0.7018	Intermediate Similarity	NPD3280	Approved
0.7	Intermediate Similarity	NPD6987	Phase 1
0.7	Intermediate Similarity	NPD2831	Approved
0.6991	Remote Similarity	NPD8485	Approved
0.6974	Remote Similarity	NPD7404	Approved
0.6957	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7187	Phase 2
0.6895	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8326	Phase 3
0.6886	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8325	Phase 3
0.6884	Remote Similarity	NPD4376	Phase 3
0.6881	Remote Similarity	NPD53	Approved
0.6881	Remote Similarity	NPD7777	Approved
0.6881	Remote Similarity	NPD7778	Approved
0.687	Remote Similarity	NPD8479	Phase 2
0.6869	Remote Similarity	NPD8063	Discontinued
0.6863	Remote Similarity	NPD6446	Discontinued
0.6856	Remote Similarity	NPD7878	Phase 2
0.6854	Remote Similarity	NPD6791	Phase 2
0.6851	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4889	Approved
0.6839	Remote Similarity	NPD107	Approved
0.6833	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.683	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.683	Remote Similarity	NPD7191	Phase 2
0.6816	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6790	Phase 1
0.6805	Remote Similarity	NPD7417	Discontinued
0.6798	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6226	Phase 3
0.6787	Remote Similarity	NPD8091	Phase 3
0.6784	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7395	Discontinued
0.6766	Remote Similarity	NPD6026	Approved
0.6765	Remote Similarity	NPD5088	Discontinued
0.6759	Remote Similarity	NPD2336	Approved
0.6751	Remote Similarity	NPD7688	Phase 1
0.6748	Remote Similarity	NPD5482	Discontinued
0.6742	Remote Similarity	NPD6479	Discontinued
0.6741	Remote Similarity	NPD7957	Phase 1
0.6741	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4989	Phase 2
0.6739	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3922	Approved
0.6728	Remote Similarity	NPD3924	Approved
0.6728	Remote Similarity	NPD3921	Approved
0.6728	Remote Similarity	NPD3923	Approved
0.6726	Remote Similarity	NPD6176	Phase 1
0.6723	Remote Similarity	NPD8289	Discontinued
0.6713	Remote Similarity	NPD6281	Approved
0.6712	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3006	Discontinued
0.6701	Remote Similarity	NPD9075	Approved
0.6701	Remote Similarity	NPD9074	Approved
0.6698	Remote Similarity	NPD4948	Discontinued
0.6697	Remote Similarity	NPD6361	Phase 2
0.6696	Remote Similarity	NPD5901	Discontinued
0.6696	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7467	Discontinued
0.6681	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7470	Discontinued
0.6667	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7707	Approved
0.665	Remote Similarity	NPD2581	Approved
0.665	Remote Similarity	NPD2582	Approved
0.664	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8412	Phase 1
0.6638	Remote Similarity	NPD3815	Phase 1
0.6638	Remote Similarity	NPD5866	Approved
0.6638	Remote Similarity	NPD3816	Phase 1
0.6637	Remote Similarity	NPD3371	Approved
0.6637	Remote Similarity	NPD7562	Approved
0.6636	Remote Similarity	NPD2307	Discontinued
0.6636	Remote Similarity	NPD8361	Approved
0.6636	Remote Similarity	NPD8435	Approved
0.6636	Remote Similarity	NPD8360	Approved
0.6635	Remote Similarity	NPD6641	Approved
0.6635	Remote Similarity	NPD6642	Approved
0.6633	Remote Similarity	NPD1270	Approved
0.6624	Remote Similarity	NPD7994	Phase 2
0.6623	Remote Similarity	NPD5490	Discontinued
0.662	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8356	Approved
0.6593	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6219	Discontinued
0.6591	Remote Similarity	NPD4427	Phase 2
0.6585	Remote Similarity	NPD2511	Approved
0.6582	Remote Similarity	NPD7426	Phase 1
0.6581	Remote Similarity	NPD1996	Discontinued
0.6569	Remote Similarity	NPD4952	Phase 3
0.6569	Remote Similarity	NPD5022	Discontinued
0.6567	Remote Similarity	NPD4429	Discontinued
0.6557	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD8021	Approved
0.6544	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD8020	Approved
0.6543	Remote Similarity	NPD5805	Approved
0.6542	Remote Similarity	NPD6962	Phase 2
0.6542	Remote Similarity	NPD3386	Phase 2
0.6538	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6228	Discontinued
0.6532	Remote Similarity	NPD5003	Discontinued
0.6527	Remote Similarity	NPD8467	Approved
0.6527	Remote Similarity	NPD8466	Approved
0.6527	Remote Similarity	NPD8465	Approved
0.6525	Remote Similarity	NPD6995	Phase 1
0.6518	Remote Similarity	NPD4501	Approved
0.6518	Remote Similarity	NPD7967	Discontinued
0.6518	Remote Similarity	NPD4500	Approved
0.6518	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD6242	Discontinued
0.6504	Remote Similarity	NPD5513	Phase 2
0.6504	Remote Similarity	NPD6716	Phase 1
0.6498	Remote Similarity	NPD5450	Discontinued
0.6492	Remote Similarity	NPD8100	Phase 3
0.6491	Remote Similarity	NPD5429	Discontinued
0.6488	Remote Similarity	NPD4373	Phase 2
0.6486	Remote Similarity	NPD8364	Approved
0.6486	Remote Similarity	NPD8363	Approved
0.6485	Remote Similarity	NPD8430	Approved
0.6485	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4499	Approved
0.6483	Remote Similarity	NPD6298	Discontinued
0.648	Remote Similarity	NPD2896	Discontinued
0.6479	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8409	Suspended
0.6473	Remote Similarity	NPD7673	Phase 3
0.6471	Remote Similarity	NPD4529	Approved
0.6471	Remote Similarity	NPD4526	Approved
0.6471	Remote Similarity	NPD4528	Approved
0.6471	Remote Similarity	NPD3925	Approved
0.6468	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6276	Discontinued
0.6463	Remote Similarity	NPD7576	Discontinued
0.6461	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6963	Approved
0.6461	Remote Similarity	NPD6964	Approved
0.6457	Remote Similarity	NPD7169	Suspended
0.6456	Remote Similarity	NPD1630	Approved
0.6453	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7921	Approved
0.645	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7001	Phase 3
0.6444	Remote Similarity	NPD4601	Approved
0.6444	Remote Similarity	NPD5640	Discontinued
0.6444	Remote Similarity	NPD4600	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