NPASS Compound

Structure

NPC473892 OpenBabel07101718222D 56 60 0 0 1 0 0 0 0 0999 V2000 -1.4627 0.0932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5931 -5.0663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1425 -4.8237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1421 0.7309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8690 1.2186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4432 1.2393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9079 -1.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8355 -2.0285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0078 -1.3762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3474 -4.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4398 -4.6853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2150 -2.5094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4534 -3.7801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3946 -1.6502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8561 0.0932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0495 -2.7391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7632 0.3560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3559 0.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8561 -0.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9159 -3.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2812 -2.2134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3128 1.0749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6110 0.3866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7744 -4.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5937 -4.6240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1594 -0.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1390 -3.3343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9346 -3.4663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3842 -1.0757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8004 0.8150 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.0084 1.1361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0078 0.5829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2899 -3.2027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2237 -3.8607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1594 0.0932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3865 -3.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3372 -3.0564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2506 -0.5170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1311 -0.4435 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.4226 -5.9517 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.0440 -5.4348 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.3111 -1.3762 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.9388 -3.8999 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.6422 -2.5696 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5552 -4.2243 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3560 -0.9523 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2654 1.6356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1062 -3.6632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1731 -0.1875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3111 0.5829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2966 -4.6564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5219 -4.0658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7349 -0.0489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5381 0.9139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7210 -3.5824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 51 1 0 0 0 0 2 52 1 0 0 0 0 3 53 1 0 0 0 0 4 54 1 0 0 0 0 5 6 2 0 0 0 0 5 22 1 0 0 0 0 6 31 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 44 1 0 0 0 0 9 19 2 0 0 0 0 9 26 1 0 0 0 0 10 20 2 0 0 0 0 10 24 1 0 0 0 0 11 20 1 0 0 0 0 11 25 2 0 0 0 0 12 21 2 0 0 0 0 12 27 1 0 0 0 0 13 20 1 0 0 0 0 13 28 1 0 0 0 0 14 21 1 0 0 0 0 14 29 1 0 0 0 0 15 19 1 0 0 0 0 15 32 2 0 0 0 0 16 21 1 0 0 0 0 16 33 2 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 30 1 0 0 0 0 18 45 1 0 0 0 0 22 30 1 0 0 0 0 23 31 2 0 0 0 0 23 39 1 0 0 0 0 24 34 2 0 0 0 0 24 40 1 0 0 0 0 25 34 1 0 0 0 0 25 41 1 0 0 0 0 26 35 2 0 0 0 0 26 42 1 0 0 0 0 27 36 2 0 0 0 0 27 43 1 0 0 0 0 28 37 1 0 0 0 0 28 46 2 0 0 0 0 29 38 1 0 0 0 0 29 47 2 0 0 0 0 30 48 1 0 0 0 0 31 55 1 0 0 0 0 32 35 1 0 0 0 0 32 55 1 0 0 0 0 33 36 1 0 0 0 0 33 56 1 0 0 0 0 34 56 1 0 0 0 0 35 51 1 0 0 0 0 36 52 1 0 0 0 0 37 44 2 3 0 0 0 37 49 1 0 0 0 0 38 45 2 3 0 0 0 38 50 1 0 0 0 0 46 53 1 0 0 0 0 47 54 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1085.83
Volume:	800.355
LogP:	7.392
LogD:	3.941
LogS:	-5.373
# Rotatable Bonds:	4
TPSA:	158.53
# H-Bond Aceptor:	13
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.17
Synthetic Accessibility Score:	6.482
Fsp3:	0.263
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:	-6.021
MDCK Permeability:	1.2838359907618724e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.895
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.342

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	102.17212677001953%
Volume Distribution (VD):	0.348
Pgp-substrate:	4.633089065551758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.08
CYP1A2-substrate:	0.698
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.975
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.919
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	-0.744
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.496
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.067
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC473892

Natural Product ID:	NPC473892
*Common Name:**	Tetramethylbastadin 8
IUPAC Name:	n.a.
Synonyms:	Tetramethylbastadin 8
Standard InCHIKey:	IVJUBYZXZVYIOY-PTPKFGMMSA-N
Standard InCHI:	InChI=1S/C38H35Br5N4O9/c1-51-35-26(42)9-19-7-8-44-37(49)28(46-53-3)13-20-10-24(40)34(25(41)11-20)56-33-16-21(12-27(43)36(33)52-2)14-29(47-54-4)38(50)45-18-30(48)22-5-6-31(23(39)17-22)55-32(35)15-19/h5-6,9-12,15-17,30,48H,7-8,13-14,18H2,1-4H3,(H,44,49)(H,45,50)/b46-28-,47-29+
SMILES:	COC1=C2C=C(CCNC(=O)C(=NOC)CC3=CC(=C(C(=C3)Br)OC4=C(C(=CC(=C4)CC(=NOC)C(=O)NCC(C5=CC(=C(O2)C=C5)Br)O)Br)OC)Br)C=C1Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454509
PubChem CID:	44567113
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[2089117]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23249297]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Bismarck archipelago	n.a.	PMID[7623047]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[8904842]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988595]
NPO16920	Ianthella basta	Species	Ianthellidae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	ED50	=	5.0	ug ml-1	PMID[574305]

☑ 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 NPC473892 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	364
0.1-0.2	2067
0.2-0.3	11363
0.3-0.4	7951
0.4-0.5	9305
0.5-0.6	9923
0.6-0.7	1645
0.7-0.8	49
0.8-0.85	5
0.85-0.9	5
0.9-0.95	13
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475658
0.9704	High Similarity	NPC141405
0.9704	High Similarity	NPC82741
0.9704	High Similarity	NPC473409
0.9586	High Similarity	NPC49172
0.9529	High Similarity	NPC471591
0.9425	High Similarity	NPC469721
0.9349	High Similarity	NPC475396
0.9231	High Similarity	NPC473462
0.9231	High Similarity	NPC298981
0.9231	High Similarity	NPC110454
0.9231	High Similarity	NPC207819
0.9231	High Similarity	NPC126128
0.9209	High Similarity	NPC469731
0.9172	High Similarity	NPC469979
0.9172	High Similarity	NPC226001
0.9112	High Similarity	NPC225130
0.907	High Similarity	NPC74618
0.907	High Similarity	NPC214188
0.907	High Similarity	NPC301941
0.8953	High Similarity	NPC290534
0.8864	High Similarity	NPC144823
0.8678	High Similarity	NPC475615
0.8603	High Similarity	NPC470951
0.8531	High Similarity	NPC152205
0.8531	High Similarity	NPC475283
0.8495	Intermediate Similarity	NPC156055
0.8	Intermediate Similarity	NPC258222
0.7853	Intermediate Similarity	NPC179250
0.7853	Intermediate Similarity	NPC50380
0.7844	Intermediate Similarity	NPC474128
0.7816	Intermediate Similarity	NPC156311
0.763	Intermediate Similarity	NPC471032
0.763	Intermediate Similarity	NPC470935
0.7624	Intermediate Similarity	NPC90984
0.7586	Intermediate Similarity	NPC109968
0.7572	Intermediate Similarity	NPC115144
0.7572	Intermediate Similarity	NPC277857
0.7544	Intermediate Similarity	NPC135349
0.7543	Intermediate Similarity	NPC47672
0.7543	Intermediate Similarity	NPC475432
0.7514	Intermediate Similarity	NPC233926
0.7485	Intermediate Similarity	NPC222039
0.7485	Intermediate Similarity	NPC100478
0.7472	Intermediate Similarity	NPC107602
0.7457	Intermediate Similarity	NPC5462
0.7442	Intermediate Similarity	NPC78530
0.7374	Intermediate Similarity	NPC473738
0.7353	Intermediate Similarity	NPC160607
0.7353	Intermediate Similarity	NPC312770
0.7353	Intermediate Similarity	NPC14600
0.7353	Intermediate Similarity	NPC204848
0.7353	Intermediate Similarity	NPC41473
0.733	Intermediate Similarity	NPC76412
0.731	Intermediate Similarity	NPC299583
0.7305	Intermediate Similarity	NPC475735
0.7303	Intermediate Similarity	NPC127402
0.7288	Intermediate Similarity	NPC182119
0.7251	Intermediate Similarity	NPC474673
0.7246	Intermediate Similarity	NPC474091
0.7236	Intermediate Similarity	NPC471337
0.7214	Intermediate Similarity	NPC254581
0.7202	Intermediate Similarity	NPC473724
0.7168	Intermediate Similarity	NPC260842
0.7151	Intermediate Similarity	NPC213471
0.7127	Intermediate Similarity	NPC56635
0.7119	Intermediate Similarity	NPC245974
0.7107	Intermediate Similarity	NPC474678
0.7107	Intermediate Similarity	NPC471338
0.7104	Intermediate Similarity	NPC123848
0.7101	Intermediate Similarity	NPC114102
0.7086	Intermediate Similarity	NPC470372
0.7085	Intermediate Similarity	NPC144314
0.7071	Intermediate Similarity	NPC475843
0.7066	Intermediate Similarity	NPC301713
0.7059	Intermediate Similarity	NPC214869
0.7056	Intermediate Similarity	NPC7398
0.705	Intermediate Similarity	NPC50548
0.7045	Intermediate Similarity	NPC470472
0.7037	Intermediate Similarity	NPC164608
0.7035	Intermediate Similarity	NPC149962
0.702	Intermediate Similarity	NPC227953
0.7006	Intermediate Similarity	NPC247298
0.6994	Remote Similarity	NPC309667
0.6994	Remote Similarity	NPC93783
0.6979	Remote Similarity	NPC32064
0.6978	Remote Similarity	NPC275027
0.6977	Remote Similarity	NPC303993
0.6974	Remote Similarity	NPC276120
0.697	Remote Similarity	NPC41122
0.697	Remote Similarity	NPC318805
0.6954	Remote Similarity	NPC29531
0.6946	Remote Similarity	NPC95733
0.6946	Remote Similarity	NPC62101
0.6941	Remote Similarity	NPC52029
0.6941	Remote Similarity	NPC35961
0.6941	Remote Similarity	NPC195749
0.6931	Remote Similarity	NPC123859
0.6927	Remote Similarity	NPC143120
0.6927	Remote Similarity	NPC274960
0.6927	Remote Similarity	NPC473909
0.6915	Remote Similarity	NPC234318
0.6914	Remote Similarity	NPC296898
0.6906	Remote Similarity	NPC139699
0.6906	Remote Similarity	NPC114659
0.6905	Remote Similarity	NPC29477
0.69	Remote Similarity	NPC202866
0.6897	Remote Similarity	NPC242728
0.6889	Remote Similarity	NPC93610
0.6889	Remote Similarity	NPC241846
0.6888	Remote Similarity	NPC259071
0.6888	Remote Similarity	NPC77435
0.6882	Remote Similarity	NPC155838
0.6879	Remote Similarity	NPC120114
0.6879	Remote Similarity	NPC71888
0.6872	Remote Similarity	NPC313414
0.6872	Remote Similarity	NPC195538
0.6857	Remote Similarity	NPC77861
0.6854	Remote Similarity	NPC178466
0.6854	Remote Similarity	NPC63628
0.6851	Remote Similarity	NPC99183
0.6845	Remote Similarity	NPC109822
0.6845	Remote Similarity	NPC94276
0.6845	Remote Similarity	NPC38980
0.6837	Remote Similarity	NPC476202
0.6837	Remote Similarity	NPC138083
0.6827	Remote Similarity	NPC471336
0.6827	Remote Similarity	NPC470746
0.6826	Remote Similarity	NPC71090
0.6825	Remote Similarity	NPC470936
0.6824	Remote Similarity	NPC153990
0.6824	Remote Similarity	NPC186898
0.6824	Remote Similarity	NPC251571
0.6821	Remote Similarity	NPC6854
0.6821	Remote Similarity	NPC313737
0.6821	Remote Similarity	NPC285078
0.6818	Remote Similarity	NPC474390
0.6816	Remote Similarity	NPC471563
0.6816	Remote Similarity	NPC85381
0.6813	Remote Similarity	NPC226153
0.6813	Remote Similarity	NPC304048
0.6805	Remote Similarity	NPC194519
0.6802	Remote Similarity	NPC8093
0.6802	Remote Similarity	NPC121571
0.68	Remote Similarity	NPC475132
0.68	Remote Similarity	NPC474587
0.6789	Remote Similarity	NPC250846
0.6789	Remote Similarity	NPC42549
0.6789	Remote Similarity	NPC268503
0.6789	Remote Similarity	NPC256012
0.6789	Remote Similarity	NPC317272
0.6789	Remote Similarity	NPC240841
0.6786	Remote Similarity	NPC211218
0.678	Remote Similarity	NPC477838
0.678	Remote Similarity	NPC212850
0.678	Remote Similarity	NPC189724
0.678	Remote Similarity	NPC83289
0.678	Remote Similarity	NPC477837
0.6776	Remote Similarity	NPC475250
0.6776	Remote Similarity	NPC473266
0.6776	Remote Similarity	NPC469711
0.6776	Remote Similarity	NPC470826
0.6776	Remote Similarity	NPC152947
0.6776	Remote Similarity	NPC470098
0.6768	Remote Similarity	NPC249996
0.6768	Remote Similarity	NPC174607
0.6765	Remote Similarity	NPC17837
0.6765	Remote Similarity	NPC178284
0.6765	Remote Similarity	NPC191037
0.6765	Remote Similarity	NPC304630
0.6765	Remote Similarity	NPC58607
0.6763	Remote Similarity	NPC469613
0.6763	Remote Similarity	NPC30043
0.6763	Remote Similarity	NPC469625
0.6763	Remote Similarity	NPC93882
0.6763	Remote Similarity	NPC130595
0.6761	Remote Similarity	NPC254610
0.6761	Remote Similarity	NPC475293
0.6761	Remote Similarity	NPC470470
0.6757	Remote Similarity	NPC197741
0.6757	Remote Similarity	NPC18249
0.6757	Remote Similarity	NPC140915
0.6757	Remote Similarity	NPC10221
0.6757	Remote Similarity	NPC187028
0.6757	Remote Similarity	NPC305700
0.6751	Remote Similarity	NPC30779
0.6746	Remote Similarity	NPC114901
0.6746	Remote Similarity	NPC48990
0.6746	Remote Similarity	NPC293701
0.6744	Remote Similarity	NPC99280
0.6744	Remote Similarity	NPC86030
0.6744	Remote Similarity	NPC5851
0.6742	Remote Similarity	NPC291101
0.6742	Remote Similarity	NPC22317
0.6742	Remote Similarity	NPC262189
0.6742	Remote Similarity	NPC266197
0.674	Remote Similarity	NPC71629
0.674	Remote Similarity	NPC296085
0.6739	Remote Similarity	NPC471235
0.6739	Remote Similarity	NPC235033

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 NPC473892 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	836
0.2-0.3	1542
0.3-0.4	2773
0.4-0.5	2383
0.5-0.6	1225
0.6-0.7	184
0.7-0.8	4
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
0.7333	Intermediate Similarity	NPD5772	Approved
0.7333	Intermediate Similarity	NPD5773	Approved
0.7273	Intermediate Similarity	NPD4123	Phase 3
0.7241	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD8095	Phase 1
0.7143	Intermediate Similarity	NPD6331	Phase 2
0.7072	Intermediate Similarity	NPD4675	Approved
0.7072	Intermediate Similarity	NPD4678	Approved
0.7049	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD52	Approved
0.7039	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7526	Approved
0.7029	Intermediate Similarity	NPD7153	Discontinued
0.7017	Intermediate Similarity	NPD4005	Discontinued
0.6914	Remote Similarity	NPD2161	Phase 2
0.6902	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3060	Approved
0.6816	Remote Similarity	NPD5241	Discontinued
0.6813	Remote Similarity	NPD2122	Discontinued
0.6798	Remote Similarity	NPD4236	Phase 3
0.6798	Remote Similarity	NPD4162	Approved
0.6798	Remote Similarity	NPD4237	Approved
0.6784	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1375	Discontinued
0.6763	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2674	Phase 3
0.6755	Remote Similarity	NPD8070	Approved
0.6724	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4739	Approved
0.6702	Remote Similarity	NPD4010	Discontinued
0.6686	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3687	Approved
0.6685	Remote Similarity	NPD3686	Approved
0.6667	Remote Similarity	NPD8054	Approved
0.6667	Remote Similarity	NPD8053	Approved
0.6667	Remote Similarity	NPD7477	Discontinued
0.6667	Remote Similarity	NPD6072	Discontinued
0.6615	Remote Similarity	NPD8156	Discontinued
0.6614	Remote Similarity	NPD7773	Phase 2
0.6609	Remote Similarity	NPD3145	Approved
0.6609	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3144	Approved
0.6599	Remote Similarity	NPD7038	Approved
0.6599	Remote Similarity	NPD7039	Approved
0.6597	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7831	Phase 2
0.6579	Remote Similarity	NPD7833	Phase 2
0.6579	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6584	Phase 3
0.6564	Remote Similarity	NPD8251	Approved
0.6564	Remote Similarity	NPD8099	Discontinued
0.6564	Remote Similarity	NPD8252	Approved
0.6556	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5722	Discontinued
0.6528	Remote Similarity	NPD3051	Approved
0.6522	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5718	Phase 2
0.6508	Remote Similarity	NPD2977	Approved
0.6508	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD2978	Approved
0.6495	Remote Similarity	NPD2970	Approved
0.6495	Remote Similarity	NPD6687	Approved
0.6495	Remote Similarity	NPD6688	Approved
0.6495	Remote Similarity	NPD2969	Approved
0.6485	Remote Similarity	NPD7906	Approved
0.6485	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD3052	Approved
0.6461	Remote Similarity	NPD3054	Approved
0.6443	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6071	Discontinued
0.6441	Remote Similarity	NPD1558	Phase 1
0.6432	Remote Similarity	NPD7447	Phase 1
0.6421	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4055	Discovery
0.6402	Remote Similarity	NPD3778	Approved
0.6398	Remote Similarity	NPD2183	Approved
0.6398	Remote Similarity	NPD2184	Approved
0.6396	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6582	Phase 2
0.6395	Remote Similarity	NPD6583	Phase 3
0.6387	Remote Similarity	NPD2563	Approved
0.6387	Remote Similarity	NPD2560	Approved
0.6384	Remote Similarity	NPD840	Approved
0.6384	Remote Similarity	NPD839	Approved
0.6382	Remote Similarity	NPD7007	Discovery
0.6378	Remote Similarity	NPD2489	Approved
0.6378	Remote Similarity	NPD1774	Approved
0.6378	Remote Similarity	NPD7213	Phase 3
0.6378	Remote Similarity	NPD7212	Phase 2
0.6378	Remote Similarity	NPD27	Approved
0.6364	Remote Similarity	NPD3027	Phase 3
0.6359	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7608	Discontinued
0.6359	Remote Similarity	NPD2677	Approved
0.6358	Remote Similarity	NPD2922	Phase 1
0.6344	Remote Similarity	NPD3536	Discontinued
0.6339	Remote Similarity	NPD5177	Phase 3
0.6333	Remote Similarity	NPD6896	Approved
0.6333	Remote Similarity	NPD6895	Approved
0.6328	Remote Similarity	NPD5110	Phase 2
0.6328	Remote Similarity	NPD5109	Approved
0.6328	Remote Similarity	NPD5111	Phase 2
0.6327	Remote Similarity	NPD4083	Discontinued
0.6324	Remote Similarity	NPD7124	Phase 2
0.6319	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD2802	Phase 3
0.6318	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4772	Phase 2
0.6316	Remote Similarity	NPD7438	Suspended
0.6316	Remote Similarity	NPD4773	Phase 2
0.6302	Remote Similarity	NPD6063	Approved
0.6301	Remote Similarity	NPD1669	Approved
0.6298	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD1423	Approved
0.629	Remote Similarity	NPD6087	Phase 1
0.6286	Remote Similarity	NPD7451	Discontinued
0.6284	Remote Similarity	NPD7037	Approved
0.628	Remote Similarity	NPD7125	Discontinued
0.6278	Remote Similarity	NPD5314	Approved
0.6278	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6031	Approved
0.6277	Remote Similarity	NPD6030	Approved
0.6275	Remote Similarity	NPD4663	Approved
0.627	Remote Similarity	NPD3692	Discontinued
0.6265	Remote Similarity	NPD821	Approved
0.6257	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD3985	Discontinued
0.6257	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1613	Approved
0.625	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2459	Approved
0.625	Remote Similarity	NPD2458	Approved
0.625	Remote Similarity	NPD2460	Phase 3
0.625	Remote Similarity	NPD4993	Discontinued
0.6243	Remote Similarity	NPD4210	Discontinued
0.6243	Remote Similarity	NPD2231	Phase 2
0.6243	Remote Similarity	NPD2235	Phase 2
0.6237	Remote Similarity	NPD6667	Approved
0.6237	Remote Similarity	NPD8031	Discontinued
0.6237	Remote Similarity	NPD5604	Discontinued
0.6237	Remote Similarity	NPD6666	Approved
0.6236	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD2843	Phase 2
0.6214	Remote Similarity	NPD2845	Phase 2
0.6211	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7313	Approved
0.6207	Remote Similarity	NPD7312	Approved
0.6207	Remote Similarity	NPD3685	Discontinued
0.6207	Remote Similarity	NPD7310	Approved
0.6207	Remote Similarity	NPD4578	Approved
0.6207	Remote Similarity	NPD4577	Approved
0.6207	Remote Similarity	NPD7311	Approved
0.6205	Remote Similarity	NPD5709	Phase 3
0.6203	Remote Similarity	NPD4357	Discontinued
0.6201	Remote Similarity	NPD3532	Approved
0.6201	Remote Similarity	NPD3530	Approved
0.6201	Remote Similarity	NPD3531	Approved
0.62	Remote Similarity	NPD42	Phase 2
0.62	Remote Similarity	NPD6042	Phase 2
0.6199	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4433	Discontinued
0.6197	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7131	Phase 3
0.6188	Remote Similarity	NPD2157	Approved
0.6186	Remote Similarity	NPD6788	Approved
0.6186	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD2219	Phase 1
0.6181	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3179	Approved
0.618	Remote Similarity	NPD3180	Approved
0.6178	Remote Similarity	NPD3296	Phase 1
0.6176	Remote Similarity	NPD7309	Approved
0.6173	Remote Similarity	NPD6746	Phase 2
0.6173	Remote Similarity	NPD4666	Phase 3
0.6171	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7019	Approved
0.617	Remote Similarity	NPD7020	Approved
0.6167	Remote Similarity	NPD3062	Approved
0.6167	Remote Similarity	NPD2238	Phase 2
0.6167	Remote Similarity	NPD3059	Approved
0.6167	Remote Similarity	NPD3061	Approved
0.6165	Remote Similarity	NPD6841	Approved
0.6165	Remote Similarity	NPD6843	Phase 3
0.6165	Remote Similarity	NPD6842	Approved
0.6158	Remote Similarity	NPD7549	Discontinued
0.6158	Remote Similarity	NPD1712	Approved
0.6158	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6815	Approved
0.6146	Remote Similarity	NPD6386	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