NPASS Compound

Structure

NPC141405 OpenBabel07101718322D 52 56 0 0 1 0 0 0 0 0999 V2000 0.7606 3.5292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0963 3.0137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2124 3.0430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9712 3.4980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1324 5.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3370 2.7085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7439 1.6015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2575 4.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1042 1.0459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3781 2.0325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3781 2.0325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1773 -0.5327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4880 -0.1644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7425 4.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3502 2.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2948 1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5120 -0.1644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9893 4.4978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5893 1.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9635 2.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4413 0.2655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8289 -0.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7604 4.4184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8152 0.6197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.2201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9712 3.4980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3502 2.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2948 1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7883 2.4215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0681 1.3691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8152 0.6197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2278 4.2021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4413 0.2655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8642 4.9821 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.5697 1.7643 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.9621 1.9466 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.0464 -0.5306 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.7038 -0.6249 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.6378 3.8905 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 2.0797 5.3660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5773 -0.0277 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.2201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4532 3.1684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3879 0.4216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7434 5.0590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0464 -0.5306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4187 6.1164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5190 0.3086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2124 3.0430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1042 1.0459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 15 1 0 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 3 16 1 0 0 0 0 4 40 1 0 0 0 0 5 15 2 0 0 0 0 5 19 1 0 0 0 0 6 16 2 0 0 0 0 6 20 1 0 0 0 0 7 17 2 0 0 0 0 7 21 1 0 0 0 0 8 15 1 0 0 0 0 8 24 1 0 0 0 0 9 17 1 0 0 0 0 9 25 1 0 0 0 0 10 16 1 0 0 0 0 10 29 2 0 0 0 0 11 17 1 0 0 0 0 11 28 2 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 18 1 0 0 0 0 13 23 2 0 0 0 0 14 26 1 0 0 0 0 14 41 1 0 0 0 0 18 26 1 0 0 0 0 19 27 2 0 0 0 0 19 35 1 0 0 0 0 20 31 2 0 0 0 0 20 36 1 0 0 0 0 21 30 2 0 0 0 0 21 37 1 0 0 0 0 22 32 2 0 0 0 0 22 38 1 0 0 0 0 23 32 1 0 0 0 0 23 39 1 0 0 0 0 24 33 1 0 0 0 0 24 42 2 0 0 0 0 25 34 1 0 0 0 0 25 43 2 0 0 0 0 26 44 1 6 0 0 0 27 51 1 0 0 0 0 28 30 1 0 0 0 0 28 51 1 0 0 0 0 29 31 1 0 0 0 0 29 52 1 0 0 0 0 30 45 1 0 0 0 0 31 46 1 0 0 0 0 32 52 1 0 0 0 0 33 40 2 3 0 0 0 33 47 1 0 0 0 0 34 41 2 3 0 0 0 34 48 1 0 0 0 0 42 49 1 0 0 0 0 43 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1029.77
Volume:	731.172
LogP:	6.274
LogD:	2.704
LogS:	-4.074
# Rotatable Bonds:	0
TPSA:	202.53
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	8
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.068
Synthetic Accessibility Score:	6.449
Fsp3:	0.176
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.031
MDCK Permeability:	1.3500953173206653e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.943
20% Bioavailability (F20%):	0.2
30% Bioavailability (F30%):	0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	104.63539123535156%
Volume Distribution (VD):	0.329
Pgp-substrate:	0.848742663860321%

ADMET: Metabolism

CYP1A2-inhibitor:	0.238
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.978
CYP2C9-substrate:	0.748
CYP2D6-inhibitor:	0.731
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.562
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	-0.298
Half-life (T1/2):	0.124

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.384
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.82
Carcinogencity:	0.115
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.046

Download Data

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

Natural Product: NPC141405

Natural Product ID:	NPC141405
*Common Name:**	Bastadin 12
IUPAC Name:	n.a.
Synonyms:	Bastadin 12
Standard InCHIKey:	YUJCERKJBSZPJE-BMMWFESESA-N
Standard InCHI:	InChI=1S/C34H27Br5N4O9/c35-19-5-15-1-2-27(19)51-28-11-17(7-21(37)30(28)45)9-25(43-50)34(48)41-14-26(44)18-12-22(38)32(23(39)13-18)52-29-10-16(6-20(36)31(29)46)3-4-40-33(47)24(8-15)42-49/h1-2,5-7,10-13,26,44-46,49-50H,3-4,8-9,14H2,(H,40,47)(H,41,48)/b42-24+,43-25+/t26-/m1/s1
SMILES:	c1cc2c(cc1C/C(=NO)/C(=NCCc1cc(c(c(c1)Oc1c(cc(cc1Br)[C@@H](CN=C(/C(=N/O)/Cc1cc(c(c(c1)O2)O)Br)O)O)Br)O)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500333
PubChem CID:	44575628
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
NPO6672	Ianthella quadrangulata	Species	Ianthellidae	Eukaryota	n.a.	Australian	n.a.	PMID[18298075]
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]
NPO6672	Ianthella quadrangulata	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	7
MIC	2
Others	2

Activity Type	# Activity
Cell Line	8
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	Activity	=	27.6	%	PMID[469531]
NPT168	Cell Line	P388	Mus musculus	ED50	=	9.1	ug ml-1	PMID[469532]
NPT377	Cell Line	OVCAR-3	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[469532]
NPT399	Cell Line	SF-295	Homo sapiens	ED50	=	2.4	ug ml-1	PMID[469532]
NPT376	Cell Line	A498	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[469532]
NPT397	Cell Line	NCI-H460	Homo sapiens	ED50	=	2.3	ug ml-1	PMID[469532]
NPT575	Cell Line	KM-20L2	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[469532]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	ED50	=	2.2	ug ml-1	PMID[469532]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	50.0	ug	PMID[469532]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug	PMID[469532]
NPT2	Others	Unspecified		Inhibition	=	80.0	%	PMID[469533]

☑ 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 NPC141405 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	413
0.1-0.2	2293
0.2-0.3	12071
0.3-0.4	7298
0.4-0.5	9302
0.5-0.6	9367
0.6-0.7	1875
0.7-0.8	48
0.8-0.85	3
0.85-0.9	4
0.9-0.95	13
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473409
1.0	High Similarity	NPC82741
0.988	High Similarity	NPC49172
0.9821	High Similarity	NPC471591
0.9709	High Similarity	NPC469721
0.9704	High Similarity	NPC475658
0.9704	High Similarity	NPC473892
0.9521	High Similarity	NPC298981
0.9521	High Similarity	NPC473462
0.9521	High Similarity	NPC207819
0.9521	High Similarity	NPC110454
0.9521	High Similarity	NPC126128
0.9486	High Similarity	NPC469731
0.9461	High Similarity	NPC226001
0.9461	High Similarity	NPC469979
0.9401	High Similarity	NPC225130
0.9353	High Similarity	NPC74618
0.9353	High Similarity	NPC301941
0.9353	High Similarity	NPC214188
0.9235	High Similarity	NPC290534
0.9138	High Similarity	NPC144823
0.907	High Similarity	NPC475396
0.8764	High Similarity	NPC470951
0.875	High Similarity	NPC156055
0.8693	High Similarity	NPC475283
0.8693	High Similarity	NPC152205
0.8629	High Similarity	NPC475615
0.7849	Intermediate Similarity	NPC258222
0.7809	Intermediate Similarity	NPC179250
0.7809	Intermediate Similarity	NPC50380
0.7798	Intermediate Similarity	NPC474128
0.7791	Intermediate Similarity	NPC470935
0.7791	Intermediate Similarity	NPC471032
0.7733	Intermediate Similarity	NPC277857
0.7733	Intermediate Similarity	NPC115144
0.768	Intermediate Similarity	NPC90984
0.767	Intermediate Similarity	NPC156311
0.76	Intermediate Similarity	NPC475432
0.7544	Intermediate Similarity	NPC222039
0.7544	Intermediate Similarity	NPC100478
0.7528	Intermediate Similarity	NPC107602
0.7515	Intermediate Similarity	NPC312770
0.7515	Intermediate Similarity	NPC204848
0.7515	Intermediate Similarity	NPC41473
0.7515	Intermediate Similarity	NPC14600
0.7515	Intermediate Similarity	NPC160607
0.7514	Intermediate Similarity	NPC5462
0.7471	Intermediate Similarity	NPC299583
0.7443	Intermediate Similarity	NPC109968
0.743	Intermediate Similarity	NPC473738
0.7401	Intermediate Similarity	NPC47672
0.7365	Intermediate Similarity	NPC473724
0.7365	Intermediate Similarity	NPC475735
0.736	Intermediate Similarity	NPC127402
0.7305	Intermediate Similarity	NPC474091
0.7299	Intermediate Similarity	NPC78530
0.7299	Intermediate Similarity	NPC135349
0.7278	Intermediate Similarity	NPC233926
0.7262	Intermediate Similarity	NPC114102
0.7219	Intermediate Similarity	NPC214869
0.7209	Intermediate Similarity	NPC474673
0.7209	Intermediate Similarity	NPC213471
0.7207	Intermediate Similarity	NPC7398
0.7151	Intermediate Similarity	NPC182119
0.7143	Intermediate Similarity	NPC470372
0.7114	Intermediate Similarity	NPC471337
0.7101	Intermediate Similarity	NPC35961
0.7101	Intermediate Similarity	NPC52029
0.7101	Intermediate Similarity	NPC195749
0.7095	Intermediate Similarity	NPC76412
0.7094	Intermediate Similarity	NPC254581
0.7088	Intermediate Similarity	NPC56635
0.7071	Intermediate Similarity	NPC474678
0.7071	Intermediate Similarity	NPC471338
0.7069	Intermediate Similarity	NPC474390
0.7069	Intermediate Similarity	NPC296898
0.7065	Intermediate Similarity	NPC123848
0.7052	Intermediate Similarity	NPC309667
0.7041	Intermediate Similarity	NPC155838
0.7035	Intermediate Similarity	NPC303993
0.7035	Intermediate Similarity	NPC475843
0.7033	Intermediate Similarity	NPC275027
0.7031	Intermediate Similarity	NPC32064
0.7029	Intermediate Similarity	NPC260842
0.7026	Intermediate Similarity	NPC276120
0.702	Intermediate Similarity	NPC41122
0.702	Intermediate Similarity	NPC318805
0.7017	Intermediate Similarity	NPC152947
0.7015	Intermediate Similarity	NPC50548
0.7005	Intermediate Similarity	NPC29531
0.6989	Remote Similarity	NPC38980
0.6989	Remote Similarity	NPC262189
0.6983	Remote Similarity	NPC274960
0.6983	Remote Similarity	NPC143120
0.6983	Remote Similarity	NPC473909
0.6982	Remote Similarity	NPC186898
0.6982	Remote Similarity	NPC251571
0.6982	Remote Similarity	NPC153990
0.6965	Remote Similarity	NPC234318
0.6965	Remote Similarity	NPC144314
0.6964	Remote Similarity	NPC194519
0.695	Remote Similarity	NPC85381
0.6944	Remote Similarity	NPC88896
0.6941	Remote Similarity	NPC72529
0.6936	Remote Similarity	NPC71888
0.6936	Remote Similarity	NPC120114
0.6932	Remote Similarity	NPC477838
0.6932	Remote Similarity	NPC477837
0.6927	Remote Similarity	NPC28440
0.6927	Remote Similarity	NPC171932
0.6923	Remote Similarity	NPC178284
0.6923	Remote Similarity	NPC58607
0.6923	Remote Similarity	NPC301713
0.6923	Remote Similarity	NPC304630
0.6923	Remote Similarity	NPC17837
0.6923	Remote Similarity	NPC191037
0.6919	Remote Similarity	NPC93882
0.6919	Remote Similarity	NPC130595
0.6915	Remote Similarity	NPC149962
0.6914	Remote Similarity	NPC77861
0.6901	Remote Similarity	NPC86030
0.6901	Remote Similarity	NPC5851
0.69	Remote Similarity	NPC227953
0.6897	Remote Similarity	NPC245386
0.6893	Remote Similarity	NPC55793
0.6893	Remote Similarity	NPC22317
0.6889	Remote Similarity	NPC245974
0.6888	Remote Similarity	NPC138083
0.6882	Remote Similarity	NPC183181
0.6882	Remote Similarity	NPC41706
0.6882	Remote Similarity	NPC111247
0.6882	Remote Similarity	NPC163332
0.6882	Remote Similarity	NPC319625
0.6882	Remote Similarity	NPC292056
0.6882	Remote Similarity	NPC147821
0.6882	Remote Similarity	NPC118787
0.6879	Remote Similarity	NPC6854
0.6879	Remote Similarity	NPC285078
0.6879	Remote Similarity	NPC131128
0.6879	Remote Similarity	NPC313737
0.6879	Remote Similarity	NPC474134
0.6875	Remote Similarity	NPC271942
0.6868	Remote Similarity	NPC304048
0.6868	Remote Similarity	NPC226153
0.6866	Remote Similarity	NPC202866
0.6857	Remote Similarity	NPC93783
0.6853	Remote Similarity	NPC259071
0.6853	Remote Similarity	NPC77435
0.6842	Remote Similarity	NPC198741
0.6842	Remote Similarity	NPC256012
0.6842	Remote Similarity	NPC317272
0.6842	Remote Similarity	NPC240841
0.6842	Remote Similarity	NPC268503
0.6842	Remote Similarity	NPC250846
0.6842	Remote Similarity	NPC42549
0.6839	Remote Similarity	NPC218530
0.6836	Remote Similarity	NPC22517
0.6831	Remote Similarity	NPC470826
0.6831	Remote Similarity	NPC475250
0.6831	Remote Similarity	NPC473266
0.6831	Remote Similarity	NPC470098
0.6824	Remote Similarity	NPC134431
0.6824	Remote Similarity	NPC156854
0.6823	Remote Similarity	NPC164608
0.6816	Remote Similarity	NPC63628
0.6816	Remote Similarity	NPC470472
0.6816	Remote Similarity	NPC178466
0.6814	Remote Similarity	NPC123859
0.6805	Remote Similarity	NPC95733
0.6805	Remote Similarity	NPC62101
0.6805	Remote Similarity	NPC109822
0.6805	Remote Similarity	NPC114901
0.6805	Remote Similarity	NPC48990
0.6805	Remote Similarity	NPC293701
0.6805	Remote Similarity	NPC94276
0.6802	Remote Similarity	NPC99280
0.6802	Remote Similarity	NPC30779
0.68	Remote Similarity	NPC66840
0.68	Remote Similarity	NPC256307
0.68	Remote Similarity	NPC170694
0.6798	Remote Similarity	NPC291101
0.6798	Remote Similarity	NPC266197
0.6794	Remote Similarity	NPC470746
0.6794	Remote Similarity	NPC471336
0.6793	Remote Similarity	NPC477612
0.6786	Remote Similarity	NPC71090
0.6782	Remote Similarity	NPC7903
0.6782	Remote Similarity	NPC35932
0.6782	Remote Similarity	NPC16208
0.6782	Remote Similarity	NPC160991
0.6782	Remote Similarity	NPC184447
0.678	Remote Similarity	NPC156356
0.678	Remote Similarity	NPC242728
0.6778	Remote Similarity	NPC247298
0.6776	Remote Similarity	NPC281549
0.6776	Remote Similarity	NPC139699
0.6776	Remote Similarity	NPC114659
0.6768	Remote Similarity	NPC121571
0.6768	Remote Similarity	NPC8093
0.6765	Remote Similarity	NPC29477

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 NPC141405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	862
0.2-0.3	1634
0.3-0.4	2847
0.4-0.5	2274
0.5-0.6	1153
0.6-0.7	158
0.7-0.8	1
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
0.7135	Intermediate Similarity	NPD4123	Phase 3
0.7104	Intermediate Similarity	NPD5772	Approved
0.7104	Intermediate Similarity	NPD5773	Approved
0.7006	Intermediate Similarity	NPD6331	Phase 2
0.7006	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8095	Phase 1
0.694	Remote Similarity	NPD4678	Approved
0.694	Remote Similarity	NPD4675	Approved
0.6919	Remote Similarity	NPD2674	Phase 3
0.6906	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4005	Discontinued
0.6854	Remote Similarity	NPD3060	Approved
0.6842	Remote Similarity	NPD4010	Discontinued
0.6828	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD52	Approved
0.6813	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7526	Approved
0.6798	Remote Similarity	NPD7153	Discontinued
0.678	Remote Similarity	NPD2161	Phase 2
0.6776	Remote Similarity	NPD2122	Discontinued
0.6763	Remote Similarity	NPD3145	Approved
0.6763	Remote Similarity	NPD3144	Approved
0.676	Remote Similarity	NPD4162	Approved
0.6717	Remote Similarity	NPD8053	Approved
0.6717	Remote Similarity	NPD8054	Approved
0.6686	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5241	Discontinued
0.6684	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4236	Phase 3
0.6667	Remote Similarity	NPD4237	Approved
0.6649	Remote Similarity	NPD2978	Approved
0.6649	Remote Similarity	NPD2977	Approved
0.6648	Remote Similarity	NPD1375	Discontinued
0.6632	Remote Similarity	NPD8070	Approved
0.6629	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1558	Phase 1
0.6576	Remote Similarity	NPD4739	Approved
0.6559	Remote Similarity	NPD3687	Approved
0.6559	Remote Similarity	NPD3686	Approved
0.6556	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.655	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6072	Discontinued
0.6543	Remote Similarity	NPD3778	Approved
0.6535	Remote Similarity	NPD7906	Approved
0.6532	Remote Similarity	NPD6584	Phase 3
0.6514	Remote Similarity	NPD3027	Phase 3
0.6513	Remote Similarity	NPD2489	Approved
0.6513	Remote Similarity	NPD27	Approved
0.6497	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1613	Approved
0.6495	Remote Similarity	NPD3051	Approved
0.6492	Remote Similarity	NPD7773	Phase 2
0.6486	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4663	Approved
0.6482	Remote Similarity	NPD7039	Approved
0.6482	Remote Similarity	NPD7038	Approved
0.6477	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD2970	Approved
0.6462	Remote Similarity	NPD2969	Approved
0.6458	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7833	Phase 2
0.6458	Remote Similarity	NPD7831	Phase 2
0.6441	Remote Similarity	NPD7477	Discontinued
0.6438	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3054	Approved
0.6425	Remote Similarity	NPD5314	Approved
0.6425	Remote Similarity	NPD3052	Approved
0.6418	Remote Similarity	NPD4577	Approved
0.6418	Remote Similarity	NPD4578	Approved
0.6414	Remote Similarity	NPD8156	Discontinued
0.6404	Remote Similarity	NPD3059	Approved
0.6404	Remote Similarity	NPD3062	Approved
0.6404	Remote Similarity	NPD3061	Approved
0.6398	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3985	Discontinued
0.6398	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3536	Discontinued
0.6387	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8099	Discontinued
0.6364	Remote Similarity	NPD8251	Approved
0.6364	Remote Similarity	NPD8252	Approved
0.6358	Remote Similarity	NPD6583	Phase 3
0.6358	Remote Similarity	NPD6582	Phase 2
0.6354	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7007	Discovery
0.6344	Remote Similarity	NPD7213	Phase 3
0.6344	Remote Similarity	NPD7212	Phase 2
0.6344	Remote Similarity	NPD1774	Approved
0.6339	Remote Similarity	NPD7037	Approved
0.6335	Remote Similarity	NPD5722	Discontinued
0.6327	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD2677	Approved
0.631	Remote Similarity	NPD7447	Phase 1
0.6302	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6687	Approved
0.6294	Remote Similarity	NPD6688	Approved
0.6293	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5718	Phase 2
0.6289	Remote Similarity	NPD4055	Discovery
0.6287	Remote Similarity	NPD2802	Phase 3
0.6277	Remote Similarity	NPD2183	Approved
0.6277	Remote Similarity	NPD2184	Approved
0.6271	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD2560	Approved
0.6269	Remote Similarity	NPD2563	Approved
0.6257	Remote Similarity	NPD839	Approved
0.6257	Remote Similarity	NPD840	Approved
0.6257	Remote Similarity	NPD1423	Approved
0.6256	Remote Similarity	NPD7313	Approved
0.6256	Remote Similarity	NPD7311	Approved
0.6256	Remote Similarity	NPD7310	Approved
0.6256	Remote Similarity	NPD7312	Approved
0.6244	Remote Similarity	NPD6071	Discontinued
0.6237	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD2922	Phase 1
0.6225	Remote Similarity	NPD7309	Approved
0.6224	Remote Similarity	NPD4666	Phase 3
0.6221	Remote Similarity	NPD9384	Approved
0.6221	Remote Similarity	NPD9381	Approved
0.6216	Remote Similarity	NPD5177	Phase 3
0.6215	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD4083	Discontinued
0.6207	Remote Similarity	NPD2231	Phase 2
0.6207	Remote Similarity	NPD2235	Phase 2
0.6205	Remote Similarity	NPD5604	Discontinued
0.6201	Remote Similarity	NPD5109	Approved
0.6201	Remote Similarity	NPD5110	Phase 2
0.6201	Remote Similarity	NPD5111	Phase 2
0.62	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6063	Approved
0.6184	Remote Similarity	NPD2845	Phase 2
0.6184	Remote Similarity	NPD2843	Phase 2
0.6178	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD5709	Phase 3
0.6171	Remote Similarity	NPD1669	Approved
0.6171	Remote Similarity	NPD9622	Approved
0.6166	Remote Similarity	NPD4433	Discontinued
0.6162	Remote Similarity	NPD7608	Discontinued
0.6158	Remote Similarity	NPD6030	Approved
0.6158	Remote Similarity	NPD7451	Discontinued
0.6158	Remote Similarity	NPD6031	Approved
0.6154	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.615	Remote Similarity	NPD3692	Discontinued
0.6146	Remote Similarity	NPD3296	Phase 1
0.6145	Remote Similarity	NPD3179	Approved
0.6145	Remote Similarity	NPD3180	Approved
0.6138	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD7020	Approved
0.6138	Remote Similarity	NPD7019	Approved
0.6134	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD821	Approved
0.6129	Remote Similarity	NPD5062	Approved
0.6129	Remote Similarity	NPD2460	Phase 3
0.6129	Remote Similarity	NPD5061	Approved
0.6129	Remote Similarity	NPD2459	Approved
0.6129	Remote Similarity	NPD2458	Approved
0.6127	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4210	Discontinued
0.6124	Remote Similarity	NPD4993	Discontinued
0.612	Remote Similarity	NPD6896	Approved
0.612	Remote Similarity	NPD6895	Approved
0.6117	Remote Similarity	NPD7124	Phase 2
0.6114	Remote Similarity	NPD7438	Suspended
0.6114	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD4772	Phase 2
0.6114	Remote Similarity	NPD4773	Phase 2
0.6111	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD601	Approved
0.6111	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD597	Approved
0.6111	Remote Similarity	NPD598	Approved
0.6108	Remote Similarity	NPD3656	Approved
0.6106	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6166	Phase 2
0.61	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7125	Discontinued
0.6094	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD3455	Phase 2
0.6089	Remote Similarity	NPD4908	Phase 1
0.6089	Remote Similarity	NPD42	Phase 2
0.6089	Remote Similarity	NPD6042	Phase 2
0.6085	Remote Similarity	NPD4357	Discontinued
0.6085	Remote Similarity	NPD6087	Phase 1
0.608	Remote Similarity	NPD3685	Discontinued
0.6077	Remote Similarity	NPD1130	Approved
0.6077	Remote Similarity	NPD3530	Approved
0.6077	Remote Similarity	NPD3532	Approved
0.6077	Remote Similarity	NPD2488	Approved
0.6077	Remote Similarity	NPD2490	Approved
0.6077	Remote Similarity	NPD3531	Approved
0.6077	Remote Similarity	NPD1136	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