NPASS Compound

Structure

NPC49172 OpenBabel07101719152D 51 55 0 0 1 0 0 0 0 0999 V2000 0.8722 4.0473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2936 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1104 3.4561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7996 0.3045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6840 3.4897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4074 4.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1518 5.7493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9737 3.1061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9999 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4421 5.1939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2662 1.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8740 2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5804 2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7182 0.6834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5597 -0.1886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8515 5.1939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8420 2.9206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4848 1.7481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7339 -0.1886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1345 5.1581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4654 1.1330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2629 2.2491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2518 2.2945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0189 5.0670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9348 0.7106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1468 -0.2524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1138 4.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2284 0.7106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7784 1.7481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5484 2.9206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6653 1.5700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0509 2.7769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5549 4.8190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5060 0.3045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1378 5.7134 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.4447 2.2796 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.3873 2.0233 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.3969 2.2324 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.0250 4.4616 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 2.3850 6.1537 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8089 -0.0318 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1468 -1.3992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0320 0.4835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8134 3.6335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1461 5.8016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2001 -0.6085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6270 7.0142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8888 0.3539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3904 3.4897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5598 1.1994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 16 1 0 0 0 0 2 4 2 0 0 0 0 2 19 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 6 1 0 0 0 0 5 17 1 0 0 0 0 6 39 1 0 0 0 0 7 16 2 0 0 0 0 7 20 1 0 0 0 0 8 17 2 0 0 0 0 8 22 1 0 0 0 0 9 18 2 0 0 0 0 9 23 1 0 0 0 0 10 16 1 0 0 0 0 10 24 1 0 0 0 0 11 18 1 0 0 0 0 11 25 1 0 0 0 0 12 17 1 0 0 0 0 12 29 2 0 0 0 0 13 18 1 0 0 0 0 13 30 2 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 26 1 0 0 0 0 15 40 1 0 0 0 0 19 26 1 0 0 0 0 20 27 2 0 0 0 0 20 35 1 0 0 0 0 21 28 2 0 0 0 0 21 36 1 0 0 0 0 22 31 2 0 0 0 0 22 37 1 0 0 0 0 23 32 2 0 0 0 0 23 38 1 0 0 0 0 24 33 1 0 0 0 0 24 41 2 0 0 0 0 25 34 1 0 0 0 0 25 42 2 0 0 0 0 26 43 1 6 0 0 0 27 50 1 0 0 0 0 28 51 1 0 0 0 0 29 31 1 0 0 0 0 29 51 1 0 0 0 0 30 32 1 0 0 0 0 30 50 1 0 0 0 0 31 44 1 0 0 0 0 32 45 1 0 0 0 0 33 39 2 3 0 0 0 33 46 1 0 0 0 0 34 40 2 3 0 0 0 34 47 1 0 0 0 0 41 48 1 0 0 0 0 42 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	951.86
Volume:	711.888
LogP:	5.768
LogD:	2.831
LogS:	-4.081
# Rotatable Bonds:	0
TPSA:	202.53
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	8
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.072
Synthetic Accessibility Score:	6.377
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:	-6.014
MDCK Permeability:	1.42910330396262e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.896
20% Bioavailability (F20%):	0.265
30% Bioavailability (F30%):	0.106

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	102.92757415771484%
Volume Distribution (VD):	0.344
Pgp-substrate:	0.5048073530197144%

ADMET: Metabolism

CYP1A2-inhibitor:	0.334
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.979
CYP2C9-substrate:	0.843
CYP2D6-inhibitor:	0.807
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.69
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	-0.008
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.239
Drug-inuced Liver Injury (DILI):	0.544
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.785
Carcinogencity:	0.151
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC49172

Natural Product ID:	NPC49172
*Common Name:**	Bastadin 10
IUPAC Name:	n.a.
Synonyms:	Bastadin 10
Standard InCHIKey:	YBDUMXZBKBTNGS-JWAODPOQSA-N
Standard InCHI:	InChI=1S/C34H28Br4N4O9/c35-20-7-16-1-3-27(20)50-30-13-18(9-23(38)32(30)45)11-25(42-49)34(47)40-15-26(43)19-2-4-28(21(36)14-19)51-29-12-17(8-22(37)31(29)44)5-6-39-33(46)24(10-16)41-48/h1-4,7-9,12-14,26,43-45,48-49H,5-6,10-11,15H2,(H,39,46)(H,40,47)/b41-24+,42-25+/t26-/m1/s1
SMILES:	O/N=C/1Cc2ccc(c(c2)Br)Oc2cc(C/C(=NO)/C(=NC[C@H](c3ccc(Oc4cc(CCN=C1O)cc(Br)c4O)c(Br)c3)O)O)cc(c2O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503192
PubChem CID:	11491539
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	7
MIC	2

Activity Type	# Activity
Cell Line	7
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	10.0	ug ml-1	PMID[479663]
NPT377	Cell Line	OVCAR-3	Homo sapiens	ED50	=	2.9	ug ml-1	PMID[479663]
NPT399	Cell Line	SF-295	Homo sapiens	ED50	=	3.2	ug ml-1	PMID[479663]
NPT376	Cell Line	A498	Homo sapiens	ED50	=	4.5	ug ml-1	PMID[479663]
NPT397	Cell Line	NCI-H460	Homo sapiens	ED50	=	3.4	ug ml-1	PMID[479663]
NPT575	Cell Line	KM-20L2	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[479663]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	ED50	=	3.7	ug ml-1	PMID[479663]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	6.25	ug	PMID[479663]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.56	ug	PMID[479663]

☑ 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 NPC49172 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	397
0.1-0.2	2222
0.2-0.3	11675
0.3-0.4	7589
0.4-0.5	8941
0.5-0.6	9636
0.6-0.7	2152
0.7-0.8	56
0.8-0.85	1
0.85-0.9	5
0.9-0.95	15
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC82741
0.988	High Similarity	NPC141405
0.988	High Similarity	NPC473409
0.9702	High Similarity	NPC471591
0.9593	High Similarity	NPC469721
0.9586	High Similarity	NPC475658
0.9586	High Similarity	NPC473892
0.9515	High Similarity	NPC225130
0.9401	High Similarity	NPC207819
0.9401	High Similarity	NPC473462
0.9401	High Similarity	NPC298981
0.9401	High Similarity	NPC126128
0.9401	High Similarity	NPC110454
0.9371	High Similarity	NPC469731
0.9345	High Similarity	NPC290534
0.9341	High Similarity	NPC469979
0.9341	High Similarity	NPC226001
0.9235	High Similarity	NPC214188
0.9235	High Similarity	NPC301941
0.9235	High Similarity	NPC74618
0.9023	High Similarity	NPC144823
0.8953	High Similarity	NPC475396
0.8864	High Similarity	NPC470951
0.8793	High Similarity	NPC152205
0.8793	High Similarity	NPC475283
0.8728	High Similarity	NPC475615
0.8641	High Similarity	NPC156055
0.7898	Intermediate Similarity	NPC50380
0.7898	Intermediate Similarity	NPC179250
0.7892	Intermediate Similarity	NPC474128
0.7882	Intermediate Similarity	NPC470935
0.7882	Intermediate Similarity	NPC471032
0.7824	Intermediate Similarity	NPC277857
0.7824	Intermediate Similarity	NPC115144
0.7765	Intermediate Similarity	NPC90984
0.7733	Intermediate Similarity	NPC258222
0.7688	Intermediate Similarity	NPC475432
0.7633	Intermediate Similarity	NPC100478
0.7633	Intermediate Similarity	NPC222039
0.7614	Intermediate Similarity	NPC107602
0.7605	Intermediate Similarity	NPC14600
0.7605	Intermediate Similarity	NPC160607
0.7605	Intermediate Similarity	NPC204848
0.7605	Intermediate Similarity	NPC41473
0.7605	Intermediate Similarity	NPC312770
0.7602	Intermediate Similarity	NPC5462
0.756	Intermediate Similarity	NPC299583
0.7557	Intermediate Similarity	NPC156311
0.7514	Intermediate Similarity	NPC473738
0.7455	Intermediate Similarity	NPC473724
0.7443	Intermediate Similarity	NPC127402
0.7394	Intermediate Similarity	NPC474091
0.7349	Intermediate Similarity	NPC114102
0.733	Intermediate Similarity	NPC109968
0.7305	Intermediate Similarity	NPC214869
0.7288	Intermediate Similarity	NPC47672
0.7288	Intermediate Similarity	NPC7398
0.7246	Intermediate Similarity	NPC475735
0.7232	Intermediate Similarity	NPC182119
0.7225	Intermediate Similarity	NPC470372
0.7186	Intermediate Similarity	NPC195749
0.7186	Intermediate Similarity	NPC35961
0.7186	Intermediate Similarity	NPC52029
0.7184	Intermediate Similarity	NPC78530
0.7184	Intermediate Similarity	NPC135349
0.7167	Intermediate Similarity	NPC56635
0.7167	Intermediate Similarity	NPC233926
0.7164	Intermediate Similarity	NPC254581
0.7151	Intermediate Similarity	NPC474390
0.7151	Intermediate Similarity	NPC296898
0.7143	Intermediate Similarity	NPC123848
0.7126	Intermediate Similarity	NPC155838
0.7118	Intermediate Similarity	NPC303993
0.7111	Intermediate Similarity	NPC275027
0.711	Intermediate Similarity	NPC260842
0.7105	Intermediate Similarity	NPC32064
0.7098	Intermediate Similarity	NPC276120
0.7095	Intermediate Similarity	NPC152947
0.7093	Intermediate Similarity	NPC474673
0.7093	Intermediate Similarity	NPC213471
0.7092	Intermediate Similarity	NPC318805
0.7092	Intermediate Similarity	NPC41122
0.7085	Intermediate Similarity	NPC50548
0.7077	Intermediate Similarity	NPC29531
0.7069	Intermediate Similarity	NPC262189
0.7066	Intermediate Similarity	NPC186898
0.7066	Intermediate Similarity	NPC153990
0.7066	Intermediate Similarity	NPC251571
0.7065	Intermediate Similarity	NPC38980
0.7062	Intermediate Similarity	NPC473909
0.7062	Intermediate Similarity	NPC274960
0.7062	Intermediate Similarity	NPC143120
0.7048	Intermediate Similarity	NPC194519
0.7035	Intermediate Similarity	NPC234318
0.7035	Intermediate Similarity	NPC144314
0.7024	Intermediate Similarity	NPC72529
0.7022	Intermediate Similarity	NPC88896
0.702	Intermediate Similarity	NPC85381
0.7018	Intermediate Similarity	NPC71888
0.7018	Intermediate Similarity	NPC120114
0.7015	Intermediate Similarity	NPC471337
0.7011	Intermediate Similarity	NPC477837
0.7011	Intermediate Similarity	NPC477838
0.7006	Intermediate Similarity	NPC191037
0.7006	Intermediate Similarity	NPC304630
0.7006	Intermediate Similarity	NPC301713
0.7006	Intermediate Similarity	NPC171932
0.7006	Intermediate Similarity	NPC58607
0.7006	Intermediate Similarity	NPC17837
0.7006	Intermediate Similarity	NPC178284
0.7006	Intermediate Similarity	NPC28440
0.7	Intermediate Similarity	NPC93882
0.7	Intermediate Similarity	NPC130595
0.6994	Remote Similarity	NPC77861
0.6985	Remote Similarity	NPC149962
0.6983	Remote Similarity	NPC76412
0.6982	Remote Similarity	NPC5851
0.6982	Remote Similarity	NPC86030
0.6977	Remote Similarity	NPC245386
0.6971	Remote Similarity	NPC22317
0.6971	Remote Similarity	NPC55793
0.697	Remote Similarity	NPC471338
0.697	Remote Similarity	NPC474678
0.6966	Remote Similarity	NPC245974
0.6964	Remote Similarity	NPC292056
0.6964	Remote Similarity	NPC111247
0.6964	Remote Similarity	NPC163332
0.6964	Remote Similarity	NPC41706
0.6964	Remote Similarity	NPC319625
0.6964	Remote Similarity	NPC118787
0.6964	Remote Similarity	NPC147821
0.6964	Remote Similarity	NPC183181
0.6959	Remote Similarity	NPC138083
0.6959	Remote Similarity	NPC131128
0.6959	Remote Similarity	NPC285078
0.6959	Remote Similarity	NPC474134
0.6959	Remote Similarity	NPC6854
0.6959	Remote Similarity	NPC313737
0.6944	Remote Similarity	NPC304048
0.6944	Remote Similarity	NPC226153
0.6936	Remote Similarity	NPC93783
0.6936	Remote Similarity	NPC309667
0.6935	Remote Similarity	NPC475843
0.6919	Remote Similarity	NPC218530
0.6915	Remote Similarity	NPC240841
0.6915	Remote Similarity	NPC198741
0.6915	Remote Similarity	NPC42549
0.6915	Remote Similarity	NPC317272
0.6915	Remote Similarity	NPC256012
0.6915	Remote Similarity	NPC250846
0.6915	Remote Similarity	NPC268503
0.6914	Remote Similarity	NPC22517
0.6906	Remote Similarity	NPC470826
0.6906	Remote Similarity	NPC470098
0.6906	Remote Similarity	NPC473266
0.6906	Remote Similarity	NPC475250
0.6905	Remote Similarity	NPC134431
0.6905	Remote Similarity	NPC156854
0.6895	Remote Similarity	NPC164608
0.6893	Remote Similarity	NPC178466
0.6893	Remote Similarity	NPC63628
0.6886	Remote Similarity	NPC94276
0.6886	Remote Similarity	NPC293701
0.6886	Remote Similarity	NPC109822
0.6886	Remote Similarity	NPC95733
0.6886	Remote Similarity	NPC62101
0.6886	Remote Similarity	NPC48990
0.6886	Remote Similarity	NPC114901
0.6881	Remote Similarity	NPC123859
0.6879	Remote Similarity	NPC256307
0.6879	Remote Similarity	NPC170694
0.6879	Remote Similarity	NPC66840
0.6875	Remote Similarity	NPC266197
0.6875	Remote Similarity	NPC291101
0.6872	Remote Similarity	NPC30779
0.6868	Remote Similarity	NPC477612
0.6867	Remote Similarity	NPC71090
0.686	Remote Similarity	NPC184447
0.686	Remote Similarity	NPC16208
0.686	Remote Similarity	NPC160991
0.686	Remote Similarity	NPC7903
0.686	Remote Similarity	NPC35932
0.6857	Remote Similarity	NPC156356
0.6854	Remote Similarity	NPC247298
0.6851	Remote Similarity	NPC139699
0.6851	Remote Similarity	NPC114659
0.6851	Remote Similarity	NPC281549
0.6847	Remote Similarity	NPC242728
0.6845	Remote Similarity	NPC29477
0.6842	Remote Similarity	NPC326599
0.6842	Remote Similarity	NPC329595
0.6842	Remote Similarity	NPC472338
0.6842	Remote Similarity	NPC255550
0.6842	Remote Similarity	NPC308885
0.6839	Remote Similarity	NPC474587
0.6839	Remote Similarity	NPC475132
0.6836	Remote Similarity	NPC89341
0.6836	Remote Similarity	NPC178054
0.6833	Remote Similarity	NPC241846
0.6833	Remote Similarity	NPC93610

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 NPC49172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	859
0.2-0.3	1587
0.3-0.4	2804
0.4-0.5	2308
0.5-0.6	1190
0.6-0.7	186
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
0.7216	Intermediate Similarity	NPD4123	Phase 3
0.7182	Intermediate Similarity	NPD5773	Approved
0.7182	Intermediate Similarity	NPD5772	Approved
0.7086	Intermediate Similarity	NPD6331	Phase 2
0.7086	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD8095	Phase 1
0.7017	Intermediate Similarity	NPD4675	Approved
0.7017	Intermediate Similarity	NPD4678	Approved
0.7	Intermediate Similarity	NPD2674	Phase 3
0.6983	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4005	Discontinued
0.6932	Remote Similarity	NPD3060	Approved
0.6915	Remote Similarity	NPD4010	Discontinued
0.6902	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7526	Approved
0.6889	Remote Similarity	NPD52	Approved
0.6875	Remote Similarity	NPD7153	Discontinued
0.6857	Remote Similarity	NPD2161	Phase 2
0.6851	Remote Similarity	NPD2122	Discontinued
0.6842	Remote Similarity	NPD3145	Approved
0.6842	Remote Similarity	NPD3144	Approved
0.6836	Remote Similarity	NPD4162	Approved
0.6786	Remote Similarity	NPD8054	Approved
0.6786	Remote Similarity	NPD8053	Approved
0.6763	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5241	Discontinued
0.6757	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4237	Approved
0.6742	Remote Similarity	NPD4236	Phase 3
0.6723	Remote Similarity	NPD1375	Discontinued
0.672	Remote Similarity	NPD2978	Approved
0.672	Remote Similarity	NPD2977	Approved
0.6705	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD8070	Approved
0.6667	Remote Similarity	NPD1558	Phase 1
0.6648	Remote Similarity	NPD4739	Approved
0.663	Remote Similarity	NPD3687	Approved
0.663	Remote Similarity	NPD3686	Approved
0.6629	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6072	Discontinued
0.6613	Remote Similarity	NPD3778	Approved
0.6608	Remote Similarity	NPD6584	Phase 3
0.66	Remote Similarity	NPD7906	Approved
0.659	Remote Similarity	NPD3027	Phase 3
0.658	Remote Similarity	NPD27	Approved
0.658	Remote Similarity	NPD2489	Approved
0.6571	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1613	Approved
0.6562	Remote Similarity	NPD3051	Approved
0.6561	Remote Similarity	NPD7773	Phase 2
0.6557	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.655	Remote Similarity	NPD4663	Approved
0.6548	Remote Similarity	NPD7039	Approved
0.6548	Remote Similarity	NPD7038	Approved
0.6545	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2969	Approved
0.6528	Remote Similarity	NPD2970	Approved
0.6526	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7831	Phase 2
0.6526	Remote Similarity	NPD7833	Phase 2
0.6514	Remote Similarity	NPD7477	Discontinued
0.65	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3054	Approved
0.6497	Remote Similarity	NPD3052	Approved
0.6497	Remote Similarity	NPD5314	Approved
0.6494	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD4578	Approved
0.6482	Remote Similarity	NPD4577	Approved
0.648	Remote Similarity	NPD8156	Discontinued
0.6477	Remote Similarity	NPD3062	Approved
0.6477	Remote Similarity	NPD3061	Approved
0.6477	Remote Similarity	NPD3059	Approved
0.6467	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3536	Discontinued
0.6467	Remote Similarity	NPD3985	Discontinued
0.6455	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6583	Phase 3
0.6433	Remote Similarity	NPD6582	Phase 2
0.6429	Remote Similarity	NPD8252	Approved
0.6429	Remote Similarity	NPD8099	Discontinued
0.6429	Remote Similarity	NPD8251	Approved
0.6425	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7007	Discovery
0.6413	Remote Similarity	NPD7212	Phase 2
0.6413	Remote Similarity	NPD1774	Approved
0.6413	Remote Similarity	NPD7213	Phase 3
0.6409	Remote Similarity	NPD7037	Approved
0.6402	Remote Similarity	NPD5722	Discontinued
0.6393	Remote Similarity	NPD2677	Approved
0.6392	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7447	Phase 1
0.6368	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5718	Phase 2
0.6359	Remote Similarity	NPD6687	Approved
0.6359	Remote Similarity	NPD6688	Approved
0.6355	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4055	Discovery
0.6344	Remote Similarity	NPD2183	Approved
0.6344	Remote Similarity	NPD2184	Approved
0.6343	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2563	Approved
0.6335	Remote Similarity	NPD2560	Approved
0.6328	Remote Similarity	NPD1423	Approved
0.6328	Remote Similarity	NPD840	Approved
0.6328	Remote Similarity	NPD839	Approved
0.6318	Remote Similarity	NPD7311	Approved
0.6318	Remote Similarity	NPD7313	Approved
0.6318	Remote Similarity	NPD7312	Approved
0.6318	Remote Similarity	NPD7310	Approved
0.6308	Remote Similarity	NPD6071	Discontinued
0.6304	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD2922	Phase 1
0.6294	Remote Similarity	NPD9381	Approved
0.6294	Remote Similarity	NPD9384	Approved
0.6289	Remote Similarity	NPD4666	Phase 3
0.6287	Remote Similarity	NPD7309	Approved
0.6286	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD5177	Phase 3
0.6279	Remote Similarity	NPD2231	Phase 2
0.6279	Remote Similarity	NPD2235	Phase 2
0.6276	Remote Similarity	NPD4083	Discontinued
0.6271	Remote Similarity	NPD5110	Phase 2
0.6271	Remote Similarity	NPD5109	Approved
0.6271	Remote Similarity	NPD5111	Phase 2
0.6269	Remote Similarity	NPD5604	Discontinued
0.6263	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6063	Approved
0.6244	Remote Similarity	NPD2843	Phase 2
0.6244	Remote Similarity	NPD2845	Phase 2
0.6243	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD9622	Approved
0.6243	Remote Similarity	NPD1669	Approved
0.6237	Remote Similarity	NPD5709	Phase 3
0.623	Remote Similarity	NPD4433	Discontinued
0.6229	Remote Similarity	NPD7451	Discontinued
0.6224	Remote Similarity	NPD7608	Discontinued
0.6223	Remote Similarity	NPD6031	Approved
0.6223	Remote Similarity	NPD6030	Approved
0.6222	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3692	Discontinued
0.6215	Remote Similarity	NPD3179	Approved
0.6215	Remote Similarity	NPD3180	Approved
0.6211	Remote Similarity	NPD3296	Phase 1
0.6205	Remote Similarity	NPD821	Approved
0.6203	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD7020	Approved
0.6203	Remote Similarity	NPD7019	Approved
0.6198	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5061	Approved
0.6196	Remote Similarity	NPD2460	Phase 3
0.6196	Remote Similarity	NPD5062	Approved
0.6196	Remote Similarity	NPD2459	Approved
0.6196	Remote Similarity	NPD2458	Approved
0.6193	Remote Similarity	NPD4993	Discontinued
0.619	Remote Similarity	NPD4210	Discontinued
0.6188	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6896	Approved
0.6188	Remote Similarity	NPD2802	Phase 3
0.6188	Remote Similarity	NPD6895	Approved
0.6185	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD7124	Phase 2
0.618	Remote Similarity	NPD601	Approved
0.618	Remote Similarity	NPD598	Approved
0.618	Remote Similarity	NPD597	Approved
0.618	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD4773	Phase 2
0.6178	Remote Similarity	NPD4772	Phase 2
0.6178	Remote Similarity	NPD7438	Suspended
0.6175	Remote Similarity	NPD3656	Approved
0.6165	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6166	Phase 2
0.6162	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD3455	Phase 2
0.6158	Remote Similarity	NPD4908	Phase 1
0.6158	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7125	Discontinued
0.615	Remote Similarity	NPD6042	Phase 2
0.615	Remote Similarity	NPD6087	Phase 1
0.615	Remote Similarity	NPD42	Phase 2
0.615	Remote Similarity	NPD4357	Discontinued
0.6149	Remote Similarity	NPD3685	Discontinued
0.6145	Remote Similarity	NPD3532	Approved
0.6145	Remote Similarity	NPD3530	Approved
0.6145	Remote Similarity	NPD228	Approved
0.6145	Remote Similarity	NPD3531	Approved
0.6145	Remote Similarity	NPD1136	Approved
0.6145	Remote Similarity	NPD1132	Approved
0.6145	Remote Similarity	NPD1130	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