NPASS Compound

Structure

CID257143 OpenBabel06191716062D 55 58 0 0 0 0 0 0 0 0999 V2000 5.4984 2.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0337 4.0074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5455 -3.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9468 -4.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3273 5.8615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2924 -1.2271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4158 5.1924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6655 2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9726 5.9126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7046 -2.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5963 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7211 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3395 3.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1278 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6453 3.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3088 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4863 4.5743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8912 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 3.9052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4844 0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4373 4.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3034 -1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9021 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9021 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2905 3.3383 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5400 -3.4451 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -2.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2784 5.5525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8857 -0.3136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 4.2142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0722 1.5135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1805 4.9344 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3.7101 -1.9316 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 0.3090 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 1.8090 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.6180 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 40 1 0 0 0 0 2 40 1 0 0 0 0 3 41 1 0 0 0 0 4 41 1 0 0 0 0 5 42 1 0 0 0 0 6 42 1 0 0 0 0 7 43 1 0 0 0 0 8 44 1 0 0 0 0 9 45 1 0 0 0 0 10 46 1 0 0 0 0 11 47 1 0 0 0 0 12 48 1 0 0 0 0 13 49 1 0 0 0 0 14 50 1 0 0 0 0 15 51 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 18 24 1 0 0 0 0 19 40 1 0 0 0 0 20 41 1 0 0 0 0 21 42 1 0 0 0 0 22 31 2 0 0 0 0 22 34 1 0 0 0 0 23 32 2 0 0 0 0 23 35 1 0 0 0 0 24 33 2 0 0 0 0 24 36 1 0 0 0 0 25 28 2 0 0 0 0 25 31 1 0 0 0 0 25 43 1 0 0 0 0 26 29 2 0 0 0 0 26 32 1 0 0 0 0 26 44 1 0 0 0 0 27 30 2 0 0 0 0 27 33 1 0 0 0 0 27 45 1 0 0 0 0 28 37 1 0 0 0 0 28 46 1 0 0 0 0 29 38 1 0 0 0 0 29 47 1 0 0 0 0 30 39 1 0 0 0 0 30 48 1 0 0 0 0 31 49 1 0 0 0 0 32 50 1 0 0 0 0 33 51 1 0 0 0 0 34 37 2 0 0 0 0 34 52 1 0 0 0 0 35 38 2 0 0 0 0 35 54 1 0 0 0 0 36 39 2 0 0 0 0 36 55 1 0 0 0 0 37 53 1 0 0 0 0 38 52 1 0 0 0 0 39 53 1 0 0 0 0 54 55 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	887.23
Volume:	840.441
LogP:	7.48
LogD:	4.63
LogS:	-6.662
# Rotatable Bonds:	18
TPSA:	65.1
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.071
Synthetic Accessibility Score:	4.472
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.252
MDCK Permeability:	1.7247315554413944e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.823
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	94.34842681884766%
Volume Distribution (VD):	1.036
Pgp-substrate:	3.7153356075286865%

ADMET: Metabolism

CYP1A2-inhibitor:	0.293
CYP1A2-substrate:	0.996
CYP2C19-inhibitor:	0.269
CYP2C19-substrate:	0.998
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.97
CYP3A4-inhibitor:	0.334
CYP3A4-substrate:	0.975

ADMET: Excretion

Clearance (CL):	5.735
Half-life (T1/2):	0.002

ADMET: Toxicity

hERG Blockers:	0.859
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.984
Maximum Recommended Daily Dose:	0.126
Skin Sensitization:	0.178
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC257143

Natural Product ID:	NPC257143
*Common Name:**	Lissoclibadin 1
IUPAC Name:	n.a.
Synonyms:	Lissoclibadin 1
Standard InCHIKey:	SYYGQWWWVKVZAF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C39H57N3O6S7/c1-40(2)19-16-22-31(49-13)25(43-7)28(46-10)37-34(22)52-38-29(47-11)26(44-8)32(50-14)23(17-20-41(3)4)35(38)54-55-36-24(18-21-42(5)6)33(51-15)27(45-9)30(48-12)39(36)53-37/h16-21H2,1-15H3
SMILES:	CN(C)CCc1c(c(c(c2c1sc1c(c(c(c(CCN(C)C)c1ssc1c(CCN(C)C)c(c(c(c1s2)OC)OC)SC)SC)OC)OC)OC)OC)SC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL436519
PubChem CID:	11480314
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO30532	Lissoclinum badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17268087]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17269824]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18977148]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28181805]

☑ 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
EC50	1
IC50	4
Others	6

Activity Type	# Activity
Cell Line	9
CELL-LINE	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	4000.0	nM	PMID[468211]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7600.0	nM	PMID[468211]
NPT2451	Cell Line	NCI-H28	Homo sapiens	IC50	=	7100.0	nM	PMID[468211]
NPT148	Cell Line	HCT-15	Homo sapiens	Activity	=	11.0	%	PMID[468211]
NPT148	Cell Line	HCT-15	Homo sapiens	Activity	=	37.0	%	PMID[468211]
NPT148	Cell Line	HCT-15	Homo sapiens	Activity	=	43.0	%	PMID[468211]
NPT148	Cell Line	HCT-15	Homo sapiens	Activity	=	40.0	%	PMID[468211]
NPT148	Cell Line	HCT-15	Homo sapiens	TGI	=	60.0	%	PMID[468211]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	200.0	nM	PMID[468210]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	IC50	=	6300.0	nM	PMID[468211]

☑ 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 NPC257143 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	453
0.1-0.2	3865
0.2-0.3	15283
0.3-0.4	8248
0.4-0.5	12408
0.5-0.6	2320
0.6-0.7	101
0.7-0.8	8
0.8-0.85	1
0.85-0.9	4
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.953	High Similarity	NPC28414
0.953	High Similarity	NPC298924
0.9467	High Similarity	NPC291583
0.9467	High Similarity	NPC191200
0.8933	High Similarity	NPC69623
0.8933	High Similarity	NPC226601
0.8712	High Similarity	NPC177023
0.8704	High Similarity	NPC130921
0.8282	Intermediate Similarity	NPC94292
0.8037	Intermediate Similarity	NPC131440
0.7962	Intermediate Similarity	NPC261940
0.7607	Intermediate Similarity	NPC296858
0.7438	Intermediate Similarity	NPC59661
0.7407	Intermediate Similarity	NPC474553
0.7346	Intermediate Similarity	NPC475698
0.7273	Intermediate Similarity	NPC474649
0.7273	Intermediate Similarity	NPC474652
0.6727	Remote Similarity	NPC167944
0.6727	Remote Similarity	NPC231884
0.6727	Remote Similarity	NPC42793
0.6667	Remote Similarity	NPC11147
0.6646	Remote Similarity	NPC172403
0.6485	Remote Similarity	NPC118419
0.6471	Remote Similarity	NPC213206
0.6471	Remote Similarity	NPC474915
0.6471	Remote Similarity	NPC188163
0.6471	Remote Similarity	NPC323204
0.6471	Remote Similarity	NPC328750
0.6448	Remote Similarity	NPC206941
0.6441	Remote Similarity	NPC206372
0.6441	Remote Similarity	NPC203424
0.6438	Remote Similarity	NPC298486
0.6425	Remote Similarity	NPC247639
0.6425	Remote Similarity	NPC25084
0.6416	Remote Similarity	NPC145304
0.6412	Remote Similarity	NPC314682
0.64	Remote Similarity	NPC130941
0.6395	Remote Similarity	NPC476567
0.6395	Remote Similarity	NPC136860
0.6395	Remote Similarity	NPC128019
0.638	Remote Similarity	NPC301713
0.6364	Remote Similarity	NPC160193
0.6364	Remote Similarity	NPC211296
0.6337	Remote Similarity	NPC100478
0.6337	Remote Similarity	NPC222039
0.6322	Remote Similarity	NPC5462
0.6294	Remote Similarity	NPC193528
0.6287	Remote Similarity	NPC214869
0.6271	Remote Similarity	NPC219162
0.6271	Remote Similarity	NPC92541
0.625	Remote Similarity	NPC210437
0.625	Remote Similarity	NPC475393
0.625	Remote Similarity	NPC476144
0.625	Remote Similarity	NPC51957
0.625	Remote Similarity	NPC106295
0.625	Remote Similarity	NPC16107
0.6229	Remote Similarity	NPC185838
0.6228	Remote Similarity	NPC476570
0.6228	Remote Similarity	NPC114102
0.6215	Remote Similarity	NPC476571
0.6215	Remote Similarity	NPC135538
0.6215	Remote Similarity	NPC428
0.6215	Remote Similarity	NPC475959
0.6215	Remote Similarity	NPC7467
0.6215	Remote Similarity	NPC246587
0.6215	Remote Similarity	NPC147390
0.6215	Remote Similarity	NPC24233
0.6193	Remote Similarity	NPC473934
0.6188	Remote Similarity	NPC187022
0.6188	Remote Similarity	NPC244112
0.6188	Remote Similarity	NPC80129
0.6183	Remote Similarity	NPC42549
0.6183	Remote Similarity	NPC268503
0.6183	Remote Similarity	NPC317272
0.6183	Remote Similarity	NPC250846
0.6183	Remote Similarity	NPC256012
0.6183	Remote Similarity	NPC240841
0.6168	Remote Similarity	NPC52029
0.6168	Remote Similarity	NPC195749
0.6168	Remote Similarity	NPC35961
0.6168	Remote Similarity	NPC262641
0.6167	Remote Similarity	NPC114124
0.6164	Remote Similarity	NPC120075
0.6158	Remote Similarity	NPC476151
0.6158	Remote Similarity	NPC191376
0.6158	Remote Similarity	NPC20395
0.6158	Remote Similarity	NPC253883
0.6158	Remote Similarity	NPC179825
0.6158	Remote Similarity	NPC321505
0.6158	Remote Similarity	NPC144863
0.6158	Remote Similarity	NPC90844
0.6158	Remote Similarity	NPC95075
0.6154	Remote Similarity	NPC186063
0.6145	Remote Similarity	NPC220858
0.6145	Remote Similarity	NPC192768
0.6145	Remote Similarity	NPC88249
0.6145	Remote Similarity	NPC97221
0.6145	Remote Similarity	NPC151895
0.6111	Remote Similarity	NPC476568
0.6111	Remote Similarity	NPC127402
0.6111	Remote Similarity	NPC81733
0.6111	Remote Similarity	NPC326316
0.6108	Remote Similarity	NPC155838
0.6099	Remote Similarity	NPC99659
0.6099	Remote Similarity	NPC325871
0.6089	Remote Similarity	NPC477565
0.6089	Remote Similarity	NPC103379
0.6087	Remote Similarity	NPC186595
0.6087	Remote Similarity	NPC216816
0.6085	Remote Similarity	NPC164608
0.6082	Remote Similarity	NPC475828
0.6077	Remote Similarity	NPC233029
0.6077	Remote Similarity	NPC210148
0.6069	Remote Similarity	NPC210086
0.6059	Remote Similarity	NPC160692
0.6056	Remote Similarity	NPC13397
0.6054	Remote Similarity	NPC46067
0.6053	Remote Similarity	NPC63646
0.6053	Remote Similarity	NPC10908
0.6053	Remote Similarity	NPC227060
0.6053	Remote Similarity	NPC76682
0.6053	Remote Similarity	NPC276890
0.6053	Remote Similarity	NPC317439
0.6053	Remote Similarity	NPC317145
0.6053	Remote Similarity	NPC115284
0.6053	Remote Similarity	NPC198498
0.6048	Remote Similarity	NPC186898
0.6048	Remote Similarity	NPC153990
0.6048	Remote Similarity	NPC251571
0.6047	Remote Similarity	NPC7018
0.6047	Remote Similarity	NPC301050
0.6047	Remote Similarity	NPC131204
0.6047	Remote Similarity	NPC416184
0.6045	Remote Similarity	NPC110337
0.6045	Remote Similarity	NPC130926
0.6038	Remote Similarity	NPC47194
0.6033	Remote Similarity	NPC476572
0.6022	Remote Similarity	NPC8337
0.6022	Remote Similarity	NPC60186
0.6022	Remote Similarity	NPC85747
0.6021	Remote Similarity	NPC251580
0.6021	Remote Similarity	NPC41376
0.6021	Remote Similarity	NPC12424
0.6021	Remote Similarity	NPC129518
0.6013	Remote Similarity	NPC165106
0.6012	Remote Similarity	NPC14600
0.6012	Remote Similarity	NPC41473
0.6012	Remote Similarity	NPC312770
0.6012	Remote Similarity	NPC160607
0.6012	Remote Similarity	NPC204848
0.6012	Remote Similarity	NPC253429
0.6011	Remote Similarity	NPC193949
0.6011	Remote Similarity	NPC138487
0.6011	Remote Similarity	NPC93593
0.6011	Remote Similarity	NPC189266
0.6011	Remote Similarity	NPC2413
0.6011	Remote Similarity	NPC110416
0.6011	Remote Similarity	NPC172765
0.6011	Remote Similarity	NPC276588
0.6011	Remote Similarity	NPC39701
0.6011	Remote Similarity	NPC469817
0.6011	Remote Similarity	NPC54379
0.6011	Remote Similarity	NPC5238
0.6011	Remote Similarity	NPC278799
0.6011	Remote Similarity	NPC207757
0.6011	Remote Similarity	NPC204828
0.6011	Remote Similarity	NPC127674
0.6011	Remote Similarity	NPC216459
0.6011	Remote Similarity	NPC184026
0.6011	Remote Similarity	NPC41178
0.6011	Remote Similarity	NPC249797
0.6011	Remote Similarity	NPC295691
0.6011	Remote Similarity	NPC107602
0.6	Remote Similarity	NPC182119
0.6	Remote Similarity	NPC9341
0.6	Remote Similarity	NPC81067
0.6	Remote Similarity	NPC207824
0.6	Remote Similarity	NPC60538
0.5989	Remote Similarity	NPC26601
0.5989	Remote Similarity	NPC233650
0.5978	Remote Similarity	NPC146288
0.5978	Remote Similarity	NPC115144
0.5978	Remote Similarity	NPC277857
0.5977	Remote Similarity	NPC299583
0.5969	Remote Similarity	NPC475215
0.5969	Remote Similarity	NPC108434
0.5967	Remote Similarity	NPC478189
0.5965	Remote Similarity	NPC6854
0.5965	Remote Similarity	NPC313737
0.5965	Remote Similarity	NPC285078
0.5964	Remote Similarity	NPC105513
0.5959	Remote Similarity	NPC293093
0.5959	Remote Similarity	NPC32064
0.5957	Remote Similarity	NPC134858
0.5957	Remote Similarity	NPC121275
0.5957	Remote Similarity	NPC284183
0.5957	Remote Similarity	NPC4138
0.5956	Remote Similarity	NPC292003
0.5956	Remote Similarity	NPC475557
0.5951	Remote Similarity	NPC321133

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 NPC257143 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	1084
0.2-0.3	2021
0.3-0.4	3292
0.4-0.5	1927
0.5-0.6	535
0.6-0.7	44
0.7-0.8	0
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
0.7143	Intermediate Similarity	NPD7802	Discontinued
0.6944	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5718	Phase 2
0.6813	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6896	Approved
0.6727	Remote Similarity	NPD6895	Approved
0.6607	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4180	Approved
0.6441	Remote Similarity	NPD4179	Approved
0.6416	Remote Similarity	NPD7124	Phase 2
0.6404	Remote Similarity	NPD1757	Discontinued
0.6391	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5241	Discontinued
0.6344	Remote Similarity	NPD730	Discontinued
0.6322	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6066	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7905	Discontinued
0.6271	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1642	Discontinued
0.625	Remote Similarity	NPD4584	Approved
0.625	Remote Similarity	NPD4739	Approved
0.6243	Remote Similarity	NPD487	Discontinued
0.6243	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD3060	Approved
0.6243	Remote Similarity	NPD4162	Approved
0.6222	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7110	Phase 1
0.6215	Remote Similarity	NPD2236	Approved
0.6188	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD7298	Approved
0.6167	Remote Similarity	NPD6875	Approved
0.6167	Remote Similarity	NPD6876	Approved
0.6158	Remote Similarity	NPD6322	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7015	Phase 2
0.6117	Remote Similarity	NPD7016	Phase 3
0.6114	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6031	Approved
0.6089	Remote Similarity	NPD6030	Approved
0.6087	Remote Similarity	NPD6788	Approved
0.6087	Remote Similarity	NPD3075	Approved
0.6082	Remote Similarity	NPD2653	Approved
0.6061	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD7833	Phase 2
0.6054	Remote Similarity	NPD7831	Phase 2
0.6053	Remote Similarity	NPD8099	Discontinued
0.6053	Remote Similarity	NPD8252	Approved
0.6053	Remote Similarity	NPD8251	Approved
0.6051	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6111	Discontinued
0.6037	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6890	Discontinued
0.6022	Remote Similarity	NPD4017	Approved
0.6021	Remote Similarity	NPD8156	Discontinued
0.6013	Remote Similarity	NPD5283	Phase 1
0.6011	Remote Similarity	NPD5720	Discontinued
0.6	Remote Similarity	NPD554	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD2644	Approved
0.5989	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4123	Phase 3
0.5966	Remote Similarity	NPD4236	Phase 3
0.5966	Remote Similarity	NPD5177	Phase 3
0.5966	Remote Similarity	NPD4237	Approved
0.5964	Remote Similarity	NPD2922	Phase 1
0.5956	Remote Similarity	NPD6873	Phase 2
0.5951	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD2667	Approved
0.5951	Remote Similarity	NPD2668	Approved
0.5941	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6331	Phase 2
0.592	Remote Similarity	NPD6493	Phase 3
0.5912	Remote Similarity	NPD3640	Phase 3
0.5912	Remote Similarity	NPD3641	Approved
0.5912	Remote Similarity	NPD2901	Approved
0.5912	Remote Similarity	NPD3639	Approved
0.5912	Remote Similarity	NPD2900	Approved
0.5906	Remote Similarity	NPD2674	Phase 3
0.5893	Remote Similarity	NPD6584	Phase 3
0.5892	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.589	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4772	Phase 2
0.587	Remote Similarity	NPD6386	Approved
0.587	Remote Similarity	NPD4773	Phase 2
0.587	Remote Similarity	NPD6385	Approved
0.5856	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD746	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6813	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD8054	Approved
0.5838	Remote Similarity	NPD8053	Approved
0.5833	Remote Similarity	NPD3124	Discontinued
0.5828	Remote Similarity	NPD6581	Approved
0.5828	Remote Similarity	NPD2486	Discontinued
0.5828	Remote Similarity	NPD6580	Approved
0.5819	Remote Similarity	NPD7153	Discontinued
0.5818	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD4678	Approved
0.5815	Remote Similarity	NPD4675	Approved
0.5814	Remote Similarity	NPD4475	Approved
0.5814	Remote Similarity	NPD4474	Approved
0.5814	Remote Similarity	NPD3530	Approved
0.5814	Remote Similarity	NPD3531	Approved
0.5814	Remote Similarity	NPD3532	Approved
0.5806	Remote Similarity	NPD2978	Approved
0.5806	Remote Similarity	NPD5773	Approved
0.5806	Remote Similarity	NPD5772	Approved
0.5806	Remote Similarity	NPD2977	Approved
0.5805	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.5801	Remote Similarity	NPD1424	Approved
0.5792	Remote Similarity	NPD4210	Discontinued
0.5789	Remote Similarity	NPD6107	Approved
0.5784	Remote Similarity	NPD7034	Discontinued
0.578	Remote Similarity	NPD3110	Approved
0.578	Remote Similarity	NPD3109	Approved
0.5774	Remote Similarity	NPD5310	Approved
0.5774	Remote Similarity	NPD5311	Approved
0.5773	Remote Similarity	NPD7719	Discontinued
0.5763	Remote Similarity	NPD1803	Phase 3
0.5761	Remote Similarity	NPD4005	Discontinued
0.5759	Remote Similarity	NPD4010	Discontinued
0.5758	Remote Similarity	NPD4483	Discontinued
0.5756	Remote Similarity	NPD3144	Approved
0.5756	Remote Similarity	NPD5109	Approved
0.5756	Remote Similarity	NPD5110	Phase 2
0.5756	Remote Similarity	NPD5111	Phase 2
0.5756	Remote Similarity	NPD3145	Approved
0.5749	Remote Similarity	NPD2233	Approved
0.5749	Remote Similarity	NPD2232	Approved
0.5749	Remote Similarity	NPD2230	Approved
0.5747	Remote Similarity	NPD3657	Discovery
0.574	Remote Similarity	NPD4098	Discontinued
0.5739	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.5737	Remote Similarity	NPD5677	Discontinued
0.573	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6989	Approved
0.5729	Remote Similarity	NPD6687	Approved
0.5729	Remote Similarity	NPD6688	Approved
0.5729	Remote Similarity	NPD6990	Approved
0.5722	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD6064	Phase 1
0.5722	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2759	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1669	Approved
0.5714	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6583	Phase 3
0.5714	Remote Similarity	NPD2492	Phase 1
0.5714	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5604	Discontinued
0.5714	Remote Similarity	NPD6582	Phase 2
0.5707	Remote Similarity	NPD3687	Approved
0.5707	Remote Similarity	NPD3686	Approved
0.5706	Remote Similarity	NPD3539	Phase 1
0.5706	Remote Similarity	NPD2161	Phase 2
0.5706	Remote Similarity	NPD7018	Phase 2
0.5699	Remote Similarity	NPD7438	Suspended
0.5697	Remote Similarity	NPD6382	Discontinued
0.5694	Remote Similarity	NPD8015	Phase 3
0.5691	Remote Similarity	NPD5978	Approved
0.5691	Remote Similarity	NPD5977	Approved
0.569	Remote Similarity	NPD2238	Phase 2
0.5678	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.5677	Remote Similarity	NPD6071	Discontinued
0.5677	Remote Similarity	NPD3051	Approved
0.5674	Remote Similarity	NPD1375	Discontinued
0.5674	Remote Similarity	NPD3540	Phase 1
0.5671	Remote Similarity	NPD5536	Phase 2
0.567	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5754	Discontinued
0.5661	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.565	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD3055	Approved
0.5647	Remote Similarity	NPD3053	Approved
0.5635	Remote Similarity	NPD6297	Approved
0.5635	Remote Similarity	NPD3301	Approved
0.5632	Remote Similarity	NPD2245	Discovery
0.5632	Remote Similarity	NPD7265	Discontinued
0.5631	Remote Similarity	NPD5564	Approved
0.5628	Remote Similarity	NPD7020	Approved
0.5628	Remote Similarity	NPD7019	Approved
0.5625	Remote Similarity	NPD5314	Approved
0.5621	Remote Similarity	NPD6543	Approved
0.5621	Remote Similarity	NPD6540	Phase 3
0.5621	Remote Similarity	NPD6539	Approved
0.5621	Remote Similarity	NPD6542	Approved
0.5619	Remote Similarity	NPD4481	Phase 3
0.5612	Remote Similarity	NPD5312	Approved
0.5612	Remote Similarity	NPD5313	Approved
0.5611	Remote Similarity	NPD3599	Approved
0.561	Remote Similarity	NPD3596	Phase 2
0.5608	Remote Similarity	NPD2563	Approved
0.5608	Remote Similarity	NPD7738	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