NPASS Compound

Structure

NPC475534 OpenBabel07101719252D 54 59 0 0 1 0 0 0 0 0999 V2000 -4.7129 3.3441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3902 3.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0993 -3.3999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5114 3.6549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6719 -1.0756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3788 -1.6995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2781 -0.5099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6920 -1.7576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5913 -0.5680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1433 2.1456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6113 -1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7513 -0.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8469 0.7298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6979 -1.6979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.2430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0822 2.9093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3707 -2.8874 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0969 2.9751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2982 -1.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7213 1.5062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1981 -0.6984 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9869 -0.2390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4191 0.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9409 -1.6979 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6215 2.3194 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1344 -2.0286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3284 2.5510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6009 -1.0294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0848 1.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0604 -2.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2340 -1.5888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0550 2.1961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3623 2.5741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9946 0.7114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4346 -0.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9572 1.4503 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4905 -0.7305 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8143 -0.8735 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6335 1.5933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3670 0.2584 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0807 0.4614 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6223 -1.2832 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8254 2.0030 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5626 -3.2622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9496 -1.7326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4729 2.3346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7944 -2.7390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4849 -1.9039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7465 2.5676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6139 2.9866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1086 0.0726 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.8547 0.2402 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.6215 -1.0764 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 16 1 0 0 0 0 2 16 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 19 2 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 22 2 0 0 0 0 12 51 1 0 0 0 0 13 23 2 0 0 0 0 13 52 1 0 0 0 0 14 53 1 0 0 0 0 15 54 1 0 0 0 0 17 3 1 1 0 0 0 17 44 1 0 0 0 0 18 4 1 1 0 0 0 18 27 1 0 0 0 0 18 50 1 0 0 0 0 20 10 1 1 0 0 0 20 34 1 0 0 0 0 20 36 1 0 0 0 0 21 11 1 1 0 0 0 21 35 1 0 0 0 0 21 37 1 0 0 0 0 22 28 1 0 0 0 0 22 40 1 0 0 0 0 23 29 1 0 0 0 0 23 41 1 0 0 0 0 24 14 1 1 0 0 0 24 30 1 0 0 0 0 24 38 1 0 0 0 0 25 15 1 1 0 0 0 25 33 1 0 0 0 0 25 39 1 0 0 0 0 26 17 1 6 0 0 0 26 31 1 0 0 0 0 26 42 1 0 0 0 0 27 32 1 6 0 0 0 27 43 1 0 0 0 0 28 38 2 3 0 0 0 28 45 1 0 0 0 0 29 39 2 3 0 0 0 29 46 1 0 0 0 0 30 42 2 3 0 0 0 30 47 1 0 0 0 0 31 37 2 3 0 0 0 31 48 1 0 0 0 0 32 36 2 3 0 0 0 32 49 1 0 0 0 0 33 43 2 0 0 0 0 33 50 1 0 0 0 0 34 40 2 0 0 0 0 34 51 1 0 0 0 0 35 41 2 0 0 0 0 35 52 1 0 0 0 0 53 54 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	814.21
Volume:	751.845
LogP:	5.245
LogD:	4.167
LogS:	-4.97
# Rotatable Bonds:	5
TPSA:	216.59
# H-Bond Aceptor:	15
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.205
Synthetic Accessibility Score:	7.361
Fsp3:	0.486
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.923
MDCK Permeability:	1.9652397895697504e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.269
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	40.526756286621094%
Volume Distribution (VD):	0.469
Pgp-substrate:	45.189849853515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.212
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.748
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.627
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	2.579
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.08
Carcinogencity:	0.085
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC475534

Natural Product ID:	NPC475534
*Common Name:**	Ulithiacyclamide G
IUPAC Name:	n.a.
Synonyms:	Ulithiacyclamide G
Standard InCHIKey:	XTSHAALAASYFFM-NYVLYJCUSA-N
Standard InCHI:	InChI=1S/C35H42N8O7S4/c1-16(2)10-20-34-40-22(12-51-34)28(45)38-24-14-53-54-15-25(33-43-27(18(4)50-33)32(49)36-20)39-29(46)23-13-52-35(41-23)21(11-19-8-6-5-7-9-19)37-31(48)26(17(3)44)42-30(24)47/h5-9,12-13,16-18,20-21,24-27,44H,10-11,14-15H2,1-4H3,(H,36,49)(H,37,48)(H,38,45)(H,39,46)(H,42,47)/t17-,18+,20+,21+,24+,25+,26-,27-/m0/s1
SMILES:	CC1C2C(=O)NC(C3=NC(=CS3)C(=O)NC4CSSCC(C(=N2)O1)NC(=O)C5=CSC(=N5)C(NC(=O)C(NC4=O)C(C)O)CC6=CC=CC=C6)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507568
PubChem CID:	21775221
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0001995] Cyclic peptides

*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
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593285]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2095371]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2809606]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623037]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868162]
NPO4712	Lissoclinum patella	Species	Didemnidae	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
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	90.0	nM	PMID[496243]

☑ 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 NPC475534 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	226
0.1-0.2	2308
0.2-0.3	15534
0.3-0.4	18031
0.4-0.5	5132
0.5-0.6	1385
0.6-0.7	52
0.7-0.8	18
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476080
0.9874	High Similarity	NPC161242
0.9752	High Similarity	NPC174652
0.9689	High Similarity	NPC475330
0.963	High Similarity	NPC229160
0.963	High Similarity	NPC263485
0.963	High Similarity	NPC25316
0.956	High Similarity	NPC476103
0.9018	High Similarity	NPC24990
0.8011	Intermediate Similarity	NPC329961
0.7923	Intermediate Similarity	NPC165538
0.7912	Intermediate Similarity	NPC122427
0.7889	Intermediate Similarity	NPC96016
0.7692	Intermediate Similarity	NPC49051
0.7516	Intermediate Similarity	NPC120917
0.7421	Intermediate Similarity	NPC89592
0.7346	Intermediate Similarity	NPC74917
0.7323	Intermediate Similarity	NPC475350
0.7323	Intermediate Similarity	NPC14877
0.7323	Intermediate Similarity	NPC145178
0.73	Intermediate Similarity	NPC251036
0.7278	Intermediate Similarity	NPC51692
0.7204	Intermediate Similarity	NPC161143
0.7188	Intermediate Similarity	NPC106235
0.7188	Intermediate Similarity	NPC239660
0.7035	Intermediate Similarity	NPC319751
0.6962	Remote Similarity	NPC214375
0.6957	Remote Similarity	NPC267605
0.6954	Remote Similarity	NPC473398
0.6914	Remote Similarity	NPC119481
0.6875	Remote Similarity	NPC135558
0.6837	Remote Similarity	NPC469858
0.6763	Remote Similarity	NPC469801
0.6728	Remote Similarity	NPC475196
0.665	Remote Similarity	NPC75498
0.6597	Remote Similarity	NPC313966
0.6597	Remote Similarity	NPC314254
0.6591	Remote Similarity	NPC475390
0.6573	Remote Similarity	NPC283783
0.6524	Remote Similarity	NPC475920
0.6509	Remote Similarity	NPC79386
0.6489	Remote Similarity	NPC470146
0.6489	Remote Similarity	NPC101980
0.6489	Remote Similarity	NPC97078
0.6477	Remote Similarity	NPC249662
0.6378	Remote Similarity	NPC315252
0.6343	Remote Similarity	NPC89489
0.6329	Remote Similarity	NPC140284
0.6329	Remote Similarity	NPC75609
0.631	Remote Similarity	NPC475568
0.6298	Remote Similarity	NPC257511
0.6294	Remote Similarity	NPC475604
0.6269	Remote Similarity	NPC318930
0.6269	Remote Similarity	NPC317362
0.6257	Remote Similarity	NPC237219
0.625	Remote Similarity	NPC478030
0.6198	Remote Similarity	NPC164006
0.6186	Remote Similarity	NPC317725
0.6186	Remote Similarity	NPC326407
0.6158	Remote Similarity	NPC103268
0.6136	Remote Similarity	NPC474070
0.6099	Remote Similarity	NPC470824
0.6089	Remote Similarity	NPC188104
0.6066	Remote Similarity	NPC214827
0.6066	Remote Similarity	NPC314930
0.6054	Remote Similarity	NPC474079
0.6054	Remote Similarity	NPC157194
0.6054	Remote Similarity	NPC474080
0.6054	Remote Similarity	NPC21449
0.6054	Remote Similarity	NPC474102
0.6054	Remote Similarity	NPC475683
0.6043	Remote Similarity	NPC268063
0.6043	Remote Similarity	NPC224609
0.6041	Remote Similarity	NPC132662
0.6027	Remote Similarity	NPC49195
0.6011	Remote Similarity	NPC474069
0.6008	Remote Similarity	NPC197881
0.6	Remote Similarity	NPC474064
0.6	Remote Similarity	NPC82436
0.6	Remote Similarity	NPC231110
0.6	Remote Similarity	NPC7817
0.6	Remote Similarity	NPC475168
0.6	Remote Similarity	NPC474068
0.6	Remote Similarity	NPC474103
0.5989	Remote Similarity	NPC154873
0.5989	Remote Similarity	NPC61667
0.5989	Remote Similarity	NPC45576
0.5989	Remote Similarity	NPC14101
0.5989	Remote Similarity	NPC474090
0.5989	Remote Similarity	NPC32583
0.5989	Remote Similarity	NPC163147
0.5989	Remote Similarity	NPC109498
0.5989	Remote Similarity	NPC50274
0.5989	Remote Similarity	NPC252616
0.5981	Remote Similarity	NPC475024
0.5972	Remote Similarity	NPC182507
0.5969	Remote Similarity	NPC312887
0.5969	Remote Similarity	NPC522
0.5969	Remote Similarity	NPC56058
0.5947	Remote Similarity	NPC474538
0.5947	Remote Similarity	NPC127775
0.5943	Remote Similarity	NPC138562
0.5943	Remote Similarity	NPC300315
0.5938	Remote Similarity	NPC315061
0.5936	Remote Similarity	NPC475737
0.5936	Remote Similarity	NPC474094
0.5936	Remote Similarity	NPC185665
0.5936	Remote Similarity	NPC474067
0.5934	Remote Similarity	NPC476978
0.5922	Remote Similarity	NPC315411
0.5905	Remote Similarity	NPC313421
0.5904	Remote Similarity	NPC206724
0.5904	Remote Similarity	NPC474515
0.5904	Remote Similarity	NPC470902
0.59	Remote Similarity	NPC164228
0.5897	Remote Similarity	NPC34319
0.5882	Remote Similarity	NPC238242
0.5872	Remote Similarity	NPC46427
0.5872	Remote Similarity	NPC31385
0.5872	Remote Similarity	NPC75726
0.5872	Remote Similarity	NPC110602
0.587	Remote Similarity	NPC190329
0.5864	Remote Similarity	NPC52587
0.5859	Remote Similarity	NPC477462
0.5848	Remote Similarity	NPC253987
0.5843	Remote Similarity	NPC287401
0.5842	Remote Similarity	NPC202591
0.5842	Remote Similarity	NPC470507
0.5842	Remote Similarity	NPC212214
0.5842	Remote Similarity	NPC163055
0.5829	Remote Similarity	NPC24594
0.5829	Remote Similarity	NPC472122
0.5814	Remote Similarity	NPC252878
0.5812	Remote Similarity	NPC21126
0.5806	Remote Similarity	NPC105717
0.5806	Remote Similarity	NPC162860
0.5795	Remote Similarity	NPC473886
0.5794	Remote Similarity	NPC478029
0.5789	Remote Similarity	NPC161108
0.5784	Remote Similarity	NPC262077
0.5784	Remote Similarity	NPC314358
0.5779	Remote Similarity	NPC473704
0.5775	Remote Similarity	NPC475506
0.5755	Remote Similarity	NPC18487
0.5753	Remote Similarity	NPC83790
0.5753	Remote Similarity	NPC128237
0.5748	Remote Similarity	NPC193761
0.5748	Remote Similarity	NPC155143
0.5744	Remote Similarity	NPC222391
0.5744	Remote Similarity	NPC476118
0.5743	Remote Similarity	NPC472105
0.5743	Remote Similarity	NPC187827
0.5736	Remote Similarity	NPC256912
0.5734	Remote Similarity	NPC478158
0.573	Remote Similarity	NPC130309
0.573	Remote Similarity	NPC316008
0.573	Remote Similarity	NPC313867
0.5729	Remote Similarity	NPC134480
0.5728	Remote Similarity	NPC329731
0.5728	Remote Similarity	NPC4910
0.5722	Remote Similarity	NPC201014
0.5722	Remote Similarity	NPC110129
0.5721	Remote Similarity	NPC326575
0.5721	Remote Similarity	NPC143325
0.5714	Remote Similarity	NPC294693
0.5714	Remote Similarity	NPC313804
0.5714	Remote Similarity	NPC59827
0.5714	Remote Similarity	NPC315804
0.5714	Remote Similarity	NPC54420
0.5714	Remote Similarity	NPC184933
0.5714	Remote Similarity	NPC475554
0.5714	Remote Similarity	NPC323927
0.5708	Remote Similarity	NPC478028
0.5708	Remote Similarity	NPC473640
0.57	Remote Similarity	NPC46413
0.57	Remote Similarity	NPC469938
0.5698	Remote Similarity	NPC476990
0.569	Remote Similarity	NPC220852
0.5686	Remote Similarity	NPC139291
0.5686	Remote Similarity	NPC472108
0.5686	Remote Similarity	NPC472109
0.5686	Remote Similarity	NPC472110
0.5684	Remote Similarity	NPC286551
0.5684	Remote Similarity	NPC148592
0.5682	Remote Similarity	NPC273714
0.5681	Remote Similarity	NPC100321
0.5678	Remote Similarity	NPC158129
0.5677	Remote Similarity	NPC477815
0.5676	Remote Similarity	NPC315283
0.5676	Remote Similarity	NPC314388
0.5665	Remote Similarity	NPC202521
0.5662	Remote Similarity	NPC107077
0.5662	Remote Similarity	NPC223791
0.5659	Remote Similarity	NPC472294
0.5658	Remote Similarity	NPC19170
0.5657	Remote Similarity	NPC470900
0.565	Remote Similarity	NPC151779
0.565	Remote Similarity	NPC34508
0.5646	Remote Similarity	NPC243716
0.5645	Remote Similarity	NPC471680

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 NPC475534 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	572
0.2-0.3	966
0.3-0.4	2325
0.4-0.5	4205
0.5-0.6	900
0.6-0.7	38
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
0.7398	Intermediate Similarity	NPD8071	Approved
0.7391	Intermediate Similarity	NPD7977	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8260	Approved
0.7188	Intermediate Similarity	NPD8339	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5634	Approved
0.6682	Remote Similarity	NPD7806	Phase 2
0.6582	Remote Similarity	NPD6349	Phase 1
0.6497	Remote Similarity	NPD2015	Discontinued
0.6359	Remote Similarity	NPD6915	Approved
0.6305	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD2957	Phase 2
0.625	Remote Similarity	NPD6888	Discontinued
0.6244	Remote Similarity	NPD3469	Phase 3
0.6244	Remote Similarity	NPD1745	Approved
0.6233	Remote Similarity	NPD5191	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD4949	Discontinued
0.6186	Remote Similarity	NPD924	Discontinued
0.6181	Remote Similarity	NPD6092	Discontinued
0.615	Remote Similarity	NPD4742	Phase 3
0.615	Remote Similarity	NPD4741	Phase 3
0.6141	Remote Similarity	NPD3575	Approved
0.6141	Remote Similarity	NPD3576	Approved
0.6127	Remote Similarity	NPD2717	Phase 2
0.6099	Remote Similarity	NPD4855	Phase 1
0.6099	Remote Similarity	NPD5502	Approved
0.6099	Remote Similarity	NPD5503	Approved
0.6099	Remote Similarity	NPD4856	Approved
0.6093	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7496	Phase 2
0.608	Remote Similarity	NPD5596	Phase 2
0.6074	Remote Similarity	NPD8284	Discontinued
0.6062	Remote Similarity	NPD4929	Approved
0.6062	Remote Similarity	NPD4928	Approved
0.6062	Remote Similarity	NPD4930	Approved
0.6059	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5828	Phase 2
0.6048	Remote Similarity	NPD3015	Discontinued
0.6048	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD3759	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD649	Clinical (unspecified phase)
0.601	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6	Remote Similarity	NPD647	Approved
0.6	Remote Similarity	NPD1005	Phase 2
0.6	Remote Similarity	NPD1004	Phase 2
0.5991	Remote Similarity	NPD8272	Phase 2
0.5989	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7711	Discontinued
0.5979	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD6308	Phase 1
0.5957	Remote Similarity	NPD6205	Discontinued
0.5949	Remote Similarity	NPD4650	Approved
0.5936	Remote Similarity	NPD6907	Phase 2
0.5936	Remote Similarity	NPD3835	Phase 3
0.5936	Remote Similarity	NPD3833	Phase 3
0.5924	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7127	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD754	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD704	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6347	Phase 2
0.5902	Remote Similarity	NPD8063	Discontinued
0.59	Remote Similarity	NPD7104	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD8408	Discontinued
0.5869	Remote Similarity	NPD6324	Phase 1
0.5862	Remote Similarity	NPD5438	Approved
0.5862	Remote Similarity	NPD5439	Approved
0.5861	Remote Similarity	NPD5461	Discontinued
0.5855	Remote Similarity	NPD7770	Phase 3
0.5847	Remote Similarity	NPD5435	Phase 1
0.5846	Remote Similarity	NPD7133	Discontinued
0.5842	Remote Similarity	NPD1597	Phase 1
0.5838	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD4509	Discontinued
0.5833	Remote Similarity	NPD3907	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD3328	Phase 2
0.5821	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6910	Phase 3
0.581	Remote Similarity	NPD1219	Approved
0.581	Remote Similarity	NPD7490	Discontinued
0.581	Remote Similarity	NPD1218	Approved
0.5799	Remote Similarity	NPD5452	Phase 2
0.5799	Remote Similarity	NPD6360	Discontinued
0.5787	Remote Similarity	NPD8322	Phase 2
0.5779	Remote Similarity	NPD1260	Approved
0.5777	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.5777	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.5774	Remote Similarity	NPD7769	Phase 3
0.576	Remote Similarity	NPD7981	Discontinued
0.5756	Remote Similarity	NPD9579	Approved
0.5755	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.5751	Remote Similarity	NPD4557	Approved
0.5748	Remote Similarity	NPD5023	Discontinued
0.5744	Remote Similarity	NPD5138	Approved
0.5744	Remote Similarity	NPD5140	Approved
0.5741	Remote Similarity	NPD7001	Phase 3
0.5741	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD5047	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD6381	Phase 2
0.573	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6911	Discontinued
0.5728	Remote Similarity	NPD2749	Discontinued
0.5723	Remote Similarity	NPD2389	Approved
0.5722	Remote Similarity	NPD7738	Approved
0.5722	Remote Similarity	NPD7737	Approved
0.5721	Remote Similarity	NPD8123	Approved
0.5721	Remote Similarity	NPD8122	Approved
0.5721	Remote Similarity	NPD8072	Approved
0.5721	Remote Similarity	NPD5144	Discontinued
0.5714	Remote Similarity	NPD7834	Approved
0.5714	Remote Similarity	NPD3395	Approved
0.5714	Remote Similarity	NPD3396	Approved
0.5708	Remote Similarity	NPD3843	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD2893	Phase 3
0.5701	Remote Similarity	NPD1881	Approved
0.5701	Remote Similarity	NPD4331	Approved
0.5699	Remote Similarity	NPD3525	Discontinued
0.5694	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.5693	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD3487	Phase 1
0.569	Remote Similarity	NPD4273	Approved
0.5689	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD8107	Approved
0.5684	Remote Similarity	NPD6819	Phase 2
0.5681	Remote Similarity	NPD7928	Approved
0.5681	Remote Similarity	NPD7929	Approved
0.5677	Remote Similarity	NPD6170	Phase 2
0.5677	Remote Similarity	NPD6978	Phase 2
0.5677	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD3848	Phase 2
0.5673	Remote Similarity	NPD3474	Discovery
0.5669	Remote Similarity	NPD8108	Approved
0.5667	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD8129	Discovery
0.566	Remote Similarity	NPD7021	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7482	Phase 2
0.5659	Remote Similarity	NPD7483	Phase 2
0.5654	Remote Similarity	NPD5663	Discontinued
0.5649	Remote Similarity	NPD5817	Discontinued
0.5648	Remote Similarity	NPD6139	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6455	Phase 3
0.5642	Remote Similarity	NPD4415	Approved
0.564	Remote Similarity	NPD7944	Discontinued
0.5637	Remote Similarity	NPD2852	Approved
0.5635	Remote Similarity	NPD5323	Approved
0.5635	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD4470	Phase 2
0.5633	Remote Similarity	NPD8075	Discontinued
0.5632	Remote Similarity	NPD6121	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD3279	Phase 2
0.5631	Remote Similarity	NPD6227	Discontinued
0.5625	Remote Similarity	NPD5523	Approved
0.5625	Remote Similarity	NPD1976	Approved
0.5625	Remote Similarity	NPD5367	Discontinued
0.5625	Remote Similarity	NPD5524	Approved
0.5622	Remote Similarity	NPD8169	Discontinued
0.5621	Remote Similarity	NPD2543	Discontinued
0.5616	Remote Similarity	NPD4960	Approved
0.5616	Remote Similarity	NPD4959	Approved
0.5614	Remote Similarity	NPD5094	Approved
0.5612	Remote Similarity	NPD3492	Approved
0.5612	Remote Similarity	NPD3493	Approved
0.5612	Remote Similarity	NPD3494	Approved
0.561	Remote Similarity	NPD5106	Approved
0.561	Remote Similarity	NPD5105	Approved
0.5608	Remote Similarity	NPD6378	Approved
0.5608	Remote Similarity	NPD7469	Discontinued
0.5604	Remote Similarity	NPD2202	Clinical (unspecified phase)
0.5602	Remote Similarity	NPD8073	Approved
0.5602	Remote Similarity	NPD1897	Discontinued

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