NPASS Compound

Structure

NPC476103 OpenBabel07101718322D 55 59 0 0 1 0 0 0 0 0999 V2000 1.9270 1.5065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2282 0.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8958 3.2396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9864 -4.0067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2357 -1.3557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0536 -2.0278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7447 -0.8619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3805 -2.2061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0716 -1.0402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5869 1.5397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2163 -1.8906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2011 -0.6443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4543 0.1094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7153 1.7153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.2557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2474 1.1363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3862 2.6875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2140 -3.5448 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8895 -1.7123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1606 0.8938 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7989 -1.3333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4289 -0.8693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0221 0.3499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9709 1.7153 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6278 -2.3431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2465 1.9492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4527 -2.6771 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0389 -1.6678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6844 1.0414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2225 1.9725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5173 -2.6489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5125 1.5907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3624 -2.2329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4366 0.0908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0378 -0.6392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6113 0.8373 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1033 -1.3658 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7557 -1.5102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9588 0.9817 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1973 -0.3668 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5172 -0.1617 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7547 1.3957 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9599 -1.9242 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6532 2.8528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4279 -3.9827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3977 -2.3913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0838 1.7434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 2.7489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7910 -3.4087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1989 1.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1021 -2.5570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5518 -0.5544 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -4.4622 -0.3852 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.6278 1.0874 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 52 1 0 0 0 0 13 23 2 0 0 0 0 13 53 1 0 0 0 0 14 54 1 0 0 0 0 15 55 1 0 0 0 0 17 3 1 6 0 0 0 17 44 1 0 0 0 0 18 4 1 1 0 0 0 18 45 1 0 0 0 0 20 10 1 6 0 0 0 20 34 1 0 0 0 0 20 36 1 0 0 0 0 21 11 1 6 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 6 0 0 0 24 30 1 0 0 0 0 24 39 1 0 0 0 0 25 15 1 6 0 0 0 25 31 1 0 0 0 0 25 38 1 0 0 0 0 26 17 1 1 0 0 0 26 32 1 0 0 0 0 26 42 1 0 0 0 0 27 18 1 1 0 0 0 27 33 1 0 0 0 0 27 43 1 0 0 0 0 28 38 2 3 0 0 0 28 46 1 0 0 0 0 29 39 2 3 0 0 0 29 47 1 0 0 0 0 30 42 2 3 0 0 0 30 48 1 0 0 0 0 31 43 2 3 0 0 0 31 49 1 0 0 0 0 32 36 2 3 0 0 0 32 50 1 0 0 0 0 33 37 2 3 0 0 0 33 51 1 0 0 0 0 34 40 2 0 0 0 0 34 52 1 0 0 0 0 35 41 2 0 0 0 0 35 53 1 0 0 0 0 54 55 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	832.22
Volume:	769.192
LogP:	2.992
LogD:	3.082
LogS:	-3.314
# Rotatable Bonds:	6
TPSA:	247.82
# H-Bond Aceptor:	16
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.167
Synthetic Accessibility Score:	7.241
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:	-6.231
MDCK Permeability:	1.2125287867092993e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.076
20% Bioavailability (F20%):	0.922
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	37.060733795166016%
Volume Distribution (VD):	0.366
Pgp-substrate:	48.279693603515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.549
CYP2C9-substrate:	0.211
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	1.907
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.989
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.054
Carcinogencity:	0.09
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC476103

Natural Product ID:	NPC476103
*Common Name:**	Ulithiacyclamide E
IUPAC Name:	n.a.
Synonyms:	Ulithiacyclamide E
Standard InCHIKey:	NLVXWJPLNQGFEL-IVNNDBPSSA-N
Standard InCHI:	InChI=1S/C35H44N8O8S4/c1-16(2)10-20-34-40-22(12-52-34)28(46)38-25-15-55-54-14-24(30(48)42-26(17(3)44)32(50)36-20)39-29(47)23-13-53-35(41-23)21(11-19-8-6-5-7-9-19)37-33(51)27(18(4)45)43-31(25)49/h5-9,12-13,16-18,20-21,24-27,44-45H,10-11,14-15H2,1-4H3,(H,36,50)(H,37,51)(H,38,46)(H,39,47)(H,42,48)(H,43,49)/t17-,18-,20+,21+,24+,25+,26-,27-/m0/s1
SMILES:	CC(C[C@H]1N=C(O)[C@@H](N=C(O)[C@H]2CSSC[C@@H](N=C(c3nc1sc3)O)C(=N[C@@H]([C@@H](O)C)C(=N[C@@H](c1nc(C(=N2)O)cs1)Cc1ccccc1)O)O)[C@@H](O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526354
PubChem CID:	21775219
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	=	112.0	nM	PMID[505310]

☑ 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 NPC476103 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	230
0.1-0.2	2327
0.2-0.3	15965
0.3-0.4	17515
0.4-0.5	5009
0.5-0.6	1568
0.6-0.7	55
0.7-0.8	18
0.8-0.85	0
0.85-0.9	1
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC476080
0.956	High Similarity	NPC475534
0.9437	High Similarity	NPC161242
0.9321	High Similarity	NPC174652
0.9259	High Similarity	NPC475330
0.9202	High Similarity	NPC229160
0.9202	High Similarity	NPC263485
0.9202	High Similarity	NPC25316
0.8598	High Similarity	NPC24990
0.8011	Intermediate Similarity	NPC96016
0.7933	Intermediate Similarity	NPC329961
0.7845	Intermediate Similarity	NPC165538
0.7833	Intermediate Similarity	NPC122427
0.7611	Intermediate Similarity	NPC49051
0.7308	Intermediate Similarity	NPC161143
0.7245	Intermediate Similarity	NPC475350
0.7245	Intermediate Similarity	NPC14877
0.7245	Intermediate Similarity	NPC145178
0.7222	Intermediate Similarity	NPC251036
0.7196	Intermediate Similarity	NPC239660
0.7196	Intermediate Similarity	NPC106235
0.719	Intermediate Similarity	NPC214375
0.7099	Intermediate Similarity	NPC120917
0.7	Intermediate Similarity	NPC89592
0.6941	Remote Similarity	NPC319751
0.6933	Remote Similarity	NPC74917
0.686	Remote Similarity	NPC473398
0.6855	Remote Similarity	NPC51692
0.6821	Remote Similarity	NPC119481
0.6748	Remote Similarity	NPC79386
0.6734	Remote Similarity	NPC75498
0.6651	Remote Similarity	NPC475196
0.6649	Remote Similarity	NPC249662
0.6612	Remote Similarity	NPC475920
0.6605	Remote Similarity	NPC469858
0.6556	Remote Similarity	NPC315252
0.6543	Remote Similarity	NPC267605
0.6503	Remote Similarity	NPC475568
0.6494	Remote Similarity	NPC475390
0.6486	Remote Similarity	NPC470146
0.6486	Remote Similarity	NPC97078
0.6486	Remote Similarity	NPC101980
0.6485	Remote Similarity	NPC475604
0.6474	Remote Similarity	NPC469801
0.646	Remote Similarity	NPC135558
0.6395	Remote Similarity	NPC75609
0.6395	Remote Similarity	NPC140284
0.6387	Remote Similarity	NPC314254
0.6387	Remote Similarity	NPC313966
0.6373	Remote Similarity	NPC257511
0.6316	Remote Similarity	NPC474070
0.6292	Remote Similarity	NPC283783
0.6245	Remote Similarity	NPC478030
0.6243	Remote Similarity	NPC89489
0.6243	Remote Similarity	NPC103268
0.6213	Remote Similarity	NPC300315
0.6195	Remote Similarity	NPC182507
0.6105	Remote Similarity	NPC287401
0.6105	Remote Similarity	NPC164006
0.6089	Remote Similarity	NPC470824
0.6087	Remote Similarity	NPC138562
0.6085	Remote Similarity	NPC110602
0.6085	Remote Similarity	NPC31385
0.6085	Remote Similarity	NPC75726
0.608	Remote Similarity	NPC188104
0.6066	Remote Similarity	NPC14101
0.6058	Remote Similarity	NPC214827
0.6058	Remote Similarity	NPC314930
0.6051	Remote Similarity	NPC164228
0.6048	Remote Similarity	NPC46427
0.6044	Remote Similarity	NPC474080
0.6044	Remote Similarity	NPC474079
0.6044	Remote Similarity	NPC474102
0.6044	Remote Similarity	NPC21449
0.6044	Remote Similarity	NPC475683
0.6044	Remote Similarity	NPC157194
0.6034	Remote Similarity	NPC190329
0.6033	Remote Similarity	NPC224609
0.6033	Remote Similarity	NPC268063
0.603	Remote Similarity	NPC238242
0.601	Remote Similarity	NPC318930
0.601	Remote Similarity	NPC317362
0.6	Remote Similarity	NPC474069
0.6	Remote Similarity	NPC470507
0.599	Remote Similarity	NPC163055
0.599	Remote Similarity	NPC475506
0.5989	Remote Similarity	NPC231110
0.5989	Remote Similarity	NPC474064
0.5989	Remote Similarity	NPC474103
0.5989	Remote Similarity	NPC7817
0.5989	Remote Similarity	NPC82436
0.5989	Remote Similarity	NPC474068
0.5989	Remote Similarity	NPC475168
0.5988	Remote Similarity	NPC130309
0.5988	Remote Similarity	NPC252878
0.5978	Remote Similarity	NPC163147
0.5978	Remote Similarity	NPC252616
0.5978	Remote Similarity	NPC32583
0.5978	Remote Similarity	NPC45576
0.5978	Remote Similarity	NPC61667
0.5978	Remote Similarity	NPC109498
0.5978	Remote Similarity	NPC474090
0.5978	Remote Similarity	NPC154873
0.5972	Remote Similarity	NPC475024
0.5962	Remote Similarity	NPC155143
0.5957	Remote Similarity	NPC312887
0.5949	Remote Similarity	NPC132662
0.5946	Remote Similarity	NPC161108
0.5945	Remote Similarity	NPC49195
0.5943	Remote Similarity	NPC162860
0.5936	Remote Similarity	NPC197881
0.5936	Remote Similarity	NPC127775
0.5936	Remote Similarity	NPC474538
0.5928	Remote Similarity	NPC317725
0.5928	Remote Similarity	NPC326407
0.5924	Remote Similarity	NPC323927
0.5924	Remote Similarity	NPC474094
0.5924	Remote Similarity	NPC185665
0.5924	Remote Similarity	NPC475737
0.5924	Remote Similarity	NPC474067
0.5922	Remote Similarity	NPC473640
0.5922	Remote Similarity	NPC476978
0.5904	Remote Similarity	NPC237219
0.5894	Remote Similarity	NPC313421
0.5894	Remote Similarity	NPC100321
0.5892	Remote Similarity	NPC474515
0.5892	Remote Similarity	NPC50274
0.5892	Remote Similarity	NPC470902
0.5892	Remote Similarity	NPC206724
0.5886	Remote Similarity	NPC141050
0.5868	Remote Similarity	NPC476990
0.5867	Remote Similarity	NPC326575
0.5866	Remote Similarity	NPC315061
0.5864	Remote Similarity	NPC473886
0.5857	Remote Similarity	NPC143325
0.5854	Remote Similarity	NPC294693
0.5851	Remote Similarity	NPC52587
0.585	Remote Similarity	NPC315411
0.5849	Remote Similarity	NPC54420
0.5848	Remote Similarity	NPC273714
0.5846	Remote Similarity	NPC477462
0.5846	Remote Similarity	NPC469938
0.5838	Remote Similarity	NPC148592
0.5833	Remote Similarity	NPC478028
0.5833	Remote Similarity	NPC202521
0.5829	Remote Similarity	NPC202591
0.5829	Remote Similarity	NPC212214
0.5825	Remote Similarity	NPC158129
0.5816	Remote Similarity	NPC24594
0.5816	Remote Similarity	NPC472122
0.5814	Remote Similarity	NPC320968
0.5814	Remote Similarity	NPC319766
0.5814	Remote Similarity	NPC151779
0.5801	Remote Similarity	NPC88121
0.5801	Remote Similarity	NPC322878
0.5801	Remote Similarity	NPC471680
0.5798	Remote Similarity	NPC21126
0.5795	Remote Similarity	NPC34508
0.5794	Remote Similarity	NPC107077
0.5794	Remote Similarity	NPC223791
0.5792	Remote Similarity	NPC105717
0.5787	Remote Similarity	NPC248454
0.5784	Remote Similarity	NPC37548
0.5784	Remote Similarity	NPC243716
0.5783	Remote Similarity	NPC478029
0.5769	Remote Similarity	NPC314358
0.5766	Remote Similarity	NPC253987
0.5765	Remote Similarity	NPC6975
0.5765	Remote Similarity	NPC473704
0.5759	Remote Similarity	NPC194390
0.5759	Remote Similarity	NPC224610
0.5759	Remote Similarity	NPC88267
0.5759	Remote Similarity	NPC113326
0.5758	Remote Similarity	NPC133261
0.5758	Remote Similarity	NPC270009
0.5753	Remote Similarity	NPC262166
0.5738	Remote Similarity	NPC128237
0.5738	Remote Similarity	NPC83790
0.5729	Remote Similarity	NPC472105
0.5729	Remote Similarity	NPC476118
0.5729	Remote Similarity	NPC187827
0.5722	Remote Similarity	NPC34319
0.5721	Remote Similarity	NPC216221
0.5714	Remote Similarity	NPC134480
0.5714	Remote Similarity	NPC314603
0.5714	Remote Similarity	NPC19170
0.5714	Remote Similarity	NPC316008
0.5714	Remote Similarity	NPC313867
0.5714	Remote Similarity	NPC75634
0.5707	Remote Similarity	NPC56058
0.5707	Remote Similarity	NPC522
0.5702	Remote Similarity	NPC477516
0.5701	Remote Similarity	NPC315804
0.5701	Remote Similarity	NPC313804
0.57	Remote Similarity	NPC314394
0.5699	Remote Similarity	NPC187951
0.5686	Remote Similarity	NPC46413
0.5686	Remote Similarity	NPC213629
0.5684	Remote Similarity	NPC469898
0.5683	Remote Similarity	NPC262077

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 NPC476103 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	568
0.2-0.3	968
0.3-0.4	2278
0.4-0.5	4137
0.5-0.6	1003
0.6-0.7	54
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
0.7598	Intermediate Similarity	NPD7977	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8071	Approved
0.7282	Intermediate Similarity	NPD8260	Approved
0.7196	Intermediate Similarity	NPD8339	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6632	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5634	Approved
0.6632	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7806	Phase 2
0.658	Remote Similarity	NPD6349	Phase 1
0.6495	Remote Similarity	NPD2015	Discontinued
0.6465	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1745	Approved
0.64	Remote Similarity	NPD3469	Phase 3
0.6374	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6915	Approved
0.6349	Remote Similarity	NPD924	Discontinued
0.6345	Remote Similarity	NPD4949	Discontinued
0.6343	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6092	Discontinued
0.6313	Remote Similarity	NPD3575	Approved
0.6313	Remote Similarity	NPD3576	Approved
0.6281	Remote Similarity	NPD2717	Phase 2
0.6271	Remote Similarity	NPD5503	Approved
0.6271	Remote Similarity	NPD5502	Approved
0.6242	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4856	Approved
0.6239	Remote Similarity	NPD4855	Phase 1
0.6238	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5191	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4742	Phase 3
0.622	Remote Similarity	NPD4741	Phase 3
0.6214	Remote Similarity	NPD8272	Phase 2
0.6207	Remote Similarity	NPD5828	Phase 2
0.6198	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD3015	Discontinued
0.6195	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.618	Remote Similarity	NPD649	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD3759	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD1004	Phase 2
0.6167	Remote Similarity	NPD1005	Phase 2
0.6166	Remote Similarity	NPD2957	Phase 2
0.6165	Remote Similarity	NPD6888	Discontinued
0.6162	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD647	Approved
0.6134	Remote Similarity	NPD8284	Discontinued
0.6126	Remote Similarity	NPD4928	Approved
0.6126	Remote Similarity	NPD4930	Approved
0.6126	Remote Similarity	NPD4929	Approved
0.6105	Remote Similarity	NPD4650	Approved
0.6089	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6079	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7496	Phase 2
0.607	Remote Similarity	NPD7127	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD7104	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD7711	Discontinued
0.6043	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.602	Remote Similarity	NPD8408	Discontinued
0.6012	Remote Similarity	NPD3907	Clinical (unspecified phase)
0.601	Remote Similarity	NPD5439	Approved
0.601	Remote Similarity	NPD5438	Approved
0.6	Remote Similarity	NPD4509	Discontinued
0.6	Remote Similarity	NPD1597	Phase 1
0.5976	Remote Similarity	NPD6360	Discontinued
0.5972	Remote Similarity	NPD7981	Discontinued
0.5969	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD1218	Approved
0.5951	Remote Similarity	NPD1219	Approved
0.5928	Remote Similarity	NPD1260	Approved
0.5924	Remote Similarity	NPD6907	Phase 2
0.5907	Remote Similarity	NPD754	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD2389	Approved
0.5891	Remote Similarity	NPD8063	Discontinued
0.5888	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD6308	Phase 1
0.588	Remote Similarity	NPD6205	Discontinued
0.5873	Remote Similarity	NPD7738	Approved
0.5873	Remote Similarity	NPD7737	Approved
0.5858	Remote Similarity	NPD4273	Approved
0.5857	Remote Similarity	NPD8072	Approved
0.5857	Remote Similarity	NPD6324	Phase 1
0.5856	Remote Similarity	NPD3525	Discontinued
0.5849	Remote Similarity	NPD7834	Approved
0.5849	Remote Similarity	NPD8322	Phase 2
0.5842	Remote Similarity	NPD3487	Phase 1
0.5841	Remote Similarity	NPD3843	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD6819	Phase 2
0.5837	Remote Similarity	NPD5435	Phase 1
0.5829	Remote Similarity	NPD5596	Phase 2
0.5829	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD3328	Phase 2
0.5806	Remote Similarity	NPD5663	Discontinued
0.5799	Remote Similarity	NPD6121	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6910	Phase 3
0.5797	Remote Similarity	NPD7021	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD5323	Approved
0.5792	Remote Similarity	NPD6381	Phase 2
0.5792	Remote Similarity	NPD2749	Discontinued
0.5789	Remote Similarity	NPD5367	Discontinued
0.5787	Remote Similarity	NPD8122	Approved
0.5787	Remote Similarity	NPD8123	Approved
0.5787	Remote Similarity	NPD5452	Phase 2
0.5785	Remote Similarity	NPD5461	Discontinued
0.5782	Remote Similarity	NPD6139	Clinical (unspecified phase)
0.5779	Remote Similarity	NPD2852	Approved
0.5777	Remote Similarity	NPD7944	Discontinued
0.5775	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD3279	Phase 2
0.5769	Remote Similarity	NPD4470	Phase 2
0.5766	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7469	Discontinued
0.5761	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD5523	Approved
0.5753	Remote Similarity	NPD5524	Approved
0.5751	Remote Similarity	NPD7133	Discontinued
0.575	Remote Similarity	NPD5106	Approved
0.575	Remote Similarity	NPD5105	Approved
0.5749	Remote Similarity	NPD6347	Phase 2
0.574	Remote Similarity	NPD5094	Approved
0.5735	Remote Similarity	NPD8073	Approved
0.573	Remote Similarity	NPD740	Clinical (unspecified phase)
0.573	Remote Similarity	NPD1661	Suspended
0.5729	Remote Similarity	NPD5140	Approved
0.5729	Remote Similarity	NPD5898	Approved
0.5729	Remote Similarity	NPD5897	Approved
0.5729	Remote Similarity	NPD5899	Approved
0.5729	Remote Similarity	NPD6595	Phase 3
0.5729	Remote Similarity	NPD5138	Approved
0.5722	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD2306	Approved
0.5721	Remote Similarity	NPD7399	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5020	Approved
0.5714	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6911	Discontinued
0.5708	Remote Similarity	NPD5144	Discontinued
0.5707	Remote Similarity	NPD954	Phase 1
0.5693	Remote Similarity	NPD3082	Discontinued
0.5691	Remote Similarity	NPD1957	Clinical (unspecified phase)
0.569	Remote Similarity	NPD2893	Phase 3
0.5688	Remote Similarity	NPD4331	Approved
0.5686	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD7884	Discontinued
0.5682	Remote Similarity	NPD5299	Approved
0.568	Remote Similarity	NPD3288	Approved
0.568	Remote Similarity	NPD7779	Clinical (unspecified phase)
0.5675	Remote Similarity	NPD8107	Approved
0.5674	Remote Similarity	NPD7895	Discontinued
0.5668	Remote Similarity	NPD3835	Phase 3
0.5668	Remote Similarity	NPD3223	Clinical (unspecified phase)
0.5668	Remote Similarity	NPD3833	Phase 3
0.5663	Remote Similarity	NPD2123	Phase 3
0.5662	Remote Similarity	NPD3848	Phase 2
0.5661	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5023	Discontinued
0.566	Remote Similarity	NPD5047	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD8108	Approved
0.5657	Remote Similarity	NPD4125	Approved
0.5654	Remote Similarity	NPD4557	Approved
0.5654	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.5654	Remote Similarity	NPD2849	Clinical (unspecified phase)
0.5654	Remote Similarity	NPD5255	Approved
0.5648	Remote Similarity	NPD8129	Discovery
0.5647	Remote Similarity	NPD9579	Approved
0.5646	Remote Similarity	NPD6224	Clinical (unspecified phase)
0.5646	Remote Similarity	NPD7490	Discontinued
0.5645	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5021	Discontinued
0.5641	Remote Similarity	NPD4640	Approved
0.5641	Remote Similarity	NPD7770	Phase 3
0.5641	Remote Similarity	NPD4638	Approved
0.5641	Remote Similarity	NPD4639	Approved
0.5638	Remote Similarity	NPD2882	Phase 1
0.5637	Remote Similarity	NPD8021	Approved
0.5637	Remote Similarity	NPD8020	Approved
0.5637	Remote Similarity	NPD2383	Phase 1
0.5637	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD714	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD4415	Approved
0.5622	Remote Similarity	NPD7242	Phase 3
0.5622	Remote Similarity	NPD7241	Phase 3
0.5619	Remote Similarity	NPD7778	Approved
0.5619	Remote Similarity	NPD53	Approved
0.5619	Remote Similarity	NPD7777	Approved
0.5619	Remote Similarity	NPD8075	Discontinued
0.5619	Remote Similarity	NPD2718	Clinical (unspecified phase)
0.5613	Remote Similarity	NPD1881	Approved
0.5611	Remote Similarity	NPD1976	Approved
0.561	Remote Similarity	NPD4991	Discontinued
0.561	Remote Similarity	NPD2856	Approved
0.561	Remote Similarity	NPD2855	Approved
0.561	Remote Similarity	NPD2854	Approved
0.5608	Remote Similarity	NPD7928	Approved
0.5608	Remote Similarity	NPD7929	Approved
0.5607	Remote Similarity	NPD8169	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