NPASS Compound

Structure

NPC475532 OpenBabel07101719162D 62 65 0 0 1 0 0 0 0 0999 V2000 -6.5555 4.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7710 5.8786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0318 3.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7184 4.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2222 2.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1122 3.2075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4165 1.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3709 0.2354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0268 -1.6178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1965 3.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5007 2.0230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4165 -0.0631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9293 -1.3246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1779 6.7094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3118 8.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4595 5.5448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0439 7.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1779 8.7094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4200 5.0689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1066 -0.4418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6011 -0.7992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4458 6.7094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4749 3.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5816 2.4208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8261 4.8801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9476 2.6358 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3907 3.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3118 7.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4458 5.7094 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0439 8.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 0.6142 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3361 1.4514 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9458 -0.3247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0973 4.3331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6692 2.8264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9889 4.3331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2277 1.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0576 1.6419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9458 -0.3247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3117 5.0689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4732 2.4208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7891 0.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7968 -0.8206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5781 -1.7964 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.7512 -0.5221 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.0610 -0.1433 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4990 3.4174 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7534 3.2281 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4322 5.5448 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8916 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2519 1.0497 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3906 3.4174 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 -4.9099 8.7094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9345 4.8801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7792 1.8325 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1435 1.0497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9734 1.2402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1104 -1.3111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9259 5.8580 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4698 2.3382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5249 -0.0631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 21 1 0 0 0 0 10 27 2 0 0 0 0 11 27 1 0 0 0 0 14 17 1 0 0 0 0 14 28 2 0 0 0 0 15 18 2 0 0 0 0 15 28 1 0 0 0 0 16 19 2 0 0 0 0 16 29 1 0 0 0 0 17 30 2 0 0 0 0 18 30 1 0 0 0 0 19 34 1 0 0 0 0 20 46 1 0 0 0 0 21 53 1 0 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 23 35 1 0 0 0 0 24 32 1 0 0 0 0 24 47 1 0 0 0 0 25 2 1 1 0 0 0 26 3 1 6 0 0 0 26 38 1 0 0 0 0 26 48 1 0 0 0 0 29 22 1 1 0 0 0 29 49 1 0 0 0 0 30 54 1 0 0 0 0 31 12 1 1 0 0 0 31 37 1 0 0 0 0 31 50 1 0 0 0 0 32 42 1 0 0 0 0 32 51 1 6 0 0 0 33 13 1 1 0 0 0 33 39 1 0 0 0 0 33 53 1 0 0 0 0 34 47 2 3 0 0 0 34 55 1 0 0 0 0 35 48 2 3 0 0 0 35 56 1 0 0 0 0 36 25 1 1 0 0 0 36 40 1 0 0 0 0 36 52 1 0 0 0 0 37 41 1 0 0 0 0 37 57 2 0 0 0 0 38 51 2 3 0 0 0 38 58 1 0 0 0 0 39 50 2 3 0 0 0 39 59 1 0 0 0 0 40 49 2 3 0 0 0 40 60 1 0 0 0 0 41 52 1 0 0 0 0 41 61 2 0 0 0 0 42 53 1 0 0 0 0 42 62 2 0 0 0 0 43 44 2 0 0 0 0 43 45 1 0 0 0 0 43 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	858.44
Volume:	864.954
LogP:	0.086
LogD:	0.452
LogS:	-3.085
# Rotatable Bonds:	16
TPSA:	297.6
# H-Bond Aceptor:	19
# H-Bond Donor:	11
# Rings:	4
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	5.794
Fsp3:	0.465
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:	-6.709
MDCK Permeability:	1.9812003301922232e-05
Pgp-inhibitor:	0.05
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.961
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	31.127704620361328%
Volume Distribution (VD):	0.348
Pgp-substrate:	56.84251022338867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.038
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.025

ADMET: Excretion

Clearance (CL):	2.679
Half-life (T1/2):	0.698

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.835
Drug-inuced Liver Injury (DILI):	0.825
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.18
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.183
Carcinogencity:	0.184
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC475532

Natural Product ID:	NPC475532
*Common Name:**	Cyclotheonamide E
IUPAC Name:	(2S)-N-[(3S,7E,9S,12S,16S,19S)-12-[(2R)-butan-2-yl]-16-[3-(diaminomethylideneamino)propyl]-9-[(4-hydroxyphenyl)methyl]-2,6,11,14,15,18-hexaoxo-1,5,10,13,17-pentazabicyclo[17.3.0]docos-7-en-3-yl]-2-[(2-phenylacetyl)amino]propanamide
Synonyms:	Cyclotheonamide E
Standard InCHIKey:	JAVOTTCUBDNFEA-YFQACERUSA-N
Standard InCHI:	InChI=1S/C43H58N10O9/c1-4-25(2)36-40(60)49-29(22-28-14-17-30(54)18-15-28)16-19-34(55)47-24-32(51-38(58)26(3)48-35(56)23-27-10-6-5-7-11-27)42(62)53-21-9-13-33(53)39(59)50-31(37(57)41(61)52-36)12-8-20-46-43(44)45/h5-7,10-11,14-19,25-26,29,31-33,36,54H,4,8-9,12-13,20-24H2,1-3H3,(H,47,55)(H,48,56)(H,49,60)(H,50,59)(H,51,58)(H,52,61)(H4,44,45,46)/b19-16+/t25-,26+,29-,31+,32+,33+,36+/m1/s1
SMILES:	CC[C@H]([C@@H]1NC(=O)C(=O)[C@H](CCCNC(=N)N)N=C(O)[C@@H]2CCCN2C(=O)[C@H](CN=C(/C=C/[C@@H](N=C1O)Cc1ccc(cc1)O)O)N=C([C@@H](N=C(Cc1ccccc1)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507449
PubChem CID:	44584171
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:0004831] Oligopeptides

*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
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277743]
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908961]
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[12608859]
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163586]
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7769397]
NPO32608	ircinia sp.	Species	Irciniidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[7853011]
NPO33174	theonella	Genus	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599274]

☑ 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	6

Activity Type	# Activity
Individual Protein	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	2.9	nM	PMID[561844]
NPT2	Others	Unspecified		IC50	=	30.0	nM	PMID[561844]
NPT2	Others	Unspecified		IC50	=	6.9	nM	PMID[561845]
NPT2	Others	Unspecified		IC50	=	17.0	nM	PMID[561845]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	16.1	nM	PMID[561845]
NPT2	Others	Unspecified		IC50	=	10.6	nM	PMID[561845]

☑ 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 NPC475532 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	254
0.1-0.2	1566
0.2-0.3	10561
0.3-0.4	7325
0.4-0.5	18012
0.5-0.6	4008
0.6-0.7	696
0.7-0.8	202
0.8-0.85	55
0.85-0.9	12
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC165285
0.9806	High Similarity	NPC129486
0.9684	High Similarity	NPC17698
0.913	High Similarity	NPC198254
0.913	High Similarity	NPC274198
0.9012	High Similarity	NPC276506
0.8909	High Similarity	NPC196243
0.8834	High Similarity	NPC280022
0.8696	High Similarity	NPC469243
0.8639	High Similarity	NPC153554
0.859	High Similarity	NPC16188
0.858	High Similarity	NPC475544
0.858	High Similarity	NPC97526
0.858	High Similarity	NPC119652
0.8553	High Similarity	NPC202198
0.8537	High Similarity	NPC223207
0.8491	Intermediate Similarity	NPC233702
0.8485	Intermediate Similarity	NPC290755
0.8485	Intermediate Similarity	NPC304074
0.8485	Intermediate Similarity	NPC471771
0.8457	Intermediate Similarity	NPC61332
0.8457	Intermediate Similarity	NPC240130
0.8447	Intermediate Similarity	NPC473580
0.8434	Intermediate Similarity	NPC328649
0.8415	Intermediate Similarity	NPC241794
0.8387	Intermediate Similarity	NPC476989
0.8373	Intermediate Similarity	NPC61004
0.8372	Intermediate Similarity	NPC473404
0.8343	Intermediate Similarity	NPC94862
0.8323	Intermediate Similarity	NPC56685
0.8323	Intermediate Similarity	NPC261934
0.8323	Intermediate Similarity	NPC5194
0.8314	Intermediate Similarity	NPC170302
0.8314	Intermediate Similarity	NPC475409
0.8314	Intermediate Similarity	NPC475564
0.8313	Intermediate Similarity	NPC63931
0.8239	Intermediate Similarity	NPC311658
0.8214	Intermediate Similarity	NPC141957
0.8212	Intermediate Similarity	NPC302715
0.821	Intermediate Similarity	NPC262166
0.8199	Intermediate Similarity	NPC473491
0.8198	Intermediate Similarity	NPC473546
0.8182	Intermediate Similarity	NPC244336
0.8167	Intermediate Similarity	NPC477638
0.8167	Intermediate Similarity	NPC477632
0.8121	Intermediate Similarity	NPC323336
0.8121	Intermediate Similarity	NPC326349
0.8107	Intermediate Similarity	NPC302597
0.809	Intermediate Similarity	NPC102959
0.8065	Intermediate Similarity	NPC267237
0.8045	Intermediate Similarity	NPC60516
0.8023	Intermediate Similarity	NPC137627
0.8012	Intermediate Similarity	NPC475123
0.8012	Intermediate Similarity	NPC475204
0.8	Intermediate Similarity	NPC244509
0.7977	Intermediate Similarity	NPC26108
0.7975	Intermediate Similarity	NPC48202
0.7953	Intermediate Similarity	NPC66490
0.7944	Intermediate Similarity	NPC477636
0.7933	Intermediate Similarity	NPC96275
0.7923	Intermediate Similarity	NPC329295
0.7919	Intermediate Similarity	NPC306804
0.7911	Intermediate Similarity	NPC313694
0.7911	Intermediate Similarity	NPC242159
0.7907	Intermediate Similarity	NPC46009
0.7892	Intermediate Similarity	NPC476268
0.7874	Intermediate Similarity	NPC471165
0.7862	Intermediate Similarity	NPC214988
0.7857	Intermediate Similarity	NPC477631
0.7845	Intermediate Similarity	NPC51047
0.7841	Intermediate Similarity	NPC269750
0.7841	Intermediate Similarity	NPC194671
0.7826	Intermediate Similarity	NPC477639
0.7771	Intermediate Similarity	NPC136797
0.7771	Intermediate Similarity	NPC279871
0.7759	Intermediate Similarity	NPC89831
0.7742	Intermediate Similarity	NPC477552
0.7742	Intermediate Similarity	NPC477550
0.7727	Intermediate Similarity	NPC50016
0.7714	Intermediate Similarity	NPC273755
0.7701	Intermediate Similarity	NPC40234
0.7692	Intermediate Similarity	NPC246591
0.7688	Intermediate Similarity	NPC107938
0.7688	Intermediate Similarity	NPC294516
0.767	Intermediate Similarity	NPC476227
0.766	Intermediate Similarity	NPC469443
0.766	Intermediate Similarity	NPC477551
0.7657	Intermediate Similarity	NPC230611
0.7654	Intermediate Similarity	NPC168861
0.7647	Intermediate Similarity	NPC287757
0.7647	Intermediate Similarity	NPC319320
0.764	Intermediate Similarity	NPC45037
0.7609	Intermediate Similarity	NPC470728
0.7595	Intermediate Similarity	NPC326966
0.7588	Intermediate Similarity	NPC324850
0.7581	Intermediate Similarity	NPC80514
0.7578	Intermediate Similarity	NPC132636
0.7571	Intermediate Similarity	NPC159767
0.7571	Intermediate Similarity	NPC155506
0.7571	Intermediate Similarity	NPC473402
0.7565	Intermediate Similarity	NPC478005
0.7557	Intermediate Similarity	NPC328494
0.7545	Intermediate Similarity	NPC324081
0.7514	Intermediate Similarity	NPC133470
0.7514	Intermediate Similarity	NPC191863
0.7514	Intermediate Similarity	NPC289776
0.7514	Intermediate Similarity	NPC248670
0.75	Intermediate Similarity	NPC114806
0.7484	Intermediate Similarity	NPC257390
0.7473	Intermediate Similarity	NPC294951
0.7472	Intermediate Similarity	NPC473354
0.7459	Intermediate Similarity	NPC477637
0.7442	Intermediate Similarity	NPC24617
0.7432	Intermediate Similarity	NPC299806
0.7429	Intermediate Similarity	NPC254700
0.7423	Intermediate Similarity	NPC220060
0.7421	Intermediate Similarity	NPC255447
0.7396	Intermediate Similarity	NPC300443
0.7385	Intermediate Similarity	NPC469444
0.7374	Intermediate Similarity	NPC158277
0.7371	Intermediate Similarity	NPC472923
0.7358	Intermediate Similarity	NPC325651
0.7341	Intermediate Similarity	NPC1390
0.7341	Intermediate Similarity	NPC62104
0.7327	Intermediate Similarity	NPC478007
0.7305	Intermediate Similarity	NPC81026
0.7296	Intermediate Similarity	NPC473322
0.7292	Intermediate Similarity	NPC473450
0.729	Intermediate Similarity	NPC71684
0.7289	Intermediate Similarity	NPC326241
0.7288	Intermediate Similarity	NPC209463
0.7283	Intermediate Similarity	NPC471050
0.7283	Intermediate Similarity	NPC471049
0.7283	Intermediate Similarity	NPC471048
0.7282	Intermediate Similarity	NPC323244
0.7273	Intermediate Similarity	NPC163961
0.7273	Intermediate Similarity	NPC469445
0.7273	Intermediate Similarity	NPC473305
0.7268	Intermediate Similarity	NPC476321
0.7267	Intermediate Similarity	NPC469903
0.7255	Intermediate Similarity	NPC478008
0.7246	Intermediate Similarity	NPC266741
0.7245	Intermediate Similarity	NPC194699
0.7245	Intermediate Similarity	NPC219350
0.7243	Intermediate Similarity	NPC138083
0.7243	Intermediate Similarity	NPC235194
0.7228	Intermediate Similarity	NPC471526
0.7225	Intermediate Similarity	NPC328924
0.7213	Intermediate Similarity	NPC32064
0.7209	Intermediate Similarity	NPC473002
0.7209	Intermediate Similarity	NPC39431
0.72	Intermediate Similarity	NPC473003
0.72	Intermediate Similarity	NPC469902
0.7195	Intermediate Similarity	NPC109580
0.7182	Intermediate Similarity	NPC164608
0.7175	Intermediate Similarity	NPC5719
0.7175	Intermediate Similarity	NPC210377
0.7175	Intermediate Similarity	NPC217804
0.7175	Intermediate Similarity	NPC22883
0.7161	Intermediate Similarity	NPC283760
0.716	Intermediate Similarity	NPC119569
0.7158	Intermediate Similarity	NPC475421
0.7151	Intermediate Similarity	NPC122590
0.7151	Intermediate Similarity	NPC186617
0.7143	Intermediate Similarity	NPC81845
0.7135	Intermediate Similarity	NPC475168
0.7135	Intermediate Similarity	NPC15068
0.7135	Intermediate Similarity	NPC7817
0.7117	Intermediate Similarity	NPC244866
0.7115	Intermediate Similarity	NPC200964
0.7111	Intermediate Similarity	NPC471568
0.7111	Intermediate Similarity	NPC473693
0.7101	Intermediate Similarity	NPC473804
0.71	Intermediate Similarity	NPC469442
0.71	Intermediate Similarity	NPC277306
0.7099	Intermediate Similarity	NPC130309
0.7097	Intermediate Similarity	NPC470546
0.7095	Intermediate Similarity	NPC63040
0.7081	Intermediate Similarity	NPC111428
0.7074	Intermediate Similarity	NPC329731
0.7068	Intermediate Similarity	NPC328763
0.7059	Intermediate Similarity	NPC315542
0.7056	Intermediate Similarity	NPC315388
0.7053	Intermediate Similarity	NPC248822
0.705	Intermediate Similarity	NPC295795
0.7043	Intermediate Similarity	NPC470112
0.7043	Intermediate Similarity	NPC470903
0.7043	Intermediate Similarity	NPC167763
0.7041	Intermediate Similarity	NPC316008
0.7041	Intermediate Similarity	NPC313867
0.7041	Intermediate Similarity	NPC209509
0.7037	Intermediate Similarity	NPC234069
0.7037	Intermediate Similarity	NPC200589
0.7032	Intermediate Similarity	NPC470545
0.7031	Intermediate Similarity	NPC59827
0.7031	Intermediate Similarity	NPC184933
0.703	Intermediate Similarity	NPC25539
0.703	Intermediate Similarity	NPC314835
0.7021	Intermediate Similarity	NPC276120
0.7018	Intermediate Similarity	NPC9373

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 NPC475532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	424
0.2-0.3	731
0.3-0.4	1389
0.4-0.5	3699
0.5-0.6	2413
0.6-0.7	301
0.7-0.8	33
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9062	High Similarity	NPD8303	Discontinued
0.8249	Intermediate Similarity	NPD7617	Discontinued
0.821	Intermediate Similarity	NPD7523	Phase 3
0.8182	Intermediate Similarity	NPD7495	Discontinued
0.8182	Intermediate Similarity	NPD8019	Approved
0.8121	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD8076	Discontinued
0.773	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7303	Discontinued
0.7605	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7450	Phase 2
0.7531	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4652	Approved
0.7471	Intermediate Similarity	NPD2098	Approved
0.7469	Intermediate Similarity	NPD6901	Phase 3
0.7452	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2097	Approved
0.7345	Intermediate Similarity	NPD7485	Phase 3
0.7345	Intermediate Similarity	NPD7484	Phase 3
0.7267	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1330	Phase 2
0.7263	Intermediate Similarity	NPD5137	Approved
0.7251	Intermediate Similarity	NPD7131	Phase 3
0.7239	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8292	Phase 2
0.7143	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3136	Phase 2
0.7093	Intermediate Similarity	NPD7613	Discontinued
0.7083	Intermediate Similarity	NPD6681	Discovery
0.7059	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2890	Approved
0.7056	Intermediate Similarity	NPD2888	Approved
0.7056	Intermediate Similarity	NPD2017	Approved
0.7056	Intermediate Similarity	NPD2889	Approved
0.7041	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7978	Discontinued
0.7019	Intermediate Similarity	NPD7451	Discontinued
0.6977	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6188	Approved
0.6946	Remote Similarity	NPD6189	Approved
0.6933	Remote Similarity	NPD5263	Approved
0.6909	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6255	Approved
0.6904	Remote Similarity	NPD6256	Approved
0.6904	Remote Similarity	NPD6254	Approved
0.6897	Remote Similarity	NPD6187	Approved
0.6893	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3072	Approved
0.6875	Remote Similarity	NPD3073	Approved
0.6875	Remote Similarity	NPD3071	Approved
0.6872	Remote Similarity	NPD5967	Approved
0.6853	Remote Similarity	NPD6253	Approved
0.6831	Remote Similarity	NPD7608	Discontinued
0.6813	Remote Similarity	NPD4762	Approved
0.6813	Remote Similarity	NPD4761	Approved
0.6805	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8031	Discontinued
0.6789	Remote Similarity	NPD6557	Phase 2
0.6788	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8173	Phase 2
0.6786	Remote Similarity	NPD8172	Phase 2
0.6786	Remote Similarity	NPD6073	Approved
0.6782	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2562	Approved
0.677	Remote Similarity	NPD2561	Approved
0.6768	Remote Similarity	NPD3040	Approved
0.6755	Remote Similarity	NPD5445	Approved
0.6755	Remote Similarity	NPD6297	Approved
0.6746	Remote Similarity	NPD3552	Approved
0.6746	Remote Similarity	NPD3554	Approved
0.6746	Remote Similarity	NPD3553	Approved
0.6746	Remote Similarity	NPD3555	Approved
0.6727	Remote Similarity	NPD4676	Approved
0.6726	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3908	Approved
0.6726	Remote Similarity	NPD8643	Discontinued
0.6719	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6853	Approved
0.6702	Remote Similarity	NPD6851	Approved
0.6687	Remote Similarity	NPD3125	Approved
0.6667	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4177	Approved
0.6667	Remote Similarity	NPD4175	Approved
0.6648	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2874	Phase 2
0.6646	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3055	Approved
0.6646	Remote Similarity	NPD3053	Approved
0.6629	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7720	Phase 2
0.6625	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8162	Phase 2
0.6617	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1968	Approved
0.6609	Remote Similarity	NPD1967	Approved
0.6605	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8025	Phase 2
0.6597	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5614	Approved
0.6591	Remote Similarity	NPD5613	Approved
0.6591	Remote Similarity	NPD6088	Approved
0.6588	Remote Similarity	NPD5725	Approved
0.6588	Remote Similarity	NPD2568	Approved
0.6585	Remote Similarity	NPD5310	Approved
0.6585	Remote Similarity	NPD5311	Approved
0.6584	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD4153	Approved
0.6568	Remote Similarity	NPD6346	Approved
0.6568	Remote Similarity	NPD5323	Approved
0.6562	Remote Similarity	NPD7280	Phase 3
0.6562	Remote Similarity	NPD7281	Phase 3
0.6557	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6796	Discontinued
0.6554	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2458	Approved
0.6552	Remote Similarity	NPD2209	Approved
0.6552	Remote Similarity	NPD2211	Approved
0.6552	Remote Similarity	NPD2460	Phase 3
0.6552	Remote Similarity	NPD2459	Approved
0.6545	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD9568	Approved
0.6536	Remote Similarity	NPD8315	Phase 1
0.6533	Remote Similarity	NPD7282	Approved
0.6532	Remote Similarity	NPD2087	Approved
0.6532	Remote Similarity	NPD2088	Approved
0.6528	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5485	Approved
0.6526	Remote Similarity	NPD5484	Approved
0.6524	Remote Similarity	NPD4677	Discontinued
0.6519	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6676	Phase 2
0.6514	Remote Similarity	NPD5481	Discontinued
0.6513	Remote Similarity	NPD4157	Discontinued
0.6509	Remote Similarity	NPD7086	Phase 2
0.6497	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3987	Approved
0.6497	Remote Similarity	NPD3988	Approved
0.6491	Remote Similarity	NPD5314	Approved
0.6484	Remote Similarity	NPD7011	Discontinued
0.6482	Remote Similarity	NPD3659	Discontinued
0.648	Remote Similarity	NPD6836	Approved
0.6471	Remote Similarity	NPD8416	Discontinued
0.6468	Remote Similarity	NPD7811	Phase 3
0.6468	Remote Similarity	NPD7810	Phase 3
0.6462	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5304	Approved
0.646	Remote Similarity	NPD5303	Approved
0.6453	Remote Similarity	NPD6852	Discontinued
0.645	Remote Similarity	NPD5299	Approved
0.645	Remote Similarity	NPD5581	Approved
0.6448	Remote Similarity	NPD4566	Approved
0.6448	Remote Similarity	NPD4567	Approved
0.6441	Remote Similarity	NPD7554	Discontinued
0.6429	Remote Similarity	NPD6835	Approved
0.6429	Remote Similarity	NPD2469	Approved
0.6429	Remote Similarity	NPD2468	Approved
0.6429	Remote Similarity	NPD4125	Approved
0.6424	Remote Similarity	NPD4659	Approved
0.6417	Remote Similarity	NPD3286	Discontinued
0.6414	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD5747	Discontinued
0.641	Remote Similarity	NPD6967	Phase 2
0.6407	Remote Similarity	NPD3588	Discontinued
0.6398	Remote Similarity	NPD856	Approved
0.6398	Remote Similarity	NPD16	Approved
0.6398	Remote Similarity	NPD317	Approved
0.6398	Remote Similarity	NPD318	Approved
0.6396	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD8323	Discontinued
0.638	Remote Similarity	NPD7342	Discontinued
0.6377	Remote Similarity	NPD6376	Discontinued
0.6374	Remote Similarity	NPD3062	Approved
0.6374	Remote Similarity	NPD6623	Phase 3
0.6374	Remote Similarity	NPD3061	Approved
0.6374	Remote Similarity	NPD3059	Approved
0.6369	Remote Similarity	NPD6419	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