NPASS Compound

Structure

NPC257511 OpenBabel07101719142D 49 51 0 0 1 0 0 0 0 0999 V2000 -3.0504 4.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5145 0.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6485 -0.8720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3184 3.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3805 6.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3805 5.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5145 1.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0504 0.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3805 8.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7107 4.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0504 3.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6303 3.3305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1303 2.4644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2466 4.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1126 3.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1126 5.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9786 3.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3478 3.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7825 0.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6485 6.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3805 3.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6485 0.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1844 3.1280 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5145 6.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2466 3.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9786 4.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 1.7213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7825 1.6280 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5145 3.6280 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6485 5.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1844 2.1280 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6485 3.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9164 2.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3184 1.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5145 4.6280 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6485 2.1280 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0504 1.6280 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4523 2.1280 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7825 4.6280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7825 3.6280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9164 3.1280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3184 0.6280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5145 7.6280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8446 5.1280 0.0000 O 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 11 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 39 1 0 0 0 0 7 40 1 0 0 0 0 8 41 1 0 0 0 0 9 47 1 0 0 0 0 10 48 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 27 2 0 0 0 0 15 17 2 0 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 17 28 1 0 0 0 0 18 20 2 0 0 0 0 18 38 1 0 0 0 0 19 42 1 0 0 0 0 20 49 1 0 0 0 0 21 24 1 0 0 0 0 22 26 2 0 0 0 0 22 32 1 0 0 0 0 23 27 1 0 0 0 0 25 4 1 6 0 0 0 25 33 1 0 0 0 0 26 47 1 0 0 0 0 28 48 1 0 0 0 0 29 34 1 1 0 0 0 29 42 1 0 0 0 0 30 21 1 6 0 0 0 30 36 1 0 0 0 0 30 40 1 0 0 0 0 31 23 1 6 0 0 0 31 35 1 0 0 0 0 31 39 1 0 0 0 0 32 39 1 0 0 0 0 32 43 2 0 0 0 0 33 37 1 1 0 0 0 33 41 1 0 0 0 0 34 38 2 0 0 0 0 34 49 1 0 0 0 0 35 40 1 0 0 0 0 35 44 2 0 0 0 0 36 41 1 0 0 0 0 36 45 2 0 0 0 0 37 42 1 0 0 0 0 37 46 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	697.39
Volume:	722.708
LogP:	4.247
LogD:	3.981
LogS:	-4.892
# Rotatable Bonds:	20
TPSA:	112.59
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	4.594
Fsp3:	0.595
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:	-4.775
MDCK Permeability:	4.2395087803015485e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.082
Human Intestinal Absorption (HIA):	0.181
20% Bioavailability (F20%):	0.37
30% Bioavailability (F30%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	92.57170867919922%
Volume Distribution (VD):	0.678
Pgp-substrate:	5.857725620269775%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.238
CYP2C19-inhibitor:	0.784
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.901
CYP2C9-substrate:	0.198
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.258
CYP3A4-inhibitor:	0.976
CYP3A4-substrate:	0.933

ADMET: Excretion

Clearance (CL):	7.975
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.124
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.539
Maximum Recommended Daily Dose:	0.553
Skin Sensitization:	0.046
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.789

Download Data

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

Natural Product: NPC257511

Natural Product ID:	NPC257511
*Common Name:**	Lyngbyapeptin A
IUPAC Name:	(2S)-2-[[(2S)-2-[[(E)-3-methoxybut-2-enoyl]-methylamino]-3-(4-methoxyphenyl)propanoyl]-methylamino]-N,4-dimethyl-N-[(2S,3S)-3-methyl-1-oxo-1-[(2S)-2-(1,3-thiazol-2-yl)pyrrolidin-1-yl]pentan-2-yl]pentanamide
Synonyms:
Standard InCHIKey:	HTBQLUDZPAANPB-WMQQFFOQSA-N
Standard InCHI:	InChI=1S/C37H55N5O6S/c1-11-25(4)33(37(46)42-19-12-13-29(42)34-38-18-20-49-34)41(8)36(45)30(21-24(2)3)40(7)35(44)31(39(6)32(43)22-26(5)47-9)23-27-14-16-28(48-10)17-15-27/h14-18,20,22,24-25,29-31,33H,11-13,19,21,23H2,1-10H3/b26-22+/t25-,29-,30-,31-,33-/m0/s1
SMILES:	CO/C(=C/C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1CCC[C@H]1c1nccs1)[C@H](CC)C)C)CC(C)C)C)Cc1ccc(cc1)OC)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500478
PubChem CID:	10349747
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:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004321] Phenylalanine and derivatives

*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
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10514329]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10654420]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10691708]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	palauan	n.a.	PMID[10691729]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10843570]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10924172]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10978206]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076571]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076573]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11076574]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11277744]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11389621]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11430000]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473443]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11922791]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Palauan	n.a.	PMID[12141859]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12502348]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762789]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Palauan	n.a.	PMID[12762800]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762816]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[12828459]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575437]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14695793]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1517734]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Papua New Guinea	n.a.	PMID[16643028]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125217]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Florida Everglades	n.a.	PMID[17432902]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17441769]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18444683]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18693761]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Singapore	n.a.	PMID[19093843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19489598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	eastern Caribbean	n.a.	PMID[19739598]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19839606]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20030365]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	panamanian	n.a.	PMID[20158242]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Floridian	n.a.	PMID[20166701]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20936843]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21138309]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2128518]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21341718]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21539315]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Florida Keys	n.a.	PMID[21705224]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21806011]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21999614]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22035372]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29792428]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3924698]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[7623050]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	Caribbean	n.a.	PMID[8699186]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9584405]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599278]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9599279]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9784156]
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	5000.0	nM	PMID[558158]

☑ 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 NPC257511 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	403
0.1-0.2	3071
0.2-0.3	13254
0.3-0.4	6935
0.4-0.5	15823
0.5-0.6	2991
0.6-0.7	206
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9409	High Similarity	NPC75498
0.7865	Intermediate Similarity	NPC161143
0.7828	Intermediate Similarity	NPC106235
0.7828	Intermediate Similarity	NPC239660
0.7681	Intermediate Similarity	NPC14877
0.7681	Intermediate Similarity	NPC475350
0.7681	Intermediate Similarity	NPC145178
0.766	Intermediate Similarity	NPC475920
0.7571	Intermediate Similarity	NPC251036
0.7545	Intermediate Similarity	NPC475196
0.7094	Intermediate Similarity	NPC329731
0.7094	Intermediate Similarity	NPC4910
0.7039	Intermediate Similarity	NPC165538
0.6971	Remote Similarity	NPC184933
0.6971	Remote Similarity	NPC59827
0.6942	Remote Similarity	NPC122427
0.6942	Remote Similarity	NPC329961
0.6912	Remote Similarity	NPC96016
0.6872	Remote Similarity	NPC477527
0.6837	Remote Similarity	NPC472923
0.6827	Remote Similarity	NPC477526
0.6792	Remote Similarity	NPC127085
0.6772	Remote Similarity	NPC189908
0.6718	Remote Similarity	NPC287757
0.6718	Remote Similarity	NPC319320
0.6717	Remote Similarity	NPC254700
0.6711	Remote Similarity	NPC153467
0.6615	Remote Similarity	NPC324081
0.657	Remote Similarity	NPC470112
0.657	Remote Similarity	NPC167763
0.657	Remote Similarity	NPC470903
0.6546	Remote Similarity	NPC202198
0.653	Remote Similarity	NPC210256
0.652	Remote Similarity	NPC168209
0.6502	Remote Similarity	NPC242923
0.6462	Remote Similarity	NPC262166
0.6458	Remote Similarity	NPC16188
0.6435	Remote Similarity	NPC175150
0.6435	Remote Similarity	NPC243633
0.6432	Remote Similarity	NPC305984
0.6425	Remote Similarity	NPC475421
0.6425	Remote Similarity	NPC9373
0.641	Remote Similarity	NPC233702
0.6378	Remote Similarity	NPC261934
0.6378	Remote Similarity	NPC5194
0.6377	Remote Similarity	NPC161242
0.6376	Remote Similarity	NPC315804
0.6376	Remote Similarity	NPC313804
0.6373	Remote Similarity	NPC476103
0.6368	Remote Similarity	NPC194740
0.6355	Remote Similarity	NPC473502
0.6335	Remote Similarity	NPC143325
0.6332	Remote Similarity	NPC303658
0.6329	Remote Similarity	NPC220852
0.6326	Remote Similarity	NPC204970
0.6318	Remote Similarity	NPC241794
0.6316	Remote Similarity	NPC263485
0.6316	Remote Similarity	NPC25316
0.6316	Remote Similarity	NPC229160
0.6304	Remote Similarity	NPC308906
0.6298	Remote Similarity	NPC475534
0.6298	Remote Similarity	NPC476080
0.6294	Remote Similarity	NPC56685
0.6293	Remote Similarity	NPC196091
0.629	Remote Similarity	NPC295898
0.6282	Remote Similarity	NPC319232
0.6282	Remote Similarity	NPC24370
0.628	Remote Similarity	NPC164608
0.6277	Remote Similarity	NPC478253
0.6277	Remote Similarity	NPC478254
0.6275	Remote Similarity	NPC141957
0.6274	Remote Similarity	NPC299806
0.6271	Remote Similarity	NPC326363
0.6268	Remote Similarity	NPC475330
0.6267	Remote Similarity	NPC174758
0.6263	Remote Similarity	NPC307682
0.6261	Remote Similarity	NPC141053
0.6255	Remote Similarity	NPC323244
0.625	Remote Similarity	NPC285343
0.625	Remote Similarity	NPC17305
0.6244	Remote Similarity	NPC24990
0.6244	Remote Similarity	NPC186617
0.6238	Remote Similarity	NPC271792
0.6238	Remote Similarity	NPC174652
0.6233	Remote Similarity	NPC174629
0.6224	Remote Similarity	NPC283783
0.6217	Remote Similarity	NPC12100
0.6214	Remote Similarity	NPC473693
0.6214	Remote Similarity	NPC471568
0.621	Remote Similarity	NPC153400
0.6198	Remote Similarity	NPC476989
0.6195	Remote Similarity	NPC302597
0.6184	Remote Similarity	NPC264176
0.6169	Remote Similarity	NPC323336
0.6169	Remote Similarity	NPC326349
0.6167	Remote Similarity	NPC325976
0.6165	Remote Similarity	NPC315388
0.6161	Remote Similarity	NPC222592
0.6161	Remote Similarity	NPC168486
0.6161	Remote Similarity	NPC32064
0.6157	Remote Similarity	NPC474183
0.6157	Remote Similarity	NPC236668
0.6157	Remote Similarity	NPC101350
0.6151	Remote Similarity	NPC328924
0.6151	Remote Similarity	NPC102593
0.6151	Remote Similarity	NPC196718
0.615	Remote Similarity	NPC287208
0.615	Remote Similarity	NPC82548
0.614	Remote Similarity	NPC238242
0.6137	Remote Similarity	NPC54066
0.613	Remote Similarity	NPC146976
0.613	Remote Similarity	NPC50562
0.6129	Remote Similarity	NPC275393
0.6128	Remote Similarity	NPC122436
0.6125	Remote Similarity	NPC323752
0.6124	Remote Similarity	NPC136797
0.6123	Remote Similarity	NPC174672
0.6121	Remote Similarity	NPC315542
0.6119	Remote Similarity	NPC280638
0.6118	Remote Similarity	NPC186351
0.6116	Remote Similarity	NPC28945
0.6116	Remote Similarity	NPC235685
0.6111	Remote Similarity	NPC473491
0.6109	Remote Similarity	NPC469858
0.6105	Remote Similarity	NPC266425
0.6104	Remote Similarity	NPC274982
0.6104	Remote Similarity	NPC67658
0.6098	Remote Similarity	NPC63931
0.6094	Remote Similarity	NPC314056
0.6094	Remote Similarity	NPC89489
0.6085	Remote Similarity	NPC153554
0.6085	Remote Similarity	NPC478141
0.6077	Remote Similarity	NPC137627
0.607	Remote Similarity	NPC244509
0.6068	Remote Similarity	NPC323969
0.6067	Remote Similarity	NPC315411
0.6065	Remote Similarity	NPC206251
0.6065	Remote Similarity	NPC74382
0.6063	Remote Similarity	NPC41982
0.6059	Remote Similarity	NPC244336
0.6057	Remote Similarity	NPC75179
0.6054	Remote Similarity	NPC478011
0.6049	Remote Similarity	NPC191863
0.6049	Remote Similarity	NPC133470
0.6049	Remote Similarity	NPC184680
0.6049	Remote Similarity	NPC289776
0.6048	Remote Similarity	NPC26108
0.6047	Remote Similarity	NPC295158
0.6047	Remote Similarity	NPC138083
0.6043	Remote Similarity	NPC472098
0.6042	Remote Similarity	NPC138365
0.6035	Remote Similarity	NPC316403
0.6033	Remote Similarity	NPC253675
0.6031	Remote Similarity	NPC314176
0.6027	Remote Similarity	NPC471448
0.6026	Remote Similarity	NPC269270
0.6025	Remote Similarity	NPC470784
0.6025	Remote Similarity	NPC470785
0.6023	Remote Similarity	NPC478013
0.6022	Remote Similarity	NPC315061
0.6019	Remote Similarity	NPC276120
0.601	Remote Similarity	NPC242159
0.601	Remote Similarity	NPC313694
0.6009	Remote Similarity	NPC478005
0.6	Remote Similarity	NPC212850
0.6	Remote Similarity	NPC477586
0.6	Remote Similarity	NPC83289
0.6	Remote Similarity	NPC189724
0.6	Remote Similarity	NPC477588
0.6	Remote Similarity	NPC477585
0.6	Remote Similarity	NPC14686
0.6	Remote Similarity	NPC477590
0.5992	Remote Similarity	NPC316224
0.5991	Remote Similarity	NPC78767
0.5991	Remote Similarity	NPC473814
0.599	Remote Similarity	NPC29650
0.5982	Remote Similarity	NPC117244
0.5982	Remote Similarity	NPC473763
0.5975	Remote Similarity	NPC260434
0.5973	Remote Similarity	NPC475774
0.5973	Remote Similarity	NPC473460
0.5973	Remote Similarity	NPC93390
0.5972	Remote Similarity	NPC279871
0.5963	Remote Similarity	NPC224327
0.5962	Remote Similarity	NPC328649
0.596	Remote Similarity	NPC247298
0.5957	Remote Similarity	NPC470020
0.5951	Remote Similarity	NPC469243
0.595	Remote Similarity	NPC477516
0.5947	Remote Similarity	NPC473422
0.5936	Remote Similarity	NPC64140
0.5936	Remote Similarity	NPC174122
0.5936	Remote Similarity	NPC134079
0.5936	Remote Similarity	NPC29531
0.5936	Remote Similarity	NPC26543
0.5935	Remote Similarity	NPC249662
0.5933	Remote Similarity	NPC129486
0.5932	Remote Similarity	NPC478012
0.5924	Remote Similarity	NPC248670
0.5924	Remote Similarity	NPC475532

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 NPC257511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	618
0.2-0.3	942
0.3-0.4	1423
0.4-0.5	3967
0.5-0.6	1821
0.6-0.7	144
0.7-0.8	2
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
0.7828	Intermediate Similarity	NPD8339	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6627	Discontinued
0.6978	Remote Similarity	NPD7826	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD8284	Discontinued
0.693	Remote Similarity	NPD8071	Approved
0.686	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6349	Phase 1
0.673	Remote Similarity	NPD3395	Approved
0.673	Remote Similarity	NPD3396	Approved
0.6699	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6475	Phase 2
0.6653	Remote Similarity	NPD6205	Discontinued
0.6606	Remote Similarity	NPD2853	Approved
0.6591	Remote Similarity	NPD8260	Approved
0.6588	Remote Similarity	NPD5994	Discontinued
0.6585	Remote Similarity	NPD5485	Approved
0.6585	Remote Similarity	NPD5484	Approved
0.658	Remote Similarity	NPD6390	Discontinued
0.6567	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD8288	Phase 2
0.6546	Remote Similarity	NPD8287	Phase 1
0.654	Remote Similarity	NPD5113	Approved
0.654	Remote Similarity	NPD5114	Approved
0.654	Remote Similarity	NPD5112	Approved
0.6538	Remote Similarity	NPD4850	Phase 1
0.6513	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6504	Approved
0.6509	Remote Similarity	NPD4949	Discontinued
0.6509	Remote Similarity	NPD6505	Approved
0.65	Remote Similarity	NPD7967	Discontinued
0.65	Remote Similarity	NPD5601	Phase 2
0.6498	Remote Similarity	NPD928	Approved
0.6498	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD8479	Phase 2
0.6489	Remote Similarity	NPD6169	Phase 1
0.6476	Remote Similarity	NPD6568	Discontinued
0.6456	Remote Similarity	NPD5920	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7806	Phase 2
0.6446	Remote Similarity	NPD3328	Phase 2
0.6445	Remote Similarity	NPD8108	Approved
0.6429	Remote Similarity	NPD6092	Discontinued
0.6409	Remote Similarity	NPD5513	Phase 2
0.6402	Remote Similarity	NPD3479	Discontinued
0.64	Remote Similarity	NPD2097	Approved
0.6396	Remote Similarity	NPD2885	Approved
0.6396	Remote Similarity	NPD2886	Approved
0.6395	Remote Similarity	NPD8107	Approved
0.639	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6276	Discontinued
0.6378	Remote Similarity	NPD7131	Phase 3
0.6368	Remote Similarity	NPD7467	Discontinued
0.6368	Remote Similarity	NPD2749	Discontinued
0.6364	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.636	Remote Similarity	NPD6825	Phase 1
0.6359	Remote Similarity	NPD1005	Phase 2
0.6359	Remote Similarity	NPD1004	Phase 2
0.6353	Remote Similarity	NPD7681	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.634	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5817	Discontinued
0.6337	Remote Similarity	NPD2098	Approved
0.6333	Remote Similarity	NPD7977	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD4372	Phase 1
0.6324	Remote Similarity	NPD2516	Approved
0.6311	Remote Similarity	NPD4742	Phase 3
0.6311	Remote Similarity	NPD4741	Phase 3
0.6303	Remote Similarity	NPD5107	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4652	Approved
0.6293	Remote Similarity	NPD2517	Approved
0.6288	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD1976	Approved
0.6284	Remote Similarity	NPD4899	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5228	Phase 3
0.6266	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD8016	Phase 3
0.6265	Remote Similarity	NPD8255	Phase 2
0.6261	Remote Similarity	NPD5144	Discontinued
0.6261	Remote Similarity	NPD6324	Phase 1
0.625	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7757	Approved
0.6244	Remote Similarity	NPD7758	Approved
0.624	Remote Similarity	NPD6790	Phase 1
0.6233	Remote Similarity	NPD3397	Phase 2
0.6226	Remote Similarity	NPD7227	Phase 3
0.6226	Remote Similarity	NPD7226	Phase 3
0.6225	Remote Similarity	NPD8246	Approved
0.6225	Remote Similarity	NPD8247	Approved
0.6223	Remote Similarity	NPD8356	Approved
0.6222	Remote Similarity	NPD7403	Phase 1
0.622	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4369	Phase 2
0.6217	Remote Similarity	NPD5524	Approved
0.6217	Remote Similarity	NPD5523	Approved
0.6215	Remote Similarity	NPD4434	Approved
0.6213	Remote Similarity	NPD7711	Discontinued
0.6204	Remote Similarity	NPD8100	Phase 3
0.6199	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7885	Phase 2
0.6198	Remote Similarity	NPD7886	Phase 2
0.6197	Remote Similarity	NPD4889	Approved
0.6195	Remote Similarity	NPD3862	Approved
0.6195	Remote Similarity	NPD3861	Approved
0.619	Remote Similarity	NPD3354	Phase 2
0.6188	Remote Similarity	NPD3802	Phase 3
0.6186	Remote Similarity	NPD8292	Phase 2
0.6186	Remote Similarity	NPD4435	Approved
0.6184	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5452	Phase 2
0.6179	Remote Similarity	NPD6450	Phase 2
0.6175	Remote Similarity	NPD3288	Approved
0.6173	Remote Similarity	NPD4367	Phase 3
0.6173	Remote Similarity	NPD4366	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD5259	Phase 3
0.617	Remote Similarity	NPD7719	Discontinued
0.6169	Remote Similarity	NPD2513	Approved
0.6168	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD2890	Approved
0.6165	Remote Similarity	NPD2889	Approved
0.6165	Remote Similarity	NPD2888	Approved
0.6165	Remote Similarity	NPD2017	Approved
0.6163	Remote Similarity	NPD5047	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7303	Discontinued
0.6161	Remote Similarity	NPD5055	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4887	Discontinued
0.615	Remote Similarity	NPD2052	Approved
0.6147	Remote Similarity	NPD2530	Phase 2
0.6147	Remote Similarity	NPD4989	Phase 2
0.6144	Remote Similarity	NPD5640	Discontinued
0.6143	Remote Similarity	NPD7316	Discontinued
0.614	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6891	Phase 2
0.614	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD2515	Approved
0.6139	Remote Similarity	NPD3007	Approved
0.6134	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD3386	Phase 2
0.6132	Remote Similarity	NPD963	Discontinued
0.6129	Remote Similarity	NPD8101	Phase 3
0.6126	Remote Similarity	NPD6253	Approved
0.6125	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6756	Phase 1
0.6119	Remote Similarity	NPD2053	Approved
0.6119	Remote Similarity	NPD22	Approved
0.6118	Remote Similarity	NPD8430	Approved
0.6114	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5041	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD6254	Approved
0.6099	Remote Similarity	NPD6256	Approved
0.6099	Remote Similarity	NPD6255	Approved
0.6095	Remote Similarity	NPD6044	Discontinued
0.6091	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD4903	Approved
0.6089	Remote Similarity	NPD4905	Approved
0.6089	Remote Similarity	NPD4906	Approved
0.6089	Remote Similarity	NPD6960	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7485	Phase 3
0.6087	Remote Similarity	NPD7484	Phase 3
0.6085	Remote Similarity	NPD2321	Approved
0.6085	Remote Similarity	NPD2601	Approved
0.6085	Remote Similarity	NPD7104	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD2599	Approved
0.6085	Remote Similarity	NPD2600	Approved
0.6083	Remote Similarity	NPD4885	Approved
0.6081	Remote Similarity	NPD8253	Phase 3
0.608	Remote Similarity	NPD5857	Phase 3
0.6078	Remote Similarity	NPD5967	Approved
0.6078	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5461	Discontinued
0.6075	Remote Similarity	NPD7281	Phase 3
0.6075	Remote Similarity	NPD7280	Phase 3
0.6071	Remote Similarity	NPD5481	Discontinued
0.607	Remote Similarity	NPD7470	Discontinued
0.607	Remote Similarity	NPD3878	Approved
0.6064	Remote Similarity	NPD7873	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD4904	Approved
0.6062	Remote Similarity	NPD6551	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7608	Discontinued
0.6056	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7963	Phase 3
0.6054	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD3488	Phase 1
0.6049	Remote Similarity	NPD946	Discontinued
0.6044	Remote Similarity	NPD4044	Discontinued
0.6043	Remote Similarity	NPD4439	Discontinued
0.6043	Remote Similarity	NPD3879	Approved
0.6043	Remote Similarity	NPD4923	Phase 1
0.604	Remote Similarity	NPD2592	Discontinued
0.6037	Remote Similarity	NPD5851	Approved
0.6037	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD5852	Approved
0.6036	Remote Similarity	NPD722	Clinical (unspecified phase)

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