NPASS Compound

Structure

NPC472536 OpenBabel07101718312D 58 58 0 0 1 0 0 0 0 0999 V2000 2.9940 -1.3262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6455 5.7365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2776 -0.7425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8522 -1.7264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5495 9.0020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1690 8.3878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4562 8.3878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1633 9.0020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9551 6.8055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4456 0.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2020 5.8063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2020 1.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7359 -1.6967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5045 3.4138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9769 -1.6967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2098 6.8277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0455 -1.6429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7600 5.2718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2970 -0.9798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6712 4.4065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7917 3.4138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3840 2.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2809 -0.8230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1819 8.2274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5309 8.2274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9148 5.8063 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4970 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3166 5.3416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3166 1.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8564 -0.7040 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6712 2.4211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0294 1.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7128 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8273 7.2924 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0294 5.3416 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8855 7.2924 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7485 0.6631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8564 7.5317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8273 -0.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7128 6.8277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3840 4.4065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7485 6.1645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8855 -0.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4613 0.6631 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8564 7.5317 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5045 3.4138 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8564 -0.7040 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.4613 6.1645 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6421 2.1818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9148 1.0214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7359 8.5244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1819 -1.3997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2809 7.6506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3549 4.6459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4970 6.8277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5309 -1.3997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.8277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 25 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 14 46 1 0 0 0 0 15 47 1 0 0 0 0 16 48 1 0 0 0 0 17 19 1 0 0 0 0 18 26 1 0 0 0 0 19 27 2 0 0 0 0 20 21 1 0 0 0 0 20 28 2 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 22 46 1 0 0 0 0 26 9 1 1 0 0 0 28 42 1 0 0 0 0 29 12 1 6 0 0 0 29 31 1 0 0 0 0 29 37 1 0 0 0 0 30 13 1 6 0 0 0 30 43 1 0 0 0 0 30 47 1 0 0 0 0 31 49 1 6 0 0 0 32 44 2 3 0 0 0 32 50 1 0 0 0 0 33 23 1 6 0 0 0 33 39 1 0 0 0 0 33 44 1 0 0 0 0 34 24 1 6 0 0 0 34 40 1 0 0 0 0 34 45 1 0 0 0 0 35 26 1 6 0 0 0 35 41 1 0 0 0 0 35 48 1 0 0 0 0 36 25 1 1 0 0 0 36 38 1 0 0 0 0 36 57 1 0 0 0 0 37 27 1 1 0 0 0 37 58 1 0 0 0 0 38 45 2 3 0 0 0 38 51 1 0 0 0 0 39 47 1 0 0 0 0 39 52 2 0 0 0 0 40 48 1 0 0 0 0 40 53 2 0 0 0 0 41 46 1 0 0 0 0 41 54 2 0 0 0 0 42 55 2 0 0 0 0 42 57 1 0 0 0 0 43 56 2 0 0 0 0 43 58 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	819.54
Volume:	862.885
LogP:	4.623
LogD:	3.745
LogS:	-4.306
# Rotatable Bonds:	7
TPSA:	191.96
# H-Bond Aceptor:	15
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	6.057
Fsp3:	0.744
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.103
MDCK Permeability:	1.902085932670161e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.868
20% Bioavailability (F20%):	0.674
30% Bioavailability (F30%):	0.936

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	83.21570587158203%
Volume Distribution (VD):	0.591
Pgp-substrate:	4.673676490783691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.145
CYP2C19-substrate:	0.758
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.882

ADMET: Excretion

Clearance (CL):	9.132
Half-life (T1/2):	0.288

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.123
Skin Sensitization:	0.038
Carcinogencity:	0.006
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC472536

Natural Product ID:	NPC472536
*Common Name:**	Aurilide C
IUPAC Name:	(3S,6S,12S,15S,18R,21E,24S,25S,26S)-12-[(2R)-butan-2-yl]-24-hydroxy-3,4,10,13,21,25-hexamethyl-26-[(E)-pent-2-en-2-yl]-6,15,18-tri(propan-2-yl)-1,19-dioxa-4,7,10,13,16-pentazacyclohexacos-21-ene-2,5,8,11,14,17,20-heptone
Synonyms:	Aurilide C
Standard InCHIKey:	BCIDYWRVGQFMIS-NOZRKBPESA-N
Standard InCHI:	InChI=1S/C43H73N5O10/c1-17-19-27(10)37-29(12)31(49)21-20-28(11)42(55)57-36(25(7)8)38(51)45-34(24(5)6)40(53)48(16)35(26(9)18-2)41(54)46(14)22-32(50)44-33(23(3)4)39(52)47(15)30(13)43(56)58-37/h19-20,23-26,29-31,33-37,49H,17-18,21-22H2,1-16H3,(H,44,50)(H,45,51)/b27-19+,28-20+/t26-,29+,30+,31+,33+,34+,35+,36-,37-/m1/s1
SMILES:	CC/C=C(/[C@H]1OC(=O)[C@H](C)N(C)C(=O)[C@@H](N=C(O)CN(C)C(=O)[C@H]([C@@H](CC)C)N(C(=O)[C@@H](N=C([C@H](OC(=O)/C(=C/C[C@@H]([C@@H]1C)O)/C)C(C)C)O)C(C)C)C)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL354961
PubChem CID:	11585931
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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]
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]
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]
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]
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]
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
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	LC50	=	130.0	nM	PMID[454041]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	50.0	nM	PMID[454041]

☑ 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 NPC472536 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	87
0.1-0.2	635
0.2-0.3	9083
0.3-0.4	21871
0.4-0.5	8581
0.5-0.6	2102
0.6-0.7	306
0.7-0.8	29
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC103391
0.7895	Intermediate Similarity	NPC201244
0.7895	Intermediate Similarity	NPC477217
0.7788	Intermediate Similarity	NPC205176
0.7778	Intermediate Similarity	NPC135121
0.7642	Intermediate Similarity	NPC273185
0.7586	Intermediate Similarity	NPC171734
0.7436	Intermediate Similarity	NPC474099
0.7387	Intermediate Similarity	NPC469739
0.7304	Intermediate Similarity	NPC474244
0.725	Intermediate Similarity	NPC476875
0.7176	Intermediate Similarity	NPC120335
0.7167	Intermediate Similarity	NPC251122
0.7155	Intermediate Similarity	NPC475149
0.7155	Intermediate Similarity	NPC471097
0.7143	Intermediate Similarity	NPC207820
0.7143	Intermediate Similarity	NPC315188
0.7094	Intermediate Similarity	NPC68001
0.7094	Intermediate Similarity	NPC474827
0.7094	Intermediate Similarity	NPC199831
0.7094	Intermediate Similarity	NPC474828
0.7069	Intermediate Similarity	NPC188785
0.7059	Intermediate Similarity	NPC127741
0.7054	Intermediate Similarity	NPC309525
0.7	Intermediate Similarity	NPC473249
0.6983	Remote Similarity	NPC13175
0.6983	Remote Similarity	NPC475791
0.6975	Remote Similarity	NPC154601
0.6957	Remote Similarity	NPC52820
0.6957	Remote Similarity	NPC307357
0.6957	Remote Similarity	NPC46098
0.6957	Remote Similarity	NPC268841
0.6949	Remote Similarity	NPC476877
0.6934	Remote Similarity	NPC68865
0.6897	Remote Similarity	NPC475758
0.6897	Remote Similarity	NPC220234
0.6885	Remote Similarity	NPC469603
0.6838	Remote Similarity	NPC26597
0.6833	Remote Similarity	NPC476876
0.6833	Remote Similarity	NPC271269
0.6777	Remote Similarity	NPC251330
0.6763	Remote Similarity	NPC315848
0.6763	Remote Similarity	NPC315210
0.6754	Remote Similarity	NPC38172
0.675	Remote Similarity	NPC469604
0.675	Remote Similarity	NPC74035
0.6724	Remote Similarity	NPC175614
0.6723	Remote Similarity	NPC5864
0.6723	Remote Similarity	NPC124554
0.6723	Remote Similarity	NPC301148
0.672	Remote Similarity	NPC469597
0.6691	Remote Similarity	NPC120420
0.6667	Remote Similarity	NPC168113
0.6667	Remote Similarity	NPC470652
0.6667	Remote Similarity	NPC246005
0.6642	Remote Similarity	NPC246079
0.6642	Remote Similarity	NPC99864
0.6641	Remote Similarity	NPC201889
0.6641	Remote Similarity	NPC106791
0.6641	Remote Similarity	NPC235625
0.6638	Remote Similarity	NPC189764
0.662	Remote Similarity	NPC176226
0.662	Remote Similarity	NPC197682
0.6612	Remote Similarity	NPC64168
0.6612	Remote Similarity	NPC124549
0.6596	Remote Similarity	NPC239762
0.6596	Remote Similarity	NPC163392
0.6591	Remote Similarity	NPC470654
0.6591	Remote Similarity	NPC470653
0.6591	Remote Similarity	NPC470650
0.6589	Remote Similarity	NPC477237
0.6587	Remote Similarity	NPC130124
0.6587	Remote Similarity	NPC193471
0.6585	Remote Similarity	NPC67009
0.6573	Remote Similarity	NPC52748
0.6567	Remote Similarity	NPC477793
0.6567	Remote Similarity	NPC329919
0.656	Remote Similarity	NPC474411
0.656	Remote Similarity	NPC474431
0.6549	Remote Similarity	NPC155230
0.6529	Remote Similarity	NPC198344
0.6529	Remote Similarity	NPC80439
0.6529	Remote Similarity	NPC6271
0.6529	Remote Similarity	NPC173690
0.6529	Remote Similarity	NPC279833
0.6522	Remote Similarity	NPC62263
0.6522	Remote Similarity	NPC173763
0.6522	Remote Similarity	NPC471098
0.6507	Remote Similarity	NPC471820
0.6507	Remote Similarity	NPC471821
0.6496	Remote Similarity	NPC233273
0.6496	Remote Similarity	NPC205546
0.6496	Remote Similarity	NPC50902
0.6489	Remote Similarity	NPC477238
0.6484	Remote Similarity	NPC296043
0.6483	Remote Similarity	NPC262077
0.648	Remote Similarity	NPC122926
0.648	Remote Similarity	NPC113012
0.6479	Remote Similarity	NPC476259
0.6463	Remote Similarity	NPC2501
0.6457	Remote Similarity	NPC63191
0.6457	Remote Similarity	NPC471202
0.6438	Remote Similarity	NPC145113
0.6435	Remote Similarity	NPC474576
0.6435	Remote Similarity	NPC17143
0.6435	Remote Similarity	NPC47230
0.6434	Remote Similarity	NPC329216
0.6433	Remote Similarity	NPC196091
0.6429	Remote Similarity	NPC29501
0.6429	Remote Similarity	NPC471053
0.6429	Remote Similarity	NPC47857
0.6429	Remote Similarity	NPC181510
0.6429	Remote Similarity	NPC471052
0.6429	Remote Similarity	NPC471051
0.6429	Remote Similarity	NPC168758
0.6429	Remote Similarity	NPC316984
0.6429	Remote Similarity	NPC30911
0.6423	Remote Similarity	NPC201128
0.6417	Remote Similarity	NPC233932
0.6406	Remote Similarity	NPC471645
0.6385	Remote Similarity	NPC239357
0.6385	Remote Similarity	NPC284656
0.6382	Remote Similarity	NPC297145
0.6382	Remote Similarity	NPC197743
0.6378	Remote Similarity	NPC478024
0.6376	Remote Similarity	NPC162104
0.6364	Remote Similarity	NPC160688
0.6364	Remote Similarity	NPC53858
0.6364	Remote Similarity	NPC84128
0.6356	Remote Similarity	NPC150041
0.6348	Remote Similarity	NPC474593
0.6348	Remote Similarity	NPC475801
0.6345	Remote Similarity	NPC476978
0.6343	Remote Similarity	NPC36254
0.6341	Remote Similarity	NPC323720
0.6336	Remote Similarity	NPC471261
0.6333	Remote Similarity	NPC473341
0.6333	Remote Similarity	NPC122590
0.6327	Remote Similarity	NPC329761
0.6327	Remote Similarity	NPC225648
0.6324	Remote Similarity	NPC470651
0.6324	Remote Similarity	NPC470655
0.6308	Remote Similarity	NPC475642
0.6306	Remote Similarity	NPC474312
0.6301	Remote Similarity	NPC5620
0.6299	Remote Similarity	NPC471527
0.6294	Remote Similarity	NPC98424
0.6294	Remote Similarity	NPC476133
0.6294	Remote Similarity	NPC178662
0.6294	Remote Similarity	NPC92784
0.6294	Remote Similarity	NPC470884
0.629	Remote Similarity	NPC475918
0.6286	Remote Similarity	NPC471256
0.6281	Remote Similarity	NPC474985
0.6276	Remote Similarity	NPC139326
0.6276	Remote Similarity	NPC161069
0.627	Remote Similarity	NPC298484
0.6266	Remote Similarity	NPC186617
0.6262	Remote Similarity	NPC476324
0.6262	Remote Similarity	NPC476130
0.6259	Remote Similarity	NPC314358
0.625	Remote Similarity	NPC476241
0.625	Remote Similarity	NPC476260
0.625	Remote Similarity	NPC476344
0.625	Remote Similarity	NPC150967
0.625	Remote Similarity	NPC275100
0.624	Remote Similarity	NPC271562
0.6239	Remote Similarity	NPC472264
0.6234	Remote Similarity	NPC1390
0.6234	Remote Similarity	NPC62104
0.6232	Remote Similarity	NPC319766
0.6231	Remote Similarity	NPC315652
0.6231	Remote Similarity	NPC7905
0.6226	Remote Similarity	NPC471568
0.6226	Remote Similarity	NPC473693
0.6226	Remote Similarity	NPC138435
0.6224	Remote Similarity	NPC471264
0.6224	Remote Similarity	NPC471265
0.6216	Remote Similarity	NPC284456
0.6216	Remote Similarity	NPC6902
0.6216	Remote Similarity	NPC184473
0.6211	Remote Similarity	NPC26108
0.6211	Remote Similarity	NPC473354
0.6207	Remote Similarity	NPC469426
0.6207	Remote Similarity	NPC39290
0.6207	Remote Similarity	NPC469427
0.6207	Remote Similarity	NPC269398
0.6207	Remote Similarity	NPC263493
0.6207	Remote Similarity	NPC159369
0.6204	Remote Similarity	NPC476179
0.6204	Remote Similarity	NPC476125
0.6202	Remote Similarity	NPC5485
0.6202	Remote Similarity	NPC273814
0.62	Remote Similarity	NPC475168
0.62	Remote Similarity	NPC7817
0.6198	Remote Similarity	NPC475440
0.619	Remote Similarity	NPC316008
0.619	Remote Similarity	NPC313867
0.6187	Remote Similarity	NPC316401
0.6184	Remote Similarity	NPC475342

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 NPC472536 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	77
0.1-0.2	369
0.2-0.3	2736
0.3-0.4	4523
0.4-0.5	1243
0.5-0.6	183
0.6-0.7	19
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7	Intermediate Similarity	NPD7746	Phase 1
0.7	Intermediate Similarity	NPD7747	Phase 1
0.6885	Remote Similarity	NPD6421	Discontinued
0.6794	Remote Similarity	NPD8273	Phase 1
0.6642	Remote Similarity	NPD8415	Approved
0.6594	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7623	Phase 3
0.6429	Remote Similarity	NPD2204	Approved
0.6364	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4228	Discovery
0.6299	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8384	Approved
0.6202	Remote Similarity	NPD1376	Discontinued
0.6154	Remote Similarity	NPD6095	Approved
0.6154	Remote Similarity	NPD6094	Approved
0.6148	Remote Similarity	NPD7642	Approved
0.6136	Remote Similarity	NPD7641	Discontinued
0.6129	Remote Similarity	NPD2259	Approved
0.6129	Remote Similarity	NPD2258	Approved
0.6111	Remote Similarity	NPD1452	Discontinued
0.6058	Remote Similarity	NPD4816	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD8451	Approved
0.6039	Remote Similarity	NPD8414	Discontinued
0.6016	Remote Similarity	NPD6413	Approved
0.6014	Remote Similarity	NPD6681	Discovery
0.6014	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD8392	Approved
0.6	Remote Similarity	NPD8390	Approved
0.594	Remote Similarity	NPD7505	Discontinued
0.5917	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD2099	Approved
0.5896	Remote Similarity	NPD1773	Discontinued
0.589	Remote Similarity	NPD8172	Phase 2
0.589	Remote Similarity	NPD8173	Phase 2
0.5882	Remote Similarity	NPD46	Approved
0.5882	Remote Similarity	NPD7838	Discovery
0.5882	Remote Similarity	NPD6698	Approved
0.5874	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.587	Remote Similarity	NPD8341	Approved
0.587	Remote Similarity	NPD8342	Approved
0.587	Remote Similarity	NPD8299	Approved
0.587	Remote Similarity	NPD8340	Approved
0.5862	Remote Similarity	NPD7760	Phase 2
0.5862	Remote Similarity	NPD7759	Phase 2
0.5854	Remote Similarity	NPD8038	Phase 2
0.5827	Remote Similarity	NPD2584	Suspended
0.5822	Remote Similarity	NPD5767	Discontinued
0.5821	Remote Similarity	NPD7500	Approved
0.5821	Remote Similarity	NPD961	Discontinued
0.582	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD2645	Approved
0.5802	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD7830	Approved
0.5797	Remote Similarity	NPD7829	Approved
0.5796	Remote Similarity	NPD8417	Discontinued
0.5789	Remote Similarity	NPD8323	Discontinued
0.5758	Remote Similarity	NPD2090	Approved
0.575	Remote Similarity	NPD4261	Phase 1
0.5746	Remote Similarity	NPD869	Approved
0.5736	Remote Similarity	NPD2147	Approved
0.5735	Remote Similarity	NPD2495	Phase 3
0.5735	Remote Similarity	NPD3159	Discontinued
0.5734	Remote Similarity	NPD3626	Phase 3
0.5726	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD1806	Approved
0.5725	Remote Similarity	NPD1748	Approved
0.5705	Remote Similarity	NPD6077	Discontinued
0.5704	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD2100	Approved
0.5659	Remote Similarity	NPD4211	Phase 1
0.5646	Remote Similarity	NPD8416	Discontinued
0.5625	Remote Similarity	NPD1407	Approved
0.5625	Remote Similarity	NPD6122	Discontinued
0.562	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD8080	Discontinued
0.5606	Remote Similarity	NPD6420	Discontinued
0.5603	Remote Similarity	NPD2148	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