NPASS Compound

Structure

NPC280498 OpenBabel07101719122D 31 32 0 0 1 0 0 0 0 0999 V2000 -8.3978 6.7879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0387 5.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5580 7.2727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7183 6.7879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8785 7.2727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0387 6.7879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 5.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1989 7.2727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6796 5.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3591 6.7879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5193 5.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 5.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 -0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 2.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 2.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3591 5.8182 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6796 -0.9697 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6796 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 4.3636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -0.4848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8398 0.4848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8398 2.4242 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 3.8788 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 -1.9394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 1.9394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.8788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1989 5.3333 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 3 1 0 0 0 0 2 30 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 12 19 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 19 11 1 1 0 0 0 19 30 1 0 0 0 0 20 23 1 0 0 0 0 20 27 1 1 0 0 0 21 24 1 0 0 0 0 21 28 2 0 0 0 0 22 26 2 3 0 0 0 22 29 1 0 0 0 0 23 24 1 1 0 0 0 23 31 1 0 0 0 0 24 18 1 1 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	455.24
Volume:	466.16
LogP:	3.303
LogD:	3.536
LogS:	-4.741
# Rotatable Bonds:	16
TPSA:	88.16
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.219
Synthetic Accessibility Score:	4.57
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.63
MDCK Permeability:	4.0150822314899415e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.937
Human Intestinal Absorption (HIA):	0.197
20% Bioavailability (F20%):	0.769
30% Bioavailability (F30%):	0.508

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.942
Plasma Protein Binding (PPB):	94.19158172607422%
Volume Distribution (VD):	0.389
Pgp-substrate:	3.269357919692993%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.158
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.691
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.627
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	6.659
Half-life (T1/2):	0.759

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.944
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.863
Carcinogencity:	0.882
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.68

Download Data

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

Natural Product: NPC280498

Natural Product ID:	NPC280498
*Common Name:**	8-Epi-Malyngamide C
IUPAC Name:	(E,7S)-N-[(Z)-3-chloro-2-[(1S,2R,6S)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]heptan-6-yl]prop-2-enyl]-7-methoxytetradec-4-enamide
Synonyms:	8-Epi-Malyngamide C
Standard InCHIKey:	WXDBUBIFYCCNLE-FTWIAXFRSA-N
Standard InCHI:	InChI=1S/C24H38ClNO5/c1-3-4-5-6-8-11-19(30-2)12-9-7-10-13-22(29)26-17-18(16-25)24-21(28)15-14-20(27)23(24)31-24/h7,9,16,19-20,23,27H,3-6,8,10-15,17H2,1-2H3,(H,26,29)/b9-7+,18-16-/t19-,20+,23-,24+/m0/s1
SMILES:	CCCCCCC[C@@H](C/C=C/CCC(=NC/C(=C/Cl)/[C@@]12C(=O)CC[C@H]([C@@H]1O2)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079695
PubChem CID:	45379966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	15400.0	nM	PMID[466267]

☑ 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 NPC280498 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	104
0.1-0.2	801
0.2-0.3	3821
0.3-0.4	17127
0.4-0.5	16854
0.5-0.6	3693
0.6-0.7	283
0.7-0.8	12
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8655	High Similarity	NPC323532
0.7634	Intermediate Similarity	NPC121601
0.7634	Intermediate Similarity	NPC471471
0.7634	Intermediate Similarity	NPC164476
0.7426	Intermediate Similarity	NPC472430
0.7413	Intermediate Similarity	NPC475837
0.725	Intermediate Similarity	NPC128501
0.7226	Intermediate Similarity	NPC472428
0.712	Intermediate Similarity	NPC46764
0.7119	Intermediate Similarity	NPC279722
0.7059	Intermediate Similarity	NPC236176
0.696	Remote Similarity	NPC70235
0.687	Remote Similarity	NPC120599
0.687	Remote Similarity	NPC200412
0.687	Remote Similarity	NPC156336
0.6815	Remote Similarity	NPC204639
0.6774	Remote Similarity	NPC215988
0.6772	Remote Similarity	NPC474725
0.6772	Remote Similarity	NPC21324
0.6763	Remote Similarity	NPC470185
0.6735	Remote Similarity	NPC77481
0.6735	Remote Similarity	NPC233770
0.6691	Remote Similarity	NPC469494
0.6667	Remote Similarity	NPC477793
0.6667	Remote Similarity	NPC271269
0.6667	Remote Similarity	NPC476023
0.6667	Remote Similarity	NPC329919
0.6643	Remote Similarity	NPC230889
0.6642	Remote Similarity	NPC470973
0.6641	Remote Similarity	NPC80650
0.6615	Remote Similarity	NPC275100
0.6614	Remote Similarity	NPC474716
0.6614	Remote Similarity	NPC475800
0.6593	Remote Similarity	NPC469515
0.6541	Remote Similarity	NPC476713
0.6541	Remote Similarity	NPC476712
0.6541	Remote Similarity	NPC147707
0.6535	Remote Similarity	NPC154601
0.6496	Remote Similarity	NPC473802
0.6496	Remote Similarity	NPC16709
0.6496	Remote Similarity	NPC262026
0.6489	Remote Similarity	NPC473877
0.6489	Remote Similarity	NPC474497
0.6484	Remote Similarity	NPC266514
0.6484	Remote Similarity	NPC251330
0.6471	Remote Similarity	NPC23963
0.6466	Remote Similarity	NPC476710
0.6466	Remote Similarity	NPC476711
0.6462	Remote Similarity	NPC196073
0.6462	Remote Similarity	NPC195435
0.6449	Remote Similarity	NPC473709
0.6449	Remote Similarity	NPC473919
0.6439	Remote Similarity	NPC477266
0.6434	Remote Similarity	NPC78189
0.6423	Remote Similarity	NPC188222
0.6423	Remote Similarity	NPC310035
0.6423	Remote Similarity	NPC282003
0.6418	Remote Similarity	NPC296822
0.6412	Remote Similarity	NPC317107
0.6403	Remote Similarity	NPC471939
0.6397	Remote Similarity	NPC477143
0.6397	Remote Similarity	NPC477140
0.6377	Remote Similarity	NPC303006
0.637	Remote Similarity	NPC476558
0.6364	Remote Similarity	NPC314500
0.6364	Remote Similarity	NPC317687
0.6357	Remote Similarity	NPC469558
0.6357	Remote Similarity	NPC324327
0.6357	Remote Similarity	NPC194620
0.6357	Remote Similarity	NPC471940
0.6357	Remote Similarity	NPC72813
0.6357	Remote Similarity	NPC474421
0.6357	Remote Similarity	NPC326994
0.6357	Remote Similarity	NPC204556
0.635	Remote Similarity	NPC156379
0.635	Remote Similarity	NPC475383
0.6349	Remote Similarity	NPC84042
0.6349	Remote Similarity	NPC472753
0.6349	Remote Similarity	NPC476270
0.6349	Remote Similarity	NPC305085
0.6348	Remote Similarity	NPC67254
0.6343	Remote Similarity	NPC474333
0.6343	Remote Similarity	NPC270478
0.6328	Remote Similarity	NPC474741
0.6324	Remote Similarity	NPC470186
0.6324	Remote Similarity	NPC241050
0.632	Remote Similarity	NPC306908
0.6312	Remote Similarity	NPC476091
0.6312	Remote Similarity	NPC476078
0.6308	Remote Similarity	NPC169888
0.6308	Remote Similarity	NPC14862
0.6308	Remote Similarity	NPC475150
0.6308	Remote Similarity	NPC327286
0.6308	Remote Similarity	NPC55972
0.6308	Remote Similarity	NPC474664
0.6308	Remote Similarity	NPC233379
0.6299	Remote Similarity	NPC472754
0.6299	Remote Similarity	NPC39996
0.6299	Remote Similarity	NPC474747
0.6296	Remote Similarity	NPC476190
0.6288	Remote Similarity	NPC170375
0.6288	Remote Similarity	NPC12270
0.6286	Remote Similarity	NPC217901
0.6281	Remote Similarity	NPC477684
0.6279	Remote Similarity	NPC9303
0.6279	Remote Similarity	NPC16313
0.6277	Remote Similarity	NPC475003
0.6276	Remote Similarity	NPC99864
0.627	Remote Similarity	NPC475949
0.627	Remote Similarity	NPC233932
0.627	Remote Similarity	NPC469551
0.6268	Remote Similarity	NPC162495
0.626	Remote Similarity	NPC87335
0.626	Remote Similarity	NPC473578
0.626	Remote Similarity	NPC42662
0.626	Remote Similarity	NPC15218
0.6259	Remote Similarity	NPC318445
0.6259	Remote Similarity	NPC316133
0.6259	Remote Similarity	NPC11895
0.625	Remote Similarity	NPC118902
0.625	Remote Similarity	NPC475871
0.625	Remote Similarity	NPC469980
0.625	Remote Similarity	NPC104161
0.625	Remote Similarity	NPC475945
0.6241	Remote Similarity	NPC469865
0.6241	Remote Similarity	NPC168849
0.6241	Remote Similarity	NPC475273
0.624	Remote Similarity	NPC17326
0.624	Remote Similarity	NPC134454
0.6231	Remote Similarity	NPC477513
0.6224	Remote Similarity	NPC477189
0.6224	Remote Similarity	NPC475606
0.6224	Remote Similarity	NPC475389
0.6224	Remote Similarity	NPC475314
0.6224	Remote Similarity	NPC473838
0.6224	Remote Similarity	NPC251564
0.622	Remote Similarity	NPC164598
0.622	Remote Similarity	NPC474339
0.622	Remote Similarity	NPC201718
0.622	Remote Similarity	NPC47880
0.622	Remote Similarity	NPC474742
0.622	Remote Similarity	NPC112613
0.6214	Remote Similarity	NPC81736
0.6214	Remote Similarity	NPC172154
0.6207	Remote Similarity	NPC120420
0.6202	Remote Similarity	NPC472756
0.6198	Remote Similarity	NPC159369
0.6198	Remote Similarity	NPC39290
0.6197	Remote Similarity	NPC477712
0.6197	Remote Similarity	NPC477713
0.6194	Remote Similarity	NPC89018
0.619	Remote Similarity	NPC246209
0.6187	Remote Similarity	NPC170538
0.6183	Remote Similarity	NPC322903
0.6183	Remote Similarity	NPC208461
0.6183	Remote Similarity	NPC289702
0.6181	Remote Similarity	NPC475139
0.6181	Remote Similarity	NPC474508
0.6181	Remote Similarity	NPC316401
0.6181	Remote Similarity	NPC180902
0.6181	Remote Similarity	NPC473485
0.6179	Remote Similarity	NPC61275
0.6179	Remote Similarity	NPC212486
0.6176	Remote Similarity	NPC469684
0.6176	Remote Similarity	NPC471146
0.6176	Remote Similarity	NPC477116
0.6176	Remote Similarity	NPC27999
0.6176	Remote Similarity	NPC473590
0.6172	Remote Similarity	NPC149371
0.6172	Remote Similarity	NPC478176
0.6172	Remote Similarity	NPC471148
0.617	Remote Similarity	NPC225049
0.617	Remote Similarity	NPC293112
0.6165	Remote Similarity	NPC474229
0.6165	Remote Similarity	NPC29501
0.616	Remote Similarity	NPC21302
0.616	Remote Similarity	NPC11396
0.6159	Remote Similarity	NPC473808
0.6154	Remote Similarity	NPC475802
0.6154	Remote Similarity	NPC472615
0.6154	Remote Similarity	NPC473252
0.6148	Remote Similarity	NPC238667
0.6148	Remote Similarity	NPC88867
0.6148	Remote Similarity	NPC226608
0.6148	Remote Similarity	NPC73314
0.6143	Remote Similarity	NPC265557
0.6143	Remote Similarity	NPC472399
0.6143	Remote Similarity	NPC105926
0.6143	Remote Similarity	NPC91693
0.6143	Remote Similarity	NPC120724
0.6143	Remote Similarity	NPC67251
0.6143	Remote Similarity	NPC18945
0.6142	Remote Similarity	NPC473224
0.6138	Remote Similarity	NPC314361
0.6136	Remote Similarity	NPC475922
0.6136	Remote Similarity	NPC133729
0.6131	Remote Similarity	NPC284707
0.6131	Remote Similarity	NPC476714
0.6124	Remote Similarity	NPC472750
0.6124	Remote Similarity	NPC472747

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 NPC280498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	94
0.1-0.2	679
0.2-0.3	3284
0.3-0.4	3930
0.4-0.5	997
0.5-0.6	158
0.6-0.7	8
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
0.6471	Remote Similarity	NPD6921	Approved
0.6336	Remote Similarity	NPD6421	Discontinued
0.6299	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD1719	Phase 1
0.6276	Remote Similarity	NPD8415	Approved
0.6259	Remote Similarity	NPD7642	Approved
0.6242	Remote Similarity	NPD8384	Approved
0.6233	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD8074	Phase 3
0.6056	Remote Similarity	NPD8273	Phase 1
0.6056	Remote Similarity	NPD8451	Approved
0.6031	Remote Similarity	NPD5357	Phase 1
0.6014	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD8392	Approved
0.6	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD8390	Approved
0.5942	Remote Similarity	NPD7500	Approved
0.592	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD7829	Approved
0.5915	Remote Similarity	NPD7830	Approved
0.5887	Remote Similarity	NPD8444	Approved
0.5887	Remote Similarity	NPD6698	Approved
0.5887	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD46	Approved
0.5874	Remote Similarity	NPD8341	Approved
0.5874	Remote Similarity	NPD8340	Approved
0.5874	Remote Similarity	NPD8342	Approved
0.5874	Remote Similarity	NPD8299	Approved
0.5846	Remote Similarity	NPD5344	Discontinued
0.5845	Remote Similarity	NPD8080	Discontinued
0.584	Remote Similarity	NPD7983	Approved
0.5828	Remote Similarity	NPD6334	Approved
0.5828	Remote Similarity	NPD6333	Approved
0.5809	Remote Similarity	NPD2204	Approved
0.5786	Remote Similarity	NPD7641	Discontinued
0.5781	Remote Similarity	NPD4228	Discovery
0.5776	Remote Similarity	NPD818	Approved
0.5776	Remote Similarity	NPD819	Approved
0.5775	Remote Similarity	NPD8267	Approved
0.5775	Remote Similarity	NPD8268	Approved
0.5775	Remote Similarity	NPD8269	Approved
0.5775	Remote Similarity	NPD8266	Approved
0.576	Remote Similarity	NPD3168	Discontinued
0.5735	Remote Similarity	NPD6420	Discontinued
0.5714	Remote Similarity	NPD7115	Discovery
0.5693	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD5779	Approved
0.5669	Remote Similarity	NPD5778	Approved
0.5664	Remote Similarity	NPD5983	Phase 2
0.5659	Remote Similarity	NPD7839	Suspended
0.5646	Remote Similarity	NPD6033	Approved
0.5638	Remote Similarity	NPD7260	Phase 2
0.563	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7623	Phase 3
0.5625	Remote Similarity	NPD5282	Discontinued
0.562	Remote Similarity	NPD6371	Approved
0.5612	Remote Similarity	NPD4632	Approved
0.5603	Remote Similarity	NPD8137	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