NPASS Compound

Structure

CID320936 OpenBabel06191716152D 49 48 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 5 6 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 13 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 25 1 0 0 0 0 14 20 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 23 1 0 0 0 0 17 30 1 0 0 0 0 18 24 1 0 0 0 0 18 31 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 2 1 1 0 0 0 21 3 1 6 0 0 0 21 32 1 0 0 0 0 22 4 1 6 0 0 0 22 26 1 0 0 0 0 22 35 1 0 0 0 0 23 15 1 6 0 0 0 23 33 1 0 0 0 0 24 16 1 1 0 0 0 24 34 1 0 0 0 0 25 36 1 6 0 0 0 26 37 1 1 0 0 0 27 14 1 6 0 0 0 27 32 1 0 0 0 0 27 48 1 0 0 0 0 28 38 2 0 0 0 0 28 39 1 0 0 0 0 29 40 2 0 0 0 0 29 41 1 0 0 0 0 30 42 2 0 0 0 0 30 48 1 0 0 0 0 31 43 2 0 0 0 0 31 49 1 0 0 0 0 32 49 1 1 0 0 0 33 44 2 0 0 0 0 33 45 1 0 0 0 0 34 46 2 0 0 0 0 34 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	705.39
Volume:	714.861
LogP:	2.972
LogD:	2.432
LogS:	-3.134
# Rotatable Bonds:	31
TPSA:	268.28
# H-Bond Aceptor:	15
# H-Bond Donor:	8
# Rings:	0
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.043
Synthetic Accessibility Score:	5.008
Fsp3:	0.824
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.469
MDCK Permeability:	0.00012563643394969404
Pgp-inhibitor:	0.0
Pgp-substrate:	0.975
Human Intestinal Absorption (HIA):	0.994
20% Bioavailability (F20%):	0.852
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	76.00572204589844%
Volume Distribution (VD):	0.533
Pgp-substrate:	10.801794052124023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.11
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	5.0
Half-life (T1/2):	0.889

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.7
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.781
Skin Sensitization:	0.62
Carcinogencity:	0.403
Eye Corrosion:	0.958
Eye Irritation:	0.268
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC320936

Natural Product ID:	NPC320936
*Common Name:**	Fumonisin B2
IUPAC Name:	(2R)-2-[2-[(5R,6R,7S,9S,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-16,18-dihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
Synonyms:	Fumonisin B2
Standard InCHIKey:	UXDPXZQHTDAXOZ-STOIETHLSA-N
Standard InCHI:	InChI=1S/C34H59NO14/c1-5-6-12-21(3)32(49-31(43)18-24(34(46)47)16-29(40)41)27(48-30(42)17-23(33(44)45)15-28(38)39)14-20(2)11-9-7-8-10-13-25(36)19-26(37)22(4)35/h20-27,32,36-37H,5-19,35H2,1-4H3,(H,38,39)(H,40,41)(H,44,45)(H,46,47)/t20-,21+,22-,23+,24+,25+,26-,27-,32+/m0/s1
SMILES:	CCCC[C@H]([C@H]([C@@H](OC(=O)C[C@H](C(=O)O)CC(=O)O)C[C@H](CCCCCC[C@H](C[C@@H]([C@@H](N)C)O)O)C)OC(=O)C[C@H](C(=O)O)CC(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1700939
PubChem CID:	2733489
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001792] Fumonisins

*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
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)88611-1]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np058103o]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/JR9620000040]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/00021369.1966.10858561]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/00021369.1972.10860562]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/00021369.1985.10867263]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[10695672]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12458767]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542363]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387655]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	sponge-derived	n.a.	PMID[15387655]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15556711]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620260]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17653510]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827758]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20014861]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20028011]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21176790]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21543515]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21774474]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22921072]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24684908]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25044953]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25062661]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293978]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26040782]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26132344]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26414728]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27245874]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32159958]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6073032]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	Database[Article]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO14234	Aspergillus niger	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2
Potency	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[529678]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-8.37	%	PMID[529679]
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[529678]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	15.12	%	PMID[529679]

☑ 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 NPC320936 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	163
0.1-0.2	2535
0.2-0.3	18142
0.3-0.4	13171
0.4-0.5	7813
0.5-0.6	753
0.6-0.7	105
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7582	Intermediate Similarity	NPC477729
0.7292	Intermediate Similarity	NPC160066
0.7222	Intermediate Similarity	NPC227051
0.7174	Intermediate Similarity	NPC470282
0.7143	Intermediate Similarity	NPC83839
0.7111	Intermediate Similarity	NPC145748
0.7111	Intermediate Similarity	NPC95478
0.7111	Intermediate Similarity	NPC155670
0.7033	Intermediate Similarity	NPC253975
0.7033	Intermediate Similarity	NPC192025
0.7033	Intermediate Similarity	NPC125253
0.6932	Remote Similarity	NPC473984
0.6813	Remote Similarity	NPC47135
0.6765	Remote Similarity	NPC227622
0.6742	Remote Similarity	NPC475616
0.6735	Remote Similarity	NPC470283
0.6702	Remote Similarity	NPC477728
0.6667	Remote Similarity	NPC86064
0.6629	Remote Similarity	NPC474003
0.6593	Remote Similarity	NPC314466
0.6556	Remote Similarity	NPC315131
0.6556	Remote Similarity	NPC478017
0.6556	Remote Similarity	NPC315535
0.6552	Remote Similarity	NPC474100
0.6552	Remote Similarity	NPC475260
0.6552	Remote Similarity	NPC51249
0.6552	Remote Similarity	NPC475232
0.6552	Remote Similarity	NPC43219
0.6552	Remote Similarity	NPC473775
0.6552	Remote Similarity	NPC473699
0.6548	Remote Similarity	NPC286842
0.6531	Remote Similarity	NPC270005
0.6531	Remote Similarity	NPC208537
0.65	Remote Similarity	NPC470363
0.6471	Remote Similarity	NPC82315
0.646	Remote Similarity	NPC477237
0.6456	Remote Similarity	NPC190385
0.6452	Remote Similarity	NPC477730
0.6444	Remote Similarity	NPC316242
0.6404	Remote Similarity	NPC228411
0.6392	Remote Similarity	NPC470284
0.6355	Remote Similarity	NPC137453
0.6353	Remote Similarity	NPC469925
0.6348	Remote Similarity	NPC477238
0.6341	Remote Similarity	NPC17455
0.6329	Remote Similarity	NPC8979
0.6316	Remote Similarity	NPC314268
0.6316	Remote Similarity	NPC477515
0.6316	Remote Similarity	NPC473791
0.6316	Remote Similarity	NPC476523
0.6316	Remote Similarity	NPC313802
0.6316	Remote Similarity	NPC67917
0.6304	Remote Similarity	NPC474702
0.6265	Remote Similarity	NPC106216
0.6265	Remote Similarity	NPC88898
0.6262	Remote Similarity	NPC471844
0.625	Remote Similarity	NPC474403
0.6234	Remote Similarity	NPC123814
0.6216	Remote Similarity	NPC76660
0.6216	Remote Similarity	NPC276995
0.6207	Remote Similarity	NPC478256
0.6207	Remote Similarity	NPC28526
0.619	Remote Similarity	NPC316250
0.618	Remote Similarity	NPC476248
0.6163	Remote Similarity	NPC470110
0.6163	Remote Similarity	NPC195165
0.6162	Remote Similarity	NPC159369
0.6162	Remote Similarity	NPC39290
0.6154	Remote Similarity	NPC330017
0.6136	Remote Similarity	NPC477200
0.6136	Remote Similarity	NPC470268
0.6102	Remote Similarity	NPC315783
0.6098	Remote Similarity	NPC68974
0.6092	Remote Similarity	NPC472579
0.6087	Remote Similarity	NPC233108
0.6076	Remote Similarity	NPC2801
0.6061	Remote Similarity	NPC203170
0.6061	Remote Similarity	NPC292345
0.6055	Remote Similarity	NPC317534
0.6047	Remote Similarity	NPC222327
0.6047	Remote Similarity	NPC188231
0.6047	Remote Similarity	NPC241949
0.6047	Remote Similarity	NPC470109
0.6044	Remote Similarity	NPC476324
0.6044	Remote Similarity	NPC476130
0.6026	Remote Similarity	NPC474322
0.6022	Remote Similarity	NPC470014
0.6	Remote Similarity	NPC308096
0.6	Remote Similarity	NPC291228
0.6	Remote Similarity	NPC208657
0.6	Remote Similarity	NPC138435
0.5978	Remote Similarity	NPC472594
0.5963	Remote Similarity	NPC236644
0.596	Remote Similarity	NPC314364
0.596	Remote Similarity	NPC52533
0.5955	Remote Similarity	NPC476696
0.5955	Remote Similarity	NPC476695
0.5955	Remote Similarity	NPC476694
0.5955	Remote Similarity	NPC306973
0.593	Remote Similarity	NPC470108
0.593	Remote Similarity	NPC476330
0.5909	Remote Similarity	NPC474299
0.5909	Remote Similarity	NPC474298
0.5909	Remote Similarity	NPC473985
0.5909	Remote Similarity	NPC475808
0.5909	Remote Similarity	NPC28348
0.5909	Remote Similarity	NPC315531
0.5904	Remote Similarity	NPC319131
0.59	Remote Similarity	NPC322966
0.5893	Remote Similarity	NPC477997
0.5889	Remote Similarity	NPC185419
0.5889	Remote Similarity	NPC184550
0.5889	Remote Similarity	NPC141325
0.5888	Remote Similarity	NPC42320
0.5888	Remote Similarity	NPC188453
0.5882	Remote Similarity	NPC235788
0.5875	Remote Similarity	NPC469937
0.5875	Remote Similarity	NPC53463
0.5875	Remote Similarity	NPC320588
0.5875	Remote Similarity	NPC23155
0.5872	Remote Similarity	NPC74035
0.587	Remote Similarity	NPC217725
0.587	Remote Similarity	NPC477002
0.5862	Remote Similarity	NPC209734
0.5859	Remote Similarity	NPC476717
0.5859	Remote Similarity	NPC258824
0.5856	Remote Similarity	NPC70235
0.5854	Remote Similarity	NPC322148
0.5851	Remote Similarity	NPC191345
0.5851	Remote Similarity	NPC252483
0.5849	Remote Similarity	NPC220234
0.5843	Remote Similarity	NPC211428
0.5843	Remote Similarity	NPC476285
0.5843	Remote Similarity	NPC476291
0.5841	Remote Similarity	NPC34977
0.5841	Remote Similarity	NPC246399
0.5833	Remote Similarity	NPC302188
0.5833	Remote Similarity	NPC116320
0.5833	Remote Similarity	NPC211049
0.5833	Remote Similarity	NPC119922
0.5818	Remote Similarity	NPC475918
0.5816	Remote Similarity	NPC151176
0.5816	Remote Similarity	NPC475963
0.5816	Remote Similarity	NPC3464
0.5814	Remote Similarity	NPC314103
0.581	Remote Similarity	NPC471843
0.58	Remote Similarity	NPC51662
0.5795	Remote Similarity	NPC477760
0.5795	Remote Similarity	NPC477754
0.5795	Remote Similarity	NPC206601
0.5795	Remote Similarity	NPC477758
0.5795	Remote Similarity	NPC477761
0.5795	Remote Similarity	NPC477759
0.5789	Remote Similarity	NPC22742
0.5789	Remote Similarity	NPC294748
0.5789	Remote Similarity	NPC85759
0.5789	Remote Similarity	NPC318258
0.5789	Remote Similarity	NPC261750
0.5789	Remote Similarity	NPC158302
0.5789	Remote Similarity	NPC477344
0.5789	Remote Similarity	NPC146992
0.5789	Remote Similarity	NPC477346
0.5789	Remote Similarity	NPC1111
0.5784	Remote Similarity	NPC65359
0.5784	Remote Similarity	NPC470114
0.5784	Remote Similarity	NPC476019
0.5783	Remote Similarity	NPC179624
0.5778	Remote Similarity	NPC33267
0.5778	Remote Similarity	NPC114640
0.5778	Remote Similarity	NPC126366
0.5778	Remote Similarity	NPC169976
0.5778	Remote Similarity	NPC170963
0.5778	Remote Similarity	NPC324165
0.5772	Remote Similarity	NPC477793
0.5772	Remote Similarity	NPC329919
0.5765	Remote Similarity	NPC469923
0.5761	Remote Similarity	NPC472595
0.5758	Remote Similarity	NPC475206
0.5758	Remote Similarity	NPC476715
0.575	Remote Similarity	NPC72722
0.5747	Remote Similarity	NPC469926
0.5747	Remote Similarity	NPC474402
0.5745	Remote Similarity	NPC83108
0.5745	Remote Similarity	NPC214030
0.5743	Remote Similarity	NPC193386
0.5743	Remote Similarity	NPC470009
0.573	Remote Similarity	NPC50228
0.573	Remote Similarity	NPC268922
0.573	Remote Similarity	NPC224700
0.573	Remote Similarity	NPC320663
0.573	Remote Similarity	NPC97736
0.5729	Remote Similarity	NPC207657
0.5728	Remote Similarity	NPC472197
0.5726	Remote Similarity	NPC6531
0.5714	Remote Similarity	NPC121062
0.5714	Remote Similarity	NPC96966
0.5714	Remote Similarity	NPC15413
0.5714	Remote Similarity	NPC29222
0.5714	Remote Similarity	NPC474468
0.5702	Remote Similarity	NPC314629

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 NPC320936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	131
0.1-0.2	2594
0.2-0.3	4051
0.3-0.4	1682
0.4-0.5	513
0.5-0.6	152
0.6-0.7	27
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
0.7115	Intermediate Similarity	NPD8087	Discontinued
0.6813	Remote Similarity	NPD7345	Approved
0.6765	Remote Similarity	NPD8139	Approved
0.6765	Remote Similarity	NPD8086	Approved
0.6765	Remote Similarity	NPD8084	Approved
0.6765	Remote Similarity	NPD8085	Approved
0.6765	Remote Similarity	NPD8083	Approved
0.6765	Remote Similarity	NPD8138	Approved
0.6765	Remote Similarity	NPD8082	Approved
0.6735	Remote Similarity	NPD8394	Approved
0.6731	Remote Similarity	NPD8393	Approved
0.6699	Remote Similarity	NPD8275	Approved
0.6699	Remote Similarity	NPD8276	Approved
0.6667	Remote Similarity	NPD8307	Discontinued
0.6667	Remote Similarity	NPD8140	Approved
0.6635	Remote Similarity	NPD8081	Approved
0.6627	Remote Similarity	NPD9421	Phase 1
0.6585	Remote Similarity	NPD7909	Approved
0.6556	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8346	Approved
0.6549	Remote Similarity	NPD8345	Approved
0.6549	Remote Similarity	NPD8347	Approved
0.6456	Remote Similarity	NPD9023	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD8444	Approved
0.6341	Remote Similarity	NPD9676	Phase 3
0.6275	Remote Similarity	NPD6428	Approved
0.625	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8305	Approved
0.6239	Remote Similarity	NPD8306	Approved
0.6234	Remote Similarity	NPD3215	Phase 1
0.6162	Remote Similarity	NPD3716	Discontinued
0.6105	Remote Similarity	NPD882	Phase 2
0.6105	Remote Similarity	NPD883	Phase 2
0.6102	Remote Similarity	NPD7830	Approved
0.6102	Remote Similarity	NPD7829	Approved
0.6091	Remote Similarity	NPD6941	Approved
0.6087	Remote Similarity	NPD3160	Suspended
0.6068	Remote Similarity	NPD8267	Approved
0.6068	Remote Similarity	NPD8266	Approved
0.6068	Remote Similarity	NPD8269	Approved
0.6068	Remote Similarity	NPD8268	Approved
0.6067	Remote Similarity	NPD6704	Discontinued
0.6061	Remote Similarity	NPD618	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9454	Approved
0.6	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD8301	Approved
0.5981	Remote Similarity	NPD8300	Approved
0.5974	Remote Similarity	NPD3214	Discontinued
0.5918	Remote Similarity	NPD619	Phase 3
0.5905	Remote Similarity	NPD881	Approved
0.5893	Remote Similarity	NPD6421	Discontinued
0.5889	Remote Similarity	NPD1147	Phase 2
0.5875	Remote Similarity	NPD3730	Approved
0.5875	Remote Similarity	NPD3728	Approved
0.587	Remote Similarity	NPD11	Approved
0.587	Remote Similarity	NPD376	Approved
0.587	Remote Similarity	NPD2257	Approved
0.5862	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD2696	Approved
0.5843	Remote Similarity	NPD8277	Approved
0.5843	Remote Similarity	NPD2697	Approved
0.5843	Remote Similarity	NPD2694	Approved
0.5843	Remote Similarity	NPD2695	Approved
0.5833	Remote Similarity	NPD9656	Approved
0.5812	Remote Similarity	NPD7641	Discontinued
0.5806	Remote Similarity	NPD2689	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD7643	Phase 1
0.5761	Remote Similarity	NPD632	Discontinued
0.573	Remote Similarity	NPD8278	Approved
0.573	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD7983	Approved
0.5714	Remote Similarity	NPD3187	Discontinued
0.5699	Remote Similarity	NPD1453	Phase 1
0.5698	Remote Similarity	NPD1151	Approved
0.5684	Remote Similarity	NPD3732	Approved
0.5682	Remote Similarity	NPD2263	Discontinued
0.5682	Remote Similarity	NPD375	Phase 2
0.5679	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD1447	Phase 3
0.5673	Remote Similarity	NPD1446	Phase 3
0.5667	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD9439	Approved
0.5663	Remote Similarity	NPD9438	Approved
0.5656	Remote Similarity	NPD8341	Approved
0.5656	Remote Similarity	NPD8340	Approved
0.5656	Remote Similarity	NPD8299	Approved
0.5656	Remote Similarity	NPD8342	Approved
0.5641	Remote Similarity	NPD6940	Discontinued
0.5641	Remote Similarity	NPD9018	Approved
0.5641	Remote Similarity	NPD9017	Approved
0.5636	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.562	Remote Similarity	NPD8080	Discontinued
0.5619	Remote Similarity	NPD573	Clinical (unspecified phase)
0.561	Remote Similarity	NPD8451	Approved
0.5607	Remote Similarity	NPD3715	Approved
0.5607	Remote Similarity	NPD8038	Phase 2
0.5607	Remote Similarity	NPD3713	Approved
0.5607	Remote Similarity	NPD3714	Approved
0.5604	Remote Similarity	NPD7532	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