NPASS Compound

Structure

CID327620 OpenBabel06191716192D 21 21 0 0 1 0 0 0 0 0999 V2000 4.0000 -3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -4.3301 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 -1.0000 -0.0000 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 4.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 2 5 1 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 4 19 1 0 0 0 0 5 10 1 0 0 0 0 6 8 1 0 0 0 0 6 19 1 6 0 0 0 7 8 1 0 0 0 0 7 20 1 1 0 0 0 8 11 1 1 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 16 21 1 0 0 0 0 17 21 1 0 0 0 0 18 21 2 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.02
Volume:	270.144
LogP:	-1.679
LogD:	-0.019
LogS:	-0.342
# Rotatable Bonds:	6
TPSA:	167.66
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.281
Synthetic Accessibility Score:	5.132
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.203
MDCK Permeability:	0.00018836908566299826
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.937
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.271
Plasma Protein Binding (PPB):	22.410009384155273%
Volume Distribution (VD):	0.276
Pgp-substrate:	54.40919876098633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.028
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.643
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.691
Drug-inuced Liver Injury (DILI):	0.733
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.67
Skin Sensitization:	0.723
Carcinogencity:	0.196
Eye Corrosion:	0.014
Eye Irritation:	0.894
Respiratory Toxicity:	0.236

Download Data

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

Natural Product: NPC327620

Natural Product ID:	NPC327620
*Common Name:**	(3R,4S,5R)-5-(1-Carboxyethenoxy)-4-Hydroxy-3-Phosphonooxycyclohexene-1-Carboxylic Acid
IUPAC Name:	(3R,4S,5R)-5-(1-carboxyethenoxy)-4-hydroxy-3-phosphonooxycyclohexene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	QUTYKIXIUDQOLK-PRJMDXOYSA-N
Standard InCHI:	InChI=1S/C10H13O10P/c1-4(9(12)13)19-6-2-5(10(14)15)3-7(8(6)11)20-21(16,17)18/h3,6-8,11H,1-2H2,(H,12,13)(H,14,15)(H2,16,17,18)/t6-,7-,8+/m1/s1
SMILES:	C=C(C(=O)O)OC1CC(=CC(C1O)OP(=O)(O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL317037
PubChem CID:	439463
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000402] Organic phosphoric acids and derivatives [CHEMONTID:0000408] Phosphate esters [CHEMONTID:0003457] Alkyl phosphates [CHEMONTID:0003458] Monoalkyl phosphates

*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
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	DOI[10.1016/0006-291X(79)91731-5]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	DOI[10.1093/emboj/18.8.2021]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1091286]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10977898]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1100617]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11745165]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11750815]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12369847]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12467448]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12805358]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	ChEBI[131529]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[13610867]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[13831814]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14973046]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15031653]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15292242]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15610037]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1644759]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16630633]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[170247]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17765195]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[179975]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19026742]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19514719]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19561621]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21437340]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21988831]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22289691]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22855027]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23537328]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23676670]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[241475]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24206068]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24783849]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24831709]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24939187]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24966042]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24967680]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2543976]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25867074]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26195826]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26337258]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26670289]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26826371]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29897754]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[30302998]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[318639]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3283102]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[398096]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4877125]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4879561]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4908789]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[5332408]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[6102982]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[6284709]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[6338507]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7042909]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7601837]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8852895]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9470222]
NPO730	Escherichia coli	Species	Enterobacteriaceae	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
Kd	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3015	Individual Protein	5-enolpyruvylshikimate-3-phosphate synthase	Escherichia coli K-12	Kd	=	1000.0	nM	PMID[571085]
NPT3015	Individual Protein	5-enolpyruvylshikimate-3-phosphate synthase	Escherichia coli K-12	Kd	=	1000.0	nM	PMID[571086]

☑ 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 NPC327620 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	259
0.1-0.2	2170
0.2-0.3	6813
0.3-0.4	14244
0.4-0.5	12984
0.5-0.6	5062
0.6-0.7	1092
0.7-0.8	69
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.907	High Similarity	NPC316819
0.8256	Intermediate Similarity	NPC141195
0.8256	Intermediate Similarity	NPC47844
0.7692	Intermediate Similarity	NPC221510
0.7692	Intermediate Similarity	NPC159714
0.7634	Intermediate Similarity	NPC469809
0.7609	Intermediate Similarity	NPC253364
0.76	Intermediate Similarity	NPC20066
0.7525	Intermediate Similarity	NPC300584
0.7368	Intermediate Similarity	NPC77971
0.7308	Intermediate Similarity	NPC39996
0.7263	Intermediate Similarity	NPC474251
0.7234	Intermediate Similarity	NPC47450
0.7172	Intermediate Similarity	NPC471399
0.7143	Intermediate Similarity	NPC472008
0.7113	Intermediate Similarity	NPC112685
0.71	Intermediate Similarity	NPC303230
0.71	Intermediate Similarity	NPC6099
0.71	Intermediate Similarity	NPC114345
0.71	Intermediate Similarity	NPC473321
0.71	Intermediate Similarity	NPC327760
0.7075	Intermediate Similarity	NPC118902
0.7075	Intermediate Similarity	NPC104161
0.7075	Intermediate Similarity	NPC469980
0.7071	Intermediate Similarity	NPC477011
0.7071	Intermediate Similarity	NPC280612
0.7065	Intermediate Similarity	NPC272267
0.7041	Intermediate Similarity	NPC178215
0.7041	Intermediate Similarity	NPC472007
0.703	Intermediate Similarity	NPC162205
0.703	Intermediate Similarity	NPC11456
0.703	Intermediate Similarity	NPC273579
0.703	Intermediate Similarity	NPC288240
0.703	Intermediate Similarity	NPC295204
0.7019	Intermediate Similarity	NPC471144
0.701	Intermediate Similarity	NPC21469
0.701	Intermediate Similarity	NPC182383
0.7	Intermediate Similarity	NPC265856
0.7	Intermediate Similarity	NPC166554
0.7	Intermediate Similarity	NPC473619
0.6972	Remote Similarity	NPC264819
0.697	Remote Similarity	NPC280621
0.697	Remote Similarity	NPC20339
0.697	Remote Similarity	NPC21208
0.697	Remote Similarity	NPC40376
0.697	Remote Similarity	NPC48338
0.697	Remote Similarity	NPC89001
0.697	Remote Similarity	NPC233551
0.697	Remote Similarity	NPC473715
0.6952	Remote Similarity	NPC475949
0.6939	Remote Similarity	NPC47937
0.6939	Remote Similarity	NPC103523
0.6939	Remote Similarity	NPC472009
0.6939	Remote Similarity	NPC134865
0.6916	Remote Similarity	NPC472755
0.69	Remote Similarity	NPC139418
0.69	Remote Similarity	NPC477016
0.69	Remote Similarity	NPC477017
0.6893	Remote Similarity	NPC471142
0.6893	Remote Similarity	NPC36954
0.6882	Remote Similarity	NPC473536
0.6881	Remote Similarity	NPC266514
0.6869	Remote Similarity	NPC179659
0.6863	Remote Similarity	NPC475912
0.6837	Remote Similarity	NPC231009
0.6837	Remote Similarity	NPC66346
0.6837	Remote Similarity	NPC82795
0.6837	Remote Similarity	NPC103284
0.6837	Remote Similarity	NPC477014
0.6837	Remote Similarity	NPC132496
0.6837	Remote Similarity	NPC1083
0.6837	Remote Similarity	NPC110710
0.6837	Remote Similarity	NPC473651
0.6837	Remote Similarity	NPC107986
0.6837	Remote Similarity	NPC473478
0.6837	Remote Similarity	NPC473669
0.6837	Remote Similarity	NPC223871
0.6837	Remote Similarity	NPC283085
0.6837	Remote Similarity	NPC286338
0.6837	Remote Similarity	NPC477013
0.6832	Remote Similarity	NPC239517
0.6832	Remote Similarity	NPC473904
0.6832	Remote Similarity	NPC274075
0.6827	Remote Similarity	NPC477921
0.6789	Remote Similarity	NPC472749
0.6789	Remote Similarity	NPC472751
0.6778	Remote Similarity	NPC202011
0.6771	Remote Similarity	NPC297440
0.6768	Remote Similarity	NPC134807
0.6768	Remote Similarity	NPC477015
0.6768	Remote Similarity	NPC219498
0.6768	Remote Similarity	NPC232555
0.6768	Remote Similarity	NPC142117
0.6768	Remote Similarity	NPC171174
0.6768	Remote Similarity	NPC475581
0.6768	Remote Similarity	NPC308412
0.6768	Remote Similarity	NPC279267
0.6768	Remote Similarity	NPC107717
0.6768	Remote Similarity	NPC62118
0.6768	Remote Similarity	NPC69082
0.6768	Remote Similarity	NPC240695
0.6768	Remote Similarity	NPC473687
0.6768	Remote Similarity	NPC114694
0.6768	Remote Similarity	NPC210218
0.6768	Remote Similarity	NPC134885
0.6768	Remote Similarity	NPC204686
0.6768	Remote Similarity	NPC231096
0.6765	Remote Similarity	NPC146852
0.6762	Remote Similarity	NPC40812
0.6735	Remote Similarity	NPC163093
0.6733	Remote Similarity	NPC42598
0.6733	Remote Similarity	NPC93794
0.6733	Remote Similarity	NPC20621
0.6733	Remote Similarity	NPC318963
0.6733	Remote Similarity	NPC473504
0.6733	Remote Similarity	NPC40066
0.6733	Remote Similarity	NPC14901
0.6733	Remote Similarity	NPC130359
0.6733	Remote Similarity	NPC81778
0.6733	Remote Similarity	NPC91067
0.6731	Remote Similarity	NPC477922
0.6731	Remote Similarity	NPC270013
0.6731	Remote Similarity	NPC14961
0.6729	Remote Similarity	NPC110443
0.6729	Remote Similarity	NPC128733
0.6729	Remote Similarity	NPC476270
0.6729	Remote Similarity	NPC185141
0.6729	Remote Similarity	NPC133907
0.6729	Remote Similarity	NPC46998
0.6727	Remote Similarity	NPC477513
0.6726	Remote Similarity	NPC317687
0.6726	Remote Similarity	NPC66108
0.6702	Remote Similarity	NPC475711
0.6699	Remote Similarity	NPC476300
0.6699	Remote Similarity	NPC61275
0.6697	Remote Similarity	NPC472748
0.6696	Remote Similarity	NPC5103
0.6667	Remote Similarity	NPC477018
0.6667	Remote Similarity	NPC100921
0.6667	Remote Similarity	NPC329838
0.6667	Remote Similarity	NPC329615
0.6667	Remote Similarity	NPC320019
0.6667	Remote Similarity	NPC471567
0.6667	Remote Similarity	NPC120398
0.6667	Remote Similarity	NPC324017
0.6667	Remote Similarity	NPC149371
0.6667	Remote Similarity	NPC476315
0.6667	Remote Similarity	NPC472754
0.6667	Remote Similarity	NPC474232
0.6637	Remote Similarity	NPC317107
0.6636	Remote Similarity	NPC469852
0.6635	Remote Similarity	NPC474035
0.6635	Remote Similarity	NPC57405
0.6635	Remote Similarity	NPC303942
0.6635	Remote Similarity	NPC81386
0.6635	Remote Similarity	NPC121825
0.6635	Remote Similarity	NPC71589
0.6634	Remote Similarity	NPC320458
0.6634	Remote Similarity	NPC150063
0.6634	Remote Similarity	NPC172821
0.6634	Remote Similarity	NPC133730
0.6634	Remote Similarity	NPC171135
0.6634	Remote Similarity	NPC234077
0.6634	Remote Similarity	NPC261952
0.6634	Remote Similarity	NPC169511
0.6634	Remote Similarity	NPC39754
0.6634	Remote Similarity	NPC151403
0.6634	Remote Similarity	NPC61257
0.6634	Remote Similarity	NPC100454
0.6634	Remote Similarity	NPC191929
0.6634	Remote Similarity	NPC119740
0.6634	Remote Similarity	NPC320569
0.6634	Remote Similarity	NPC274446
0.6634	Remote Similarity	NPC242364
0.6634	Remote Similarity	NPC81045
0.6634	Remote Similarity	NPC287164
0.6634	Remote Similarity	NPC473905
0.6633	Remote Similarity	NPC116543
0.6633	Remote Similarity	NPC315559
0.6632	Remote Similarity	NPC317263
0.6607	Remote Similarity	NPC38154
0.6607	Remote Similarity	NPC471400
0.6606	Remote Similarity	NPC472750
0.6606	Remote Similarity	NPC472747
0.6606	Remote Similarity	NPC475871
0.6606	Remote Similarity	NPC475945
0.6602	Remote Similarity	NPC184463
0.6602	Remote Similarity	NPC30515
0.66	Remote Similarity	NPC477010
0.66	Remote Similarity	NPC309211
0.6581	Remote Similarity	NPC251310
0.6577	Remote Similarity	NPC469853
0.6574	Remote Similarity	NPC47880
0.6574	Remote Similarity	NPC15993
0.6574	Remote Similarity	NPC472753
0.6569	Remote Similarity	NPC474032
0.6566	Remote Similarity	NPC156804
0.6566	Remote Similarity	NPC70424
0.6566	Remote Similarity	NPC243618
0.6562	Remote Similarity	NPC180725

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 NPC327620 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	2713
0.2-0.3	3748
0.3-0.4	1769
0.4-0.5	512
0.5-0.6	167
0.6-0.7	11
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
0.6702	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6602	Remote Similarity	NPD7983	Approved
0.6465	Remote Similarity	NPD6110	Phase 1
0.6226	Remote Similarity	NPD5779	Approved
0.6226	Remote Similarity	NPD5778	Approved
0.614	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6319	Approved
0.6038	Remote Similarity	NPD7838	Discovery
0.6017	Remote Similarity	NPD8297	Approved
0.5978	Remote Similarity	NPD3704	Approved
0.5948	Remote Similarity	NPD4730	Approved
0.5948	Remote Similarity	NPD4729	Approved
0.5946	Remote Similarity	NPD4225	Approved
0.5946	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6649	Approved
0.5932	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6650	Approved
0.592	Remote Similarity	NPD8328	Phase 3
0.5914	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD4768	Approved
0.5913	Remote Similarity	NPD4767	Approved
0.5909	Remote Similarity	NPD7839	Suspended
0.5897	Remote Similarity	NPD6372	Approved
0.5897	Remote Similarity	NPD6373	Approved
0.5887	Remote Similarity	NPD8517	Approved
0.5887	Remote Similarity	NPD8513	Phase 3
0.5887	Remote Similarity	NPD8516	Approved
0.5887	Remote Similarity	NPD8515	Approved
0.5865	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5697	Approved
0.5847	Remote Similarity	NPD5248	Approved
0.5847	Remote Similarity	NPD5249	Phase 3
0.5847	Remote Similarity	NPD5247	Approved
0.5847	Remote Similarity	NPD5250	Approved
0.5847	Remote Similarity	NPD5251	Approved
0.5847	Remote Similarity	NPD6371	Approved
0.5841	Remote Similarity	NPD5344	Discontinued
0.5833	Remote Similarity	NPD4632	Approved
0.5825	Remote Similarity	NPD7154	Phase 3
0.5818	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6881	Approved
0.5812	Remote Similarity	NPD6686	Approved
0.5812	Remote Similarity	NPD6899	Approved
0.5776	Remote Similarity	NPD7128	Approved
0.5776	Remote Similarity	NPD5739	Approved
0.5776	Remote Similarity	NPD6402	Approved
0.5776	Remote Similarity	NPD6675	Approved
0.5763	Remote Similarity	NPD6012	Approved
0.5763	Remote Similarity	NPD6014	Approved
0.5763	Remote Similarity	NPD6013	Approved
0.5761	Remote Similarity	NPD3197	Phase 1
0.575	Remote Similarity	NPD6882	Approved
0.5726	Remote Similarity	NPD5701	Approved
0.5714	Remote Similarity	NPD7290	Approved
0.5714	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD6883	Approved
0.5691	Remote Similarity	NPD6009	Approved
0.5691	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7115	Discovery
0.5682	Remote Similarity	NPD73	Approved
0.5678	Remote Similarity	NPD7320	Approved
0.5678	Remote Similarity	NPD6011	Approved
0.5667	Remote Similarity	NPD6617	Approved
0.5667	Remote Similarity	NPD6847	Approved
0.5667	Remote Similarity	NPD8130	Phase 1
0.5667	Remote Similarity	NPD6869	Approved
0.566	Remote Similarity	NPD4249	Approved
0.5659	Remote Similarity	NPD8074	Phase 3
0.5652	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6101	Approved
0.5648	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD7641	Discontinued
0.5638	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD5983	Phase 2
0.5625	Remote Similarity	NPD7492	Approved
0.562	Remote Similarity	NPD6053	Discontinued
0.5618	Remote Similarity	NPD8959	Approved
0.5607	Remote Similarity	NPD4251	Approved
0.5607	Remote Similarity	NPD4250	Approved

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