NPASS Compound

Structure

CID240887 OpenBabel06191716042D 27 30 0 0 1 0 0 0 0 0999 V2000 -5.6902 -3.0584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8196 -1.3312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9547 0.5455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2563 -2.1574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3885 -0.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3857 -0.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2591 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8252 -1.1817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8252 -2.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.5180 1.3717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9491 0.3960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -3.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4487 -3.7655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8503 -0.9592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8503 -3.2062 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 5 1 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 7 1 0 0 0 0 4 19 2 0 0 0 0 5 9 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 20 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 18 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 26 1 0 0 0 0 14 25 1 0 0 0 0 15 25 1 0 0 0 0 16 22 2 0 0 0 0 16 26 1 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 24 1 0 0 0 0 18 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.05
Volume:	341.042
LogP:	4.352
LogD:	1.778
LogS:	-4.617
# Rotatable Bonds:	1
TPSA:	146.66
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	3.664
Fsp3:	0.111
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:	-5.264
MDCK Permeability:	9.379370567330625e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.447
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	96.2163314819336%
Volume Distribution (VD):	0.555
Pgp-substrate:	6.545452117919922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.602
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.581
CYP2C9-substrate:	0.284
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	3.462
Half-life (T1/2):	0.565

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.013
Drug-inuced Liver Injury (DILI):	0.832
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.817
Carcinogencity:	0.127
Eye Corrosion:	0.046
Eye Irritation:	0.913
Respiratory Toxicity:	0.43

Download Data

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

Natural Product: NPC240887

Natural Product ID:	NPC240887
*Common Name:**	Norstictic Acid
IUPAC Name:	n.a.
Synonyms:	Norstictic Acid
Standard InCHIKey:	IEVVSJFLBYOUCJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O9/c1-5-3-8(20)7(4-19)14-9(5)16(22)26-13-6(2)12(21)10-11(15(13)25-14)18(24)27-17(10)23/h3-4,18,20-21,24H,1-2H3
SMILES:	O=Cc1c(O)cc(c2c1Oc1c(OC2=O)c(C)c(c2c1C(O)OC2=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228281
PubChem CID:	5379540
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO2574	Usnea articulata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17629329]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2574	Usnea articulata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2602	Usnea longissima	Species	Parmeliaceae	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
ED50	1
IC50	3
Ki	2
Others	7
Potency	19

Activity Type	# Activity
Individual Protein	24
Organism	5
Others	1
Protein-Protein Interaction	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PMID[532719]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	7943.3	nM	PMID[532719]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PMID[532719]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	7943.3	nM	PMID[532719]
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	Potency	=	2238.7	nM	PMID[532719]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	15811.4	nM	PMID[532719]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	10000.0	nM	PMID[532719]
NPT277	Individual Protein	Caspase-1	Homo sapiens	Potency	=	6309.6	nM	PMID[532719]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	39810.7	nM	PMID[532719]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[532719]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[532719]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[532719]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[532719]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[532719]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[532719]
NPT2	Others	Unspecified		IC50	=	580000.0	nM	PMID[532718]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	6309.6	nM	PMID[532719]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	12589.3	nM	PMID[532719]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	18.0	%	PMID[532720]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	0.33	g	PMID[532720]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	TIME	=	408.0	hr	PMID[532720]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	ED50	=	32.0	uM	PMID[532720]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	IC50	=	549.54	nM	PMID[532721]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Ki	=	420.0	nM	PMID[532721]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	10.9	%	PMID[532721]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	IC50	=	1148.15	nM	PMID[532721]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Ki	=	630.0	nM	PMID[532721]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	1.823	%	PMID[532721]
NPT23878	SINGLE PROTEIN	Translin-associated protein X	Homo sapiens	Inhibition	=	66.0	%	PMID[532722]

☑ 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 NPC240887 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	399
0.1-0.2	1955
0.2-0.3	4416
0.3-0.4	10213
0.4-0.5	8073
0.5-0.6	3803
0.6-0.7	5599
0.7-0.8	6872
0.8-0.85	1258
0.85-0.9	86
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470091
1.0	High Similarity	NPC329161
0.9576	High Similarity	NPC26568
0.9518	High Similarity	NPC246716
0.9518	High Similarity	NPC10576
0.9518	High Similarity	NPC17219
0.9518	High Similarity	NPC1827
0.9405	High Similarity	NPC181523
0.9401	High Similarity	NPC239440
0.9401	High Similarity	NPC20543
0.9398	High Similarity	NPC292788
0.9398	High Similarity	NPC272485
0.9349	High Similarity	NPC139350
0.9337	High Similarity	NPC20216
0.9277	High Similarity	NPC112981
0.9235	High Similarity	NPC289147
0.9217	High Similarity	NPC156082
0.9186	High Similarity	NPC113446
0.9036	High Similarity	NPC143050
0.8947	High Similarity	NPC124470
0.8947	High Similarity	NPC109827
0.8935	High Similarity	NPC267153
0.8929	High Similarity	NPC93739
0.8922	High Similarity	NPC200594
0.8889	High Similarity	NPC49487
0.8889	High Similarity	NPC99613
0.8882	High Similarity	NPC29160
0.8876	High Similarity	NPC474350
0.8876	High Similarity	NPC300984
0.8876	High Similarity	NPC284007
0.883	High Similarity	NPC234331
0.8824	High Similarity	NPC8070
0.881	High Similarity	NPC47623
0.8795	High Similarity	NPC149618
0.8795	High Similarity	NPC89625
0.8795	High Similarity	NPC471800
0.8793	High Similarity	NPC199533
0.8793	High Similarity	NPC470454
0.8786	High Similarity	NPC260263
0.8786	High Similarity	NPC158226
0.8779	High Similarity	NPC165979
0.8779	High Similarity	NPC163130
0.8757	High Similarity	NPC303565
0.875	High Similarity	NPC83763
0.875	High Similarity	NPC238381
0.875	High Similarity	NPC168616
0.8721	High Similarity	NPC471180
0.8706	High Similarity	NPC144843
0.8706	High Similarity	NPC469575
0.8678	High Similarity	NPC471181
0.8675	High Similarity	NPC273483
0.8663	High Similarity	NPC472452
0.8655	High Similarity	NPC197168
0.8655	High Similarity	NPC317781
0.8647	High Similarity	NPC66288
0.8644	High Similarity	NPC183843
0.8644	High Similarity	NPC84494
0.8644	High Similarity	NPC245059
0.8644	High Similarity	NPC212290
0.8636	High Similarity	NPC196771
0.8631	High Similarity	NPC54928
0.8629	High Similarity	NPC98776
0.8621	High Similarity	NPC298778
0.8614	High Similarity	NPC133856
0.8613	High Similarity	NPC471288
0.8605	High Similarity	NPC326520
0.8605	High Similarity	NPC25361
0.8596	High Similarity	NPC470448
0.8596	High Similarity	NPC164047
0.8596	High Similarity	NPC108767
0.8596	High Similarity	NPC294965
0.8596	High Similarity	NPC470452
0.8596	High Similarity	NPC470453
0.8588	High Similarity	NPC475886
0.8588	High Similarity	NPC469600
0.8588	High Similarity	NPC474287
0.8588	High Similarity	NPC470358
0.858	High Similarity	NPC474345
0.858	High Similarity	NPC165977
0.858	High Similarity	NPC68381
0.858	High Similarity	NPC146803
0.858	High Similarity	NPC472607
0.858	High Similarity	NPC217677
0.8571	High Similarity	NPC223375
0.8571	High Similarity	NPC475825
0.8571	High Similarity	NPC472386
0.8563	High Similarity	NPC473967
0.8555	High Similarity	NPC474042
0.8555	High Similarity	NPC170245
0.8555	High Similarity	NPC174734
0.8555	High Similarity	NPC178851
0.8554	High Similarity	NPC119929
0.8547	High Similarity	NPC7483
0.8547	High Similarity	NPC270837
0.8547	High Similarity	NPC236132
0.8547	High Similarity	NPC234004
0.8538	High Similarity	NPC474187
0.8538	High Similarity	NPC474186
0.8538	High Similarity	NPC474351
0.8538	High Similarity	NPC475883
0.8538	High Similarity	NPC474779
0.8531	High Similarity	NPC473713
0.8531	High Similarity	NPC475233
0.8529	High Similarity	NPC45846
0.8525	High Similarity	NPC220369
0.8523	High Similarity	NPC233956
0.8523	High Similarity	NPC472054
0.8521	High Similarity	NPC146211
0.8521	High Similarity	NPC472456
0.8508	High Similarity	NPC105591
0.8508	High Similarity	NPC174486
0.8508	High Similarity	NPC73703
0.8497	Intermediate Similarity	NPC327652
0.8497	Intermediate Similarity	NPC7752
0.8494	Intermediate Similarity	NPC291049
0.8494	Intermediate Similarity	NPC233267
0.8488	Intermediate Similarity	NPC8300
0.8488	Intermediate Similarity	NPC125991
0.848	Intermediate Similarity	NPC14353
0.848	Intermediate Similarity	NPC56085
0.848	Intermediate Similarity	NPC474770
0.848	Intermediate Similarity	NPC228785
0.8478	Intermediate Similarity	NPC314020
0.8478	Intermediate Similarity	NPC214901
0.8478	Intermediate Similarity	NPC477082
0.8475	Intermediate Similarity	NPC63105
0.8475	Intermediate Similarity	NPC469601
0.8475	Intermediate Similarity	NPC236327
0.8475	Intermediate Similarity	NPC290304
0.8471	Intermediate Similarity	NPC77679
0.8471	Intermediate Similarity	NPC190020
0.8471	Intermediate Similarity	NPC167595
0.8471	Intermediate Similarity	NPC84935
0.847	Intermediate Similarity	NPC321046
0.8466	Intermediate Similarity	NPC271385
0.8466	Intermediate Similarity	NPC254540
0.8466	Intermediate Similarity	NPC211594
0.8466	Intermediate Similarity	NPC292794
0.8466	Intermediate Similarity	NPC5029
0.8466	Intermediate Similarity	NPC76128
0.8466	Intermediate Similarity	NPC30432
0.8466	Intermediate Similarity	NPC157522
0.8466	Intermediate Similarity	NPC111536
0.8466	Intermediate Similarity	NPC172807
0.8457	Intermediate Similarity	NPC473202
0.8457	Intermediate Similarity	NPC211309
0.8457	Intermediate Similarity	NPC472381
0.8457	Intermediate Similarity	NPC471287
0.8457	Intermediate Similarity	NPC117911
0.8457	Intermediate Similarity	NPC259905
0.8457	Intermediate Similarity	NPC472383
0.8452	Intermediate Similarity	NPC475116
0.8452	Intermediate Similarity	NPC175978
0.8452	Intermediate Similarity	NPC271681
0.8452	Intermediate Similarity	NPC289968
0.8448	Intermediate Similarity	NPC329119
0.8444	Intermediate Similarity	NPC228209
0.8443	Intermediate Similarity	NPC164527
0.8443	Intermediate Similarity	NPC213382
0.8439	Intermediate Similarity	NPC327809
0.8439	Intermediate Similarity	NPC475985
0.8439	Intermediate Similarity	NPC273959
0.8439	Intermediate Similarity	NPC470178
0.8439	Intermediate Similarity	NPC470772
0.8434	Intermediate Similarity	NPC105415
0.843	Intermediate Similarity	NPC61010
0.843	Intermediate Similarity	NPC278052
0.843	Intermediate Similarity	NPC40491
0.8427	Intermediate Similarity	NPC472380
0.8427	Intermediate Similarity	NPC472382
0.8427	Intermediate Similarity	NPC472384
0.8427	Intermediate Similarity	NPC107244
0.8421	Intermediate Similarity	NPC100123
0.8421	Intermediate Similarity	NPC62518
0.8421	Intermediate Similarity	NPC279732
0.8421	Intermediate Similarity	NPC215375
0.8418	Intermediate Similarity	NPC199357
0.8418	Intermediate Similarity	NPC72455
0.8418	Intermediate Similarity	NPC277510
0.8415	Intermediate Similarity	NPC295436
0.8412	Intermediate Similarity	NPC150227
0.8412	Intermediate Similarity	NPC301897
0.8409	Intermediate Similarity	NPC22195
0.8409	Intermediate Similarity	NPC224462
0.8409	Intermediate Similarity	NPC212748
0.8409	Intermediate Similarity	NPC241874
0.8409	Intermediate Similarity	NPC477573
0.8409	Intermediate Similarity	NPC21190
0.8409	Intermediate Similarity	NPC281835
0.8409	Intermediate Similarity	NPC477572
0.8409	Intermediate Similarity	NPC44558
0.8409	Intermediate Similarity	NPC477571
0.8409	Intermediate Similarity	NPC183357
0.8409	Intermediate Similarity	NPC105511
0.8402	Intermediate Similarity	NPC475895
0.84	Intermediate Similarity	NPC477154
0.84	Intermediate Similarity	NPC298847
0.84	Intermediate Similarity	NPC42892
0.84	Intermediate Similarity	NPC93099
0.84	Intermediate Similarity	NPC6588

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 NPC240887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	1016
0.2-0.3	2090
0.3-0.4	2692
0.4-0.5	1694
0.5-0.6	833
0.6-0.7	299
0.7-0.8	128
0.8-0.85	18
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8488	Intermediate Similarity	NPD6232	Discontinued
0.8457	Intermediate Similarity	NPD5844	Phase 1
0.84	Intermediate Similarity	NPD3818	Discontinued
0.8343	Intermediate Similarity	NPD7473	Discontinued
0.8315	Intermediate Similarity	NPD6559	Discontinued
0.8268	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD2533	Approved
0.8253	Intermediate Similarity	NPD2534	Approved
0.8253	Intermediate Similarity	NPD2532	Approved
0.8129	Intermediate Similarity	NPD37	Approved
0.8101	Intermediate Similarity	NPD7074	Phase 3
0.8092	Intermediate Similarity	NPD4966	Approved
0.8092	Intermediate Similarity	NPD4965	Approved
0.8092	Intermediate Similarity	NPD4967	Phase 2
0.8081	Intermediate Similarity	NPD2801	Approved
0.8057	Intermediate Similarity	NPD5494	Approved
0.8045	Intermediate Similarity	NPD7054	Approved
0.8023	Intermediate Similarity	NPD1934	Approved
0.8011	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD919	Approved
0.7989	Intermediate Similarity	NPD3882	Suspended
0.7977	Intermediate Similarity	NPD7819	Suspended
0.7977	Intermediate Similarity	NPD1465	Phase 2
0.7977	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3817	Phase 2
0.7914	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7199	Phase 2
0.7903	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7228	Approved
0.7886	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7808	Phase 3
0.7857	Intermediate Similarity	NPD6797	Phase 2
0.7849	Intermediate Similarity	NPD3226	Approved
0.7841	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7251	Discontinued
0.7809	Intermediate Similarity	NPD6959	Discontinued
0.7784	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6166	Phase 2
0.7747	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7075	Discontinued
0.7733	Intermediate Similarity	NPD920	Approved
0.7722	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5710	Approved
0.7667	Intermediate Similarity	NPD5711	Approved
0.7665	Intermediate Similarity	NPD1551	Phase 2
0.7661	Intermediate Similarity	NPD1511	Approved
0.7657	Intermediate Similarity	NPD7411	Suspended
0.764	Intermediate Similarity	NPD3749	Approved
0.7634	Intermediate Similarity	NPD8312	Approved
0.7634	Intermediate Similarity	NPD8313	Approved
0.763	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6801	Discontinued
0.76	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6599	Discontinued
0.76	Intermediate Similarity	NPD4380	Phase 2
0.76	Intermediate Similarity	NPD7783	Phase 2
0.7572	Intermediate Similarity	NPD1512	Approved
0.7571	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2935	Discontinued
0.7553	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2800	Approved
0.7528	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5402	Approved
0.7527	Intermediate Similarity	NPD7240	Approved
0.7513	Intermediate Similarity	NPD8434	Phase 2
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1653	Approved
0.7457	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6799	Approved
0.7449	Intermediate Similarity	NPD6780	Approved
0.7449	Intermediate Similarity	NPD6778	Approved
0.7449	Intermediate Similarity	NPD6782	Approved
0.7449	Intermediate Similarity	NPD6781	Approved
0.7449	Intermediate Similarity	NPD6776	Approved
0.7449	Intermediate Similarity	NPD6777	Approved
0.7449	Intermediate Similarity	NPD6779	Approved
0.7432	Intermediate Similarity	NPD3926	Phase 2
0.7427	Intermediate Similarity	NPD1243	Approved
0.7425	Intermediate Similarity	NPD447	Suspended
0.7412	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD2346	Discontinued
0.7389	Intermediate Similarity	NPD7768	Phase 2
0.7384	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3750	Approved
0.7384	Intermediate Similarity	NPD4628	Phase 3
0.7381	Intermediate Similarity	NPD1607	Approved
0.7368	Intermediate Similarity	NPD1549	Phase 2
0.7337	Intermediate Similarity	NPD7697	Approved
0.7337	Intermediate Similarity	NPD7696	Phase 3
0.7337	Intermediate Similarity	NPD7698	Approved
0.7321	Intermediate Similarity	NPD230	Phase 1
0.7314	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7870	Phase 2
0.73	Intermediate Similarity	NPD7871	Phase 2
0.7294	Intermediate Similarity	NPD1510	Phase 2
0.7294	Intermediate Similarity	NPD2799	Discontinued
0.7294	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD7874	Approved
0.7291	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1240	Approved
0.7249	Intermediate Similarity	NPD7685	Pre-registration
0.7246	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3751	Discontinued
0.7216	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6823	Phase 2
0.7196	Intermediate Similarity	NPD5953	Discontinued
0.7194	Intermediate Similarity	NPD6535	Approved
0.7194	Intermediate Similarity	NPD6534	Approved
0.7192	Intermediate Similarity	NPD7701	Phase 2
0.7189	Intermediate Similarity	NPD7229	Phase 3
0.7159	Intermediate Similarity	NPD7390	Discontinued
0.7151	Intermediate Similarity	NPD2796	Approved
0.715	Intermediate Similarity	NPD8150	Discontinued
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5403	Approved
0.7119	Intermediate Similarity	NPD5401	Approved
0.7118	Intermediate Similarity	NPD1933	Approved
0.7097	Intermediate Similarity	NPD3787	Discontinued
0.7093	Intermediate Similarity	NPD3748	Approved
0.709	Intermediate Similarity	NPD7286	Phase 2
0.7087	Intermediate Similarity	NPD7801	Approved
0.7086	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7700	Phase 2
0.7085	Intermediate Similarity	NPD7699	Phase 2
0.7059	Intermediate Similarity	NPD943	Approved
0.7056	Intermediate Similarity	NPD7458	Discontinued
0.7056	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8127	Discontinued
0.7031	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6674	Discontinued
0.7022	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2344	Approved
0.7011	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8455	Phase 2
0.6995	Remote Similarity	NPD7680	Approved
0.6994	Remote Similarity	NPD651	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6213	Phase 3
0.697	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6212	Phase 3
0.6968	Remote Similarity	NPD5242	Approved
0.6961	Remote Similarity	NPD8320	Phase 1
0.6961	Remote Similarity	NPD8319	Approved
0.6959	Remote Similarity	NPD1613	Approved
0.6959	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6100	Approved
0.6954	Remote Similarity	NPD6099	Approved
0.6949	Remote Similarity	NPD6190	Approved
0.6948	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5006	Approved
0.6946	Remote Similarity	NPD5005	Approved
0.6946	Remote Similarity	NPD1203	Approved
0.6941	Remote Similarity	NPD2313	Discontinued
0.6927	Remote Similarity	NPD8067	Phase 3
0.6923	Remote Similarity	NPD6832	Phase 2
0.6919	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7930	Approved
0.6889	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6273	Approved
0.6884	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3027	Phase 3
0.6879	Remote Similarity	NPD6651	Approved
0.6864	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9494	Approved
0.686	Remote Similarity	NPD4060	Phase 1
0.6859	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5408	Approved
0.6857	Remote Similarity	NPD5405	Approved
0.6857	Remote Similarity	NPD5406	Approved
0.6857	Remote Similarity	NPD5404	Approved
0.6854	Remote Similarity	NPD2309	Approved
0.6845	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3764	Approved
0.6842	Remote Similarity	NPD411	Approved
0.6832	Remote Similarity	NPD4420	Approved
0.6824	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1471	Phase 3
0.6818	Remote Similarity	NPD4287	Approved
0.6812	Remote Similarity	NPD7584	Approved
0.6811	Remote Similarity	NPD5760	Phase 2
0.6811	Remote Similarity	NPD5761	Phase 2
0.68	Remote Similarity	NPD7033	Discontinued
0.68	Remote Similarity	NPD4308	Phase 3
0.6786	Remote Similarity	NPD1283	Approved
0.6784	Remote Similarity	NPD4625	Phase 3
0.6782	Remote Similarity	NPD8090	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