NPASS Compound

Structure

CID110810 OpenBabel06191715462D 21 23 0 0 0 0 0 0 0 0999 V2000 4.1481 1.4653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8115 -1.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3226 0.0249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6448 2.8967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3184 0.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4966 -0.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4751 2.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8188 2.4141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4822 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6565 0.0096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8132 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6562 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8256 -0.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0177 0.9676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5067 -1.4185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3040 2.9100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0132 2.8948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 -1.4367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8554 1.4382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8206 -0.4843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 21 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 11 2 0 0 0 0 8 18 1 0 0 0 0 9 12 2 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.06
Volume:	276.613
LogP:	3.482
LogD:	2.584
LogS:	-3.694
# Rotatable Bonds:	1
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	3.138
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.282
MDCK Permeability:	3.927970283257309e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.245
20% Bioavailability (F20%):	0.185
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	92.75480651855469%
Volume Distribution (VD):	0.67
Pgp-substrate:	18.038082122802734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.762
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.497
CYP2C9-substrate:	0.684
CYP2D6-inhibitor:	0.078
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.045

ADMET: Excretion

Clearance (CL):	7.613
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.029
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.489
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.506
Skin Sensitization:	0.942
Carcinogencity:	0.046
Eye Corrosion:	0.412
Eye Irritation:	0.935
Respiratory Toxicity:	0.254

Download Data

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

Natural Product: NPC110810

Natural Product ID:	NPC110810
*Common Name:**	QAPJKCNKHLDDAK-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QAPJKCNKHLDDAK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O6/c1-5-3-6(16)10-12-9(5)7(17)4-8(18)11(12)14(20)15(21-2)13(10)19/h3-4,16-19H,1-2H3
SMILES:	Cc1cc(c2c3c1c(cc(c3C(=O)C(=C2O)OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3596258
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002653] Phenalenes [CHEMONTID:0002654] Phenalenones

*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
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	%max	=	20.5	%	PMID[458570]
NPT23356	PROTEIN FAMILY	Phospho-N-acetylmuramoyl-pentapeptide-transferase/UDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase	Escherichia coli K-12	IC50	=	54000.0	nM	PMID[458569]

☑ 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 NPC110810 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	381
0.1-0.2	1652
0.2-0.3	3845
0.3-0.4	10329
0.4-0.5	8702
0.5-0.6	4725
0.6-0.7	5948
0.7-0.8	5594
0.8-0.85	1289
0.85-0.9	204
0.9-0.95	26
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC267205
0.9085	High Similarity	NPC471906
0.9078	High Similarity	NPC182255
0.9078	High Similarity	NPC94076
0.9058	High Similarity	NPC254847
0.9058	High Similarity	NPC191976
0.9014	High Similarity	NPC84266
0.9	High Similarity	NPC190457
0.9	High Similarity	NPC143438
0.8993	High Similarity	NPC53001
0.8993	High Similarity	NPC53414
0.8993	High Similarity	NPC53206
0.8993	High Similarity	NPC471905
0.8944	High Similarity	NPC474961
0.8929	High Similarity	NPC87723
0.8919	High Similarity	NPC472211
0.8913	High Similarity	NPC12070
0.8904	High Similarity	NPC80370
0.8897	High Similarity	NPC7943
0.8897	High Similarity	NPC22005
0.8897	High Similarity	NPC34802
0.8897	High Similarity	NPC123202
0.8889	High Similarity	NPC28632
0.8873	High Similarity	NPC204045
0.8873	High Similarity	NPC305845
0.8873	High Similarity	NPC246638
0.8865	High Similarity	NPC242994
0.8865	High Similarity	NPC138099
0.8849	High Similarity	NPC249272
0.8841	High Similarity	NPC114183
0.8836	High Similarity	NPC27221
0.8836	High Similarity	NPC256672
0.8836	High Similarity	NPC7025
0.8819	High Similarity	NPC244691
0.8819	High Similarity	NPC193703
0.8819	High Similarity	NPC48762
0.8819	High Similarity	NPC21599
0.8819	High Similarity	NPC227841
0.8811	High Similarity	NPC135524
0.8808	High Similarity	NPC228654
0.8803	High Similarity	NPC169452
0.8803	High Similarity	NPC181560
0.8786	High Similarity	NPC118919
0.8784	High Similarity	NPC230848
0.8777	High Similarity	NPC282780
0.8777	High Similarity	NPC44437
0.8777	High Similarity	NPC166480
0.8777	High Similarity	NPC270899
0.8777	High Similarity	NPC474519
0.8776	High Similarity	NPC100985
0.8776	High Similarity	NPC97029
0.8776	High Similarity	NPC329933
0.8776	High Similarity	NPC158338
0.8776	High Similarity	NPC97028
0.8776	High Similarity	NPC288036
0.8776	High Similarity	NPC65589
0.8768	High Similarity	NPC309430
0.8768	High Similarity	NPC478190
0.8768	High Similarity	NPC175738
0.8767	High Similarity	NPC56433
0.8767	High Similarity	NPC290194
0.8767	High Similarity	NPC289042
0.8767	High Similarity	NPC312929
0.8767	High Similarity	NPC245584
0.8767	High Similarity	NPC126767
0.8767	High Similarity	NPC190648
0.8767	High Similarity	NPC118027
0.8759	High Similarity	NPC62219
0.8759	High Similarity	NPC198305
0.8759	High Similarity	NPC34482
0.8759	High Similarity	NPC27659
0.8741	High Similarity	NPC290550
0.8741	High Similarity	NPC160499
0.8716	High Similarity	NPC202595
0.8716	High Similarity	NPC325983
0.8716	High Similarity	NPC147735
0.8716	High Similarity	NPC294646
0.8714	High Similarity	NPC290803
0.8705	High Similarity	NPC314048
0.8705	High Similarity	NPC48036
0.8699	High Similarity	NPC470570
0.8699	High Similarity	NPC136878
0.8693	High Similarity	NPC219686
0.869	High Similarity	NPC19896
0.8686	High Similarity	NPC92624
0.8681	High Similarity	NPC73061
0.8681	High Similarity	NPC193555
0.8671	High Similarity	NPC156872
0.8658	High Similarity	NPC72958
0.8658	High Similarity	NPC232645
0.8658	High Similarity	NPC149526
0.8658	High Similarity	NPC474417
0.8652	High Similarity	NPC158481
0.8639	High Similarity	NPC37709
0.8639	High Similarity	NPC259632
0.863	High Similarity	NPC12402
0.8623	High Similarity	NPC259942
0.8623	High Similarity	NPC147757
0.8621	High Similarity	NPC293545
0.8621	High Similarity	NPC451542
0.8621	High Similarity	NPC313047
0.8621	High Similarity	NPC474203
0.8621	High Similarity	NPC295712
0.8621	High Similarity	NPC174905
0.8618	High Similarity	NPC474637
0.8613	High Similarity	NPC179898
0.8611	High Similarity	NPC187843
0.86	High Similarity	NPC175978
0.86	High Similarity	NPC87708
0.8592	High Similarity	NPC471452
0.8591	High Similarity	NPC470568
0.8591	High Similarity	NPC255641
0.8591	High Similarity	NPC119929
0.8591	High Similarity	NPC290954
0.8582	High Similarity	NPC283590
0.8582	High Similarity	NPC130899
0.8582	High Similarity	NPC70859
0.8582	High Similarity	NPC278375
0.8582	High Similarity	NPC61153
0.8582	High Similarity	NPC161632
0.8581	High Similarity	NPC472841
0.8571	High Similarity	NPC225173
0.8571	High Similarity	NPC180261
0.8571	High Similarity	NPC37299
0.8571	High Similarity	NPC163846
0.8571	High Similarity	NPC254603
0.8562	High Similarity	NPC10764
0.8561	High Similarity	NPC41847
0.8552	High Similarity	NPC40118
0.8552	High Similarity	NPC232021
0.8552	High Similarity	NPC126534
0.8551	High Similarity	NPC278928
0.8543	High Similarity	NPC329844
0.8543	High Similarity	NPC210942
0.8543	High Similarity	NPC169990
0.8542	High Similarity	NPC165172
0.8542	High Similarity	NPC168471
0.8533	High Similarity	NPC258249
0.8533	High Similarity	NPC470569
0.8533	High Similarity	NPC478148
0.8529	High Similarity	NPC477454
0.8529	High Similarity	NPC10926
0.8523	High Similarity	NPC269420
0.8523	High Similarity	NPC477221
0.8521	High Similarity	NPC86524
0.8514	High Similarity	NPC472135
0.8514	High Similarity	NPC125801
0.8511	High Similarity	NPC50924
0.8503	High Similarity	NPC474630
0.85	High Similarity	NPC88864
0.8497	Intermediate Similarity	NPC201127
0.8493	Intermediate Similarity	NPC297600
0.8493	Intermediate Similarity	NPC296752
0.8493	Intermediate Similarity	NPC310340
0.8487	Intermediate Similarity	NPC66508
0.8487	Intermediate Similarity	NPC226656
0.8483	Intermediate Similarity	NPC275734
0.8483	Intermediate Similarity	NPC265178
0.8478	Intermediate Similarity	NPC237225
0.8477	Intermediate Similarity	NPC40356
0.8477	Intermediate Similarity	NPC217447
0.8477	Intermediate Similarity	NPC154683
0.8472	Intermediate Similarity	NPC162939
0.8467	Intermediate Similarity	NPC8745
0.8467	Intermediate Similarity	NPC473691
0.8467	Intermediate Similarity	NPC267846
0.8462	Intermediate Similarity	NPC264022
0.8456	Intermediate Similarity	NPC173978
0.8456	Intermediate Similarity	NPC13238
0.8456	Intermediate Similarity	NPC172329
0.8456	Intermediate Similarity	NPC2569
0.8451	Intermediate Similarity	NPC283088
0.8446	Intermediate Similarity	NPC306488
0.8446	Intermediate Similarity	NPC5820
0.8446	Intermediate Similarity	NPC178343
0.8442	Intermediate Similarity	NPC324736
0.8442	Intermediate Similarity	NPC104876
0.8442	Intermediate Similarity	NPC245891
0.844	Intermediate Similarity	NPC52407
0.844	Intermediate Similarity	NPC40524
0.844	Intermediate Similarity	NPC213485
0.844	Intermediate Similarity	NPC139074
0.844	Intermediate Similarity	NPC171968
0.8435	Intermediate Similarity	NPC158874
0.8435	Intermediate Similarity	NPC29932
0.8435	Intermediate Similarity	NPC475201
0.8435	Intermediate Similarity	NPC189650
0.8431	Intermediate Similarity	NPC180924
0.8431	Intermediate Similarity	NPC474360
0.8429	Intermediate Similarity	NPC474517
0.8429	Intermediate Similarity	NPC72669
0.8425	Intermediate Similarity	NPC201297
0.8425	Intermediate Similarity	NPC49108
0.8421	Intermediate Similarity	NPC93552
0.8421	Intermediate Similarity	NPC193200
0.8421	Intermediate Similarity	NPC208806
0.8421	Intermediate Similarity	NPC107109
0.8417	Intermediate Similarity	NPC109123
0.8417	Intermediate Similarity	NPC102829
0.8417	Intermediate Similarity	NPC120488

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 NPC110810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	998
0.2-0.3	1513
0.3-0.4	2851
0.4-0.5	1947
0.5-0.6	1043
0.6-0.7	330
0.7-0.8	100
0.8-0.85	15
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9058	High Similarity	NPD1509	Clinical (unspecified phase)
0.8819	High Similarity	NPD7390	Discontinued
0.8378	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD1607	Approved
0.8235	Intermediate Similarity	NPD1201	Approved
0.8217	Intermediate Similarity	NPD6959	Discontinued
0.8165	Intermediate Similarity	NPD6232	Discontinued
0.8138	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1510	Phase 2
0.8129	Intermediate Similarity	NPD1470	Approved
0.8125	Intermediate Similarity	NPD7473	Discontinued
0.8112	Intermediate Similarity	NPD943	Approved
0.8112	Intermediate Similarity	NPD1240	Approved
0.8095	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD5408	Approved
0.8082	Intermediate Similarity	NPD5404	Approved
0.8082	Intermediate Similarity	NPD5405	Approved
0.8082	Intermediate Similarity	NPD5406	Approved
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2534	Approved
0.7961	Intermediate Similarity	NPD1512	Approved
0.7949	Intermediate Similarity	NPD7819	Suspended
0.7949	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1549	Phase 2
0.7829	Intermediate Similarity	NPD1511	Approved
0.7799	Intermediate Similarity	NPD7075	Discontinued
0.7778	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1934	Approved
0.7756	Intermediate Similarity	NPD4380	Phase 2
0.7722	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2935	Discontinued
0.7682	Intermediate Similarity	NPD2800	Approved
0.7673	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6599	Discontinued
0.7632	Intermediate Similarity	NPD3750	Approved
0.7625	Intermediate Similarity	NPD3882	Suspended
0.7622	Intermediate Similarity	NPD1164	Approved
0.761	Intermediate Similarity	NPD2801	Approved
0.758	Intermediate Similarity	NPD3226	Approved
0.7562	Intermediate Similarity	NPD3817	Phase 2
0.755	Intermediate Similarity	NPD2346	Discontinued
0.7547	Intermediate Similarity	NPD6801	Discontinued
0.7536	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3300	Phase 2
0.7517	Intermediate Similarity	NPD6651	Approved
0.7515	Intermediate Similarity	NPD6166	Phase 2
0.7515	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7484	Intermediate Similarity	NPD6799	Approved
0.7484	Intermediate Similarity	NPD7411	Suspended
0.7483	Intermediate Similarity	NPD2796	Approved
0.7469	Intermediate Similarity	NPD3749	Approved
0.741	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7768	Phase 2
0.7394	Intermediate Similarity	NPD5711	Approved
0.7394	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1551	Phase 2
0.7368	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD6100	Approved
0.7353	Intermediate Similarity	NPD6559	Discontinued
0.7338	Intermediate Similarity	NPD1243	Approved
0.7333	Intermediate Similarity	NPD1247	Approved
0.7317	Intermediate Similarity	NPD919	Approved
0.731	Intermediate Similarity	NPD1283	Approved
0.7303	Intermediate Similarity	NPD3748	Approved
0.7294	Intermediate Similarity	NPD6797	Phase 2
0.7284	Intermediate Similarity	NPD1465	Phase 2
0.7273	Intermediate Similarity	NPD5494	Approved
0.7256	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1651	Approved
0.7251	Intermediate Similarity	NPD7251	Discontinued
0.7241	Intermediate Similarity	NPD8150	Discontinued
0.7233	Intermediate Similarity	NPD920	Approved
0.7219	Intermediate Similarity	NPD230	Phase 1
0.7209	Intermediate Similarity	NPD7808	Phase 3
0.7208	Intermediate Similarity	NPD1471	Phase 3
0.7208	Intermediate Similarity	NPD2344	Approved
0.7203	Intermediate Similarity	NPD2932	Approved
0.719	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4625	Phase 3
0.7179	Intermediate Similarity	NPD7003	Approved
0.7179	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD9269	Phase 2
0.7153	Intermediate Similarity	NPD4750	Phase 3
0.7135	Intermediate Similarity	NPD7074	Phase 3
0.7134	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD9268	Approved
0.7133	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7118	Intermediate Similarity	NPD3818	Discontinued
0.7115	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1281	Approved
0.7091	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3019	Approved
0.7078	Intermediate Similarity	NPD2799	Discontinued
0.7076	Intermediate Similarity	NPD6020	Phase 2
0.7076	Intermediate Similarity	NPD7054	Approved
0.707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD9493	Approved
0.7041	Intermediate Similarity	NPD3926	Phase 2
0.7037	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7472	Approved
0.7025	Intermediate Similarity	NPD2309	Approved
0.702	Intermediate Similarity	NPD2313	Discontinued
0.702	Intermediate Similarity	NPD3764	Approved
0.7019	Intermediate Similarity	NPD5403	Approved
0.7011	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD6534	Approved
0.7	Intermediate Similarity	NPD6535	Approved
0.6995	Remote Similarity	NPD6780	Approved
0.6995	Remote Similarity	NPD6777	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD6782	Approved
0.6995	Remote Similarity	NPD6781	Approved
0.6995	Remote Similarity	NPD6776	Approved
0.698	Remote Similarity	NPD2798	Approved
0.6973	Remote Similarity	NPD7435	Discontinued
0.6939	Remote Similarity	NPD3972	Approved
0.6933	Remote Similarity	NPD7458	Discontinued
0.6913	Remote Similarity	NPD1203	Approved
0.6909	Remote Similarity	NPD37	Approved
0.6908	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5953	Discontinued
0.6885	Remote Similarity	NPD7699	Phase 2
0.6885	Remote Similarity	NPD7700	Phase 2
0.6884	Remote Similarity	NPD2342	Discontinued
0.6882	Remote Similarity	NPD7229	Phase 3
0.6882	Remote Similarity	NPD7696	Phase 3
0.6882	Remote Similarity	NPD7698	Approved
0.6882	Remote Similarity	NPD7697	Approved
0.6882	Remote Similarity	NPD3787	Discontinued
0.6879	Remote Similarity	NPD7286	Phase 2
0.6879	Remote Similarity	NPD7635	Approved
0.6878	Remote Similarity	NPD8151	Discontinued
0.6855	Remote Similarity	NPD4628	Phase 3
0.6849	Remote Similarity	NPD4626	Approved
0.6845	Remote Similarity	NPD8319	Approved
0.6845	Remote Similarity	NPD7871	Phase 2
0.6845	Remote Similarity	NPD7870	Phase 2
0.6845	Remote Similarity	NPD8320	Phase 1
0.6835	Remote Similarity	NPD74	Approved
0.6835	Remote Similarity	NPD9266	Approved
0.6828	Remote Similarity	NPD9545	Approved
0.6818	Remote Similarity	NPD2979	Phase 3
0.6818	Remote Similarity	NPD4060	Phase 1
0.6815	Remote Similarity	NPD1242	Phase 1
0.6813	Remote Similarity	NPD6190	Approved
0.6811	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6234	Discontinued
0.6797	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD411	Approved
0.6792	Remote Similarity	NPD2654	Approved
0.679	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4967	Phase 2
0.6786	Remote Similarity	NPD4965	Approved
0.6786	Remote Similarity	NPD4966	Approved
0.678	Remote Similarity	NPD8313	Approved
0.678	Remote Similarity	NPD8312	Approved
0.6779	Remote Similarity	NPD4749	Approved
0.6765	Remote Similarity	NPD846	Approved
0.6765	Remote Similarity	NPD940	Approved
0.6763	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD9267	Approved
0.6763	Remote Similarity	NPD9264	Approved
0.6763	Remote Similarity	NPD9263	Approved
0.6757	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1610	Phase 2
0.6755	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7874	Approved
0.6752	Remote Similarity	NPD4308	Phase 3
0.6744	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7701	Phase 2
0.6733	Remote Similarity	NPD1876	Approved
0.6726	Remote Similarity	NPD4288	Approved
0.6724	Remote Similarity	NPD7177	Discontinued
0.6723	Remote Similarity	NPD4955	Approved
0.6723	Remote Similarity	NPD4954	Approved
0.6723	Remote Similarity	NPD5028	Approved
0.6723	Remote Similarity	NPD5026	Approved
0.6723	Remote Similarity	NPD5034	Approved
0.6723	Remote Similarity	NPD36	Approved
0.6721	Remote Similarity	NPD4360	Phase 2
0.6721	Remote Similarity	NPD4363	Phase 3
0.6711	Remote Similarity	NPD1608	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