NPASS Compound

Structure

CID103001 OpenBabel06191715452D 22 24 0 0 0 0 0 0 0 0999 V2000 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 2.5981 0.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -0.8660 0.5000 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 0.8660 0.5000 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 -4.3301 3.5000 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 0.0000 2.0000 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 11 1 0 0 0 0 2 12 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 19 2 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 18 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.09
Volume:	305.648
LogP:	3.259
LogD:	2.664
LogS:	-4.17
# Rotatable Bonds:	3
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.534
Synthetic Accessibility Score:	2.011
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.744
MDCK Permeability:	3.3874202927108854e-05
Pgp-inhibitor:	0.436
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.753

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	93.72132873535156%
Volume Distribution (VD):	0.898
Pgp-substrate:	4.096467971801758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.503
CYP2C19-inhibitor:	0.571
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.599
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.457
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	1.515
Half-life (T1/2):	0.275

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.923
AMES Toxicity:	0.615
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.523
Skin Sensitization:	0.775
Carcinogencity:	0.774
Eye Corrosion:	0.005
Eye Irritation:	0.653
Respiratory Toxicity:	0.148

Download Data

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

Natural Product: NPC103001

Natural Product ID:	NPC103001
*Common Name:**	(2-Methyl-4-Oxo-3-Phenylchromen-7-Yl) Acetate
IUPAC Name:	(2-methyl-4-oxo-3-phenylchromen-7-yl) acetate
Synonyms:	NSC-108339
Standard InCHIKey:	DPIAJERHFDBLPT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O4/c1-11-17(13-6-4-3-5-7-13)18(20)15-9-8-14(22-12(2)19)10-16(15)21-11/h3-10H,1-2H3
SMILES:	CC(=O)Oc1ccc2c(c1)oc(c(c2=O)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL243089
PubChem CID:	268208
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31500	Clycyrrhiza glabra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	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	3
Potency	14

Activity Type	# Activity
Individual Protein	11
Organism	1
Others	3
Uncleic Acid	2

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	=	31622.8	nM	PMID[540253]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	19952.6	nM	PMID[540253]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	3548.1	nM	PMID[540253]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[540253]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	33807.8	nM	PMID[540253]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	28183.8	nM	PMID[540253]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[540253]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[540253]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[540253]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[540253]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[540253]
NPT2	Others	Unspecified		Inhibition	=	3.1	%	PMID[540251]
NPT2	Others	Unspecified		Activity	=	7.1	%	PMID[540251]
NPT2	Others	Unspecified		Inhibition	=	16.1	%	PMID[540251]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	18492.7	nM	PMID[540253]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	3.3	nM	PMID[540253]

☑ 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 NPC103001 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	490
0.1-0.2	2003
0.2-0.3	5112
0.3-0.4	11496
0.4-0.5	5956
0.5-0.6	4635
0.6-0.7	6057
0.7-0.8	4418
0.8-0.85	1821
0.85-0.9	606
0.9-0.95	98
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.985	High Similarity	NPC136095
0.9556	High Similarity	NPC473209
0.9545	High Similarity	NPC292998
0.9478	High Similarity	NPC254741
0.9474	High Similarity	NPC66705
0.9416	High Similarity	NPC24075
0.9407	High Similarity	NPC253616
0.9394	High Similarity	NPC278556
0.9394	High Similarity	NPC284424
0.9343	High Similarity	NPC474037
0.9338	High Similarity	NPC36414
0.9333	High Similarity	NPC268081
0.9323	High Similarity	NPC182428
0.9323	High Similarity	NPC473655
0.9323	High Similarity	NPC101294
0.9286	High Similarity	NPC154217
0.927	High Similarity	NPC472515
0.9265	High Similarity	NPC228661
0.9254	High Similarity	NPC223354
0.9214	High Similarity	NPC196137
0.9214	High Similarity	NPC1886
0.9209	High Similarity	NPC36181
0.9191	High Similarity	NPC472516
0.9191	High Similarity	NPC161196
0.9185	High Similarity	NPC125269
0.9149	High Similarity	NPC181388
0.9149	High Similarity	NPC470322
0.9143	High Similarity	NPC112791
0.9143	High Similarity	NPC94794
0.9143	High Similarity	NPC196459
0.9143	High Similarity	NPC188632
0.9143	High Similarity	NPC470296
0.9143	High Similarity	NPC87609
0.9137	High Similarity	NPC254010
0.913	High Similarity	NPC262635
0.9124	High Similarity	NPC157855
0.9124	High Similarity	NPC250266
0.9124	High Similarity	NPC38153
0.9124	High Similarity	NPC266597
0.9118	High Similarity	NPC99854
0.9091	High Similarity	NPC474648
0.9085	High Similarity	NPC180477
0.9085	High Similarity	NPC140120
0.9078	High Similarity	NPC469953
0.9078	High Similarity	NPC469935
0.9078	High Similarity	NPC178627
0.9071	High Similarity	NPC313036
0.9065	High Similarity	NPC171094
0.9065	High Similarity	NPC172986
0.9065	High Similarity	NPC270883
0.9065	High Similarity	NPC261227
0.9058	High Similarity	NPC17848
0.9058	High Similarity	NPC201395
0.9051	High Similarity	NPC47815
0.9051	High Similarity	NPC61546
0.9051	High Similarity	NPC29353
0.9051	High Similarity	NPC234133
0.9051	High Similarity	NPC13408
0.9051	High Similarity	NPC124784
0.9051	High Similarity	NPC231772
0.9051	High Similarity	NPC72452
0.9051	High Similarity	NPC194281
0.9051	High Similarity	NPC127447
0.9051	High Similarity	NPC473887
0.9044	High Similarity	NPC172262
0.9023	High Similarity	NPC211120
0.9021	High Similarity	NPC161864
0.9021	High Similarity	NPC208303
0.9021	High Similarity	NPC183236
0.9015	High Similarity	NPC41721
0.9015	High Similarity	NPC49852
0.9015	High Similarity	NPC475496
0.9014	High Similarity	NPC57470
0.9014	High Similarity	NPC153758
0.9007	High Similarity	NPC470216
0.9	High Similarity	NPC147688
0.9	High Similarity	NPC156590
0.9	High Similarity	NPC205006
0.9	High Similarity	NPC103362
0.9	High Similarity	NPC110969
0.9	High Similarity	NPC64908
0.9	High Similarity	NPC118840
0.8993	High Similarity	NPC18260
0.8993	High Similarity	NPC303633
0.8993	High Similarity	NPC96565
0.8993	High Similarity	NPC220062
0.8993	High Similarity	NPC301217
0.8993	High Similarity	NPC216978
0.8993	High Similarity	NPC55018
0.8993	High Similarity	NPC78913
0.8993	High Similarity	NPC11566
0.8986	High Similarity	NPC294409
0.8986	High Similarity	NPC303644
0.8986	High Similarity	NPC162680
0.8986	High Similarity	NPC332594
0.8986	High Similarity	NPC7013
0.8986	High Similarity	NPC209560
0.8986	High Similarity	NPC259685
0.8986	High Similarity	NPC181124
0.8986	High Similarity	NPC116632
0.8978	High Similarity	NPC239495
0.8978	High Similarity	NPC46869
0.8978	High Similarity	NPC9985
0.8973	High Similarity	NPC186507
0.8971	High Similarity	NPC50898
0.8971	High Similarity	NPC78540
0.8971	High Similarity	NPC274121
0.8971	High Similarity	NPC57601
0.8971	High Similarity	NPC213216
0.8958	High Similarity	NPC469932
0.8958	High Similarity	NPC164299
0.8958	High Similarity	NPC88445
0.8951	High Similarity	NPC282335
0.8951	High Similarity	NPC249942
0.8951	High Similarity	NPC218300
0.8951	High Similarity	NPC297886
0.8947	High Similarity	NPC473907
0.8944	High Similarity	NPC234629
0.8944	High Similarity	NPC471590
0.8944	High Similarity	NPC311741
0.8944	High Similarity	NPC179970
0.8944	High Similarity	NPC171656
0.8936	High Similarity	NPC11561
0.8936	High Similarity	NPC202981
0.8936	High Similarity	NPC226636
0.8936	High Similarity	NPC473042
0.8936	High Similarity	NPC144499
0.8929	High Similarity	NPC269652
0.8929	High Similarity	NPC475680
0.8929	High Similarity	NPC235239
0.8929	High Similarity	NPC150522
0.8929	High Similarity	NPC281207
0.8929	High Similarity	NPC69769
0.8929	High Similarity	NPC241100
0.8929	High Similarity	NPC470856
0.8929	High Similarity	NPC472409
0.8929	High Similarity	NPC159275
0.8929	High Similarity	NPC305355
0.8921	High Similarity	NPC188947
0.8921	High Similarity	NPC99333
0.8921	High Similarity	NPC280284
0.8921	High Similarity	NPC12175
0.8921	High Similarity	NPC124269
0.8921	High Similarity	NPC276905
0.8921	High Similarity	NPC55162
0.8921	High Similarity	NPC278323
0.8921	High Similarity	NPC90665
0.8921	High Similarity	NPC279668
0.8921	High Similarity	NPC309154
0.8897	High Similarity	NPC229646
0.8897	High Similarity	NPC191104
0.8897	High Similarity	NPC473466
0.8897	High Similarity	NPC474735
0.8897	High Similarity	NPC151973
0.8897	High Similarity	NPC177839
0.8897	High Similarity	NPC295036
0.8897	High Similarity	NPC474660
0.8889	High Similarity	NPC266743
0.8889	High Similarity	NPC469933
0.8881	High Similarity	NPC473927
0.8881	High Similarity	NPC473894
0.8873	High Similarity	NPC293053
0.8873	High Similarity	NPC113089
0.8873	High Similarity	NPC9117
0.8873	High Similarity	NPC59522
0.8873	High Similarity	NPC38219
0.8873	High Similarity	NPC106985
0.8873	High Similarity	NPC190637
0.8873	High Similarity	NPC11700
0.8873	High Similarity	NPC18585
0.8873	High Similarity	NPC24821
0.8873	High Similarity	NPC219915
0.8873	High Similarity	NPC17262
0.8873	High Similarity	NPC212932
0.8873	High Similarity	NPC166138
0.8865	High Similarity	NPC282300
0.8865	High Similarity	NPC3188
0.8865	High Similarity	NPC136840
0.8865	High Similarity	NPC105648
0.8864	High Similarity	NPC2771
0.8857	High Similarity	NPC53181
0.8857	High Similarity	NPC143799
0.8857	High Similarity	NPC152042
0.8857	High Similarity	NPC217186
0.8857	High Similarity	NPC222342
0.8857	High Similarity	NPC265871
0.8857	High Similarity	NPC20709
0.8857	High Similarity	NPC274784
0.8857	High Similarity	NPC295384
0.8857	High Similarity	NPC150648
0.8857	High Similarity	NPC261234
0.8857	High Similarity	NPC241838
0.8857	High Similarity	NPC329203
0.8857	High Similarity	NPC310135
0.8857	High Similarity	NPC225153
0.8851	High Similarity	NPC474983
0.8849	High Similarity	NPC299379
0.8849	High Similarity	NPC290291
0.8849	High Similarity	NPC188879
0.8849	High Similarity	NPC275055

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 NPC103001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	449
0.1-0.2	979
0.2-0.3	1587
0.3-0.4	2693
0.4-0.5	1883
0.5-0.6	1064
0.6-0.7	327
0.7-0.8	105
0.8-0.85	41
0.85-0.9	16
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD2796	Approved
0.913	High Similarity	NPD1243	Approved
0.9118	High Similarity	NPD3748	Approved
0.8873	High Similarity	NPD6799	Approved
0.8841	High Similarity	NPD1510	Phase 2
0.8819	High Similarity	NPD920	Approved
0.8811	High Similarity	NPD4378	Clinical (unspecified phase)
0.8803	High Similarity	NPD643	Clinical (unspecified phase)
0.8794	High Similarity	NPD3750	Approved
0.8786	High Similarity	NPD1549	Phase 2
0.8716	High Similarity	NPD7819	Suspended
0.8716	High Similarity	NPD7096	Clinical (unspecified phase)
0.8714	High Similarity	NPD1552	Clinical (unspecified phase)
0.8714	High Similarity	NPD1550	Clinical (unspecified phase)
0.8707	High Similarity	NPD7411	Suspended
0.8686	High Similarity	NPD1240	Approved
0.8681	High Similarity	NPD7410	Clinical (unspecified phase)
0.8681	High Similarity	NPD642	Clinical (unspecified phase)
0.8649	High Similarity	NPD6801	Discontinued
0.8639	High Similarity	NPD6599	Discontinued
0.8561	High Similarity	NPD1607	Approved
0.8543	High Similarity	NPD7075	Discontinued
0.8543	High Similarity	NPD3749	Approved
0.8533	High Similarity	NPD3817	Phase 2
0.8529	High Similarity	NPD6832	Phase 2
0.8483	Intermediate Similarity	NPD1511	Approved
0.8444	Intermediate Similarity	NPD3267	Approved
0.8444	Intermediate Similarity	NPD3266	Approved
0.8425	Intermediate Similarity	NPD5401	Approved
0.8417	Intermediate Similarity	NPD4307	Phase 2
0.8406	Intermediate Similarity	NPD2313	Discontinued
0.8406	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1551	Phase 2
0.8367	Intermediate Similarity	NPD1512	Approved
0.8366	Intermediate Similarity	NPD919	Approved
0.8333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD5403	Approved
0.831	Intermediate Similarity	NPD2799	Discontinued
0.8309	Intermediate Similarity	NPD1203	Approved
0.8301	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD1934	Approved
0.8273	Intermediate Similarity	NPD1296	Phase 2
0.8267	Intermediate Similarity	NPD4380	Phase 2
0.8235	Intermediate Similarity	NPD7768	Phase 2
0.8227	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD2801	Approved
0.8222	Intermediate Similarity	NPD9717	Approved
0.8217	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4308	Phase 3
0.817	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD3268	Approved
0.8116	Intermediate Similarity	NPD2798	Approved
0.8099	Intermediate Similarity	NPD1933	Approved
0.8079	Intermediate Similarity	NPD3226	Approved
0.8077	Intermediate Similarity	NPD5494	Approved
0.8067	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD5402	Approved
0.8043	Intermediate Similarity	NPD2797	Approved
0.8015	Intermediate Similarity	NPD422	Phase 1
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD17	Approved
0.8	Intermediate Similarity	NPD3882	Suspended
0.7986	Intermediate Similarity	NPD1019	Discontinued
0.7971	Intermediate Similarity	NPD3225	Approved
0.7959	Intermediate Similarity	NPD2800	Approved
0.7945	Intermediate Similarity	NPD2346	Discontinued
0.7945	Intermediate Similarity	NPD2344	Approved
0.7935	Intermediate Similarity	NPD4288	Approved
0.7905	Intermediate Similarity	NPD4628	Phase 3
0.7888	Intermediate Similarity	NPD3818	Discontinued
0.7885	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD5953	Discontinued
0.784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1608	Approved
0.7812	Intermediate Similarity	NPD3926	Phase 2
0.7808	Intermediate Similarity	NPD7033	Discontinued
0.7799	Intermediate Similarity	NPD1247	Approved
0.7764	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD6166	Phase 2
0.7764	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD411	Approved
0.7756	Intermediate Similarity	NPD1465	Phase 2
0.775	Intermediate Similarity	NPD6232	Discontinued
0.7733	Intermediate Similarity	NPD2309	Approved
0.773	Intermediate Similarity	NPD7286	Phase 2
0.773	Intermediate Similarity	NPD5844	Phase 1
0.773	Intermediate Similarity	NPD7054	Approved
0.7724	Intermediate Similarity	NPD447	Suspended
0.7718	Intermediate Similarity	NPD2654	Approved
0.7716	Intermediate Similarity	NPD7473	Discontinued
0.7703	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2353	Approved
0.7698	Intermediate Similarity	NPD3972	Approved
0.7697	Intermediate Similarity	NPD2533	Approved
0.7697	Intermediate Similarity	NPD2534	Approved
0.7697	Intermediate Similarity	NPD2532	Approved
0.7688	Intermediate Similarity	NPD6959	Discontinued
0.7683	Intermediate Similarity	NPD7074	Phase 3
0.7683	Intermediate Similarity	NPD7472	Approved
0.7677	Intermediate Similarity	NPD6585	Discontinued
0.7669	Intermediate Similarity	NPD5535	Approved
0.7667	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD943	Approved
0.7654	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6797	Phase 2
0.7628	Intermediate Similarity	NPD5890	Approved
0.7628	Intermediate Similarity	NPD5889	Approved
0.7612	Intermediate Similarity	NPD1241	Discontinued
0.759	Intermediate Similarity	NPD6559	Discontinued
0.759	Intermediate Similarity	NPD7251	Discontinued
0.7584	Intermediate Similarity	NPD1471	Phase 3
0.7568	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6651	Approved
0.7545	Intermediate Similarity	NPD7808	Phase 3
0.7545	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6099	Approved
0.7517	Intermediate Similarity	NPD6100	Approved
0.7517	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD3887	Approved
0.75	Intermediate Similarity	NPD2354	Approved
0.7485	Intermediate Similarity	NPD4287	Approved
0.7483	Intermediate Similarity	NPD5124	Phase 1
0.7483	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1876	Approved
0.7464	Intermediate Similarity	NPD1548	Phase 1
0.7464	Intermediate Similarity	NPD9545	Approved
0.7455	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD9493	Approved
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6808	Phase 2
0.7405	Intermediate Similarity	NPD9697	Approved
0.7397	Intermediate Similarity	NPD6798	Discontinued
0.7379	Intermediate Similarity	NPD4908	Phase 1
0.7376	Intermediate Similarity	NPD1610	Phase 2
0.7365	Intermediate Similarity	NPD230	Phase 1
0.7355	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1164	Approved
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6971	Discontinued
0.7279	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD5242	Approved
0.7256	Intermediate Similarity	NPD7199	Phase 2
0.7255	Intermediate Similarity	NPD1652	Phase 2
0.7252	Intermediate Similarity	NPD9261	Approved
0.725	Intermediate Similarity	NPD6279	Approved
0.725	Intermediate Similarity	NPD6280	Approved
0.7248	Intermediate Similarity	NPD6355	Discontinued
0.723	Intermediate Similarity	NPD8032	Phase 2
0.7229	Intermediate Similarity	NPD2403	Approved
0.7214	Intermediate Similarity	NPD1894	Discontinued
0.7212	Intermediate Similarity	NPD7229	Phase 3
0.7208	Intermediate Similarity	NPD7003	Approved
0.7203	Intermediate Similarity	NPD1481	Phase 2
0.7197	Intermediate Similarity	NPD5049	Phase 3
0.7197	Intermediate Similarity	NPD6273	Approved
0.7188	Intermediate Similarity	NPD2366	Approved
0.7181	Intermediate Similarity	NPD3140	Approved
0.7181	Intermediate Similarity	NPD3142	Approved
0.7179	Intermediate Similarity	NPD7390	Discontinued
0.7171	Intermediate Similarity	NPD5408	Approved
0.7171	Intermediate Similarity	NPD5406	Approved
0.7171	Intermediate Similarity	NPD5404	Approved
0.7171	Intermediate Similarity	NPD5405	Approved
0.717	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2296	Approved
0.7143	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1535	Discovery
0.7133	Intermediate Similarity	NPD1281	Approved
0.7119	Intermediate Similarity	NPD4363	Phase 3
0.7119	Intermediate Similarity	NPD4360	Phase 2
0.7114	Intermediate Similarity	NPD6233	Phase 2
0.7108	Intermediate Similarity	NPD5710	Approved
0.7108	Intermediate Similarity	NPD5711	Approved
0.7089	Intermediate Similarity	NPD2186	Approved
0.7081	Intermediate Similarity	NPD6386	Approved
0.7081	Intermediate Similarity	NPD6385	Approved
0.7079	Intermediate Similarity	NPD4361	Phase 2
0.7079	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6104	Discontinued
0.7075	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4477	Approved
0.7059	Intermediate Similarity	NPD4476	Approved
0.7055	Intermediate Similarity	NPD1470	Approved
0.7055	Intermediate Similarity	NPD5353	Approved
0.7041	Intermediate Similarity	NPD3751	Discontinued
0.7037	Intermediate Similarity	NPD9264	Approved
0.7037	Intermediate Similarity	NPD9267	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