NPASS Compound

Structure

CID54503 OpenBabel06191715392D 21 22 0 0 0 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 1.7321 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -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 1.7321 -2.0000 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 -0.8660 -0.5000 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 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 9 1 0 0 0 0 2 9 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.12
Volume:	296.312
LogP:	2.356
LogD:	1.911
LogS:	-2.889
# Rotatable Bonds:	5
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.792
Synthetic Accessibility Score:	2.533
Fsp3:	0.375
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:	-4.665
MDCK Permeability:	2.2822496248409152e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.447

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.423
Plasma Protein Binding (PPB):	87.60171508789062%
Volume Distribution (VD):	0.915
Pgp-substrate:	12.127769470214844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.882
CYP1A2-substrate:	0.97
CYP2C19-inhibitor:	0.56
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.439
CYP2C9-substrate:	0.802
CYP2D6-inhibitor:	0.117
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.309
CYP3A4-substrate:	0.746

ADMET: Excretion

Clearance (CL):	11.078
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.907
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.76
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.242
Carcinogencity:	0.225
Eye Corrosion:	0.004
Eye Irritation:	0.023
Respiratory Toxicity:	0.712

Download Data

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

Natural Product: NPC54503

Natural Product ID:	NPC54503
*Common Name:**	5,7-Dimethoxy-8-(3-Methyl-2-Oxobutyl)-Coumarin
IUPAC Name:	5,7-dimethoxy-8-(3-methyl-2-oxobutyl)chromen-2-one
Synonyms:
Standard InCHIKey:	ISXFUPHLGNGMIC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18O5/c1-9(2)12(17)7-11-14(20-4)8-13(19-3)10-5-6-15(18)21-16(10)11/h5-6,8-9H,7H2,1-4H3
SMILES:	CC(C)C(=O)Cc1c(cc(c2ccc(=O)oc12)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426662
PubChem CID:	5316871
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354205]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354205]
NPO33003	murraya alata	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25621853]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8979	Strychnos malacoclados	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12008	Aplidium californicum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26235	Achillea ageratum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21159	Monoon membranifolium	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12370	Pulmonaria officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2715	Murraya paniculata	Species	Rutaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	20600.0	nM	PMID[508254]

☑ 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 NPC54503 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	429
0.1-0.2	1884
0.2-0.3	5127
0.3-0.4	10755
0.4-0.5	7094
0.5-0.6	4625
0.6-0.7	5885
0.7-0.8	4831
0.8-0.85	1516
0.85-0.9	392
0.9-0.95	138
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC55147
0.9474	High Similarity	NPC472515
0.9394	High Similarity	NPC472516
0.938	High Similarity	NPC472517
0.9365	High Similarity	NPC471828
0.9365	High Similarity	NPC471827
0.9308	High Similarity	NPC175159
0.9254	High Similarity	NPC36414
0.9191	High Similarity	NPC229916
0.9179	High Similarity	NPC253616
0.9173	High Similarity	NPC104796
0.9134	High Similarity	NPC201667
0.9134	High Similarity	NPC27671
0.9134	High Similarity	NPC73413
0.9104	High Similarity	NPC268081
0.9098	High Similarity	NPC229128
0.9098	High Similarity	NPC61499
0.9055	High Similarity	NPC109675
0.9055	High Similarity	NPC273772
0.9055	High Similarity	NPC472518
0.9048	High Similarity	NPC144418
0.9044	High Similarity	NPC183642
0.9044	High Similarity	NPC310370
0.9037	High Similarity	NPC221046
0.9037	High Similarity	NPC307883
0.9	High Similarity	NPC472519
0.8992	High Similarity	NPC471826
0.8976	High Similarity	NPC96286
0.8976	High Similarity	NPC248429
0.8921	High Similarity	NPC71739
0.8921	High Similarity	NPC295696
0.8905	High Similarity	NPC155552
0.8905	High Similarity	NPC473209
0.8889	High Similarity	NPC128529
0.8889	High Similarity	NPC177281
0.8889	High Similarity	NPC471630
0.8889	High Similarity	NPC160727
0.8889	High Similarity	NPC55615
0.8889	High Similarity	NPC283019
0.8889	High Similarity	NPC149320
0.8889	High Similarity	NPC476455
0.8855	High Similarity	NPC185066
0.8849	High Similarity	NPC251372
0.8832	High Similarity	NPC71903
0.8815	High Similarity	NPC472424
0.8815	High Similarity	NPC281241
0.8815	High Similarity	NPC66705
0.8815	High Similarity	NPC471909
0.8815	High Similarity	NPC86892
0.8815	High Similarity	NPC471625
0.8806	High Similarity	NPC222036
0.8806	High Similarity	NPC7526
0.8788	High Similarity	NPC474289
0.8788	High Similarity	NPC168710
0.8768	High Similarity	NPC136095
0.8768	High Similarity	NPC170812
0.876	High Similarity	NPC154176
0.876	High Similarity	NPC290605
0.876	High Similarity	NPC173350
0.8759	High Similarity	NPC327612
0.8759	High Similarity	NPC38153
0.8759	High Similarity	NPC103001
0.8759	High Similarity	NPC332594
0.8759	High Similarity	NPC73078
0.8759	High Similarity	NPC148738
0.8759	High Similarity	NPC319870
0.875	High Similarity	NPC283331
0.8741	High Similarity	NPC267412
0.8741	High Similarity	NPC287182
0.8741	High Similarity	NPC47163
0.8741	High Similarity	NPC195343
0.8741	High Similarity	NPC74655
0.8741	High Similarity	NPC319859
0.8741	High Similarity	NPC55149
0.8741	High Similarity	NPC84894
0.8741	High Similarity	NPC164269
0.8741	High Similarity	NPC127888
0.8741	High Similarity	NPC18804
0.8741	High Similarity	NPC198381
0.8741	High Similarity	NPC166672
0.8741	High Similarity	NPC100986
0.8741	High Similarity	NPC260265
0.8741	High Similarity	NPC307412
0.8731	High Similarity	NPC14248
0.8731	High Similarity	NPC119985
0.8731	High Similarity	NPC280476
0.8722	High Similarity	NPC80170
0.8712	High Similarity	NPC157212
0.8712	High Similarity	NPC199204
0.8705	High Similarity	NPC470856
0.8702	High Similarity	NPC188327
0.8702	High Similarity	NPC234109
0.8692	High Similarity	NPC291899
0.8692	High Similarity	NPC111347
0.8686	High Similarity	NPC471069
0.8686	High Similarity	NPC471068
0.8682	High Similarity	NPC150214
0.8681	High Similarity	NPC191104
0.8672	High Similarity	NPC163200
0.8672	High Similarity	NPC235190
0.8672	High Similarity	NPC180006
0.8671	High Similarity	NPC146388
0.8667	High Similarity	NPC318400
0.8667	High Similarity	NPC167111
0.8667	High Similarity	NPC207002
0.8667	High Similarity	NPC31849
0.8667	High Similarity	NPC229646
0.8667	High Similarity	NPC471910
0.8667	High Similarity	NPC133956
0.8667	High Similarity	NPC296624
0.8662	High Similarity	NPC470322
0.8662	High Similarity	NPC154217
0.8661	High Similarity	NPC298796
0.8643	High Similarity	NPC254010
0.8636	High Similarity	NPC243688
0.8636	High Similarity	NPC37512
0.8636	High Similarity	NPC289316
0.8633	High Similarity	NPC472523
0.8623	High Similarity	NPC471070
0.8623	High Similarity	NPC471071
0.8623	High Similarity	NPC471072
0.8615	High Similarity	NPC50720
0.8615	High Similarity	NPC315807
0.8613	High Similarity	NPC223616
0.8613	High Similarity	NPC246177
0.8613	High Similarity	NPC46869
0.8613	High Similarity	NPC317045
0.8611	High Similarity	NPC146014
0.8611	High Similarity	NPC103116
0.8611	High Similarity	NPC88445
0.8603	High Similarity	NPC180716
0.8603	High Similarity	NPC224475
0.8603	High Similarity	NPC213173
0.8601	High Similarity	NPC304443
0.8601	High Similarity	NPC74539
0.8593	High Similarity	NPC19157
0.8592	High Similarity	NPC208584
0.8592	High Similarity	NPC171656
0.8592	High Similarity	NPC196137
0.8592	High Similarity	NPC294365
0.8592	High Similarity	NPC1886
0.8583	High Similarity	NPC152306
0.8583	High Similarity	NPC265547
0.8583	High Similarity	NPC96705
0.8582	High Similarity	NPC313036
0.8561	High Similarity	NPC163248
0.8561	High Similarity	NPC183639
0.8561	High Similarity	NPC199458
0.8551	High Similarity	NPC254741
0.8551	High Similarity	NPC309452
0.8551	High Similarity	NPC161196
0.8551	High Similarity	NPC155963
0.854	High Similarity	NPC472525
0.854	High Similarity	NPC469675
0.8538	High Similarity	NPC13007
0.8538	High Similarity	NPC257188
0.8531	High Similarity	NPC181388
0.8521	High Similarity	NPC76657
0.8521	High Similarity	NPC112791
0.8521	High Similarity	NPC196459
0.8521	High Similarity	NPC188632
0.8521	High Similarity	NPC470296
0.8521	High Similarity	NPC87609
0.8521	High Similarity	NPC94794
0.8519	High Similarity	NPC196979
0.8519	High Similarity	NPC470977
0.8519	High Similarity	NPC470976
0.8516	High Similarity	NPC281356
0.8511	High Similarity	NPC201820
0.8511	High Similarity	NPC24075
0.8507	High Similarity	NPC473894
0.85	High Similarity	NPC241975
0.85	High Similarity	NPC262635
0.85	High Similarity	NPC19476
0.85	High Similarity	NPC287286
0.8493	Intermediate Similarity	NPC189773
0.8489	Intermediate Similarity	NPC474624
0.8489	Intermediate Similarity	NPC211110
0.8489	Intermediate Similarity	NPC138047
0.8489	Intermediate Similarity	NPC151946
0.8489	Intermediate Similarity	NPC131782
0.8485	Intermediate Similarity	NPC244495
0.8485	Intermediate Similarity	NPC202594
0.8485	Intermediate Similarity	NPC93219
0.8485	Intermediate Similarity	NPC165556
0.8485	Intermediate Similarity	NPC232692
0.8478	Intermediate Similarity	NPC38099
0.8478	Intermediate Similarity	NPC26954
0.8473	Intermediate Similarity	NPC143725
0.8472	Intermediate Similarity	NPC218300
0.8472	Intermediate Similarity	NPC282335
0.8472	Intermediate Similarity	NPC142863
0.8472	Intermediate Similarity	NPC243154
0.8467	Intermediate Similarity	NPC204353
0.8467	Intermediate Similarity	NPC50896
0.8467	Intermediate Similarity	NPC292998
0.8467	Intermediate Similarity	NPC62366
0.8467	Intermediate Similarity	NPC326600
0.8462	Intermediate Similarity	NPC178627
0.8462	Intermediate Similarity	NPC179970

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 NPC54503 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	984
0.2-0.3	1833
0.3-0.4	2700
0.4-0.5	1811
0.5-0.6	977
0.6-0.7	312
0.7-0.8	99
0.8-0.85	34
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8613	High Similarity	NPD3748	Approved
0.8601	High Similarity	NPD920	Approved
0.85	High Similarity	NPD1243	Approved
0.8444	Intermediate Similarity	NPD1296	Phase 2
0.8417	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD3750	Approved
0.8309	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD2799	Discontinued
0.8209	Intermediate Similarity	NPD3266	Approved
0.8209	Intermediate Similarity	NPD3267	Approved
0.8207	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD6801	Discontinued
0.8182	Intermediate Similarity	NPD422	Phase 1
0.8138	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7819	Suspended
0.8129	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD5124	Phase 1
0.8121	Intermediate Similarity	NPD7411	Suspended
0.8112	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD2797	Approved
0.8056	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD3268	Approved
0.8029	Intermediate Similarity	NPD6832	Phase 2
0.8029	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD7075	Discontinued
0.7959	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6599	Discontinued
0.7931	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4307	Phase 2
0.7922	Intermediate Similarity	NPD919	Approved
0.7917	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2313	Discontinued
0.7908	Intermediate Similarity	NPD7768	Phase 2
0.7907	Intermediate Similarity	NPD1241	Discontinued
0.7832	Intermediate Similarity	NPD1510	Phase 2
0.7801	Intermediate Similarity	NPD1240	Approved
0.7793	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD1551	Phase 2
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7763	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD17	Approved
0.7756	Intermediate Similarity	NPD5494	Approved
0.774	Intermediate Similarity	NPD2800	Approved
0.7733	Intermediate Similarity	NPD5403	Approved
0.7727	Intermediate Similarity	NPD3817	Phase 2
0.7727	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD9717	Approved
0.7718	Intermediate Similarity	NPD5401	Approved
0.7708	Intermediate Similarity	NPD4308	Phase 3
0.7697	Intermediate Similarity	NPD4380	Phase 2
0.7692	Intermediate Similarity	NPD1607	Approved
0.7673	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3749	Approved
0.7626	Intermediate Similarity	NPD1019	Discontinued
0.7622	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD5402	Approved
0.7609	Intermediate Similarity	NPD3225	Approved
0.7603	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2532	Approved
0.76	Intermediate Similarity	NPD2534	Approved
0.76	Intermediate Similarity	NPD2533	Approved
0.7591	Intermediate Similarity	NPD1608	Approved
0.7569	Intermediate Similarity	NPD6651	Approved
0.7568	Intermediate Similarity	NPD4628	Phase 3
0.7564	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD9697	Approved
0.7557	Intermediate Similarity	NPD5535	Approved
0.7556	Intermediate Similarity	NPD5691	Approved
0.7554	Intermediate Similarity	NPD1203	Approved
0.7548	Intermediate Similarity	NPD2801	Approved
0.7546	Intermediate Similarity	NPD5953	Discontinued
0.7531	Intermediate Similarity	NPD7286	Phase 2
0.7531	Intermediate Similarity	NPD5844	Phase 1
0.7518	Intermediate Similarity	NPD1281	Approved
0.7518	Intermediate Similarity	NPD4908	Phase 1
0.7516	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD3134	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD4288	Approved
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7484	Intermediate Similarity	NPD1247	Approved
0.7483	Intermediate Similarity	NPD8032	Phase 2
0.7483	Intermediate Similarity	NPD6002	Phase 3
0.7483	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6005	Phase 3
0.7483	Intermediate Similarity	NPD2346	Discontinued
0.7483	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6004	Phase 3
0.7452	Intermediate Similarity	NPD3882	Suspended
0.7438	Intermediate Similarity	NPD7229	Phase 3
0.7431	Intermediate Similarity	NPD2979	Phase 3
0.7417	Intermediate Similarity	NPD1511	Approved
0.7415	Intermediate Similarity	NPD4476	Approved
0.7415	Intermediate Similarity	NPD6100	Approved
0.7415	Intermediate Similarity	NPD6099	Approved
0.7415	Intermediate Similarity	NPD4477	Approved
0.7413	Intermediate Similarity	NPD6798	Discontinued
0.7407	Intermediate Similarity	NPD7473	Discontinued
0.7391	Intermediate Similarity	NPD1610	Phase 2
0.7391	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD447	Suspended
0.7379	Intermediate Similarity	NPD1933	Approved
0.7372	Intermediate Similarity	NPD1934	Approved
0.7372	Intermediate Similarity	NPD4626	Approved
0.7357	Intermediate Similarity	NPD1876	Approved
0.7357	Intermediate Similarity	NPD1283	Approved
0.7353	Intermediate Similarity	NPD1548	Phase 1
0.7347	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD3972	Approved
0.7333	Intermediate Similarity	NPD7003	Approved
0.7329	Intermediate Similarity	NPD6232	Discontinued
0.7325	Intermediate Similarity	NPD1465	Phase 2
0.732	Intermediate Similarity	NPD1512	Approved
0.7317	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2424	Discontinued
0.7308	Intermediate Similarity	NPD1358	Approved
0.7303	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1651	Approved
0.7297	Intermediate Similarity	NPD2438	Suspended
0.7296	Intermediate Similarity	NPD6971	Discontinued
0.7292	Intermediate Similarity	NPD411	Approved
0.729	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6559	Discontinued
0.7284	Intermediate Similarity	NPD3926	Phase 2
0.7273	Intermediate Similarity	NPD2614	Approved
0.7267	Intermediate Similarity	NPD6959	Discontinued
0.7267	Intermediate Similarity	NPD2654	Approved
0.726	Intermediate Similarity	NPD4622	Approved
0.726	Intermediate Similarity	NPD230	Phase 1
0.726	Intermediate Similarity	NPD4618	Approved
0.7256	Intermediate Similarity	NPD3818	Discontinued
0.7255	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1778	Approved
0.7226	Intermediate Similarity	NPD9545	Approved
0.7226	Intermediate Similarity	NPD1894	Discontinued
0.7208	Intermediate Similarity	NPD5049	Phase 3
0.7208	Intermediate Similarity	NPD6273	Approved
0.7197	Intermediate Similarity	NPD5890	Approved
0.7197	Intermediate Similarity	NPD5889	Approved
0.7194	Intermediate Similarity	NPD3496	Discontinued
0.7192	Intermediate Similarity	NPD4060	Phase 1
0.7181	Intermediate Similarity	NPD2531	Phase 2
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7179	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5585	Approved
0.7172	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3764	Approved
0.7171	Intermediate Similarity	NPD3887	Approved
0.717	Intermediate Similarity	NPD5353	Approved
0.7163	Intermediate Similarity	NPD4749	Approved
0.7162	Intermediate Similarity	NPD5688	Approved
0.7162	Intermediate Similarity	NPD5689	Approved
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD37	Approved
0.7152	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1611	Approved
0.7134	Intermediate Similarity	NPD6585	Discontinued
0.7134	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2403	Approved
0.7133	Intermediate Similarity	NPD2344	Approved
0.7133	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2353	Approved
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4965	Approved
0.7125	Intermediate Similarity	NPD4967	Phase 2
0.7125	Intermediate Similarity	NPD4966	Approved
0.7124	Intermediate Similarity	NPD6667	Approved
0.7124	Intermediate Similarity	NPD6666	Approved
0.7124	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6233	Phase 2
0.7115	Intermediate Similarity	NPD1653	Approved
0.7107	Intermediate Similarity	NPD8455	Phase 2
0.7103	Intermediate Similarity	NPD4625	Phase 3
0.7097	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1481	Phase 2
0.708	Intermediate Similarity	NPD9493	Approved
0.7078	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3140	Approved
0.7075	Intermediate Similarity	NPD3142	Approved
0.7073	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5242	Approved
0.7071	Intermediate Similarity	NPD3847	Discontinued
0.7055	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7097	Phase 1
0.7041	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6234	Discontinued
0.703	Intermediate Similarity	NPD6166	Phase 2
0.703	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6168	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