NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	279.016
LogP:	1.344
LogD:	1.45
LogS:	-3.144
# Rotatable Bonds:	4
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.682
Synthetic Accessibility Score:	2.989
Fsp3:	0.333
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:	-4.793
MDCK Permeability:	2.5231342078768648e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	82.57508087158203%
Volume Distribution (VD):	0.824
Pgp-substrate:	11.527559280395508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.858
CYP1A2-substrate:	0.883
CYP2C19-inhibitor:	0.284
CYP2C19-substrate:	0.416
CYP2C9-inhibitor:	0.348
CYP2C9-substrate:	0.697
CYP2D6-inhibitor:	0.269
CYP2D6-substrate:	0.644
CYP3A4-inhibitor:	0.233
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	9.977
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.73
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.158
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.118
Carcinogencity:	0.859
Eye Corrosion:	0.003
Eye Irritation:	0.051
Respiratory Toxicity:	0.615

Download Data

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

Natural Product: NPC229916

Natural Product ID:	NPC229916
*Common Name:**	Murranganone
IUPAC Name:	8-(1-hydroxy-3-methyl-2-oxobutyl)-7-methoxychromen-2-one
Synonyms:
Standard InCHIKey:	QPXQLCIYAJVXPH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-8(2)13(17)14(18)12-10(19-3)6-4-9-5-7-11(16)20-15(9)12/h4-8,14,18H,1-3H3
SMILES:	COc1ccc2c(c1C(C(=O)C(C)C)O)oc(=O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426684
PubChem CID:	5319956
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]
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	=	12400.0	nM	PMID[478454]

☑ 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 NPC229916 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	355
0.1-0.2	1565
0.2-0.3	3897
0.3-0.4	8913
0.4-0.5	9783
0.5-0.6	4109
0.6-0.7	5945
0.7-0.8	5083
0.8-0.85	2145
0.85-0.9	754
0.9-0.95	142
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9416	High Similarity	NPC221046
0.9333	High Similarity	NPC55147
0.9191	High Similarity	NPC54503
0.9051	High Similarity	NPC31849
0.9007	High Similarity	NPC310370
0.9007	High Similarity	NPC183642
0.8993	High Similarity	NPC104796
0.8986	High Similarity	NPC204353
0.8986	High Similarity	NPC326600
0.8986	High Similarity	NPC50896
0.8978	High Similarity	NPC194277
0.8978	High Similarity	NPC175159
0.8929	High Similarity	NPC309452
0.8929	High Similarity	NPC472516
0.8905	High Similarity	NPC472517
0.8904	High Similarity	NPC146388
0.8889	High Similarity	NPC71739
0.8889	High Similarity	NPC295696
0.8873	High Similarity	NPC155552
0.8865	High Similarity	NPC332594
0.8865	High Similarity	NPC151946
0.8857	High Similarity	NPC26954
0.8857	High Similarity	NPC38099
0.8849	High Similarity	NPC62366
0.8844	High Similarity	NPC103116
0.8844	High Similarity	NPC146014
0.8824	High Similarity	NPC185066
0.8803	High Similarity	NPC36414
0.8803	High Similarity	NPC71903
0.8794	High Similarity	NPC471069
0.8794	High Similarity	NPC471068
0.8794	High Similarity	NPC155963
0.8786	High Similarity	NPC61499
0.8784	High Similarity	NPC474735
0.8777	High Similarity	NPC163557
0.8759	High Similarity	NPC168710
0.8759	High Similarity	NPC474939
0.8759	High Similarity	NPC470909
0.8759	High Similarity	NPC96216
0.8759	High Similarity	NPC474289
0.875	High Similarity	NPC224774
0.875	High Similarity	NPC121740
0.875	High Similarity	NPC258567
0.8741	High Similarity	NPC152771
0.8741	High Similarity	NPC287286
0.8741	High Similarity	NPC170812
0.8741	High Similarity	NPC195357
0.8741	High Similarity	NPC472515
0.8732	High Similarity	NPC327612
0.8732	High Similarity	NPC73078
0.8732	High Similarity	NPC211110
0.8732	High Similarity	NPC148738
0.8732	High Similarity	NPC471071
0.8732	High Similarity	NPC319870
0.8732	High Similarity	NPC279573
0.8732	High Similarity	NPC471070
0.8732	High Similarity	NPC471072
0.8723	High Similarity	NPC266245
0.8714	High Similarity	NPC224475
0.8714	High Similarity	NPC213173
0.8714	High Similarity	NPC180716
0.8699	High Similarity	NPC118059
0.8699	High Similarity	NPC470554
0.8699	High Similarity	NPC133060
0.8699	High Similarity	NPC288910
0.869	High Similarity	NPC162476
0.869	High Similarity	NPC470556
0.869	High Similarity	NPC294432
0.8686	High Similarity	NPC469453
0.8684	High Similarity	NPC269495
0.8671	High Similarity	NPC312881
0.8662	High Similarity	NPC184861
0.8662	High Similarity	NPC294456
0.8662	High Similarity	NPC232246
0.8662	High Similarity	NPC212124
0.8662	High Similarity	NPC225106
0.8662	High Similarity	NPC281014
0.8662	High Similarity	NPC153818
0.8658	High Similarity	NPC61258
0.8652	High Similarity	NPC472525
0.8639	High Similarity	NPC470910
0.8639	High Similarity	NPC470322
0.8639	High Similarity	NPC154217
0.863	High Similarity	NPC76657
0.863	High Similarity	NPC470553
0.863	High Similarity	NPC184738
0.863	High Similarity	NPC307895
0.863	High Similarity	NPC33653
0.8613	High Similarity	NPC243688
0.8611	High Similarity	NPC139554
0.8603	High Similarity	NPC471828
0.8603	High Similarity	NPC471827
0.8603	High Similarity	NPC93219
0.8603	High Similarity	NPC244495
0.8601	High Similarity	NPC307883
0.8601	High Similarity	NPC253616
0.86	High Similarity	NPC290671
0.8593	High Similarity	NPC472518
0.8592	High Similarity	NPC246177
0.8592	High Similarity	NPC177281
0.8592	High Similarity	NPC223616
0.8592	High Similarity	NPC471630
0.8592	High Similarity	NPC149320
0.8592	High Similarity	NPC188380
0.8592	High Similarity	NPC55615
0.8592	High Similarity	NPC128529
0.8592	High Similarity	NPC317045
0.8592	High Similarity	NPC224543
0.8592	High Similarity	NPC160727
0.8592	High Similarity	NPC78746
0.8592	High Similarity	NPC476455
0.8592	High Similarity	NPC283019
0.8591	High Similarity	NPC470461
0.8591	High Similarity	NPC19238
0.8582	High Similarity	NPC98179
0.8582	High Similarity	NPC253574
0.8581	High Similarity	NPC285748
0.8581	High Similarity	NPC177995
0.8581	High Similarity	NPC474108
0.8571	High Similarity	NPC119985
0.8571	High Similarity	NPC280476
0.8571	High Similarity	NPC307289
0.8571	High Similarity	NPC196137
0.8571	High Similarity	NPC1886
0.8562	High Similarity	NPC112829
0.8561	High Similarity	NPC80170
0.8561	High Similarity	NPC113098
0.8552	High Similarity	NPC470856
0.8551	High Similarity	NPC472519
0.8551	High Similarity	NPC199204
0.8543	High Similarity	NPC256141
0.8542	High Similarity	NPC183639
0.8542	High Similarity	NPC199458
0.854	High Similarity	NPC234109
0.854	High Similarity	NPC188327
0.8533	High Similarity	NPC180351
0.8531	High Similarity	NPC268081
0.8531	High Similarity	NPC131198
0.8529	High Similarity	NPC27671
0.8529	High Similarity	NPC201667
0.8529	High Similarity	NPC73413
0.8523	High Similarity	NPC470460
0.8521	High Similarity	NPC229128
0.8521	High Similarity	NPC281241
0.8521	High Similarity	NPC86892
0.8521	High Similarity	NPC471909
0.8521	High Similarity	NPC472424
0.8521	High Similarity	NPC33986
0.8521	High Similarity	NPC471625
0.8519	High Similarity	NPC96286
0.8519	High Similarity	NPC248429
0.8514	High Similarity	NPC181388
0.8511	High Similarity	NPC205797
0.8511	High Similarity	NPC291551
0.8511	High Similarity	NPC241165
0.8511	High Similarity	NPC469965
0.8511	High Similarity	NPC142563
0.8511	High Similarity	NPC141822
0.8511	High Similarity	NPC222036
0.8511	High Similarity	NPC7526
0.8511	High Similarity	NPC1220
0.8503	High Similarity	NPC301751
0.8503	High Similarity	NPC105381
0.8503	High Similarity	NPC245482
0.8503	High Similarity	NPC188632
0.8503	High Similarity	NPC470296
0.8503	High Similarity	NPC112791
0.8503	High Similarity	NPC196459
0.8503	High Similarity	NPC10302
0.8503	High Similarity	NPC87609
0.8503	High Similarity	NPC94794
0.8503	High Similarity	NPC469701
0.85	High Similarity	NPC272650
0.85	High Similarity	NPC267336
0.85	High Similarity	NPC29734
0.8483	Intermediate Similarity	NPC138149
0.8483	Intermediate Similarity	NPC37206
0.8483	Intermediate Similarity	NPC23257
0.8483	Intermediate Similarity	NPC19476
0.8483	Intermediate Similarity	NPC241975
0.8477	Intermediate Similarity	NPC209142
0.8477	Intermediate Similarity	NPC312549
0.8472	Intermediate Similarity	NPC37428
0.8472	Intermediate Similarity	NPC131782
0.8472	Intermediate Similarity	NPC35501
0.8472	Intermediate Similarity	NPC474624
0.8472	Intermediate Similarity	NPC138047
0.8472	Intermediate Similarity	NPC278600
0.8472	Intermediate Similarity	NPC144512
0.8472	Intermediate Similarity	NPC137262
0.8472	Intermediate Similarity	NPC47040
0.8467	Intermediate Similarity	NPC164205
0.8467	Intermediate Similarity	NPC317492
0.8467	Intermediate Similarity	NPC104236
0.8462	Intermediate Similarity	NPC283331
0.8462	Intermediate Similarity	NPC60667
0.8456	Intermediate Similarity	NPC66991
0.8456	Intermediate Similarity	NPC109675
0.8456	Intermediate Similarity	NPC273772
0.8456	Intermediate Similarity	NPC142863

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 NPC229916 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	952
0.2-0.3	1746
0.3-0.4	2569
0.4-0.5	1943
0.5-0.6	1078
0.6-0.7	359
0.7-0.8	125
0.8-0.85	39
0.85-0.9	14
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8543	High Similarity	NPD6801	Discontinued
0.8511	High Similarity	NPD5123	Clinical (unspecified phase)
0.8511	High Similarity	NPD5124	Phase 1
0.8487	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD7075	Discontinued
0.8309	Intermediate Similarity	NPD422	Phase 1
0.8299	Intermediate Similarity	NPD3750	Approved
0.8298	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6799	Approved
0.8235	Intermediate Similarity	NPD7411	Suspended
0.8231	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD920	Approved
0.8212	Intermediate Similarity	NPD5403	Approved
0.8176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1549	Phase 2
0.8151	Intermediate Similarity	NPD2796	Approved
0.8129	Intermediate Similarity	NPD7819	Suspended
0.8108	Intermediate Similarity	NPD1243	Approved
0.8095	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD3748	Approved
0.8082	Intermediate Similarity	NPD1510	Phase 2
0.8082	Intermediate Similarity	NPD2799	Discontinued
0.8079	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD5401	Approved
0.8077	Intermediate Similarity	NPD5402	Approved
0.8071	Intermediate Similarity	NPD2797	Approved
0.8067	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD6599	Discontinued
0.8052	Intermediate Similarity	NPD4380	Phase 2
0.8042	Intermediate Similarity	NPD1296	Phase 2
0.8042	Intermediate Similarity	NPD3268	Approved
0.8041	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD1551	Phase 2
0.8025	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD4628	Phase 3
0.7931	Intermediate Similarity	NPD1240	Approved
0.7925	Intermediate Similarity	NPD919	Approved
0.7898	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD6355	Discontinued
0.7867	Intermediate Similarity	NPD1652	Phase 2
0.7866	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5844	Phase 1
0.7862	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD9717	Approved
0.7852	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6005	Phase 3
0.7852	Intermediate Similarity	NPD6002	Phase 3
0.7852	Intermediate Similarity	NPD6004	Phase 3
0.7852	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3817	Phase 2
0.7823	Intermediate Similarity	NPD1607	Approved
0.7799	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3882	Suspended
0.7793	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6798	Discontinued
0.7793	Intermediate Similarity	NPD2313	Discontinued
0.7791	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7727	Intermediate Similarity	NPD2534	Approved
0.7727	Intermediate Similarity	NPD2532	Approved
0.7727	Intermediate Similarity	NPD2533	Approved
0.7718	Intermediate Similarity	NPD4308	Phase 3
0.7718	Intermediate Similarity	NPD7033	Discontinued
0.7692	Intermediate Similarity	NPD3267	Approved
0.7692	Intermediate Similarity	NPD3266	Approved
0.7692	Intermediate Similarity	NPD1203	Approved
0.7677	Intermediate Similarity	NPD1512	Approved
0.7665	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5953	Discontinued
0.766	Intermediate Similarity	NPD1610	Phase 2
0.7655	Intermediate Similarity	NPD6832	Phase 2
0.7655	Intermediate Similarity	NPD4908	Phase 1
0.7655	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1241	Discontinued
0.7643	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3749	Approved
0.7632	Intermediate Similarity	NPD2800	Approved
0.7626	Intermediate Similarity	NPD1548	Phase 1
0.7622	Intermediate Similarity	NPD3225	Approved
0.7619	Intermediate Similarity	NPD6559	Discontinued
0.7616	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1934	Approved
0.7606	Intermediate Similarity	NPD1608	Approved
0.759	Intermediate Similarity	NPD3818	Discontinued
0.758	Intermediate Similarity	NPD1653	Approved
0.7576	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6166	Phase 2
0.7576	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4060	Phase 1
0.7566	Intermediate Similarity	NPD2424	Discontinued
0.7562	Intermediate Similarity	NPD2801	Approved
0.7548	Intermediate Similarity	NPD1511	Approved
0.7546	Intermediate Similarity	NPD5494	Approved
0.7545	Intermediate Similarity	NPD7286	Phase 2
0.7532	Intermediate Similarity	NPD3226	Approved
0.7517	Intermediate Similarity	NPD230	Phase 1
0.7517	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD9545	Approved
0.7469	Intermediate Similarity	NPD4965	Approved
0.7469	Intermediate Similarity	NPD4967	Phase 2
0.7469	Intermediate Similarity	NPD4966	Approved
0.7467	Intermediate Similarity	NPD6651	Approved
0.7456	Intermediate Similarity	NPD6797	Phase 2
0.7455	Intermediate Similarity	NPD7229	Phase 3
0.7452	Intermediate Similarity	NPD6273	Approved
0.745	Intermediate Similarity	NPD4307	Phase 2
0.7434	Intermediate Similarity	NPD4476	Approved
0.7434	Intermediate Similarity	NPD6100	Approved
0.7434	Intermediate Similarity	NPD6099	Approved
0.7434	Intermediate Similarity	NPD4477	Approved
0.7432	Intermediate Similarity	NPD411	Approved
0.7425	Intermediate Similarity	NPD7473	Discontinued
0.7412	Intermediate Similarity	NPD7251	Discontinued
0.7407	Intermediate Similarity	NPD4288	Approved
0.7397	Intermediate Similarity	NPD1019	Discontinued
0.7394	Intermediate Similarity	NPD1778	Approved
0.7394	Intermediate Similarity	NPD6959	Discontinued
0.7394	Intermediate Similarity	NPD17	Approved
0.7386	Intermediate Similarity	NPD2346	Discontinued
0.7383	Intermediate Similarity	NPD4062	Phase 3
0.7379	Intermediate Similarity	NPD1283	Approved
0.7372	Intermediate Similarity	NPD6667	Approved
0.7372	Intermediate Similarity	NPD6666	Approved
0.7368	Intermediate Similarity	NPD7808	Phase 3
0.7368	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7003	Approved
0.7349	Intermediate Similarity	NPD6232	Discontinued
0.7346	Intermediate Similarity	NPD1465	Phase 2
0.7346	Intermediate Similarity	NPD8455	Phase 2
0.7342	Intermediate Similarity	NPD5049	Phase 3
0.7337	Intermediate Similarity	NPD7054	Approved
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1613	Approved
0.7315	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7458	Discontinued
0.7305	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7472	Approved
0.7294	Intermediate Similarity	NPD7074	Phase 3
0.7292	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7199	Phase 2
0.7285	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2798	Approved
0.7279	Intermediate Similarity	NPD5647	Approved
0.7273	Intermediate Similarity	NPD6234	Discontinued
0.7273	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD5763	Approved
0.7273	Intermediate Similarity	NPD5762	Approved
0.7254	Intermediate Similarity	NPD1894	Discontinued
0.7241	Intermediate Similarity	NPD1481	Phase 2
0.7234	Intermediate Similarity	NPD9493	Approved
0.7222	Intermediate Similarity	NPD3496	Discontinued
0.7212	Intermediate Similarity	NPD6971	Discontinued
0.7203	Intermediate Similarity	NPD5691	Approved
0.72	Intermediate Similarity	NPD3764	Approved
0.72	Intermediate Similarity	NPD8434	Phase 2
0.7197	Intermediate Similarity	NPD6190	Approved
0.7197	Intermediate Similarity	NPD3887	Approved
0.7192	Intermediate Similarity	NPD4749	Approved
0.719	Intermediate Similarity	NPD7097	Phase 1
0.7188	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD8127	Discontinued
0.7185	Intermediate Similarity	NPD9697	Approved
0.7181	Intermediate Similarity	NPD2614	Approved
0.7176	Intermediate Similarity	NPD3751	Discontinued
0.7172	Intermediate Similarity	NPD1535	Discovery
0.7172	Intermediate Similarity	NPD1281	Approved
0.7172	Intermediate Similarity	NPD1091	Approved
0.7171	Intermediate Similarity	NPD4340	Discontinued
0.7162	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2344	Approved
0.716	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3027	Phase 3
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7132	Intermediate Similarity	NPD3134	Approved
0.7126	Intermediate Similarity	NPD8313	Approved
0.7126	Intermediate Similarity	NPD8312	Approved
0.7115	Intermediate Similarity	NPD5958	Discontinued
0.7115	Intermediate Similarity	NPD4534	Discontinued
0.7107	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4140	Approved
0.7105	Intermediate Similarity	NPD2979	Phase 3
0.7101	Intermediate Similarity	NPD3926	Phase 2
0.7097	Intermediate Similarity	NPD2438	Suspended

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