NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	276.379
LogP:	1.804
LogD:	1.927
LogS:	-3.927
# Rotatable Bonds:	4
TPSA:	73.58
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	2.569
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.61
MDCK Permeability:	3.62091523129493e-05
Pgp-inhibitor:	0.093
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	89.93020629882812%
Volume Distribution (VD):	0.532
Pgp-substrate:	3.8888468742370605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.556
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.47
CYP2C9-substrate:	0.642
CYP2D6-inhibitor:	0.635
CYP2D6-substrate:	0.603
CYP3A4-inhibitor:	0.546
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	9.176
Half-life (T1/2):	0.535

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.671
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.576
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.135
Carcinogencity:	0.931
Eye Corrosion:	0.006
Eye Irritation:	0.112
Respiratory Toxicity:	0.546

Download Data

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

Natural Product: NPC472516

Natural Product ID:	NPC472516
*Common Name:**	DLRWWSBVTODTKM-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DLRWWSBVTODTKM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O5/c1-8(2)13(17)14(18)12-10(19-3)6-4-9-5-7-11(16)20-15(9)12/h4-8H,1-3H3
SMILES:	CC(C)C(=O)C(=O)C1=C(C=CC2=C1OC(=O)C=C2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426669
PubChem CID:	n.a.
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
NPO33003	murraya alata	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25621853]

☑ 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	=	30500.0	nM	PMID[450704]

☑ 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 NPC472516 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	434
0.1-0.2	1844
0.2-0.3	4982
0.3-0.4	10597
0.4-0.5	7348
0.5-0.6	4566
0.6-0.7	5867
0.7-0.8	4833
0.8-0.85	1545
0.85-0.9	498
0.9-0.95	161
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9699	High Similarity	NPC36414
0.9627	High Similarity	NPC472515
0.9542	High Similarity	NPC55147
0.9478	High Similarity	NPC253616
0.9403	High Similarity	NPC268081
0.9394	High Similarity	NPC54503
0.9333	High Similarity	NPC332594
0.9203	High Similarity	NPC254010
0.9197	High Similarity	NPC136095
0.9197	High Similarity	NPC473209
0.9191	High Similarity	NPC103001
0.9173	High Similarity	NPC175159
0.9137	High Similarity	NPC313036
0.913	High Similarity	NPC470856
0.9111	High Similarity	NPC66705
0.9104	High Similarity	NPC229646
0.9098	High Similarity	NPC472517
0.9058	High Similarity	NPC262635
0.9051	High Similarity	NPC38153
0.9044	High Similarity	NPC104796
0.9021	High Similarity	NPC88445
0.9014	High Similarity	NPC74539
0.9014	High Similarity	NPC304443
0.8958	High Similarity	NPC191104
0.8947	High Similarity	NPC473894
0.8944	High Similarity	NPC154217
0.8944	High Similarity	NPC470322
0.8939	High Similarity	NPC49852
0.8939	High Similarity	NPC475496
0.8929	High Similarity	NPC229916
0.8913	High Similarity	NPC221046
0.8905	High Similarity	NPC46869
0.8897	High Similarity	NPC98028
0.8897	High Similarity	NPC292998
0.8873	High Similarity	NPC246903
0.8873	High Similarity	NPC1886
0.8873	High Similarity	NPC196137
0.8873	High Similarity	NPC171656
0.8873	High Similarity	NPC294365
0.8872	High Similarity	NPC473907
0.8865	High Similarity	NPC51146
0.8865	High Similarity	NPC166858
0.8849	High Similarity	NPC183639
0.8849	High Similarity	NPC199458
0.8841	High Similarity	NPC254741
0.8841	High Similarity	NPC161196
0.8832	High Similarity	NPC125920
0.8819	High Similarity	NPC266743
0.8811	High Similarity	NPC181388
0.8803	High Similarity	NPC188632
0.8803	High Similarity	NPC470296
0.8803	High Similarity	NPC87609
0.8803	High Similarity	NPC94794
0.8803	High Similarity	NPC196459
0.8803	High Similarity	NPC112791
0.8794	High Similarity	NPC24075
0.8794	High Similarity	NPC201820
0.8788	High Similarity	NPC471828
0.8788	High Similarity	NPC471827
0.8786	High Similarity	NPC241975
0.8786	High Similarity	NPC19476
0.8779	High Similarity	NPC472518
0.8777	High Similarity	NPC131782
0.8777	High Similarity	NPC474624
0.8777	High Similarity	NPC138047
0.8769	High Similarity	NPC144418
0.8768	High Similarity	NPC151113
0.8768	High Similarity	NPC60667
0.8759	High Similarity	NPC108113
0.8759	High Similarity	NPC93756
0.8759	High Similarity	NPC247743
0.875	High Similarity	NPC282335
0.875	High Similarity	NPC218300
0.875	High Similarity	NPC278556
0.875	High Similarity	NPC284424
0.8741	High Similarity	NPC179970
0.8741	High Similarity	NPC469935
0.8741	High Similarity	NPC469953
0.8741	High Similarity	NPC208584
0.8741	High Similarity	NPC311741
0.8741	High Similarity	NPC234629
0.8741	High Similarity	NPC178627
0.8732	High Similarity	NPC470556
0.8732	High Similarity	NPC36181
0.8731	High Similarity	NPC125887
0.8714	High Similarity	NPC470669
0.8714	High Similarity	NPC470083
0.8714	High Similarity	NPC219584
0.8714	High Similarity	NPC131130
0.8714	High Similarity	NPC17848
0.8714	High Similarity	NPC470668
0.8712	High Similarity	NPC27671
0.8712	High Similarity	NPC201667
0.8712	High Similarity	NPC73413
0.8705	High Similarity	NPC174999
0.8702	High Similarity	NPC248429
0.8702	High Similarity	NPC96286
0.8699	High Similarity	NPC474735
0.8699	High Similarity	NPC474660
0.869	High Similarity	NPC161864
0.869	High Similarity	NPC208303
0.8686	High Similarity	NPC473655
0.8686	High Similarity	NPC25937
0.8686	High Similarity	NPC101294
0.8686	High Similarity	NPC182428
0.8681	High Similarity	NPC473927
0.8681	High Similarity	NPC190572
0.8671	High Similarity	NPC470553
0.8671	High Similarity	NPC470909
0.8671	High Similarity	NPC474939
0.8671	High Similarity	NPC96216
0.8671	High Similarity	NPC76657
0.8671	High Similarity	NPC307895
0.8667	High Similarity	NPC473019
0.8662	High Similarity	NPC103362
0.8662	High Similarity	NPC110969
0.8662	High Similarity	NPC282300
0.8662	High Similarity	NPC470555
0.8657	High Similarity	NPC41721
0.8652	High Similarity	NPC477956
0.8652	High Similarity	NPC310370
0.8652	High Similarity	NPC18260
0.8652	High Similarity	NPC78913
0.8652	High Similarity	NPC473076
0.8652	High Similarity	NPC11566
0.8652	High Similarity	NPC23257
0.8652	High Similarity	NPC183642
0.8649	High Similarity	NPC131725
0.8647	High Similarity	NPC165556
0.8647	High Similarity	NPC65041
0.8643	High Similarity	NPC307883
0.8643	High Similarity	NPC157855
0.8643	High Similarity	NPC259685
0.8639	High Similarity	NPC290671
0.8636	High Similarity	NPC273772
0.8636	High Similarity	NPC109675
0.863	High Similarity	NPC19238
0.863	High Similarity	NPC164299
0.863	High Similarity	NPC469932
0.8623	High Similarity	NPC223354
0.8621	High Similarity	NPC297886
0.8621	High Similarity	NPC180477
0.8621	High Similarity	NPC140120
0.8621	High Similarity	NPC249942
0.8621	High Similarity	NPC129650
0.8615	High Similarity	NPC230951
0.8613	High Similarity	NPC31872
0.8613	High Similarity	NPC473584
0.8613	High Similarity	NPC475589
0.8611	High Similarity	NPC470554
0.8611	High Similarity	NPC288910
0.8611	High Similarity	NPC118059
0.8611	High Similarity	NPC133060
0.8601	High Similarity	NPC11561
0.8601	High Similarity	NPC294432
0.8601	High Similarity	NPC112829
0.8601	High Similarity	NPC162476
0.8601	High Similarity	NPC226636
0.86	High Similarity	NPC269495
0.8593	High Similarity	NPC199204
0.8593	High Similarity	NPC185066
0.8593	High Similarity	NPC475017
0.8593	High Similarity	NPC472519
0.8592	High Similarity	NPC471587
0.8592	High Similarity	NPC474037
0.8592	High Similarity	NPC241100
0.8592	High Similarity	NPC16455
0.8592	High Similarity	NPC172986
0.8592	High Similarity	NPC101366
0.8592	High Similarity	NPC307990
0.8592	High Similarity	NPC261227
0.8592	High Similarity	NPC270883
0.8592	High Similarity	NPC159275
0.8592	High Similarity	NPC221173
0.8592	High Similarity	NPC472409
0.8592	High Similarity	NPC150522
0.8591	High Similarity	NPC278010
0.8591	High Similarity	NPC250769
0.8591	High Similarity	NPC295608
0.8582	High Similarity	NPC201395
0.8582	High Similarity	NPC234109
0.8582	High Similarity	NPC474487
0.8582	High Similarity	NPC188327
0.8582	High Similarity	NPC470671
0.8582	High Similarity	NPC471826
0.8582	High Similarity	NPC470672
0.8582	High Similarity	NPC474504
0.8571	High Similarity	NPC473466
0.8571	High Similarity	NPC158866
0.8571	High Similarity	NPC111347
0.8571	High Similarity	NPC156910
0.8571	High Similarity	NPC29638
0.8571	High Similarity	NPC472883
0.8571	High Similarity	NPC155882
0.8571	High Similarity	NPC180351
0.8562	High Similarity	NPC266572
0.8562	High Similarity	NPC211811
0.8562	High Similarity	NPC469933
0.8562	High Similarity	NPC39195
0.8561	High Similarity	NPC61499

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 NPC472516 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	975
0.2-0.3	1769
0.3-0.4	2700
0.4-0.5	1833
0.5-0.6	1004
0.6-0.7	320
0.7-0.8	104
0.8-0.85	34
0.85-0.9	14
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9058	High Similarity	NPD1243	Approved
0.9014	High Similarity	NPD920	Approved
0.8873	High Similarity	NPD642	Clinical (unspecified phase)
0.8865	High Similarity	NPD643	Clinical (unspecified phase)
0.8705	High Similarity	NPD2796	Approved
0.8633	High Similarity	NPD3748	Approved
0.85	High Similarity	NPD2799	Discontinued
0.8483	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD919	Approved
0.8414	Intermediate Similarity	NPD6799	Approved
0.84	Intermediate Similarity	NPD7819	Suspended
0.84	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD7411	Suspended
0.8369	Intermediate Similarity	NPD1510	Phase 2
0.8345	Intermediate Similarity	NPD1240	Approved
0.8333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1296	Phase 2
0.8333	Intermediate Similarity	NPD2313	Discontinued
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD3750	Approved
0.8322	Intermediate Similarity	NPD1549	Phase 2
0.8321	Intermediate Similarity	NPD6832	Phase 2
0.831	Intermediate Similarity	NPD1551	Phase 2
0.8284	Intermediate Similarity	NPD9717	Approved
0.8252	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7075	Discontinued
0.8231	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD1607	Approved
0.82	Intermediate Similarity	NPD6599	Discontinued
0.8175	Intermediate Similarity	NPD1019	Discontinued
0.817	Intermediate Similarity	NPD7768	Phase 2
0.8108	Intermediate Similarity	NPD5401	Approved
0.8102	Intermediate Similarity	NPD1203	Approved
0.8074	Intermediate Similarity	NPD422	Phase 1
0.8056	Intermediate Similarity	NPD2935	Discontinued
0.8028	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2800	Approved
0.8013	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD3749	Approved
0.7987	Intermediate Similarity	NPD3817	Phase 2
0.7987	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD3267	Approved
0.7971	Intermediate Similarity	NPD3266	Approved
0.7962	Intermediate Similarity	NPD1247	Approved
0.7961	Intermediate Similarity	NPD4380	Phase 2
0.7958	Intermediate Similarity	NPD4307	Phase 2
0.7943	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1511	Approved
0.7902	Intermediate Similarity	NPD447	Suspended
0.7895	Intermediate Similarity	NPD3226	Approved
0.7877	Intermediate Similarity	NPD2346	Discontinued
0.7871	Intermediate Similarity	NPD5402	Approved
0.7867	Intermediate Similarity	NPD2532	Approved
0.7867	Intermediate Similarity	NPD2534	Approved
0.7867	Intermediate Similarity	NPD2533	Approved
0.7817	Intermediate Similarity	NPD411	Approved
0.7815	Intermediate Similarity	NPD1512	Approved
0.7806	Intermediate Similarity	NPD2801	Approved
0.7803	Intermediate Similarity	NPD1241	Discontinued
0.7791	Intermediate Similarity	NPD5953	Discontinued
0.7786	Intermediate Similarity	NPD2798	Approved
0.7778	Intermediate Similarity	NPD5124	Phase 1
0.7778	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1933	Approved
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1934	Approved
0.774	Intermediate Similarity	NPD4308	Phase 3
0.7724	Intermediate Similarity	NPD6651	Approved
0.7718	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2797	Approved
0.7707	Intermediate Similarity	NPD3882	Suspended
0.7692	Intermediate Similarity	NPD3268	Approved
0.7669	Intermediate Similarity	NPD7286	Phase 2
0.7664	Intermediate Similarity	NPD17	Approved
0.7654	Intermediate Similarity	NPD7473	Discontinued
0.7635	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD9493	Approved
0.7578	Intermediate Similarity	NPD6232	Discontinued
0.7561	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2654	Approved
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4288	Approved
0.7531	Intermediate Similarity	NPD3926	Phase 2
0.753	Intermediate Similarity	NPD6559	Discontinued
0.7517	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD3818	Discontinued
0.7484	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7462	Intermediate Similarity	NPD9697	Approved
0.7455	Intermediate Similarity	NPD5844	Phase 1
0.7452	Intermediate Similarity	NPD5890	Approved
0.7452	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5889	Approved
0.7429	Intermediate Similarity	NPD1281	Approved
0.7415	Intermediate Similarity	NPD230	Phase 1
0.7407	Intermediate Similarity	NPD6959	Discontinued
0.74	Intermediate Similarity	NPD1471	Phase 3
0.7394	Intermediate Similarity	NPD1876	Approved
0.7394	Intermediate Similarity	NPD3225	Approved
0.7394	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD9545	Approved
0.7389	Intermediate Similarity	NPD6585	Discontinued
0.7383	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1465	Phase 2
0.7347	Intermediate Similarity	NPD943	Approved
0.7343	Intermediate Similarity	NPD1164	Approved
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2309	Approved
0.7308	Intermediate Similarity	NPD9261	Approved
0.7305	Intermediate Similarity	NPD1610	Phase 2
0.7303	Intermediate Similarity	NPD1652	Phase 2
0.7278	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD6166	Phase 2
0.7273	Intermediate Similarity	NPD2403	Approved
0.7273	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7033	Discontinued
0.7266	Intermediate Similarity	NPD1548	Phase 1
0.7256	Intermediate Similarity	NPD5711	Approved
0.7256	Intermediate Similarity	NPD5710	Approved
0.7255	Intermediate Similarity	NPD7003	Approved
0.7254	Intermediate Similarity	NPD3972	Approved
0.7246	Intermediate Similarity	NPD7054	Approved
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5691	Approved
0.7211	Intermediate Similarity	NPD3764	Approved
0.7206	Intermediate Similarity	NPD5535	Approved
0.7202	Intermediate Similarity	NPD7472	Approved
0.7202	Intermediate Similarity	NPD7074	Phase 3
0.7192	Intermediate Similarity	NPD4908	Phase 1
0.7181	Intermediate Similarity	NPD6355	Discontinued
0.7171	Intermediate Similarity	NPD6004	Phase 3
0.7171	Intermediate Similarity	NPD2353	Approved
0.7171	Intermediate Similarity	NPD6005	Phase 3
0.7171	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6002	Phase 3
0.7162	Intermediate Similarity	NPD8032	Phase 2
0.716	Intermediate Similarity	NPD6797	Phase 2
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD6808	Phase 2
0.7143	Intermediate Similarity	NPD3134	Approved
0.7134	Intermediate Similarity	NPD6273	Approved
0.7134	Intermediate Similarity	NPD5049	Phase 3
0.7118	Intermediate Similarity	NPD7251	Discontinued
0.7114	Intermediate Similarity	NPD2979	Phase 3
0.7107	Intermediate Similarity	NPD7458	Discontinued
0.7105	Intermediate Similarity	NPD4477	Approved
0.7105	Intermediate Similarity	NPD6100	Approved
0.7105	Intermediate Similarity	NPD4476	Approved
0.7105	Intermediate Similarity	NPD6099	Approved
0.7099	Intermediate Similarity	NPD5353	Approved
0.7097	Intermediate Similarity	NPD3887	Approved
0.7095	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6798	Discontinued
0.7092	Intermediate Similarity	NPD1651	Approved
0.709	Intermediate Similarity	NPD1358	Approved
0.709	Intermediate Similarity	NPD9263	Approved
0.709	Intermediate Similarity	NPD9267	Approved
0.709	Intermediate Similarity	NPD9264	Approved
0.7079	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7808	Phase 3
0.7063	Intermediate Similarity	NPD1611	Approved
0.7059	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1778	Approved
0.7042	Intermediate Similarity	NPD4626	Approved
0.7037	Intermediate Similarity	NPD74	Approved
0.7037	Intermediate Similarity	NPD9266	Approved
0.7035	Intermediate Similarity	NPD8312	Approved
0.7035	Intermediate Similarity	NPD8313	Approved
0.7029	Intermediate Similarity	NPD4287	Approved
0.7021	Intermediate Similarity	NPD1894	Discontinued
0.7014	Intermediate Similarity	NPD1481	Phase 2
0.7013	Intermediate Similarity	NPD2424	Discontinued
0.7012	Intermediate Similarity	NPD6971	Discontinued
0.7006	Intermediate Similarity	NPD5242	Approved
0.7006	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1729	Discontinued
0.7	Intermediate Similarity	NPD3140	Approved
0.7	Intermediate Similarity	NPD3142	Approved
0.6993	Remote Similarity	NPD2438	Suspended
0.6993	Remote Similarity	NPD5404	Approved
0.6993	Remote Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD5408	Approved
0.6993	Remote Similarity	NPD5405	Approved
0.6987	Remote Similarity	NPD2354	Approved
0.6986	Remote Similarity	NPD1470	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