NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.12
Volume:	287.521
LogP:	3.891
LogD:	3.156
LogS:	-4.374
# Rotatable Bonds:	4
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.634
Synthetic Accessibility Score:	2.489
Fsp3:	0.312
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:	-4.684
MDCK Permeability:	1.746892485243734e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.664

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	76.92809295654297%
Volume Distribution (VD):	0.96
Pgp-substrate:	15.546439170837402%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.901
CYP2C19-substrate:	0.778
CYP2C9-inhibitor:	0.434
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.27
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.293
CYP3A4-substrate:	0.4

ADMET: Excretion

Clearance (CL):	12.531
Half-life (T1/2):	0.296

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.815
Drug-inuced Liver Injury (DILI):	0.586
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.248
Carcinogencity:	0.407
Eye Corrosion:	0.003
Eye Irritation:	0.123
Respiratory Toxicity:	0.245

Download Data

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

Natural Product: NPC201667

Natural Product ID:	NPC201667
*Common Name:**	Toddaculin
IUPAC Name:	5,7-dimethoxy-6-(3-methylbut-2-enyl)chromen-2-one
Synonyms:
Standard InCHIKey:	KRQHZFHWEAJPNO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18O4/c1-10(2)5-6-11-13(18-3)9-14-12(16(11)19-4)7-8-15(17)20-14/h5,7-9H,6H2,1-4H3
SMILES:	CC(=CCc1c(cc2c(ccc(=O)o2)c1OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3235996
PubChem CID:	5321960
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
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597921]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7213	Toddalia asiatica	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1464	Individual Protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	9980.0	nM	PMID[500184]

☑ 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 NPC201667 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	428
0.1-0.2	1923
0.2-0.3	5223
0.3-0.4	11561
0.4-0.5	6039
0.5-0.6	4846
0.6-0.7	5963
0.7-0.8	4589
0.8-0.85	1319
0.85-0.9	593
0.9-0.95	165
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC73413
0.9915	High Similarity	NPC472518
0.9915	High Similarity	NPC273772
0.9915	High Similarity	NPC109675
0.9831	High Similarity	NPC27671
0.9829	High Similarity	NPC96286
0.9829	High Similarity	NPC248429
0.9748	High Similarity	NPC471828
0.9748	High Similarity	NPC471827
0.9669	High Similarity	NPC472519
0.9576	High Similarity	NPC144418
0.9508	High Similarity	NPC185066
0.9504	High Similarity	NPC471826
0.95	High Similarity	NPC291899
0.9492	High Similarity	NPC235190
0.9492	High Similarity	NPC180006
0.9492	High Similarity	NPC163200
0.9487	High Similarity	NPC298796
0.9431	High Similarity	NPC168710
0.9426	High Similarity	NPC243688
0.9417	High Similarity	NPC154176
0.9417	High Similarity	NPC173350
0.9417	High Similarity	NPC315807
0.9417	High Similarity	NPC290605
0.9417	High Similarity	NPC50720
0.9402	High Similarity	NPC96705
0.9402	High Similarity	NPC265547
0.9402	High Similarity	NPC152306
0.936	High Similarity	NPC14248
0.9355	High Similarity	NPC80170
0.935	High Similarity	NPC199204
0.9344	High Similarity	NPC234109
0.9344	High Similarity	NPC188327
0.9339	High Similarity	NPC111347
0.9333	High Similarity	NPC257188
0.9333	High Similarity	NPC13007
0.9333	High Similarity	NPC150214
0.9322	High Similarity	NPC281356
0.9286	High Similarity	NPC318400
0.9286	High Similarity	NPC471910
0.9286	High Similarity	NPC31849
0.9286	High Similarity	NPC207002
0.9286	High Similarity	NPC167111
0.9286	High Similarity	NPC133956
0.9286	High Similarity	NPC222036
0.9286	High Similarity	NPC7526
0.9286	High Similarity	NPC296624
0.9262	High Similarity	NPC244495
0.9262	High Similarity	NPC93219
0.9231	High Similarity	NPC128633
0.9213	High Similarity	NPC47163
0.9213	High Similarity	NPC74655
0.9213	High Similarity	NPC307412
0.9213	High Similarity	NPC195343
0.9213	High Similarity	NPC55149
0.9213	High Similarity	NPC198381
0.9213	High Similarity	NPC127888
0.9213	High Similarity	NPC319859
0.9213	High Similarity	NPC100986
0.9213	High Similarity	NPC18804
0.9213	High Similarity	NPC164269
0.9213	High Similarity	NPC166672
0.9213	High Similarity	NPC84894
0.9213	High Similarity	NPC260265
0.9213	High Similarity	NPC267412
0.9213	High Similarity	NPC287182
0.9206	High Similarity	NPC19157
0.92	High Similarity	NPC32463
0.9194	High Similarity	NPC157212
0.9141	High Similarity	NPC471909
0.9141	High Similarity	NPC281241
0.9141	High Similarity	NPC472424
0.9141	High Similarity	NPC469675
0.9141	High Similarity	NPC86892
0.9141	High Similarity	NPC471625
0.9134	High Similarity	NPC55147
0.9134	High Similarity	NPC54503
0.9113	High Similarity	NPC121740
0.9113	High Similarity	NPC289316
0.9113	High Similarity	NPC224774
0.9113	High Similarity	NPC258567
0.9106	High Similarity	NPC202594
0.9106	High Similarity	NPC232692
0.9098	High Similarity	NPC143725
0.907	High Similarity	NPC55615
0.907	High Similarity	NPC26954
0.907	High Similarity	NPC177281
0.907	High Similarity	NPC160727
0.907	High Similarity	NPC471630
0.907	High Similarity	NPC38099
0.907	High Similarity	NPC283019
0.907	High Similarity	NPC283331
0.907	High Similarity	NPC476455
0.907	High Similarity	NPC149320
0.907	High Similarity	NPC128529
0.9062	High Similarity	NPC62366
0.9062	High Similarity	NPC204353
0.9062	High Similarity	NPC326600
0.9062	High Similarity	NPC213173
0.9062	High Similarity	NPC50896
0.9062	High Similarity	NPC224475
0.9062	High Similarity	NPC180716
0.9055	High Similarity	NPC175159
0.9055	High Similarity	NPC469956
0.9055	High Similarity	NPC194277
0.9048	High Similarity	NPC113098
0.904	High Similarity	NPC60704
0.904	High Similarity	NPC469453
0.904	High Similarity	NPC139595
0.904	High Similarity	NPC293642
0.9032	High Similarity	NPC163248
0.9032	High Similarity	NPC101894
0.9	High Similarity	NPC155963
0.8992	High Similarity	NPC472525
0.8992	High Similarity	NPC229128
0.8992	High Similarity	NPC61499
0.8984	High Similarity	NPC469952
0.8984	High Similarity	NPC163557
0.8984	High Similarity	NPC469955
0.8976	High Similarity	NPC272650
0.8976	High Similarity	NPC29734
0.8976	High Similarity	NPC267336
0.8976	High Similarity	NPC472517
0.8934	High Similarity	NPC52247
0.8934	High Similarity	NPC187868
0.8931	High Similarity	NPC151946
0.8931	High Similarity	NPC253616
0.8931	High Similarity	NPC279573
0.8931	High Similarity	NPC211110
0.8915	High Similarity	NPC98179
0.8915	High Similarity	NPC131950
0.8915	High Similarity	NPC253574
0.8898	High Similarity	NPC19242
0.8864	High Similarity	NPC312881
0.8855	High Similarity	NPC14697
0.8855	High Similarity	NPC306365
0.8855	High Similarity	NPC153818
0.8855	High Similarity	NPC268081
0.8855	High Similarity	NPC232246
0.8852	High Similarity	NPC319378
0.8852	High Similarity	NPC302107
0.8846	High Similarity	NPC33986
0.8837	High Similarity	NPC469449
0.8837	High Similarity	NPC2363
0.8837	High Similarity	NPC472524
0.8837	High Similarity	NPC472522
0.8819	High Similarity	NPC474289
0.88	High Similarity	NPC168259
0.8797	High Similarity	NPC287286
0.8797	High Similarity	NPC310370
0.8797	High Similarity	NPC195357
0.8797	High Similarity	NPC183642
0.8797	High Similarity	NPC472523
0.8797	High Similarity	NPC152771
0.8788	High Similarity	NPC270256
0.8788	High Similarity	NPC307883
0.8779	High Similarity	NPC224543
0.8779	High Similarity	NPC78746
0.8779	High Similarity	NPC188380
0.877	High Similarity	NPC247553
0.876	High Similarity	NPC123954
0.8722	High Similarity	NPC71903
0.8722	High Similarity	NPC36414
0.8718	High Similarity	NPC473809
0.8712	High Similarity	NPC471068
0.8712	High Similarity	NPC294456
0.8712	High Similarity	NPC131198
0.8712	High Similarity	NPC471069
0.8712	High Similarity	NPC184861
0.8712	High Similarity	NPC472516
0.8712	High Similarity	NPC212124
0.8712	High Similarity	NPC281014
0.8712	High Similarity	NPC225106
0.8692	High Similarity	NPC291551
0.8692	High Similarity	NPC205797
0.8692	High Similarity	NPC1220
0.8692	High Similarity	NPC241165
0.8692	High Similarity	NPC141822
0.8692	High Similarity	NPC36437
0.8692	High Similarity	NPC142563
0.8692	High Similarity	NPC241341
0.8692	High Similarity	NPC233018
0.8682	High Similarity	NPC66430
0.8682	High Similarity	NPC37009
0.8678	High Similarity	NPC471498
0.8678	High Similarity	NPC471503
0.8678	High Similarity	NPC183154
0.8678	High Similarity	NPC263754
0.8667	High Similarity	NPC183646
0.8667	High Similarity	NPC119640
0.8657	High Similarity	NPC170812
0.8657	High Similarity	NPC138149
0.8657	High Similarity	NPC155552
0.8657	High Similarity	NPC472515
0.8647	High Similarity	NPC47040
0.8647	High Similarity	NPC37428
0.8647	High Similarity	NPC471070
0.8647	High Similarity	NPC278600
0.8647	High Similarity	NPC471071
0.8647	High Similarity	NPC35501

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 NPC201667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	987
0.2-0.3	1703
0.3-0.4	2741
0.4-0.5	1789
0.5-0.6	1045
0.6-0.7	338
0.7-0.8	105
0.8-0.85	33
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8934	High Similarity	NPD422	Phase 1
0.8692	High Similarity	NPD5123	Clinical (unspecified phase)
0.8692	High Similarity	NPD5124	Phase 1
0.8594	High Similarity	NPD1008	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1296	Phase 2
0.8321	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD9697	Approved
0.8264	Intermediate Similarity	NPD5535	Approved
0.8222	Intermediate Similarity	NPD3748	Approved
0.8116	Intermediate Similarity	NPD1652	Phase 2
0.8116	Intermediate Similarity	NPD1243	Approved
0.8095	Intermediate Similarity	NPD5691	Approved
0.8067	Intermediate Similarity	NPD3134	Approved
0.8045	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD2796	Approved
0.8016	Intermediate Similarity	NPD1548	Phase 1
0.8	Intermediate Similarity	NPD1358	Approved
0.7972	Intermediate Similarity	NPD920	Approved
0.7943	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3267	Approved
0.7939	Intermediate Similarity	NPD3266	Approved
0.7939	Intermediate Similarity	NPD2797	Approved
0.7929	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD6832	Phase 2
0.7895	Intermediate Similarity	NPD4908	Phase 1
0.7891	Intermediate Similarity	NPD4626	Approved
0.7887	Intermediate Similarity	NPD6799	Approved
0.7877	Intermediate Similarity	NPD7411	Suspended
0.7863	Intermediate Similarity	NPD3225	Approved
0.7857	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6801	Discontinued
0.7801	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3268	Approved
0.777	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD7819	Suspended
0.7769	Intermediate Similarity	NPD1610	Phase 2
0.7708	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3496	Discontinued
0.7687	Intermediate Similarity	NPD6599	Discontinued
0.7667	Intermediate Similarity	NPD7768	Phase 2
0.7664	Intermediate Similarity	NPD4307	Phase 2
0.7634	Intermediate Similarity	NPD1611	Approved
0.7619	Intermediate Similarity	NPD1241	Discontinued
0.7619	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7075	Discontinued
0.7576	Intermediate Similarity	NPD9717	Approved
0.7574	Intermediate Similarity	NPD4625	Phase 3
0.7571	Intermediate Similarity	NPD2799	Discontinued
0.7566	Intermediate Similarity	NPD919	Approved
0.7551	Intermediate Similarity	NPD1653	Approved
0.7536	Intermediate Similarity	NPD1240	Approved
0.7536	Intermediate Similarity	NPD4060	Phase 1
0.7535	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1549	Phase 2
0.7519	Intermediate Similarity	NPD4749	Approved
0.7518	Intermediate Similarity	NPD1551	Phase 2
0.7518	Intermediate Similarity	NPD2935	Discontinued
0.7517	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2684	Approved
0.7483	Intermediate Similarity	NPD5403	Approved
0.7482	Intermediate Similarity	NPD4340	Discontinued
0.7481	Intermediate Similarity	NPD1019	Discontinued
0.7466	Intermediate Similarity	NPD5401	Approved
0.7465	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD8651	Approved
0.7447	Intermediate Similarity	NPD1510	Phase 2
0.7447	Intermediate Similarity	NPD4308	Phase 3
0.7447	Intermediate Similarity	NPD7033	Discontinued
0.7431	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1607	Approved
0.7415	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1203	Approved
0.7402	Intermediate Similarity	NPD7843	Approved
0.7391	Intermediate Similarity	NPD6798	Discontinued
0.7391	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2313	Discontinued
0.7372	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3817	Phase 2
0.7357	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1778	Approved
0.7348	Intermediate Similarity	NPD17	Approved
0.7333	Intermediate Similarity	NPD4380	Phase 2
0.7329	Intermediate Similarity	NPD6666	Approved
0.7329	Intermediate Similarity	NPD6667	Approved
0.7325	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4628	Phase 3
0.7303	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3018	Phase 2
0.7297	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5844	Phase 1
0.7295	Intermediate Similarity	NPD940	Approved
0.7295	Intermediate Similarity	NPD846	Approved
0.7293	Intermediate Similarity	NPD3847	Discontinued
0.7292	Intermediate Similarity	NPD2424	Discontinued
0.7286	Intermediate Similarity	NPD1613	Approved
0.7286	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4288	Approved
0.7248	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1091	Approved
0.7234	Intermediate Similarity	NPD6355	Discontinued
0.7234	Intermediate Similarity	NPD1933	Approved
0.7231	Intermediate Similarity	NPD7157	Approved
0.723	Intermediate Similarity	NPD2534	Approved
0.723	Intermediate Similarity	NPD2532	Approved
0.723	Intermediate Similarity	NPD2533	Approved
0.7226	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6004	Phase 3
0.7222	Intermediate Similarity	NPD6002	Phase 3
0.7222	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6005	Phase 3
0.7222	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1894	Discontinued
0.7194	Intermediate Similarity	NPD3027	Phase 3
0.7188	Intermediate Similarity	NPD1137	Approved
0.7188	Intermediate Similarity	NPD1139	Approved
0.7185	Intermediate Similarity	NPD2981	Phase 2
0.7185	Intermediate Similarity	NPD1608	Approved
0.7179	Intermediate Similarity	NPD5494	Approved
0.7165	Intermediate Similarity	NPD5451	Approved
0.7163	Intermediate Similarity	NPD4140	Approved
0.7162	Intermediate Similarity	NPD7212	Phase 2
0.7162	Intermediate Similarity	NPD7213	Phase 3
0.7161	Intermediate Similarity	NPD3749	Approved
0.7161	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4476	Approved
0.7153	Intermediate Similarity	NPD4477	Approved
0.7143	Intermediate Similarity	NPD290	Approved
0.7143	Intermediate Similarity	NPD5585	Approved
0.7143	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD7097	Phase 1
0.7133	Intermediate Similarity	NPD2200	Suspended
0.7132	Intermediate Similarity	NPD2982	Phase 2
0.7132	Intermediate Similarity	NPD1138	Approved
0.7132	Intermediate Similarity	NPD2983	Phase 2
0.7123	Intermediate Similarity	NPD2800	Approved
0.7121	Intermediate Similarity	NPD5536	Phase 2
0.7121	Intermediate Similarity	NPD7644	Approved
0.7114	Intermediate Similarity	NPD7447	Phase 1
0.7111	Intermediate Similarity	NPD1281	Approved
0.7111	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5762	Approved
0.7103	Intermediate Similarity	NPD5763	Approved
0.7101	Intermediate Similarity	NPD3690	Phase 2
0.7101	Intermediate Similarity	NPD3691	Phase 2
0.7099	Intermediate Similarity	NPD2557	Approved
0.7099	Intermediate Similarity	NPD5953	Discontinued
0.7099	Intermediate Similarity	NPD6387	Discontinued
0.7099	Intermediate Similarity	NPD6671	Approved
0.7092	Intermediate Similarity	NPD8032	Phase 2
0.7092	Intermediate Similarity	NPD6233	Phase 2
0.7089	Intermediate Similarity	NPD7229	Phase 3
0.7081	Intermediate Similarity	NPD7286	Phase 2
0.7078	Intermediate Similarity	NPD2801	Approved
0.7077	Intermediate Similarity	NPD5283	Phase 1
0.7075	Intermediate Similarity	NPD7466	Approved
0.7071	Intermediate Similarity	NPD7095	Approved
0.7068	Intermediate Similarity	NPD9545	Approved
0.7063	Intermediate Similarity	NPD6651	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7051	Intermediate Similarity	NPD6971	Discontinued
0.705	Intermediate Similarity	NPD2237	Approved
0.705	Intermediate Similarity	NPD2861	Phase 2
0.7047	Intermediate Similarity	NPD1511	Approved
0.7045	Intermediate Similarity	NPD3596	Phase 2
0.7042	Intermediate Similarity	NPD2979	Phase 3
0.7039	Intermediate Similarity	NPD3226	Approved
0.7034	Intermediate Similarity	NPD6099	Approved
0.7034	Intermediate Similarity	NPD6100	Approved
0.7025	Intermediate Similarity	NPD1247	Approved
0.7021	Intermediate Similarity	NPD411	Approved
0.7015	Intermediate Similarity	NPD1651	Approved
0.7013	Intermediate Similarity	NPD1934	Approved
0.7012	Intermediate Similarity	NPD7549	Discontinued
0.7007	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2654	Approved
0.7	Intermediate Similarity	NPD821	Approved
0.7	Intermediate Similarity	NPD2614	Approved
0.6993	Remote Similarity	NPD447	Suspended
0.6987	Remote Similarity	NPD3882	Suspended
0.6986	Remote Similarity	NPD2346	Discontinued
0.6986	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1535	Discovery
0.6981	Remote Similarity	NPD6232	Discontinued
0.698	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2798	Approved
0.6975	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4062	Phase 3
0.6959	Remote Similarity	NPD7003	Approved
0.6957	Remote Similarity	NPD1283	Approved
0.6954	Remote Similarity	NPD1512	Approved
0.6954	Remote Similarity	NPD5049	Phase 3
0.6951	Remote Similarity	NPD6559	Discontinued

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