NPASS Compound

Structure

CID14248 OpenBabel06191715342D 24 26 0 0 1 0 0 0 0 0999 V2000 -8.6369 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6369 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 0.0000 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 -7.1369 2.7321 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 -3.5491 1.8090 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 -8.1369 2.7321 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 1 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 -6.6369 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 1.0000 0.0000 C 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 -7.1369 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 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 -5.6369 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 17 1 0 0 0 0 7 11 2 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 16 19 1 6 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.13
Volume:	337.007
LogP:	4.316
LogD:	3.022
LogS:	-4.223
# Rotatable Bonds:	4
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.491
Synthetic Accessibility Score:	3.445
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.646
MDCK Permeability:	3.122195630567148e-05
Pgp-inhibitor:	0.805
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	88.68254852294922%
Volume Distribution (VD):	0.81
Pgp-substrate:	11.801261901855469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.843
CYP1A2-substrate:	0.84
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.302
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.717
CYP2D6-inhibitor:	0.713
CYP2D6-substrate:	0.768
CYP3A4-inhibitor:	0.727
CYP3A4-substrate:	0.497

ADMET: Excretion

Clearance (CL):	10.729
Half-life (T1/2):	0.363

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.658
Drug-inuced Liver Injury (DILI):	0.748
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.808
Carcinogencity:	0.713
Eye Corrosion:	0.241
Eye Irritation:	0.381
Respiratory Toxicity:	0.479

Download Data

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

Natural Product: NPC14248

Natural Product ID:	NPC14248
*Common Name:**	(-)-Prantschimgin
IUPAC Name:	2-[(2S)-7-oxo-2,3-dihydrofuro[3,2-g]chromen-2-yl]propan-2-yl 3-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	PQCLZBCFLJVBGA-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C19H20O5/c1-11(2)7-18(21)24-19(3,4)16-9-13-8-12-5-6-17(20)23-14(12)10-15(13)22-16/h5-8,10,16H,9H2,1-4H3/t16-/m0/s1
SMILES:	CC(=CC(=O)OC(C)(C)[C@@H]1Cc2cc3ccc(=O)oc3cc2O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2402007
PubChem CID:	908164
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens

*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
NPO6177	Veronicastrum japonicum	Species	Plantaginaceae	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	5

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	14950.0	nM	PMID[537108]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	>	100000.0	nM	PMID[537108]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	83300.0	nM	PMID[537108]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5200.0	nM	PMID[537108]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3100.0	nM	PMID[537108]

☑ 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 NPC14248 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	404
0.1-0.2	1665
0.2-0.3	4163
0.3-0.4	9782
0.4-0.5	8765
0.5-0.6	4082
0.6-0.7	6147
0.7-0.8	5573
0.8-0.85	1496
0.85-0.9	419
0.9-0.95	154
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC7526
0.9921	High Similarity	NPC222036
0.9843	High Similarity	NPC307412
0.9843	High Similarity	NPC55149
0.969	High Similarity	NPC283331
0.9609	High Similarity	NPC207002
0.9609	High Similarity	NPC133956
0.9609	High Similarity	NPC296624
0.9609	High Similarity	NPC471910
0.9609	High Similarity	NPC167111
0.9609	High Similarity	NPC318400
0.9535	High Similarity	NPC198381
0.9535	High Similarity	NPC260265
0.9535	High Similarity	NPC98179
0.9535	High Similarity	NPC84894
0.9535	High Similarity	NPC164269
0.9535	High Similarity	NPC127888
0.9535	High Similarity	NPC74655
0.9535	High Similarity	NPC100986
0.9535	High Similarity	NPC195343
0.9535	High Similarity	NPC47163
0.9535	High Similarity	NPC319859
0.9535	High Similarity	NPC267412
0.9535	High Similarity	NPC253574
0.9535	High Similarity	NPC166672
0.9535	High Similarity	NPC287182
0.9535	High Similarity	NPC18804
0.952	High Similarity	NPC234109
0.952	High Similarity	NPC188327
0.9462	High Similarity	NPC471625
0.9462	High Similarity	NPC33986
0.9462	High Similarity	NPC86892
0.9462	High Similarity	NPC281241
0.9462	High Similarity	NPC471909
0.9462	High Similarity	NPC472424
0.9462	High Similarity	NPC469675
0.9389	High Similarity	NPC160727
0.9389	High Similarity	NPC471630
0.9389	High Similarity	NPC476455
0.9389	High Similarity	NPC128529
0.9389	High Similarity	NPC283019
0.9389	High Similarity	NPC55615
0.9389	High Similarity	NPC177281
0.9389	High Similarity	NPC149320
0.9375	High Similarity	NPC80170
0.936	High Similarity	NPC201667
0.936	High Similarity	NPC73413
0.9318	High Similarity	NPC155963
0.9313	High Similarity	NPC472525
0.9297	High Similarity	NPC168710
0.9286	High Similarity	NPC471827
0.9286	High Similarity	NPC471828
0.928	High Similarity	NPC472518
0.928	High Similarity	NPC273772
0.928	High Similarity	NPC109675
0.9248	High Similarity	NPC211110
0.9248	High Similarity	NPC279573
0.9248	High Similarity	NPC151946
0.9242	High Similarity	NPC26954
0.9242	High Similarity	NPC38099
0.9237	High Similarity	NPC180716
0.9237	High Similarity	NPC224475
0.9237	High Similarity	NPC62366
0.9237	High Similarity	NPC213173
0.9219	High Similarity	NPC199204
0.9219	High Similarity	NPC185066
0.9219	High Similarity	NPC472519
0.9213	High Similarity	NPC471826
0.9206	High Similarity	NPC27671
0.92	High Similarity	NPC248429
0.92	High Similarity	NPC96286
0.9179	High Similarity	NPC312881
0.9173	High Similarity	NPC14697
0.9173	High Similarity	NPC153818
0.9173	High Similarity	NPC232246
0.916	High Similarity	NPC31849
0.916	High Similarity	NPC163557
0.9154	High Similarity	NPC29734
0.9111	High Similarity	NPC195357
0.9111	High Similarity	NPC287286
0.9111	High Similarity	NPC152771
0.9098	High Similarity	NPC188380
0.9098	High Similarity	NPC224543
0.9098	High Similarity	NPC78746
0.9091	High Similarity	NPC50896
0.9091	High Similarity	NPC326600
0.9091	High Similarity	NPC204353
0.9077	High Similarity	NPC113098
0.9055	High Similarity	NPC291899
0.9055	High Similarity	NPC111347
0.904	High Similarity	NPC180006
0.904	High Similarity	NPC235190
0.904	High Similarity	NPC163200
0.903	High Similarity	NPC184861
0.903	High Similarity	NPC225106
0.903	High Similarity	NPC281014
0.903	High Similarity	NPC294456
0.903	High Similarity	NPC212124
0.9015	High Similarity	NPC469449
0.9008	High Similarity	NPC267336
0.9008	High Similarity	NPC272650
0.8993	High Similarity	NPC296377
0.8978	High Similarity	NPC119640
0.8978	High Similarity	NPC183646
0.8976	High Similarity	NPC154176
0.8976	High Similarity	NPC50720
0.8976	High Similarity	NPC290605
0.8976	High Similarity	NPC173350
0.8968	High Similarity	NPC144418
0.8939	High Similarity	NPC194277
0.8939	High Similarity	NPC469956
0.8931	High Similarity	NPC19242
0.8929	High Similarity	NPC169510
0.8923	High Similarity	NPC60704
0.8923	High Similarity	NPC139595
0.8923	High Similarity	NPC293642
0.8913	High Similarity	NPC471824
0.8913	High Similarity	NPC476457
0.8898	High Similarity	NPC150214
0.8898	High Similarity	NPC13007
0.8898	High Similarity	NPC257188
0.8889	High Similarity	NPC471069
0.8889	High Similarity	NPC471068
0.888	High Similarity	NPC281356
0.888	High Similarity	NPC298796
0.8872	High Similarity	NPC469952
0.8872	High Similarity	NPC469955
0.8849	High Similarity	NPC85624
0.8849	High Similarity	NPC469701
0.8849	High Similarity	NPC76657
0.8846	High Similarity	NPC258567
0.8846	High Similarity	NPC243688
0.8846	High Similarity	NPC224774
0.8846	High Similarity	NPC121740
0.8846	High Similarity	NPC289316
0.8828	High Similarity	NPC315807
0.8824	High Similarity	NPC471070
0.8824	High Similarity	NPC471072
0.8824	High Similarity	NPC270256
0.8824	High Similarity	NPC471071
0.88	High Similarity	NPC152306
0.88	High Similarity	NPC96705
0.88	High Similarity	NPC265547
0.8797	High Similarity	NPC123954
0.8797	High Similarity	NPC19157
0.8779	High Similarity	NPC469453
0.8779	High Similarity	NPC157212
0.8769	High Similarity	NPC101894
0.8769	High Similarity	NPC163248
0.875	High Similarity	NPC306365
0.8731	High Similarity	NPC233018
0.8731	High Similarity	NPC54503
0.8731	High Similarity	NPC36437
0.8731	High Similarity	NPC472522
0.8731	High Similarity	NPC55147
0.8731	High Similarity	NPC241341
0.8723	High Similarity	NPC87950
0.8723	High Similarity	NPC471764
0.8692	High Similarity	NPC93219
0.8692	High Similarity	NPC232692
0.8692	High Similarity	NPC244495
0.8692	High Similarity	NPC202594
0.8682	High Similarity	NPC143725
0.8676	High Similarity	NPC167517
0.8667	High Similarity	NPC131950
0.8657	High Similarity	NPC137669
0.8657	High Similarity	NPC175159
0.8657	High Similarity	NPC319969
0.8647	High Similarity	NPC32463
0.8643	High Similarity	NPC471763
0.864	High Similarity	NPC128633
0.8613	High Similarity	NPC131198
0.8603	High Similarity	NPC229128
0.8593	High Similarity	NPC291551
0.8593	High Similarity	NPC1220
0.8593	High Similarity	NPC241165
0.8593	High Similarity	NPC469965
0.8593	High Similarity	NPC141822
0.8593	High Similarity	NPC2363
0.8593	High Similarity	NPC205797
0.8593	High Similarity	NPC142563
0.8582	High Similarity	NPC472517
0.8561	High Similarity	NPC138149
0.8561	High Similarity	NPC215512
0.8561	High Similarity	NPC300611
0.8561	High Similarity	NPC472520
0.8561	High Similarity	NPC279851
0.8561	High Similarity	NPC472523
0.8561	High Similarity	NPC476442
0.8552	High Similarity	NPC470264
0.8551	High Similarity	NPC144512
0.8551	High Similarity	NPC137262
0.8551	High Similarity	NPC35501
0.8551	High Similarity	NPC47040
0.8551	High Similarity	NPC307883
0.8551	High Similarity	NPC278600
0.8551	High Similarity	NPC37428
0.854	High Similarity	NPC286843
0.8529	High Similarity	NPC147030
0.8529	High Similarity	NPC309953

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 NPC14248 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	949
0.2-0.3	1741
0.3-0.4	2635
0.4-0.5	1896
0.5-0.6	1069
0.6-0.7	369
0.7-0.8	111
0.8-0.85	27
0.85-0.9	11
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8593	High Similarity	NPD5123	Clinical (unspecified phase)
0.8593	High Similarity	NPD5124	Phase 1
0.8385	Intermediate Similarity	NPD422	Phase 1
0.8169	Intermediate Similarity	NPD1652	Phase 2
0.8088	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD1243	Approved
0.8027	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1296	Phase 2
0.7958	Intermediate Similarity	NPD2796	Approved
0.7947	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD1358	Approved
0.7891	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD3748	Approved
0.7881	Intermediate Similarity	NPD6801	Discontinued
0.7879	Intermediate Similarity	NPD5691	Approved
0.7857	Intermediate Similarity	NPD919	Approved
0.7842	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6799	Approved
0.7792	Intermediate Similarity	NPD7075	Discontinued
0.776	Intermediate Similarity	NPD9697	Approved
0.7752	Intermediate Similarity	NPD5535	Approved
0.7733	Intermediate Similarity	NPD1653	Approved
0.7724	Intermediate Similarity	NPD2424	Discontinued
0.7718	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3134	Approved
0.7698	Intermediate Similarity	NPD4908	Phase 1
0.7669	Intermediate Similarity	NPD1548	Phase 1
0.7632	Intermediate Similarity	NPD6599	Discontinued
0.7619	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3750	Approved
0.7606	Intermediate Similarity	NPD4060	Phase 1
0.7597	Intermediate Similarity	NPD7819	Suspended
0.7582	Intermediate Similarity	NPD7411	Suspended
0.758	Intermediate Similarity	NPD5494	Approved
0.7574	Intermediate Similarity	NPD1610	Phase 2
0.7571	Intermediate Similarity	NPD6832	Phase 2
0.7556	Intermediate Similarity	NPD4626	Approved
0.7552	Intermediate Similarity	NPD6355	Discontinued
0.7551	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5403	Approved
0.7536	Intermediate Similarity	NPD8651	Approved
0.7533	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD5401	Approved
0.7517	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7483	Intermediate Similarity	NPD4307	Phase 2
0.7483	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3266	Approved
0.7482	Intermediate Similarity	NPD3267	Approved
0.7482	Intermediate Similarity	NPD2797	Approved
0.7469	Intermediate Similarity	NPD5844	Phase 1
0.7465	Intermediate Similarity	NPD6798	Discontinued
0.7451	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2684	Approved
0.7436	Intermediate Similarity	NPD3817	Phase 2
0.7434	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4340	Discontinued
0.7417	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6005	Phase 3
0.7415	Intermediate Similarity	NPD5762	Approved
0.7415	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5763	Approved
0.7415	Intermediate Similarity	NPD6002	Phase 3
0.7415	Intermediate Similarity	NPD6004	Phase 3
0.741	Intermediate Similarity	NPD3225	Approved
0.7394	Intermediate Similarity	NPD4625	Phase 3
0.7394	Intermediate Similarity	NPD3027	Phase 3
0.7389	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1549	Phase 2
0.7355	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7843	Approved
0.7347	Intermediate Similarity	NPD1551	Phase 2
0.7343	Intermediate Similarity	NPD3268	Approved
0.7343	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4749	Approved
0.7333	Intermediate Similarity	NPD6559	Discontinued
0.7329	Intermediate Similarity	NPD7097	Phase 1
0.7325	Intermediate Similarity	NPD5402	Approved
0.7324	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1611	Approved
0.7319	Intermediate Similarity	NPD1091	Approved
0.7313	Intermediate Similarity	NPD7157	Approved
0.7312	Intermediate Similarity	NPD1247	Approved
0.7303	Intermediate Similarity	NPD2532	Approved
0.7303	Intermediate Similarity	NPD2534	Approved
0.7303	Intermediate Similarity	NPD2533	Approved
0.7297	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1241	Discontinued
0.7285	Intermediate Similarity	NPD5058	Phase 3
0.7279	Intermediate Similarity	NPD2799	Discontinued
0.7279	Intermediate Similarity	NPD1510	Phase 2
0.7279	Intermediate Similarity	NPD4308	Phase 3
0.7278	Intermediate Similarity	NPD3882	Suspended
0.7267	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7466	Approved
0.7255	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3018	Phase 2
0.7248	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4140	Approved
0.7233	Intermediate Similarity	NPD3749	Approved
0.7231	Intermediate Similarity	NPD290	Approved
0.723	Intermediate Similarity	NPD2935	Discontinued
0.7215	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7199	Phase 2
0.7197	Intermediate Similarity	NPD37	Approved
0.7197	Intermediate Similarity	NPD1934	Approved
0.7195	Intermediate Similarity	NPD3818	Discontinued
0.7194	Intermediate Similarity	NPD3705	Approved
0.7192	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7549	Discontinued
0.7183	Intermediate Similarity	NPD1019	Discontinued
0.7178	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1778	Approved
0.7172	Intermediate Similarity	NPD6233	Phase 2
0.7171	Intermediate Similarity	NPD6666	Approved
0.7171	Intermediate Similarity	NPD6667	Approved
0.717	Intermediate Similarity	NPD4965	Approved
0.717	Intermediate Similarity	NPD4966	Approved
0.717	Intermediate Similarity	NPD4967	Phase 2
0.7162	Intermediate Similarity	NPD5588	Approved
0.716	Intermediate Similarity	NPD7229	Phase 3
0.7153	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2981	Phase 2
0.7143	Intermediate Similarity	NPD9717	Approved
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7124	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1240	Approved
0.7117	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2438	Suspended
0.7107	Intermediate Similarity	NPD2415	Discontinued
0.7105	Intermediate Similarity	NPD3887	Approved
0.7103	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2313	Discontinued
0.7095	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4536	Approved
0.7095	Intermediate Similarity	NPD4538	Approved
0.7092	Intermediate Similarity	NPD2982	Phase 2
0.7092	Intermediate Similarity	NPD2983	Phase 2
0.7086	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2800	Approved
0.7081	Intermediate Similarity	NPD6234	Discontinued
0.708	Intermediate Similarity	NPD5536	Phase 2
0.7075	Intermediate Similarity	NPD1933	Approved
0.7067	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4062	Phase 3
0.705	Intermediate Similarity	NPD17	Approved
0.7044	Intermediate Similarity	NPD2801	Approved
0.7044	Intermediate Similarity	NPD8455	Phase 2
0.7037	Intermediate Similarity	NPD5283	Phase 1
0.7027	Intermediate Similarity	NPD1607	Approved
0.7013	Intermediate Similarity	NPD7213	Phase 3
0.7013	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7212	Phase 2
0.7012	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD6032	Approved
0.7	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD4477	Approved
0.7	Intermediate Similarity	NPD4476	Approved
0.6994	Remote Similarity	NPD8127	Discontinued
0.6993	Remote Similarity	NPD1203	Approved
0.6986	Remote Similarity	NPD1048	Approved
0.6978	Remote Similarity	NPD5585	Approved
0.6972	Remote Similarity	NPD5327	Phase 3
0.697	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7447	Phase 1
0.6964	Remote Similarity	NPD5953	Discontinued
0.6959	Remote Similarity	NPD447	Suspended
0.6957	Remote Similarity	NPD7644	Approved
0.6951	Remote Similarity	NPD6232	Discontinued
0.695	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3690	Phase 2
0.6944	Remote Similarity	NPD3691	Phase 2
0.6939	Remote Similarity	NPD8032	Phase 2
0.6934	Remote Similarity	NPD6671	Approved
0.6933	Remote Similarity	NPD5960	Phase 3
0.6928	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4110	Phase 3
0.6923	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD6696	Suspended
0.6923	Remote Similarity	NPD5049	Phase 3
0.6914	Remote Similarity	NPD6971	Discontinued
0.6913	Remote Similarity	NPD6653	Approved
0.6906	Remote Similarity	NPD1894	Discontinued
0.6903	Remote Similarity	NPD5297	Approved
0.6903	Remote Similarity	NPD1511	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