NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	261.669
LogP:	2.977
LogD:	3.079
LogS:	-4.073
# Rotatable Bonds:	1
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	2.798
Fsp3:	0.267
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:	-4.617
MDCK Permeability:	1.876464011729695e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	88.64221954345703%
Volume Distribution (VD):	0.942
Pgp-substrate:	8.905643463134766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.86
CYP2C19-inhibitor:	0.681
CYP2C19-substrate:	0.603
CYP2C9-inhibitor:	0.485
CYP2C9-substrate:	0.752
CYP2D6-inhibitor:	0.843
CYP2D6-substrate:	0.688
CYP3A4-inhibitor:	0.743
CYP3A4-substrate:	0.357

ADMET: Excretion

Clearance (CL):	9.079
Half-life (T1/2):	0.446

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.373
Skin Sensitization:	0.284
Carcinogencity:	0.909
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.806

Download Data

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

Natural Product: NPC167517

Natural Product ID:	NPC167517
*Common Name:**	Braylin
IUPAC Name:	6-methoxy-8,8-dimethylpyrano[2,3-f]chromen-2-one
Synonyms:
Standard InCHIKey:	UOFNVZWWIXXTMZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O4/c1-15(2)7-6-10-13-9(4-5-12(16)18-13)8-11(17-3)14(10)19-15/h4-8H,1-3H3
SMILES:	COc1cc2ccc(=O)oc2c2c1OC(C)(C)C=C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL529210
PubChem CID:	618370
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597921]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19319	Cedrelopsis grevei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19319	Cedrelopsis grevei	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]
NPO19319	Cedrelopsis grevei	Species	Rutaceae	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
EC50	1
IC50	1
Others	16

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Others	4
TISSUE	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[515201]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[515201]
NPT1464	Individual Protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	960.0	nM	PMID[515202]
NPT2	Others	Unspecified		Activity	=	19.4	%	PMID[515201]
NPT2	Others	Unspecified		Activity	=	52.2	%	PMID[515201]
NPT2	Others	Unspecified		Activity	=	87.2	%	PMID[515201]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[515201]
NPT26157	TISSUE	Mesenteric artery	Rattus norvegicus	Emax	=	96.7	%	PMID[515203]
NPT26157	TISSUE	Mesenteric artery	Rattus norvegicus	pD2	=	5.802	n.a.	PMID[515203]
NPT26157	TISSUE	Mesenteric artery	Rattus norvegicus	EC50	=	1580.0	nM	PMID[515203]
NPT26157	TISSUE	Mesenteric artery	Rattus norvegicus	FC	=	70.89	n.a.	PMID[515203]
NPT26157	TISSUE	Mesenteric artery	Rattus norvegicus	Emax	=	94.87	%	PMID[515203]
NPT26157	TISSUE	Mesenteric artery	Rattus norvegicus	Emax	=	93.69	%	PMID[515203]
NPT26157	TISSUE	Mesenteric artery	Rattus norvegicus	Emax	=	94.01	%	PMID[515203]
NPT26157	TISSUE	Mesenteric artery	Rattus norvegicus	Emax	=	53.34	%	PMID[515203]
NPT26157	TISSUE	Mesenteric artery	Rattus norvegicus	Emax	=	54.13	%	PMID[515203]

☑ 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 NPC167517 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	489
0.1-0.2	2117
0.2-0.3	5511
0.3-0.4	11498
0.4-0.5	5733
0.5-0.6	4219
0.6-0.7	5760
0.7-0.8	5143
0.8-0.85	1711
0.85-0.9	426
0.9-0.95	84
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC270256
0.969	High Similarity	NPC123954
0.9542	High Similarity	NPC147030
0.9535	High Similarity	NPC240722
0.9535	High Similarity	NPC244799
0.9457	High Similarity	NPC27239
0.9457	High Similarity	NPC123127
0.9412	High Similarity	NPC236419
0.9394	High Similarity	NPC309953
0.9389	High Similarity	NPC137669
0.9323	High Similarity	NPC234865
0.9318	High Similarity	NPC241341
0.9318	High Similarity	NPC233018
0.9318	High Similarity	NPC472522
0.9318	High Similarity	NPC36437
0.9254	High Similarity	NPC286843
0.9179	High Similarity	NPC472521
0.9098	High Similarity	NPC319969
0.9091	High Similarity	NPC19242
0.9044	High Similarity	NPC95162
0.9044	High Similarity	NPC139548
0.9044	High Similarity	NPC148835
0.9044	High Similarity	NPC76336
0.9044	High Similarity	NPC20511
0.9044	High Similarity	NPC20796
0.9044	High Similarity	NPC52086
0.9037	High Similarity	NPC240915
0.8992	High Similarity	NPC173350
0.8992	High Similarity	NPC290605
0.8992	High Similarity	NPC154176
0.8986	High Similarity	NPC300611
0.8978	High Similarity	NPC13067
0.8978	High Similarity	NPC164148
0.8978	High Similarity	NPC43500
0.8971	High Similarity	NPC126682
0.8971	High Similarity	NPC82271
0.8963	High Similarity	NPC474600
0.8963	High Similarity	NPC7163
0.8939	High Similarity	NPC474616
0.8915	High Similarity	NPC257188
0.8915	High Similarity	NPC13007
0.8905	High Similarity	NPC474521
0.8905	High Similarity	NPC474540
0.8905	High Similarity	NPC474530
0.8897	High Similarity	NPC73071
0.8889	High Similarity	NPC167111
0.8889	High Similarity	NPC207002
0.8889	High Similarity	NPC318400
0.8889	High Similarity	NPC133956
0.8889	High Similarity	NPC471910
0.8889	High Similarity	NPC296624
0.8857	High Similarity	NPC230157
0.8857	High Similarity	NPC34245
0.8857	High Similarity	NPC110067
0.8857	High Similarity	NPC91492
0.8857	High Similarity	NPC7439
0.8857	High Similarity	NPC256555
0.8849	High Similarity	NPC279851
0.8849	High Similarity	NPC472520
0.8824	High Similarity	NPC18804
0.8824	High Similarity	NPC164269
0.8824	High Similarity	NPC127888
0.8824	High Similarity	NPC166672
0.8824	High Similarity	NPC92830
0.8824	High Similarity	NPC198381
0.8824	High Similarity	NPC319859
0.8824	High Similarity	NPC74655
0.8824	High Similarity	NPC267412
0.8824	High Similarity	NPC260265
0.8824	High Similarity	NPC287182
0.8824	High Similarity	NPC47163
0.8824	High Similarity	NPC84894
0.8824	High Similarity	NPC100986
0.8824	High Similarity	NPC195343
0.8803	High Similarity	NPC205361
0.8794	High Similarity	NPC471763
0.8788	High Similarity	NPC471826
0.8779	High Similarity	NPC111347
0.8769	High Similarity	NPC194626
0.8759	High Similarity	NPC471909
0.8759	High Similarity	NPC281241
0.8759	High Similarity	NPC86892
0.8759	High Similarity	NPC471625
0.8759	High Similarity	NPC472424
0.875	High Similarity	NPC26673
0.8741	High Similarity	NPC231149
0.8723	High Similarity	NPC138212
0.8722	High Similarity	NPC474670
0.8722	High Similarity	NPC194841
0.8702	High Similarity	NPC472518
0.8702	High Similarity	NPC109675
0.8702	High Similarity	NPC273772
0.8702	High Similarity	NPC50720
0.8696	High Similarity	NPC149320
0.8696	High Similarity	NPC476455
0.8696	High Similarity	NPC224543
0.8696	High Similarity	NPC128529
0.8696	High Similarity	NPC55615
0.8696	High Similarity	NPC471630
0.8696	High Similarity	NPC78746
0.8696	High Similarity	NPC160727
0.8696	High Similarity	NPC177281
0.8696	High Similarity	NPC188380
0.8696	High Similarity	NPC283019
0.8692	High Similarity	NPC144418
0.8686	High Similarity	NPC55149
0.8686	High Similarity	NPC307412
0.8676	High Similarity	NPC19157
0.8676	High Similarity	NPC14248
0.8676	High Similarity	NPC137949
0.8667	High Similarity	NPC474617
0.8667	High Similarity	NPC80170
0.8657	High Similarity	NPC474623
0.8657	High Similarity	NPC199204
0.8657	High Similarity	NPC474651
0.8657	High Similarity	NPC185066
0.8647	High Similarity	NPC127604
0.8636	High Similarity	NPC27671
0.8636	High Similarity	NPC201667
0.8636	High Similarity	NPC291899
0.8636	High Similarity	NPC73413
0.8633	High Similarity	NPC153818
0.8633	High Similarity	NPC38874
0.8633	High Similarity	NPC294456
0.8633	High Similarity	NPC184861
0.8633	High Similarity	NPC232246
0.8633	High Similarity	NPC212124
0.8633	High Similarity	NPC225106
0.8633	High Similarity	NPC281014
0.8626	High Similarity	NPC96286
0.8626	High Similarity	NPC150214
0.8626	High Similarity	NPC248429
0.8623	High Similarity	NPC224941
0.8623	High Similarity	NPC33986
0.8623	High Similarity	NPC311430
0.8623	High Similarity	NPC469675
0.8613	High Similarity	NPC222036
0.8613	High Similarity	NPC277021
0.8613	High Similarity	NPC7526
0.8611	High Similarity	NPC15577
0.8605	High Similarity	NPC298796
0.8603	High Similarity	NPC73738
0.8601	High Similarity	NPC476450
0.8593	High Similarity	NPC168710
0.8582	High Similarity	NPC474821
0.8571	High Similarity	NPC471827
0.8571	High Similarity	NPC279573
0.8571	High Similarity	NPC471828
0.8571	High Similarity	NPC211110
0.8552	High Similarity	NPC96294
0.8552	High Similarity	NPC139839
0.8552	High Similarity	NPC48366
0.8551	High Similarity	NPC98179
0.8551	High Similarity	NPC62366
0.8551	High Similarity	NPC253574
0.8538	High Similarity	NPC222175
0.8531	High Similarity	NPC185127
0.8529	High Similarity	NPC476399
0.8527	High Similarity	NPC265547
0.8527	High Similarity	NPC152306
0.8519	High Similarity	NPC474636
0.8519	High Similarity	NPC157212
0.8511	High Similarity	NPC312881
0.8507	High Similarity	NPC234109
0.8507	High Similarity	NPC474632
0.8507	High Similarity	NPC188327
0.85	High Similarity	NPC155963
0.85	High Similarity	NPC476171
0.85	High Similarity	NPC474886
0.8493	Intermediate Similarity	NPC30688
0.8493	Intermediate Similarity	NPC176903
0.8489	Intermediate Similarity	NPC472525
0.8485	Intermediate Similarity	NPC288238
0.8478	Intermediate Similarity	NPC472524
0.8473	Intermediate Similarity	NPC163200
0.8462	Intermediate Similarity	NPC281356
0.8451	Intermediate Similarity	NPC195357
0.8451	Intermediate Similarity	NPC152771
0.8451	Intermediate Similarity	NPC287286
0.8446	Intermediate Similarity	NPC470264
0.8444	Intermediate Similarity	NPC289316
0.844	Intermediate Similarity	NPC151946
0.8435	Intermediate Similarity	NPC120426
0.8435	Intermediate Similarity	NPC21184
0.8435	Intermediate Similarity	NPC294522
0.8435	Intermediate Similarity	NPC205727
0.8435	Intermediate Similarity	NPC114740
0.8433	Intermediate Similarity	NPC202594
0.8433	Intermediate Similarity	NPC232692
0.8429	Intermediate Similarity	NPC26954
0.8429	Intermediate Similarity	NPC38099
0.8429	Intermediate Similarity	NPC283331
0.8421	Intermediate Similarity	NPC143725
0.8421	Intermediate Similarity	NPC315807
0.8417	Intermediate Similarity	NPC224475
0.8417	Intermediate Similarity	NPC213173
0.8417	Intermediate Similarity	NPC180716
0.8417	Intermediate Similarity	NPC326600
0.8417	Intermediate Similarity	NPC50896
0.8417	Intermediate Similarity	NPC204353

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 NPC167517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	434
0.1-0.2	1044
0.2-0.3	1948
0.3-0.4	2717
0.4-0.5	1695
0.5-0.6	875
0.6-0.7	303
0.7-0.8	101
0.8-0.85	26
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8367	Intermediate Similarity	NPD1653	Approved
0.8	Intermediate Similarity	NPD422	Phase 1
0.7958	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD5124	Phase 1
0.7885	Intermediate Similarity	NPD919	Approved
0.7867	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5844	Phase 1
0.7786	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1613	Approved
0.773	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5494	Approved
0.7703	Intermediate Similarity	NPD1652	Phase 2
0.7692	Intermediate Similarity	NPD3817	Phase 2
0.7673	Intermediate Similarity	NPD1247	Approved
0.7636	Intermediate Similarity	NPD7549	Discontinued
0.7628	Intermediate Similarity	NPD2801	Approved
0.7622	Intermediate Similarity	NPD1296	Phase 2
0.7609	Intermediate Similarity	NPD1611	Approved
0.7586	Intermediate Similarity	NPD447	Suspended
0.7551	Intermediate Similarity	NPD3748	Approved
0.7535	Intermediate Similarity	NPD3018	Phase 2
0.7519	Intermediate Similarity	NPD9697	Approved
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD920	Approved
0.7467	Intermediate Similarity	NPD1243	Approved
0.7452	Intermediate Similarity	NPD1934	Approved
0.7431	Intermediate Similarity	NPD3027	Phase 3
0.7429	Intermediate Similarity	NPD2981	Phase 2
0.7421	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3496	Discontinued
0.7405	Intermediate Similarity	NPD1465	Phase 2
0.7405	Intermediate Similarity	NPD1358	Approved
0.7405	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5691	Approved
0.7386	Intermediate Similarity	NPD1511	Approved
0.7376	Intermediate Similarity	NPD2982	Phase 2
0.7376	Intermediate Similarity	NPD2983	Phase 2
0.7372	Intermediate Similarity	NPD5536	Phase 2
0.7358	Intermediate Similarity	NPD5402	Approved
0.7347	Intermediate Similarity	NPD1933	Approved
0.7338	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3225	Approved
0.732	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1548	Phase 1
0.7303	Intermediate Similarity	NPD3750	Approved
0.7301	Intermediate Similarity	NPD6232	Discontinued
0.7296	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7819	Suspended
0.729	Intermediate Similarity	NPD1512	Approved
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7267	Intermediate Similarity	NPD2796	Approved
0.726	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5535	Approved
0.7234	Intermediate Similarity	NPD1610	Phase 2
0.7233	Intermediate Similarity	NPD6801	Discontinued
0.723	Intermediate Similarity	NPD230	Phase 1
0.7226	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4626	Approved
0.7206	Intermediate Similarity	NPD5283	Phase 1
0.7192	Intermediate Similarity	NPD4625	Phase 3
0.7178	Intermediate Similarity	NPD5677	Discontinued
0.7171	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7162	Intermediate Similarity	NPD4060	Phase 1
0.7162	Intermediate Similarity	NPD4307	Phase 2
0.7161	Intermediate Similarity	NPD6799	Approved
0.716	Intermediate Similarity	NPD7075	Discontinued
0.7153	Intermediate Similarity	NPD3266	Approved
0.7153	Intermediate Similarity	NPD3267	Approved
0.7134	Intermediate Similarity	NPD7199	Phase 2
0.7133	Intermediate Similarity	NPD4749	Approved
0.7126	Intermediate Similarity	NPD3818	Discontinued
0.7125	Intermediate Similarity	NPD37	Approved
0.7123	Intermediate Similarity	NPD4908	Phase 1
0.7118	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5401	Approved
0.7114	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3705	Approved
0.7099	Intermediate Similarity	NPD3882	Suspended
0.7099	Intermediate Similarity	NPD4965	Approved
0.7099	Intermediate Similarity	NPD4966	Approved
0.7099	Intermediate Similarity	NPD4967	Phase 2
0.7068	Intermediate Similarity	NPD3134	Approved
0.7063	Intermediate Similarity	NPD7411	Suspended
0.7051	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3539	Phase 1
0.7039	Intermediate Similarity	NPD1551	Phase 2
0.7037	Intermediate Similarity	NPD5353	Approved
0.7034	Intermediate Similarity	NPD2797	Approved
0.703	Intermediate Similarity	NPD8127	Discontinued
0.7027	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5403	Approved
0.7014	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6234	Discontinued
0.7006	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6599	Discontinued
0.7	Intermediate Similarity	NPD4380	Phase 2
0.7	Intermediate Similarity	NPD7644	Approved
0.6994	Remote Similarity	NPD7768	Phase 2
0.6993	Remote Similarity	NPD3540	Phase 1
0.6986	Remote Similarity	NPD1019	Discontinued
0.6982	Remote Similarity	NPD7054	Approved
0.6978	Remote Similarity	NPD6671	Approved
0.6974	Remote Similarity	NPD1510	Phase 2
0.6974	Remote Similarity	NPD4308	Phase 3
0.6972	Remote Similarity	NPD17	Approved
0.6972	Remote Similarity	NPD1778	Approved
0.6966	Remote Similarity	NPD8651	Approved
0.6959	Remote Similarity	NPD7095	Approved
0.6948	Remote Similarity	NPD1549	Phase 2
0.6948	Remote Similarity	NPD2424	Discontinued
0.6946	Remote Similarity	NPD3926	Phase 2
0.6946	Remote Similarity	NPD5242	Approved
0.6944	Remote Similarity	NPD9717	Approved
0.6943	Remote Similarity	NPD4357	Discontinued
0.6943	Remote Similarity	NPD5297	Approved
0.6943	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7074	Phase 3
0.6941	Remote Similarity	NPD7472	Approved
0.6939	Remote Similarity	NPD2861	Phase 2
0.6934	Remote Similarity	NPD228	Approved
0.6923	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6190	Approved
0.6913	Remote Similarity	NPD2313	Discontinued
0.6913	Remote Similarity	NPD3268	Approved
0.6903	Remote Similarity	NPD6674	Discontinued
0.6901	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6832	Phase 2
0.6887	Remote Similarity	NPD4340	Discontinued
0.6883	Remote Similarity	NPD7266	Discontinued
0.6883	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1375	Discontinued
0.6875	Remote Similarity	NPD1091	Approved
0.6867	Remote Similarity	NPD6233	Phase 2
0.686	Remote Similarity	NPD6559	Discontinued
0.6852	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5090	Approved
0.6852	Remote Similarity	NPD5089	Approved
0.6848	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2653	Approved
0.6835	Remote Similarity	NPD1241	Discontinued
0.6833	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3226	Approved
0.6832	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1608	Approved
0.6824	Remote Similarity	NPD2237	Approved
0.6821	Remote Similarity	NPD7808	Phase 3
0.6821	Remote Similarity	NPD1240	Approved
0.6803	Remote Similarity	NPD1203	Approved
0.6802	Remote Similarity	NPD6797	Phase 2
0.68	Remote Similarity	NPD411	Approved
0.68	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7985	Registered
0.68	Remote Similarity	NPD6798	Discontinued
0.6797	Remote Similarity	NPD7097	Phase 1
0.6795	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2534	Approved
0.6792	Remote Similarity	NPD2533	Approved
0.6792	Remote Similarity	NPD2532	Approved
0.6786	Remote Similarity	NPD7229	Phase 3
0.6783	Remote Similarity	NPD5585	Approved
0.6774	Remote Similarity	NPD5763	Approved
0.6774	Remote Similarity	NPD5762	Approved
0.6774	Remote Similarity	NPD2346	Discontinued
0.677	Remote Similarity	NPD3687	Approved
0.677	Remote Similarity	NPD3686	Approved
0.6768	Remote Similarity	NPD4585	Approved
0.6765	Remote Similarity	NPD290	Approved
0.6763	Remote Similarity	NPD7251	Discontinued
0.6759	Remote Similarity	NPD1281	Approved
0.6753	Remote Similarity	NPD7033	Discontinued
0.6753	Remote Similarity	NPD2799	Discontinued
0.6752	Remote Similarity	NPD4110	Phase 3
0.6752	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4628	Phase 3
0.6752	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6386	Approved
0.6748	Remote Similarity	NPD6385	Approved
0.6747	Remote Similarity	NPD3749	Approved
0.6735	Remote Similarity	NPD6696	Suspended
0.6732	Remote Similarity	NPD1607	Approved
0.6728	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4288	Approved
0.6725	Remote Similarity	NPD7228	Approved
0.6715	Remote Similarity	NPD2684	Approved
0.6711	Remote Similarity	NPD4140	Approved
0.671	Remote Similarity	NPD6099	Approved
0.671	Remote Similarity	NPD6100	Approved
0.6709	Remote Similarity	NPD2219	Phase 1

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