NPASS Compound

Structure

NPC472521 OpenBabel07101718192D 23 24 0 0 0 0 0 0 0 0999 V2000 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 4.0000 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 1.7321 1.0000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 4.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 11 15 2 0 0 0 0 12 18 2 0 0 0 0 12 23 1 0 0 0 0 13 23 1 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.13
Volume:	322.398
LogP:	1.882
LogD:	2.123
LogS:	-3.119
# Rotatable Bonds:	5
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.853
Synthetic Accessibility Score:	2.9
Fsp3:	0.353
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:	-4.539
MDCK Permeability:	1.675958264968358e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.51
Plasma Protein Binding (PPB):	70.8455810546875%
Volume Distribution (VD):	1.13
Pgp-substrate:	27.42555809020996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.74
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.324
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.155
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.55
CYP2D6-substrate:	0.772
CYP3A4-inhibitor:	0.427
CYP3A4-substrate:	0.639

ADMET: Excretion

Clearance (CL):	8.455
Half-life (T1/2):	0.54

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.512
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.298
Rat Oral Acute Toxicity:	0.826
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.197
Carcinogencity:	0.452
Eye Corrosion:	0.003
Eye Irritation:	0.235
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC472521

Natural Product ID:	NPC472521
*Common Name:**	WCKNIJCEFGBCCT-CMDGGOBGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WCKNIJCEFGBCCT-CMDGGOBGSA-N
Standard InCHI:	InChI=1S/C17H20O6/c1-17(2,19)9-8-11-13-10(6-7-12(18)23-13)14(20-3)16(22-5)15(11)21-4/h6-9,19H,1-5H3/b9-8+
SMILES:	CC(C)(C=CC1=C(C(=C(C2=C1OC(=O)C=C2)OC)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426674
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	=	12400.0	nM	PMID[523931]

☑ 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 NPC472521 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	400
0.1-0.2	1831
0.2-0.3	4999
0.3-0.4	10546
0.4-0.5	7121
0.5-0.6	3981
0.6-0.7	5474
0.7-0.8	5135
0.8-0.85	2118
0.85-0.9	1035
0.9-0.95	53
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC147030
0.9538	High Similarity	NPC472522
0.9478	High Similarity	NPC472520
0.9478	High Similarity	NPC279851
0.9242	High Similarity	NPC26673
0.9185	High Similarity	NPC270256
0.9185	High Similarity	NPC43500
0.9185	High Similarity	NPC164148
0.9179	High Similarity	NPC167517
0.9098	High Similarity	NPC36437
0.9098	High Similarity	NPC233018
0.9098	High Similarity	NPC241341
0.9084	High Similarity	NPC27239
0.9084	High Similarity	NPC123127
0.9058	High Similarity	NPC236419
0.9051	High Similarity	NPC300611
0.9037	High Similarity	NPC82271
0.9037	High Similarity	NPC126682
0.9023	High Similarity	NPC137669
0.9023	High Similarity	NPC123954
0.9015	High Similarity	NPC244799
0.9015	High Similarity	NPC240722
0.8993	High Similarity	NPC471763
0.8971	High Similarity	NPC76336
0.8971	High Similarity	NPC148835
0.8971	High Similarity	NPC139548
0.8971	High Similarity	NPC20511
0.8971	High Similarity	NPC52086
0.8971	High Similarity	NPC95162
0.8923	High Similarity	NPC232692
0.8923	High Similarity	NPC202594
0.8905	High Similarity	NPC13067
0.8897	High Similarity	NPC286843
0.8881	High Similarity	NPC319969
0.8872	High Similarity	NPC19242
0.8865	High Similarity	NPC205361
0.8824	High Similarity	NPC234865
0.8786	High Similarity	NPC138212
0.8786	High Similarity	NPC91492
0.8786	High Similarity	NPC256555
0.8786	High Similarity	NPC7439
0.8786	High Similarity	NPC34245
0.8786	High Similarity	NPC110067
0.875	High Similarity	NPC92830
0.875	High Similarity	NPC309953
0.8722	High Similarity	NPC474616
0.8696	High Similarity	NPC476171
0.8692	High Similarity	NPC150214
0.8686	High Similarity	NPC472525
0.8686	High Similarity	NPC240915
0.8662	High Similarity	NPC476450
0.8652	High Similarity	NPC230157
0.8633	High Similarity	NPC279573
0.8633	High Similarity	NPC211110
0.8633	High Similarity	NPC151946
0.8626	High Similarity	NPC50720
0.8623	High Similarity	NPC38099
0.8623	High Similarity	NPC26954
0.8613	High Similarity	NPC474600
0.8613	High Similarity	NPC224475
0.8613	High Similarity	NPC213173
0.8613	High Similarity	NPC180716
0.8603	High Similarity	NPC5423
0.8603	High Similarity	NPC137949
0.8603	High Similarity	NPC245120
0.8593	High Similarity	NPC474617
0.8582	High Similarity	NPC185066
0.8561	High Similarity	NPC474530
0.8561	High Similarity	NPC20796
0.8561	High Similarity	NPC155963
0.8561	High Similarity	NPC474540
0.8561	High Similarity	NPC474521
0.8552	High Similarity	NPC30688
0.8552	High Similarity	NPC176903
0.8542	High Similarity	NPC15577
0.8542	High Similarity	NPC231149
0.854	High Similarity	NPC167111
0.854	High Similarity	NPC31849
0.854	High Similarity	NPC296624
0.854	High Similarity	NPC318400
0.854	High Similarity	NPC207002
0.854	High Similarity	NPC133956
0.854	High Similarity	NPC471910
0.854	High Similarity	NPC277021
0.8529	High Similarity	NPC37009
0.8529	High Similarity	NPC73738
0.8529	High Similarity	NPC66430
0.8511	High Similarity	NPC152771
0.8511	High Similarity	NPC195357
0.8507	High Similarity	NPC289316
0.8507	High Similarity	NPC194841
0.8507	High Similarity	NPC474670
0.8503	High Similarity	NPC470264
0.8496	Intermediate Similarity	NPC471828
0.8496	Intermediate Similarity	NPC471827
0.8493	Intermediate Similarity	NPC120426
0.8493	Intermediate Similarity	NPC294522
0.8493	Intermediate Similarity	NPC21184
0.8493	Intermediate Similarity	NPC205727
0.8485	Intermediate Similarity	NPC273772
0.8485	Intermediate Similarity	NPC109675
0.8485	Intermediate Similarity	NPC143725
0.8483	Intermediate Similarity	NPC96294
0.8483	Intermediate Similarity	NPC139839
0.8478	Intermediate Similarity	NPC7163
0.8478	Intermediate Similarity	NPC100986
0.8478	Intermediate Similarity	NPC307412
0.8478	Intermediate Similarity	NPC18804
0.8478	Intermediate Similarity	NPC55149
0.8478	Intermediate Similarity	NPC260265
0.8478	Intermediate Similarity	NPC62366
0.8478	Intermediate Similarity	NPC267412
0.8478	Intermediate Similarity	NPC287182
0.8478	Intermediate Similarity	NPC326600
0.8478	Intermediate Similarity	NPC166672
0.8478	Intermediate Similarity	NPC74655
0.8478	Intermediate Similarity	NPC50896
0.8478	Intermediate Similarity	NPC198381
0.8478	Intermediate Similarity	NPC84894
0.8478	Intermediate Similarity	NPC195343
0.8478	Intermediate Similarity	NPC204353
0.8478	Intermediate Similarity	NPC164269
0.8478	Intermediate Similarity	NPC319859
0.8478	Intermediate Similarity	NPC127888
0.8478	Intermediate Similarity	NPC47163
0.8478	Intermediate Similarity	NPC111635
0.8467	Intermediate Similarity	NPC14248
0.8451	Intermediate Similarity	NPC469564
0.8444	Intermediate Similarity	NPC474651
0.8444	Intermediate Similarity	NPC474636
0.8444	Intermediate Similarity	NPC474623
0.844	Intermediate Similarity	NPC312881
0.8435	Intermediate Similarity	NPC213197
0.8433	Intermediate Similarity	NPC127604
0.8433	Intermediate Similarity	NPC163248
0.8433	Intermediate Similarity	NPC471826
0.8429	Intermediate Similarity	NPC474886
0.8429	Intermediate Similarity	NPC232246
0.8429	Intermediate Similarity	NPC225106
0.8429	Intermediate Similarity	NPC294456
0.8429	Intermediate Similarity	NPC212124
0.8429	Intermediate Similarity	NPC184861
0.8429	Intermediate Similarity	NPC153818
0.8429	Intermediate Similarity	NPC38874
0.8429	Intermediate Similarity	NPC281014
0.8421	Intermediate Similarity	NPC27671
0.8421	Intermediate Similarity	NPC201667
0.8421	Intermediate Similarity	NPC73413
0.8417	Intermediate Similarity	NPC33986
0.8417	Intermediate Similarity	NPC472424
0.8417	Intermediate Similarity	NPC471625
0.8417	Intermediate Similarity	NPC281241
0.8417	Intermediate Similarity	NPC471909
0.8417	Intermediate Similarity	NPC469675
0.8417	Intermediate Similarity	NPC86892
0.8417	Intermediate Similarity	NPC73071
0.8414	Intermediate Similarity	NPC476347
0.8414	Intermediate Similarity	NPC178129
0.8409	Intermediate Similarity	NPC194626
0.8406	Intermediate Similarity	NPC474810
0.8406	Intermediate Similarity	NPC222036
0.8406	Intermediate Similarity	NPC83535
0.8406	Intermediate Similarity	NPC7526
0.8394	Intermediate Similarity	NPC29734
0.8382	Intermediate Similarity	NPC168710
0.838	Intermediate Similarity	NPC287286
0.8378	Intermediate Similarity	NPC120774
0.8378	Intermediate Similarity	NPC163598
0.8378	Intermediate Similarity	NPC264875
0.837	Intermediate Similarity	NPC243688
0.837	Intermediate Similarity	NPC474821
0.8367	Intermediate Similarity	NPC114740
0.8357	Intermediate Similarity	NPC177281
0.8357	Intermediate Similarity	NPC476455
0.8357	Intermediate Similarity	NPC128529
0.8357	Intermediate Similarity	NPC78746
0.8357	Intermediate Similarity	NPC188380
0.8357	Intermediate Similarity	NPC160727
0.8357	Intermediate Similarity	NPC55615
0.8357	Intermediate Similarity	NPC283019
0.8357	Intermediate Similarity	NPC224543
0.8357	Intermediate Similarity	NPC149320
0.8357	Intermediate Similarity	NPC471630
0.8356	Intermediate Similarity	NPC476348
0.8356	Intermediate Similarity	NPC48366
0.8356	Intermediate Similarity	NPC187398
0.8346	Intermediate Similarity	NPC173350
0.8346	Intermediate Similarity	NPC290605
0.8346	Intermediate Similarity	NPC154176
0.8346	Intermediate Similarity	NPC472518
0.8345	Intermediate Similarity	NPC253574
0.8345	Intermediate Similarity	NPC98179
0.8333	Intermediate Similarity	NPC194277
0.8333	Intermediate Similarity	NPC471824
0.8333	Intermediate Similarity	NPC474635
0.8333	Intermediate Similarity	NPC144418
0.8333	Intermediate Similarity	NPC185127
0.8333	Intermediate Similarity	NPC310373
0.8321	Intermediate Similarity	NPC113098
0.8321	Intermediate Similarity	NPC476399

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 NPC472521 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	1021
0.2-0.3	1979
0.3-0.4	2636
0.4-0.5	1742
0.5-0.6	908
0.6-0.7	343
0.7-0.8	113
0.8-0.85	33
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8299	Intermediate Similarity	NPD1653	Approved
0.8273	Intermediate Similarity	NPD5124	Phase 1
0.8273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD422	Phase 1
0.7875	Intermediate Similarity	NPD5844	Phase 1
0.7683	Intermediate Similarity	NPD7549	Discontinued
0.7682	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2801	Approved
0.766	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3817	Phase 2
0.7606	Intermediate Similarity	NPD3027	Phase 3
0.7591	Intermediate Similarity	NPD3496	Discontinued
0.7589	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1613	Approved
0.7517	Intermediate Similarity	NPD447	Suspended
0.7517	Intermediate Similarity	NPD1652	Phase 2
0.7484	Intermediate Similarity	NPD919	Approved
0.7468	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD3018	Phase 2
0.7452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5494	Approved
0.7432	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD4626	Approved
0.7389	Intermediate Similarity	NPD6801	Discontinued
0.7389	Intermediate Similarity	NPD1934	Approved
0.7346	Intermediate Similarity	NPD6232	Discontinued
0.7342	Intermediate Similarity	NPD1465	Phase 2
0.7329	Intermediate Similarity	NPD4060	Phase 1
0.731	Intermediate Similarity	NPD7985	Registered
0.731	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2983	Phase 2
0.7305	Intermediate Similarity	NPD2982	Phase 2
0.7299	Intermediate Similarity	NPD7644	Approved
0.7296	Intermediate Similarity	NPD5402	Approved
0.7292	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1247	Approved
0.7273	Intermediate Similarity	NPD2534	Approved
0.7273	Intermediate Similarity	NPD2533	Approved
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2532	Approved
0.725	Intermediate Similarity	NPD3882	Suspended
0.7241	Intermediate Similarity	NPD4625	Phase 3
0.7237	Intermediate Similarity	NPD3750	Approved
0.7234	Intermediate Similarity	NPD2981	Phase 2
0.7233	Intermediate Similarity	NPD7819	Suspended
0.7233	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7473	Discontinued
0.7208	Intermediate Similarity	NPD1511	Approved
0.7208	Intermediate Similarity	NPD6799	Approved
0.7205	Intermediate Similarity	NPD7075	Discontinued
0.7194	Intermediate Similarity	NPD5691	Approved
0.7192	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1296	Phase 2
0.7183	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4749	Approved
0.7179	Intermediate Similarity	NPD920	Approved
0.7179	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5536	Phase 2
0.7172	Intermediate Similarity	NPD4908	Phase 1
0.7171	Intermediate Similarity	NPD6674	Discontinued
0.717	Intermediate Similarity	NPD37	Approved
0.7169	Intermediate Similarity	NPD3818	Discontinued
0.7163	Intermediate Similarity	NPD1611	Approved
0.7162	Intermediate Similarity	NPD230	Phase 1
0.7161	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6671	Approved
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7133	Intermediate Similarity	NPD3225	Approved
0.7133	Intermediate Similarity	NPD3748	Approved
0.7122	Intermediate Similarity	NPD1548	Phase 1
0.7115	Intermediate Similarity	NPD1512	Approved
0.7107	Intermediate Similarity	NPD7411	Suspended
0.7105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4357	Discontinued
0.7097	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2797	Approved
0.7075	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7199	Phase 2
0.7068	Intermediate Similarity	NPD1358	Approved
0.7059	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1243	Approved
0.7059	Intermediate Similarity	NPD2800	Approved
0.7055	Intermediate Similarity	NPD6234	Discontinued
0.7048	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6166	Phase 2
0.7048	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD9697	Approved
0.7044	Intermediate Similarity	NPD4380	Phase 2
0.7044	Intermediate Similarity	NPD6599	Discontinued
0.7042	Intermediate Similarity	NPD1610	Phase 2
0.7037	Intermediate Similarity	NPD7768	Phase 2
0.7024	Intermediate Similarity	NPD7054	Approved
0.7014	Intermediate Similarity	NPD6696	Suspended
0.7013	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1398	Phase 1
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.6993	Remote Similarity	NPD2424	Discontinued
0.6988	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2861	Phase 2
0.6982	Remote Similarity	NPD7472	Approved
0.6982	Remote Similarity	NPD7074	Phase 3
0.6978	Remote Similarity	NPD7340	Approved
0.6974	Remote Similarity	NPD2796	Approved
0.6974	Remote Similarity	NPD1551	Phase 2
0.697	Remote Similarity	NPD8127	Discontinued
0.6968	Remote Similarity	NPD6190	Approved
0.6962	Remote Similarity	NPD5403	Approved
0.6959	Remote Similarity	NPD3268	Approved
0.6943	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5535	Approved
0.6933	Remote Similarity	NPD1933	Approved
0.6933	Remote Similarity	NPD4340	Discontinued
0.6928	Remote Similarity	NPD3540	Phase 1
0.6928	Remote Similarity	NPD7266	Discontinued
0.6923	Remote Similarity	NPD3705	Approved
0.6923	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1091	Approved
0.6918	Remote Similarity	NPD3687	Approved
0.6918	Remote Similarity	NPD3686	Approved
0.6909	Remote Similarity	NPD5677	Discontinued
0.6908	Remote Similarity	NPD4308	Phase 3
0.6903	Remote Similarity	NPD4628	Phase 3
0.6901	Remote Similarity	NPD1778	Approved
0.6901	Remote Similarity	NPD6559	Discontinued
0.6897	Remote Similarity	NPD8651	Approved
0.6894	Remote Similarity	NPD5089	Approved
0.6894	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5090	Approved
0.6892	Remote Similarity	NPD7095	Approved
0.689	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9717	Approved
0.6871	Remote Similarity	NPD5353	Approved
0.6866	Remote Similarity	NPD3134	Approved
0.6863	Remote Similarity	NPD3539	Phase 1
0.6861	Remote Similarity	NPD228	Approved
0.686	Remote Similarity	NPD7808	Phase 3
0.6859	Remote Similarity	NPD2219	Phase 1
0.6846	Remote Similarity	NPD2313	Discontinued
0.6842	Remote Similarity	NPD6797	Phase 2
0.6835	Remote Similarity	NPD5401	Approved
0.6832	Remote Similarity	NPD4675	Approved
0.6832	Remote Similarity	NPD4678	Approved
0.6821	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6005	Phase 3
0.6818	Remote Similarity	NPD6002	Phase 3
0.6818	Remote Similarity	NPD5762	Approved
0.6818	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6004	Phase 3
0.6818	Remote Similarity	NPD5763	Approved
0.6818	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1375	Discontinued
0.6803	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7251	Discontinued
0.68	Remote Similarity	NPD6233	Phase 2
0.6797	Remote Similarity	NPD7033	Discontinued
0.6797	Remote Similarity	NPD2799	Discontinued
0.6797	Remote Similarity	NPD1510	Phase 2
0.6795	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4110	Phase 3
0.6795	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3926	Phase 2
0.6786	Remote Similarity	NPD5242	Approved
0.6776	Remote Similarity	NPD6651	Approved
0.6774	Remote Similarity	NPD1549	Phase 2
0.6772	Remote Similarity	NPD5297	Approved
0.677	Remote Similarity	NPD3226	Approved
0.6765	Remote Similarity	NPD2684	Approved
0.6765	Remote Similarity	NPD7228	Approved
0.6755	Remote Similarity	NPD4307	Phase 2
0.6755	Remote Similarity	NPD1240	Approved
0.6753	Remote Similarity	NPD6099	Approved
0.6753	Remote Similarity	NPD6100	Approved
0.6752	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3267	Approved
0.6735	Remote Similarity	NPD3266	Approved
0.6735	Remote Similarity	NPD1203	Approved
0.6733	Remote Similarity	NPD411	Approved
0.6733	Remote Similarity	NPD6798	Discontinued
0.6732	Remote Similarity	NPD7097	Phase 1
0.6731	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5711	Approved
0.6726	Remote Similarity	NPD7229	Phase 3
0.6726	Remote Similarity	NPD5710	Approved
0.6725	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6832	Phase 2
0.6711	Remote Similarity	NPD6355	Discontinued
0.671	Remote Similarity	NPD2346	Discontinued
0.671	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1552	Clinical (unspecified phase)

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