NPASS Compound

Structure

NPC472522 OpenBabel07101718192D 22 23 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 -0.8660 4.5000 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 1.7321 -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 0.0000 3.0000 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 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 0.0000 4.0000 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 1.7321 -0.0000 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 -0.0000 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 -0.0000 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 -0.8660 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 7 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.13
Volume:	313.608
LogP:	3.339
LogD:	2.968
LogS:	-3.822
# Rotatable Bonds:	5
TPSA:	57.9
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	2.635
Fsp3:	0.353
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:	-4.641
MDCK Permeability:	1.703833731880877e-05
Pgp-inhibitor:	0.076
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	71.8732681274414%
Volume Distribution (VD):	1.174
Pgp-substrate:	21.181751251220703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.786
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.877
CYP2C19-substrate:	0.841
CYP2C9-inhibitor:	0.439
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.203
CYP2D6-substrate:	0.717
CYP3A4-inhibitor:	0.464
CYP3A4-substrate:	0.461

ADMET: Excretion

Clearance (CL):	10.661
Half-life (T1/2):	0.37

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.889
Drug-inuced Liver Injury (DILI):	0.725
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.512
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.359
Carcinogencity:	0.254
Eye Corrosion:	0.003
Eye Irritation:	0.058
Respiratory Toxicity:	0.212

Download Data

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

Natural Product: NPC472522

Natural Product ID:	NPC472522
*Common Name:**	CJYYMPLGDRTQMA-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CJYYMPLGDRTQMA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O5/c1-10(2)6-7-11-14-12(8-9-13(18)22-14)16(20-4)17(21-5)15(11)19-3/h6,8-9H,7H2,1-5H3
SMILES:	CC(=CCC1=C(C(=C(C2=C1OC(=O)C=C2)OC)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426675
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[526682]

☑ 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 NPC472522 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	464
0.1-0.2	1921
0.2-0.3	5161
0.3-0.4	10813
0.4-0.5	6680
0.5-0.6	3949
0.6-0.7	5700
0.7-0.8	5266
0.8-0.85	1911
0.85-0.9	721
0.9-0.95	101
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9612	High Similarity	NPC147030
0.9538	High Similarity	NPC472521
0.947	High Similarity	NPC270256
0.9385	High Similarity	NPC233018
0.9385	High Similarity	NPC36437
0.9385	High Similarity	NPC241341
0.9328	High Similarity	NPC279851
0.9328	High Similarity	NPC472520
0.9318	High Similarity	NPC286843
0.9318	High Similarity	NPC167517
0.9308	High Similarity	NPC319969
0.9308	High Similarity	NPC137669
0.9302	High Similarity	NPC244799
0.9302	High Similarity	NPC240722
0.9242	High Similarity	NPC234865
0.9225	High Similarity	NPC27239
0.9225	High Similarity	NPC123127
0.916	High Similarity	NPC123954
0.9154	High Similarity	NPC19242
0.9037	High Similarity	NPC43500
0.9037	High Similarity	NPC164148
0.9023	High Similarity	NPC474600
0.9023	High Similarity	NPC309953
0.8947	High Similarity	NPC26673
0.8923	High Similarity	NPC474670
0.8905	High Similarity	NPC300611
0.8857	High Similarity	NPC205361
0.8855	High Similarity	NPC474616
0.8849	High Similarity	NPC471763
0.8837	High Similarity	NPC201667
0.8837	High Similarity	NPC73413
0.8824	High Similarity	NPC20511
0.8824	High Similarity	NPC139548
0.8824	High Similarity	NPC76336
0.8824	High Similarity	NPC474521
0.8824	High Similarity	NPC474540
0.8824	High Similarity	NPC474530
0.8824	High Similarity	NPC20796
0.8824	High Similarity	NPC52086
0.8824	High Similarity	NPC148835
0.8824	High Similarity	NPC95162
0.8815	High Similarity	NPC240915
0.8815	High Similarity	NPC73071
0.8806	High Similarity	NPC318400
0.8806	High Similarity	NPC207002
0.8806	High Similarity	NPC471910
0.8806	High Similarity	NPC167111
0.8806	High Similarity	NPC133956
0.8806	High Similarity	NPC296624
0.8779	High Similarity	NPC194841
0.8779	High Similarity	NPC474821
0.8777	High Similarity	NPC7439
0.8777	High Similarity	NPC256555
0.8777	High Similarity	NPC236419
0.8777	High Similarity	NPC110067
0.8777	High Similarity	NPC91492
0.8777	High Similarity	NPC138212
0.8777	High Similarity	NPC34245
0.8769	High Similarity	NPC471827
0.8769	High Similarity	NPC471828
0.876	High Similarity	NPC273772
0.876	High Similarity	NPC50720
0.876	High Similarity	NPC109675
0.876	High Similarity	NPC472518
0.8759	High Similarity	NPC13067
0.875	High Similarity	NPC126682
0.875	High Similarity	NPC82271
0.8741	High Similarity	NPC267412
0.8741	High Similarity	NPC195343
0.8741	High Similarity	NPC74655
0.8741	High Similarity	NPC319859
0.8741	High Similarity	NPC7163
0.8741	High Similarity	NPC84894
0.8741	High Similarity	NPC164269
0.8741	High Similarity	NPC47163
0.8741	High Similarity	NPC127888
0.8741	High Similarity	NPC287182
0.8741	High Similarity	NPC18804
0.8741	High Similarity	NPC198381
0.8741	High Similarity	NPC166672
0.8741	High Similarity	NPC100986
0.8741	High Similarity	NPC260265
0.8741	High Similarity	NPC307412
0.8741	High Similarity	NPC55149
0.8731	High Similarity	NPC14248
0.8722	High Similarity	NPC474617
0.8722	High Similarity	NPC476399
0.8712	High Similarity	NPC474636
0.8712	High Similarity	NPC474651
0.8712	High Similarity	NPC474623
0.8702	High Similarity	NPC474632
0.8702	High Similarity	NPC127604
0.8692	High Similarity	NPC27671
0.8682	High Similarity	NPC248429
0.8682	High Similarity	NPC96286
0.8682	High Similarity	NPC150214
0.8676	High Similarity	NPC86892
0.8676	High Similarity	NPC471909
0.8676	High Similarity	NPC469675
0.8676	High Similarity	NPC281241
0.8676	High Similarity	NPC472424
0.8676	High Similarity	NPC224941
0.8676	High Similarity	NPC471625
0.8676	High Similarity	NPC311430
0.8667	High Similarity	NPC7526
0.8667	High Similarity	NPC222036
0.8662	High Similarity	NPC15577
0.8647	High Similarity	NPC168710
0.8636	High Similarity	NPC289316
0.8613	High Similarity	NPC128529
0.8613	High Similarity	NPC471630
0.8613	High Similarity	NPC476455
0.8613	High Similarity	NPC160727
0.8613	High Similarity	NPC55615
0.8613	High Similarity	NPC283019
0.8613	High Similarity	NPC38099
0.8613	High Similarity	NPC26954
0.8613	High Similarity	NPC149320
0.8613	High Similarity	NPC177281
0.8603	High Similarity	NPC92830
0.8582	High Similarity	NPC80170
0.8571	High Similarity	NPC210674
0.8571	High Similarity	NPC185066
0.8571	High Similarity	NPC199204
0.8571	High Similarity	NPC472519
0.8561	High Similarity	NPC471826
0.8561	High Similarity	NPC163248
0.8551	High Similarity	NPC476171
0.8551	High Similarity	NPC155963
0.855	High Similarity	NPC291899
0.8542	High Similarity	NPC30688
0.8542	High Similarity	NPC176903
0.854	High Similarity	NPC472525
0.8538	High Similarity	NPC288238
0.8538	High Similarity	NPC194626
0.8529	High Similarity	NPC277021
0.8529	High Similarity	NPC31849
0.8493	Intermediate Similarity	NPC470264
0.8489	Intermediate Similarity	NPC211110
0.8489	Intermediate Similarity	NPC279573
0.8489	Intermediate Similarity	NPC151946
0.8485	Intermediate Similarity	NPC202594
0.8485	Intermediate Similarity	NPC232692
0.8483	Intermediate Similarity	NPC294522
0.8483	Intermediate Similarity	NPC21184
0.8483	Intermediate Similarity	NPC205727
0.8483	Intermediate Similarity	NPC120426
0.8478	Intermediate Similarity	NPC283331
0.8473	Intermediate Similarity	NPC143725
0.8472	Intermediate Similarity	NPC96294
0.8472	Intermediate Similarity	NPC139839
0.8467	Intermediate Similarity	NPC62366
0.8467	Intermediate Similarity	NPC204353
0.8467	Intermediate Similarity	NPC50896
0.8467	Intermediate Similarity	NPC213173
0.8467	Intermediate Similarity	NPC224475
0.8467	Intermediate Similarity	NPC180716
0.8467	Intermediate Similarity	NPC326600
0.8462	Intermediate Similarity	NPC144418
0.8456	Intermediate Similarity	NPC5423
0.8456	Intermediate Similarity	NPC19157
0.8456	Intermediate Similarity	NPC137949
0.8456	Intermediate Similarity	NPC245120
0.845	Intermediate Similarity	NPC222175
0.8444	Intermediate Similarity	NPC307042
0.8444	Intermediate Similarity	NPC79184
0.844	Intermediate Similarity	NPC469564
0.8433	Intermediate Similarity	NPC293642
0.8433	Intermediate Similarity	NPC60704
0.8433	Intermediate Similarity	NPC139595
0.8429	Intermediate Similarity	NPC312881
0.8421	Intermediate Similarity	NPC188327
0.8421	Intermediate Similarity	NPC101894
0.8421	Intermediate Similarity	NPC234109
0.8417	Intermediate Similarity	NPC38874
0.8417	Intermediate Similarity	NPC153818
0.8417	Intermediate Similarity	NPC232246
0.8417	Intermediate Similarity	NPC474886
0.8409	Intermediate Similarity	NPC111347
0.8406	Intermediate Similarity	NPC33986
0.8403	Intermediate Similarity	NPC231149
0.8403	Intermediate Similarity	NPC476347
0.8403	Intermediate Similarity	NPC178129
0.8394	Intermediate Similarity	NPC474810
0.8392	Intermediate Similarity	NPC476450
0.8385	Intermediate Similarity	NPC235190
0.8385	Intermediate Similarity	NPC180006
0.8385	Intermediate Similarity	NPC163200
0.8382	Intermediate Similarity	NPC73738
0.838	Intermediate Similarity	NPC230157
0.8378	Intermediate Similarity	NPC186507
0.8372	Intermediate Similarity	NPC308217
0.8372	Intermediate Similarity	NPC298796
0.8369	Intermediate Similarity	NPC152771
0.8369	Intermediate Similarity	NPC287286
0.8369	Intermediate Similarity	NPC195357
0.8367	Intermediate Similarity	NPC264875
0.8367	Intermediate Similarity	NPC120774
0.8367	Intermediate Similarity	NPC163598
0.8358	Intermediate Similarity	NPC243688

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 NPC472522 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	412
0.1-0.2	1007
0.2-0.3	1936
0.3-0.4	2668
0.4-0.5	1730
0.5-0.6	892
0.6-0.7	356
0.7-0.8	108
0.8-0.85	34
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8163	Intermediate Similarity	NPD1653	Approved
0.8129	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD5124	Phase 1
0.8027	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD422	Phase 1
0.7862	Intermediate Similarity	NPD5844	Phase 1
0.7806	Intermediate Similarity	NPD919	Approved
0.7756	Intermediate Similarity	NPD5494	Approved
0.7727	Intermediate Similarity	NPD3817	Phase 2
0.7662	Intermediate Similarity	NPD2801	Approved
0.7643	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1652	Phase 2
0.7595	Intermediate Similarity	NPD1247	Approved
0.7589	Intermediate Similarity	NPD3027	Phase 3
0.7574	Intermediate Similarity	NPD3496	Discontinued
0.7571	Intermediate Similarity	NPD3018	Phase 2
0.7571	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7549	Discontinued
0.7556	Intermediate Similarity	NPD5691	Approved
0.7552	Intermediate Similarity	NPD1613	Approved
0.7552	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1296	Phase 2
0.7518	Intermediate Similarity	NPD1611	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3748	Approved
0.7464	Intermediate Similarity	NPD2981	Phase 2
0.7452	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2935	Discontinued
0.7413	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2983	Phase 2
0.741	Intermediate Similarity	NPD2982	Phase 2
0.7407	Intermediate Similarity	NPD5536	Phase 2
0.7407	Intermediate Similarity	NPD7644	Approved
0.7386	Intermediate Similarity	NPD920	Approved
0.7383	Intermediate Similarity	NPD1243	Approved
0.7379	Intermediate Similarity	NPD447	Suspended
0.7372	Intermediate Similarity	NPD4626	Approved
0.7372	Intermediate Similarity	NPD1934	Approved
0.7368	Intermediate Similarity	NPD5283	Phase 1
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6232	Discontinued
0.7325	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7819	Suspended
0.731	Intermediate Similarity	NPD4060	Phase 1
0.7308	Intermediate Similarity	NPD1358	Approved
0.7303	Intermediate Similarity	NPD6799	Approved
0.7297	Intermediate Similarity	NPD2796	Approved
0.7293	Intermediate Similarity	NPD5535	Approved
0.7292	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD9697	Approved
0.7278	Intermediate Similarity	NPD5402	Approved
0.7267	Intermediate Similarity	NPD6674	Discontinued
0.7266	Intermediate Similarity	NPD3705	Approved
0.7261	Intermediate Similarity	NPD6801	Discontinued
0.7255	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2533	Approved
0.7255	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2532	Approved
0.7255	Intermediate Similarity	NPD2534	Approved
0.7237	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3882	Suspended
0.7219	Intermediate Similarity	NPD3750	Approved
0.7215	Intermediate Similarity	NPD1465	Phase 2
0.7195	Intermediate Similarity	NPD7473	Discontinued
0.719	Intermediate Similarity	NPD1511	Approved
0.7188	Intermediate Similarity	NPD7075	Discontinued
0.7172	Intermediate Similarity	NPD7985	Registered
0.7172	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7153	Intermediate Similarity	NPD4908	Phase 1
0.7152	Intermediate Similarity	NPD3818	Discontinued
0.7152	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6599	Discontinued
0.7125	Intermediate Similarity	NPD4967	Phase 2
0.7125	Intermediate Similarity	NPD4966	Approved
0.7125	Intermediate Similarity	NPD4965	Approved
0.7103	Intermediate Similarity	NPD4625	Phase 3
0.7101	Intermediate Similarity	NPD1548	Phase 1
0.7099	Intermediate Similarity	NPD3134	Approved
0.7099	Intermediate Similarity	NPD5677	Discontinued
0.7097	Intermediate Similarity	NPD1512	Approved
0.7089	Intermediate Similarity	NPD7411	Suspended
0.7086	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3926	Phase 2
0.7073	Intermediate Similarity	NPD5242	Approved
0.7067	Intermediate Similarity	NPD3539	Phase 1
0.7063	Intermediate Similarity	NPD3267	Approved
0.7063	Intermediate Similarity	NPD2797	Approved
0.7063	Intermediate Similarity	NPD3266	Approved
0.7063	Intermediate Similarity	NPD5353	Approved
0.7059	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD8127	Discontinued
0.7042	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4749	Approved
0.7039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6234	Discontinued
0.7034	Intermediate Similarity	NPD6832	Phase 2
0.7032	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6166	Phase 2
0.703	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD230	Phase 1
0.7025	Intermediate Similarity	NPD4380	Phase 2
0.7021	Intermediate Similarity	NPD1610	Phase 2
0.702	Intermediate Similarity	NPD3540	Phase 1
0.7019	Intermediate Similarity	NPD7768	Phase 2
0.7007	Intermediate Similarity	NPD6671	Approved
0.7006	Intermediate Similarity	NPD7054	Approved
0.6993	Remote Similarity	NPD8651	Approved
0.6993	Remote Similarity	NPD3225	Approved
0.6981	Remote Similarity	NPD5090	Approved
0.6981	Remote Similarity	NPD5089	Approved
0.698	Remote Similarity	NPD2653	Approved
0.6974	Remote Similarity	NPD2424	Discontinued
0.6968	Remote Similarity	NPD5297	Approved
0.6968	Remote Similarity	NPD4357	Discontinued
0.6966	Remote Similarity	NPD2861	Phase 2
0.6966	Remote Similarity	NPD2237	Approved
0.6964	Remote Similarity	NPD7472	Approved
0.6964	Remote Similarity	NPD7074	Phase 3
0.6959	Remote Similarity	NPD4307	Phase 2
0.6943	Remote Similarity	NPD5403	Approved
0.6939	Remote Similarity	NPD3268	Approved
0.6939	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2313	Discontinued
0.6928	Remote Similarity	NPD2800	Approved
0.6923	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5401	Approved
0.6913	Remote Similarity	NPD4340	Discontinued
0.6908	Remote Similarity	NPD5762	Approved
0.6908	Remote Similarity	NPD5763	Approved
0.6908	Remote Similarity	NPD7266	Discontinued
0.6899	Remote Similarity	NPD3686	Approved
0.6899	Remote Similarity	NPD3687	Approved
0.6894	Remote Similarity	NPD4585	Approved
0.6892	Remote Similarity	NPD6233	Phase 2
0.6887	Remote Similarity	NPD2799	Discontinued
0.6883	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4110	Phase 3
0.6883	Remote Similarity	NPD4628	Phase 3
0.6883	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6559	Discontinued
0.6879	Remote Similarity	NPD1778	Approved
0.6879	Remote Similarity	NPD17	Approved
0.6875	Remote Similarity	NPD6385	Approved
0.6875	Remote Similarity	NPD6386	Approved
0.6875	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7095	Approved
0.6871	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2684	Approved
0.6859	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1551	Phase 2
0.6842	Remote Similarity	NPD7808	Phase 3
0.6838	Remote Similarity	NPD228	Approved
0.6824	Remote Similarity	NPD6797	Phase 2
0.6824	Remote Similarity	NPD6798	Discontinued
0.6821	Remote Similarity	NPD6111	Discontinued
0.6818	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3146	Approved
0.6815	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5585	Approved
0.6807	Remote Similarity	NPD7229	Phase 3
0.68	Remote Similarity	NPD6355	Discontinued
0.6797	Remote Similarity	NPD1375	Discontinued
0.6797	Remote Similarity	NPD6004	Phase 3
0.6797	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6005	Phase 3
0.6797	Remote Similarity	NPD6002	Phase 3
0.6797	Remote Similarity	NPD2346	Discontinued
0.6797	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7124	Phase 2
0.6788	Remote Similarity	NPD7843	Approved
0.6784	Remote Similarity	NPD7251	Discontinued
0.6783	Remote Similarity	NPD1091	Approved
0.6781	Remote Similarity	NPD1019	Discontinued
0.6781	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1510	Phase 2
0.6776	Remote Similarity	NPD4308	Phase 3
0.6774	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7157	Approved
0.6759	Remote Similarity	NPD6696	Suspended
0.6753	Remote Similarity	NPD1549	Phase 2
0.675	Remote Similarity	NPD3226	Approved
0.6746	Remote Similarity	NPD7228	Approved
0.6739	Remote Similarity	NPD1398	Phase 1
0.6739	Remote Similarity	NPD1241	Discontinued
0.6736	Remote Similarity	NPD9717	Approved
0.6736	Remote Similarity	NPD1608	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