NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	596.26
Volume:	600.716
LogP:	4.359
LogD:	3.482
LogS:	-4.257
# Rotatable Bonds:	9
TPSA:	134.8
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.212
Synthetic Accessibility Score:	5.61
Fsp3:	0.606
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.261
MDCK Permeability:	4.953008101438172e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.439
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.391
Plasma Protein Binding (PPB):	83.67243194580078%
Volume Distribution (VD):	2.135
Pgp-substrate:	14.114177703857422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.306
CYP2C9-inhibitor:	0.409
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.419
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.903
CYP3A4-substrate:	0.681

ADMET: Excretion

Clearance (CL):	5.383
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.885
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.249
Carcinogencity:	0.078
Eye Corrosion:	0.018
Eye Irritation:	0.032
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC477096

Natural Product ID:	NPC477096
*Common Name:**	(1aR,2S,3R,4aR,6S,7S,7aS,8E,10R,11S,11aS)-1,1,3,6,9-Pentamethyl-2-acetoxy-4a,7a-epoxy-7,11-diacetoxy-10-(benzoyloxy)-1a,2,3,4,4a,5,6,7,7a,10,11,11a-dodecahydro-1H-cyclopenta[a]cyclopropa[f]cycloundecene-4-one
IUPAC Name:	[(1R,3R,4S,5R,7S,8S,9R,10E,12S,13S,14S)-4,8,13-triacetyloxy-3,6,6,10,14-pentamethyl-2-oxo-16-oxatetracyclo[10.3.1.01,12.05,7]hexadec-10-en-9-yl] benzoate
Synonyms:
Standard InCHIKey:	LPVJWXJBZPCDLM-VGVAQDAQSA-N
Standard InCHI:	InChI=1S/C33H40O10/c1-16-14-33-29(41-21(6)36)17(2)15-32(33,43-33)28(37)18(3)26(39-19(4)34)23-24(31(23,7)8)27(40-20(5)35)25(16)42-30(38)22-12-10-9-11-13-22/h9-14,17-18,23-27,29H,15H2,1-8H3/b16-14+/t17-,18+,23-,24+,25+,26+,27-,29-,32-,33-/m0/s1
SMILES:	C[C@H]1C[C@]23C(=O)[C@@H]([C@H]([C@@H]4[C@@H](C4(C)C)[C@@H]([C@@H](/C(=C/[C@@]2([C@H]1OC(=O)C)O3)/C)OC(=O)C5=CC=CC=C5)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44179497
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	aerial parts	Yuanjiang, Yunnan Province, China	2008-APR	PMID[19438253]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[30730729]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	5	ug/ml	PMID[19438253]

☑ 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 NPC477096 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	376
0.1-0.2	1344
0.2-0.3	2851
0.3-0.4	7786
0.4-0.5	12705
0.5-0.6	12930
0.6-0.7	4072
0.7-0.8	463
0.8-0.85	64
0.85-0.9	49
0.9-0.95	44
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477094
0.9781	High Similarity	NPC477095
0.9701	High Similarity	NPC272523
0.9701	High Similarity	NPC325805
0.9627	High Similarity	NPC86772
0.9571	High Similarity	NPC477101
0.9571	High Similarity	NPC477099
0.9571	High Similarity	NPC477097
0.9562	High Similarity	NPC82467
0.9552	High Similarity	NPC194769
0.9552	High Similarity	NPC285221
0.9478	High Similarity	NPC265459
0.9478	High Similarity	NPC475262
0.9478	High Similarity	NPC270364
0.9478	High Similarity	NPC79699
0.9478	High Similarity	NPC290833
0.942	High Similarity	NPC45307
0.9416	High Similarity	NPC473654
0.9416	High Similarity	NPC473497
0.9403	High Similarity	NPC472250
0.9371	High Similarity	NPC477100
0.9371	High Similarity	NPC477098
0.9343	High Similarity	NPC475660
0.9296	High Similarity	NPC25484
0.9296	High Similarity	NPC232583
0.9275	High Similarity	NPC475413
0.9275	High Similarity	NPC474303
0.927	High Similarity	NPC276652
0.9254	High Similarity	NPC477360
0.9155	High Similarity	NPC205389
0.9124	High Similarity	NPC477358
0.9104	High Similarity	NPC475671
0.9104	High Similarity	NPC3450
0.9104	High Similarity	NPC122504
0.9104	High Similarity	NPC475452
0.9104	High Similarity	NPC42234
0.9085	High Similarity	NPC170668
0.9	High Similarity	NPC187566
0.8978	High Similarity	NPC153617
0.8978	High Similarity	NPC477359
0.8929	High Similarity	NPC251294
0.8841	High Similarity	NPC477368
0.8824	High Similarity	NPC475508
0.8777	High Similarity	NPC472247
0.8777	High Similarity	NPC232888
0.8777	High Similarity	NPC477367
0.8768	High Similarity	NPC477364
0.8741	High Similarity	NPC153214
0.8732	High Similarity	NPC242355
0.8696	High Similarity	NPC233860
0.8686	High Similarity	NPC272946
0.8657	High Similarity	NPC8990
0.8643	High Similarity	NPC279637
0.8643	High Similarity	NPC149401
0.8639	High Similarity	NPC125033
0.8633	High Similarity	NPC472248
0.8593	High Similarity	NPC477369
0.8582	High Similarity	NPC202729
0.8571	High Similarity	NPC311492
0.8571	High Similarity	NPC324898
0.8571	High Similarity	NPC298547
0.8571	High Similarity	NPC134937
0.8571	High Similarity	NPC28836
0.8561	High Similarity	NPC239358
0.8521	High Similarity	NPC27721
0.8511	High Similarity	NPC200154
0.8478	Intermediate Similarity	NPC37968
0.8467	Intermediate Similarity	NPC477357
0.8462	Intermediate Similarity	NPC121268
0.8462	Intermediate Similarity	NPC53361
0.8462	Intermediate Similarity	NPC473301
0.8429	Intermediate Similarity	NPC233692
0.8414	Intermediate Similarity	NPC475135
0.8392	Intermediate Similarity	NPC205305
0.8392	Intermediate Similarity	NPC327511
0.8356	Intermediate Similarity	NPC191387
0.8356	Intermediate Similarity	NPC131966
0.8323	Intermediate Similarity	NPC55744
0.8273	Intermediate Similarity	NPC477370
0.8261	Intermediate Similarity	NPC477363
0.8261	Intermediate Similarity	NPC477366
0.8248	Intermediate Similarity	NPC477362
0.8243	Intermediate Similarity	NPC471100
0.8243	Intermediate Similarity	NPC25043
0.8243	Intermediate Similarity	NPC471107
0.8243	Intermediate Similarity	NPC134131
0.8235	Intermediate Similarity	NPC70344
0.8201	Intermediate Similarity	NPC477365
0.8146	Intermediate Similarity	NPC254558
0.8117	Intermediate Similarity	NPC11410
0.8092	Intermediate Similarity	NPC51602
0.8071	Intermediate Similarity	NPC472706
0.8069	Intermediate Similarity	NPC217673
0.8069	Intermediate Similarity	NPC52523
0.8067	Intermediate Similarity	NPC475552
0.8052	Intermediate Similarity	NPC251139
0.8039	Intermediate Similarity	NPC22571
0.8039	Intermediate Similarity	NPC283875
0.8039	Intermediate Similarity	NPC138641
0.8039	Intermediate Similarity	NPC469648
0.8039	Intermediate Similarity	NPC469647
0.8014	Intermediate Similarity	NPC184109
0.8014	Intermediate Similarity	NPC472707
0.8	Intermediate Similarity	NPC127857
0.8	Intermediate Similarity	NPC471162
0.7987	Intermediate Similarity	NPC95449
0.7986	Intermediate Similarity	NPC472704
0.7974	Intermediate Similarity	NPC472398
0.7974	Intermediate Similarity	NPC471103
0.7961	Intermediate Similarity	NPC473403
0.7935	Intermediate Similarity	NPC473670
0.7935	Intermediate Similarity	NPC21410
0.7935	Intermediate Similarity	NPC282239
0.7935	Intermediate Similarity	NPC469456
0.7931	Intermediate Similarity	NPC471911
0.7931	Intermediate Similarity	NPC4242
0.7922	Intermediate Similarity	NPC233581
0.7922	Intermediate Similarity	NPC145649
0.7919	Intermediate Similarity	NPC183540
0.7914	Intermediate Similarity	NPC472703
0.7908	Intermediate Similarity	NPC7095
0.7908	Intermediate Similarity	NPC112216
0.7885	Intermediate Similarity	NPC106895
0.7885	Intermediate Similarity	NPC217091
0.7857	Intermediate Similarity	NPC306799
0.7857	Intermediate Similarity	NPC101043
0.7852	Intermediate Similarity	NPC282973
0.7843	Intermediate Similarity	NPC60509
0.7843	Intermediate Similarity	NPC81698
0.7843	Intermediate Similarity	NPC250046
0.784	Intermediate Similarity	NPC40138
0.7834	Intermediate Similarity	NPC472393
0.7826	Intermediate Similarity	NPC324769
0.7826	Intermediate Similarity	NPC325732
0.7815	Intermediate Similarity	NPC470231
0.78	Intermediate Similarity	NPC182869
0.78	Intermediate Similarity	NPC63737
0.7799	Intermediate Similarity	NPC329997
0.7793	Intermediate Similarity	NPC469499
0.7793	Intermediate Similarity	NPC472394
0.7793	Intermediate Similarity	NPC475569
0.7792	Intermediate Similarity	NPC161239
0.7792	Intermediate Similarity	NPC165260
0.7792	Intermediate Similarity	NPC198455
0.7785	Intermediate Similarity	NPC87934
0.7785	Intermediate Similarity	NPC477904
0.7785	Intermediate Similarity	NPC183270
0.7785	Intermediate Similarity	NPC162613
0.7785	Intermediate Similarity	NPC471102
0.7778	Intermediate Similarity	NPC132652
0.7756	Intermediate Similarity	NPC242262
0.7756	Intermediate Similarity	NPC473414
0.7756	Intermediate Similarity	NPC237549
0.7756	Intermediate Similarity	NPC77719
0.7756	Intermediate Similarity	NPC256142
0.7756	Intermediate Similarity	NPC219419
0.7756	Intermediate Similarity	NPC472030
0.7756	Intermediate Similarity	NPC304876
0.7756	Intermediate Similarity	NPC472005
0.7756	Intermediate Similarity	NPC472022
0.7756	Intermediate Similarity	NPC249471
0.7756	Intermediate Similarity	NPC257213
0.7756	Intermediate Similarity	NPC158333
0.7756	Intermediate Similarity	NPC1173
0.7756	Intermediate Similarity	NPC265395
0.775	Intermediate Similarity	NPC477188
0.775	Intermediate Similarity	NPC477190
0.775	Intermediate Similarity	NPC43304
0.7748	Intermediate Similarity	NPC477894
0.7746	Intermediate Similarity	NPC476599
0.7733	Intermediate Similarity	NPC266374
0.7718	Intermediate Similarity	NPC9905
0.7716	Intermediate Similarity	NPC477491
0.7712	Intermediate Similarity	NPC312393
0.7712	Intermediate Similarity	NPC477737
0.7707	Intermediate Similarity	NPC114357
0.7707	Intermediate Similarity	NPC228204
0.7707	Intermediate Similarity	NPC26033
0.7707	Intermediate Similarity	NPC155329
0.7707	Intermediate Similarity	NPC473611
0.7707	Intermediate Similarity	NPC114410
0.7707	Intermediate Similarity	NPC112523
0.7707	Intermediate Similarity	NPC259144
0.7707	Intermediate Similarity	NPC472549
0.7698	Intermediate Similarity	NPC473243
0.7687	Intermediate Similarity	NPC475277
0.7687	Intermediate Similarity	NPC473522
0.7687	Intermediate Similarity	NPC477093
0.7682	Intermediate Similarity	NPC192658
0.7682	Intermediate Similarity	NPC472546
0.7671	Intermediate Similarity	NPC238370
0.7667	Intermediate Similarity	NPC473440
0.7662	Intermediate Similarity	NPC327031
0.7643	Intermediate Similarity	NPC11588
0.7643	Intermediate Similarity	NPC134685
0.7643	Intermediate Similarity	NPC229545
0.7643	Intermediate Similarity	NPC248265
0.7635	Intermediate Similarity	NPC472577
0.7635	Intermediate Similarity	NPC291638
0.7635	Intermediate Similarity	NPC17877

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 NPC477096 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	857
0.2-0.3	1970
0.3-0.4	3089
0.4-0.5	2043
0.5-0.6	760
0.6-0.7	121
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7853	Intermediate Similarity	NPD7799	Discontinued
0.7763	Intermediate Similarity	NPD7236	Approved
0.7628	Intermediate Similarity	NPD7239	Suspended
0.7619	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7057	Phase 3
0.7195	Intermediate Similarity	NPD7058	Phase 2
0.7153	Intermediate Similarity	NPD2067	Discontinued
0.708	Intermediate Similarity	NPD2182	Approved
0.7052	Intermediate Similarity	NPD8368	Discontinued
0.7052	Intermediate Similarity	NPD7685	Pre-registration
0.7029	Intermediate Similarity	NPD8407	Phase 2
0.7021	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6599	Discontinued
0.6867	Remote Similarity	NPD6085	Phase 2
0.6867	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7961	Discontinued
0.6854	Remote Similarity	NPD8434	Phase 2
0.6854	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6685	Approved
0.6788	Remote Similarity	NPD164	Approved
0.6778	Remote Similarity	NPD8435	Approved
0.6766	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4628	Phase 3
0.6746	Remote Similarity	NPD7075	Discontinued
0.6735	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6799	Approved
0.6685	Remote Similarity	NPD8360	Approved
0.6685	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD6765	Approved
0.6667	Remote Similarity	NPD5760	Phase 2
0.6644	Remote Similarity	NPD6287	Discontinued
0.6643	Remote Similarity	NPD6858	Approved
0.6643	Remote Similarity	NPD7094	Approved
0.6621	Remote Similarity	NPD4198	Discontinued
0.6607	Remote Similarity	NPD6801	Discontinued
0.6599	Remote Similarity	NPD7741	Discontinued
0.6594	Remote Similarity	NPD5765	Approved
0.6585	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD8150	Discontinued
0.6573	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6912	Phase 3
0.6562	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6002	Phase 3
0.6562	Remote Similarity	NPD6004	Phase 3
0.6562	Remote Similarity	NPD6005	Phase 3
0.6562	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD8485	Approved
0.6536	Remote Similarity	NPD5647	Approved
0.6529	Remote Similarity	NPD5402	Approved
0.6529	Remote Similarity	NPD3817	Phase 2
0.6519	Remote Similarity	NPD6784	Approved
0.6519	Remote Similarity	NPD6785	Approved
0.6519	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5403	Approved
0.6503	Remote Similarity	NPD3887	Approved
0.6503	Remote Similarity	NPD6190	Approved
0.6497	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD1238	Approved
0.6486	Remote Similarity	NPD9545	Approved
0.6485	Remote Similarity	NPD5401	Approved
0.6475	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7819	Suspended
0.6456	Remote Similarity	NPD6355	Discontinued
0.6455	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6832	Phase 2
0.6442	Remote Similarity	NPD2575	Approved
0.6432	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6653	Approved
0.6405	Remote Similarity	NPD5667	Approved
0.6398	Remote Similarity	NPD2796	Approved
0.6398	Remote Similarity	NPD7137	Phase 2
0.6379	Remote Similarity	NPD5494	Approved
0.6375	Remote Similarity	NPD2567	Approved
0.6375	Remote Similarity	NPD2569	Approved
0.6369	Remote Similarity	NPD3764	Approved
0.6364	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5762	Approved
0.6358	Remote Similarity	NPD5763	Approved
0.6357	Remote Similarity	NPD6647	Phase 2
0.6352	Remote Similarity	NPD230	Phase 1
0.6347	Remote Similarity	NPD6273	Approved
0.6343	Remote Similarity	NPD8127	Discontinued
0.6335	Remote Similarity	NPD7305	Phase 1
0.6322	Remote Similarity	NPD919	Approved
0.6313	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.631	Remote Similarity	NPD920	Approved
0.631	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7008	Discontinued
0.6301	Remote Similarity	NPD3882	Suspended
0.6299	Remote Similarity	NPD1876	Approved
0.6294	Remote Similarity	NPD4380	Phase 2
0.6287	Remote Similarity	NPD2534	Approved
0.6287	Remote Similarity	NPD2533	Approved
0.6287	Remote Similarity	NPD2532	Approved
0.6275	Remote Similarity	NPD3972	Approved
0.6275	Remote Similarity	NPD6637	Approved
0.6268	Remote Similarity	NPD5048	Discontinued
0.6263	Remote Similarity	NPD8462	Phase 1
0.6258	Remote Similarity	NPD6362	Approved
0.6258	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD2353	Approved
0.6243	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD2799	Discontinued
0.6235	Remote Similarity	NPD7458	Discontinued
0.6235	Remote Similarity	NPD7033	Discontinued
0.623	Remote Similarity	NPD8285	Discontinued
0.6226	Remote Similarity	NPD7713	Phase 3
0.6224	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD4807	Approved
0.6209	Remote Similarity	NPD4806	Approved
0.6207	Remote Similarity	NPD6371	Approved
0.6203	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD7473	Discontinued
0.6197	Remote Similarity	NPD1237	Approved
0.619	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.619	Remote Similarity	NPD642	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7497	Discontinued
0.6184	Remote Similarity	NPD5306	Approved
0.6184	Remote Similarity	NPD5305	Approved
0.6184	Remote Similarity	NPD17	Approved
0.6182	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3926	Phase 2
0.6178	Remote Similarity	NPD3661	Approved
0.6178	Remote Similarity	NPD3664	Approved
0.6178	Remote Similarity	NPD3663	Approved
0.6178	Remote Similarity	NPD3662	Phase 3
0.6171	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD3751	Discontinued
0.6167	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD2313	Discontinued
0.6163	Remote Similarity	NPD6385	Approved
0.6163	Remote Similarity	NPD7411	Suspended
0.6163	Remote Similarity	NPD6386	Approved
0.6159	Remote Similarity	NPD6319	Approved
0.6159	Remote Similarity	NPD1471	Phase 3
0.6159	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD1247	Approved
0.6154	Remote Similarity	NPD8319	Approved
0.6154	Remote Similarity	NPD8320	Phase 1
0.6154	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD4684	Phase 3
0.6149	Remote Similarity	NPD2652	Approved
0.6149	Remote Similarity	NPD2650	Approved
0.6149	Remote Similarity	NPD4686	Approved
0.6149	Remote Similarity	NPD5353	Approved
0.6149	Remote Similarity	NPD4685	Phase 3
0.6145	Remote Similarity	NPD2403	Approved
0.6145	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD7798	Approved
0.6141	Remote Similarity	NPD8313	Approved
0.6141	Remote Similarity	NPD8312	Approved
0.614	Remote Similarity	NPD3226	Approved
0.6139	Remote Similarity	NPD7055	Discontinued
0.6133	Remote Similarity	NPD9493	Approved
0.6127	Remote Similarity	NPD1929	Approved
0.6127	Remote Similarity	NPD1930	Approved
0.6127	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD6663	Approved
0.6125	Remote Similarity	NPD8032	Phase 2
0.6124	Remote Similarity	NPD3787	Discontinued
0.6122	Remote Similarity	NPD969	Suspended
0.6121	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD5585	Approved
0.6115	Remote Similarity	NPD2798	Approved
0.6115	Remote Similarity	NPD1019	Discontinued
0.6114	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD2354	Approved
0.6107	Remote Similarity	NPD5951	Approved
0.6107	Remote Similarity	NPD4766	Approved
0.6096	Remote Similarity	NPD4233	Approved
0.6096	Remote Similarity	NPD4234	Approved
0.6092	Remote Similarity	NPD7972	Discontinued
0.6089	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7808	Phase 3
0.6087	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD1243	Approved
0.6084	Remote Similarity	NPD2800	Approved
0.6077	Remote Similarity	NPD3818	Discontinued
0.6076	Remote Similarity	NPD5736	Approved
0.6071	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD9495	Approved
0.6071	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD1608	Approved
0.6061	Remote Similarity	NPD2346	Discontinued
0.6056	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD6166	Phase 2
0.6056	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD6167	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