NPASS Compound

Structure

NPC474112 OpenBabel07101718312D 27 28 0 0 1 0 0 0 0 0999 V2000 -3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7634 1.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1932 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0592 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3894 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6728 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9253 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5233 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3894 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7913 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6573 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5233 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.6573 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.2955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5768 -0.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 0.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 20 2 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 2 1 1 0 0 0 22 26 1 0 0 0 0 23 3 1 6 0 0 0 23 27 1 0 0 0 0 26 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.26
Volume:	413.866
LogP:	6.106
LogD:	4.387
LogS:	-6.205
# Rotatable Bonds:	12
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.285
Synthetic Accessibility Score:	3.678
Fsp3:	0.696
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.653
MDCK Permeability:	2.6570945919957012e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	96.35272979736328%
Volume Distribution (VD):	1.561
Pgp-substrate:	0.8692183494567871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.216
CYP1A2-substrate:	0.59
CYP2C19-inhibitor:	0.663
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.551
CYP2C9-substrate:	0.683
CYP2D6-inhibitor:	0.343
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.976
CYP3A4-substrate:	0.491

ADMET: Excretion

Clearance (CL):	10.244
Half-life (T1/2):	0.391

ADMET: Toxicity

hERG Blockers:	0.402
Human Hepatotoxicity (H-HT):	0.448
Drug-inuced Liver Injury (DILI):	0.48
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.67
Skin Sensitization:	0.974
Carcinogencity:	0.162
Eye Corrosion:	0.231
Eye Irritation:	0.21
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC474112

Natural Product ID:	NPC474112
*Common Name:**	Epiplakinic Acid E Methyl Ester
IUPAC Name:	methyl 2-[(3R,5S)-3,5-dimethyl-5-(2-methyl-8-phenyloctyl)dioxolan-3-yl]acetate
Synonyms:	Epiplakinic Acid E Methyl Ester
Standard InCHIKey:	RYNXSVDLWWRGRW-MXQSGTKOSA-N
Standard InCHI:	InChI=1S/C23H36O4/c1-19(12-8-5-6-9-13-20-14-10-7-11-15-20)16-22(2)18-23(3,27-26-22)17-21(24)25-4/h7,10-11,14-15,19H,5-6,8-9,12-13,16-18H2,1-4H3/t19?,22-,23-/m0/s1
SMILES:	CC(CCCCCCC1=CC=CC=C1)CC2(CC(OO2)(C)CC(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462107
PubChem CID:	10384925
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO63	Plakinastrella onkodes	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277739]
NPO63	Plakinastrella onkodes	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7807122]
NPO63	Plakinastrella onkodes	Species	Plakinidae	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	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2.0	ug.mL-1	PMID[470446]
NPT168	Cell Line	P388	Mus musculus	IC50	=	2.5	ug.mL-1	PMID[470446]
NPT2	Others	Unspecified		IC50	=	4.6	ug.mL-1	PMID[470446]

☑ 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 NPC474112 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	213
0.1-0.2	872
0.2-0.3	2237
0.3-0.4	8017
0.4-0.5	16826
0.5-0.6	12868
0.6-0.7	1579
0.7-0.8	70
0.8-0.85	7
0.85-0.9	1
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC474820
0.9381	High Similarity	NPC475978
0.9278	High Similarity	NPC94487
0.8641	High Similarity	NPC474111
0.8641	High Similarity	NPC329705
0.8542	High Similarity	NPC84288
0.85	High Similarity	NPC271475
0.84	Intermediate Similarity	NPC477767
0.8095	Intermediate Similarity	NPC19136
0.7714	Intermediate Similarity	NPC7435
0.77	Intermediate Similarity	NPC231591
0.7629	Intermediate Similarity	NPC288903
0.7629	Intermediate Similarity	NPC44830
0.7553	Intermediate Similarity	NPC145898
0.7524	Intermediate Similarity	NPC226041
0.75	Intermediate Similarity	NPC94425
0.75	Intermediate Similarity	NPC138798
0.7478	Intermediate Similarity	NPC210531
0.7475	Intermediate Similarity	NPC294134
0.7449	Intermediate Similarity	NPC270507
0.744	Intermediate Similarity	NPC469499
0.7417	Intermediate Similarity	NPC108286
0.7383	Intermediate Similarity	NPC221825
0.7383	Intermediate Similarity	NPC476042
0.7368	Intermediate Similarity	NPC477475
0.7368	Intermediate Similarity	NPC477476
0.7364	Intermediate Similarity	NPC474307
0.7353	Intermediate Similarity	NPC9822
0.7347	Intermediate Similarity	NPC103387
0.7347	Intermediate Similarity	NPC323103
0.7327	Intermediate Similarity	NPC322387
0.7321	Intermediate Similarity	NPC40178
0.732	Intermediate Similarity	NPC127343
0.7315	Intermediate Similarity	NPC225079
0.7315	Intermediate Similarity	NPC264728
0.7304	Intermediate Similarity	NPC294458
0.73	Intermediate Similarity	NPC475710
0.7297	Intermediate Similarity	NPC193640
0.7297	Intermediate Similarity	NPC25385
0.7297	Intermediate Similarity	NPC85560
0.7297	Intermediate Similarity	NPC475905
0.7297	Intermediate Similarity	NPC244933
0.729	Intermediate Similarity	NPC145052
0.7288	Intermediate Similarity	NPC64340
0.7282	Intermediate Similarity	NPC70940
0.7282	Intermediate Similarity	NPC86670
0.7282	Intermediate Similarity	NPC274455
0.7273	Intermediate Similarity	NPC472703
0.7255	Intermediate Similarity	NPC329064
0.7241	Intermediate Similarity	NPC473869
0.7236	Intermediate Similarity	NPC79608
0.7236	Intermediate Similarity	NPC476033
0.7232	Intermediate Similarity	NPC47536
0.7232	Intermediate Similarity	NPC20485
0.7222	Intermediate Similarity	NPC60825
0.7222	Intermediate Similarity	NPC291419
0.7213	Intermediate Similarity	NPC472704
0.7212	Intermediate Similarity	NPC187725
0.7212	Intermediate Similarity	NPC141607
0.7207	Intermediate Similarity	NPC321670
0.7156	Intermediate Similarity	NPC158623
0.7154	Intermediate Similarity	NPC317163
0.7143	Intermediate Similarity	NPC3450
0.7143	Intermediate Similarity	NPC475671
0.7143	Intermediate Similarity	NPC121800
0.7143	Intermediate Similarity	NPC475452
0.7143	Intermediate Similarity	NPC122504
0.713	Intermediate Similarity	NPC179411
0.713	Intermediate Similarity	NPC120393
0.7129	Intermediate Similarity	NPC95965
0.7119	Intermediate Similarity	NPC190298
0.71	Intermediate Similarity	NPC477770
0.71	Intermediate Similarity	NPC285773
0.7097	Intermediate Similarity	NPC473082
0.7073	Intermediate Similarity	NPC8990
0.7073	Intermediate Similarity	NPC236981
0.7069	Intermediate Similarity	NPC469547
0.7064	Intermediate Similarity	NPC54647
0.7059	Intermediate Similarity	NPC84129
0.7059	Intermediate Similarity	NPC61651
0.7048	Intermediate Similarity	NPC86987
0.7041	Intermediate Similarity	NPC170484
0.704	Intermediate Similarity	NPC146239
0.704	Intermediate Similarity	NPC472706
0.7037	Intermediate Similarity	NPC469892
0.7037	Intermediate Similarity	NPC469891
0.7037	Intermediate Similarity	NPC469890
0.7034	Intermediate Similarity	NPC149691
0.7034	Intermediate Similarity	NPC260886
0.7025	Intermediate Similarity	NPC474223
0.7025	Intermediate Similarity	NPC280827
0.7025	Intermediate Similarity	NPC475804
0.7025	Intermediate Similarity	NPC243059
0.7025	Intermediate Similarity	NPC475827
0.7025	Intermediate Similarity	NPC474222
0.7023	Intermediate Similarity	NPC86772
0.7018	Intermediate Similarity	NPC475006
0.7018	Intermediate Similarity	NPC469636
0.7016	Intermediate Similarity	NPC477369
0.701	Intermediate Similarity	NPC240170
0.701	Intermediate Similarity	NPC120776
0.7009	Intermediate Similarity	NPC87069
0.7009	Intermediate Similarity	NPC206764
0.7009	Intermediate Similarity	NPC307651
0.7008	Intermediate Similarity	NPC475508
0.7008	Intermediate Similarity	NPC147561
0.7	Intermediate Similarity	NPC473325
0.7	Intermediate Similarity	NPC133809
0.7	Intermediate Similarity	NPC128248
0.7	Intermediate Similarity	NPC473860
0.7	Intermediate Similarity	NPC136810
0.6992	Remote Similarity	NPC187566
0.6992	Remote Similarity	NPC469927
0.6984	Remote Similarity	NPC268607
0.6983	Remote Similarity	NPC280789
0.697	Remote Similarity	NPC272523
0.697	Remote Similarity	NPC325805
0.6964	Remote Similarity	NPC329282
0.696	Remote Similarity	NPC121272
0.696	Remote Similarity	NPC470816
0.696	Remote Similarity	NPC477366
0.696	Remote Similarity	NPC470818
0.6953	Remote Similarity	NPC471334
0.6949	Remote Similarity	NPC29607
0.6944	Remote Similarity	NPC469893
0.6944	Remote Similarity	NPC261947
0.6939	Remote Similarity	NPC103488
0.6935	Remote Similarity	NPC477362
0.6929	Remote Similarity	NPC69496
0.6923	Remote Similarity	NPC477693
0.6923	Remote Similarity	NPC472250
0.6923	Remote Similarity	NPC153617
0.6923	Remote Similarity	NPC477245
0.6923	Remote Similarity	NPC477246
0.6923	Remote Similarity	NPC477704
0.6917	Remote Similarity	NPC471553
0.6917	Remote Similarity	NPC152812
0.6917	Remote Similarity	NPC268930
0.6911	Remote Similarity	NPC369
0.6911	Remote Similarity	NPC293831
0.6909	Remote Similarity	NPC325497
0.6905	Remote Similarity	NPC253681
0.6905	Remote Similarity	NPC477357
0.6905	Remote Similarity	NPC477365
0.6905	Remote Similarity	NPC473423
0.6905	Remote Similarity	NPC48992
0.6894	Remote Similarity	NPC474726
0.6894	Remote Similarity	NPC475955
0.6894	Remote Similarity	NPC184109
0.6891	Remote Similarity	NPC9274
0.6887	Remote Similarity	NPC317645
0.6887	Remote Similarity	NPC476484
0.6881	Remote Similarity	NPC270654
0.6881	Remote Similarity	NPC103048
0.688	Remote Similarity	NPC478108
0.688	Remote Similarity	NPC472694
0.688	Remote Similarity	NPC246166
0.688	Remote Similarity	NPC472693
0.688	Remote Similarity	NPC473083
0.6875	Remote Similarity	NPC474365
0.6875	Remote Similarity	NPC329556
0.6875	Remote Similarity	NPC301943
0.687	Remote Similarity	NPC290833
0.687	Remote Similarity	NPC270364
0.687	Remote Similarity	NPC475262
0.687	Remote Similarity	NPC265459
0.687	Remote Similarity	NPC79699
0.687	Remote Similarity	NPC469511
0.6869	Remote Similarity	NPC272260
0.6866	Remote Similarity	NPC473497
0.6866	Remote Similarity	NPC474303
0.6866	Remote Similarity	NPC77493
0.6866	Remote Similarity	NPC475413
0.6864	Remote Similarity	NPC172525
0.6857	Remote Similarity	NPC220893
0.6855	Remote Similarity	NPC474254
0.6855	Remote Similarity	NPC474159
0.685	Remote Similarity	NPC477370
0.6846	Remote Similarity	NPC15850
0.6846	Remote Similarity	NPC144257
0.6842	Remote Similarity	NPC94751
0.6842	Remote Similarity	NPC142326
0.6842	Remote Similarity	NPC477251
0.6842	Remote Similarity	NPC74458
0.6838	Remote Similarity	NPC82899
0.6838	Remote Similarity	NPC471912
0.6838	Remote Similarity	NPC270699
0.6838	Remote Similarity	NPC80895
0.6838	Remote Similarity	NPC218855
0.6837	Remote Similarity	NPC298023
0.6837	Remote Similarity	NPC9796
0.6829	Remote Similarity	NPC50872
0.6829	Remote Similarity	NPC37641
0.6829	Remote Similarity	NPC311175
0.6825	Remote Similarity	NPC100402
0.6825	Remote Similarity	NPC9180
0.6825	Remote Similarity	NPC477363
0.6818	Remote Similarity	NPC285221
0.6818	Remote Similarity	NPC194769
0.6807	Remote Similarity	NPC221275

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 NPC474112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	757
0.2-0.3	1524
0.3-0.4	3223
0.4-0.5	2431
0.5-0.6	856
0.6-0.7	164
0.7-0.8	21
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
0.8019	Intermediate Similarity	NPD5048	Discontinued
0.78	Intermediate Similarity	NPD3672	Approved
0.78	Intermediate Similarity	NPD3673	Approved
0.7778	Intermediate Similarity	NPD6685	Approved
0.77	Intermediate Similarity	NPD5346	Phase 2
0.77	Intermediate Similarity	NPD5347	Phase 2
0.7664	Intermediate Similarity	NPD5765	Approved
0.766	Intermediate Similarity	NPD227	Approved
0.766	Intermediate Similarity	NPD225	Approved
0.7573	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7798	Approved
0.75	Intermediate Similarity	NPD1087	Approved
0.75	Intermediate Similarity	NPD4793	Discontinued
0.7423	Intermediate Similarity	NPD226	Approved
0.7381	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD800	Approved
0.7333	Intermediate Similarity	NPD1693	Approved
0.7304	Intermediate Similarity	NPD2652	Approved
0.7304	Intermediate Similarity	NPD2650	Approved
0.7282	Intermediate Similarity	NPD1089	Approved
0.7282	Intermediate Similarity	NPD1086	Approved
0.7282	Intermediate Similarity	NPD1090	Approved
0.7281	Intermediate Similarity	NPD6912	Phase 3
0.7264	Intermediate Similarity	NPD1989	Approved
0.7216	Intermediate Similarity	NPD9490	Approved
0.7182	Intermediate Similarity	NPD6647	Phase 2
0.7143	Intermediate Similarity	NPD1088	Approved
0.71	Intermediate Similarity	NPD9491	Approved
0.7069	Intermediate Similarity	NPD6858	Approved
0.7069	Intermediate Similarity	NPD7094	Approved
0.7064	Intermediate Similarity	NPD2066	Phase 3
0.7027	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6637	Approved
0.6964	Remote Similarity	NPD5909	Discontinued
0.6957	Remote Similarity	NPD2067	Discontinued
0.6929	Remote Similarity	NPD2613	Approved
0.6917	Remote Similarity	NPD6065	Approved
0.6916	Remote Similarity	NPD1563	Approved
0.6897	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD3317	Approved
0.6875	Remote Similarity	NPD1929	Approved
0.6875	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1930	Approved
0.6864	Remote Similarity	NPD6010	Discontinued
0.6842	Remote Similarity	NPD467	Phase 1
0.6807	Remote Similarity	NPD1711	Phase 2
0.6774	Remote Similarity	NPD2609	Approved
0.6774	Remote Similarity	NPD2611	Approved
0.6774	Remote Similarity	NPD2612	Approved
0.6774	Remote Similarity	NPD4217	Approved
0.6774	Remote Similarity	NPD4218	Approved
0.6774	Remote Similarity	NPD4215	Approved
0.6774	Remote Similarity	NPD3132	Approved
0.6774	Remote Similarity	NPD2610	Approved
0.6774	Remote Similarity	NPD3131	Approved
0.6774	Remote Similarity	NPD2608	Approved
0.6774	Remote Similarity	NPD4216	Approved
0.6769	Remote Similarity	NPD2573	Approved
0.6769	Remote Similarity	NPD2566	Approved
0.6769	Remote Similarity	NPD3615	Approved
0.6769	Remote Similarity	NPD3087	Approved
0.6769	Remote Similarity	NPD3614	Approved
0.6769	Remote Similarity	NPD4746	Phase 3
0.6769	Remote Similarity	NPD2574	Discontinued
0.6769	Remote Similarity	NPD2570	Approved
0.6769	Remote Similarity	NPD3616	Approved
0.6769	Remote Similarity	NPD2571	Approved
0.6769	Remote Similarity	NPD4745	Approved
0.6769	Remote Similarity	NPD3088	Approved
0.6769	Remote Similarity	NPD3090	Approved
0.6769	Remote Similarity	NPD3089	Approved
0.6769	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD1239	Approved
0.6727	Remote Similarity	NPD1565	Approved
0.6727	Remote Similarity	NPD1564	Approved
0.6727	Remote Similarity	NPD1566	Phase 3
0.6697	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4685	Phase 3
0.6667	Remote Similarity	NPD4684	Phase 3
0.6667	Remote Similarity	NPD4233	Approved
0.6667	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD4234	Approved
0.6667	Remote Similarity	NPD4766	Approved
0.6667	Remote Similarity	NPD1317	Discontinued
0.6667	Remote Similarity	NPD4686	Approved
0.6641	Remote Similarity	NPD6085	Phase 2
0.6641	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD1932	Approved
0.6636	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD17	Approved
0.661	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1202	Approved
0.6581	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2329	Discontinued
0.6581	Remote Similarity	NPD2182	Approved
0.6549	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5278	Discontinued
0.6522	Remote Similarity	NPD164	Approved
0.6519	Remote Similarity	NPD7033	Discontinued
0.6518	Remote Similarity	NPD5926	Approved
0.6518	Remote Similarity	NPD9495	Approved
0.6518	Remote Similarity	NPD253	Approved
0.6514	Remote Similarity	NPD7631	Approved
0.6504	Remote Similarity	NPD2116	Approved
0.6504	Remote Similarity	NPD2117	Pre-registration
0.6504	Remote Similarity	NPD2115	Approved
0.65	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3643	Approved
0.6471	Remote Similarity	NPD3642	Approved
0.6471	Remote Similarity	NPD3644	Approved
0.6457	Remote Similarity	NPD1608	Approved
0.6455	Remote Similarity	NPD1066	Discontinued
0.6454	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2994	Approved
0.6439	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD4576	Approved
0.6423	Remote Similarity	NPD4574	Approved
0.6422	Remote Similarity	NPD7609	Phase 3
0.6415	Remote Similarity	NPD9259	Approved
0.6415	Remote Similarity	NPD9257	Approved
0.64	Remote Similarity	NPD3032	Approved
0.64	Remote Similarity	NPD3031	Approved
0.64	Remote Similarity	NPD3030	Approved
0.6393	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD1756	Approved
0.6387	Remote Similarity	NPD1752	Approved
0.6387	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4807	Approved
0.6378	Remote Similarity	NPD4806	Approved
0.6364	Remote Similarity	NPD2607	Approved
0.6349	Remote Similarity	NPD5306	Approved
0.6349	Remote Similarity	NPD5305	Approved
0.6321	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.632	Remote Similarity	NPD9545	Approved
0.632	Remote Similarity	NPD4479	Discontinued
0.6316	Remote Similarity	NPD1238	Approved
0.6311	Remote Similarity	NPD1374	Approved
0.6311	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1371	Approved
0.6311	Remote Similarity	NPD1370	Approved
0.6311	Remote Similarity	NPD1373	Approved
0.6311	Remote Similarity	NPD3598	Phase 3
0.6304	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6004	Phase 3
0.6304	Remote Similarity	NPD6005	Phase 3
0.6304	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6002	Phase 3
0.6299	Remote Similarity	NPD2946	Phase 2
0.6296	Remote Similarity	NPD531	Approved
0.6286	Remote Similarity	NPD2575	Approved
0.6283	Remote Similarity	NPD9566	Approved
0.627	Remote Similarity	NPD5981	Approved
0.6269	Remote Similarity	NPD7961	Discontinued
0.626	Remote Similarity	NPD1246	Approved
0.625	Remote Similarity	NPD5239	Approved
0.625	Remote Similarity	NPD942	Approved
0.625	Remote Similarity	NPD5240	Approved
0.625	Remote Similarity	NPD5235	Approved
0.625	Remote Similarity	NPD6287	Discontinued
0.625	Remote Similarity	NPD5237	Approved
0.625	Remote Similarity	NPD5236	Approved
0.624	Remote Similarity	NPD7610	Discontinued
0.6232	Remote Similarity	NPD7137	Phase 2
0.6216	Remote Similarity	NPD5778	Approved
0.6216	Remote Similarity	NPD5779	Approved
0.6212	Remote Similarity	NPD3661	Approved
0.6212	Remote Similarity	NPD3662	Phase 3
0.6212	Remote Similarity	NPD3663	Approved
0.6212	Remote Similarity	NPD3664	Approved
0.621	Remote Similarity	NPD4198	Discontinued
0.6204	Remote Similarity	NPD2567	Approved
0.6204	Remote Similarity	NPD1282	Approved
0.6204	Remote Similarity	NPD2569	Approved
0.6198	Remote Similarity	NPD2201	Approved
0.6194	Remote Similarity	NPD3764	Approved
0.619	Remote Similarity	NPD2617	Discontinued
0.619	Remote Similarity	NPD7741	Discontinued
0.6182	Remote Similarity	NPD9256	Approved
0.6182	Remote Similarity	NPD9258	Approved
0.6179	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD4106	Approved
0.6172	Remote Similarity	NPD4135	Approved
0.6172	Remote Similarity	NPD4136	Approved
0.6165	Remote Similarity	NPD6832	Phase 2
0.6161	Remote Similarity	NPD3718	Approved
0.6161	Remote Similarity	NPD3719	Approved
0.616	Remote Similarity	NPD9493	Approved
0.6159	Remote Similarity	NPD7305	Phase 1
0.6154	Remote Similarity	NPD9261	Approved
0.6148	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD4105	Approved
0.6142	Remote Similarity	NPD4102	Approved
0.614	Remote Similarity	NPD3495	Discontinued
0.6134	Remote Similarity	NPD5706	Approved
0.6134	Remote Similarity	NPD5704	Approved
0.6134	Remote Similarity	NPD5705	Approved
0.6132	Remote Similarity	NPD3971	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