NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.11
Volume:	232.116
LogP:	2.223
LogD:	2.063
LogS:	-2.569
# Rotatable Bonds:	3
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	3.58
Fsp3:	0.538
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:	-4.555
MDCK Permeability:	2.629679329402279e-05
Pgp-inhibitor:	0.92
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	90.59357452392578%
Volume Distribution (VD):	1.366
Pgp-substrate:	4.445646286010742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.751
CYP2C9-inhibitor:	0.84
CYP2C9-substrate:	0.331
CYP2D6-inhibitor:	0.424
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.521

ADMET: Excretion

Clearance (CL):	6.282
Half-life (T1/2):	0.751

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.191
AMES Toxicity:	0.283
Rat Oral Acute Toxicity:	0.39
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.908
Carcinogencity:	0.876
Eye Corrosion:	0.1
Eye Irritation:	0.776
Respiratory Toxicity:	0.822

Download Data

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

Natural Product: NPC473223

Natural Product ID:	NPC473223
*Common Name:**	Methyl (3Ar,7Ar)-2-Acetyl-3A,6,7,7A-Tetrahydro-1H-Indene-4-Carboxylate
IUPAC Name:	methyl (3aR,7aR)-2-acetyl-3a,6,7,7a-tetrahydro-1H-indene-4-carboxylate
Synonyms:
Standard InCHIKey:	XDSHPWKVJIQSAP-SKDRFNHKSA-N
Standard InCHI:	InChI=1S/C13H16O3/c1-8(14)10-6-9-4-3-5-11(12(9)7-10)13(15)16-2/h5,7,9,12H,3-4,6H2,1-2H3/t9-,12+/m1/s1
SMILES:	CC(=O)C1=CC2C(C1)CCC=C2C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL374430
PubChem CID:	44419534
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0001238] Carboxylic acid esters [CHEMONTID:0003628] Alpha,beta-unsaturated carboxylic esters [CHEMONTID:0003626] Enoate 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
NPO283	Ligularia lapathifolia	Species	Asteraceae	Eukaryota	roots	n.a.	n.a.	PMID[17284071]
NPO283	Ligularia lapathifolia	Species	Asteraceae	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
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	46540.0	nM	PMID[508256]
NPT1317	Cell Line	CCRF S-180	Mus musculus	IC50	=	19870.0	nM	PMID[508256]
NPT27	Others	Unspecified		IC50	=	35380.0	nM	PMID[508256]

☑ 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 NPC473223 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	181
0.1-0.2	1304
0.2-0.3	6457
0.3-0.4	15851
0.4-0.5	9975
0.5-0.6	5760
0.6-0.7	2652
0.7-0.8	492
0.8-0.85	21
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8734	High Similarity	NPC475100
0.8553	High Similarity	NPC41780
0.8553	High Similarity	NPC187568
0.85	High Similarity	NPC30486
0.8442	Intermediate Similarity	NPC471220
0.8395	Intermediate Similarity	NPC189311
0.8375	Intermediate Similarity	NPC193198
0.8289	Intermediate Similarity	NPC244166
0.8272	Intermediate Similarity	NPC149869
0.8205	Intermediate Similarity	NPC128276
0.8182	Intermediate Similarity	NPC40353
0.8182	Intermediate Similarity	NPC27205
0.8158	Intermediate Similarity	NPC20025
0.8148	Intermediate Similarity	NPC22611
0.8077	Intermediate Similarity	NPC57744
0.8052	Intermediate Similarity	NPC65650
0.8049	Intermediate Similarity	NPC474359
0.8049	Intermediate Similarity	NPC238197
0.8025	Intermediate Similarity	NPC200513
0.8025	Intermediate Similarity	NPC186276
0.8	Intermediate Similarity	NPC47747
0.8	Intermediate Similarity	NPC5509
0.7975	Intermediate Similarity	NPC299235
0.7901	Intermediate Similarity	NPC282293
0.7901	Intermediate Similarity	NPC471325
0.7882	Intermediate Similarity	NPC226863
0.7882	Intermediate Similarity	NPC215831
0.7875	Intermediate Similarity	NPC178277
0.7875	Intermediate Similarity	NPC150646
0.7857	Intermediate Similarity	NPC220478
0.7848	Intermediate Similarity	NPC97377
0.7848	Intermediate Similarity	NPC472300
0.7848	Intermediate Similarity	NPC65603
0.7848	Intermediate Similarity	NPC316500
0.7841	Intermediate Similarity	NPC53685
0.7821	Intermediate Similarity	NPC193351
0.7821	Intermediate Similarity	NPC226669
0.7821	Intermediate Similarity	NPC138408
0.7821	Intermediate Similarity	NPC155587
0.7805	Intermediate Similarity	NPC178676
0.7792	Intermediate Similarity	NPC276336
0.7791	Intermediate Similarity	NPC73995
0.7778	Intermediate Similarity	NPC74673
0.7778	Intermediate Similarity	NPC276356
0.7778	Intermediate Similarity	NPC195424
0.7778	Intermediate Similarity	NPC302426
0.7778	Intermediate Similarity	NPC69271
0.7778	Intermediate Similarity	NPC271104
0.7765	Intermediate Similarity	NPC312561
0.7765	Intermediate Similarity	NPC477228
0.775	Intermediate Similarity	NPC222210
0.775	Intermediate Similarity	NPC63445
0.7738	Intermediate Similarity	NPC177932
0.7738	Intermediate Similarity	NPC65661
0.7738	Intermediate Similarity	NPC110405
0.7738	Intermediate Similarity	NPC86316
0.7738	Intermediate Similarity	NPC106416
0.7733	Intermediate Similarity	NPC476614
0.7727	Intermediate Similarity	NPC472871
0.7722	Intermediate Similarity	NPC235906
0.7711	Intermediate Similarity	NPC118423
0.7711	Intermediate Similarity	NPC39588
0.7701	Intermediate Similarity	NPC476369
0.7701	Intermediate Similarity	NPC476437
0.7701	Intermediate Similarity	NPC51486
0.7701	Intermediate Similarity	NPC152467
0.7701	Intermediate Similarity	NPC471818
0.7692	Intermediate Similarity	NPC476355
0.7692	Intermediate Similarity	NPC117746
0.7692	Intermediate Similarity	NPC294434
0.7692	Intermediate Similarity	NPC259599
0.7692	Intermediate Similarity	NPC15499
0.7683	Intermediate Similarity	NPC40228
0.7683	Intermediate Similarity	NPC42470
0.7683	Intermediate Similarity	NPC475665
0.7674	Intermediate Similarity	NPC472302
0.7674	Intermediate Similarity	NPC472870
0.7662	Intermediate Similarity	NPC257618
0.7662	Intermediate Similarity	NPC29328
0.7662	Intermediate Similarity	NPC129665
0.7662	Intermediate Similarity	NPC163003
0.7654	Intermediate Similarity	NPC469690
0.7654	Intermediate Similarity	NPC264227
0.7654	Intermediate Similarity	NPC472965
0.7654	Intermediate Similarity	NPC63649
0.7654	Intermediate Similarity	NPC471299
0.7647	Intermediate Similarity	NPC107787
0.764	Intermediate Similarity	NPC148463
0.764	Intermediate Similarity	NPC476596
0.7632	Intermediate Similarity	NPC67608
0.7632	Intermediate Similarity	NPC265574
0.7625	Intermediate Similarity	NPC180290
0.7625	Intermediate Similarity	NPC316324
0.7625	Intermediate Similarity	NPC53581
0.7625	Intermediate Similarity	NPC103987
0.7619	Intermediate Similarity	NPC472865
0.7619	Intermediate Similarity	NPC470918
0.759	Intermediate Similarity	NPC173609
0.759	Intermediate Similarity	NPC268122
0.759	Intermediate Similarity	NPC321289
0.759	Intermediate Similarity	NPC94200
0.759	Intermediate Similarity	NPC100297
0.759	Intermediate Similarity	NPC327969
0.7586	Intermediate Similarity	NPC284561
0.7586	Intermediate Similarity	NPC168131
0.7582	Intermediate Similarity	NPC476253
0.7564	Intermediate Similarity	NPC58956
0.7564	Intermediate Similarity	NPC135703
0.7564	Intermediate Similarity	NPC295633
0.7564	Intermediate Similarity	NPC35656
0.7564	Intermediate Similarity	NPC269206
0.7561	Intermediate Similarity	NPC223904
0.7532	Intermediate Similarity	NPC67183
0.7531	Intermediate Similarity	NPC74410
0.7531	Intermediate Similarity	NPC169095
0.7531	Intermediate Similarity	NPC475994
0.7531	Intermediate Similarity	NPC192006
0.7529	Intermediate Similarity	NPC78089
0.7529	Intermediate Similarity	NPC161957
0.7529	Intermediate Similarity	NPC21471
0.7529	Intermediate Similarity	NPC33570
0.7528	Intermediate Similarity	NPC476598
0.7528	Intermediate Similarity	NPC115021
0.7528	Intermediate Similarity	NPC229976
0.7528	Intermediate Similarity	NPC475657
0.7528	Intermediate Similarity	NPC476597
0.75	Intermediate Similarity	NPC212679
0.75	Intermediate Similarity	NPC222011
0.75	Intermediate Similarity	NPC49019
0.75	Intermediate Similarity	NPC472967
0.75	Intermediate Similarity	NPC123360
0.75	Intermediate Similarity	NPC8062
0.75	Intermediate Similarity	NPC53867
0.75	Intermediate Similarity	NPC470047
0.75	Intermediate Similarity	NPC218477
0.75	Intermediate Similarity	NPC474790
0.75	Intermediate Similarity	NPC470046
0.75	Intermediate Similarity	NPC469595
0.75	Intermediate Similarity	NPC220454
0.75	Intermediate Similarity	NPC474976
0.75	Intermediate Similarity	NPC281942
0.75	Intermediate Similarity	NPC266159
0.75	Intermediate Similarity	NPC232426
0.75	Intermediate Similarity	NPC180886
0.7471	Intermediate Similarity	NPC249889
0.7471	Intermediate Similarity	NPC473658
0.7471	Intermediate Similarity	NPC193843
0.747	Intermediate Similarity	NPC477372
0.747	Intermediate Similarity	NPC325031
0.747	Intermediate Similarity	NPC281949
0.747	Intermediate Similarity	NPC25684
0.747	Intermediate Similarity	NPC301477
0.747	Intermediate Similarity	NPC10276
0.747	Intermediate Similarity	NPC35089
0.7468	Intermediate Similarity	NPC140287
0.7468	Intermediate Similarity	NPC474758
0.7444	Intermediate Similarity	NPC477130
0.7444	Intermediate Similarity	NPC477129
0.7444	Intermediate Similarity	NPC470697
0.7444	Intermediate Similarity	NPC476415
0.7442	Intermediate Similarity	NPC234038
0.7442	Intermediate Similarity	NPC168248
0.7442	Intermediate Similarity	NPC472869
0.7442	Intermediate Similarity	NPC472863
0.7439	Intermediate Similarity	NPC182550
0.7439	Intermediate Similarity	NPC469617
0.7439	Intermediate Similarity	NPC270126
0.7439	Intermediate Similarity	NPC190211
0.7439	Intermediate Similarity	NPC469620
0.7436	Intermediate Similarity	NPC21944
0.7432	Intermediate Similarity	NPC212210
0.7416	Intermediate Similarity	NPC141831
0.7416	Intermediate Similarity	NPC177037
0.7416	Intermediate Similarity	NPC472814
0.7416	Intermediate Similarity	NPC473944
0.7416	Intermediate Similarity	NPC190442
0.7416	Intermediate Similarity	NPC65513
0.7412	Intermediate Similarity	NPC196487
0.7412	Intermediate Similarity	NPC320801
0.7412	Intermediate Similarity	NPC14575
0.7412	Intermediate Similarity	NPC159635
0.7412	Intermediate Similarity	NPC19849
0.7412	Intermediate Similarity	NPC115786
0.7412	Intermediate Similarity	NPC164577
0.7412	Intermediate Similarity	NPC472864
0.7407	Intermediate Similarity	NPC195785
0.7407	Intermediate Similarity	NPC54996
0.7407	Intermediate Similarity	NPC470240
0.7407	Intermediate Similarity	NPC15975
0.7407	Intermediate Similarity	NPC122264
0.7407	Intermediate Similarity	NPC476794
0.7407	Intermediate Similarity	NPC165711
0.7403	Intermediate Similarity	NPC144511
0.7403	Intermediate Similarity	NPC199557
0.7403	Intermediate Similarity	NPC296522
0.7397	Intermediate Similarity	NPC213152
0.7391	Intermediate Similarity	NPC253826
0.7391	Intermediate Similarity	NPC69385
0.7386	Intermediate Similarity	NPC251528
0.7386	Intermediate Similarity	NPC177141

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 NPC473223 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	1837
0.2-0.3	3982
0.3-0.4	2129
0.4-0.5	699
0.5-0.6	257
0.6-0.7	68
0.7-0.8	4
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
0.8025	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD1694	Approved
0.7416	Intermediate Similarity	NPD5693	Phase 1
0.7375	Intermediate Similarity	NPD8039	Approved
0.7273	Intermediate Similarity	NPD6672	Approved
0.7273	Intermediate Similarity	NPD5737	Approved
0.7241	Intermediate Similarity	NPD5330	Approved
0.7241	Intermediate Similarity	NPD7334	Approved
0.7241	Intermediate Similarity	NPD6684	Approved
0.7241	Intermediate Similarity	NPD7521	Approved
0.7241	Intermediate Similarity	NPD7146	Approved
0.7241	Intermediate Similarity	NPD6409	Approved
0.7176	Intermediate Similarity	NPD5209	Approved
0.7079	Intermediate Similarity	NPD6903	Approved
0.7079	Intermediate Similarity	NPD5208	Approved
0.7079	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6080	Approved
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD1695	Approved
0.6966	Remote Similarity	NPD3573	Approved
0.6923	Remote Similarity	NPD5692	Phase 3
0.6923	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD5785	Approved
0.6897	Remote Similarity	NPD5362	Discontinued
0.6883	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4691	Approved
0.6875	Remote Similarity	NPD4747	Approved
0.6854	Remote Similarity	NPD4519	Discontinued
0.6854	Remote Similarity	NPD6098	Approved
0.6854	Remote Similarity	NPD4623	Approved
0.6848	Remote Similarity	NPD5694	Approved
0.6848	Remote Similarity	NPD6050	Approved
0.6809	Remote Similarity	NPD5695	Phase 3
0.6809	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7331	Phase 2
0.679	Remote Similarity	NPD5276	Approved
0.6786	Remote Similarity	NPD4756	Discovery
0.6782	Remote Similarity	NPD4221	Approved
0.6782	Remote Similarity	NPD4223	Phase 3
0.675	Remote Similarity	NPD4137	Phase 3
0.6744	Remote Similarity	NPD4695	Discontinued
0.6742	Remote Similarity	NPD5363	Approved
0.6742	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6629	Remote Similarity	NPD4197	Approved
0.6629	Remote Similarity	NPD3666	Approved
0.6629	Remote Similarity	NPD3665	Phase 1
0.6629	Remote Similarity	NPD3133	Approved
0.6627	Remote Similarity	NPD4687	Approved
0.6627	Remote Similarity	NPD4058	Approved
0.6627	Remote Similarity	NPD5733	Approved
0.6598	Remote Similarity	NPD5696	Approved
0.6596	Remote Similarity	NPD6399	Phase 3
0.6582	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD46	Approved
0.6559	Remote Similarity	NPD6698	Approved
0.6556	Remote Similarity	NPD1696	Phase 3
0.6556	Remote Similarity	NPD5329	Approved
0.6533	Remote Similarity	NPD287	Approved
0.6526	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7900	Approved
0.6526	Remote Similarity	NPD7748	Approved
0.6517	Remote Similarity	NPD7154	Phase 3
0.6489	Remote Similarity	NPD6079	Approved
0.6489	Remote Similarity	NPD7515	Phase 2
0.6484	Remote Similarity	NPD4693	Phase 3
0.6484	Remote Similarity	NPD5280	Approved
0.6484	Remote Similarity	NPD4688	Approved
0.6484	Remote Similarity	NPD4689	Approved
0.6484	Remote Similarity	NPD4138	Approved
0.6484	Remote Similarity	NPD3618	Phase 1
0.6484	Remote Similarity	NPD4694	Approved
0.6484	Remote Similarity	NPD4690	Approved
0.6484	Remote Similarity	NPD5205	Approved
0.6458	Remote Similarity	NPD5654	Approved
0.6456	Remote Similarity	NPD7341	Phase 2
0.6452	Remote Similarity	NPD4753	Phase 2
0.6452	Remote Similarity	NPD6051	Approved
0.6452	Remote Similarity	NPD5328	Approved
0.6444	Remote Similarity	NPD4786	Approved
0.6429	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD7638	Approved
0.6408	Remote Similarity	NPD6686	Approved
0.6404	Remote Similarity	NPD4270	Approved
0.6404	Remote Similarity	NPD3667	Approved
0.6404	Remote Similarity	NPD4269	Approved
0.6392	Remote Similarity	NPD7732	Phase 3
0.6389	Remote Similarity	NPD7115	Discovery
0.6374	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD6404	Discontinued
0.6329	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5959	Approved
0.6327	Remote Similarity	NPD7902	Approved
0.6322	Remote Similarity	NPD3617	Approved
0.6321	Remote Similarity	NPD6053	Discontinued
0.6311	Remote Similarity	NPD5697	Approved
0.6304	Remote Similarity	NPD5786	Approved
0.6304	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5369	Approved
0.6289	Remote Similarity	NPD5210	Approved
0.6289	Remote Similarity	NPD4629	Approved
0.6286	Remote Similarity	NPD6371	Approved
0.6277	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD3668	Phase 3
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD6899	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD4195	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6224	Remote Similarity	NPD5222	Approved
0.6224	Remote Similarity	NPD5221	Approved
0.6224	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6435	Approved
0.622	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6008	Approved
0.6214	Remote Similarity	NPD6675	Approved
0.6214	Remote Similarity	NPD7128	Approved
0.6214	Remote Similarity	NPD5739	Approved
0.6214	Remote Similarity	NPD6402	Approved
0.6211	Remote Similarity	NPD4096	Approved
0.6203	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6014	Approved
0.619	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD6013	Approved
0.618	Remote Similarity	NPD5368	Approved
0.618	Remote Similarity	NPD4252	Approved
0.6176	Remote Similarity	NPD6052	Approved
0.617	Remote Similarity	NPD4518	Approved
0.6162	Remote Similarity	NPD5173	Approved
0.6154	Remote Similarity	NPD5332	Approved
0.6154	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6614	Approved
0.6154	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD5331	Approved
0.6132	Remote Similarity	NPD7102	Approved
0.6132	Remote Similarity	NPD7290	Approved
0.6132	Remote Similarity	NPD6883	Approved
0.6111	Remote Similarity	NPD857	Phase 3
0.6111	Remote Similarity	NPD4790	Discontinued
0.6105	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6101	Approved
0.6095	Remote Similarity	NPD7320	Approved
0.6087	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5211	Phase 2
0.6076	Remote Similarity	NPD4192	Approved
0.6076	Remote Similarity	NPD4193	Approved
0.6076	Remote Similarity	NPD4191	Approved
0.6076	Remote Similarity	NPD4194	Approved
0.6075	Remote Similarity	NPD6617	Approved
0.6075	Remote Similarity	NPD6650	Approved
0.6075	Remote Similarity	NPD6649	Approved
0.6075	Remote Similarity	NPD6869	Approved
0.6075	Remote Similarity	NPD6847	Approved
0.6075	Remote Similarity	NPD8130	Phase 1
0.6061	Remote Similarity	NPD7614	Phase 1
0.6061	Remote Similarity	NPD4697	Phase 3
0.6044	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5286	Approved
0.604	Remote Similarity	NPD4696	Approved
0.604	Remote Similarity	NPD5285	Approved
0.6038	Remote Similarity	NPD6372	Approved
0.6038	Remote Similarity	NPD6373	Approved
0.6027	Remote Similarity	NPD28	Approved
0.6027	Remote Similarity	NPD29	Approved
0.6019	Remote Similarity	NPD8297	Approved
0.6019	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD4820	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4819	Approved
0.6	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5223	Approved
0.5979	Remote Similarity	NPD6411	Approved
0.5978	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4788	Approved
0.5963	Remote Similarity	NPD4632	Approved
0.5962	Remote Similarity	NPD5141	Approved
0.5955	Remote Similarity	NPD4271	Approved
0.5955	Remote Similarity	NPD4268	Approved
0.5934	Remote Similarity	NPD4139	Approved
0.5934	Remote Similarity	NPD4692	Approved
0.5926	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5226	Approved
0.5922	Remote Similarity	NPD5224	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