NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	2.283
LogD:	2.429
LogS:	-2.816
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	4.315
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.657
MDCK Permeability:	3.0722145311301574e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.63
30% Bioavailability (F30%):	0.062

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	87.14112091064453%
Volume Distribution (VD):	0.82
Pgp-substrate:	11.405433654785156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.347
CYP1A2-substrate:	0.531
CYP2C19-inhibitor:	0.345
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.319
CYP2C9-substrate:	0.297
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.721
CYP3A4-substrate:	0.453

ADMET: Excretion

Clearance (CL):	13.343
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.403
Drug-inuced Liver Injury (DILI):	0.523
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.556
Maximum Recommended Daily Dose:	0.785
Skin Sensitization:	0.807
Carcinogencity:	0.867
Eye Corrosion:	0.804
Eye Irritation:	0.931
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC290508

Natural Product ID:	NPC290508
*Common Name:**	2,3-Dihydroaromaticin
IUPAC Name:	(3aR,5R,5aS,8aS,9aR)-5,8a-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,7-b]furan-2,8-dione
Synonyms:	2,3-Dihydroaromaticin
Standard InCHIKey:	DCKYPAZZUYXYTC-GCJOFGIHSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h8,10-12H,2,4-7H2,1,3H3/t8-,10-,11+,12-,15+/m1/s1
SMILES:	C[C@@H]1C[C@@H]2[C@H](C[C@@]3(C)[C@H]1CCC3=O)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL359555
PubChem CID:	44398509
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0002046] Ambrosanolides and secoambrosanolides

*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
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	whole plant	Changshou County, Chongqing, China	2008-Aug	PMID[21109433]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO32892	inula peacockiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13411	Senecio cissampelinus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12763	Arnica cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14400	Sideritis congesta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11891	Podocarpus macrophylla	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13707	Strychnos scheffleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6218	Pharyngodictyon cauliflos	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10668	Andryala cedretorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14294	Cussonia vantsilana	Species	Araliaceae	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	5
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	3
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3.9	ug.mL-1	PMID[558684]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	400.0	nM	PMID[558685]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	50.0	uM	PMID[558682]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	50.0	uM	PMID[558683]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[558686]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[558686]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[558686]

☑ 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 NPC290508 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	239
0.1-0.2	2072
0.2-0.3	8948
0.3-0.4	15383
0.4-0.5	8568
0.5-0.6	5644
0.6-0.7	1507
0.7-0.8	248
0.8-0.85	63
0.85-0.9	16
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC73052
1.0	High Similarity	NPC293418
0.961	High Similarity	NPC54468
0.9595	High Similarity	NPC208223
0.9474	High Similarity	NPC6823
0.925	High Similarity	NPC238593
0.9189	High Similarity	NPC320537
0.9189	High Similarity	NPC143979
0.8916	High Similarity	NPC12872
0.8916	High Similarity	NPC168679
0.8889	High Similarity	NPC161957
0.878	High Similarity	NPC309757
0.878	High Similarity	NPC236692
0.8734	High Similarity	NPC74673
0.8734	High Similarity	NPC69271
0.8706	High Similarity	NPC286341
0.8706	High Similarity	NPC191339
0.8675	High Similarity	NPC201658
0.8675	High Similarity	NPC118601
0.8649	High Similarity	NPC5714
0.8642	High Similarity	NPC39588
0.8642	High Similarity	NPC215294
0.8625	High Similarity	NPC47635
0.8625	High Similarity	NPC10276
0.8625	High Similarity	NPC35089
0.8608	High Similarity	NPC182550
0.8605	High Similarity	NPC200237
0.8605	High Similarity	NPC153590
0.8571	High Similarity	NPC178875
0.8554	High Similarity	NPC56593
0.8519	High Similarity	NPC246076
0.85	High Similarity	NPC276356
0.8452	Intermediate Similarity	NPC270270
0.8452	Intermediate Similarity	NPC24728
0.8434	Intermediate Similarity	NPC21471
0.8434	Intermediate Similarity	NPC33570
0.8415	Intermediate Similarity	NPC245665
0.8391	Intermediate Similarity	NPC473234
0.8391	Intermediate Similarity	NPC308656
0.8391	Intermediate Similarity	NPC473273
0.8391	Intermediate Similarity	NPC60386
0.8391	Intermediate Similarity	NPC473263
0.8353	Intermediate Similarity	NPC471149
0.8315	Intermediate Similarity	NPC142529
0.8315	Intermediate Similarity	NPC91771
0.8295	Intermediate Similarity	NPC473331
0.8276	Intermediate Similarity	NPC74103
0.8276	Intermediate Similarity	NPC123177
0.8276	Intermediate Similarity	NPC70595
0.8276	Intermediate Similarity	NPC150978
0.8272	Intermediate Similarity	NPC302426
0.8272	Intermediate Similarity	NPC51507
0.8256	Intermediate Similarity	NPC155935
0.8256	Intermediate Similarity	NPC283409
0.8214	Intermediate Similarity	NPC284534
0.8214	Intermediate Similarity	NPC204105
0.8214	Intermediate Similarity	NPC300082
0.8161	Intermediate Similarity	NPC253144
0.8161	Intermediate Similarity	NPC35809
0.8161	Intermediate Similarity	NPC297474
0.8161	Intermediate Similarity	NPC54065
0.8148	Intermediate Similarity	NPC469690
0.8148	Intermediate Similarity	NPC469620
0.8125	Intermediate Similarity	NPC65603
0.8118	Intermediate Similarity	NPC304558
0.8118	Intermediate Similarity	NPC64153
0.8108	Intermediate Similarity	NPC157518
0.8101	Intermediate Similarity	NPC138408
0.8101	Intermediate Similarity	NPC193351
0.8101	Intermediate Similarity	NPC226669
0.8095	Intermediate Similarity	NPC156485
0.8095	Intermediate Similarity	NPC194859
0.8095	Intermediate Similarity	NPC224386
0.8068	Intermediate Similarity	NPC133888
0.8068	Intermediate Similarity	NPC29821
0.8068	Intermediate Similarity	NPC171360
0.8068	Intermediate Similarity	NPC293001
0.8068	Intermediate Similarity	NPC57304
0.8068	Intermediate Similarity	NPC63193
0.8068	Intermediate Similarity	NPC284185
0.8068	Intermediate Similarity	NPC35959
0.8049	Intermediate Similarity	NPC223904
0.8023	Intermediate Similarity	NPC190753
0.8022	Intermediate Similarity	NPC108475
0.8022	Intermediate Similarity	NPC170143
0.8022	Intermediate Similarity	NPC213947
0.8	Intermediate Similarity	NPC193645
0.8	Intermediate Similarity	NPC48803
0.8	Intermediate Similarity	NPC235792
0.8	Intermediate Similarity	NPC110405
0.8	Intermediate Similarity	NPC275960
0.8	Intermediate Similarity	NPC90121
0.8	Intermediate Similarity	NPC163228
0.7978	Intermediate Similarity	NPC135776
0.7976	Intermediate Similarity	NPC194637
0.7975	Intermediate Similarity	NPC469643
0.7975	Intermediate Similarity	NPC469641
0.7957	Intermediate Similarity	NPC171759
0.7952	Intermediate Similarity	NPC38642
0.7931	Intermediate Similarity	NPC207114
0.7931	Intermediate Similarity	NPC79549
0.7931	Intermediate Similarity	NPC217983
0.7907	Intermediate Similarity	NPC187661
0.7907	Intermediate Similarity	NPC107787
0.7907	Intermediate Similarity	NPC67493
0.7907	Intermediate Similarity	NPC470242
0.7901	Intermediate Similarity	NPC476794
0.7901	Intermediate Similarity	NPC195785
0.7901	Intermediate Similarity	NPC122264
0.7901	Intermediate Similarity	NPC15975
0.7901	Intermediate Similarity	NPC470240
0.7882	Intermediate Similarity	NPC219011
0.7882	Intermediate Similarity	NPC115786
0.7875	Intermediate Similarity	NPC155587
0.7857	Intermediate Similarity	NPC226988
0.7841	Intermediate Similarity	NPC472872
0.7841	Intermediate Similarity	NPC215556
0.7841	Intermediate Similarity	NPC288699
0.7826	Intermediate Similarity	NPC311904
0.7826	Intermediate Similarity	NPC169205
0.7821	Intermediate Similarity	NPC18543
0.7805	Intermediate Similarity	NPC472960
0.7802	Intermediate Similarity	NPC476053
0.7791	Intermediate Similarity	NPC78089
0.7778	Intermediate Similarity	NPC475700
0.7778	Intermediate Similarity	NPC235906
0.7753	Intermediate Similarity	NPC19087
0.7753	Intermediate Similarity	NPC152467
0.7753	Intermediate Similarity	NPC216284
0.7753	Intermediate Similarity	NPC62815
0.7742	Intermediate Similarity	NPC141191
0.7742	Intermediate Similarity	NPC54843
0.7738	Intermediate Similarity	NPC281949
0.7738	Intermediate Similarity	NPC25684
0.7738	Intermediate Similarity	NPC126248
0.7738	Intermediate Similarity	NPC301477
0.7727	Intermediate Similarity	NPC91248
0.7727	Intermediate Similarity	NPC224652
0.7717	Intermediate Similarity	NPC24956
0.7717	Intermediate Similarity	NPC185553
0.7717	Intermediate Similarity	NPC18019
0.7711	Intermediate Similarity	NPC264227
0.7711	Intermediate Similarity	NPC472965
0.7711	Intermediate Similarity	NPC470239
0.7711	Intermediate Similarity	NPC63649
0.7711	Intermediate Similarity	NPC470244
0.7701	Intermediate Similarity	NPC70555
0.7701	Intermediate Similarity	NPC70422
0.7701	Intermediate Similarity	NPC104961
0.7701	Intermediate Similarity	NPC469676
0.7692	Intermediate Similarity	NPC167219
0.7683	Intermediate Similarity	NPC53581
0.7683	Intermediate Similarity	NPC103987
0.7674	Intermediate Similarity	NPC470011
0.7667	Intermediate Similarity	NPC184063
0.7667	Intermediate Similarity	NPC472953
0.7667	Intermediate Similarity	NPC155215
0.7667	Intermediate Similarity	NPC221282
0.7654	Intermediate Similarity	NPC471491
0.7647	Intermediate Similarity	NPC173609
0.7647	Intermediate Similarity	NPC178676
0.764	Intermediate Similarity	NPC268298
0.764	Intermediate Similarity	NPC4986
0.764	Intermediate Similarity	NPC38392
0.764	Intermediate Similarity	NPC32922
0.7634	Intermediate Similarity	NPC471150
0.7619	Intermediate Similarity	NPC156658
0.7619	Intermediate Similarity	NPC474981
0.7619	Intermediate Similarity	NPC258965
0.7609	Intermediate Similarity	NPC280877
0.759	Intermediate Similarity	NPC299235
0.7582	Intermediate Similarity	NPC258216
0.7561	Intermediate Similarity	NPC472959
0.7558	Intermediate Similarity	NPC128246
0.7558	Intermediate Similarity	NPC272814
0.7556	Intermediate Similarity	NPC129419
0.7556	Intermediate Similarity	NPC37607
0.7556	Intermediate Similarity	NPC301969
0.7529	Intermediate Similarity	NPC255580
0.7529	Intermediate Similarity	NPC39411
0.7528	Intermediate Similarity	NPC53158
0.7528	Intermediate Similarity	NPC215831
0.7527	Intermediate Similarity	NPC126156
0.75	Intermediate Similarity	NPC163003
0.75	Intermediate Similarity	NPC477920
0.75	Intermediate Similarity	NPC284902
0.75	Intermediate Similarity	NPC617
0.75	Intermediate Similarity	NPC85698
0.75	Intermediate Similarity	NPC470243
0.75	Intermediate Similarity	NPC9231
0.7474	Intermediate Similarity	NPC186861
0.7474	Intermediate Similarity	NPC471381
0.7473	Intermediate Similarity	NPC111114
0.7473	Intermediate Similarity	NPC300312
0.7473	Intermediate Similarity	NPC133698
0.7473	Intermediate Similarity	NPC290651
0.7473	Intermediate Similarity	NPC475925
0.7473	Intermediate Similarity	NPC261607
0.7473	Intermediate Similarity	NPC131209
0.7471	Intermediate Similarity	NPC138647

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 NPC290508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	2833
0.2-0.3	3951
0.3-0.4	1450
0.4-0.5	402
0.5-0.6	194
0.6-0.7	31
0.7-0.8	2
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
0.8	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1695	Approved
0.7386	Intermediate Similarity	NPD1694	Approved
0.7191	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5785	Approved
0.6854	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6903	Approved
0.6739	Remote Similarity	NPD5330	Approved
0.6739	Remote Similarity	NPD7521	Approved
0.6739	Remote Similarity	NPD6684	Approved
0.6739	Remote Similarity	NPD7334	Approved
0.6739	Remote Similarity	NPD6409	Approved
0.6739	Remote Similarity	NPD7146	Approved
0.6602	Remote Similarity	NPD6008	Approved
0.6596	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5786	Approved
0.6538	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6399	Phase 3
0.6484	Remote Similarity	NPD5209	Approved
0.6484	Remote Similarity	NPD6435	Approved
0.6458	Remote Similarity	NPD5207	Approved
0.6452	Remote Similarity	NPD5363	Approved
0.6421	Remote Similarity	NPD5737	Approved
0.6421	Remote Similarity	NPD6672	Approved
0.6413	Remote Similarity	NPD5362	Discontinued
0.6404	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5693	Phase 1
0.6374	Remote Similarity	NPD5369	Approved
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6371	Approved
0.6304	Remote Similarity	NPD4269	Approved
0.6304	Remote Similarity	NPD4270	Approved
0.6277	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5368	Approved
0.6263	Remote Similarity	NPD6001	Approved
0.625	Remote Similarity	NPD8039	Approved
0.6224	Remote Similarity	NPD8035	Phase 2
0.6224	Remote Similarity	NPD8034	Phase 2
0.6176	Remote Similarity	NPD4225	Approved
0.6146	Remote Similarity	NPD3573	Approved
0.6129	Remote Similarity	NPD3667	Approved
0.6105	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD9298	Approved
0.61	Remote Similarity	NPD5282	Discontinued
0.6092	Remote Similarity	NPD5777	Approved
0.6091	Remote Similarity	NPD6053	Discontinued
0.6087	Remote Similarity	NPD4252	Approved
0.6082	Remote Similarity	NPD5208	Approved
0.6075	Remote Similarity	NPD5697	Approved
0.6064	Remote Similarity	NPD7154	Phase 3
0.6064	Remote Similarity	NPD4788	Approved
0.6061	Remote Similarity	NPD6411	Approved
0.6061	Remote Similarity	NPD6079	Approved
0.6042	Remote Similarity	NPD3618	Phase 1
0.6042	Remote Similarity	NPD6098	Approved
0.604	Remote Similarity	NPD5695	Phase 3
0.602	Remote Similarity	NPD6904	Approved
0.602	Remote Similarity	NPD6080	Approved
0.602	Remote Similarity	NPD6673	Approved
0.602	Remote Similarity	NPD5328	Approved
0.6019	Remote Similarity	NPD5696	Approved
0.6019	Remote Similarity	NPD7320	Approved
0.6019	Remote Similarity	NPD6011	Approved
0.6019	Remote Similarity	NPD6881	Approved
0.6019	Remote Similarity	NPD7638	Approved
0.6019	Remote Similarity	NPD6899	Approved
0.6018	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD4786	Approved
0.5981	Remote Similarity	NPD6675	Approved
0.5981	Remote Similarity	NPD5739	Approved
0.5981	Remote Similarity	NPD6402	Approved
0.5981	Remote Similarity	NPD7128	Approved
0.5963	Remote Similarity	NPD6373	Approved
0.5963	Remote Similarity	NPD6013	Approved
0.5963	Remote Similarity	NPD6372	Approved
0.5963	Remote Similarity	NPD6014	Approved
0.5963	Remote Similarity	NPD6012	Approved
0.5962	Remote Similarity	NPD7639	Approved
0.5962	Remote Similarity	NPD7640	Approved
0.596	Remote Similarity	NPD5692	Phase 3
0.5952	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7900	Approved
0.5941	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.593	Remote Similarity	NPD229	Approved
0.5926	Remote Similarity	NPD5701	Approved
0.5922	Remote Similarity	NPD6084	Phase 2
0.5922	Remote Similarity	NPD6083	Phase 2
0.5914	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6883	Approved
0.5909	Remote Similarity	NPD7102	Approved
0.5909	Remote Similarity	NPD7290	Approved
0.59	Remote Similarity	NPD5694	Approved
0.59	Remote Similarity	NPD6050	Approved
0.5895	Remote Similarity	NPD5331	Approved
0.5895	Remote Similarity	NPD5332	Approved
0.5876	Remote Similarity	NPD4249	Approved
0.5876	Remote Similarity	NPD5279	Phase 3
0.5859	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6051	Approved
0.5859	Remote Similarity	NPD6101	Approved
0.5856	Remote Similarity	NPD6869	Approved
0.5856	Remote Similarity	NPD8130	Phase 1
0.5856	Remote Similarity	NPD6617	Approved
0.5856	Remote Similarity	NPD6847	Approved
0.5851	Remote Similarity	NPD4790	Discontinued
0.5842	Remote Similarity	NPD5778	Approved
0.5842	Remote Similarity	NPD5779	Approved
0.5825	Remote Similarity	NPD4697	Phase 3
0.5825	Remote Similarity	NPD5222	Approved
0.5825	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5221	Approved
0.5816	Remote Similarity	NPD4250	Approved
0.5816	Remote Similarity	NPD4251	Approved
0.5812	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6882	Approved
0.5804	Remote Similarity	NPD8297	Approved
0.58	Remote Similarity	NPD6698	Approved
0.58	Remote Similarity	NPD46	Approved
0.5794	Remote Similarity	NPD6052	Approved
0.5784	Remote Similarity	NPD7748	Approved
0.5769	Remote Similarity	NPD5173	Approved
0.5769	Remote Similarity	NPD7902	Approved
0.5745	Remote Similarity	NPD4821	Approved
0.5745	Remote Similarity	NPD4822	Approved
0.5745	Remote Similarity	NPD4820	Approved
0.5745	Remote Similarity	NPD4819	Approved
0.5743	Remote Similarity	NPD5284	Approved
0.5743	Remote Similarity	NPD5281	Approved
0.5732	Remote Similarity	NPD3198	Approved
0.5727	Remote Similarity	NPD6686	Approved
0.5726	Remote Similarity	NPD6845	Suspended
0.5714	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3702	Approved
0.5701	Remote Similarity	NPD5211	Phase 2
0.5699	Remote Similarity	NPD4271	Approved
0.5699	Remote Similarity	NPD4268	Approved
0.566	Remote Similarity	NPD5285	Approved
0.566	Remote Similarity	NPD4696	Approved
0.566	Remote Similarity	NPD5286	Approved
0.5652	Remote Similarity	NPD6274	Approved
0.5652	Remote Similarity	NPD6868	Approved
0.5645	Remote Similarity	NPD7260	Phase 2
0.5625	Remote Similarity	NPD4221	Approved
0.5625	Remote Similarity	NPD4223	Phase 3
0.5619	Remote Similarity	NPD4755	Approved
0.5618	Remote Similarity	NPD4691	Approved
0.5614	Remote Similarity	NPD4632	Approved
0.5607	Remote Similarity	NPD5223	Approved
0.5603	Remote Similarity	NPD6317	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