NPASS Compound

Structure

NPC301943 OpenBabel07101718312D 21 21 0 0 0 0 0 0 0 0999 V2000 -6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 11 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	299.595
LogP:	2.738
LogD:	2.844
LogS:	-4.279
# Rotatable Bonds:	9
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.567
Synthetic Accessibility Score:	2.319
Fsp3:	0.188
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:	-4.484
MDCK Permeability:	2.744258745224215e-05
Pgp-inhibitor:	0.077
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.429
Plasma Protein Binding (PPB):	93.07617950439453%
Volume Distribution (VD):	0.742
Pgp-substrate:	2.557710886001587%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.881
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.867
CYP2D6-inhibitor:	0.585
CYP2D6-substrate:	0.178
CYP3A4-inhibitor:	0.18
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	10.26
Half-life (T1/2):	0.909

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.265
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.208
Skin Sensitization:	0.969
Carcinogencity:	0.558
Eye Corrosion:	0.513
Eye Irritation:	0.986
Respiratory Toxicity:	0.525

Download Data

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

Natural Product: NPC301943

Natural Product ID:	NPC301943
*Common Name:**	Homomelodienone
IUPAC Name:	[(2E,5E)-7-ethoxy-4,7-dioxohepta-2,5-dienyl] benzoate
Synonyms:	Homomelodienone
Standard InCHIKey:	FCTFULMZKQYRQV-GOKBKIRCSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-2-20-15(18)11-10-14(17)9-6-12-21-16(19)13-7-4-3-5-8-13/h3-11H,2,12H2,1H3/b9-6+,11-10+
SMILES:	CCOC(=O)/C=C/C(=O)/C=C/COC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465646
PubChem CID:	6439393
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic 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
NPO6499	Melodorum fruticosum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1919592]
NPO6499	Melodorum fruticosum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	36.91	ug ml-1	PMID[554318]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	25.61	ug ml-1	PMID[554318]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	37.88	ug ml-1	PMID[554318]

☑ 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 NPC301943 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	225
0.1-0.2	1186
0.2-0.3	3637
0.3-0.4	8945
0.4-0.5	11029
0.5-0.6	11403
0.6-0.7	5408
0.7-0.8	736
0.8-0.85	59
0.85-0.9	44
0.9-0.95	18
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474365
0.9579	High Similarity	NPC35448
0.9579	High Similarity	NPC78701
0.9479	High Similarity	NPC325497
0.9479	High Similarity	NPC146351
0.9474	High Similarity	NPC249912
0.9474	High Similarity	NPC276775
0.9474	High Similarity	NPC92754
0.9375	High Similarity	NPC225060
0.9307	High Similarity	NPC469636
0.9263	High Similarity	NPC130398
0.92	High Similarity	NPC269457
0.9184	High Similarity	NPC70624
0.9118	High Similarity	NPC474364
0.9118	High Similarity	NPC10251
0.9118	High Similarity	NPC17417
0.9082	High Similarity	NPC203925
0.9082	High Similarity	NPC118343
0.9029	High Similarity	NPC93084
0.9029	High Similarity	NPC196246
0.9029	High Similarity	NPC214067
0.9029	High Similarity	NPC251854
0.902	High Similarity	NPC56493
0.899	High Similarity	NPC42211
0.8952	High Similarity	NPC161611
0.8942	High Similarity	NPC1082
0.8942	High Similarity	NPC305912
0.8942	High Similarity	NPC476003
0.8922	High Similarity	NPC119271
0.89	High Similarity	NPC188895
0.8868	High Similarity	NPC474363
0.8868	High Similarity	NPC307651
0.8857	High Similarity	NPC82899
0.8857	High Similarity	NPC270699
0.8846	High Similarity	NPC174099
0.8785	High Similarity	NPC210092
0.8774	High Similarity	NPC128368
0.8762	High Similarity	NPC210089
0.8762	High Similarity	NPC474157
0.875	High Similarity	NPC265407
0.875	High Similarity	NPC83628
0.8737	High Similarity	NPC173443
0.8725	High Similarity	NPC31786
0.8692	High Similarity	NPC153053
0.8679	High Similarity	NPC321852
0.8641	High Similarity	NPC209632
0.8627	High Similarity	NPC89886
0.8598	High Similarity	NPC474176
0.8585	High Similarity	NPC260818
0.8558	High Similarity	NPC30594
0.8558	High Similarity	NPC37622
0.8544	High Similarity	NPC114594
0.8542	High Similarity	NPC220893
0.8526	High Similarity	NPC89377
0.8505	High Similarity	NPC474314
0.8482	Intermediate Similarity	NPC473243
0.8447	Intermediate Similarity	NPC60679
0.8426	Intermediate Similarity	NPC272524
0.8421	Intermediate Similarity	NPC318107
0.8396	Intermediate Similarity	NPC99846
0.8396	Intermediate Similarity	NPC269023
0.8396	Intermediate Similarity	NPC85493
0.8384	Intermediate Similarity	NPC261181
0.8378	Intermediate Similarity	NPC469574
0.8367	Intermediate Similarity	NPC119631
0.8364	Intermediate Similarity	NPC149691
0.835	Intermediate Similarity	NPC45613
0.8349	Intermediate Similarity	NPC308744
0.8333	Intermediate Similarity	NPC158282
0.8317	Intermediate Similarity	NPC270654
0.8316	Intermediate Similarity	NPC58616
0.8283	Intermediate Similarity	NPC77273
0.8273	Intermediate Similarity	NPC474685
0.8247	Intermediate Similarity	NPC304760
0.8246	Intermediate Similarity	NPC50872
0.8241	Intermediate Similarity	NPC167504
0.819	Intermediate Similarity	NPC472704
0.8173	Intermediate Similarity	NPC25458
0.8165	Intermediate Similarity	NPC79496
0.8137	Intermediate Similarity	NPC253423
0.8125	Intermediate Similarity	NPC294134
0.812	Intermediate Similarity	NPC295664
0.8108	Intermediate Similarity	NPC474095
0.8103	Intermediate Similarity	NPC472703
0.8081	Intermediate Similarity	NPC213156
0.8081	Intermediate Similarity	NPC62765
0.8081	Intermediate Similarity	NPC240108
0.807	Intermediate Similarity	NPC90522
0.807	Intermediate Similarity	NPC204784
0.807	Intermediate Similarity	NPC328459
0.8058	Intermediate Similarity	NPC229242
0.8056	Intermediate Similarity	NPC40178
0.8053	Intermediate Similarity	NPC45104
0.8053	Intermediate Similarity	NPC217423
0.8051	Intermediate Similarity	NPC476599
0.8039	Intermediate Similarity	NPC61944
0.8036	Intermediate Similarity	NPC100353
0.8018	Intermediate Similarity	NPC196075
0.8018	Intermediate Similarity	NPC477411
0.8	Intermediate Similarity	NPC72977
0.7982	Intermediate Similarity	NPC293424
0.7982	Intermediate Similarity	NPC94298
0.7982	Intermediate Similarity	NPC27633
0.7982	Intermediate Similarity	NPC94637
0.7981	Intermediate Similarity	NPC217621
0.798	Intermediate Similarity	NPC9822
0.7966	Intermediate Similarity	NPC125053
0.7966	Intermediate Similarity	NPC246166
0.7963	Intermediate Similarity	NPC20485
0.7963	Intermediate Similarity	NPC470391
0.7963	Intermediate Similarity	NPC47536
0.7949	Intermediate Similarity	NPC223351
0.7946	Intermediate Similarity	NPC306740
0.7946	Intermediate Similarity	NPC81808
0.7946	Intermediate Similarity	NPC228936
0.7941	Intermediate Similarity	NPC5472
0.7925	Intermediate Similarity	NPC234305
0.7917	Intermediate Similarity	NPC288903
0.7909	Intermediate Similarity	NPC243355
0.7899	Intermediate Similarity	NPC275576
0.789	Intermediate Similarity	NPC281604
0.7876	Intermediate Similarity	NPC226093
0.7876	Intermediate Similarity	NPC188907
0.7876	Intermediate Similarity	NPC220540
0.787	Intermediate Similarity	NPC474376
0.787	Intermediate Similarity	NPC475203
0.787	Intermediate Similarity	NPC472316
0.787	Intermediate Similarity	NPC472315
0.7863	Intermediate Similarity	NPC26285
0.7857	Intermediate Similarity	NPC237366
0.785	Intermediate Similarity	NPC269644
0.785	Intermediate Similarity	NPC85977
0.7845	Intermediate Similarity	NPC230951
0.7838	Intermediate Similarity	NPC212415
0.7838	Intermediate Similarity	NPC23332
0.7833	Intermediate Similarity	NPC110211
0.7833	Intermediate Similarity	NPC204579
0.7833	Intermediate Similarity	NPC472706
0.7833	Intermediate Similarity	NPC169913
0.783	Intermediate Similarity	NPC284477
0.783	Intermediate Similarity	NPC304873
0.7822	Intermediate Similarity	NPC110704
0.7815	Intermediate Similarity	NPC221798
0.7812	Intermediate Similarity	NPC323103
0.781	Intermediate Similarity	NPC228435
0.781	Intermediate Similarity	NPC472318
0.781	Intermediate Similarity	NPC98911
0.7807	Intermediate Similarity	NPC190298
0.7807	Intermediate Similarity	NPC470860
0.7807	Intermediate Similarity	NPC128825
0.7807	Intermediate Similarity	NPC131192
0.7797	Intermediate Similarity	NPC474283
0.7797	Intermediate Similarity	NPC475692
0.7788	Intermediate Similarity	NPC474408
0.7787	Intermediate Similarity	NPC272946
0.7787	Intermediate Similarity	NPC473247
0.7787	Intermediate Similarity	NPC42234
0.7769	Intermediate Similarity	NPC472707
0.7768	Intermediate Similarity	NPC13784
0.7757	Intermediate Similarity	NPC160382
0.775	Intermediate Similarity	NPC49938
0.775	Intermediate Similarity	NPC470765
0.7748	Intermediate Similarity	NPC183648
0.7739	Intermediate Similarity	NPC240664
0.7739	Intermediate Similarity	NPC469954
0.7736	Intermediate Similarity	NPC282895
0.7736	Intermediate Similarity	NPC473325
0.7732	Intermediate Similarity	NPC270507
0.7731	Intermediate Similarity	NPC471466
0.7731	Intermediate Similarity	NPC228739
0.7731	Intermediate Similarity	NPC475691
0.7727	Intermediate Similarity	NPC469511
0.7724	Intermediate Similarity	NPC282230
0.7724	Intermediate Similarity	NPC469519
0.7724	Intermediate Similarity	NPC183348
0.7719	Intermediate Similarity	NPC135730
0.7719	Intermediate Similarity	NPC471616
0.7714	Intermediate Similarity	NPC179411
0.7708	Intermediate Similarity	NPC89950
0.7708	Intermediate Similarity	NPC303245
0.7706	Intermediate Similarity	NPC326447
0.7706	Intermediate Similarity	NPC1065
0.7706	Intermediate Similarity	NPC136962
0.7706	Intermediate Similarity	NPC51174
0.7705	Intermediate Similarity	NPC2596
0.7699	Intermediate Similarity	NPC53953
0.7692	Intermediate Similarity	NPC233282
0.7686	Intermediate Similarity	NPC114096
0.7686	Intermediate Similarity	NPC473220
0.7686	Intermediate Similarity	NPC470753
0.7685	Intermediate Similarity	NPC249067
0.7684	Intermediate Similarity	NPC167577
0.7684	Intermediate Similarity	NPC78517
0.7679	Intermediate Similarity	NPC54626
0.7679	Intermediate Similarity	NPC57879
0.767	Intermediate Similarity	NPC23453
0.7667	Intermediate Similarity	NPC184219
0.7661	Intermediate Similarity	NPC477360
0.7661	Intermediate Similarity	NPC470977
0.7661	Intermediate Similarity	NPC15083

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 NPC301943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	862
0.2-0.3	1308
0.3-0.4	2741
0.4-0.5	2378
0.5-0.6	1186
0.6-0.7	397
0.7-0.8	75
0.8-0.85	6
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9118	High Similarity	NPD2182	Approved
0.9082	High Similarity	NPD1238	Approved
0.8942	High Similarity	NPD2181	Clinical (unspecified phase)
0.8725	High Similarity	NPD164	Approved
0.8421	Intermediate Similarity	NPD9259	Approved
0.8421	Intermediate Similarity	NPD9257	Approved
0.8384	Intermediate Similarity	NPD1202	Approved
0.8174	Intermediate Similarity	NPD6287	Discontinued
0.8081	Intermediate Similarity	NPD9256	Approved
0.8081	Intermediate Similarity	NPD9258	Approved
0.7982	Intermediate Similarity	NPD9545	Approved
0.7982	Intermediate Similarity	NPD2067	Discontinued
0.7946	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2198	Approved
0.7815	Intermediate Similarity	NPD2199	Approved
0.7807	Intermediate Similarity	NPD9493	Approved
0.7767	Intermediate Similarity	NPD9260	Approved
0.7757	Intermediate Similarity	NPD6647	Phase 2
0.7706	Intermediate Similarity	NPD3134	Approved
0.7705	Intermediate Similarity	NPD6832	Phase 2
0.7699	Intermediate Similarity	NPD1241	Discontinued
0.7692	Intermediate Similarity	NPD1989	Approved
0.7685	Intermediate Similarity	NPD1237	Approved
0.7642	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD2066	Phase 3
0.7636	Intermediate Similarity	NPD1358	Approved
0.7593	Intermediate Similarity	NPD1929	Approved
0.7593	Intermediate Similarity	NPD1930	Approved
0.7593	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD3672	Approved
0.7549	Intermediate Similarity	NPD3673	Approved
0.7547	Intermediate Similarity	NPD9495	Approved
0.7542	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD1019	Discontinued
0.7523	Intermediate Similarity	NPD5909	Discontinued
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD9490	Approved
0.75	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5277	Phase 2
0.7431	Intermediate Similarity	NPD9261	Approved
0.7426	Intermediate Similarity	NPD1087	Approved
0.7426	Intermediate Similarity	NPD1282	Approved
0.7374	Intermediate Similarity	NPD9491	Approved
0.736	Intermediate Similarity	NPD7008	Discontinued
0.7355	Intermediate Similarity	NPD3972	Approved
0.7328	Intermediate Similarity	NPD5951	Approved
0.7328	Intermediate Similarity	NPD2629	Approved
0.7317	Intermediate Similarity	NPD9567	Approved
0.7317	Intermediate Similarity	NPD552	Approved
0.7317	Intermediate Similarity	NPD553	Approved
0.7288	Intermediate Similarity	NPD2347	Approved
0.7287	Intermediate Similarity	NPD2569	Approved
0.7287	Intermediate Similarity	NPD2567	Approved
0.7282	Intermediate Similarity	NPD800	Approved
0.7273	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD1693	Approved
0.7258	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6039	Approved
0.7222	Intermediate Similarity	NPD5926	Approved
0.7216	Intermediate Similarity	NPD227	Approved
0.7216	Intermediate Similarity	NPD225	Approved
0.7212	Intermediate Similarity	NPD1086	Approved
0.7212	Intermediate Similarity	NPD1089	Approved
0.7212	Intermediate Similarity	NPD1090	Approved
0.7188	Intermediate Similarity	NPD3373	Approved
0.7182	Intermediate Similarity	NPD1932	Approved
0.7177	Intermediate Similarity	NPD1203	Approved
0.7168	Intermediate Similarity	NPD9267	Approved
0.7168	Intermediate Similarity	NPD9264	Approved
0.7168	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD9263	Approved
0.7165	Intermediate Similarity	NPD2313	Discontinued
0.7156	Intermediate Similarity	NPD7798	Approved
0.7143	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1933	Approved
0.712	Intermediate Similarity	NPD2798	Approved
0.7119	Intermediate Similarity	NPD4198	Discontinued
0.7109	Intermediate Similarity	NPD7713	Phase 3
0.7105	Intermediate Similarity	NPD9266	Approved
0.7105	Intermediate Similarity	NPD74	Approved
0.7099	Intermediate Similarity	NPD2799	Discontinued
0.7097	Intermediate Similarity	NPD1876	Approved
0.7097	Intermediate Similarity	NPD5667	Approved
0.7083	Intermediate Similarity	NPD1894	Discontinued
0.7077	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1088	Approved
0.7069	Intermediate Similarity	NPD9508	Approved
0.7069	Intermediate Similarity	NPD969	Suspended
0.7054	Intermediate Similarity	NPD3142	Approved
0.7054	Intermediate Similarity	NPD3140	Approved
0.7054	Intermediate Similarity	NPD4307	Phase 2
0.7049	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5237	Approved
0.7043	Intermediate Similarity	NPD5236	Approved
0.7043	Intermediate Similarity	NPD5239	Approved
0.7043	Intermediate Similarity	NPD5240	Approved
0.7043	Intermediate Similarity	NPD5235	Approved
0.7043	Intermediate Similarity	NPD1317	Discontinued
0.704	Intermediate Similarity	NPD3266	Approved
0.704	Intermediate Similarity	NPD3267	Approved
0.7037	Intermediate Similarity	NPD3887	Approved
0.7031	Intermediate Similarity	NPD3764	Approved
0.7025	Intermediate Similarity	NPD5585	Approved
0.7023	Intermediate Similarity	NPD2670	Approved
0.7	Intermediate Similarity	NPD226	Approved
0.7	Intermediate Similarity	NPD942	Approved
0.7	Intermediate Similarity	NPD230	Phase 1
0.6992	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD9697	Approved
0.6985	Remote Similarity	NPD7236	Approved
0.6984	Remote Similarity	NPD6085	Phase 2
0.6984	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD2201	Approved
0.6983	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7609	Phase 3
0.697	Remote Similarity	NPD3170	Approved
0.6967	Remote Similarity	NPD1104	Approved
0.6967	Remote Similarity	NPD5306	Approved
0.6967	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5305	Approved
0.6963	Remote Similarity	NPD4628	Phase 3
0.6957	Remote Similarity	NPD2329	Discontinued
0.6952	Remote Similarity	NPD5347	Phase 2
0.6952	Remote Similarity	NPD5346	Phase 2
0.6947	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6637	Approved
0.6934	Remote Similarity	NPD6799	Approved
0.6923	Remote Similarity	NPD650	Approved
0.6923	Remote Similarity	NPD4793	Discontinued
0.6917	Remote Similarity	NPD2935	Discontinued
0.6916	Remote Similarity	NPD7631	Approved
0.6911	Remote Similarity	NPD4136	Approved
0.6911	Remote Similarity	NPD3496	Discontinued
0.6911	Remote Similarity	NPD4135	Approved
0.6911	Remote Similarity	NPD4106	Approved
0.6905	Remote Similarity	NPD2797	Approved
0.6899	Remote Similarity	NPD411	Approved
0.6899	Remote Similarity	NPD3268	Approved
0.6897	Remote Similarity	NPD4233	Approved
0.6897	Remote Similarity	NPD4234	Approved
0.6891	Remote Similarity	NPD9281	Approved
0.6885	Remote Similarity	NPD5691	Approved
0.688	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5157	Phase 1
0.688	Remote Similarity	NPD5159	Phase 2
0.687	Remote Similarity	NPD447	Suspended
0.6866	Remote Similarity	NPD7611	Approved
0.6866	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2346	Discontinued
0.6866	Remote Similarity	NPD2353	Approved
0.6864	Remote Similarity	NPD6858	Approved
0.6864	Remote Similarity	NPD5535	Approved
0.6864	Remote Similarity	NPD7094	Approved
0.686	Remote Similarity	NPD5536	Phase 2
0.6855	Remote Similarity	NPD4806	Approved
0.6855	Remote Similarity	NPD4807	Approved
0.6852	Remote Similarity	NPD1563	Approved
0.685	Remote Similarity	NPD2788	Approved
0.6842	Remote Similarity	NPD4308	Phase 3
0.6842	Remote Similarity	NPD3748	Approved
0.6842	Remote Similarity	NPD1109	Approved
0.6842	Remote Similarity	NPD5048	Discontinued
0.6842	Remote Similarity	NPD1110	Approved
0.6838	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1778	Approved
0.6829	Remote Similarity	NPD17	Approved
0.6822	Remote Similarity	NPD1239	Approved
0.6814	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2650	Approved
0.6807	Remote Similarity	NPD2652	Approved
0.6794	Remote Similarity	NPD2979	Phase 3
0.6792	Remote Similarity	NPD689	Discontinued
0.6791	Remote Similarity	NPD1551	Phase 2
0.6791	Remote Similarity	NPD2796	Approved
0.6786	Remote Similarity	NPD2550	Approved
0.6786	Remote Similarity	NPD2553	Approved
0.6786	Remote Similarity	NPD2549	Approved
0.6786	Remote Similarity	NPD2552	Approved
0.6786	Remote Similarity	NPD2555	Approved
0.6786	Remote Similarity	NPD2558	Approved
0.6777	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5291	Approved
0.6777	Remote Similarity	NPD5292	Approved
0.6774	Remote Similarity	NPD3847	Discontinued
0.6774	Remote Similarity	NPD1889	Phase 1
0.6769	Remote Similarity	NPD6798	Discontinued
0.6769	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1756	Approved
0.6752	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1752	Approved
0.675	Remote Similarity	NPD1246	Approved
0.6748	Remote Similarity	NPD4105	Approved
0.6748	Remote Similarity	NPD4102	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