NPASS Compound

Structure

NPC474363 OpenBabel07101718322D 21 21 0 0 1 0 0 0 0 0999 V2000 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 0.8660 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 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 -7.7942 1.5000 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 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.09
Volume:	293.726
LogP:	1.379
LogD:	0.419
LogS:	-2.442
# Rotatable Bonds:	10
TPSA:	86.74
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	2.056
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.695
MDCK Permeability:	5.2903455070918426e-05
Pgp-inhibitor:	0.178
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.299

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.891
Plasma Protein Binding (PPB):	47.36153030395508%
Volume Distribution (VD):	0.294
Pgp-substrate:	54.575286865234375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.129
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.344
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.247
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	7.514
Half-life (T1/2):	0.975

ADMET: Toxicity

hERG Blockers:	0.193
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.668
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.894
Carcinogencity:	0.028
Eye Corrosion:	0.846
Eye Irritation:	0.949
Respiratory Toxicity:	0.72

Download Data

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

Natural Product: NPC474363

Natural Product ID:	NPC474363
*Common Name:**	7-Hydroxy-6-Hydromelodienone
IUPAC Name:	[(E)-2-hydroxy-7-methoxy-4,7-dioxohept-5-enyl] benzoate
Synonyms:
Standard InCHIKey:	DLQZZFILZYWBJV-BQYQJAHWSA-N
Standard InCHI:	InChI=1S/C15H16O6/c1-20-14(18)8-7-12(16)9-13(17)10-21-15(19)11-5-3-2-4-6-11/h2-8,13,17H,9-10H2,1H3/b8-7+
SMILES:	COC(=O)C=CC(=O)CC(COC(=O)C1=CC=CC=C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465634
PubChem CID:	5388652
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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.28	ug ml-1	PMID[456065]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	1.92	ug ml-1	PMID[456065]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.53	10'-1 ug/ml	PMID[456065]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	ED50	=	1.04	ug ml-1	PMID[456065]
NPT375	Cell Line	Malme-3M	Homo sapiens	ED50	=	1.1	ug ml-1	PMID[456065]

☑ 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 NPC474363 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	219
0.1-0.2	846
0.2-0.3	2861
0.3-0.4	7376
0.4-0.5	11252
0.5-0.6	10383
0.6-0.7	8644
0.7-0.8	1007
0.8-0.85	66
0.85-0.9	36
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8909	High Similarity	NPC474314
0.8909	High Similarity	NPC158282
0.8868	High Similarity	NPC474365
0.8868	High Similarity	NPC301943
0.8829	High Similarity	NPC474176
0.8818	High Similarity	NPC476003
0.8667	High Similarity	NPC35448
0.8667	High Similarity	NPC78701
0.8636	High Similarity	NPC474364
0.8585	High Similarity	NPC146351
0.8571	High Similarity	NPC321852
0.8571	High Similarity	NPC92754
0.8571	High Similarity	NPC249912
0.8571	High Similarity	NPC276775
0.8559	High Similarity	NPC174099
0.8532	High Similarity	NPC269457
0.8491	Intermediate Similarity	NPC225060
0.8482	Intermediate Similarity	NPC260818
0.8468	Intermediate Similarity	NPC469636
0.8455	Intermediate Similarity	NPC472315
0.8455	Intermediate Similarity	NPC472316
0.8455	Intermediate Similarity	NPC474376
0.8455	Intermediate Similarity	NPC475203
0.8443	Intermediate Similarity	NPC472707
0.8421	Intermediate Similarity	NPC153053
0.8411	Intermediate Similarity	NPC325497
0.8381	Intermediate Similarity	NPC130398
0.8378	Intermediate Similarity	NPC56493
0.8349	Intermediate Similarity	NPC160382
0.8347	Intermediate Similarity	NPC246166
0.8333	Intermediate Similarity	NPC272524
0.8333	Intermediate Similarity	NPC161611
0.8333	Intermediate Similarity	NPC70624
0.8333	Intermediate Similarity	NPC223351
0.8304	Intermediate Similarity	NPC83628
0.8304	Intermediate Similarity	NPC85493
0.8304	Intermediate Similarity	NPC17417
0.8304	Intermediate Similarity	NPC10251
0.8304	Intermediate Similarity	NPC265407
0.8288	Intermediate Similarity	NPC119271
0.8288	Intermediate Similarity	NPC136962
0.8276	Intermediate Similarity	NPC149691
0.8264	Intermediate Similarity	NPC471466
0.8261	Intermediate Similarity	NPC172525
0.8261	Intermediate Similarity	NPC307651
0.8241	Intermediate Similarity	NPC118343
0.8241	Intermediate Similarity	NPC203925
0.823	Intermediate Similarity	NPC196246
0.823	Intermediate Similarity	NPC251854
0.823	Intermediate Similarity	NPC214067
0.823	Intermediate Similarity	NPC93084
0.8214	Intermediate Similarity	NPC20485
0.8203	Intermediate Similarity	NPC52523
0.8203	Intermediate Similarity	NPC217673
0.819	Intermediate Similarity	NPC474685
0.8165	Intermediate Similarity	NPC42211
0.8158	Intermediate Similarity	NPC474157
0.8158	Intermediate Similarity	NPC1082
0.8158	Intermediate Similarity	NPC305912
0.8151	Intermediate Similarity	NPC90522
0.8151	Intermediate Similarity	NPC328459
0.813	Intermediate Similarity	NPC476033
0.8115	Intermediate Similarity	NPC472704
0.8108	Intermediate Similarity	NPC242913
0.8108	Intermediate Similarity	NPC171831
0.8108	Intermediate Similarity	NPC31786
0.8108	Intermediate Similarity	NPC280616
0.8103	Intermediate Similarity	NPC308744
0.8091	Intermediate Similarity	NPC188895
0.8087	Intermediate Similarity	NPC270699
0.8087	Intermediate Similarity	NPC82899
0.8083	Intermediate Similarity	NPC72977
0.8067	Intermediate Similarity	NPC94637
0.8065	Intermediate Similarity	NPC472706
0.8065	Intermediate Similarity	NPC114096
0.8053	Intermediate Similarity	NPC277788
0.8033	Intermediate Similarity	NPC475692
0.8033	Intermediate Similarity	NPC474283
0.8033	Intermediate Similarity	NPC472703
0.8018	Intermediate Similarity	NPC91820
0.8018	Intermediate Similarity	NPC82426
0.8018	Intermediate Similarity	NPC89886
0.8017	Intermediate Similarity	NPC128368
0.8	Intermediate Similarity	NPC210089
0.8	Intermediate Similarity	NPC148026
0.7984	Intermediate Similarity	NPC79608
0.7983	Intermediate Similarity	NPC469574
0.7982	Intermediate Similarity	NPC210529
0.7982	Intermediate Similarity	NPC175852
0.7982	Intermediate Similarity	NPC160548
0.7967	Intermediate Similarity	NPC475691
0.7967	Intermediate Similarity	NPC138798
0.7965	Intermediate Similarity	NPC37622
0.7965	Intermediate Similarity	NPC30594
0.7965	Intermediate Similarity	NPC37115
0.7949	Intermediate Similarity	NPC87069
0.7949	Intermediate Similarity	NPC237366
0.7937	Intermediate Similarity	NPC301857
0.7928	Intermediate Similarity	NPC25458
0.792	Intermediate Similarity	NPC169913
0.7905	Intermediate Similarity	NPC173443
0.7899	Intermediate Similarity	NPC128825
0.7891	Intermediate Similarity	NPC233692
0.7891	Intermediate Similarity	NPC239358
0.789	Intermediate Similarity	NPC253423
0.7881	Intermediate Similarity	NPC210092
0.7881	Intermediate Similarity	NPC306740
0.7881	Intermediate Similarity	NPC469509
0.7881	Intermediate Similarity	NPC81808
0.7876	Intermediate Similarity	NPC209632
0.7876	Intermediate Similarity	NPC472919
0.7874	Intermediate Similarity	NPC27712
0.7863	Intermediate Similarity	NPC265002
0.7846	Intermediate Similarity	NPC477896
0.7846	Intermediate Similarity	NPC472247
0.784	Intermediate Similarity	NPC275576
0.784	Intermediate Similarity	NPC236405
0.783	Intermediate Similarity	NPC62765
0.7829	Intermediate Similarity	NPC472248
0.7826	Intermediate Similarity	NPC469511
0.7826	Intermediate Similarity	NPC281604
0.7823	Intermediate Similarity	NPC228739
0.7818	Intermediate Similarity	NPC229242
0.7815	Intermediate Similarity	NPC471616
0.7815	Intermediate Similarity	NPC210531
0.7798	Intermediate Similarity	NPC61944
0.7788	Intermediate Similarity	NPC19136
0.7788	Intermediate Similarity	NPC249067
0.7788	Intermediate Similarity	NPC114594
0.7787	Intermediate Similarity	NPC473243
0.7787	Intermediate Similarity	NPC233282
0.7778	Intermediate Similarity	NPC234376
0.7778	Intermediate Similarity	NPC185840
0.7778	Intermediate Similarity	NPC110211
0.7769	Intermediate Similarity	NPC289572
0.7769	Intermediate Similarity	NPC295406
0.7769	Intermediate Similarity	NPC28836
0.7769	Intermediate Similarity	NPC114116
0.7769	Intermediate Similarity	NPC200422
0.7769	Intermediate Similarity	NPC38420
0.7769	Intermediate Similarity	NPC94298
0.7769	Intermediate Similarity	NPC136608
0.7769	Intermediate Similarity	NPC157478
0.7769	Intermediate Similarity	NPC311492
0.7769	Intermediate Similarity	NPC27633
0.7768	Intermediate Similarity	NPC45613
0.776	Intermediate Similarity	NPC295664
0.7752	Intermediate Similarity	NPC233860
0.7748	Intermediate Similarity	NPC217621
0.7739	Intermediate Similarity	NPC156648
0.7739	Intermediate Similarity	NPC211439
0.7736	Intermediate Similarity	NPC220893
0.7734	Intermediate Similarity	NPC272946
0.7734	Intermediate Similarity	NPC262819
0.7721	Intermediate Similarity	NPC134131
0.7721	Intermediate Similarity	NPC25043
0.7714	Intermediate Similarity	NPC89377
0.771	Intermediate Similarity	NPC200154
0.771	Intermediate Similarity	NPC477893
0.771	Intermediate Similarity	NPC474097
0.7705	Intermediate Similarity	NPC204784
0.7705	Intermediate Similarity	NPC472708
0.7704	Intermediate Similarity	NPC45307
0.7699	Intermediate Similarity	NPC234305
0.7699	Intermediate Similarity	NPC60679
0.7698	Intermediate Similarity	NPC4164
0.7692	Intermediate Similarity	NPC477364
0.7692	Intermediate Similarity	NPC302844
0.7687	Intermediate Similarity	NPC473497
0.7687	Intermediate Similarity	NPC474303
0.7687	Intermediate Similarity	NPC242355
0.7687	Intermediate Similarity	NPC77493
0.7687	Intermediate Similarity	NPC475413
0.7686	Intermediate Similarity	NPC240664
0.7686	Intermediate Similarity	NPC217423
0.7679	Intermediate Similarity	NPC282895
0.7672	Intermediate Similarity	NPC269023
0.7672	Intermediate Similarity	NPC40178
0.7672	Intermediate Similarity	NPC99846
0.7664	Intermediate Similarity	NPC477737
0.7652	Intermediate Similarity	NPC176102
0.7652	Intermediate Similarity	NPC254832
0.7652	Intermediate Similarity	NPC71108
0.7652	Intermediate Similarity	NPC204257
0.7652	Intermediate Similarity	NPC29317
0.7652	Intermediate Similarity	NPC229638
0.7652	Intermediate Similarity	NPC267539
0.7647	Intermediate Similarity	NPC477411
0.7642	Intermediate Similarity	NPC304760
0.7638	Intermediate Similarity	NPC204579
0.7634	Intermediate Similarity	NPC203486
0.7634	Intermediate Similarity	NPC477368
0.7634	Intermediate Similarity	NPC136994
0.7634	Intermediate Similarity	NPC43627
0.7634	Intermediate Similarity	NPC88255
0.7632	Intermediate Similarity	NPC85977
0.763	Intermediate Similarity	NPC182869
0.7619	Intermediate Similarity	NPC318107
0.7619	Intermediate Similarity	NPC57607
0.7619	Intermediate Similarity	NPC125053

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 NPC474363 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	659
0.2-0.3	1524
0.3-0.4	2736
0.4-0.5	2312
0.5-0.6	1219
0.6-0.7	442
0.7-0.8	62
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8319	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD2182	Approved
0.8241	Intermediate Similarity	NPD1238	Approved
0.8108	Intermediate Similarity	NPD164	Approved
0.8034	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD9495	Approved
0.7899	Intermediate Similarity	NPD9493	Approved
0.783	Intermediate Similarity	NPD9256	Approved
0.783	Intermediate Similarity	NPD9258	Approved
0.7788	Intermediate Similarity	NPD1237	Approved
0.7769	Intermediate Similarity	NPD9545	Approved
0.7759	Intermediate Similarity	NPD2067	Discontinued
0.7731	Intermediate Similarity	NPD2629	Approved
0.7699	Intermediate Similarity	NPD6647	Phase 2
0.7619	Intermediate Similarity	NPD9257	Approved
0.7619	Intermediate Similarity	NPD9259	Approved
0.7615	Intermediate Similarity	NPD1202	Approved
0.76	Intermediate Similarity	NPD9717	Approved
0.7597	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5647	Approved
0.7479	Intermediate Similarity	NPD969	Suspended
0.7381	Intermediate Similarity	NPD6287	Discontinued
0.7368	Intermediate Similarity	NPD447	Suspended
0.7364	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6085	Phase 2
0.7333	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD4628	Phase 3
0.7317	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD9263	Approved
0.7288	Intermediate Similarity	NPD9264	Approved
0.7288	Intermediate Similarity	NPD9267	Approved
0.7288	Intermediate Similarity	NPD1358	Approved
0.7287	Intermediate Similarity	NPD1203	Approved
0.7281	Intermediate Similarity	NPD2066	Phase 3
0.7273	Intermediate Similarity	NPD2313	Discontinued
0.7252	Intermediate Similarity	NPD6832	Phase 2
0.725	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1929	Approved
0.7241	Intermediate Similarity	NPD1930	Approved
0.7239	Intermediate Similarity	NPD230	Phase 1
0.7236	Intermediate Similarity	NPD4198	Discontinued
0.7231	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1019	Discontinued
0.7227	Intermediate Similarity	NPD74	Approved
0.7227	Intermediate Similarity	NPD9266	Approved
0.7209	Intermediate Similarity	NPD2198	Approved
0.7209	Intermediate Similarity	NPD2199	Approved
0.7206	Intermediate Similarity	NPD2799	Discontinued
0.7197	Intermediate Similarity	NPD7008	Discontinued
0.717	Intermediate Similarity	NPD9491	Approved
0.7164	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5403	Approved
0.7131	Intermediate Similarity	NPD5277	Phase 2
0.7119	Intermediate Similarity	NPD5048	Discontinued
0.7113	Intermediate Similarity	NPD5401	Approved
0.7109	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD9261	Approved
0.7091	Intermediate Similarity	NPD800	Approved
0.7087	Intermediate Similarity	NPD5305	Approved
0.7087	Intermediate Similarity	NPD5306	Approved
0.708	Intermediate Similarity	NPD1693	Approved
0.708	Intermediate Similarity	NPD9260	Approved
0.7073	Intermediate Similarity	NPD1241	Discontinued
0.7071	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD9494	Approved
0.7034	Intermediate Similarity	NPD5909	Discontinued
0.7031	Intermediate Similarity	NPD4136	Approved
0.7031	Intermediate Similarity	NPD4106	Approved
0.7031	Intermediate Similarity	NPD4135	Approved
0.7027	Intermediate Similarity	NPD1089	Approved
0.7027	Intermediate Similarity	NPD1086	Approved
0.7027	Intermediate Similarity	NPD1090	Approved
0.7025	Intermediate Similarity	NPD1317	Discontinued
0.7023	Intermediate Similarity	NPD2628	Approved
0.7023	Intermediate Similarity	NPD2160	Approved
0.7023	Intermediate Similarity	NPD2627	Approved
0.7023	Intermediate Similarity	NPD2159	Approved
0.7023	Intermediate Similarity	NPD2625	Approved
0.7023	Intermediate Similarity	NPD2626	Approved
0.7016	Intermediate Similarity	NPD9281	Approved
0.7016	Intermediate Similarity	NPD5951	Approved
0.7015	Intermediate Similarity	NPD411	Approved
0.7015	Intermediate Similarity	NPD6798	Discontinued
0.7009	Intermediate Similarity	NPD1932	Approved
0.7007	Intermediate Similarity	NPD2567	Approved
0.7007	Intermediate Similarity	NPD2569	Approved
0.7	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1933	Approved
0.6978	Remote Similarity	NPD2346	Discontinued
0.6977	Remote Similarity	NPD4807	Approved
0.6977	Remote Similarity	NPD4806	Approved
0.6972	Remote Similarity	NPD7236	Approved
0.697	Remote Similarity	NPD2798	Approved
0.6963	Remote Similarity	NPD6233	Phase 2
0.6963	Remote Similarity	NPD4062	Phase 3
0.6959	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6010	Discontinued
0.6917	Remote Similarity	NPD3134	Approved
0.6913	Remote Similarity	NPD5402	Approved
0.6911	Remote Similarity	NPD9508	Approved
0.6909	Remote Similarity	NPD1282	Approved
0.6906	Remote Similarity	NPD2935	Discontinued
0.6906	Remote Similarity	NPD1551	Phase 2
0.6903	Remote Similarity	NPD1088	Approved
0.6892	Remote Similarity	NPD6801	Discontinued
0.6889	Remote Similarity	NPD3764	Approved
0.6879	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4105	Approved
0.6875	Remote Similarity	NPD4102	Approved
0.6875	Remote Similarity	NPD4662	Approved
0.6875	Remote Similarity	NPD4661	Approved
0.6871	Remote Similarity	NPD6599	Discontinued
0.687	Remote Similarity	NPD5157	Phase 1
0.687	Remote Similarity	NPD1989	Approved
0.687	Remote Similarity	NPD5159	Phase 2
0.687	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6355	Discontinued
0.686	Remote Similarity	NPD290	Approved
0.6857	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7798	Approved
0.6838	Remote Similarity	NPD520	Approved
0.6822	Remote Similarity	NPD1104	Approved
0.6822	Remote Similarity	NPD226	Approved
0.6821	Remote Similarity	NPD7075	Discontinued
0.6818	Remote Similarity	NPD5667	Approved
0.6807	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3455	Phase 2
0.6803	Remote Similarity	NPD2329	Discontinued
0.68	Remote Similarity	NPD2650	Approved
0.68	Remote Similarity	NPD2652	Approved
0.6797	Remote Similarity	NPD1894	Discontinued
0.6792	Remote Similarity	NPD9490	Approved
0.6791	Remote Similarity	NPD5204	Approved
0.6791	Remote Similarity	NPD3661	Approved
0.6791	Remote Similarity	NPD3664	Approved
0.6791	Remote Similarity	NPD3663	Approved
0.6791	Remote Similarity	NPD3662	Phase 3
0.6786	Remote Similarity	NPD689	Discontinued
0.6783	Remote Similarity	NPD3887	Approved
0.6783	Remote Similarity	NPD2354	Approved
0.6783	Remote Similarity	NPD6190	Approved
0.6772	Remote Similarity	NPD5291	Approved
0.6772	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5292	Approved
0.6767	Remote Similarity	NPD552	Approved
0.6767	Remote Similarity	NPD553	Approved
0.6767	Remote Similarity	NPD9567	Approved
0.6757	Remote Similarity	NPD1087	Approved
0.6757	Remote Similarity	NPD4380	Phase 2
0.6741	Remote Similarity	NPD4617	Approved
0.6741	Remote Similarity	NPD5203	Approved
0.6741	Remote Similarity	NPD4620	Approved
0.6741	Remote Similarity	NPD5201	Approved
0.6735	Remote Similarity	NPD7239	Suspended
0.6726	Remote Similarity	NPD3673	Approved
0.6726	Remote Similarity	NPD3672	Approved
0.6712	Remote Similarity	NPD5049	Phase 3
0.6692	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1778	Approved
0.6691	Remote Similarity	NPD6039	Approved
0.6691	Remote Similarity	NPD6653	Approved
0.669	Remote Similarity	NPD1549	Phase 2
0.6689	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2240	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD1239	Approved
0.6667	Remote Similarity	NPD2239	Approved
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD2684	Approved
0.6644	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2797	Approved
0.6642	Remote Similarity	NPD3268	Approved
0.6639	Remote Similarity	NPD6685	Approved
0.6637	Remote Similarity	NPD5346	Phase 2
0.6637	Remote Similarity	NPD5347	Phase 2
0.662	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD1246	Approved
0.6607	Remote Similarity	NPD4793	Discontinued
0.6604	Remote Similarity	NPD9294	Approved
0.6601	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7411	Suspended
0.6599	Remote Similarity	NPD6273	Approved
0.6597	Remote Similarity	NPD2575	Approved
0.6597	Remote Similarity	NPD8166	Discontinued
0.6596	Remote Similarity	NPD7033	Discontinued
0.6596	Remote Similarity	NPD1510	Phase 2
0.6596	Remote Similarity	NPD4308	Phase 3

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