NPASS Compound

Structure

NPC258249 OpenBabel07101718292D 22 25 0 0 0 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 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 1.7321 -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 3.8581 -0.2399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 10 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 22 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 14 16 1 0 0 0 0 14 17 2 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.05
Volume:	288.585
LogP:	3.888
LogD:	2.6
LogS:	-4.547
# Rotatable Bonds:	0
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	3.051
Fsp3:	0.059
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:	-4.926
MDCK Permeability:	1.05748304122244e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	90.47914123535156%
Volume Distribution (VD):	0.505
Pgp-substrate:	8.02490520477295%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.875
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.668
CYP2C9-substrate:	0.768
CYP2D6-inhibitor:	0.499
CYP2D6-substrate:	0.348
CYP3A4-inhibitor:	0.231
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	2.87
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.416
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.789
Rat Oral Acute Toxicity:	0.7
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.885
Carcinogencity:	0.813
Eye Corrosion:	0.004
Eye Irritation:	0.884
Respiratory Toxicity:	0.742

Download Data

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

Natural Product: NPC258249

Natural Product ID:	NPC258249
*Common Name:**	Euplectin
IUPAC Name:	5,11-dihydroxy-2-methylindeno[5,6-h]chromene-4,10-dione
Synonyms:	euplectin
Standard InCHIKey:	YMHHRZDSHVZLHL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H10O5/c1-7-4-11(19)15-12(20)6-9-5-8-2-3-10(18)13(8)16(21)14(9)17(15)22-7/h2-6,20-21H,1H3
SMILES:	Cc1cc(=O)c2c(o1)c1c(cc2O)cc2c(c1O)C(=O)C=C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519619
PubChem CID:	10732520
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO23276	Flavoparmelia euplecta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650094]
NPO23276	Flavoparmelia euplecta	Species	Parmeliaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4849	Cell Line	P815	Mus musculus	IC50	=	1.67	ug.mL-1	PMID[554179]

☑ 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 NPC258249 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	444
0.1-0.2	1923
0.2-0.3	4143
0.3-0.4	11192
0.4-0.5	7038
0.5-0.6	3870
0.6-0.7	5572
0.7-0.8	4662
0.8-0.85	2403
0.85-0.9	1242
0.9-0.95	194
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC7025
0.9655	High Similarity	NPC256672
0.9655	High Similarity	NPC27221
0.9589	High Similarity	NPC100985
0.9589	High Similarity	NPC65589
0.9589	High Similarity	NPC288036
0.9589	High Similarity	NPC97029
0.9589	High Similarity	NPC158338
0.9589	High Similarity	NPC97028
0.9586	High Similarity	NPC7943
0.9586	High Similarity	NPC123202
0.9586	High Similarity	NPC22005
0.9463	High Similarity	NPC169990
0.9463	High Similarity	NPC210942
0.9463	High Similarity	NPC329844
0.9456	High Similarity	NPC65775
0.9456	High Similarity	NPC10027
0.9333	High Similarity	NPC214632
0.9329	High Similarity	NPC474417
0.9329	High Similarity	NPC149526
0.9329	High Similarity	NPC72958
0.9329	High Similarity	NPC232645
0.9276	High Similarity	NPC164110
0.9276	High Similarity	NPC212967
0.9276	High Similarity	NPC246647
0.9276	High Similarity	NPC268360
0.9276	High Similarity	NPC96342
0.9267	High Similarity	NPC40356
0.9267	High Similarity	NPC154683
0.9267	High Similarity	NPC87708
0.9262	High Similarity	NPC325983
0.9247	High Similarity	NPC189650
0.9241	High Similarity	NPC94076
0.9241	High Similarity	NPC182255
0.9211	High Similarity	NPC180924
0.9205	High Similarity	NPC235333
0.92	High Similarity	NPC478148
0.9195	High Similarity	NPC329933
0.9195	High Similarity	NPC269420
0.9189	High Similarity	NPC126767
0.9189	High Similarity	NPC312929
0.9189	High Similarity	NPC56433
0.9189	High Similarity	NPC245584
0.9189	High Similarity	NPC289042
0.9189	High Similarity	NPC190648
0.9189	High Similarity	NPC34802
0.9189	High Similarity	NPC118027
0.9178	High Similarity	NPC84266
0.9178	High Similarity	NPC1534
0.9178	High Similarity	NPC310340
0.9172	High Similarity	NPC275734
0.9172	High Similarity	NPC270883
0.9172	High Similarity	NPC172986
0.9172	High Similarity	NPC261227
0.9167	High Similarity	NPC201395
0.9145	High Similarity	NPC213936
0.9145	High Similarity	NPC297531
0.9145	High Similarity	NPC148938
0.9145	High Similarity	NPC99199
0.9139	High Similarity	NPC217447
0.9133	High Similarity	NPC227122
0.9133	High Similarity	NPC255641
0.9133	High Similarity	NPC202595
0.9133	High Similarity	NPC158866
0.9133	High Similarity	NPC290954
0.9128	High Similarity	NPC37139
0.9128	High Similarity	NPC105415
0.9122	High Similarity	NPC196114
0.9116	High Similarity	NPC11700
0.911	High Similarity	NPC64908
0.911	High Similarity	NPC118840
0.911	High Similarity	NPC205006
0.911	High Similarity	NPC147688
0.911	High Similarity	NPC110969
0.911	High Similarity	NPC156590
0.9103	High Similarity	NPC301217
0.9103	High Similarity	NPC303633
0.9103	High Similarity	NPC96565
0.9103	High Similarity	NPC216978
0.9103	High Similarity	NPC220062
0.9103	High Similarity	NPC18260
0.9103	High Similarity	NPC78913
0.9103	High Similarity	NPC55018
0.9097	High Similarity	NPC228661
0.9091	High Similarity	NPC177650
0.9079	High Similarity	NPC95842
0.9079	High Similarity	NPC178964
0.9079	High Similarity	NPC472462
0.9079	High Similarity	NPC280530
0.9079	High Similarity	NPC72370
0.9073	High Similarity	NPC23668
0.9073	High Similarity	NPC193976
0.9073	High Similarity	NPC115324
0.9067	High Similarity	NPC233267
0.9067	High Similarity	NPC291049
0.9067	High Similarity	NPC474052
0.9067	High Similarity	NPC37208
0.9067	High Similarity	NPC221868
0.9054	High Similarity	NPC311741
0.9054	High Similarity	NPC234629
0.9048	High Similarity	NPC144499
0.9048	High Similarity	NPC473042
0.9048	High Similarity	NPC11561
0.9048	High Similarity	NPC226636
0.9041	High Similarity	NPC69769
0.9041	High Similarity	NPC159275
0.9041	High Similarity	NPC305355
0.9041	High Similarity	NPC235239
0.9041	High Similarity	NPC475680
0.9041	High Similarity	NPC241100
0.9032	High Similarity	NPC312993
0.9032	High Similarity	NPC186325
0.9026	High Similarity	NPC201127
0.902	High Similarity	NPC226656
0.902	High Similarity	NPC254351
0.902	High Similarity	NPC66508
0.9013	High Similarity	NPC207624
0.9013	High Similarity	NPC142308
0.9013	High Similarity	NPC142527
0.9013	High Similarity	NPC175978
0.9013	High Similarity	NPC45934
0.9007	High Similarity	NPC294646
0.9007	High Similarity	NPC101957
0.9007	High Similarity	NPC120105
0.9007	High Similarity	NPC147735
0.9007	High Similarity	NPC295036
0.9007	High Similarity	NPC470568
0.9007	High Similarity	NPC167576
0.9007	High Similarity	NPC230713
0.9007	High Similarity	NPC78335
0.9	High Similarity	NPC186397
0.9	High Similarity	NPC135325
0.9	High Similarity	NPC272194
0.9	High Similarity	NPC168085
0.9	High Similarity	NPC37135
0.8993	High Similarity	NPC130176
0.8993	High Similarity	NPC163846
0.8993	High Similarity	NPC210826
0.8993	High Similarity	NPC99454
0.8993	High Similarity	NPC477955
0.8993	High Similarity	NPC225173
0.8986	High Similarity	NPC190637
0.8986	High Similarity	NPC24821
0.8986	High Similarity	NPC225884
0.8986	High Similarity	NPC293053
0.8986	High Similarity	NPC18585
0.8986	High Similarity	NPC9117
0.8986	High Similarity	NPC219915
0.8986	High Similarity	NPC212932
0.8986	High Similarity	NPC166138
0.8986	High Similarity	NPC106985
0.8986	High Similarity	NPC19896
0.8986	High Similarity	NPC38219
0.898	High Similarity	NPC49108
0.898	High Similarity	NPC3188
0.898	High Similarity	NPC103362
0.898	High Similarity	NPC282300
0.8974	High Similarity	NPC273467
0.8974	High Similarity	NPC66288
0.8974	High Similarity	NPC189552
0.8973	High Similarity	NPC472366
0.8973	High Similarity	NPC295384
0.8973	High Similarity	NPC217186
0.8973	High Similarity	NPC53181
0.8968	High Similarity	NPC55443
0.8968	High Similarity	NPC474373
0.8968	High Similarity	NPC18699
0.8966	High Similarity	NPC250266
0.8966	High Similarity	NPC266597
0.8958	High Similarity	NPC242712
0.8954	High Similarity	NPC193200
0.8954	High Similarity	NPC93552
0.8954	High Similarity	NPC208806
0.8954	High Similarity	NPC135522
0.8947	High Similarity	NPC133856
0.8947	High Similarity	NPC170169
0.8947	High Similarity	NPC106372
0.8947	High Similarity	NPC230848
0.8947	High Similarity	NPC470569
0.8947	High Similarity	NPC154345
0.8947	High Similarity	NPC58668
0.8947	High Similarity	NPC305965
0.894	High Similarity	NPC266499
0.894	High Similarity	NPC70764
0.894	High Similarity	NPC223988
0.894	High Similarity	NPC317492
0.894	High Similarity	NPC178202
0.894	High Similarity	NPC473978
0.894	High Similarity	NPC80370
0.8933	High Similarity	NPC12148
0.8933	High Similarity	NPC201731
0.8933	High Similarity	NPC125801
0.8933	High Similarity	NPC97716
0.8933	High Similarity	NPC71055
0.8933	High Similarity	NPC237635
0.8933	High Similarity	NPC104406
0.8933	High Similarity	NPC79469
0.8933	High Similarity	NPC130581
0.8933	High Similarity	NPC259632
0.8933	High Similarity	NPC24673

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 NPC258249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	1016
0.2-0.3	1498
0.3-0.4	2703
0.4-0.5	1943
0.5-0.6	1053
0.6-0.7	344
0.7-0.8	127
0.8-0.85	53
0.85-0.9	14
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8926	High Similarity	NPD4378	Clinical (unspecified phase)
0.8831	High Similarity	NPD7819	Suspended
0.88	High Similarity	NPD7410	Clinical (unspecified phase)
0.8734	High Similarity	NPD6959	Discontinued
0.8699	High Similarity	NPD1510	Phase 2
0.869	High Similarity	NPD1607	Approved
0.8658	High Similarity	NPD3750	Approved
0.8649	High Similarity	NPD1549	Phase 2
0.8609	High Similarity	NPD1511	Approved
0.859	High Similarity	NPD2393	Clinical (unspecified phase)
0.8581	High Similarity	NPD1550	Clinical (unspecified phase)
0.8581	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD1509	Clinical (unspecified phase)
0.8552	High Similarity	NPD1240	Approved
0.8544	High Similarity	NPD3749	Approved
0.8523	High Similarity	NPD970	Clinical (unspecified phase)
0.8514	High Similarity	NPD2796	Approved
0.8497	Intermediate Similarity	NPD1512	Approved
0.8452	Intermediate Similarity	NPD3226	Approved
0.8447	Intermediate Similarity	NPD6232	Discontinued
0.8431	Intermediate Similarity	NPD2532	Approved
0.8431	Intermediate Similarity	NPD2533	Approved
0.8431	Intermediate Similarity	NPD2534	Approved
0.8418	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD1934	Approved
0.8405	Intermediate Similarity	NPD7473	Discontinued
0.8397	Intermediate Similarity	NPD4380	Phase 2
0.8354	Intermediate Similarity	NPD2801	Approved
0.8344	Intermediate Similarity	NPD7411	Suspended
0.8344	Intermediate Similarity	NPD1243	Approved
0.8344	Intermediate Similarity	NPD2800	Approved
0.8333	Intermediate Similarity	NPD2346	Discontinued
0.8322	Intermediate Similarity	NPD3748	Approved
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.825	Intermediate Similarity	NPD3882	Suspended
0.825	Intermediate Similarity	NPD7768	Phase 2
0.8247	Intermediate Similarity	NPD7390	Discontinued
0.8239	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2344	Approved
0.8193	Intermediate Similarity	NPD5844	Phase 1
0.8176	Intermediate Similarity	NPD6801	Discontinued
0.8165	Intermediate Similarity	NPD6599	Discontinued
0.8155	Intermediate Similarity	NPD6559	Discontinued
0.8146	Intermediate Similarity	NPD1551	Phase 2
0.8146	Intermediate Similarity	NPD6100	Approved
0.8146	Intermediate Similarity	NPD6099	Approved
0.8098	Intermediate Similarity	NPD5494	Approved
0.8095	Intermediate Similarity	NPD4625	Phase 3
0.8089	Intermediate Similarity	NPD920	Approved
0.8086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2935	Discontinued
0.8024	Intermediate Similarity	NPD3818	Discontinued
0.8013	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD2309	Approved
0.7987	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD3817	Phase 2
0.7962	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2799	Discontinued
0.7935	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD919	Approved
0.7919	Intermediate Similarity	NPD2313	Discontinued
0.7908	Intermediate Similarity	NPD5404	Approved
0.7908	Intermediate Similarity	NPD5406	Approved
0.7908	Intermediate Similarity	NPD5408	Approved
0.7908	Intermediate Similarity	NPD5405	Approved
0.7904	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6166	Phase 2
0.7901	Intermediate Similarity	NPD1465	Phase 2
0.7895	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD1247	Approved
0.7823	Intermediate Similarity	NPD1470	Approved
0.7815	Intermediate Similarity	NPD943	Approved
0.7793	Intermediate Similarity	NPD1201	Approved
0.7784	Intermediate Similarity	NPD5711	Approved
0.7784	Intermediate Similarity	NPD5710	Approved
0.7765	Intermediate Similarity	NPD7054	Approved
0.7764	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1471	Phase 3
0.7738	Intermediate Similarity	NPD3926	Phase 2
0.7727	Intermediate Similarity	NPD4308	Phase 3
0.7719	Intermediate Similarity	NPD7074	Phase 3
0.7719	Intermediate Similarity	NPD7472	Approved
0.7712	Intermediate Similarity	NPD6651	Approved
0.7707	Intermediate Similarity	NPD4628	Phase 3
0.7707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1203	Approved
0.7697	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6797	Phase 2
0.7674	Intermediate Similarity	NPD5953	Discontinued
0.7651	Intermediate Similarity	NPD2798	Approved
0.764	Intermediate Similarity	NPD5403	Approved
0.7636	Intermediate Similarity	NPD4288	Approved
0.7636	Intermediate Similarity	NPD5402	Approved
0.763	Intermediate Similarity	NPD7251	Discontinued
0.7625	Intermediate Similarity	NPD5401	Approved
0.7625	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7003	Approved
0.7586	Intermediate Similarity	NPD7808	Phase 3
0.7574	Intermediate Similarity	NPD7229	Phase 3
0.7566	Intermediate Similarity	NPD3268	Approved
0.7566	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3764	Approved
0.7566	Intermediate Similarity	NPD411	Approved
0.7558	Intermediate Similarity	NPD7286	Phase 2
0.7542	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4287	Approved
0.7517	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD7177	Discontinued
0.7486	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4307	Phase 2
0.7467	Intermediate Similarity	NPD2797	Approved
0.7466	Intermediate Similarity	NPD1651	Approved
0.745	Intermediate Similarity	NPD4749	Approved
0.7446	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD8312	Approved
0.7434	Intermediate Similarity	NPD4908	Phase 1
0.7432	Intermediate Similarity	NPD1610	Phase 2
0.7432	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD422	Phase 1
0.743	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2296	Approved
0.7423	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4361	Phase 2
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7397	Intermediate Similarity	NPD1548	Phase 1
0.7389	Intermediate Similarity	NPD7033	Discontinued
0.7383	Intermediate Similarity	NPD3972	Approved
0.7363	Intermediate Similarity	NPD4360	Phase 2
0.7363	Intermediate Similarity	NPD4363	Phase 3
0.7362	Intermediate Similarity	NPD6273	Approved
0.7351	Intermediate Similarity	NPD3266	Approved
0.7351	Intermediate Similarity	NPD1164	Approved
0.7351	Intermediate Similarity	NPD3267	Approved
0.7333	Intermediate Similarity	NPD7458	Discontinued
0.732	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6832	Phase 2
0.7315	Intermediate Similarity	NPD1281	Approved
0.731	Intermediate Similarity	NPD7199	Phase 2
0.7308	Intermediate Similarity	NPD447	Suspended
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD17	Approved
0.7296	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1876	Approved
0.7285	Intermediate Similarity	NPD3225	Approved
0.7273	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6780	Approved
0.7258	Intermediate Similarity	NPD6781	Approved
0.7258	Intermediate Similarity	NPD6777	Approved
0.7258	Intermediate Similarity	NPD6776	Approved
0.7258	Intermediate Similarity	NPD6782	Approved
0.7258	Intermediate Similarity	NPD6778	Approved
0.7258	Intermediate Similarity	NPD6779	Approved
0.7255	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8151	Discontinued
0.7216	Intermediate Similarity	NPD1729	Discontinued
0.7205	Intermediate Similarity	NPD2654	Approved
0.7202	Intermediate Similarity	NPD37	Approved
0.7197	Intermediate Similarity	NPD230	Phase 1
0.7195	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6234	Discontinued
0.7189	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4626	Approved
0.7176	Intermediate Similarity	NPD4967	Phase 2
0.7176	Intermediate Similarity	NPD4966	Approved
0.7176	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD3787	Discontinued
0.716	Intermediate Similarity	NPD5760	Phase 2
0.716	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD7697	Approved
0.7143	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1613	Approved
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7134	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2979	Phase 3
0.7127	Intermediate Similarity	NPD8434	Phase 2
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.7115	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1296	Phase 2
0.7105	Intermediate Similarity	NPD7870	Phase 2
0.7105	Intermediate Similarity	NPD7871	Phase 2
0.7099	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5123	Clinical (unspecified phase)

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