NPASS Compound

Structure

NPC476310 OpenBabel07101718282D 21 23 0 0 1 0 0 0 0 0999 V2000 -0.7029 1.1785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4242 1.6397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6810 0.9706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2902 1.1397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2038 1.5464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 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 -3.0823 0.1615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 7 1 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 7 1 1 1 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 8 1 6 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.08
Volume:	279.249
LogP:	2.563
LogD:	1.451
LogS:	-2.861
# Rotatable Bonds:	3
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.663
Synthetic Accessibility Score:	4.231
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.905
MDCK Permeability:	1.5603911379002966e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	81.09414672851562%
Volume Distribution (VD):	1.039
Pgp-substrate:	15.870268821716309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.504
CYP1A2-substrate:	0.41
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.226
CYP2C9-inhibitor:	0.169
CYP2C9-substrate:	0.849
CYP2D6-inhibitor:	0.081
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.527
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	11.85
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.55
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.182
Rat Oral Acute Toxicity:	0.658
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.608
Carcinogencity:	0.517
Eye Corrosion:	0.007
Eye Irritation:	0.17
Respiratory Toxicity:	0.225

Download Data

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

Natural Product: NPC476310

Natural Product ID:	NPC476310
*Common Name:**	Photinide C
IUPAC Name:	(2Z)-4-hydroxy-2-[2-hydroxy-1-[(2R,3R)-3-methyl-5-oxooxolan-2-yl]ethylidene]-1-benzofuran-3-one
Synonyms:	Photinide C
Standard InCHIKey:	VDEOWZAVWBRZOK-XIIPNMQHSA-N
Standard InCHI:	InChI=1S/C15H14O6/c1-7-5-11(18)21-14(7)8(6-16)15-13(19)12-9(17)3-2-4-10(12)20-15/h2-4,7,14,16-17H,5-6H2,1H3/b15-8-/t7-,14-/m1/s1
SMILES:	OC/C(=C1/Oc2c(C1=O)c(O)ccc2)/[C@@H]1OC(=O)C[C@H]1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563583
PubChem CID:	44140406
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO16031	Pestalotiopsis photiniae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19371070]
NPO16031	Pestalotiopsis photiniae	Species	Sporocadaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	23.1	%	PMID[557094]

☑ 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 NPC476310 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	300
0.1-0.2	1235
0.2-0.3	3505
0.3-0.4	8398
0.4-0.5	10488
0.5-0.6	4544
0.6-0.7	6833
0.7-0.8	6726
0.8-0.85	643
0.85-0.9	21
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476164
0.9783	High Similarity	NPC105381
0.9783	High Similarity	NPC10302
0.8936	High Similarity	NPC287068
0.8733	High Similarity	NPC275878
0.8732	High Similarity	NPC240147
0.8732	High Similarity	NPC121243
0.8716	High Similarity	NPC228012
0.8699	High Similarity	NPC470216
0.8675	High Similarity	NPC301233
0.8667	High Similarity	NPC295650
0.8667	High Similarity	NPC470380
0.8658	High Similarity	NPC477941
0.8639	High Similarity	NPC71210
0.8639	High Similarity	NPC316535
0.8633	High Similarity	NPC12694
0.8611	High Similarity	NPC268691
0.8603	High Similarity	NPC6888
0.8601	High Similarity	NPC470397
0.86	High Similarity	NPC475717
0.8582	High Similarity	NPC128216
0.8562	High Similarity	NPC150023
0.8562	High Similarity	NPC313922
0.8562	High Similarity	NPC310128
0.8552	High Similarity	NPC137009
0.8552	High Similarity	NPC230902
0.8552	High Similarity	NPC37206
0.8542	High Similarity	NPC254841
0.8521	High Similarity	NPC223457
0.8503	High Similarity	NPC130206
0.8503	High Similarity	NPC471520
0.8497	Intermediate Similarity	NPC237560
0.8497	Intermediate Similarity	NPC474542
0.8497	Intermediate Similarity	NPC473241
0.8493	Intermediate Similarity	NPC103342
0.8493	Intermediate Similarity	NPC146679
0.8493	Intermediate Similarity	NPC103904
0.8493	Intermediate Similarity	NPC184536
0.8493	Intermediate Similarity	NPC59951
0.8493	Intermediate Similarity	NPC90411
0.8493	Intermediate Similarity	NPC230285
0.8477	Intermediate Similarity	NPC116822
0.8472	Intermediate Similarity	NPC470398
0.8472	Intermediate Similarity	NPC187826
0.8462	Intermediate Similarity	NPC248872
0.8462	Intermediate Similarity	NPC144027
0.8462	Intermediate Similarity	NPC236974
0.8456	Intermediate Similarity	NPC153758
0.8451	Intermediate Similarity	NPC203817
0.8451	Intermediate Similarity	NPC25937
0.8442	Intermediate Similarity	NPC154341
0.844	Intermediate Similarity	NPC198249
0.8435	Intermediate Similarity	NPC262094
0.8435	Intermediate Similarity	NPC229916
0.8435	Intermediate Similarity	NPC136840
0.8435	Intermediate Similarity	NPC90582
0.8429	Intermediate Similarity	NPC187907
0.8425	Intermediate Similarity	NPC241838
0.8425	Intermediate Similarity	NPC143799
0.8425	Intermediate Similarity	NPC152042
0.8421	Intermediate Similarity	NPC290671
0.8414	Intermediate Similarity	NPC332594
0.8414	Intermediate Similarity	NPC98395
0.8411	Intermediate Similarity	NPC470461
0.8403	Intermediate Similarity	NPC223616
0.84	Intermediate Similarity	NPC3779
0.84	Intermediate Similarity	NPC211466
0.84	Intermediate Similarity	NPC210320
0.84	Intermediate Similarity	NPC40086
0.84	Intermediate Similarity	NPC44721
0.84	Intermediate Similarity	NPC476182
0.84	Intermediate Similarity	NPC176869
0.84	Intermediate Similarity	NPC122828
0.8389	Intermediate Similarity	NPC297788
0.8389	Intermediate Similarity	NPC49130
0.8389	Intermediate Similarity	NPC208176
0.8389	Intermediate Similarity	NPC326506
0.8389	Intermediate Similarity	NPC62290
0.8389	Intermediate Similarity	NPC4152
0.8389	Intermediate Similarity	NPC142731
0.8389	Intermediate Similarity	NPC279417
0.8389	Intermediate Similarity	NPC306607
0.8387	Intermediate Similarity	NPC476930
0.8387	Intermediate Similarity	NPC473395
0.838	Intermediate Similarity	NPC475589
0.838	Intermediate Similarity	NPC31872
0.838	Intermediate Similarity	NPC473584
0.8378	Intermediate Similarity	NPC162476
0.8378	Intermediate Similarity	NPC472344
0.8369	Intermediate Similarity	NPC42292
0.8369	Intermediate Similarity	NPC307732
0.8367	Intermediate Similarity	NPC307990
0.8367	Intermediate Similarity	NPC281207
0.8367	Intermediate Similarity	NPC269652
0.8367	Intermediate Similarity	NPC470856
0.8367	Intermediate Similarity	NPC16455
0.8367	Intermediate Similarity	NPC244923
0.8357	Intermediate Similarity	NPC293453
0.8356	Intermediate Similarity	NPC470399
0.8355	Intermediate Similarity	NPC474735
0.8354	Intermediate Similarity	NPC109180
0.8345	Intermediate Similarity	NPC187432
0.8345	Intermediate Similarity	NPC256042
0.8345	Intermediate Similarity	NPC216361
0.8345	Intermediate Similarity	NPC156910
0.8345	Intermediate Similarity	NPC116775
0.8345	Intermediate Similarity	NPC281917
0.8344	Intermediate Similarity	NPC470460
0.8344	Intermediate Similarity	NPC215711
0.8344	Intermediate Similarity	NPC73411
0.8344	Intermediate Similarity	NPC191634
0.8333	Intermediate Similarity	NPC148011
0.8333	Intermediate Similarity	NPC470458
0.8333	Intermediate Similarity	NPC1940
0.8322	Intermediate Similarity	NPC470909
0.8322	Intermediate Similarity	NPC113770
0.8322	Intermediate Similarity	NPC474939
0.8322	Intermediate Similarity	NPC96216
0.8311	Intermediate Similarity	NPC474385
0.8311	Intermediate Similarity	NPC171870
0.831	Intermediate Similarity	NPC137264
0.831	Intermediate Similarity	NPC5515
0.831	Intermediate Similarity	NPC270369
0.8302	Intermediate Similarity	NPC72016
0.8301	Intermediate Similarity	NPC240768
0.8301	Intermediate Similarity	NPC39819
0.8301	Intermediate Similarity	NPC200773
0.8299	Intermediate Similarity	NPC329203
0.8299	Intermediate Similarity	NPC150648
0.8299	Intermediate Similarity	NPC274784
0.8299	Intermediate Similarity	NPC222342
0.8299	Intermediate Similarity	NPC265871
0.8299	Intermediate Similarity	NPC20709
0.8299	Intermediate Similarity	NPC310135
0.8299	Intermediate Similarity	NPC139554
0.8299	Intermediate Similarity	NPC225153
0.8298	Intermediate Similarity	NPC197425
0.8298	Intermediate Similarity	NPC69235
0.8298	Intermediate Similarity	NPC212379
0.8291	Intermediate Similarity	NPC27942
0.8289	Intermediate Similarity	NPC198927
0.8289	Intermediate Similarity	NPC317492
0.8289	Intermediate Similarity	NPC4423
0.8289	Intermediate Similarity	NPC77325
0.8289	Intermediate Similarity	NPC73236
0.8288	Intermediate Similarity	NPC107586
0.8288	Intermediate Similarity	NPC32441
0.8288	Intermediate Similarity	NPC287246
0.8288	Intermediate Similarity	NPC299379
0.8288	Intermediate Similarity	NPC13768
0.8288	Intermediate Similarity	NPC243083
0.8288	Intermediate Similarity	NPC79943
0.8288	Intermediate Similarity	NPC296490
0.8288	Intermediate Similarity	NPC295261
0.8288	Intermediate Similarity	NPC188879
0.8288	Intermediate Similarity	NPC12296
0.8286	Intermediate Similarity	NPC128428
0.8286	Intermediate Similarity	NPC305518
0.8278	Intermediate Similarity	NPC472036
0.8278	Intermediate Similarity	NPC146884
0.8278	Intermediate Similarity	NPC61284
0.8278	Intermediate Similarity	NPC14098
0.8278	Intermediate Similarity	NPC113428
0.8278	Intermediate Similarity	NPC202494
0.8276	Intermediate Similarity	NPC60667
0.8276	Intermediate Similarity	NPC84699
0.8276	Intermediate Similarity	NPC266245
0.8269	Intermediate Similarity	NPC269495
0.8269	Intermediate Similarity	NPC288084
0.8267	Intermediate Similarity	NPC470554
0.8267	Intermediate Similarity	NPC118059
0.8267	Intermediate Similarity	NPC184649
0.8267	Intermediate Similarity	NPC311144
0.8267	Intermediate Similarity	NPC133060
0.8267	Intermediate Similarity	NPC98926
0.8267	Intermediate Similarity	NPC288910
0.8267	Intermediate Similarity	NPC303185
0.8267	Intermediate Similarity	NPC470857
0.8258	Intermediate Similarity	NPC99381
0.8255	Intermediate Similarity	NPC294432
0.8255	Intermediate Similarity	NPC472006
0.8255	Intermediate Similarity	NPC51106
0.8255	Intermediate Similarity	NPC470556
0.8252	Intermediate Similarity	NPC65060
0.8252	Intermediate Similarity	NPC113006
0.8247	Intermediate Similarity	NPC217149
0.8247	Intermediate Similarity	NPC271681
0.8247	Intermediate Similarity	NPC216035
0.8247	Intermediate Similarity	NPC281272
0.8243	Intermediate Similarity	NPC307287
0.8243	Intermediate Similarity	NPC6407
0.8243	Intermediate Similarity	NPC284550
0.8243	Intermediate Similarity	NPC76445
0.8243	Intermediate Similarity	NPC145673
0.8243	Intermediate Similarity	NPC110228
0.8243	Intermediate Similarity	NPC129853
0.8243	Intermediate Similarity	NPC188243
0.8239	Intermediate Similarity	NPC91288
0.8239	Intermediate Similarity	NPC146615
0.8239	Intermediate Similarity	NPC39753

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 NPC476310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	811
0.2-0.3	1771
0.3-0.4	2556
0.4-0.5	2071
0.5-0.6	1153
0.6-0.7	381
0.7-0.8	139
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD5403	Approved
0.8389	Intermediate Similarity	NPD5401	Approved
0.8367	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1551	Phase 2
0.8322	Intermediate Similarity	NPD6799	Approved
0.8288	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD5402	Approved
0.8231	Intermediate Similarity	NPD1549	Phase 2
0.8188	Intermediate Similarity	NPD9717	Approved
0.8153	Intermediate Similarity	NPD7075	Discontinued
0.8146	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6801	Discontinued
0.8108	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD3882	Suspended
0.8077	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1203	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD1240	Approved
0.7922	Intermediate Similarity	NPD920	Approved
0.7911	Intermediate Similarity	NPD3817	Phase 2
0.7908	Intermediate Similarity	NPD2532	Approved
0.7908	Intermediate Similarity	NPD2534	Approved
0.7908	Intermediate Similarity	NPD2533	Approved
0.7905	Intermediate Similarity	NPD1510	Phase 2
0.7891	Intermediate Similarity	NPD1607	Approved
0.7857	Intermediate Similarity	NPD1512	Approved
0.7834	Intermediate Similarity	NPD7411	Suspended
0.7832	Intermediate Similarity	NPD1019	Discontinued
0.7823	Intermediate Similarity	NPD447	Suspended
0.7815	Intermediate Similarity	NPD2800	Approved
0.781	Intermediate Similarity	NPD9493	Approved
0.7792	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1934	Approved
0.7763	Intermediate Similarity	NPD3750	Approved
0.774	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2796	Approved
0.773	Intermediate Similarity	NPD422	Phase 1
0.7727	Intermediate Similarity	NPD1511	Approved
0.7724	Intermediate Similarity	NPD6832	Phase 2
0.7711	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD3749	Approved
0.7702	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1243	Approved
0.7688	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6004	Phase 3
0.7682	Intermediate Similarity	NPD6005	Phase 3
0.7682	Intermediate Similarity	NPD6002	Phase 3
0.7682	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4380	Phase 2
0.7654	Intermediate Similarity	NPD919	Approved
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.764	Intermediate Similarity	NPD7768	Phase 2
0.7636	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6166	Phase 2
0.7636	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7819	Suspended
0.7625	Intermediate Similarity	NPD2801	Approved
0.7619	Intermediate Similarity	NPD6797	Phase 2
0.7619	Intermediate Similarity	NPD2313	Discontinued
0.7619	Intermediate Similarity	NPD411	Approved
0.7574	Intermediate Similarity	NPD7251	Discontinued
0.7574	Intermediate Similarity	NPD6559	Discontinued
0.7564	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2799	Discontinued
0.755	Intermediate Similarity	NPD7033	Discontinued
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD230	Phase 1
0.7466	Intermediate Similarity	NPD5647	Approved
0.7455	Intermediate Similarity	NPD1247	Approved
0.7451	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD9545	Approved
0.7434	Intermediate Similarity	NPD3748	Approved
0.7425	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2797	Approved
0.7396	Intermediate Similarity	NPD7286	Phase 2
0.7396	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD5494	Approved
0.7383	Intermediate Similarity	NPD3268	Approved
0.7375	Intermediate Similarity	NPD3226	Approved
0.7353	Intermediate Similarity	NPD7472	Approved
0.7353	Intermediate Similarity	NPD7074	Phase 3
0.7351	Intermediate Similarity	NPD5124	Phase 1
0.7351	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6355	Discontinued
0.7338	Intermediate Similarity	NPD2344	Approved
0.7338	Intermediate Similarity	NPD2346	Discontinued
0.7321	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5953	Discontinued
0.731	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7303	Intermediate Similarity	NPD6651	Approved
0.7284	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7473	Discontinued
0.7267	Intermediate Similarity	NPD1296	Phase 2
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7246	Intermediate Similarity	NPD6959	Discontinued
0.7244	Intermediate Similarity	NPD2654	Approved
0.7244	Intermediate Similarity	NPD1652	Phase 2
0.7237	Intermediate Similarity	NPD1933	Approved
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD74	Approved
0.7226	Intermediate Similarity	NPD9266	Approved
0.7225	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7212	Intermediate Similarity	NPD4966	Approved
0.7212	Intermediate Similarity	NPD4967	Phase 2
0.7212	Intermediate Similarity	NPD4965	Approved
0.7211	Intermediate Similarity	NPD3225	Approved
0.7208	Intermediate Similarity	NPD4308	Phase 3
0.7203	Intermediate Similarity	NPD1548	Phase 1
0.7202	Intermediate Similarity	NPD5710	Approved
0.7202	Intermediate Similarity	NPD5711	Approved
0.7202	Intermediate Similarity	NPD6232	Discontinued
0.7192	Intermediate Similarity	NPD1608	Approved
0.7162	Intermediate Similarity	NPD3266	Approved
0.7162	Intermediate Similarity	NPD3267	Approved
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7153	Intermediate Similarity	NPD9264	Approved
0.7153	Intermediate Similarity	NPD9263	Approved
0.7153	Intermediate Similarity	NPD9267	Approved
0.7152	Intermediate Similarity	NPD2309	Approved
0.7152	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7127	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6234	Discontinued
0.7123	Intermediate Similarity	NPD1610	Phase 2
0.7118	Intermediate Similarity	NPD2403	Approved
0.7114	Intermediate Similarity	NPD2798	Approved
0.7103	Intermediate Similarity	NPD1778	Approved
0.7097	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5844	Phase 1
0.7092	Intermediate Similarity	NPD1241	Discontinued
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.7075	Intermediate Similarity	NPD1481	Phase 2
0.7059	Intermediate Similarity	NPD3926	Phase 2
0.7059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3496	Discontinued
0.7055	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6100	Approved
0.7051	Intermediate Similarity	NPD6099	Approved
0.7047	Intermediate Similarity	NPD6362	Approved
0.7039	Intermediate Similarity	NPD3764	Approved
0.703	Intermediate Similarity	NPD37	Approved
0.702	Intermediate Similarity	NPD4908	Phase 1
0.702	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1535	Discovery
0.7007	Intermediate Similarity	NPD1091	Approved
0.7006	Intermediate Similarity	NPD1471	Phase 3
0.7	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3787	Discontinued
0.6993	Remote Similarity	NPD4062	Phase 3
0.6988	Remote Similarity	NPD1465	Phase 2
0.6986	Remote Similarity	NPD17	Approved
0.6968	Remote Similarity	NPD6653	Approved
0.6954	Remote Similarity	NPD1729	Discontinued
0.6948	Remote Similarity	NPD4307	Phase 2
0.6948	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD943	Approved
0.6948	Remote Similarity	NPD1613	Approved
0.6941	Remote Similarity	NPD7199	Phase 2
0.6936	Remote Similarity	NPD7228	Approved
0.6928	Remote Similarity	NPD6844	Discontinued
0.6928	Remote Similarity	NPD1048	Approved
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9281	Approved
0.6906	Remote Similarity	NPD290	Approved
0.6901	Remote Similarity	NPD7229	Phase 3
0.6899	Remote Similarity	NPD5763	Approved
0.6899	Remote Similarity	NPD5762	Approved
0.689	Remote Similarity	NPD1653	Approved
0.6886	Remote Similarity	NPD5761	Phase 2
0.6886	Remote Similarity	NPD5760	Phase 2
0.6883	Remote Similarity	NPD520	Approved
0.6861	Remote Similarity	NPD9261	Approved
0.6855	Remote Similarity	NPD2424	Discontinued
0.6849	Remote Similarity	NPD1894	Discontinued
0.6845	Remote Similarity	NPD4288	Approved
0.6839	Remote Similarity	NPD4060	Phase 1
0.6832	Remote Similarity	NPD6190	Approved
0.6832	Remote Similarity	NPD3887	Approved
0.6832	Remote Similarity	NPD2354	Approved
0.6831	Remote Similarity	NPD4363	Phase 3
0.6831	Remote Similarity	NPD4360	Phase 2
0.6829	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8055	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