NPASS Compound

Structure

NPC204350 OpenBabel07101719522D 21 23 0 0 0 0 0 0 0 0999 V2000 4.5760 2.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3972 2.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9459 2.5896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2156 1.4115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3349 3.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 1.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9209 2.3671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3349 2.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2658 1.8565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3972 3.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 3.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 0.6784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2632 3.7219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 4.7219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8302 -0.2771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4972 -0.7913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6010 3.1001 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 20 1 0 0 0 0 2 7 2 0 0 0 0 2 11 1 0 0 0 0 3 8 2 0 0 0 0 3 10 1 0 0 0 0 4 8 1 0 0 0 0 4 13 2 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 7 1 0 0 0 0 6 21 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 10 14 2 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 15 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:	288.06
Volume:	276.613
LogP:	2.955
LogD:	2.681
LogS:	-3.698
# Rotatable Bonds:	1
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.549
Synthetic Accessibility Score:	2.584
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.951
MDCK Permeability:	9.334126843896229e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	97.5485610961914%
Volume Distribution (VD):	0.655
Pgp-substrate:	3.981879711151123%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.183
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.513
CYP2C9-substrate:	0.773
CYP2D6-inhibitor:	0.72
CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.432
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	14.582
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.054
Drug-inuced Liver Injury (DILI):	0.873
AMES Toxicity:	0.656
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.253
Skin Sensitization:	0.905
Carcinogencity:	0.043
Eye Corrosion:	0.007
Eye Irritation:	0.948
Respiratory Toxicity:	0.072

Download Data

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

Natural Product: NPC204350

Natural Product ID:	NPC204350
*Common Name:**	Alterlactone
IUPAC Name:	2,3,8-trihydroxy-10-methoxy-5H-benzo[d][2]benzoxepin-7-one
Synonyms:	Alterlactone
Standard InCHIKey:	JAAWVSLYMPCCOD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O6/c1-20-8-3-10-9-5-12(17)11(16)2-7(9)6-21-15(19)14(10)13(18)4-8/h2-5,16-18H,6H2,1H3
SMILES:	COc1cc2-c3cc(c(cc3COC(=O)c2c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507058
PubChem CID:	24899917
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001910] Benzoxepines [CHEMONTID:0001988] Dibenzoxepines

*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
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18494522]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276679]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25265160]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841051]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30794407]

☑ 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	24
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	23
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	Activity	=	11.8	%	PMID[542001]
NPT1660	Individual Protein	NUAK family SNF1-like kinase 1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1432	Individual Protein	Serine/threonine-protein kinase Aurora-A	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1434	Individual Protein	Serine/threonine-protein kinase B-raf	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT2572	Individual Protein	Ephrin type-B receptor 4	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1436	Individual Protein	Focal adhesion kinase 1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT2571	Individual Protein	Mitogen-activated protein kinase kinase kinase 8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1438	Individual Protein	Insulin-like growth factor I receptor	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT2573	Individual Protein	Vascular endothelial growth factor receptor 3	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1650	Individual Protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT2574	Individual Protein	Insulin receptor	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT2575	Individual Protein	Platelet-derived growth factor receptor beta	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1598	Individual Protein	Casein kinase II alpha	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1702	Individual Protein	Serine/threonine-protein kinase PLK4	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT2576	Individual Protein	Tyrosine-protein kinase TIE-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT728	Individual Protein	Serine/threonine-protein kinase AKT	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT1560	Protein Complex	Cyclin-dependent kinase 4/cyclin D1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[542001]

☑ 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 NPC204350 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	373
0.1-0.2	1721
0.2-0.3	4101
0.3-0.4	9356
0.4-0.5	8770
0.5-0.6	3340
0.6-0.7	5071
0.7-0.8	6701
0.8-0.85	2513
0.85-0.9	699
0.9-0.95	49
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9653	High Similarity	NPC138978
0.9338	High Similarity	NPC227062
0.9281	High Similarity	NPC200594
0.9272	High Similarity	NPC20541
0.9216	High Similarity	NPC238381
0.9205	High Similarity	NPC281477
0.9189	High Similarity	NPC476463
0.9145	High Similarity	NPC16082
0.9145	High Similarity	NPC82592
0.9145	High Similarity	NPC199926
0.9139	High Similarity	NPC295646
0.9133	High Similarity	NPC96501
0.9116	High Similarity	NPC257025
0.9085	High Similarity	NPC54928
0.9085	High Similarity	NPC150227
0.9034	High Similarity	NPC471819
0.9028	High Similarity	NPC135837
0.9026	High Similarity	NPC84935
0.9026	High Similarity	NPC190020
0.9026	High Similarity	NPC77679
0.902	High Similarity	NPC67396
0.902	High Similarity	NPC79998
0.902	High Similarity	NPC38898
0.902	High Similarity	NPC471800
0.9013	High Similarity	NPC167903
0.9007	High Similarity	NPC119929
0.9007	High Similarity	NPC85131
0.8993	High Similarity	NPC267509
0.8981	High Similarity	NPC156082
0.898	High Similarity	NPC250755
0.8968	High Similarity	NPC83763
0.8968	High Similarity	NPC168616
0.8968	High Similarity	NPC45846
0.8961	High Similarity	NPC24640
0.8958	High Similarity	NPC223836
0.8947	High Similarity	NPC202157
0.894	High Similarity	NPC270160
0.894	High Similarity	NPC237440
0.8926	High Similarity	NPC134621
0.8926	High Similarity	NPC32470
0.8924	High Similarity	NPC112981
0.8924	High Similarity	NPC8070
0.8919	High Similarity	NPC469542
0.8919	High Similarity	NPC51106
0.8919	High Similarity	NPC287722
0.8912	High Similarity	NPC67650
0.8912	High Similarity	NPC1704
0.8912	High Similarity	NPC220106
0.8912	High Similarity	NPC90411
0.8889	High Similarity	NPC289968
0.8889	High Similarity	NPC28103
0.8889	High Similarity	NPC199773
0.8889	High Similarity	NPC180905
0.8889	High Similarity	NPC182496
0.8882	High Similarity	NPC151473
0.8874	High Similarity	NPC321011
0.8874	High Similarity	NPC188679
0.8874	High Similarity	NPC294852
0.8868	High Similarity	NPC20216
0.8867	High Similarity	NPC260946
0.8867	High Similarity	NPC237208
0.8861	High Similarity	NPC300984
0.8859	High Similarity	NPC66404
0.8859	High Similarity	NPC210425
0.8859	High Similarity	NPC95123
0.8859	High Similarity	NPC86373
0.8859	High Similarity	NPC280404
0.8859	High Similarity	NPC277426
0.8859	High Similarity	NPC242893
0.8859	High Similarity	NPC38065
0.8854	High Similarity	NPC303565
0.8851	High Similarity	NPC301178
0.8851	High Similarity	NPC284556
0.8851	High Similarity	NPC105648
0.8846	High Similarity	NPC315157
0.8846	High Similarity	NPC85121
0.8846	High Similarity	NPC329091
0.8846	High Similarity	NPC210459
0.8831	High Similarity	NPC89474
0.8831	High Similarity	NPC93552
0.8824	High Similarity	NPC215921
0.8824	High Similarity	NPC70016
0.8816	High Similarity	NPC1612
0.8816	High Similarity	NPC183959
0.8812	High Similarity	NPC272485
0.8812	High Similarity	NPC292788
0.8808	High Similarity	NPC108406
0.8805	High Similarity	NPC267153
0.88	High Similarity	NPC29577
0.8797	High Similarity	NPC93739
0.8792	High Similarity	NPC175013
0.8792	High Similarity	NPC472006
0.8792	High Similarity	NPC471417
0.879	High Similarity	NPC24627
0.879	High Similarity	NPC471744
0.879	High Similarity	NPC321399
0.879	High Similarity	NPC292415
0.879	High Similarity	NPC36217
0.8782	High Similarity	NPC111969
0.8782	High Similarity	NPC247713
0.8782	High Similarity	NPC241904
0.8782	High Similarity	NPC300727
0.8776	High Similarity	NPC134969
0.8776	High Similarity	NPC247409
0.8774	High Similarity	NPC80534
0.8774	High Similarity	NPC16286
0.8774	High Similarity	NPC56786
0.8773	High Similarity	NPC139350
0.8766	High Similarity	NPC260979
0.8766	High Similarity	NPC175978
0.8766	High Similarity	NPC106976
0.8766	High Similarity	NPC273483
0.8766	High Similarity	NPC302950
0.8766	High Similarity	NPC219582
0.8766	High Similarity	NPC236637
0.8758	High Similarity	NPC469619
0.8758	High Similarity	NPC62042
0.8758	High Similarity	NPC469670
0.8758	High Similarity	NPC470107
0.8758	High Similarity	NPC26568
0.8758	High Similarity	NPC10467
0.875	High Similarity	NPC80710
0.875	High Similarity	NPC203747
0.875	High Similarity	NPC254702
0.875	High Similarity	NPC203077
0.875	High Similarity	NPC3036
0.875	High Similarity	NPC194653
0.875	High Similarity	NPC287395
0.875	High Similarity	NPC107636
0.875	High Similarity	NPC218490
0.875	High Similarity	NPC119059
0.875	High Similarity	NPC183655
0.875	High Similarity	NPC120464
0.875	High Similarity	NPC139364
0.875	High Similarity	NPC172329
0.875	High Similarity	NPC166036
0.875	High Similarity	NPC2569
0.875	High Similarity	NPC238279
0.875	High Similarity	NPC472452
0.875	High Similarity	NPC153783
0.8742	High Similarity	NPC32058
0.8742	High Similarity	NPC284007
0.8742	High Similarity	NPC107625
0.8742	High Similarity	NPC163846
0.8742	High Similarity	NPC234004
0.8742	High Similarity	NPC225173
0.8742	High Similarity	NPC85734
0.8734	High Similarity	NPC473106
0.8734	High Similarity	NPC349525
0.8734	High Similarity	NPC112418
0.8734	High Similarity	NPC103201
0.8733	High Similarity	NPC279121
0.8726	High Similarity	NPC37502
0.8726	High Similarity	NPC470339
0.8726	High Similarity	NPC476242
0.8726	High Similarity	NPC40702
0.8726	High Similarity	NPC267627
0.8725	High Similarity	NPC182255
0.8725	High Similarity	NPC469579
0.8725	High Similarity	NPC94076
0.8725	High Similarity	NPC474385
0.8725	High Similarity	NPC82913
0.8718	High Similarity	NPC475799
0.8718	High Similarity	NPC13779
0.8718	High Similarity	NPC142339
0.8718	High Similarity	NPC197751
0.8718	High Similarity	NPC153512
0.8718	High Similarity	NPC472456
0.8718	High Similarity	NPC274730
0.8716	High Similarity	NPC155205
0.8716	High Similarity	NPC165172
0.871	High Similarity	NPC144801
0.871	High Similarity	NPC213896
0.871	High Similarity	NPC291510
0.871	High Similarity	NPC192083
0.871	High Similarity	NPC116850
0.871	High Similarity	NPC107109
0.871	High Similarity	NPC469550
0.871	High Similarity	NPC18727
0.871	High Similarity	NPC298802
0.871	High Similarity	NPC197188
0.871	High Similarity	NPC192189
0.871	High Similarity	NPC298692
0.871	High Similarity	NPC74924
0.871	High Similarity	NPC238672
0.871	High Similarity	NPC43872
0.8704	High Similarity	NPC10576
0.8704	High Similarity	NPC1827
0.8704	High Similarity	NPC17219
0.8704	High Similarity	NPC239440
0.8704	High Similarity	NPC20543
0.8704	High Similarity	NPC246716
0.8701	High Similarity	NPC200773
0.8701	High Similarity	NPC204515
0.8701	High Similarity	NPC227166
0.8701	High Similarity	NPC240768
0.8701	High Similarity	NPC45291
0.8701	High Similarity	NPC272566
0.8701	High Similarity	NPC19980
0.8699	High Similarity	NPC235115

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 NPC204350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	970
0.2-0.3	1816
0.3-0.4	2605
0.4-0.5	1726
0.5-0.6	1067
0.6-0.7	426
0.7-0.8	141
0.8-0.85	35
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8904	High Similarity	NPD970	Clinical (unspecified phase)
0.8766	High Similarity	NPD1934	Approved
0.8733	High Similarity	NPD1511	Approved
0.871	High Similarity	NPD2393	Clinical (unspecified phase)
0.8679	High Similarity	NPD6232	Discontinued
0.8618	High Similarity	NPD1512	Approved
0.859	High Similarity	NPD1465	Phase 2
0.8519	High Similarity	NPD7473	Discontinued
0.8493	Intermediate Similarity	NPD230	Phase 1
0.8481	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD2801	Approved
0.8431	Intermediate Similarity	NPD2532	Approved
0.8431	Intermediate Similarity	NPD2533	Approved
0.8431	Intermediate Similarity	NPD2534	Approved
0.8418	Intermediate Similarity	NPD3817	Phase 2
0.8365	Intermediate Similarity	NPD3882	Suspended
0.8354	Intermediate Similarity	NPD7819	Suspended
0.8322	Intermediate Similarity	NPD1510	Phase 2
0.8299	Intermediate Similarity	NPD1240	Approved
0.8232	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6166	Phase 2
0.8232	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD5844	Phase 1
0.8188	Intermediate Similarity	NPD1607	Approved
0.8176	Intermediate Similarity	NPD943	Approved
0.8158	Intermediate Similarity	NPD1549	Phase 2
0.8144	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD3818	Discontinued
0.8129	Intermediate Similarity	NPD6799	Approved
0.8086	Intermediate Similarity	NPD7075	Discontinued
0.8084	Intermediate Similarity	NPD7054	Approved
0.8079	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD3750	Approved
0.805	Intermediate Similarity	NPD6599	Discontinued
0.805	Intermediate Similarity	NPD4380	Phase 2
0.8049	Intermediate Similarity	NPD6959	Discontinued
0.8036	Intermediate Similarity	NPD7472	Approved
0.8026	Intermediate Similarity	NPD2935	Discontinued
0.8026	Intermediate Similarity	NPD1551	Phase 2
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7988	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3749	Approved
0.7941	Intermediate Similarity	NPD7251	Discontinued
0.7927	Intermediate Similarity	NPD919	Approved
0.7927	Intermediate Similarity	NPD6234	Discontinued
0.7914	Intermediate Similarity	NPD7768	Phase 2
0.7888	Intermediate Similarity	NPD7411	Suspended
0.7866	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6801	Discontinued
0.7821	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2796	Approved
0.7791	Intermediate Similarity	NPD7808	Phase 3
0.7784	Intermediate Similarity	NPD5711	Approved
0.7784	Intermediate Similarity	NPD5710	Approved
0.7771	Intermediate Similarity	NPD5494	Approved
0.7763	Intermediate Similarity	NPD447	Suspended
0.7756	Intermediate Similarity	NPD1243	Approved
0.775	Intermediate Similarity	NPD920	Approved
0.7744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD9269	Phase 2
0.773	Intermediate Similarity	NPD37	Approved
0.7727	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3748	Approved
0.7727	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7199	Phase 2
0.7718	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4628	Phase 3
0.7697	Intermediate Similarity	NPD1613	Approved
0.7697	Intermediate Similarity	NPD4966	Approved
0.7697	Intermediate Similarity	NPD4965	Approved
0.7697	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4967	Phase 2
0.7667	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3226	Approved
0.7643	Intermediate Similarity	NPD2800	Approved
0.764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5402	Approved
0.7633	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6559	Discontinued
0.7625	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1247	Approved
0.7616	Intermediate Similarity	NPD3027	Phase 3
0.7613	Intermediate Similarity	NPD2799	Discontinued
0.761	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7228	Approved
0.7584	Intermediate Similarity	NPD1203	Approved
0.7562	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7390	Discontinued
0.7558	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5403	Approved
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7516	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5401	Approved
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1608	Approved
0.7483	Intermediate Similarity	NPD9494	Approved
0.7466	Intermediate Similarity	NPD9268	Approved
0.7458	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6190	Approved
0.7427	Intermediate Similarity	NPD5242	Approved
0.7419	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2344	Approved
0.74	Intermediate Similarity	NPD1283	Approved
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7397	Intermediate Similarity	NPD9545	Approved
0.7383	Intermediate Similarity	NPD9717	Approved
0.7375	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6651	Approved
0.7371	Intermediate Similarity	NPD5953	Discontinued
0.7368	Intermediate Similarity	NPD7229	Phase 3
0.7356	Intermediate Similarity	NPD7286	Phase 2
0.7342	Intermediate Similarity	NPD5405	Approved
0.7342	Intermediate Similarity	NPD6099	Approved
0.7342	Intermediate Similarity	NPD5406	Approved
0.7342	Intermediate Similarity	NPD5404	Approved
0.7342	Intermediate Similarity	NPD6100	Approved
0.7342	Intermediate Similarity	NPD5408	Approved
0.7338	Intermediate Similarity	NPD3764	Approved
0.732	Intermediate Similarity	NPD6832	Phase 2
0.7316	Intermediate Similarity	NPD8151	Discontinued
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7308	Intermediate Similarity	NPD1933	Approved
0.7301	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD1653	Approved
0.7267	Intermediate Similarity	NPD3787	Discontinued
0.726	Intermediate Similarity	NPD9493	Approved
0.7244	Intermediate Similarity	NPD4060	Phase 1
0.7237	Intermediate Similarity	NPD1164	Approved
0.7232	Intermediate Similarity	NPD7685	Pre-registration
0.7229	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD411	Approved
0.7226	Intermediate Similarity	NPD2313	Discontinued
0.7222	Intermediate Similarity	NPD2309	Approved
0.7219	Intermediate Similarity	NPD4288	Approved
0.7219	Intermediate Similarity	NPD5353	Approved
0.72	Intermediate Similarity	NPD1201	Approved
0.72	Intermediate Similarity	NPD1610	Phase 2
0.72	Intermediate Similarity	NPD1281	Approved
0.717	Intermediate Similarity	NPD7033	Discontinued
0.7166	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7003	Approved
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD6386	Approved
0.7143	Intermediate Similarity	NPD6385	Approved
0.7135	Intermediate Similarity	NPD7240	Approved
0.7134	Intermediate Similarity	NPD2979	Phase 3
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.7125	Intermediate Similarity	NPD4477	Approved
0.7125	Intermediate Similarity	NPD4476	Approved
0.7124	Intermediate Similarity	NPD1470	Approved
0.7124	Intermediate Similarity	NPD2797	Approved
0.7115	Intermediate Similarity	NPD3268	Approved
0.7115	Intermediate Similarity	NPD1296	Phase 2
0.7111	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4908	Phase 1
0.7095	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7078	Intermediate Similarity	NPD1019	Discontinued
0.7078	Intermediate Similarity	NPD2798	Approved
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7055	Intermediate Similarity	NPD8166	Discontinued
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7051	Intermediate Similarity	NPD4625	Phase 3
0.7049	Intermediate Similarity	NPD4287	Approved
0.7048	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1548	Phase 1
0.7033	Intermediate Similarity	NPD8434	Phase 2
0.7024	Intermediate Similarity	NPD7458	Discontinued
0.7019	Intermediate Similarity	NPD2438	Suspended
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.7006	Intermediate Similarity	NPD7177	Discontinued
0.7006	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2654	Approved
0.6984	Remote Similarity	NPD6781	Approved
0.6984	Remote Similarity	NPD6777	Approved
0.6984	Remote Similarity	NPD6779	Approved
0.6984	Remote Similarity	NPD6776	Approved
0.6984	Remote Similarity	NPD6782	Approved
0.6984	Remote Similarity	NPD6780	Approved
0.6984	Remote Similarity	NPD6778	Approved
0.6975	Remote Similarity	NPD7266	Discontinued
0.6975	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7783	Phase 2
0.6954	Remote Similarity	NPD6746	Phase 2

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