NPASS Compound

Structure

NPC260263 OpenBabel07101718312D 22 24 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 3.4641 0.0000 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 -0.0000 4.0000 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 3.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 0.8660 -1.5000 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 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 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 11 2 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 17 2 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 6 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	2.004
LogD:	1.37
LogS:	-3.425
# Rotatable Bonds:	2
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.382
Synthetic Accessibility Score:	3.151
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.085
MDCK Permeability:	1.0387167094449978e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.345
Human Intestinal Absorption (HIA):	0.117
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	88.99674224853516%
Volume Distribution (VD):	0.878
Pgp-substrate:	13.4733304977417%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.173
CYP2C9-inhibitor:	0.587
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.408
CYP2D6-substrate:	0.246
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	3.456
Half-life (T1/2):	0.733

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.584
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.406
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.667
Skin Sensitization:	0.589
Carcinogencity:	0.125
Eye Corrosion:	0.003
Eye Irritation:	0.428
Respiratory Toxicity:	0.189

Download Data

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

Natural Product: NPC260263

Natural Product ID:	NPC260263
*Common Name:**	Alternethanoxin A
IUPAC Name:	1-[(6R)-1,4,6-trihydroxy-7-methoxy-6H-benzo[c]chromen-2-yl]ethanone
Synonyms:
Standard InCHIKey:	VCSBQDYZRLMMNP-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-7(17)9-6-10(18)15-13(14(9)19)8-4-3-5-11(21-2)12(8)16(20)22-15/h3-6,16,18-20H,1-2H3/t16-/m1/s1
SMILES:	CC(=O)c1cc(c2c(-c3cccc(c3[C@H](O)O2)OC)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2251689
PubChem CID:	44226794
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans

*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
NPO13026	Alternaria sonchi	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19594161]
NPO13026	Alternaria sonchi	Species	Pleosporaceae	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	9

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6442	Organism	Phleum pratense	Phleum pratense	Activity	=	1.0	mm	PMID[521559]
NPT6543	Organism	Elymus repens	Elymus repens	Activity	=	1.0	mm	PMID[521559]
NPT6354	Organism	Aegopodium podagraria	Aegopodium podagraria	Activity	=	1.0	mm	PMID[521559]
NPT131	Organism	Convolvulus arvensis	Convolvulus arvensis	Activity	=	1.0	mm	PMID[521559]
NPT132	Organism	Amaranthus retroflexus	Amaranthus retroflexus	Activity	=	1.0	mm	PMID[521559]
NPT126	Organism	Taraxacum officinale	Taraxacum officinale	Activity	=	1.0	mm	PMID[521559]
NPT6572	Organism	Calendula officinalis	Calendula officinalis	Activity	=	1.0	mm	PMID[521559]
NPT2537	Organism	Cirsium arvense	Cirsium arvense	Activity	=	1.0	mm	PMID[521559]
NPT2538	Organism	Sonchus arvensis	Sonchus arvensis	Activity	=	4.0	mm	PMID[521559]

☑ 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 NPC260263 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	421
0.1-0.2	1812
0.2-0.3	4077
0.3-0.4	9935
0.4-0.5	8247
0.5-0.6	3390
0.6-0.7	4808
0.7-0.8	5657
0.8-0.85	2613
0.85-0.9	1566
0.9-0.95	169
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9578	High Similarity	NPC183843
0.9448	High Similarity	NPC471288
0.9383	High Similarity	NPC7483
0.9317	High Similarity	NPC14353
0.9317	High Similarity	NPC56085
0.9317	High Similarity	NPC228785
0.9277	High Similarity	NPC205076
0.9277	High Similarity	NPC48773
0.9277	High Similarity	NPC307518
0.9273	High Similarity	NPC471287
0.9264	High Similarity	NPC220313
0.9264	High Similarity	NPC470772
0.9259	High Similarity	NPC61010
0.9259	High Similarity	NPC40491
0.9259	High Similarity	NPC474187
0.9259	High Similarity	NPC278052
0.9255	High Similarity	NPC100123
0.9231	High Similarity	NPC212290
0.9217	High Similarity	NPC183357
0.9217	High Similarity	NPC22195
0.9217	High Similarity	NPC34287
0.9217	High Similarity	NPC44558
0.9217	High Similarity	NPC474434
0.9217	High Similarity	NPC21190
0.9217	High Similarity	NPC224462
0.9217	High Similarity	NPC105511
0.9217	High Similarity	NPC471416
0.9212	High Similarity	NPC477154
0.9212	High Similarity	NPC117854
0.9212	High Similarity	NPC6588
0.9207	High Similarity	NPC165720
0.9207	High Similarity	NPC326520
0.9207	High Similarity	NPC275780
0.9207	High Similarity	NPC472450
0.9207	High Similarity	NPC239752
0.9202	High Similarity	NPC294965
0.9198	High Similarity	NPC474287
0.9198	High Similarity	NPC320359
0.9198	High Similarity	NPC475886
0.9198	High Similarity	NPC36217
0.9193	High Similarity	NPC241904
0.9193	High Similarity	NPC210084
0.9193	High Similarity	NPC262286
0.9193	High Similarity	NPC300727
0.9193	High Similarity	NPC36852
0.9193	High Similarity	NPC78225
0.9193	High Similarity	NPC217677
0.9193	High Similarity	NPC99597
0.9193	High Similarity	NPC165977
0.9187	High Similarity	NPC2928
0.9172	High Similarity	NPC168584
0.9167	High Similarity	NPC472607
0.9157	High Similarity	NPC229687
0.9157	High Similarity	NPC112755
0.9157	High Similarity	NPC469931
0.9157	High Similarity	NPC45638
0.9157	High Similarity	NPC186807
0.9157	High Similarity	NPC475942
0.9157	High Similarity	NPC170675
0.9157	High Similarity	NPC210042
0.9157	High Similarity	NPC201292
0.9157	High Similarity	NPC105025
0.9157	High Similarity	NPC93337
0.9157	High Similarity	NPC472381
0.9157	High Similarity	NPC95855
0.9157	High Similarity	NPC472383
0.9157	High Similarity	NPC183036
0.9157	High Similarity	NPC58053
0.9157	High Similarity	NPC226294
0.9157	High Similarity	NPC471457
0.9152	High Similarity	NPC39091
0.9152	High Similarity	NPC170245
0.9146	High Similarity	NPC147596
0.9146	High Similarity	NPC270837
0.9146	High Similarity	NPC236132
0.9146	High Similarity	NPC197168
0.9146	High Similarity	NPC236521
0.9146	High Similarity	NPC152659
0.9146	High Similarity	NPC470178
0.9146	High Similarity	NPC189473
0.9146	High Similarity	NPC248638
0.9146	High Similarity	NPC88043
0.9146	High Similarity	NPC23298
0.9141	High Similarity	NPC475883
0.9141	High Similarity	NPC266314
0.9141	High Similarity	NPC474186
0.9141	High Similarity	NPC474351
0.9141	High Similarity	NPC162668
0.9141	High Similarity	NPC308992
0.9141	High Similarity	NPC471290
0.9141	High Similarity	NPC32694
0.9136	High Similarity	NPC476242
0.9136	High Similarity	NPC95936
0.9136	High Similarity	NPC329091
0.9136	High Similarity	NPC250214
0.913	High Similarity	NPC255106
0.913	High Similarity	NPC68093
0.913	High Similarity	NPC191146
0.913	High Similarity	NPC274730
0.913	High Similarity	NPC472916
0.913	High Similarity	NPC142339
0.913	High Similarity	NPC138243
0.913	High Similarity	NPC235165
0.9125	High Similarity	NPC88645
0.9125	High Similarity	NPC206238
0.9125	High Similarity	NPC292214
0.9125	High Similarity	NPC271779
0.9125	High Similarity	NPC167091
0.9107	High Similarity	NPC239549
0.9107	High Similarity	NPC51774
0.9107	High Similarity	NPC236191
0.9102	High Similarity	NPC212748
0.9096	High Similarity	NPC45400
0.9096	High Similarity	NPC477502
0.9096	High Similarity	NPC42892
0.9096	High Similarity	NPC247973
0.9096	High Similarity	NPC116745
0.9096	High Similarity	NPC229729
0.9096	High Similarity	NPC58716
0.9096	High Similarity	NPC146792
0.9096	High Similarity	NPC93099
0.9096	High Similarity	NPC45618
0.9096	High Similarity	NPC135345
0.9091	High Similarity	NPC470773
0.9091	High Similarity	NPC25361
0.9085	High Similarity	NPC300537
0.9085	High Similarity	NPC472964
0.9085	High Similarity	NPC469575
0.9085	High Similarity	NPC127782
0.9085	High Similarity	NPC201800
0.9085	High Similarity	NPC329760
0.9085	High Similarity	NPC61594
0.9085	High Similarity	NPC56735
0.9085	High Similarity	NPC472448
0.9085	High Similarity	NPC25152
0.9085	High Similarity	NPC83922
0.9085	High Similarity	NPC229632
0.9085	High Similarity	NPC215612
0.908	High Similarity	NPC321399
0.908	High Similarity	NPC235018
0.908	High Similarity	NPC472902
0.908	High Similarity	NPC45146
0.908	High Similarity	NPC476980
0.908	High Similarity	NPC139036
0.908	High Similarity	NPC263449
0.9074	High Similarity	NPC474208
0.9074	High Similarity	NPC472911
0.9074	High Similarity	NPC162869
0.9074	High Similarity	NPC48208
0.9074	High Similarity	NPC474055
0.9074	High Similarity	NPC222814
0.9074	High Similarity	NPC472914
0.9074	High Similarity	NPC223787
0.9074	High Similarity	NPC245758
0.9074	High Similarity	NPC181960
0.9074	High Similarity	NPC474836
0.9074	High Similarity	NPC96167
0.9074	High Similarity	NPC299520
0.9074	High Similarity	NPC475267
0.9074	High Similarity	NPC469584
0.9074	High Similarity	NPC472913
0.9074	High Similarity	NPC129684
0.9074	High Similarity	NPC472910
0.9074	High Similarity	NPC156057
0.9074	High Similarity	NPC136674
0.9074	High Similarity	NPC291508
0.9074	High Similarity	NPC472598
0.9074	High Similarity	NPC236796
0.9068	High Similarity	NPC57674
0.9068	High Similarity	NPC39184
0.9068	High Similarity	NPC113906
0.9068	High Similarity	NPC117992
0.9068	High Similarity	NPC230149
0.9068	High Similarity	NPC152951
0.9068	High Similarity	NPC168247
0.9062	High Similarity	NPC101996
0.9062	High Similarity	NPC120537
0.9062	High Similarity	NPC39007
0.9062	High Similarity	NPC199100
0.9062	High Similarity	NPC161277
0.9062	High Similarity	NPC180234
0.9053	High Similarity	NPC108202
0.9053	High Similarity	NPC146803
0.9048	High Similarity	NPC475825
0.9048	High Similarity	NPC223375
0.9048	High Similarity	NPC267254
0.9048	High Similarity	NPC172807
0.9048	High Similarity	NPC476405
0.9048	High Similarity	NPC472386
0.9048	High Similarity	NPC254540
0.9048	High Similarity	NPC211594
0.9048	High Similarity	NPC117260
0.9048	High Similarity	NPC256760
0.9048	High Similarity	NPC301683
0.9042	High Similarity	NPC165979
0.9042	High Similarity	NPC163130
0.9036	High Similarity	NPC236934
0.9036	High Similarity	NPC5778
0.9036	High Similarity	NPC277480
0.9036	High Similarity	NPC472449

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 NPC260263 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	971
0.2-0.3	1910
0.3-0.4	2630
0.4-0.5	1742
0.5-0.6	912
0.6-0.7	396
0.7-0.8	150
0.8-0.85	29
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8982	High Similarity	NPD3818	Discontinued
0.8944	High Similarity	NPD1934	Approved
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.8889	High Similarity	NPD2801	Approved
0.8876	High Similarity	NPD7074	Phase 3
0.883	High Similarity	NPD4338	Clinical (unspecified phase)
0.8817	High Similarity	NPD7054	Approved
0.8765	High Similarity	NPD7472	Approved
0.8706	High Similarity	NPD5844	Phase 1
0.8623	High Similarity	NPD5494	Approved
0.8614	High Similarity	NPD4381	Clinical (unspecified phase)
0.8605	High Similarity	NPD6797	Phase 2
0.8555	High Similarity	NPD7251	Discontinued
0.8554	High Similarity	NPD3882	Suspended
0.8529	High Similarity	NPD6168	Clinical (unspecified phase)
0.8529	High Similarity	NPD6166	Phase 2
0.8529	High Similarity	NPD6167	Clinical (unspecified phase)
0.8521	High Similarity	NPD6232	Discontinued
0.8506	High Similarity	NPD7808	Phase 3
0.848	Intermediate Similarity	NPD7473	Discontinued
0.8448	Intermediate Similarity	NPD6559	Discontinued
0.8447	Intermediate Similarity	NPD1511	Approved
0.8434	Intermediate Similarity	NPD1465	Phase 2
0.8434	Intermediate Similarity	NPD7819	Suspended
0.8382	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD4380	Phase 2
0.8344	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7075	Discontinued
0.8274	Intermediate Similarity	NPD3817	Phase 2
0.8232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD6959	Discontinued
0.814	Intermediate Similarity	NPD1247	Approved
0.8137	Intermediate Similarity	NPD1549	Phase 2
0.8114	Intermediate Similarity	NPD3751	Discontinued
0.8075	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6801	Discontinued
0.7988	Intermediate Similarity	NPD7411	Suspended
0.7978	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD3749	Approved
0.7953	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD5402	Approved
0.795	Intermediate Similarity	NPD1510	Phase 2
0.7944	Intermediate Similarity	NPD8313	Approved
0.7944	Intermediate Similarity	NPD8312	Approved
0.7931	Intermediate Similarity	NPD7199	Phase 2
0.7926	Intermediate Similarity	NPD6782	Approved
0.7926	Intermediate Similarity	NPD6776	Approved
0.7926	Intermediate Similarity	NPD6780	Approved
0.7926	Intermediate Similarity	NPD6781	Approved
0.7926	Intermediate Similarity	NPD6778	Approved
0.7926	Intermediate Similarity	NPD6777	Approved
0.7926	Intermediate Similarity	NPD6779	Approved
0.7919	Intermediate Similarity	NPD919	Approved
0.7919	Intermediate Similarity	NPD6234	Discontinued
0.7917	Intermediate Similarity	NPD1653	Approved
0.791	Intermediate Similarity	NPD7228	Approved
0.7898	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6799	Approved
0.7886	Intermediate Similarity	NPD3787	Discontinued
0.7844	Intermediate Similarity	NPD2533	Approved
0.7844	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD2534	Approved
0.7844	Intermediate Similarity	NPD2532	Approved
0.7836	Intermediate Similarity	NPD37	Approved
0.7824	Intermediate Similarity	NPD6599	Discontinued
0.7818	Intermediate Similarity	NPD3750	Approved
0.7812	Intermediate Similarity	NPD943	Approved
0.7812	Intermediate Similarity	NPD1240	Approved
0.7805	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7768	Phase 2
0.7803	Intermediate Similarity	NPD4965	Approved
0.7803	Intermediate Similarity	NPD4967	Phase 2
0.7803	Intermediate Similarity	NPD4966	Approved
0.7801	Intermediate Similarity	NPD7435	Discontinued
0.7791	Intermediate Similarity	NPD2935	Discontinued
0.7791	Intermediate Similarity	NPD2796	Approved
0.7784	Intermediate Similarity	NPD8151	Discontinued
0.7765	Intermediate Similarity	NPD3226	Approved
0.776	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2346	Discontinued
0.774	Intermediate Similarity	NPD3926	Phase 2
0.774	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1607	Approved
0.7708	Intermediate Similarity	NPD7696	Phase 3
0.7708	Intermediate Similarity	NPD7697	Approved
0.7708	Intermediate Similarity	NPD7698	Approved
0.7704	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD7783	Phase 2
0.7702	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1613	Approved
0.7668	Intermediate Similarity	NPD7871	Phase 2
0.7668	Intermediate Similarity	NPD7870	Phase 2
0.766	Intermediate Similarity	NPD6534	Approved
0.766	Intermediate Similarity	NPD6535	Approved
0.7656	Intermediate Similarity	NPD6823	Phase 2
0.7654	Intermediate Similarity	NPD230	Phase 1
0.7651	Intermediate Similarity	NPD2800	Approved
0.7647	Intermediate Similarity	NPD920	Approved
0.7641	Intermediate Similarity	NPD7701	Phase 2
0.7637	Intermediate Similarity	NPD7685	Pre-registration
0.7622	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7874	Approved
0.7562	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1933	Approved
0.7546	Intermediate Similarity	NPD447	Suspended
0.7545	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5403	Approved
0.7539	Intermediate Similarity	NPD7699	Phase 2
0.7539	Intermediate Similarity	NPD7700	Phase 2
0.7529	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5401	Approved
0.7525	Intermediate Similarity	NPD7801	Approved
0.7515	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1551	Phase 2
0.7446	Intermediate Similarity	NPD7240	Approved
0.744	Intermediate Similarity	NPD1243	Approved
0.7433	Intermediate Similarity	NPD8150	Discontinued
0.7425	Intermediate Similarity	NPD2344	Approved
0.7421	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6212	Phase 3
0.7421	Intermediate Similarity	NPD6213	Phase 3
0.7412	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7584	Approved
0.741	Intermediate Similarity	NPD2799	Discontinued
0.7407	Intermediate Similarity	NPD3027	Phase 3
0.7391	Intermediate Similarity	NPD5953	Discontinued
0.7389	Intermediate Similarity	NPD5711	Approved
0.7389	Intermediate Similarity	NPD5710	Approved
0.7386	Intermediate Similarity	NPD8455	Phase 2
0.7377	Intermediate Similarity	NPD7286	Phase 2
0.7368	Intermediate Similarity	NPD7390	Discontinued
0.7362	Intermediate Similarity	NPD2313	Discontinued
0.7356	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6190	Approved
0.734	Intermediate Similarity	NPD8434	Phase 2
0.7337	Intermediate Similarity	NPD6674	Discontinued
0.7326	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7229	Phase 3
0.7284	Intermediate Similarity	NPD9494	Approved
0.7262	Intermediate Similarity	NPD6100	Approved
0.7262	Intermediate Similarity	NPD6099	Approved
0.7257	Intermediate Similarity	NPD7458	Discontinued
0.7256	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD2309	Approved
0.7222	Intermediate Similarity	NPD8319	Approved
0.7222	Intermediate Similarity	NPD8320	Phase 1
0.7219	Intermediate Similarity	NPD7266	Discontinued
0.7198	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4625	Phase 3
0.7193	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5242	Approved
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2798	Approved
0.7113	Intermediate Similarity	NPD4360	Phase 2
0.7113	Intermediate Similarity	NPD4363	Phase 3
0.71	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7680	Approved
0.7083	Intermediate Similarity	NPD4287	Approved
0.7083	Intermediate Similarity	NPD6651	Approved
0.7073	Intermediate Similarity	NPD7930	Approved
0.7066	Intermediate Similarity	NPD4060	Phase 1
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD5405	Approved
0.7055	Intermediate Similarity	NPD1470	Approved
0.7055	Intermediate Similarity	NPD1203	Approved
0.7048	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6844	Discontinued
0.7037	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5005	Approved
0.7035	Intermediate Similarity	NPD5006	Approved
0.703	Intermediate Similarity	NPD4908	Phase 1
0.703	Intermediate Similarity	NPD7585	Approved
0.7028	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8059	Phase 3
0.7024	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4665	Approved
0.7019	Intermediate Similarity	NPD1610	Phase 2
0.7019	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4111	Phase 1
0.7018	Intermediate Similarity	NPD2343	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