NPASS Compound

Structure

NPC474340 OpenBabel07101719242D 22 24 0 0 0 0 0 0 0 0999 V2000 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 2.0000 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 0.5000 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 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 11 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 16 2 0 0 0 0 10 15 2 0 0 0 0 10 22 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 18 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.1
Volume:	308.284
LogP:	3.955
LogD:	3.159
LogS:	-5.413
# Rotatable Bonds:	3
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	1.983
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.733
MDCK Permeability:	3.830048444797285e-05
Pgp-inhibitor:	0.33
Pgp-substrate:	0.953
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.677

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.116
Plasma Protein Binding (PPB):	93.53199005126953%
Volume Distribution (VD):	0.416
Pgp-substrate:	3.662410020828247%

ADMET: Metabolism

CYP1A2-inhibitor:	0.807
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.74
CYP2C19-substrate:	0.137
CYP2C9-inhibitor:	0.746
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.595
CYP2D6-substrate:	0.939
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.488

ADMET: Excretion

Clearance (CL):	4.793
Half-life (T1/2):	0.202

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.876
AMES Toxicity:	0.39
Rat Oral Acute Toxicity:	0.225
Maximum Recommended Daily Dose:	0.636
Skin Sensitization:	0.448
Carcinogencity:	0.315
Eye Corrosion:	0.006
Eye Irritation:	0.903
Respiratory Toxicity:	0.365

Download Data

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

Natural Product: NPC474340

Natural Product ID:	NPC474340
*Common Name:**	7-O-Methylafromosin
IUPAC Name:	6-methoxy-3-(4-methoxyphenyl)-7-methylchromen-4-one
Synonyms:	7-O-Methylafromosin
Standard InCHIKey:	JMBQERKOHQZKCY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O4/c1-11-8-17-14(9-16(11)21-3)18(19)15(10-22-17)12-4-6-13(20-2)7-5-12/h4-10H,1-3H3
SMILES:	COc1ccc(cc1)c1coc2c(c1=O)cc(c(c2)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465447
PubChem CID:	44567059
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0002687] 4'-O-methylisoflavones

*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
NPO20912	Wisteria brachybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2853205]
NPO20912	Wisteria brachybotrys	Species	Fabaceae	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	10

Activity Type	# Activity
Cell Line	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	22.7	%	PMID[488941]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	100.0	%	PMID[488941]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[488941]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	0.0	%	PMID[488941]
NPT2	Others	Unspecified		Activity	=	1.0	%	PMID[488941]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[488941]
NPT2	Others	Unspecified		Activity	=	95.0	%	PMID[488941]
NPT2	Others	Unspecified		Activity	=	66.8	%	PMID[488941]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[488941]

☑ 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 NPC474340 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	500
0.1-0.2	1913
0.2-0.3	5008
0.3-0.4	12476
0.4-0.5	5103
0.5-0.6	5167
0.6-0.7	7343
0.7-0.8	4792
0.8-0.85	366
0.85-0.9	24
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.952	High Similarity	NPC474264
0.9206	High Similarity	NPC56332
0.9141	High Similarity	NPC298884
0.9008	High Similarity	NPC301717
0.888	High Similarity	NPC201284
0.88	High Similarity	NPC171023
0.8768	High Similarity	NPC149780
0.8723	High Similarity	NPC195919
0.8723	High Similarity	NPC216314
0.8723	High Similarity	NPC120924
0.8712	High Similarity	NPC57552
0.8702	High Similarity	NPC45537
0.8692	High Similarity	NPC224657
0.8667	High Similarity	NPC1249
0.8667	High Similarity	NPC223354
0.8647	High Similarity	NPC7569
0.8633	High Similarity	NPC124365
0.8603	High Similarity	NPC22222
0.8603	High Similarity	NPC281513
0.8593	High Similarity	NPC182428
0.8582	High Similarity	NPC141549
0.8582	High Similarity	NPC182842
0.855	High Similarity	NPC2771
0.854	High Similarity	NPC77955
0.8521	High Similarity	NPC49282
0.8519	High Similarity	NPC183103
0.8507	High Similarity	NPC278787
0.85	High Similarity	NPC171094
0.8496	Intermediate Similarity	NPC125887
0.8489	Intermediate Similarity	NPC223336
0.8478	Intermediate Similarity	NPC254741
0.8478	Intermediate Similarity	NPC301341
0.8462	Intermediate Similarity	NPC469758
0.8462	Intermediate Similarity	NPC300540
0.8451	Intermediate Similarity	NPC23955
0.8444	Intermediate Similarity	NPC477412
0.844	Intermediate Similarity	NPC185607
0.8438	Intermediate Similarity	NPC54243
0.8429	Intermediate Similarity	NPC109232
0.8425	Intermediate Similarity	NPC262623
0.8425	Intermediate Similarity	NPC469954
0.8406	Intermediate Similarity	NPC324929
0.8403	Intermediate Similarity	NPC478018
0.8403	Intermediate Similarity	NPC205522
0.84	Intermediate Similarity	NPC279916
0.8397	Intermediate Similarity	NPC182646
0.8392	Intermediate Similarity	NPC478019
0.8392	Intermediate Similarity	NPC469764
0.8385	Intermediate Similarity	NPC314329
0.8382	Intermediate Similarity	NPC472882
0.838	Intermediate Similarity	NPC53016
0.838	Intermediate Similarity	NPC167663
0.8369	Intermediate Similarity	NPC58229
0.8359	Intermediate Similarity	NPC32298
0.8358	Intermediate Similarity	NPC475017
0.8357	Intermediate Similarity	NPC309154
0.8357	Intermediate Similarity	NPC55162
0.8357	Intermediate Similarity	NPC278323
0.8357	Intermediate Similarity	NPC1268
0.8357	Intermediate Similarity	NPC90665
0.8357	Intermediate Similarity	NPC12175
0.8357	Intermediate Similarity	NPC279668
0.8356	Intermediate Similarity	NPC10467
0.8356	Intermediate Similarity	NPC156953
0.8356	Intermediate Similarity	NPC239363
0.8346	Intermediate Similarity	NPC474737
0.8346	Intermediate Similarity	NPC177925
0.8345	Intermediate Similarity	NPC10304
0.8345	Intermediate Similarity	NPC474107
0.8345	Intermediate Similarity	NPC471542
0.8345	Intermediate Similarity	NPC284184
0.8345	Intermediate Similarity	NPC55327
0.8345	Intermediate Similarity	NPC63256
0.8333	Intermediate Similarity	NPC4012
0.8333	Intermediate Similarity	NPC215932
0.8333	Intermediate Similarity	NPC110639
0.8333	Intermediate Similarity	NPC40818
0.8333	Intermediate Similarity	NPC14958
0.8333	Intermediate Similarity	NPC106461
0.8311	Intermediate Similarity	NPC477691
0.8311	Intermediate Similarity	NPC135522
0.8311	Intermediate Similarity	NPC478213
0.8311	Intermediate Similarity	NPC186507
0.8311	Intermediate Similarity	NPC124714
0.831	Intermediate Similarity	NPC469404
0.831	Intermediate Similarity	NPC268204
0.831	Intermediate Similarity	NPC26051
0.831	Intermediate Similarity	NPC52789
0.831	Intermediate Similarity	NPC214919
0.831	Intermediate Similarity	NPC124467
0.831	Intermediate Similarity	NPC55832
0.8309	Intermediate Similarity	NPC164295
0.8309	Intermediate Similarity	NPC239134
0.8296	Intermediate Similarity	NPC211120
0.8295	Intermediate Similarity	NPC35744
0.8288	Intermediate Similarity	NPC238366
0.8288	Intermediate Similarity	NPC266499
0.8288	Intermediate Similarity	NPC474052
0.8286	Intermediate Similarity	NPC303644
0.8286	Intermediate Similarity	NPC7013
0.8286	Intermediate Similarity	NPC209560
0.8286	Intermediate Similarity	NPC116632
0.8286	Intermediate Similarity	NPC294409
0.8286	Intermediate Similarity	NPC181124
0.8286	Intermediate Similarity	NPC162680
0.8286	Intermediate Similarity	NPC212767
0.8284	Intermediate Similarity	NPC470841
0.8276	Intermediate Similarity	NPC85233
0.8273	Intermediate Similarity	NPC141934
0.8273	Intermediate Similarity	NPC232996
0.8267	Intermediate Similarity	NPC44199
0.8264	Intermediate Similarity	NPC471590
0.8264	Intermediate Similarity	NPC136278
0.8261	Intermediate Similarity	NPC292998
0.8252	Intermediate Similarity	NPC476054
0.8252	Intermediate Similarity	NPC277369
0.8252	Intermediate Similarity	NPC215451
0.8248	Intermediate Similarity	NPC118253
0.8243	Intermediate Similarity	NPC269451
0.8243	Intermediate Similarity	NPC477690
0.8243	Intermediate Similarity	NPC291802
0.8243	Intermediate Similarity	NPC153008
0.8243	Intermediate Similarity	NPC121522
0.8243	Intermediate Similarity	NPC209487
0.8243	Intermediate Similarity	NPC131266
0.8243	Intermediate Similarity	NPC216769
0.8243	Intermediate Similarity	NPC245382
0.8243	Intermediate Similarity	NPC100263
0.8243	Intermediate Similarity	NPC35763
0.8243	Intermediate Similarity	NPC100971
0.8243	Intermediate Similarity	NPC148497
0.8243	Intermediate Similarity	NPC181209
0.8239	Intermediate Similarity	NPC253822
0.8239	Intermediate Similarity	NPC259166
0.8239	Intermediate Similarity	NPC172250
0.8239	Intermediate Similarity	NPC145673
0.8239	Intermediate Similarity	NPC219917
0.8239	Intermediate Similarity	NPC326109
0.8239	Intermediate Similarity	NPC80962
0.8239	Intermediate Similarity	NPC215311
0.8239	Intermediate Similarity	NPC204985
0.8239	Intermediate Similarity	NPC213659
0.8239	Intermediate Similarity	NPC144118
0.8239	Intermediate Similarity	NPC101366
0.8239	Intermediate Similarity	NPC48624
0.8231	Intermediate Similarity	NPC294646
0.8231	Intermediate Similarity	NPC470092
0.8231	Intermediate Similarity	NPC37348
0.8227	Intermediate Similarity	NPC477408
0.8227	Intermediate Similarity	NPC470407
0.8219	Intermediate Similarity	NPC218490
0.8219	Intermediate Similarity	NPC186397
0.8219	Intermediate Similarity	NPC37135
0.8214	Intermediate Similarity	NPC472364
0.8214	Intermediate Similarity	NPC193792
0.8214	Intermediate Similarity	NPC473391
0.8214	Intermediate Similarity	NPC186647
0.8214	Intermediate Similarity	NPC87545
0.8214	Intermediate Similarity	NPC130976
0.8214	Intermediate Similarity	NPC235428
0.8207	Intermediate Similarity	NPC196114
0.8207	Intermediate Similarity	NPC283002
0.8207	Intermediate Similarity	NPC99454
0.8207	Intermediate Similarity	NPC60389
0.8207	Intermediate Similarity	NPC130176
0.8207	Intermediate Similarity	NPC302408
0.8207	Intermediate Similarity	NPC231013
0.8201	Intermediate Similarity	NPC89504
0.8201	Intermediate Similarity	NPC125269
0.8201	Intermediate Similarity	NPC88065
0.8201	Intermediate Similarity	NPC95485
0.8194	Intermediate Similarity	NPC51887
0.8194	Intermediate Similarity	NPC117836
0.8194	Intermediate Similarity	NPC189650
0.8194	Intermediate Similarity	NPC89664
0.8194	Intermediate Similarity	NPC476178
0.8194	Intermediate Similarity	NPC113089
0.8194	Intermediate Similarity	NPC274085
0.8194	Intermediate Similarity	NPC475705
0.8188	Intermediate Similarity	NPC57211
0.8188	Intermediate Similarity	NPC472408
0.8188	Intermediate Similarity	NPC101294
0.8188	Intermediate Similarity	NPC250557
0.8188	Intermediate Similarity	NPC471981
0.8188	Intermediate Similarity	NPC128961
0.8188	Intermediate Similarity	NPC473655
0.8188	Intermediate Similarity	NPC470406
0.8188	Intermediate Similarity	NPC280937
0.8182	Intermediate Similarity	NPC49108
0.8182	Intermediate Similarity	NPC69755
0.8182	Intermediate Similarity	NPC329493
0.8182	Intermediate Similarity	NPC24075
0.8176	Intermediate Similarity	NPC45291
0.8176	Intermediate Similarity	NPC19980
0.8176	Intermediate Similarity	NPC279061
0.8175	Intermediate Similarity	NPC85342
0.8175	Intermediate Similarity	NPC205360
0.8169	Intermediate Similarity	NPC109007
0.8169	Intermediate Similarity	NPC283429
0.8169	Intermediate Similarity	NPC295384

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 NPC474340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	460
0.1-0.2	1005
0.2-0.3	1458
0.3-0.4	2730
0.4-0.5	1838
0.5-0.6	1108
0.6-0.7	417
0.7-0.8	123
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8613	High Similarity	NPD2935	Discontinued
0.8485	Intermediate Similarity	NPD2798	Approved
0.8385	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD2796	Approved
0.8321	Intermediate Similarity	NPD3972	Approved
0.8286	Intermediate Similarity	NPD2346	Discontinued
0.8235	Intermediate Similarity	NPD2313	Discontinued
0.8143	Intermediate Similarity	NPD1510	Phase 2
0.8143	Intermediate Similarity	NPD2799	Discontinued
0.8088	Intermediate Similarity	NPD6832	Phase 2
0.8058	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1651	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD6844	Discontinued
0.7947	Intermediate Similarity	NPD2801	Approved
0.7926	Intermediate Similarity	NPD1876	Approved
0.7922	Intermediate Similarity	NPD5494	Approved
0.7891	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1240	Approved
0.7857	Intermediate Similarity	NPD4307	Phase 2
0.7829	Intermediate Similarity	NPD1241	Discontinued
0.78	Intermediate Similarity	NPD3226	Approved
0.7778	Intermediate Similarity	NPD2344	Approved
0.7778	Intermediate Similarity	NPD5402	Approved
0.7748	Intermediate Similarity	NPD4380	Phase 2
0.773	Intermediate Similarity	NPD2979	Phase 3
0.7727	Intermediate Similarity	NPD5536	Phase 2
0.7724	Intermediate Similarity	NPD1549	Phase 2
0.7712	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7819	Suspended
0.7704	Intermediate Similarity	NPD1281	Approved
0.7671	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD3817	Phase 2
0.7655	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1471	Phase 3
0.7655	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1934	Approved
0.7639	Intermediate Similarity	NPD3748	Approved
0.7639	Intermediate Similarity	NPD4308	Phase 3
0.7632	Intermediate Similarity	NPD6599	Discontinued
0.7619	Intermediate Similarity	NPD7003	Approved
0.7612	Intermediate Similarity	NPD5691	Approved
0.7609	Intermediate Similarity	NPD1470	Approved
0.7584	Intermediate Similarity	NPD1511	Approved
0.7584	Intermediate Similarity	NPD6799	Approved
0.7568	Intermediate Similarity	NPD2309	Approved
0.7566	Intermediate Similarity	NPD7458	Discontinued
0.7554	Intermediate Similarity	NPD1019	Discontinued
0.7552	Intermediate Similarity	NPD1933	Approved
0.755	Intermediate Similarity	NPD920	Approved
0.7536	Intermediate Similarity	NPD1283	Approved
0.7533	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6232	Discontinued
0.7484	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1512	Approved
0.7482	Intermediate Similarity	NPD3266	Approved
0.7482	Intermediate Similarity	NPD3267	Approved
0.7482	Intermediate Similarity	NPD1203	Approved
0.7468	Intermediate Similarity	NPD7411	Suspended
0.7466	Intermediate Similarity	NPD1551	Phase 2
0.7465	Intermediate Similarity	NPD411	Approved
0.7453	Intermediate Similarity	NPD7473	Discontinued
0.7452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD1201	Approved
0.7431	Intermediate Similarity	NPD447	Suspended
0.7426	Intermediate Similarity	NPD4626	Approved
0.7421	Intermediate Similarity	NPD6959	Discontinued
0.7419	Intermediate Similarity	NPD6279	Approved
0.7419	Intermediate Similarity	NPD6801	Discontinued
0.7419	Intermediate Similarity	NPD6280	Approved
0.7417	Intermediate Similarity	NPD2532	Approved
0.7417	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2534	Approved
0.7417	Intermediate Similarity	NPD2533	Approved
0.7415	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3818	Discontinued
0.7397	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD9717	Approved
0.7383	Intermediate Similarity	NPD3750	Approved
0.7372	Intermediate Similarity	NPD3496	Discontinued
0.7368	Intermediate Similarity	NPD6273	Approved
0.7365	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2797	Approved
0.7347	Intermediate Similarity	NPD2531	Phase 2
0.7347	Intermediate Similarity	NPD2438	Suspended
0.7343	Intermediate Similarity	NPD3268	Approved
0.7343	Intermediate Similarity	NPD6798	Discontinued
0.7342	Intermediate Similarity	NPD7075	Discontinued
0.7338	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6559	Discontinued
0.7325	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5403	Approved
0.732	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1611	Approved
0.7315	Intermediate Similarity	NPD1243	Approved
0.7303	Intermediate Similarity	NPD4662	Approved
0.7303	Intermediate Similarity	NPD5401	Approved
0.7303	Intermediate Similarity	NPD4661	Approved
0.7293	Intermediate Similarity	NPD5283	Phase 1
0.7292	Intermediate Similarity	NPD6233	Phase 2
0.7285	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6166	Phase 2
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7259	Intermediate Similarity	NPD9493	Approved
0.7259	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5844	Phase 1
0.7254	Intermediate Similarity	NPD9494	Approved
0.7244	Intermediate Similarity	NPD5890	Approved
0.7244	Intermediate Similarity	NPD5889	Approved
0.7241	Intermediate Similarity	NPD3140	Approved
0.7241	Intermediate Similarity	NPD943	Approved
0.7241	Intermediate Similarity	NPD3142	Approved
0.723	Intermediate Similarity	NPD5406	Approved
0.723	Intermediate Similarity	NPD5408	Approved
0.723	Intermediate Similarity	NPD5405	Approved
0.723	Intermediate Similarity	NPD5404	Approved
0.7226	Intermediate Similarity	NPD5585	Approved
0.7222	Intermediate Similarity	NPD3926	Phase 2
0.7219	Intermediate Similarity	NPD3887	Approved
0.7218	Intermediate Similarity	NPD5535	Approved
0.7215	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4622	Approved
0.7192	Intermediate Similarity	NPD4618	Approved
0.7192	Intermediate Similarity	NPD6355	Discontinued
0.719	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD919	Approved
0.7186	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD17	Approved
0.7174	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD8032	Phase 2
0.717	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6808	Phase 2
0.7154	Intermediate Similarity	NPD3134	Approved
0.7152	Intermediate Similarity	NPD7054	Approved
0.7151	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7134	Intermediate Similarity	NPD6386	Approved
0.7134	Intermediate Similarity	NPD6385	Approved
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7124	Intermediate Similarity	NPD7390	Discontinued
0.7122	Intermediate Similarity	NPD3847	Discontinued
0.7121	Intermediate Similarity	NPD5451	Approved
0.7108	Intermediate Similarity	NPD7472	Approved
0.7108	Intermediate Similarity	NPD7074	Phase 3
0.7103	Intermediate Similarity	NPD3764	Approved
0.7103	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1358	Approved
0.7095	Intermediate Similarity	NPD5689	Approved
0.7095	Intermediate Similarity	NPD5688	Approved
0.7086	Intermediate Similarity	NPD2654	Approved
0.7073	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1535	Discovery
0.707	Intermediate Similarity	NPD6585	Discontinued
0.7067	Intermediate Similarity	NPD2353	Approved
0.7067	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6797	Phase 2
0.7059	Intermediate Similarity	NPD7440	Discontinued
0.7059	Intermediate Similarity	NPD6671	Approved
0.705	Intermediate Similarity	NPD1778	Approved
0.7048	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7033	Discontinued
0.7041	Intermediate Similarity	NPD8313	Approved
0.7041	Intermediate Similarity	NPD8312	Approved
0.7029	Intermediate Similarity	NPD1894	Discontinued
0.7024	Intermediate Similarity	NPD7251	Discontinued
0.7021	Intermediate Similarity	NPD1608	Approved
0.7019	Intermediate Similarity	NPD3749	Approved
0.7013	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2651	Approved
0.7006	Intermediate Similarity	NPD2649	Approved
0.7	Intermediate Similarity	NPD2296	Approved
0.7	Intermediate Similarity	NPD5977	Approved
0.7	Intermediate Similarity	NPD4477	Approved
0.7	Intermediate Similarity	NPD4476	Approved
0.7	Intermediate Similarity	NPD5978	Approved
0.6993	Remote Similarity	NPD1164	Approved
0.6982	Remote Similarity	NPD7808	Phase 3
0.6978	Remote Similarity	NPD3025	Approved
0.6978	Remote Similarity	NPD3024	Approved
0.6974	Remote Similarity	NPD2800	Approved
0.6972	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4359	Approved
0.6968	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6287	Discontinued
0.6943	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9261	Approved
0.6923	Remote Similarity	NPD5049	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data