NPASS Compound

Structure

NPC469575 OpenBabel07101718272D 24 27 0 0 1 0 0 0 0 0999 V2000 -0.0000 -4.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 -4.1369 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 3 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 0.0000 -0.0000 0.0000 C 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 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 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 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 8 2 0 0 0 0 2 11 1 0 0 0 0 3 8 1 0 0 0 0 3 15 2 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 7 24 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 12 1 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.07
Volume:	311.439
LogP:	2.81
LogD:	2.766
LogS:	-4.26
# Rotatable Bonds:	2
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.871
Synthetic Accessibility Score:	3.125
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.872
MDCK Permeability:	2.487856909283437e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	98.84293365478516%
Volume Distribution (VD):	0.647
Pgp-substrate:	1.8293884992599487%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.745
CYP2C19-inhibitor:	0.916
CYP2C19-substrate:	0.166
CYP2C9-inhibitor:	0.781
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.947
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.319

ADMET: Excretion

Clearance (CL):	15.704
Half-life (T1/2):	0.341

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.598
AMES Toxicity:	0.3
Rat Oral Acute Toxicity:	0.386
Maximum Recommended Daily Dose:	0.838
Skin Sensitization:	0.653
Carcinogencity:	0.732
Eye Corrosion:	0.003
Eye Irritation:	0.409
Respiratory Toxicity:	0.336

Download Data

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

Natural Product: NPC469575

Natural Product ID:	NPC469575
*Common Name:**	(3R,3S)-Onogenin
IUPAC Name:	5,7-dihydroxy-3-(6-methoxy-1,3-benzodioxol-5-yl)-2,3-dihydrochromen-4-one
Synonyms:	(3R,3S)-Onogenin
Standard InCHIKey:	MNXNLFUKHPLPES-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-21-12-5-14-13(23-7-24-14)4-9(12)10-6-22-15-3-8(18)2-11(19)16(15)17(10)20/h2-5,10,18-19H,6-7H2,1H3
SMILES:	COC1=CC2=C(C=C1C3COC4=CC(=CC(=C4C3=O)O)O)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088034
PubChem CID:	46881084
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002604] 2'-O-methylated isoflavonoids

*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
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO14114	Dalbergia parviflora	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	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	5.6	uM	PMID[479116]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	1.9	uM	PMID[479116]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[479116]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	8.1	uM	PMID[479116]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	1.0	uM	PMID[479116]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	9.4	uM	PMID[479116]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	4.2	uM	PMID[479116]

☑ 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 NPC469575 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	398
0.1-0.2	1761
0.2-0.3	4041
0.3-0.4	9861
0.4-0.5	8485
0.5-0.6	3529
0.6-0.7	4877
0.7-0.8	5949
0.8-0.85	2856
0.85-0.9	849
0.9-0.95	89
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9563	High Similarity	NPC223375
0.9563	High Similarity	NPC475825
0.9554	High Similarity	NPC470178
0.9484	High Similarity	NPC167595
0.9484	High Similarity	NPC258644
0.9427	High Similarity	NPC162668
0.9423	High Similarity	NPC215375
0.9423	High Similarity	NPC62518
0.9375	High Similarity	NPC42892
0.9367	High Similarity	NPC478199
0.9359	High Similarity	NPC181960
0.9359	High Similarity	NPC469584
0.9355	High Similarity	NPC472909
0.9313	High Similarity	NPC113093
0.9308	High Similarity	NPC273959
0.9304	High Similarity	NPC295009
0.9304	High Similarity	NPC260640
0.929	High Similarity	NPC244371
0.9286	High Similarity	NPC117579
0.9245	High Similarity	NPC125991
0.9241	High Similarity	NPC285973
0.9241	High Similarity	NPC225624
0.9236	High Similarity	NPC222814
0.9236	High Similarity	NPC472910
0.9236	High Similarity	NPC472911
0.9236	High Similarity	NPC96167
0.9236	High Similarity	NPC472914
0.9236	High Similarity	NPC472913
0.9236	High Similarity	NPC245758
0.9231	High Similarity	NPC18954
0.9231	High Similarity	NPC31018
0.9231	High Similarity	NPC255807
0.9231	High Similarity	NPC37392
0.9226	High Similarity	NPC292460
0.9221	High Similarity	NPC179183
0.9198	High Similarity	NPC472381
0.9198	High Similarity	NPC472383
0.9187	High Similarity	NPC475985
0.9172	High Similarity	NPC235165
0.9172	High Similarity	NPC255106
0.9167	High Similarity	NPC472915
0.9167	High Similarity	NPC280937
0.9161	High Similarity	NPC149614
0.9152	High Similarity	NPC156635
0.9141	High Similarity	NPC183357
0.9141	High Similarity	NPC22195
0.9141	High Similarity	NPC21190
0.9141	High Similarity	NPC224462
0.9141	High Similarity	NPC105511
0.9141	High Similarity	NPC44558
0.9141	High Similarity	NPC212748
0.9136	High Similarity	NPC93099
0.9136	High Similarity	NPC76482
0.913	High Similarity	NPC326520
0.9119	High Similarity	NPC475886
0.9119	High Similarity	NPC269906
0.9119	High Similarity	NPC474287
0.9114	High Similarity	NPC129684
0.9114	High Similarity	NPC165977
0.9114	High Similarity	NPC99597
0.9114	High Similarity	NPC241904
0.9114	High Similarity	NPC162869
0.9114	High Similarity	NPC210084
0.9114	High Similarity	NPC475267
0.9114	High Similarity	NPC300727
0.9114	High Similarity	NPC217677
0.9114	High Similarity	NPC299520
0.9114	High Similarity	NPC48208
0.9114	High Similarity	NPC474990
0.9114	High Similarity	NPC474208
0.9114	High Similarity	NPC474836
0.9114	High Similarity	NPC156057
0.9108	High Similarity	NPC2928
0.9103	High Similarity	NPC199100
0.9103	High Similarity	NPC148497
0.9103	High Similarity	NPC101996
0.9103	High Similarity	NPC180234
0.9103	High Similarity	NPC120537
0.9103	High Similarity	NPC104728
0.9103	High Similarity	NPC35544
0.9103	High Similarity	NPC153008
0.9103	High Similarity	NPC260979
0.9097	High Similarity	NPC306821
0.9097	High Similarity	NPC338131
0.9097	High Similarity	NPC234152
0.9091	High Similarity	NPC236327
0.9091	High Similarity	NPC472607
0.9091	High Similarity	NPC290304
0.9085	High Similarity	NPC307518
0.9085	High Similarity	NPC260263
0.9085	High Similarity	NPC267254
0.9085	High Similarity	NPC48773
0.9085	High Similarity	NPC205076
0.9085	High Similarity	NPC472386
0.908	High Similarity	NPC201292
0.908	High Similarity	NPC95855
0.908	High Similarity	NPC471457
0.908	High Similarity	NPC226294
0.908	High Similarity	NPC186807
0.908	High Similarity	NPC170675
0.908	High Similarity	NPC93337
0.908	High Similarity	NPC45638
0.908	High Similarity	NPC105025
0.908	High Similarity	NPC469931
0.908	High Similarity	NPC183036
0.908	High Similarity	NPC112755
0.908	High Similarity	NPC211309
0.908	High Similarity	NPC58053
0.908	High Similarity	NPC475942
0.908	High Similarity	NPC471287
0.908	High Similarity	NPC210042
0.9074	High Similarity	NPC128293
0.9074	High Similarity	NPC170245
0.9068	High Similarity	NPC110257
0.9068	High Similarity	NPC94777
0.9062	High Similarity	NPC266314
0.9062	High Similarity	NPC474351
0.9062	High Similarity	NPC475883
0.9062	High Similarity	NPC470756
0.9062	High Similarity	NPC474187
0.9062	High Similarity	NPC474186
0.9062	High Similarity	NPC94155
0.9057	High Similarity	NPC476242
0.9057	High Similarity	NPC152904
0.9051	High Similarity	NPC45131
0.9051	High Similarity	NPC155063
0.9051	High Similarity	NPC274730
0.9051	High Similarity	NPC472916
0.9045	High Similarity	NPC88645
0.9045	High Similarity	NPC292214
0.9045	High Similarity	NPC271779
0.9045	High Similarity	NPC167091
0.9045	High Similarity	NPC57211
0.9045	High Similarity	NPC478213
0.9045	High Similarity	NPC206238
0.9045	High Similarity	NPC469550
0.9038	High Similarity	NPC171010
0.9038	High Similarity	NPC208043
0.9038	High Similarity	NPC226973
0.9038	High Similarity	NPC279061
0.9036	High Similarity	NPC257714
0.9032	High Similarity	NPC238366
0.9032	High Similarity	NPC328119
0.903	High Similarity	NPC239549
0.903	High Similarity	NPC51774
0.903	High Similarity	NPC236191
0.9024	High Similarity	NPC471416
0.9024	High Similarity	NPC34287
0.9024	High Similarity	NPC474434
0.902	High Similarity	NPC472917
0.9018	High Similarity	NPC471288
0.9018	High Similarity	NPC146792
0.9018	High Similarity	NPC135345
0.9018	High Similarity	NPC58716
0.9018	High Similarity	NPC45618
0.9012	High Similarity	NPC475738
0.9012	High Similarity	NPC25361
0.9012	High Similarity	NPC165720
0.9006	High Similarity	NPC127782
0.9006	High Similarity	NPC300537
0.9006	High Similarity	NPC81679
0.9	High Similarity	NPC228785
0.9	High Similarity	NPC263449
0.9	High Similarity	NPC14353
0.9	High Similarity	NPC56085
0.8994	High Similarity	NPC36852
0.8994	High Similarity	NPC78225
0.8994	High Similarity	NPC220462
0.8994	High Similarity	NPC223787
0.8994	High Similarity	NPC262286
0.8994	High Similarity	NPC108456
0.8987	High Similarity	NPC478238
0.8987	High Similarity	NPC213622
0.8982	High Similarity	NPC67302
0.8981	High Similarity	NPC239128
0.8981	High Similarity	NPC187498
0.8981	High Similarity	NPC219582
0.8981	High Similarity	NPC71334
0.8981	High Similarity	NPC52623
0.8981	High Similarity	NPC156222
0.8981	High Similarity	NPC301123
0.8981	High Similarity	NPC275836
0.8981	High Similarity	NPC188203
0.8981	High Similarity	NPC57030
0.8981	High Similarity	NPC301323
0.8981	High Similarity	NPC302950
0.8981	High Similarity	NPC83508
0.8981	High Similarity	NPC68882
0.8981	High Similarity	NPC293183
0.8981	High Similarity	NPC198826
0.8981	High Similarity	NPC161277
0.8981	High Similarity	NPC39007
0.8981	High Similarity	NPC100887
0.8981	High Similarity	NPC120163
0.8981	High Similarity	NPC212678
0.8981	High Similarity	NPC162313
0.8981	High Similarity	NPC256283
0.8981	High Similarity	NPC131624
0.8981	High Similarity	NPC222830
0.8981	High Similarity	NPC236637

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 NPC469575 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	944
0.2-0.3	1895
0.3-0.4	2639
0.4-0.5	1807
0.5-0.6	946
0.6-0.7	379
0.7-0.8	136
0.8-0.85	36
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9018	High Similarity	NPD3818	Discontinued
0.8981	High Similarity	NPD1934	Approved
0.8924	High Similarity	NPD2801	Approved
0.8882	High Similarity	NPD5494	Approved
0.8795	High Similarity	NPD7074	Phase 3
0.875	High Similarity	NPD4338	Clinical (unspecified phase)
0.8735	High Similarity	NPD7054	Approved
0.8696	High Similarity	NPD3882	Suspended
0.8688	High Similarity	NPD2393	Clinical (unspecified phase)
0.8683	High Similarity	NPD7472	Approved
0.8529	High Similarity	NPD7808	Phase 3
0.8528	High Similarity	NPD4381	Clinical (unspecified phase)
0.8521	High Similarity	NPD6797	Phase 2
0.8471	Intermediate Similarity	NPD1511	Approved
0.8471	Intermediate Similarity	NPD7251	Discontinued
0.8443	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6166	Phase 2
0.8405	Intermediate Similarity	NPD3817	Phase 2
0.8365	Intermediate Similarity	NPD1512	Approved
0.8354	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7473	Discontinued
0.8269	Intermediate Similarity	NPD1549	Phase 2
0.8256	Intermediate Similarity	NPD6559	Discontinued
0.8214	Intermediate Similarity	NPD6232	Discontinued
0.8199	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD5844	Phase 1
0.8187	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD37	Approved
0.8155	Intermediate Similarity	NPD1247	Approved
0.8155	Intermediate Similarity	NPD7199	Phase 2
0.8144	Intermediate Similarity	NPD6234	Discontinued
0.8133	Intermediate Similarity	NPD4967	Phase 2
0.8133	Intermediate Similarity	NPD4965	Approved
0.8133	Intermediate Similarity	NPD4966	Approved
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD1465	Phase 2
0.8084	Intermediate Similarity	NPD7075	Discontinued
0.8077	Intermediate Similarity	NPD1510	Phase 2
0.8072	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4380	Phase 2
0.8038	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2800	Approved
0.7976	Intermediate Similarity	NPD3749	Approved
0.7963	Intermediate Similarity	NPD2533	Approved
0.7963	Intermediate Similarity	NPD2532	Approved
0.7963	Intermediate Similarity	NPD2534	Approved
0.7953	Intermediate Similarity	NPD3926	Phase 2
0.7941	Intermediate Similarity	NPD6959	Discontinued
0.7935	Intermediate Similarity	NPD1240	Approved
0.7929	Intermediate Similarity	NPD919	Approved
0.7919	Intermediate Similarity	NPD7228	Approved
0.7911	Intermediate Similarity	NPD2796	Approved
0.7901	Intermediate Similarity	NPD6799	Approved
0.7892	Intermediate Similarity	NPD7411	Suspended
0.7886	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5402	Approved
0.7834	Intermediate Similarity	NPD1607	Approved
0.7831	Intermediate Similarity	NPD6599	Discontinued
0.7816	Intermediate Similarity	NPD3751	Discontinued
0.7771	Intermediate Similarity	NPD1933	Approved
0.7747	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6801	Discontinued
0.7735	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3750	Approved
0.7711	Intermediate Similarity	NPD1653	Approved
0.7707	Intermediate Similarity	NPD943	Approved
0.7701	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2935	Discontinued
0.7688	Intermediate Similarity	NPD3787	Discontinued
0.7658	Intermediate Similarity	NPD230	Phase 1
0.7658	Intermediate Similarity	NPD447	Suspended
0.7651	Intermediate Similarity	NPD920	Approved
0.764	Intermediate Similarity	NPD2344	Approved
0.764	Intermediate Similarity	NPD7685	Pre-registration
0.7613	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7768	Phase 2
0.7595	Intermediate Similarity	NPD1613	Approved
0.7595	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7578	Intermediate Similarity	NPD6099	Approved
0.7578	Intermediate Similarity	NPD6100	Approved
0.7564	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8312	Approved
0.7556	Intermediate Similarity	NPD8313	Approved
0.7546	Intermediate Similarity	NPD1243	Approved
0.7542	Intermediate Similarity	NPD7240	Approved
0.753	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5711	Approved
0.7486	Intermediate Similarity	NPD5710	Approved
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6780	Approved
0.746	Intermediate Similarity	NPD6779	Approved
0.746	Intermediate Similarity	NPD6782	Approved
0.746	Intermediate Similarity	NPD6776	Approved
0.746	Intermediate Similarity	NPD6781	Approved
0.746	Intermediate Similarity	NPD6778	Approved
0.746	Intermediate Similarity	NPD6777	Approved
0.746	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3226	Approved
0.7455	Intermediate Similarity	NPD2309	Approved
0.744	Intermediate Similarity	NPD5403	Approved
0.7439	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5401	Approved
0.7423	Intermediate Similarity	NPD2346	Discontinued
0.741	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7407	Intermediate Similarity	NPD3748	Approved
0.7394	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7353	Intermediate Similarity	NPD7458	Discontinued
0.7344	Intermediate Similarity	NPD7697	Approved
0.7344	Intermediate Similarity	NPD7698	Approved
0.7344	Intermediate Similarity	NPD7435	Discontinued
0.7344	Intermediate Similarity	NPD7696	Phase 3
0.7342	Intermediate Similarity	NPD4908	Phase 1
0.7338	Intermediate Similarity	NPD1610	Phase 2
0.7337	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD8151	Discontinued
0.7325	Intermediate Similarity	NPD2798	Approved
0.7322	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7871	Phase 2
0.7306	Intermediate Similarity	NPD7870	Phase 2
0.7303	Intermediate Similarity	NPD2403	Approved
0.7301	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3027	Phase 3
0.7293	Intermediate Similarity	NPD5953	Discontinued
0.7292	Intermediate Similarity	NPD5006	Approved
0.7292	Intermediate Similarity	NPD5005	Approved
0.7288	Intermediate Similarity	NPD7229	Phase 3
0.7284	Intermediate Similarity	NPD6651	Approved
0.7278	Intermediate Similarity	NPD7286	Phase 2
0.7278	Intermediate Similarity	NPD2861	Phase 2
0.7259	Intermediate Similarity	NPD7783	Phase 2
0.7259	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2313	Discontinued
0.7247	Intermediate Similarity	NPD5242	Approved
0.7241	Intermediate Similarity	NPD5353	Approved
0.7202	Intermediate Similarity	NPD6823	Phase 2
0.7196	Intermediate Similarity	NPD6535	Approved
0.7196	Intermediate Similarity	NPD6534	Approved
0.7194	Intermediate Similarity	NPD7701	Phase 2
0.7179	Intermediate Similarity	NPD1608	Approved
0.7173	Intermediate Similarity	NPD4420	Approved
0.7172	Intermediate Similarity	NPD7801	Approved
0.717	Intermediate Similarity	NPD9494	Approved
0.716	Intermediate Similarity	NPD7390	Discontinued
0.7152	Intermediate Similarity	NPD1203	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD3268	Approved
0.7135	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6674	Discontinued
0.7121	Intermediate Similarity	NPD7874	Approved
0.7121	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7549	Discontinued
0.7117	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3705	Approved
0.7115	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7028	Phase 2
0.7108	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4363	Phase 3
0.7105	Intermediate Similarity	NPD4360	Phase 2
0.7091	Intermediate Similarity	NPD7033	Discontinued
0.7086	Intermediate Similarity	NPD8455	Phase 2
0.7083	Intermediate Similarity	NPD7700	Phase 2
0.7083	Intermediate Similarity	NPD7699	Phase 2
0.7074	Intermediate Similarity	NPD4287	Approved
0.7069	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4361	Phase 2
0.7068	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8150	Discontinued
0.7044	Intermediate Similarity	NPD2797	Approved
0.7037	Intermediate Similarity	NPD3764	Approved
0.7029	Intermediate Similarity	NPD6844	Discontinued
0.7025	Intermediate Similarity	NPD4749	Approved
0.7024	Intermediate Similarity	NPD2654	Approved
0.7019	Intermediate Similarity	NPD6832	Phase 2
0.7018	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD7266	Discontinued
0.7006	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7680	Approved
0.6987	Remote Similarity	NPD17	Approved
0.6982	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4110	Phase 3
0.6971	Remote Similarity	NPD6386	Approved

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