NPASS Compound

Structure

NPC476459 OpenBabel07101718192D 26 30 0 0 1 0 0 0 0 0999 V2000 5.0995 0.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3255 0.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2096 -0.6568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9890 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1915 0.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1050 0.3377 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1231 -1.0636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5118 1.2512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 1.7226 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 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 12 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 15 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 13 1 0 0 0 0 7 17 2 0 0 0 0 8 24 1 0 0 0 0 9 20 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 12 16 2 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 8 1 1 0 0 0 14 19 1 0 0 0 0 15 25 1 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 12 1 1 0 0 0 19 26 1 0 0 0 0 20 1 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.11
Volume:	345.98
LogP:	2.845
LogD:	2.746
LogS:	-4.047
# Rotatable Bonds:	2
TPSA:	92.29
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	4.066
Fsp3:	0.3
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:	-5.003
MDCK Permeability:	8.955026714829728e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	95.7960433959961%
Volume Distribution (VD):	0.888
Pgp-substrate:	8.427587509155273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.926
CYP1A2-substrate:	0.884
CYP2C19-inhibitor:	0.201
CYP2C19-substrate:	0.489
CYP2C9-inhibitor:	0.668
CYP2C9-substrate:	0.726
CYP2D6-inhibitor:	0.229
CYP2D6-substrate:	0.246
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.656

ADMET: Excretion

Clearance (CL):	11.454
Half-life (T1/2):	0.257

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.866
Drug-inuced Liver Injury (DILI):	0.772
AMES Toxicity:	0.841
Rat Oral Acute Toxicity:	0.637
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.263
Carcinogencity:	0.768
Eye Corrosion:	0.003
Eye Irritation:	0.081
Respiratory Toxicity:	0.056

Download Data

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

Natural Product: NPC476459

Natural Product ID:	NPC476459
*Common Name:**	JDKOSPKTKADBCU-GKCIPKSASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JDKOSPKTKADBCU-GKCIPKSASA-N
Standard InCHI:	InChI=1S/C20H18O6/c1-20(23,9-21)17-7-13-15(25-17)5-4-11-14-8-24-16-6-10(22)2-3-12(16)19(14)26-18(11)13/h2-7,14,19,21-23H,8-9H2,1H3/t14-,19-,20-/m0/s1
SMILES:	CC(CO)(C1=CC2=C(O1)C=CC3=C2OC4C3COC5=C4C=CC(=C5)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL7054
PubChem CID:	44264369
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662101]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15013012]
NPO10262	Crotalaria assamica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15013012]
NPO10262	Crotalaria assamica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10262	Crotalaria assamica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10262	Crotalaria assamica	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
IC50	6

Activity Type	# Activity
Individual Protein	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3102	Individual Protein	Beta-glucuronidase	Rattus norvegicus	IC50	>	30000.0	nM	PMID[545038]
NPT3103	Individual Protein	Lysozyme C	Rattus norvegicus	IC50	>	30000.0	nM	PMID[545038]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	>	30000.0	nM	PMID[545038]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	30000.0	nM	PMID[545038]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	13900.0	nM	PMID[545038]

☑ 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 NPC476459 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	411
0.1-0.2	1601
0.2-0.3	3552
0.3-0.4	8954
0.4-0.5	9687
0.5-0.6	4165
0.6-0.7	5629
0.7-0.8	4930
0.8-0.85	2726
0.85-0.9	940
0.9-0.95	101
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC472581
0.9554	High Similarity	NPC40583
0.9448	High Similarity	NPC472584
0.9437	High Similarity	NPC109180
0.9434	High Similarity	NPC74854
0.9434	High Similarity	NPC30655
0.9434	High Similarity	NPC45124
0.9387	High Similarity	NPC120220
0.9375	High Similarity	NPC219861
0.9371	High Similarity	NPC220582
0.9371	High Similarity	NPC304839
0.9321	High Similarity	NPC53640
0.9299	High Similarity	NPC1477
0.9299	High Similarity	NPC213608
0.9245	High Similarity	NPC65504
0.9236	High Similarity	NPC473996
0.9236	High Similarity	NPC217149
0.9236	High Similarity	NPC210597
0.9236	High Similarity	NPC5871
0.9236	High Similarity	NPC243171
0.9236	High Similarity	NPC171651
0.9236	High Similarity	NPC216035
0.9236	High Similarity	NPC35567
0.9182	High Similarity	NPC10754
0.9182	High Similarity	NPC20530
0.9182	High Similarity	NPC215917
0.9177	High Similarity	NPC209760
0.9177	High Similarity	NPC293286
0.9177	High Similarity	NPC100134
0.9172	High Similarity	NPC254412
0.9172	High Similarity	NPC471229
0.9172	High Similarity	NPC472422
0.9172	High Similarity	NPC472580
0.9172	High Similarity	NPC474772
0.9172	High Similarity	NPC262039
0.9172	High Similarity	NPC244577
0.9172	High Similarity	NPC472423
0.9172	High Similarity	NPC262038
0.9172	High Similarity	NPC319910
0.9172	High Similarity	NPC471676
0.9172	High Similarity	NPC472636
0.9172	High Similarity	NPC474744
0.9172	High Similarity	NPC472420
0.9172	High Similarity	NPC263384
0.9172	High Similarity	NPC278476
0.9141	High Similarity	NPC259007
0.9141	High Similarity	NPC329215
0.9141	High Similarity	NPC204088
0.9119	High Similarity	NPC48579
0.9119	High Similarity	NPC471116
0.9119	High Similarity	NPC259710
0.9119	High Similarity	NPC476169
0.9119	High Similarity	NPC217706
0.9119	High Similarity	NPC207809
0.9119	High Similarity	NPC304207
0.9114	High Similarity	NPC285623
0.9114	High Similarity	NPC31627
0.9114	High Similarity	NPC476238
0.9114	High Similarity	NPC138288
0.9114	High Similarity	NPC477957
0.9114	High Similarity	NPC327269
0.9108	High Similarity	NPC105136
0.9108	High Similarity	NPC472421
0.9108	High Similarity	NPC267117
0.9091	High Similarity	NPC53252
0.9085	High Similarity	NPC82330
0.9085	High Similarity	NPC119589
0.9085	High Similarity	NPC323137
0.908	High Similarity	NPC471286
0.9074	High Similarity	NPC92589
0.9068	High Similarity	NPC476349
0.9068	High Similarity	NPC476350
0.9057	High Similarity	NPC223701
0.9057	High Similarity	NPC7989
0.9057	High Similarity	NPC248793
0.9057	High Similarity	NPC180301
0.9057	High Similarity	NPC244250
0.9057	High Similarity	NPC472583
0.9057	High Similarity	NPC469405
0.9057	High Similarity	NPC122365
0.9057	High Similarity	NPC20907
0.9057	High Similarity	NPC203080
0.9051	High Similarity	NPC471675
0.9051	High Similarity	NPC471677
0.9045	High Similarity	NPC296030
0.9045	High Similarity	NPC226644
0.9045	High Similarity	NPC37226
0.9045	High Similarity	NPC39929
0.9045	High Similarity	NPC277032
0.9036	High Similarity	NPC131866
0.9024	High Similarity	NPC300053
0.9012	High Similarity	NPC306978
0.9006	High Similarity	NPC260902
0.9006	High Similarity	NPC296957
0.9	High Similarity	NPC304745
0.9	High Similarity	NPC477958
0.9	High Similarity	NPC111341
0.8994	High Similarity	NPC475790
0.8987	High Similarity	NPC61258
0.8981	High Similarity	NPC39195
0.8981	High Similarity	NPC135325
0.897	High Similarity	NPC277480
0.8963	High Similarity	NPC124038
0.8963	High Similarity	NPC63438
0.8963	High Similarity	NPC472582
0.8944	High Similarity	NPC146636
0.8944	High Similarity	NPC247677
0.8944	High Similarity	NPC78492
0.8944	High Similarity	NPC208152
0.8944	High Similarity	NPC160015
0.8938	High Similarity	NPC268193
0.8938	High Similarity	NPC472462
0.8938	High Similarity	NPC236756
0.8938	High Similarity	NPC311579
0.8935	High Similarity	NPC324220
0.8935	High Similarity	NPC312630
0.8931	High Similarity	NPC474021
0.8931	High Similarity	NPC474023
0.8931	High Similarity	NPC170169
0.8929	High Similarity	NPC310794
0.8924	High Similarity	NPC221868
0.8924	High Similarity	NPC37208
0.8924	High Similarity	NPC89442
0.8924	High Similarity	NPC317492
0.8924	High Similarity	NPC472628
0.8922	High Similarity	NPC102277
0.8922	High Similarity	NPC279209
0.8917	High Similarity	NPC122828
0.8917	High Similarity	NPC12148
0.8917	High Similarity	NPC14875
0.8917	High Similarity	NPC176869
0.8917	High Similarity	NPC470670
0.8917	High Similarity	NPC40086
0.8917	High Similarity	NPC211466
0.8917	High Similarity	NPC473133
0.8917	High Similarity	NPC472627
0.8917	High Similarity	NPC3779
0.8917	High Similarity	NPC44721
0.8917	High Similarity	NPC130581
0.8917	High Similarity	NPC308200
0.8917	High Similarity	NPC472918
0.8917	High Similarity	NPC476182
0.8917	High Similarity	NPC47388
0.8916	High Similarity	NPC320789
0.8916	High Similarity	NPC247973
0.8909	High Similarity	NPC136641
0.8909	High Similarity	NPC37183
0.8896	High Similarity	NPC260296
0.8896	High Similarity	NPC471976
0.8896	High Similarity	NPC115432
0.8889	High Similarity	NPC268360
0.8889	High Similarity	NPC161650
0.8882	High Similarity	NPC477530
0.8882	High Similarity	NPC148938
0.8882	High Similarity	NPC470681
0.8882	High Similarity	NPC198490
0.8875	High Similarity	NPC56232
0.8875	High Similarity	NPC10807
0.8875	High Similarity	NPC244583
0.8875	High Similarity	NPC161881
0.8875	High Similarity	NPC150123
0.8869	High Similarity	NPC477529
0.8869	High Similarity	NPC121333
0.8868	High Similarity	NPC78335
0.8868	High Similarity	NPC230713
0.8868	High Similarity	NPC471115
0.8868	High Similarity	NPC29777
0.8862	High Similarity	NPC152477
0.8861	High Similarity	NPC272194
0.8861	High Similarity	NPC145467
0.8861	High Similarity	NPC168085
0.8855	High Similarity	NPC235610
0.8854	High Similarity	NPC316769
0.8854	High Similarity	NPC299011
0.8854	High Similarity	NPC51641
0.8854	High Similarity	NPC210826
0.8854	High Similarity	NPC229190
0.8854	High Similarity	NPC1940
0.8854	High Similarity	NPC477955
0.8854	High Similarity	NPC148011
0.8854	High Similarity	NPC300267
0.8854	High Similarity	NPC472629
0.8848	High Similarity	NPC155640
0.8848	High Similarity	NPC91288
0.8848	High Similarity	NPC38591
0.8841	High Similarity	NPC14822
0.8841	High Similarity	NPC472346
0.8841	High Similarity	NPC97812
0.8841	High Similarity	NPC3629
0.8834	High Similarity	NPC311574
0.8834	High Similarity	NPC264932
0.8834	High Similarity	NPC123544
0.8834	High Similarity	NPC22192
0.8834	High Similarity	NPC125969
0.8834	High Similarity	NPC244750
0.883	High Similarity	NPC104682
0.8827	High Similarity	NPC475797
0.8827	High Similarity	NPC164427
0.8827	High Similarity	NPC469936
0.8827	High Similarity	NPC129053

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 NPC476459 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	878
0.2-0.3	1681
0.3-0.4	2653
0.4-0.5	1979
0.5-0.6	1073
0.6-0.7	347
0.7-0.8	136
0.8-0.85	42
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8773	High Similarity	NPD7075	Discontinued
0.875	High Similarity	NPD4380	Phase 2
0.8704	High Similarity	NPD7096	Clinical (unspecified phase)
0.8671	High Similarity	NPD4378	Clinical (unspecified phase)
0.8596	High Similarity	NPD6559	Discontinued
0.8589	High Similarity	NPD2393	Clinical (unspecified phase)
0.8537	High Similarity	NPD8443	Clinical (unspecified phase)
0.8528	High Similarity	NPD6801	Discontinued
0.8485	Intermediate Similarity	NPD3882	Suspended
0.8462	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6166	Phase 2
0.8443	Intermediate Similarity	NPD5494	Approved
0.8434	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD3749	Approved
0.8421	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD1934	Approved
0.8408	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6799	Approved
0.8256	Intermediate Similarity	NPD3818	Discontinued
0.8242	Intermediate Similarity	NPD7411	Suspended
0.8182	Intermediate Similarity	NPD6599	Discontinued
0.8176	Intermediate Similarity	NPD6959	Discontinued
0.8165	Intermediate Similarity	NPD2796	Approved
0.8144	Intermediate Similarity	NPD2801	Approved
0.8144	Intermediate Similarity	NPD7819	Suspended
0.814	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2344	Approved
0.811	Intermediate Similarity	NPD920	Approved
0.8101	Intermediate Similarity	NPD1510	Phase 2
0.8081	Intermediate Similarity	NPD3926	Phase 2
0.807	Intermediate Similarity	NPD1247	Approved
0.8049	Intermediate Similarity	NPD1512	Approved
0.8047	Intermediate Similarity	NPD7768	Phase 2
0.8047	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2800	Approved
0.8011	Intermediate Similarity	NPD6797	Phase 2
0.8	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD5403	Approved
0.7989	Intermediate Similarity	NPD7473	Discontinued
0.7988	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5402	Approved
0.7988	Intermediate Similarity	NPD3817	Phase 2
0.7966	Intermediate Similarity	NPD7251	Discontinued
0.7962	Intermediate Similarity	NPD1240	Approved
0.7955	Intermediate Similarity	NPD7074	Phase 3
0.7953	Intermediate Similarity	NPD919	Approved
0.7944	Intermediate Similarity	NPD8434	Phase 2
0.7927	Intermediate Similarity	NPD1511	Approved
0.7921	Intermediate Similarity	NPD7808	Phase 3
0.7921	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6232	Discontinued
0.7914	Intermediate Similarity	NPD2309	Approved
0.791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD1243	Approved
0.7898	Intermediate Similarity	NPD7054	Approved
0.7879	Intermediate Similarity	NPD5401	Approved
0.7866	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1607	Approved
0.7853	Intermediate Similarity	NPD7472	Approved
0.7821	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2533	Approved
0.7771	Intermediate Similarity	NPD2532	Approved
0.7771	Intermediate Similarity	NPD2534	Approved
0.7744	Intermediate Similarity	NPD4628	Phase 3
0.774	Intermediate Similarity	NPD3751	Discontinued
0.7669	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2799	Discontinued
0.7636	Intermediate Similarity	NPD3750	Approved
0.7616	Intermediate Similarity	NPD5761	Phase 2
0.7616	Intermediate Similarity	NPD5760	Phase 2
0.7614	Intermediate Similarity	NPD3787	Discontinued
0.761	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8313	Approved
0.7582	Intermediate Similarity	NPD8312	Approved
0.7528	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD1465	Phase 2
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD4363	Phase 3
0.75	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.7473	Intermediate Similarity	NPD4287	Approved
0.7472	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7458	Intermediate Similarity	NPD7199	Phase 2
0.7456	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6234	Discontinued
0.743	Intermediate Similarity	NPD2403	Approved
0.7429	Intermediate Similarity	NPD4965	Approved
0.7429	Intermediate Similarity	NPD4966	Approved
0.7429	Intermediate Similarity	NPD4967	Phase 2
0.7425	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6651	Approved
0.7416	Intermediate Similarity	NPD7229	Phase 3
0.741	Intermediate Similarity	NPD2424	Discontinued
0.7394	Intermediate Similarity	NPD6099	Approved
0.7394	Intermediate Similarity	NPD6100	Approved
0.7391	Intermediate Similarity	NPD2313	Discontinued
0.7391	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3226	Approved
0.7371	Intermediate Similarity	NPD7435	Discontinued
0.7371	Intermediate Similarity	NPD2296	Approved
0.7368	Intermediate Similarity	NPD4361	Phase 2
0.7368	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6355	Discontinued
0.7349	Intermediate Similarity	NPD1471	Phase 3
0.7349	Intermediate Similarity	NPD2346	Discontinued
0.7348	Intermediate Similarity	NPD7228	Approved
0.7347	Intermediate Similarity	NPD7584	Approved
0.7345	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7870	Phase 2
0.7333	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD7033	Discontinued
0.7333	Intermediate Similarity	NPD7871	Phase 2
0.7333	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5711	Approved
0.7318	Intermediate Similarity	NPD5710	Approved
0.7314	Intermediate Similarity	NPD8455	Phase 2
0.7301	Intermediate Similarity	NPD943	Approved
0.7301	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1613	Approved
0.7299	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7390	Discontinued
0.7287	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6798	Discontinued
0.7282	Intermediate Similarity	NPD7697	Approved
0.7282	Intermediate Similarity	NPD7696	Phase 3
0.7282	Intermediate Similarity	NPD7698	Approved
0.7273	Intermediate Similarity	NPD8151	Discontinued
0.7267	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1610	Phase 2
0.7261	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6279	Approved
0.7257	Intermediate Similarity	NPD6280	Approved
0.7257	Intermediate Similarity	NPD37	Approved
0.7256	Intermediate Similarity	NPD5124	Phase 1
0.7256	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6535	Approved
0.7225	Intermediate Similarity	NPD6534	Approved
0.7222	Intermediate Similarity	NPD7701	Phase 2
0.7222	Intermediate Similarity	NPD6808	Phase 2
0.7216	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7783	Phase 2
0.72	Intermediate Similarity	NPD7801	Approved
0.7189	Intermediate Similarity	NPD6764	Approved
0.7189	Intermediate Similarity	NPD6765	Approved
0.7184	Intermediate Similarity	NPD7458	Discontinued
0.7178	Intermediate Similarity	NPD3764	Approved
0.7176	Intermediate Similarity	NPD6190	Approved
0.7174	Intermediate Similarity	NPD1729	Discontinued
0.715	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7874	Approved
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7135	Intermediate Similarity	NPD3823	Discontinued
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7126	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4625	Phase 3
0.7113	Intermediate Similarity	NPD7700	Phase 2
0.7113	Intermediate Similarity	NPD7699	Phase 2
0.7097	Intermediate Similarity	NPD7685	Pre-registration
0.7093	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4060	Phase 1
0.7081	Intermediate Similarity	NPD1203	Approved
0.7073	Intermediate Similarity	NPD3268	Approved
0.7071	Intermediate Similarity	NPD8320	Phase 1
0.7071	Intermediate Similarity	NPD8319	Approved
0.7056	Intermediate Similarity	NPD6823	Phase 2
0.7055	Intermediate Similarity	NPD6832	Phase 2
0.7055	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD230	Phase 1
0.7039	Intermediate Similarity	NPD4111	Phase 1
0.7039	Intermediate Similarity	NPD4665	Approved
0.7037	Intermediate Similarity	NPD6785	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