NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.09
Volume:	276.329
LogP:	3.342
LogD:	2.823
LogS:	-4.07
# Rotatable Bonds:	2
TPSA:	63.58
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	3.178
Fsp3:	0.188
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:	-4.73
MDCK Permeability:	2.7313930331729352e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	88.43814849853516%
Volume Distribution (VD):	1.105
Pgp-substrate:	11.485674858093262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.618
CYP2C19-inhibitor:	0.761
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.749
CYP2C9-substrate:	0.794
CYP2D6-inhibitor:	0.818
CYP2D6-substrate:	0.532
CYP3A4-inhibitor:	0.609
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	2.962
Half-life (T1/2):	0.439

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.905
Maximum Recommended Daily Dose:	0.217
Skin Sensitization:	0.433
Carcinogencity:	0.891
Eye Corrosion:	0.003
Eye Irritation:	0.365
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC270044

Natural Product ID:	NPC270044
*Common Name:**	4-Hydroxy-9-(2-Methylbut-3-En-2-Yl)Furo[3,2-G]Chromen-7-One
IUPAC Name:	4-hydroxy-9-(2-methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one
Synonyms:
Standard InCHIKey:	XYCSWDLNRXCFHA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O4/c1-4-16(2,3)12-14-10(7-8-19-14)13(18)9-5-6-11(17)20-15(9)12/h4-8,18H,1H2,2-3H3
SMILES:	C=CC(c1c2oc(=O)ccc2c(c2c1occ2)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1734870
PubChem CID:	5316520
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens [CHEMONTID:0002830] 5-hydroxypsoralens

*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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO7279	Ferulago capillaries	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO7279	Ferulago capillaries	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	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
Potency	13

Activity Type	# Activity
Individual Protein	9
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	25918.5	nM	PMID[528830]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[528830]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	n.a.	16944.1	nM	PMID[528830]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[528830]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[528830]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[528830]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[528830]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[528830]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	112201.8	nM	PMID[528830]
NPT2	Others	Unspecified		Potency	n.a.	50118.7	nM	PMID[528830]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[528830]
NPT2	Others	Unspecified		Potency	n.a.	39810.7	nM	PMID[528830]

☑ 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 NPC270044 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	366
0.1-0.2	1764
0.2-0.3	3954
0.3-0.4	9870
0.4-0.5	9112
0.5-0.6	4306
0.6-0.7	5773
0.7-0.8	5283
0.8-0.85	1650
0.85-0.9	531
0.9-0.95	86
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC155882
0.9477	High Similarity	NPC269495
0.94	High Similarity	NPC88445
0.9396	High Similarity	NPC74539
0.9396	High Similarity	NPC304443
0.9355	High Similarity	NPC169
0.9338	High Similarity	NPC191104
0.9333	High Similarity	NPC266743
0.9231	High Similarity	NPC239270
0.9231	High Similarity	NPC49009
0.9231	High Similarity	NPC95472
0.9231	High Similarity	NPC303210
0.9172	High Similarity	NPC14822
0.9161	High Similarity	NPC160015
0.9161	High Similarity	NPC247677
0.9133	High Similarity	NPC208584
0.9133	High Similarity	NPC246903
0.9108	High Similarity	NPC260296
0.9108	High Similarity	NPC115432
0.9103	High Similarity	NPC296957
0.9103	High Similarity	NPC260902
0.9097	High Similarity	NPC295608
0.9097	High Similarity	NPC250769
0.9097	High Similarity	NPC278010
0.9091	High Similarity	NPC67654
0.9091	High Similarity	NPC263676
0.9045	High Similarity	NPC244750
0.9045	High Similarity	NPC476349
0.9045	High Similarity	NPC476350
0.9032	High Similarity	NPC213608
0.9032	High Similarity	NPC1477
0.9026	High Similarity	NPC156244
0.9026	High Similarity	NPC116604
0.902	High Similarity	NPC37226
0.902	High Similarity	NPC226644
0.9	High Similarity	NPC166858
0.9	High Similarity	NPC51146
0.9	High Similarity	NPC313036
0.8981	High Similarity	NPC65504
0.8974	High Similarity	NPC474542
0.8968	High Similarity	NPC5871
0.8961	High Similarity	NPC321896
0.8961	High Similarity	NPC476185
0.8954	High Similarity	NPC135325
0.8947	High Similarity	NPC190572
0.8938	High Similarity	NPC155640
0.891	High Similarity	NPC131725
0.891	High Similarity	NPC122365
0.8903	High Similarity	NPC170169
0.8903	High Similarity	NPC290671
0.8902	High Similarity	NPC233956
0.8896	High Similarity	NPC39929
0.8896	High Similarity	NPC296030
0.8896	High Similarity	NPC281835
0.8896	High Similarity	NPC317492
0.8889	High Similarity	NPC320789
0.8889	High Similarity	NPC12148
0.8889	High Similarity	NPC130581
0.8882	High Similarity	NPC230943
0.8875	High Similarity	NPC193998
0.8854	High Similarity	NPC198490
0.8854	High Similarity	NPC148938
0.8846	High Similarity	NPC41326
0.8846	High Similarity	NPC253872
0.8839	High Similarity	NPC135303
0.8839	High Similarity	NPC230713
0.8839	High Similarity	NPC148423
0.8839	High Similarity	NPC78335
0.8831	High Similarity	NPC168085
0.8827	High Similarity	NPC323137
0.8824	High Similarity	NPC51641
0.8824	High Similarity	NPC210826
0.8824	High Similarity	NPC300267
0.8816	High Similarity	NPC225884
0.8816	High Similarity	NPC302181
0.8808	High Similarity	NPC254010
0.8805	High Similarity	NPC40583
0.88	High Similarity	NPC262635
0.879	High Similarity	NPC183874
0.879	High Similarity	NPC472462
0.879	High Similarity	NPC235333
0.8782	High Similarity	NPC115324
0.878	High Similarity	NPC120220
0.8774	High Similarity	NPC221868
0.8774	High Similarity	NPC471114
0.8774	High Similarity	NPC178202
0.8774	High Similarity	NPC37208
0.8766	High Similarity	NPC198427
0.8766	High Similarity	NPC17816
0.8765	High Similarity	NPC259007
0.8765	High Similarity	NPC329215
0.8765	High Similarity	NPC136641
0.8765	High Similarity	NPC204088
0.8758	High Similarity	NPC206212
0.8758	High Similarity	NPC476055
0.8758	High Similarity	NPC71184
0.875	High Similarity	NPC53192
0.8742	High Similarity	NPC164110
0.8742	High Similarity	NPC246647
0.8742	High Similarity	NPC96342
0.8742	High Similarity	NPC268360
0.8742	High Similarity	NPC212967
0.8734	High Similarity	NPC279218
0.8734	High Similarity	NPC108937
0.8734	High Similarity	NPC297531
0.8734	High Similarity	NPC213936
0.8727	High Similarity	NPC472584
0.8726	High Similarity	NPC271681
0.8726	High Similarity	NPC38361
0.8726	High Similarity	NPC130015
0.8726	High Similarity	NPC207624
0.8718	High Similarity	NPC472406
0.8718	High Similarity	NPC474735
0.871	High Similarity	NPC39195
0.871	High Similarity	NPC272194
0.871	High Similarity	NPC306788
0.8704	High Similarity	NPC15819
0.8701	High Similarity	NPC154217
0.8701	High Similarity	NPC470322
0.8696	High Similarity	NPC304387
0.8693	High Similarity	NPC71739
0.8693	High Similarity	NPC11700
0.8688	High Similarity	NPC472877
0.8683	High Similarity	NPC107244
0.8683	High Similarity	NPC472661
0.8679	High Similarity	NPC109967
0.8679	High Similarity	NPC78554
0.8679	High Similarity	NPC469936
0.8679	High Similarity	NPC470625
0.8679	High Similarity	NPC474738
0.8679	High Similarity	NPC129053
0.8679	High Similarity	NPC19860
0.8679	High Similarity	NPC321372
0.8679	High Similarity	NPC13879
0.8679	High Similarity	NPC474609
0.8679	High Similarity	NPC475797
0.8679	High Similarity	NPC180924
0.8675	High Similarity	NPC137009
0.8675	High Similarity	NPC472515
0.8671	High Similarity	NPC41719
0.8667	High Similarity	NPC332594
0.8662	High Similarity	NPC472407
0.8662	High Similarity	NPC58668
0.8662	High Similarity	NPC318424
0.8662	High Similarity	NPC23668
0.8662	High Similarity	NPC193976
0.8662	High Similarity	NPC106372
0.865	High Similarity	NPC38914
0.8645	High Similarity	NPC300988
0.8645	High Similarity	NPC308200
0.8645	High Similarity	NPC10990
0.8642	High Similarity	NPC78612
0.8642	High Similarity	NPC234536
0.8642	High Similarity	NPC219861
0.8636	High Similarity	NPC196137
0.8636	High Similarity	NPC311741
0.8636	High Similarity	NPC234629
0.8636	High Similarity	NPC98926
0.8636	High Similarity	NPC155144
0.8636	High Similarity	NPC303185
0.8636	High Similarity	NPC184649
0.8636	High Similarity	NPC1886
0.8636	High Similarity	NPC469953
0.8634	High Similarity	NPC243509
0.8627	High Similarity	NPC294432
0.8627	High Similarity	NPC112829
0.8627	High Similarity	NPC162476
0.8627	High Similarity	NPC472344
0.8627	High Similarity	NPC470556
0.8627	High Similarity	NPC36181
0.8625	High Similarity	NPC196448
0.8623	High Similarity	NPC224165
0.8623	High Similarity	NPC53917
0.8618	High Similarity	NPC289660
0.8618	High Similarity	NPC101366
0.8618	High Similarity	NPC11056
0.8618	High Similarity	NPC28337
0.8618	High Similarity	NPC470856
0.8618	High Similarity	NPC82920
0.8618	High Similarity	NPC164697
0.8616	High Similarity	NPC469934
0.8616	High Similarity	NPC473193
0.8616	High Similarity	NPC99199
0.8616	High Similarity	NPC233776
0.8614	High Similarity	NPC307286
0.8608	High Similarity	NPC142308
0.8608	High Similarity	NPC327269
0.8608	High Similarity	NPC476238
0.8608	High Similarity	NPC31627
0.8599	High Similarity	NPC180351
0.8599	High Similarity	NPC472421
0.8599	High Similarity	NPC167576
0.8599	High Similarity	NPC188403
0.8599	High Similarity	NPC119929
0.8599	High Similarity	NPC295036
0.8599	High Similarity	NPC29777
0.8599	High Similarity	NPC471115
0.8598	High Similarity	NPC67450
0.8598	High Similarity	NPC210460
0.8598	High Similarity	NPC193881

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 NPC270044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	984
0.2-0.3	1752
0.3-0.4	2649
0.4-0.5	1975
0.5-0.6	993
0.6-0.7	299
0.7-0.8	107
0.8-0.85	30
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9396	High Similarity	NPD920	Approved
0.9133	High Similarity	NPD642	Clinical (unspecified phase)
0.9	High Similarity	NPD643	Clinical (unspecified phase)
0.88	High Similarity	NPD1243	Approved
0.8675	High Similarity	NPD2800	Approved
0.8625	High Similarity	NPD3749	Approved
0.8571	High Similarity	NPD919	Approved
0.8516	High Similarity	NPD4378	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8313	Intermediate Similarity	NPD7411	Suspended
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8282	Intermediate Similarity	NPD7075	Discontinued
0.828	Intermediate Similarity	NPD2534	Approved
0.828	Intermediate Similarity	NPD2532	Approved
0.828	Intermediate Similarity	NPD2533	Approved
0.8261	Intermediate Similarity	NPD6801	Discontinued
0.825	Intermediate Similarity	NPD6599	Discontinued
0.8247	Intermediate Similarity	NPD1549	Phase 2
0.8242	Intermediate Similarity	NPD1247	Approved
0.8235	Intermediate Similarity	NPD6559	Discontinued
0.8235	Intermediate Similarity	NPD1551	Phase 2
0.8221	Intermediate Similarity	NPD7768	Phase 2
0.821	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2344	Approved
0.8182	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1240	Approved
0.8141	Intermediate Similarity	NPD3750	Approved
0.8137	Intermediate Similarity	NPD4380	Phase 2
0.8129	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2796	Approved
0.8101	Intermediate Similarity	NPD6799	Approved
0.8098	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1607	Approved
0.8025	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3882	Suspended
0.7975	Intermediate Similarity	NPD2309	Approved
0.7962	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7286	Phase 2
0.7952	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD2799	Discontinued
0.7927	Intermediate Similarity	NPD1934	Approved
0.7917	Intermediate Similarity	NPD6959	Discontinued
0.7895	Intermediate Similarity	NPD3818	Discontinued
0.7895	Intermediate Similarity	NPD2313	Discontinued
0.7885	Intermediate Similarity	NPD2935	Discontinued
0.7879	Intermediate Similarity	NPD2801	Approved
0.7875	Intermediate Similarity	NPD1511	Approved
0.787	Intermediate Similarity	NPD6232	Discontinued
0.7861	Intermediate Similarity	NPD5953	Discontinued
0.7857	Intermediate Similarity	NPD5494	Approved
0.7853	Intermediate Similarity	NPD3226	Approved
0.7836	Intermediate Similarity	NPD7473	Discontinued
0.7831	Intermediate Similarity	NPD3817	Phase 2
0.7821	Intermediate Similarity	NPD3748	Approved
0.7806	Intermediate Similarity	NPD6651	Approved
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7778	Intermediate Similarity	NPD1512	Approved
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5844	Phase 1
0.7697	Intermediate Similarity	NPD8434	Phase 2
0.7682	Intermediate Similarity	NPD1203	Approved
0.7679	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7661	Intermediate Similarity	NPD5710	Approved
0.7661	Intermediate Similarity	NPD5711	Approved
0.7622	Intermediate Similarity	NPD5403	Approved
0.7619	Intermediate Similarity	NPD5402	Approved
0.7616	Intermediate Similarity	NPD3926	Phase 2
0.7611	Intermediate Similarity	NPD4287	Approved
0.761	Intermediate Similarity	NPD2346	Discontinued
0.7607	Intermediate Similarity	NPD5401	Approved
0.76	Intermediate Similarity	NPD9717	Approved
0.7586	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD422	Phase 1
0.7532	Intermediate Similarity	NPD6832	Phase 2
0.7472	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6166	Phase 2
0.7471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7229	Phase 3
0.7456	Intermediate Similarity	NPD5760	Phase 2
0.7456	Intermediate Similarity	NPD5761	Phase 2
0.7443	Intermediate Similarity	NPD7054	Approved
0.7436	Intermediate Similarity	NPD3268	Approved
0.7412	Intermediate Similarity	NPD2296	Approved
0.7405	Intermediate Similarity	NPD230	Phase 1
0.7405	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD447	Suspended
0.7401	Intermediate Similarity	NPD7472	Approved
0.7401	Intermediate Similarity	NPD1729	Discontinued
0.7401	Intermediate Similarity	NPD7074	Phase 3
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4308	Phase 3
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.736	Intermediate Similarity	NPD6797	Phase 2
0.7356	Intermediate Similarity	NPD6808	Phase 2
0.7338	Intermediate Similarity	NPD2797	Approved
0.7325	Intermediate Similarity	NPD3764	Approved
0.7321	Intermediate Similarity	NPD7458	Discontinued
0.7318	Intermediate Similarity	NPD7251	Discontinued
0.7296	Intermediate Similarity	NPD5124	Phase 1
0.7296	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1019	Discontinued
0.7284	Intermediate Similarity	NPD1471	Phase 3
0.7278	Intermediate Similarity	NPD7808	Phase 3
0.7267	Intermediate Similarity	NPD9545	Approved
0.7263	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7003	Approved
0.7235	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD943	Approved
0.7226	Intermediate Similarity	NPD1164	Approved
0.7226	Intermediate Similarity	NPD3267	Approved
0.7226	Intermediate Similarity	NPD3266	Approved
0.7222	Intermediate Similarity	NPD6100	Approved
0.7222	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD4361	Phase 2
0.7219	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD411	Approved
0.7215	Intermediate Similarity	NPD1296	Phase 2
0.7215	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4288	Approved
0.7202	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6280	Approved
0.7193	Intermediate Similarity	NPD6279	Approved
0.7181	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2798	Approved
0.7178	Intermediate Similarity	NPD6005	Phase 3
0.7178	Intermediate Similarity	NPD6004	Phase 3
0.7178	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6002	Phase 3
0.7166	Intermediate Similarity	NPD4360	Phase 2
0.7166	Intermediate Similarity	NPD4363	Phase 3
0.7161	Intermediate Similarity	NPD3225	Approved
0.7151	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD9493	Approved
0.7127	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7390	Discontinued
0.7125	Intermediate Similarity	NPD4307	Phase 2
0.7118	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2654	Approved
0.7089	Intermediate Similarity	NPD4908	Phase 1
0.7079	Intermediate Similarity	NPD2403	Approved
0.7078	Intermediate Similarity	NPD1610	Phase 2
0.7078	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8312	Approved
0.7049	Intermediate Similarity	NPD8313	Approved
0.7039	Intermediate Similarity	NPD1548	Phase 1
0.7033	Intermediate Similarity	NPD6104	Discontinued
0.7032	Intermediate Similarity	NPD3972	Approved
0.7012	Intermediate Similarity	NPD5405	Approved
0.7012	Intermediate Similarity	NPD5404	Approved
0.7012	Intermediate Similarity	NPD5408	Approved
0.7012	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD7199	Phase 2
0.7	Intermediate Similarity	NPD3751	Discontinued
0.6994	Remote Similarity	NPD37	Approved
0.6989	Remote Similarity	NPD6234	Discontinued
0.6975	Remote Similarity	NPD1933	Approved
0.6975	Remote Similarity	NPD6355	Discontinued
0.6971	Remote Similarity	NPD4965	Approved
0.6971	Remote Similarity	NPD4967	Phase 2
0.6971	Remote Similarity	NPD4966	Approved
0.6951	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD17	Approved
0.694	Remote Similarity	NPD6764	Approved
0.694	Remote Similarity	NPD6765	Approved
0.6936	Remote Similarity	NPD5889	Approved
0.6936	Remote Similarity	NPD5890	Approved
0.6927	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4476	Approved
0.6909	Remote Similarity	NPD4477	Approved
0.6906	Remote Similarity	NPD7177	Discontinued
0.6891	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1652	Phase 2
0.6882	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD8151	Discontinued
0.6857	Remote Similarity	NPD8455	Phase 2
0.6853	Remote Similarity	NPD7584	Approved
0.6839	Remote Similarity	NPD1778	Approved
0.6835	Remote Similarity	NPD1283	Approved
0.6833	Remote Similarity	NPD5242	Approved
0.6832	Remote Similarity	NPD4625	Phase 3
0.6826	Remote Similarity	NPD2424	Discontinued

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