NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	273.096
LogP:	1.653
LogD:	1.268
LogS:	-3.229
# Rotatable Bonds:	1
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.777
Synthetic Accessibility Score:	3.941
Fsp3:	0.4
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:	-4.811
MDCK Permeability:	1.5604065993102267e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	91.36157989501953%
Volume Distribution (VD):	0.783
Pgp-substrate:	14.627941131591797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.862
CYP2C19-inhibitor:	0.248
CYP2C19-substrate:	0.648
CYP2C9-inhibitor:	0.375
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.217
CYP2D6-substrate:	0.556
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.35

ADMET: Excretion

Clearance (CL):	5.642
Half-life (T1/2):	0.804

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.509
Drug-inuced Liver Injury (DILI):	0.767
AMES Toxicity:	0.235
Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.288
Skin Sensitization:	0.838
Carcinogencity:	0.726
Eye Corrosion:	0.039
Eye Irritation:	0.908
Respiratory Toxicity:	0.083

Download Data

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

Natural Product: NPC51087

Natural Product ID:	NPC51087
*Common Name:**	(2S,3R)-8-Hydroxy-3-(Hydroxymethyl)-2,3,9-Trimethyl-2H-Furo[3,2-C]Chromen-4-One
IUPAC Name:	(2S,3R)-8-hydroxy-3-(hydroxymethyl)-2,3,9-trimethyl-2H-furo[3,2-c]chromen-4-one
Synonyms:
Standard InCHIKey:	AMXIALDGAYCNAK-VXJOIVPMSA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-7-9(17)4-5-10-11(7)13-12(14(18)20-10)15(3,6-16)8(2)19-13/h4-5,8,16-17H,6H2,1-3H3/t8-,15+/m0/s1
SMILES:	OC[C@]1(C)[C@H](C)Oc2c1c(=O)oc1c2c(C)c(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL123946
PubChem CID:	44346830
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002568] Angular furanocoumarins

*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
NPO22473	Aspergillus clavatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24838010]
NPO23161	Dosidicus gigas	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21013	Lonchocarpus castilloi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22473	Aspergillus clavatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22124	Senecio integrifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15107	Eledone moschata	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9969	Nassarius reticulatus	Species	Nassariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11676	[candida] zeylanoides	Species	Debaryomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21185	Manica rubida	Species	Formicidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5.7	ug.mL-1	PMID[540289]

☑ 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 NPC51087 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	349
0.1-0.2	1631
0.2-0.3	3741
0.3-0.4	9120
0.4-0.5	9933
0.5-0.6	4241
0.6-0.7	6355
0.7-0.8	6702
0.8-0.85	580
0.85-0.9	40
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC161856
0.9845	High Similarity	NPC281169
0.9845	High Similarity	NPC291119
0.9062	High Similarity	NPC248786
0.8603	High Similarity	NPC329427
0.8603	High Similarity	NPC317601
0.855	High Similarity	NPC477151
0.855	High Similarity	NPC132518
0.8462	Intermediate Similarity	NPC193193
0.8357	Intermediate Similarity	NPC115861
0.8321	Intermediate Similarity	NPC31314
0.8309	Intermediate Similarity	NPC81261
0.8235	Intermediate Similarity	NPC95034
0.8235	Intermediate Similarity	NPC142087
0.8209	Intermediate Similarity	NPC477152
0.8182	Intermediate Similarity	NPC14177
0.8182	Intermediate Similarity	NPC474874
0.8154	Intermediate Similarity	NPC163398
0.8154	Intermediate Similarity	NPC33717
0.8134	Intermediate Similarity	NPC302211
0.8112	Intermediate Similarity	NPC474943
0.8112	Intermediate Similarity	NPC475005
0.8085	Intermediate Similarity	NPC27394
0.8071	Intermediate Similarity	NPC470160
0.806	Intermediate Similarity	NPC476165
0.8056	Intermediate Similarity	NPC475045
0.8043	Intermediate Similarity	NPC176590
0.8042	Intermediate Similarity	NPC131198
0.8041	Intermediate Similarity	NPC60389
0.8041	Intermediate Similarity	NPC11800
0.8041	Intermediate Similarity	NPC206579
0.803	Intermediate Similarity	NPC283616
0.8028	Intermediate Similarity	NPC475011
0.8028	Intermediate Similarity	NPC475029
0.8028	Intermediate Similarity	NPC476018
0.8014	Intermediate Similarity	NPC329493
0.8	Intermediate Similarity	NPC87563
0.8	Intermediate Similarity	NPC475044
0.8	Intermediate Similarity	NPC470837
0.8	Intermediate Similarity	NPC7012
0.8	Intermediate Similarity	NPC475063
0.8	Intermediate Similarity	NPC476332
0.8	Intermediate Similarity	NPC46634
0.8	Intermediate Similarity	NPC473464
0.7986	Intermediate Similarity	NPC327612
0.7986	Intermediate Similarity	NPC319870
0.7986	Intermediate Similarity	NPC73078
0.7986	Intermediate Similarity	NPC59654
0.7986	Intermediate Similarity	NPC148738
0.7972	Intermediate Similarity	NPC21797
0.7972	Intermediate Similarity	NPC246177
0.7972	Intermediate Similarity	NPC194847
0.7972	Intermediate Similarity	NPC317045
0.7971	Intermediate Similarity	NPC71525
0.7943	Intermediate Similarity	NPC194277
0.7939	Intermediate Similarity	NPC301321
0.7933	Intermediate Similarity	NPC146388
0.7931	Intermediate Similarity	NPC475012
0.7929	Intermediate Similarity	NPC475880
0.7919	Intermediate Similarity	NPC308799
0.7919	Intermediate Similarity	NPC211565
0.7917	Intermediate Similarity	NPC471542
0.7905	Intermediate Similarity	NPC89664
0.7905	Intermediate Similarity	NPC274085
0.7905	Intermediate Similarity	NPC71739
0.7899	Intermediate Similarity	NPC101894
0.7895	Intermediate Similarity	NPC329980
0.7887	Intermediate Similarity	NPC163557
0.7887	Intermediate Similarity	NPC31849
0.7883	Intermediate Similarity	NPC474237
0.7883	Intermediate Similarity	NPC265910
0.7883	Intermediate Similarity	NPC91475
0.7881	Intermediate Similarity	NPC146014
0.7877	Intermediate Similarity	NPC155552
0.7877	Intermediate Similarity	NPC473499
0.7877	Intermediate Similarity	NPC138149
0.7872	Intermediate Similarity	NPC258073
0.7867	Intermediate Similarity	NPC61284
0.7867	Intermediate Similarity	NPC113428
0.7863	Intermediate Similarity	NPC197513
0.7862	Intermediate Similarity	NPC475028
0.7862	Intermediate Similarity	NPC43500
0.7862	Intermediate Similarity	NPC476025
0.7862	Intermediate Similarity	NPC164148
0.7857	Intermediate Similarity	NPC271832
0.7857	Intermediate Similarity	NPC238309
0.7852	Intermediate Similarity	NPC322569
0.7847	Intermediate Similarity	NPC92932
0.7843	Intermediate Similarity	NPC477690
0.7843	Intermediate Similarity	NPC281272
0.7842	Intermediate Similarity	NPC121740
0.7842	Intermediate Similarity	NPC470841
0.7842	Intermediate Similarity	NPC258567
0.7842	Intermediate Similarity	NPC224774
0.7838	Intermediate Similarity	NPC257404
0.7838	Intermediate Similarity	NPC474599
0.7836	Intermediate Similarity	NPC98748
0.7836	Intermediate Similarity	NPC471449
0.7832	Intermediate Similarity	NPC477210
0.7832	Intermediate Similarity	NPC326600
0.7832	Intermediate Similarity	NPC211164
0.7832	Intermediate Similarity	NPC50896
0.7832	Intermediate Similarity	NPC204353
0.7829	Intermediate Similarity	NPC141068
0.7826	Intermediate Similarity	NPC320847
0.7823	Intermediate Similarity	NPC93640
0.7823	Intermediate Similarity	NPC164599
0.7823	Intermediate Similarity	NPC20631
0.7821	Intermediate Similarity	NPC218818
0.7821	Intermediate Similarity	NPC4950
0.7821	Intermediate Similarity	NPC477692
0.7817	Intermediate Similarity	NPC51262
0.7817	Intermediate Similarity	NPC251549
0.7815	Intermediate Similarity	NPC471641
0.7815	Intermediate Similarity	NPC471642
0.7815	Intermediate Similarity	NPC240253
0.7815	Intermediate Similarity	NPC240622
0.7808	Intermediate Similarity	NPC79372
0.7806	Intermediate Similarity	NPC469507
0.7801	Intermediate Similarity	NPC2989
0.7792	Intermediate Similarity	NPC477691
0.7786	Intermediate Similarity	NPC201419
0.7786	Intermediate Similarity	NPC219923
0.7786	Intermediate Similarity	NPC469453
0.7778	Intermediate Similarity	NPC142027
0.777	Intermediate Similarity	NPC329272
0.777	Intermediate Similarity	NPC474385
0.777	Intermediate Similarity	NPC474154
0.777	Intermediate Similarity	NPC229916
0.777	Intermediate Similarity	NPC230157
0.7769	Intermediate Similarity	NPC275627
0.7762	Intermediate Similarity	NPC277021
0.7762	Intermediate Similarity	NPC470871
0.7755	Intermediate Similarity	NPC477537
0.7755	Intermediate Similarity	NPC477535
0.7755	Intermediate Similarity	NPC300611
0.7754	Intermediate Similarity	NPC147896
0.7754	Intermediate Similarity	NPC276962
0.7754	Intermediate Similarity	NPC190086
0.7752	Intermediate Similarity	NPC149545
0.7748	Intermediate Similarity	NPC83975
0.7748	Intermediate Similarity	NPC66991
0.7748	Intermediate Similarity	NPC142863
0.7746	Intermediate Similarity	NPC474246
0.7746	Intermediate Similarity	NPC474143
0.7744	Intermediate Similarity	NPC154256
0.7744	Intermediate Similarity	NPC290470
0.774	Intermediate Similarity	NPC126739
0.774	Intermediate Similarity	NPC151946
0.774	Intermediate Similarity	NPC197666
0.774	Intermediate Similarity	NPC13067
0.774	Intermediate Similarity	NPC98395
0.774	Intermediate Similarity	NPC265335
0.7737	Intermediate Similarity	NPC217756
0.7737	Intermediate Similarity	NPC325301
0.7733	Intermediate Similarity	NPC97662
0.7733	Intermediate Similarity	NPC469408
0.773	Intermediate Similarity	NPC131684
0.773	Intermediate Similarity	NPC474289
0.7727	Intermediate Similarity	NPC183536
0.7727	Intermediate Similarity	NPC271681
0.7727	Intermediate Similarity	NPC474843
0.7727	Intermediate Similarity	NPC34965
0.7727	Intermediate Similarity	NPC44606
0.7724	Intermediate Similarity	NPC26954
0.7724	Intermediate Similarity	NPC126682
0.7724	Intermediate Similarity	NPC38099
0.7724	Intermediate Similarity	NPC223616
0.7724	Intermediate Similarity	NPC82271
0.7718	Intermediate Similarity	NPC51106
0.7718	Intermediate Similarity	NPC469542
0.7714	Intermediate Similarity	NPC319422
0.7714	Intermediate Similarity	NPC477211
0.7714	Intermediate Similarity	NPC181715
0.7714	Intermediate Similarity	NPC477212
0.7714	Intermediate Similarity	NPC477214
0.771	Intermediate Similarity	NPC474920
0.7708	Intermediate Similarity	NPC224475
0.7708	Intermediate Similarity	NPC180716
0.7708	Intermediate Similarity	NPC474097
0.7708	Intermediate Similarity	NPC62366
0.7708	Intermediate Similarity	NPC213173
0.7707	Intermediate Similarity	NPC239118
0.7704	Intermediate Similarity	NPC234956
0.7703	Intermediate Similarity	NPC90411
0.7703	Intermediate Similarity	NPC158634
0.7703	Intermediate Similarity	NPC130485
0.7703	Intermediate Similarity	NPC469564
0.7698	Intermediate Similarity	NPC170749
0.7697	Intermediate Similarity	NPC228012
0.7692	Intermediate Similarity	NPC55463
0.7692	Intermediate Similarity	NPC307289
0.7692	Intermediate Similarity	NPC477406
0.7692	Intermediate Similarity	NPC166116
0.7687	Intermediate Similarity	NPC476191
0.7687	Intermediate Similarity	NPC32360
0.7682	Intermediate Similarity	NPC286038
0.7682	Intermediate Similarity	NPC32058
0.7682	Intermediate Similarity	NPC85734
0.7682	Intermediate Similarity	NPC178129

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 NPC51087 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	956
0.2-0.3	1709
0.3-0.4	2576
0.4-0.5	2021
0.5-0.6	1097
0.6-0.7	349
0.7-0.8	122
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8258	Intermediate Similarity	NPD3496	Discontinued
0.7956	Intermediate Similarity	NPD2797	Approved
0.791	Intermediate Similarity	NPD1778	Approved
0.7801	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD3268	Approved
0.7708	Intermediate Similarity	NPD6653	Approved
0.7704	Intermediate Similarity	NPD5585	Approved
0.7692	Intermediate Similarity	NPD4140	Approved
0.7671	Intermediate Similarity	NPD2935	Discontinued
0.7664	Intermediate Similarity	NPD422	Phase 1
0.7664	Intermediate Similarity	NPD1611	Approved
0.7639	Intermediate Similarity	NPD447	Suspended
0.7626	Intermediate Similarity	NPD3225	Approved
0.7616	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD9717	Approved
0.7584	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1203	Approved
0.7569	Intermediate Similarity	NPD4060	Phase 1
0.7568	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6273	Approved
0.7552	Intermediate Similarity	NPD7985	Registered
0.7537	Intermediate Similarity	NPD6671	Approved
0.7532	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD6696	Suspended
0.7483	Intermediate Similarity	NPD7033	Discontinued
0.7468	Intermediate Similarity	NPD1653	Approved
0.7447	Intermediate Similarity	NPD6362	Approved
0.7447	Intermediate Similarity	NPD3267	Approved
0.7447	Intermediate Similarity	NPD3266	Approved
0.7445	Intermediate Similarity	NPD5691	Approved
0.7431	Intermediate Similarity	NPD411	Approved
0.7429	Intermediate Similarity	NPD4359	Approved
0.7413	Intermediate Similarity	NPD6832	Phase 2
0.741	Intermediate Similarity	NPD1535	Discovery
0.7405	Intermediate Similarity	NPD5402	Approved
0.7397	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6355	Discontinued
0.7383	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2346	Discontinued
0.7383	Intermediate Similarity	NPD5763	Approved
0.7383	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5762	Approved
0.7383	Intermediate Similarity	NPD6002	Phase 3
0.7383	Intermediate Similarity	NPD6005	Phase 3
0.7383	Intermediate Similarity	NPD6004	Phase 3
0.7379	Intermediate Similarity	NPD6233	Phase 2
0.7365	Intermediate Similarity	NPD4308	Phase 3
0.7357	Intermediate Similarity	NPD1481	Phase 2
0.7351	Intermediate Similarity	NPD4628	Phase 3
0.7351	Intermediate Similarity	NPD3750	Approved
0.7351	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2861	Phase 2
0.7333	Intermediate Similarity	NPD2424	Discontinued
0.7333	Intermediate Similarity	NPD5844	Phase 1
0.7315	Intermediate Similarity	NPD6032	Approved
0.731	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD9697	Approved
0.7285	Intermediate Similarity	NPD1652	Phase 2
0.7279	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD2534	Approved
0.7273	Intermediate Similarity	NPD5647	Approved
0.7273	Intermediate Similarity	NPD2533	Approved
0.7273	Intermediate Similarity	NPD1578	Phase 2
0.7273	Intermediate Similarity	NPD2532	Approved
0.7273	Intermediate Similarity	NPD1019	Discontinued
0.726	Intermediate Similarity	NPD4870	Approved
0.726	Intermediate Similarity	NPD8032	Phase 2
0.7259	Intermediate Similarity	NPD1398	Phase 1
0.7252	Intermediate Similarity	NPD968	Approved
0.7241	Intermediate Similarity	NPD7095	Approved
0.7237	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4110	Phase 3
0.7234	Intermediate Similarity	NPD1608	Approved
0.7222	Intermediate Similarity	NPD5736	Approved
0.72	Intermediate Similarity	NPD1551	Phase 2
0.72	Intermediate Similarity	NPD6100	Approved
0.72	Intermediate Similarity	NPD6099	Approved
0.7197	Intermediate Similarity	NPD290	Approved
0.7197	Intermediate Similarity	NPD3226	Approved
0.7192	Intermediate Similarity	NPD6798	Discontinued
0.7192	Intermediate Similarity	NPD2313	Discontinued
0.7192	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8127	Discontinued
0.7174	Intermediate Similarity	NPD7644	Approved
0.7163	Intermediate Similarity	NPD1091	Approved
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1283	Approved
0.7133	Intermediate Similarity	NPD2799	Discontinued
0.7125	Intermediate Similarity	NPD2801	Approved
0.7125	Intermediate Similarity	NPD7819	Suspended
0.7103	Intermediate Similarity	NPD2237	Approved
0.7101	Intermediate Similarity	NPD7340	Approved
0.7101	Intermediate Similarity	NPD9493	Approved
0.7095	Intermediate Similarity	NPD4307	Phase 2
0.7086	Intermediate Similarity	NPD4477	Approved
0.7086	Intermediate Similarity	NPD4476	Approved
0.7063	Intermediate Similarity	NPD37	Approved
0.7063	Intermediate Similarity	NPD6844	Discontinued
0.7037	Intermediate Similarity	NPD4966	Approved
0.7037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4965	Approved
0.7037	Intermediate Similarity	NPD4967	Phase 2
0.7034	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7157	Approved
0.7027	Intermediate Similarity	NPD6663	Approved
0.7025	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD17	Approved
0.702	Intermediate Similarity	NPD3748	Approved
0.7019	Intermediate Similarity	NPD1465	Phase 2
0.7013	Intermediate Similarity	NPD7003	Approved
0.7013	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4625	Phase 3
0.7007	Intermediate Similarity	NPD1241	Discontinued
0.7006	Intermediate Similarity	NPD2676	Approved
0.7006	Intermediate Similarity	NPD2675	Approved
0.7	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD1894	Discontinued
0.698	Remote Similarity	NPD2979	Phase 3
0.698	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1613	Approved
0.6962	Remote Similarity	NPD5403	Approved
0.6962	Remote Similarity	NPD920	Approved
0.6959	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1048	Approved
0.6959	Remote Similarity	NPD1296	Phase 2
0.6954	Remote Similarity	NPD7097	Phase 1
0.6951	Remote Similarity	NPD6234	Discontinued
0.6948	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2800	Approved
0.6944	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5327	Phase 3
0.6944	Remote Similarity	NPD4749	Approved
0.6943	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1358	Approved
0.6939	Remote Similarity	NPD596	Approved
0.6939	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4908	Phase 1
0.6939	Remote Similarity	NPD600	Approved
0.6934	Remote Similarity	NPD5535	Approved
0.6933	Remote Similarity	NPD5735	Approved
0.6928	Remote Similarity	NPD7229	Phase 3
0.6928	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD1610	Phase 2
0.6914	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD840	Approved
0.6913	Remote Similarity	NPD4062	Phase 3
0.6913	Remote Similarity	NPD839	Approved
0.689	Remote Similarity	NPD3749	Approved
0.6883	Remote Similarity	NPD4534	Discontinued
0.6883	Remote Similarity	NPD1549	Phase 2
0.6879	Remote Similarity	NPD1511	Approved
0.6875	Remote Similarity	NPD2649	Approved
0.6875	Remote Similarity	NPD2651	Approved
0.6875	Remote Similarity	NPD2231	Phase 2
0.6875	Remote Similarity	NPD2235	Phase 2
0.6871	Remote Similarity	NPD1712	Approved
0.6871	Remote Similarity	NPD3817	Phase 2
0.6867	Remote Similarity	NPD7199	Phase 2
0.6867	Remote Similarity	NPD6959	Discontinued
0.6866	Remote Similarity	NPD3134	Approved
0.6864	Remote Similarity	NPD3751	Discontinued
0.6864	Remote Similarity	NPD3818	Discontinued
0.6863	Remote Similarity	NPD2438	Suspended
0.6853	Remote Similarity	NPD3847	Discontinued
0.6852	Remote Similarity	NPD1934	Approved
0.6852	Remote Similarity	NPD6801	Discontinued
0.6846	Remote Similarity	NPD3764	Approved
0.6846	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5401	Approved
0.6832	Remote Similarity	NPD6599	Discontinued
0.6831	Remote Similarity	NPD1651	Approved
0.6831	Remote Similarity	NPD1357	Approved
0.6829	Remote Similarity	NPD3882	Suspended
0.6829	Remote Similarity	NPD7768	Phase 2
0.6828	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6232	Discontinued
0.6826	Remote Similarity	NPD3787	Discontinued
0.6824	Remote Similarity	NPD2614	Approved
0.6821	Remote Similarity	NPD230	Phase 1
0.6821	Remote Similarity	NPD4618	Approved
0.6821	Remote Similarity	NPD4622	Approved
0.6821	Remote Similarity	NPD8312	Approved
0.6821	Remote Similarity	NPD8313	Approved
0.6818	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2344	Approved
0.6806	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2798	Approved
0.6803	Remote Similarity	NPD558	Phase 2
0.6797	Remote Similarity	NPD1510	Phase 2
0.6795	Remote Similarity	NPD8166	Discontinued
0.6792	Remote Similarity	NPD1512	Approved
0.679	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7075	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