NPASS Compound

Structure

CID318424 OpenBabel06191716142D 24 26 0 0 1 0 0 0 0 0999 V2000 -5.2437 2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1691 3.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 3.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6691 2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 4.2072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 2.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 3.3412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 19 2 0 0 0 0 10 13 1 0 0 0 0 10 20 2 0 0 0 0 11 23 1 0 0 0 0 12 15 2 0 0 0 0 13 18 2 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	325.865
LogP:	3.636
LogD:	2.583
LogS:	-4.042
# Rotatable Bonds:	4
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.838
Synthetic Accessibility Score:	3.17
Fsp3:	0.222
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:	-4.849
MDCK Permeability:	3.1654664780944586e-05
Pgp-inhibitor:	0.096
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	97.72029113769531%
Volume Distribution (VD):	0.415
Pgp-substrate:	1.319549560546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.61
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.761
CYP2C9-substrate:	0.797
CYP2D6-inhibitor:	0.925
CYP2D6-substrate:	0.65
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	6.132
Half-life (T1/2):	0.784

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.921
Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.513
Carcinogencity:	0.965
Eye Corrosion:	0.003
Eye Irritation:	0.117
Respiratory Toxicity:	0.609

Download Data

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

Natural Product: NPC318424

Natural Product ID:	NPC318424
*Common Name:**	(+)-Ganodone
IUPAC Name:	1-[4-[(5-acetyl-4-hydroxy-2,3-dihydro-1-benzofuran-2-yl)oxy]-2-hydroxyphenyl]ethanone
Synonyms:	(+)-Ganodone
Standard InCHIKey:	HNNFEKOVKSPWLT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-9(19)12-4-3-11(7-15(12)21)23-17-8-14-16(24-17)6-5-13(10(2)20)18(14)22/h3-7,17,21-22H,8H2,1-2H3
SMILES:	CC(=O)C1=C(C=C(C=C1)OC2CC3=C(O2)C=CC(=C3O)C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1910158
PubChem CID:	56598740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[10785428]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785428]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21939217]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584403]
NPO2085	Ganoderma tsugae	Species	Ganodermataceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	220.0	nM	PMID[468394]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	490.0	nM	PMID[468394]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	81.0	nM	PMID[468394]

☑ 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 NPC318424 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	357
0.1-0.2	1617
0.2-0.3	3855
0.3-0.4	9320
0.4-0.5	9162
0.5-0.6	3564
0.6-0.7	5613
0.7-0.8	5434
0.8-0.85	2494
0.85-0.9	1062
0.9-0.95	218
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9467	High Similarity	NPC211482
0.9467	High Similarity	NPC476652
0.9388	High Similarity	NPC168085
0.9351	High Similarity	NPC471286
0.9351	High Similarity	NPC91288
0.9324	High Similarity	NPC317492
0.9286	High Similarity	NPC310603
0.9286	High Similarity	NPC93215
0.9276	High Similarity	NPC23817
0.9262	High Similarity	NPC472421
0.9205	High Similarity	NPC168805
0.9205	High Similarity	NPC121910
0.92	High Similarity	NPC474772
0.92	High Similarity	NPC472423
0.92	High Similarity	NPC474744
0.9195	High Similarity	NPC226644
0.9195	High Similarity	NPC39929
0.9195	High Similarity	NPC296030
0.9195	High Similarity	NPC37226
0.9189	High Similarity	NPC12148
0.9189	High Similarity	NPC130581
0.9184	High Similarity	NPC71210
0.9178	High Similarity	NPC266725
0.9167	High Similarity	NPC124269
0.9156	High Similarity	NPC472320
0.915	High Similarity	NPC470606
0.9145	High Similarity	NPC99233
0.9139	High Similarity	NPC473996
0.9139	High Similarity	NPC476238
0.9139	High Similarity	NPC327269
0.9139	High Similarity	NPC31627
0.9133	High Similarity	NPC321896
0.9133	High Similarity	NPC476185
0.9128	High Similarity	NPC39195
0.9128	High Similarity	NPC135325
0.9122	High Similarity	NPC210826
0.9122	High Similarity	NPC300267
0.9122	High Similarity	NPC51641
0.9122	High Similarity	NPC472629
0.9116	High Similarity	NPC257097
0.9116	High Similarity	NPC143896
0.9116	High Similarity	NPC91560
0.9116	High Similarity	NPC150408
0.9116	High Similarity	NPC175504
0.9116	High Similarity	NPC75049
0.9116	High Similarity	NPC39329
0.9116	High Similarity	NPC166138
0.9116	High Similarity	NPC169591
0.9116	High Similarity	NPC68104
0.9116	High Similarity	NPC221432
0.9116	High Similarity	NPC310130
0.9116	High Similarity	NPC18585
0.9116	High Similarity	NPC164980
0.9116	High Similarity	NPC149026
0.9116	High Similarity	NPC106985
0.911	High Similarity	NPC470089
0.911	High Similarity	NPC3188
0.911	High Similarity	NPC321980
0.911	High Similarity	NPC110969
0.911	High Similarity	NPC469404
0.911	High Similarity	NPC470087
0.9103	High Similarity	NPC137009
0.9097	High Similarity	NPC94155
0.9097	High Similarity	NPC188879
0.9091	High Similarity	NPC470607
0.9091	High Similarity	NPC73511
0.9085	High Similarity	NPC149368
0.9085	High Similarity	NPC265480
0.9079	High Similarity	NPC213608
0.9079	High Similarity	NPC106625
0.9079	High Similarity	NPC1477
0.9073	High Similarity	NPC325429
0.9073	High Similarity	NPC290671
0.9073	High Similarity	NPC471291
0.9073	High Similarity	NPC170169
0.9073	High Similarity	NPC471675
0.9073	High Similarity	NPC472580
0.9073	High Similarity	NPC472636
0.906	High Similarity	NPC201731
0.906	High Similarity	NPC308200
0.906	High Similarity	NPC97716
0.906	High Similarity	NPC104406
0.906	High Similarity	NPC237635
0.906	High Similarity	NPC24673
0.906	High Similarity	NPC79469
0.906	High Similarity	NPC14875
0.9054	High Similarity	NPC473013
0.9054	High Similarity	NPC311741
0.9054	High Similarity	NPC273538
0.9054	High Similarity	NPC470890
0.9054	High Similarity	NPC124780
0.9054	High Similarity	NPC87486
0.9054	High Similarity	NPC197252
0.9054	High Similarity	NPC236766
0.9054	High Similarity	NPC216538
0.9054	High Similarity	NPC209040
0.9054	High Similarity	NPC224714
0.9054	High Similarity	NPC473015
0.9054	High Similarity	NPC234629
0.9054	High Similarity	NPC271288
0.9048	High Similarity	NPC324436
0.9048	High Similarity	NPC194432
0.9048	High Similarity	NPC223500
0.9048	High Similarity	NPC144499
0.9048	High Similarity	NPC66515
0.9048	High Similarity	NPC166482
0.9048	High Similarity	NPC40833
0.9048	High Similarity	NPC328164
0.9048	High Similarity	NPC182852
0.9048	High Similarity	NPC306829
0.9048	High Similarity	NPC228504
0.9048	High Similarity	NPC125855
0.9048	High Similarity	NPC296917
0.9048	High Similarity	NPC32739
0.9048	High Similarity	NPC324134
0.9048	High Similarity	NPC64915
0.9048	High Similarity	NPC166934
0.9048	High Similarity	NPC161506
0.9048	High Similarity	NPC37496
0.9048	High Similarity	NPC1089
0.9048	High Similarity	NPC148757
0.9048	High Similarity	NPC167624
0.9048	High Similarity	NPC177354
0.9048	High Similarity	NPC107572
0.9048	High Similarity	NPC471520
0.9048	High Similarity	NPC220998
0.9048	High Similarity	NPC76338
0.9048	High Similarity	NPC78
0.9048	High Similarity	NPC227579
0.9048	High Similarity	NPC11561
0.9048	High Similarity	NPC76372
0.9048	High Similarity	NPC10937
0.9048	High Similarity	NPC265040
0.9048	High Similarity	NPC226636
0.9041	High Similarity	NPC69769
0.9041	High Similarity	NPC259166
0.9041	High Similarity	NPC159275
0.9041	High Similarity	NPC172986
0.9041	High Similarity	NPC172250
0.9041	High Similarity	NPC48624
0.9041	High Similarity	NPC241100
0.9041	High Similarity	NPC270883
0.9041	High Similarity	NPC144118
0.9041	High Similarity	NPC213659
0.9041	High Similarity	NPC204985
0.9041	High Similarity	NPC261227
0.9041	High Similarity	NPC80962
0.9041	High Similarity	NPC326109
0.9041	High Similarity	NPC219917
0.9041	High Similarity	NPC215311
0.9038	High Similarity	NPC125991
0.9038	High Similarity	NPC259834
0.9038	High Similarity	NPC131745
0.9038	High Similarity	NPC44947
0.9034	High Similarity	NPC21350
0.9032	High Similarity	NPC200708
0.9032	High Similarity	NPC306978
0.9028	High Similarity	NPC1486
0.9028	High Similarity	NPC186838
0.9028	High Similarity	NPC240593
0.9028	High Similarity	NPC274109
0.9028	High Similarity	NPC168105
0.9028	High Similarity	NPC249606
0.9028	High Similarity	NPC66349
0.9028	High Similarity	NPC12165
0.9028	High Similarity	NPC150399
0.9028	High Similarity	NPC98115
0.9028	High Similarity	NPC41461
0.9028	High Similarity	NPC477242
0.9028	High Similarity	NPC477244
0.9028	High Similarity	NPC25287
0.9028	High Similarity	NPC477243
0.9026	High Similarity	NPC258035
0.9026	High Similarity	NPC161749
0.9026	High Similarity	NPC156457
0.9026	High Similarity	NPC197896
0.9026	High Similarity	NPC313163
0.9026	High Similarity	NPC43638
0.902	High Similarity	NPC470604
0.902	High Similarity	NPC198490
0.902	High Similarity	NPC92395
0.902	High Similarity	NPC470603
0.902	High Similarity	NPC470605
0.902	High Similarity	NPC87404
0.9013	High Similarity	NPC477957
0.9013	High Similarity	NPC88484
0.9013	High Similarity	NPC259182
0.9013	High Similarity	NPC5871
0.9013	High Similarity	NPC285623
0.9013	High Similarity	NPC259767
0.9013	High Similarity	NPC121001
0.9013	High Similarity	NPC166067
0.9007	High Similarity	NPC61258
0.9007	High Similarity	NPC471984
0.9007	High Similarity	NPC230713
0.9007	High Similarity	NPC78335
0.9	High Similarity	NPC145467
0.9	High Similarity	NPC6511
0.9	High Similarity	NPC266572
0.8993	High Similarity	NPC124729

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 NPC318424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	928
0.2-0.3	1640
0.3-0.4	2612
0.4-0.5	1903
0.5-0.6	1147
0.6-0.7	381
0.7-0.8	152
0.8-0.85	41
0.85-0.9	16
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9054	High Similarity	NPD4378	Clinical (unspecified phase)
0.9026	High Similarity	NPD4381	Clinical (unspecified phase)
0.8812	High Similarity	NPD3818	Discontinued
0.8776	High Similarity	NPD1549	Phase 2
0.8758	High Similarity	NPD7804	Clinical (unspecified phase)
0.8712	High Similarity	NPD6559	Discontinued
0.871	High Similarity	NPD2393	Clinical (unspecified phase)
0.8707	High Similarity	NPD1550	Clinical (unspecified phase)
0.8707	High Similarity	NPD1552	Clinical (unspecified phase)
0.8701	High Similarity	NPD7411	Suspended
0.8699	High Similarity	NPD1510	Phase 2
0.8681	High Similarity	NPD1240	Approved
0.8675	High Similarity	NPD7410	Clinical (unspecified phase)
0.8662	High Similarity	NPD7075	Discontinued
0.8639	High Similarity	NPD2796	Approved
0.8636	High Similarity	NPD4380	Phase 2
0.859	High Similarity	NPD7096	Clinical (unspecified phase)
0.859	High Similarity	NPD7819	Suspended
0.8562	High Similarity	NPD1607	Approved
0.8535	High Similarity	NPD8443	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD6799	Approved
0.8481	Intermediate Similarity	NPD3882	Suspended
0.8476	Intermediate Similarity	NPD7074	Phase 3
0.8467	Intermediate Similarity	NPD2800	Approved
0.8442	Intermediate Similarity	NPD920	Approved
0.8415	Intermediate Similarity	NPD7054	Approved
0.8408	Intermediate Similarity	NPD6801	Discontinued
0.8408	Intermediate Similarity	NPD1934	Approved
0.8365	Intermediate Similarity	NPD7768	Phase 2
0.8364	Intermediate Similarity	NPD7472	Approved
0.8344	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1243	Approved
0.8313	Intermediate Similarity	NPD6797	Phase 2
0.8312	Intermediate Similarity	NPD2534	Approved
0.8312	Intermediate Similarity	NPD2533	Approved
0.8312	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD2532	Approved
0.8301	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6599	Discontinued
0.8267	Intermediate Similarity	NPD2935	Discontinued
0.8267	Intermediate Similarity	NPD1551	Phase 2
0.8263	Intermediate Similarity	NPD7251	Discontinued
0.8247	Intermediate Similarity	NPD1511	Approved
0.8239	Intermediate Similarity	NPD2801	Approved
0.8214	Intermediate Similarity	NPD7808	Phase 3
0.821	Intermediate Similarity	NPD5494	Approved
0.8199	Intermediate Similarity	NPD3749	Approved
0.817	Intermediate Similarity	NPD3750	Approved
0.8163	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6959	Discontinued
0.8141	Intermediate Similarity	NPD1512	Approved
0.8107	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5953	Discontinued
0.8092	Intermediate Similarity	NPD2344	Approved
0.8084	Intermediate Similarity	NPD7286	Phase 2
0.8079	Intermediate Similarity	NPD2799	Discontinued
0.8075	Intermediate Similarity	NPD3817	Phase 2
0.8039	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD6651	Approved
0.7927	Intermediate Similarity	NPD919	Approved
0.7919	Intermediate Similarity	NPD2313	Discontinued
0.7914	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6232	Discontinued
0.7885	Intermediate Similarity	NPD2309	Approved
0.7862	Intermediate Similarity	NPD5403	Approved
0.7857	Intermediate Similarity	NPD7473	Discontinued
0.7843	Intermediate Similarity	NPD3748	Approved
0.7831	Intermediate Similarity	NPD1247	Approved
0.7823	Intermediate Similarity	NPD1203	Approved
0.7821	Intermediate Similarity	NPD4628	Phase 3
0.7785	Intermediate Similarity	NPD6832	Phase 2
0.777	Intermediate Similarity	NPD2798	Approved
0.7765	Intermediate Similarity	NPD5844	Phase 1
0.7764	Intermediate Similarity	NPD7458	Discontinued
0.7764	Intermediate Similarity	NPD3226	Approved
0.7744	Intermediate Similarity	NPD5402	Approved
0.774	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5401	Approved
0.7682	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5711	Approved
0.7679	Intermediate Similarity	NPD5710	Approved
0.7676	Intermediate Similarity	NPD7584	Approved
0.7673	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8313	Approved
0.7644	Intermediate Similarity	NPD8312	Approved
0.7633	Intermediate Similarity	NPD3926	Phase 2
0.7628	Intermediate Similarity	NPD2346	Discontinued
0.7628	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7199	Phase 2
0.7619	Intermediate Similarity	NPD9717	Approved
0.7616	Intermediate Similarity	NPD1729	Discontinued
0.7613	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7033	Discontinued
0.7582	Intermediate Similarity	NPD943	Approved
0.7551	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4908	Phase 1
0.7532	Intermediate Similarity	NPD2654	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7532	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD37	Approved
0.7514	Intermediate Similarity	NPD4361	Phase 2
0.7514	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7229	Phase 3
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD8455	Phase 2
0.7459	Intermediate Similarity	NPD4360	Phase 2
0.7459	Intermediate Similarity	NPD4363	Phase 3
0.7455	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7390	Discontinued
0.7452	Intermediate Similarity	NPD6100	Approved
0.7452	Intermediate Similarity	NPD6099	Approved
0.7451	Intermediate Similarity	NPD3268	Approved
0.7446	Intermediate Similarity	NPD6780	Approved
0.7446	Intermediate Similarity	NPD6778	Approved
0.7446	Intermediate Similarity	NPD6776	Approved
0.7446	Intermediate Similarity	NPD6782	Approved
0.7446	Intermediate Similarity	NPD6781	Approved
0.7446	Intermediate Similarity	NPD6777	Approved
0.7446	Intermediate Similarity	NPD6779	Approved
0.7432	Intermediate Similarity	NPD1610	Phase 2
0.7432	Intermediate Similarity	NPD422	Phase 1
0.7419	Intermediate Similarity	NPD230	Phase 1
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7399	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD9545	Approved
0.7397	Intermediate Similarity	NPD1548	Phase 1
0.7389	Intermediate Similarity	NPD4308	Phase 3
0.7377	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1465	Phase 2
0.7351	Intermediate Similarity	NPD2797	Approved
0.7338	Intermediate Similarity	NPD3764	Approved
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7696	Phase 3
0.7326	Intermediate Similarity	NPD7698	Approved
0.7326	Intermediate Similarity	NPD7435	Discontinued
0.7326	Intermediate Similarity	NPD7697	Approved
0.7321	Intermediate Similarity	NPD2296	Approved
0.7316	Intermediate Similarity	NPD8151	Discontinued
0.7308	Intermediate Similarity	NPD447	Suspended
0.7308	Intermediate Similarity	NPD5124	Phase 1
0.7308	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1019	Discontinued
0.7301	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7228	Approved
0.7296	Intermediate Similarity	NPD6004	Phase 3
0.7296	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6002	Phase 3
0.7296	Intermediate Similarity	NPD6005	Phase 3
0.7296	Intermediate Similarity	NPD1471	Phase 3
0.7296	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7871	Phase 2
0.7287	Intermediate Similarity	NPD7870	Phase 2
0.7273	Intermediate Similarity	NPD1653	Approved
0.7267	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD1608	Approved
0.7267	Intermediate Similarity	NPD3972	Approved
0.7263	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7585	Approved
0.726	Intermediate Similarity	NPD9493	Approved
0.7238	Intermediate Similarity	NPD4287	Approved
0.7237	Intermediate Similarity	NPD1164	Approved
0.7229	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD411	Approved
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD4288	Approved
0.7211	Intermediate Similarity	NPD7583	Approved
0.7202	Intermediate Similarity	NPD6280	Approved
0.7202	Intermediate Similarity	NPD6279	Approved
0.72	Intermediate Similarity	NPD1091	Approved
0.7197	Intermediate Similarity	NPD6355	Discontinued
0.7184	Intermediate Similarity	NPD2403	Approved
0.7181	Intermediate Similarity	NPD6823	Phase 2
0.7174	Intermediate Similarity	NPD6534	Approved
0.7174	Intermediate Similarity	NPD6535	Approved
0.7173	Intermediate Similarity	NPD7701	Phase 2
0.7172	Intermediate Similarity	NPD1241	Discontinued
0.7171	Intermediate Similarity	NPD3225	Approved
0.7168	Intermediate Similarity	NPD6808	Phase 2
0.7166	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD5761	Phase 2
0.716	Intermediate Similarity	NPD5760	Phase 2
0.716	Intermediate Similarity	NPD7003	Approved
0.715	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD5889	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