NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.04
Volume:	247.89
LogP:	2.816
LogD:	2.345
LogS:	-4.219
# Rotatable Bonds:	1
TPSA:	84.58
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	2.573
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.677
MDCK Permeability:	1.8607668607728556e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	92.72219848632812%
Volume Distribution (VD):	0.673
Pgp-substrate:	4.72839879989624%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.353
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.582
CYP2C9-substrate:	0.346
CYP2D6-inhibitor:	0.365
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.515
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	1.75
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.935
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.157
Skin Sensitization:	0.093
Carcinogencity:	0.944
Eye Corrosion:	0.006
Eye Irritation:	0.947
Respiratory Toxicity:	0.086

Download Data

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

Natural Product: NPC252208

Natural Product ID:	NPC252208
*Common Name:**	2-Acetyl-8-Hydroxynaphtho-[2,3-B]Furan-4,9-Dione
IUPAC Name:	2-acetyl-8-hydroxybenzo[f][1]benzofuran-4,9-dione
Synonyms:
Standard InCHIKey:	MYDAXHYLQBNETF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H8O5/c1-6(15)10-5-8-12(17)7-3-2-4-9(16)11(7)13(18)14(8)19-10/h2-5,16H,1H3
SMILES:	CC(=O)c1cc2c(o1)C(=O)c1c(C2=O)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL493650
PubChem CID:	9881541
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[19674905]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32044231]
NPO3751	Orthantha lutea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12083	Hydnellum zonatum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	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
EC50	5
IC50	2
Others	6

Activity Type	# Activity
Cell Line	6
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	=	300.0	nM	PMID[472658]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	346.0	mU	PMID[472658]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	2610.0	nM	PMID[472659]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	=	3000.0	nM	PMID[472659]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	4310.0	nM	PMID[472659]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[472659]
NPT27	Others	Unspecified		EC50	=	11700.0	nM	PMID[472659]
NPT27	Others	Unspecified		EC50	=	14600.0	nM	PMID[472659]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[472659]
NPT2	Others	Unspecified		Activity	=	8.3	%	PMID[472659]
NPT2	Others	Unspecified		Activity	=	27.5	%	PMID[472659]
NPT2	Others	Unspecified		Activity	=	60.3	%	PMID[472659]
NPT2	Others	Unspecified		IC50	=	40100.0	nM	PMID[472659]

☑ 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 NPC252208 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	406
0.1-0.2	1741
0.2-0.3	4244
0.3-0.4	10494
0.4-0.5	7877
0.5-0.6	4591
0.6-0.7	6547
0.7-0.8	6389
0.8-0.85	380
0.85-0.9	15
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC226578
0.9396	High Similarity	NPC317900
0.9396	High Similarity	NPC294300
0.9396	High Similarity	NPC476404
0.9357	High Similarity	NPC265181
0.9267	High Similarity	NPC104380
0.9267	High Similarity	NPC217602
0.9267	High Similarity	NPC473282
0.9247	High Similarity	NPC280025
0.906	High Similarity	NPC471613
0.8693	High Similarity	NPC88958
0.8592	High Similarity	NPC205360
0.8571	High Similarity	NPC290927
0.8571	High Similarity	NPC235333
0.8562	High Similarity	NPC23668
0.8562	High Similarity	NPC193976
0.8562	High Similarity	NPC115324
0.8526	High Similarity	NPC246647
0.8526	High Similarity	NPC164110
0.8526	High Similarity	NPC212967
0.8526	High Similarity	NPC96342
0.8516	High Similarity	NPC148938
0.8516	High Similarity	NPC213936
0.8516	High Similarity	NPC297531
0.8506	High Similarity	NPC142308
0.8506	High Similarity	NPC207624
0.8503	High Similarity	NPC477408
0.8493	Intermediate Similarity	NPC284184
0.8493	Intermediate Similarity	NPC477534
0.8481	Intermediate Similarity	NPC24761
0.8472	Intermediate Similarity	NPC171968
0.8462	Intermediate Similarity	NPC221992
0.8462	Intermediate Similarity	NPC180924
0.8452	Intermediate Similarity	NPC179170
0.8452	Intermediate Similarity	NPC158261
0.8452	Intermediate Similarity	NPC42458
0.8447	Intermediate Similarity	NPC95715
0.8442	Intermediate Similarity	NPC145830
0.8442	Intermediate Similarity	NPC106372
0.8442	Intermediate Similarity	NPC58668
0.8428	Intermediate Similarity	NPC193998
0.8425	Intermediate Similarity	NPC232996
0.8425	Intermediate Similarity	NPC141934
0.8411	Intermediate Similarity	NPC98926
0.8411	Intermediate Similarity	NPC155144
0.8408	Intermediate Similarity	NPC201127
0.8408	Intermediate Similarity	NPC268360
0.8408	Intermediate Similarity	NPC299094
0.8408	Intermediate Similarity	NPC10051
0.84	Intermediate Similarity	NPC117674
0.84	Intermediate Similarity	NPC53016
0.8397	Intermediate Similarity	NPC99199
0.8395	Intermediate Similarity	NPC202470
0.838	Intermediate Similarity	NPC237225
0.8377	Intermediate Similarity	NPC167576
0.8377	Intermediate Similarity	NPC230713
0.8377	Intermediate Similarity	NPC78335
0.8367	Intermediate Similarity	NPC301341
0.8366	Intermediate Similarity	NPC192069
0.8365	Intermediate Similarity	NPC269117
0.8356	Intermediate Similarity	NPC22222
0.8356	Intermediate Similarity	NPC281513
0.8354	Intermediate Similarity	NPC228501
0.8345	Intermediate Similarity	NPC477536
0.8344	Intermediate Similarity	NPC93241
0.8344	Intermediate Similarity	NPC27798
0.8344	Intermediate Similarity	NPC28042
0.8333	Intermediate Similarity	NPC324488
0.8333	Intermediate Similarity	NPC473945
0.8333	Intermediate Similarity	NPC69755
0.8333	Intermediate Similarity	NPC141549
0.8333	Intermediate Similarity	NPC186392
0.8333	Intermediate Similarity	NPC214632
0.8323	Intermediate Similarity	NPC170169
0.8322	Intermediate Similarity	NPC477537
0.8312	Intermediate Similarity	NPC178202
0.8302	Intermediate Similarity	NPC472782
0.8302	Intermediate Similarity	NPC313368
0.8302	Intermediate Similarity	NPC472781
0.8301	Intermediate Similarity	NPC478018
0.8301	Intermediate Similarity	NPC17816
0.8289	Intermediate Similarity	NPC73416
0.8289	Intermediate Similarity	NPC160777
0.8289	Intermediate Similarity	NPC478019
0.8276	Intermediate Similarity	NPC477406
0.8269	Intermediate Similarity	NPC253872
0.8269	Intermediate Similarity	NPC67654
0.8267	Intermediate Similarity	NPC124365
0.8264	Intermediate Similarity	NPC278787
0.8264	Intermediate Similarity	NPC198305
0.8261	Intermediate Similarity	NPC109180
0.8258	Intermediate Similarity	NPC470107
0.8255	Intermediate Similarity	NPC114620
0.8255	Intermediate Similarity	NPC103337
0.8255	Intermediate Similarity	NPC1268
0.825	Intermediate Similarity	NPC472780
0.825	Intermediate Similarity	NPC472783
0.8243	Intermediate Similarity	NPC177262
0.8239	Intermediate Similarity	NPC51037
0.8235	Intermediate Similarity	NPC281398
0.8231	Intermediate Similarity	NPC217914
0.8228	Intermediate Similarity	NPC160015
0.8228	Intermediate Similarity	NPC247677
0.8227	Intermediate Similarity	NPC310540
0.8224	Intermediate Similarity	NPC469385
0.8224	Intermediate Similarity	NPC19896
0.8224	Intermediate Similarity	NPC477409
0.8217	Intermediate Similarity	NPC72370
0.8217	Intermediate Similarity	NPC472462
0.8214	Intermediate Similarity	NPC475996
0.821	Intermediate Similarity	NPC314653
0.821	Intermediate Similarity	NPC316262
0.8205	Intermediate Similarity	NPC258249
0.8205	Intermediate Similarity	NPC156244
0.82	Intermediate Similarity	NPC477535
0.8199	Intermediate Similarity	NPC477239
0.8199	Intermediate Similarity	NPC3448
0.8194	Intermediate Similarity	NPC10027
0.8194	Intermediate Similarity	NPC70764
0.8194	Intermediate Similarity	NPC37226
0.8194	Intermediate Similarity	NPC65775
0.8194	Intermediate Similarity	NPC226644
0.8194	Intermediate Similarity	NPC198927
0.8194	Intermediate Similarity	NPC37220
0.8188	Intermediate Similarity	NPC173980
0.8188	Intermediate Similarity	NPC254841
0.8188	Intermediate Similarity	NPC62735
0.8182	Intermediate Similarity	NPC259632
0.8176	Intermediate Similarity	NPC260902
0.8176	Intermediate Similarity	NPC296957
0.8176	Intermediate Similarity	NPC163029
0.817	Intermediate Similarity	NPC474261
0.817	Intermediate Similarity	NPC230943
0.817	Intermediate Similarity	NPC28632
0.8165	Intermediate Similarity	NPC268008
0.8165	Intermediate Similarity	NPC80489
0.8165	Intermediate Similarity	NPC198490
0.8158	Intermediate Similarity	NPC158871
0.8158	Intermediate Similarity	NPC471520
0.8158	Intermediate Similarity	NPC66593
0.8158	Intermediate Similarity	NPC53192
0.8153	Intermediate Similarity	NPC40356
0.8153	Intermediate Similarity	NPC41326
0.8153	Intermediate Similarity	NPC154683
0.8153	Intermediate Similarity	NPC263676
0.8148	Intermediate Similarity	NPC1755
0.8148	Intermediate Similarity	NPC39305
0.8148	Intermediate Similarity	NPC59295
0.8148	Intermediate Similarity	NPC1706
0.8148	Intermediate Similarity	NPC476931
0.8148	Intermediate Similarity	NPC263092
0.8146	Intermediate Similarity	NPC84273
0.8146	Intermediate Similarity	NPC28337
0.8146	Intermediate Similarity	NPC275734
0.8141	Intermediate Similarity	NPC227122
0.8141	Intermediate Similarity	NPC144010
0.8141	Intermediate Similarity	NPC202595
0.8141	Intermediate Similarity	NPC295036
0.8141	Intermediate Similarity	NPC13282
0.8138	Intermediate Similarity	NPC7569
0.8137	Intermediate Similarity	NPC476929
0.8137	Intermediate Similarity	NPC304387
0.8137	Intermediate Similarity	NPC478134
0.8133	Intermediate Similarity	NPC18904
0.8133	Intermediate Similarity	NPC30550
0.8133	Intermediate Similarity	NPC57380
0.8133	Intermediate Similarity	NPC277510
0.8133	Intermediate Similarity	NPC112757
0.8129	Intermediate Similarity	NPC19545
0.8129	Intermediate Similarity	NPC135325
0.8125	Intermediate Similarity	NPC476350
0.8125	Intermediate Similarity	NPC476349
0.8125	Intermediate Similarity	NPC244750
0.8125	Intermediate Similarity	NPC472877
0.8117	Intermediate Similarity	NPC300540
0.8117	Intermediate Similarity	NPC471346
0.8117	Intermediate Similarity	NPC250331
0.8117	Intermediate Similarity	NPC210826
0.8113	Intermediate Similarity	NPC472461
0.8113	Intermediate Similarity	NPC137100
0.8112	Intermediate Similarity	NPC231774
0.811	Intermediate Similarity	NPC44602
0.8108	Intermediate Similarity	NPC80035
0.8105	Intermediate Similarity	NPC225884
0.8105	Intermediate Similarity	NPC302181
0.8101	Intermediate Similarity	NPC208806
0.8101	Intermediate Similarity	NPC213608
0.8101	Intermediate Similarity	NPC183874
0.8101	Intermediate Similarity	NPC1477
0.8101	Intermediate Similarity	NPC84721
0.8101	Intermediate Similarity	NPC189130
0.8098	Intermediate Similarity	NPC136641
0.8098	Intermediate Similarity	NPC472784
0.8095	Intermediate Similarity	NPC5671
0.8095	Intermediate Similarity	NPC77179
0.8095	Intermediate Similarity	NPC263817
0.8095	Intermediate Similarity	NPC254603
0.8095	Intermediate Similarity	NPC23553
0.8092	Intermediate Similarity	NPC310128
0.8092	Intermediate Similarity	NPC49108

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 NPC252208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	982
0.2-0.3	1491
0.3-0.4	2669
0.4-0.5	1996
0.5-0.6	1076
0.6-0.7	436
0.7-0.8	120
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9357	High Similarity	NPD1471	Phase 3
0.8819	High Similarity	NPD2344	Approved
0.8581	High Similarity	NPD2309	Approved
0.8431	Intermediate Similarity	NPD3226	Approved
0.8311	Intermediate Similarity	NPD2346	Discontinued
0.7937	Intermediate Similarity	NPD2296	Approved
0.7935	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2799	Discontinued
0.7917	Intermediate Similarity	NPD1470	Approved
0.7891	Intermediate Similarity	NPD2313	Discontinued
0.7888	Intermediate Similarity	NPD3882	Suspended
0.784	Intermediate Similarity	NPD3749	Approved
0.7829	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1247	Approved
0.7771	Intermediate Similarity	NPD1512	Approved
0.7763	Intermediate Similarity	NPD2935	Discontinued
0.7727	Intermediate Similarity	NPD2800	Approved
0.7697	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1607	Approved
0.7671	Intermediate Similarity	NPD1203	Approved
0.7667	Intermediate Similarity	NPD1240	Approved
0.7662	Intermediate Similarity	NPD1549	Phase 2
0.7654	Intermediate Similarity	NPD7819	Suspended
0.7643	Intermediate Similarity	NPD1511	Approved
0.7639	Intermediate Similarity	NPD1201	Approved
0.7613	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD3926	Phase 2
0.7597	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2534	Approved
0.7595	Intermediate Similarity	NPD2533	Approved
0.7595	Intermediate Similarity	NPD2532	Approved
0.7589	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1510	Phase 2
0.7548	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD1243	Approved
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD6280	Approved
0.7485	Intermediate Similarity	NPD1934	Approved
0.7485	Intermediate Similarity	NPD6959	Discontinued
0.7485	Intermediate Similarity	NPD6279	Approved
0.7484	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1876	Approved
0.7471	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD919	Approved
0.7469	Intermediate Similarity	NPD6599	Discontinued
0.7466	Intermediate Similarity	NPD9717	Approved
0.7452	Intermediate Similarity	NPD3750	Approved
0.744	Intermediate Similarity	NPD6232	Discontinued
0.744	Intermediate Similarity	NPD6808	Phase 2
0.7439	Intermediate Similarity	NPD2801	Approved
0.7439	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7411	Suspended
0.7421	Intermediate Similarity	NPD6799	Approved
0.7417	Intermediate Similarity	NPD3268	Approved
0.7417	Intermediate Similarity	NPD411	Approved
0.7412	Intermediate Similarity	NPD7473	Discontinued
0.7375	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3972	Approved
0.7347	Intermediate Similarity	NPD1608	Approved
0.7321	Intermediate Similarity	NPD5494	Approved
0.732	Intermediate Similarity	NPD4060	Phase 1
0.7318	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2796	Approved
0.7308	Intermediate Similarity	NPD1551	Phase 2
0.7303	Intermediate Similarity	NPD3764	Approved
0.7299	Intermediate Similarity	NPD6559	Discontinued
0.7289	Intermediate Similarity	NPD3817	Phase 2
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD3818	Discontinued
0.7262	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4380	Phase 2
0.7251	Intermediate Similarity	NPD6166	Phase 2
0.7251	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1283	Approved
0.7244	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4308	Phase 3
0.7233	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD6273	Approved
0.7208	Intermediate Similarity	NPD943	Approved
0.72	Intermediate Similarity	NPD3267	Approved
0.72	Intermediate Similarity	NPD3266	Approved
0.7195	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1651	Approved
0.7188	Intermediate Similarity	NPD2354	Approved
0.7186	Intermediate Similarity	NPD5402	Approved
0.7171	Intermediate Similarity	NPD6832	Phase 2
0.7168	Intermediate Similarity	NPD3751	Discontinued
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD17	Approved
0.7134	Intermediate Similarity	NPD3748	Approved
0.7126	Intermediate Similarity	NPD5761	Phase 2
0.7126	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5760	Phase 2
0.7126	Intermediate Similarity	NPD1465	Phase 2
0.7125	Intermediate Similarity	NPD7003	Approved
0.7101	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7390	Discontinued
0.7089	Intermediate Similarity	NPD6100	Approved
0.7089	Intermediate Similarity	NPD6099	Approved
0.7086	Intermediate Similarity	NPD2797	Approved
0.7083	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6844	Discontinued
0.7047	Intermediate Similarity	NPD1611	Approved
0.7047	Intermediate Similarity	NPD1281	Approved
0.7045	Intermediate Similarity	NPD6797	Phase 2
0.7044	Intermediate Similarity	NPD2353	Approved
0.7044	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7768	Phase 2
0.7037	Intermediate Similarity	NPD3300	Phase 2
0.7035	Intermediate Similarity	NPD5711	Approved
0.7035	Intermediate Similarity	NPD5710	Approved
0.7033	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5844	Phase 1
0.7025	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8313	Approved
0.7022	Intermediate Similarity	NPD8312	Approved
0.7019	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1241	Discontinued
0.7012	Intermediate Similarity	NPD5049	Phase 3
0.7006	Intermediate Similarity	NPD6765	Approved
0.7006	Intermediate Similarity	NPD6764	Approved
0.7006	Intermediate Similarity	NPD7251	Discontinued
0.7	Intermediate Similarity	NPD1481	Phase 2
0.6993	Remote Similarity	NPD9494	Approved
0.6988	Remote Similarity	NPD7458	Discontinued
0.6987	Remote Similarity	NPD4307	Phase 2
0.6986	Remote Similarity	NPD9493	Approved
0.6981	Remote Similarity	NPD5404	Approved
0.6981	Remote Similarity	NPD5405	Approved
0.6981	Remote Similarity	NPD5406	Approved
0.6981	Remote Similarity	NPD5408	Approved
0.6974	Remote Similarity	NPD1164	Approved
0.697	Remote Similarity	NPD5403	Approved
0.6968	Remote Similarity	NPD6798	Discontinued
0.6966	Remote Similarity	NPD7808	Phase 3
0.6966	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6782	Approved
0.6952	Remote Similarity	NPD6776	Approved
0.6952	Remote Similarity	NPD6780	Approved
0.6952	Remote Similarity	NPD6781	Approved
0.6952	Remote Similarity	NPD6778	Approved
0.6952	Remote Similarity	NPD6777	Approved
0.6952	Remote Similarity	NPD6779	Approved
0.6951	Remote Similarity	NPD5401	Approved
0.6949	Remote Similarity	NPD5953	Discontinued
0.6941	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1535	Discovery
0.6931	Remote Similarity	NPD7435	Discontinued
0.6928	Remote Similarity	NPD1019	Discontinued
0.6923	Remote Similarity	NPD4287	Approved
0.6923	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8032	Phase 2
0.6914	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4626	Approved
0.6903	Remote Similarity	NPD7095	Approved
0.6893	Remote Similarity	NPD7074	Phase 3
0.6879	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4476	Approved
0.6875	Remote Similarity	NPD2163	Approved
0.6875	Remote Similarity	NPD7177	Discontinued
0.6875	Remote Similarity	NPD4477	Approved
0.6872	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3887	Approved
0.6862	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2403	Approved
0.6854	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6785	Approved
0.6851	Remote Similarity	NPD6784	Approved
0.6848	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7696	Phase 3
0.6842	Remote Similarity	NPD7698	Approved
0.6842	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7697	Approved
0.6839	Remote Similarity	NPD3787	Discontinued
0.6836	Remote Similarity	NPD7286	Phase 2
0.6836	Remote Similarity	NPD7054	Approved
0.6835	Remote Similarity	NPD1933	Approved
0.6832	Remote Similarity	NPD5762	Approved
0.6832	Remote Similarity	NPD5763	Approved
0.6821	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8150	Discontinued
0.6813	Remote Similarity	NPD7033	Discontinued
0.6806	Remote Similarity	NPD7871	Phase 2

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