NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	259.033
LogP:	3.812
LogD:	3.191
LogS:	-3.699
# Rotatable Bonds:	2
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	2.231
Fsp3:	0.067
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:	-4.875
MDCK Permeability:	1.2843519471061882e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.889
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	98.63815307617188%
Volume Distribution (VD):	0.728
Pgp-substrate:	2.6045095920562744%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.86
CYP2C19-inhibitor:	0.862
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.608
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.923
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	9.403
Half-life (T1/2):	0.702

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.092
Drug-inuced Liver Injury (DILI):	0.793
AMES Toxicity:	0.261
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.921
Carcinogencity:	0.11
Eye Corrosion:	0.016
Eye Irritation:	0.956
Respiratory Toxicity:	0.63

Download Data

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

Natural Product: NPC98926

Natural Product ID:	NPC98926
*Common Name:**	Stemofuran B
IUPAC Name:	2-(3-hydroxy-5-methoxyphenyl)-1-benzofuran-4-ol
Synonyms:
Standard InCHIKey:	LNYJPSJEXBTRPO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O4/c1-18-11-6-9(5-10(16)7-11)15-8-12-13(17)3-2-4-14(12)19-15/h2-8,16-17H,1H3
SMILES:	COc1cc(O)cc(c1)c1cc2c(o1)cccc2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511197
PubChem CID:	641364
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	Leaves, rhizomes, and roots	southeast Thailand near Chonburi	2000-Feb, 2001-Jan	PMID[12088422]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	Southeast Thailand near Chonburi, Khao Khieo, close to the Chanthathen waterfall and Sri Racha	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	slowly dried tubers	Bangkok, Thailand	n.a.	PMID[15679323]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	root	n.a.	PMID[21902195]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30254	Stemona collinsae	Species	Stemonaceae	Eukaryota	leaf and root	n.a.	n.a.	Database[Title]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	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	1
MIC	5
Others	5

Activity Type	# Activity
Organism	15
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3821	Organism	Alternaria citri	Alternaria citri	EC50	=	5.0	ug.mL-1	PMID[473132]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC50	=	10.0	ug.mL-1	PMID[473132]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	1.4	ug.mL-1	PMID[473132]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	EC50	=	8.0	ug.mL-1	PMID[473132]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC50	=	183.0	ug.mL-1	PMID[473132]
NPT3821	Organism	Alternaria citri	Alternaria citri	EC90	=	128.0	ug ml-1	PMID[473132]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC90	>	200.0	ug ml-1	PMID[473132]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	52.0	ug ml-1	PMID[473132]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	EC90	>	200.0	ug ml-1	PMID[473132]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC90	>	200.0	ug ml-1	PMID[473132]
NPT3821	Organism	Alternaria citri	Alternaria citri	MIC	=	200.0	ug.mL-1	PMID[473132]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	MIC	>	200.0	ug.mL-1	PMID[473132]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	50.0	ug.mL-1	PMID[473132]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	>	200.0	ug.mL-1	PMID[473132]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	>	200.0	ug.mL-1	PMID[473132]
NPT2	Others	Unspecified		IC50	=	23300.0	nM	PMID[473133]

☑ 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 NPC98926 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	464
0.1-0.2	1917
0.2-0.3	4681
0.3-0.4	11398
0.4-0.5	6350
0.5-0.6	4184
0.6-0.7	5722
0.7-0.8	4883
0.8-0.85	2120
0.85-0.9	878
0.9-0.95	95
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9716	High Similarity	NPC17816
0.9714	High Similarity	NPC155144
0.9583	High Similarity	NPC115324
0.9583	High Similarity	NPC170169
0.9571	High Similarity	NPC53192
0.9517	High Similarity	NPC207624
0.9514	High Similarity	NPC230713
0.9514	High Similarity	NPC78335
0.9514	High Similarity	NPC167576
0.9504	High Similarity	NPC302181
0.9448	High Similarity	NPC193976
0.9448	High Similarity	NPC23668
0.9448	High Similarity	NPC106372
0.9448	High Similarity	NPC58668
0.9444	High Similarity	NPC178202
0.9444	High Similarity	NPC226644
0.9444	High Similarity	NPC37226
0.9437	High Similarity	NPC230943
0.9388	High Similarity	NPC148938
0.9388	High Similarity	NPC198490
0.9384	High Similarity	NPC142308
0.932	High Similarity	NPC183874
0.932	High Similarity	NPC472462
0.932	High Similarity	NPC72370
0.932	High Similarity	NPC235333
0.9306	High Similarity	NPC130581
0.9306	High Similarity	NPC12148
0.9286	High Similarity	NPC112757
0.9262	High Similarity	NPC246647
0.9262	High Similarity	NPC212967
0.9262	High Similarity	NPC164110
0.9262	High Similarity	NPC96342
0.9257	High Similarity	NPC297531
0.9257	High Similarity	NPC213936
0.9257	High Similarity	NPC99199
0.9252	High Similarity	NPC67654
0.9252	High Similarity	NPC253872
0.9241	High Similarity	NPC135325
0.9236	High Similarity	NPC210826
0.9236	High Similarity	NPC51641
0.9236	High Similarity	NPC300267
0.9231	High Similarity	NPC225884
0.92	High Similarity	NPC16935
0.9195	High Similarity	NPC45131
0.9195	High Similarity	NPC180924
0.9189	High Similarity	NPC1477
0.9189	High Similarity	NPC213608
0.9184	High Similarity	NPC156244
0.9178	High Similarity	NPC39929
0.9178	High Similarity	NPC296030
0.9155	High Similarity	NPC145673
0.9133	High Similarity	NPC268360
0.9122	High Similarity	NPC125300
0.9122	High Similarity	NPC263676
0.9122	High Similarity	NPC5871
0.9079	High Similarity	NPC188486
0.9073	High Similarity	NPC196879
0.9073	High Similarity	NPC472877
0.9067	High Similarity	NPC137100
0.9067	High Similarity	NPC247677
0.9067	High Similarity	NPC472461
0.9067	High Similarity	NPC160015
0.9054	High Similarity	NPC116604
0.9048	High Similarity	NPC37208
0.9048	High Similarity	NPC221868
0.9028	High Similarity	NPC159855
0.9028	High Similarity	NPC169479
0.902	High Similarity	NPC312056
0.902	High Similarity	NPC193998
0.902	High Similarity	NPC272722
0.902	High Similarity	NPC84515
0.9014	High Similarity	NPC18457
0.9013	High Similarity	NPC220582
0.9013	High Similarity	NPC304839
0.9007	High Similarity	NPC65504
0.9007	High Similarity	NPC260902
0.9007	High Similarity	NPC296957
0.8993	High Similarity	NPC41326
0.898	High Similarity	NPC272194
0.8961	High Similarity	NPC1706
0.8961	High Similarity	NPC1755
0.8961	High Similarity	NPC263092
0.8961	High Similarity	NPC39305
0.8961	High Similarity	NPC59295
0.8954	High Similarity	NPC30655
0.8954	High Similarity	NPC74854
0.8954	High Similarity	NPC45124
0.8954	High Similarity	NPC304387
0.8947	High Similarity	NPC476350
0.8947	High Similarity	NPC40583
0.8947	High Similarity	NPC476349
0.8933	High Similarity	NPC42458
0.8933	High Similarity	NPC122365
0.8933	High Similarity	NPC158261
0.8919	High Similarity	NPC317492
0.8919	High Similarity	NPC266499
0.8904	High Similarity	NPC184649
0.8904	High Similarity	NPC303185
0.8903	High Similarity	NPC36320
0.8897	High Similarity	NPC73028
0.8897	High Similarity	NPC1534
0.8896	High Similarity	NPC238995
0.8889	High Similarity	NPC28337
0.8889	High Similarity	NPC115432
0.8889	High Similarity	NPC182421
0.8889	High Similarity	NPC260296
0.8881	High Similarity	NPC124269
0.8873	High Similarity	NPC473391
0.8873	High Similarity	NPC472364
0.8867	High Similarity	NPC130015
0.8867	High Similarity	NPC38361
0.8859	High Similarity	NPC470107
0.8859	High Similarity	NPC13282
0.8851	High Similarity	NPC168085
0.8851	High Similarity	NPC216624
0.8851	High Similarity	NPC186397
0.8851	High Similarity	NPC37135
0.8846	High Similarity	NPC53640
0.8846	High Similarity	NPC277480
0.8844	High Similarity	NPC196114
0.8844	High Similarity	NPC299011
0.8844	High Similarity	NPC130176
0.8844	High Similarity	NPC99454
0.8839	High Similarity	NPC133065
0.8839	High Similarity	NPC159508
0.8839	High Similarity	NPC110257
0.8836	High Similarity	NPC113770
0.8828	High Similarity	NPC49108
0.8824	High Similarity	NPC244750
0.8819	High Similarity	NPC137009
0.8816	High Similarity	NPC13879
0.8811	High Similarity	NPC250266
0.8811	High Similarity	NPC212767
0.8811	High Similarity	NPC228661
0.8811	High Similarity	NPC254841
0.8811	High Similarity	NPC266597
0.8811	High Similarity	NPC188879
0.8803	High Similarity	NPC9985
0.8803	High Similarity	NPC239495
0.88	High Similarity	NPC149614
0.8792	High Similarity	NPC223988
0.879	High Similarity	NPC247973
0.879	High Similarity	NPC50394
0.8786	High Similarity	NPC313618
0.8784	High Similarity	NPC198427
0.8784	High Similarity	NPC150215
0.8784	High Similarity	NPC46941
0.8782	High Similarity	NPC169471
0.8782	High Similarity	NPC291110
0.8782	High Similarity	NPC45449
0.8782	High Similarity	NPC37183
0.8782	High Similarity	NPC38914
0.8782	High Similarity	NPC474591
0.8782	High Similarity	NPC39306
0.8776	High Similarity	NPC469764
0.8776	High Similarity	NPC234629
0.8776	High Similarity	NPC311741
0.8776	High Similarity	NPC71210
0.8776	High Similarity	NPC311144
0.8774	High Similarity	NPC219861
0.8767	High Similarity	NPC202981
0.8767	High Similarity	NPC310340
0.8767	High Similarity	NPC287722
0.8767	High Similarity	NPC471520
0.8759	High Similarity	NPC275734
0.8759	High Similarity	NPC269652
0.8759	High Similarity	NPC281207
0.875	High Similarity	NPC233776
0.875	High Similarity	NPC188947
0.875	High Similarity	NPC309154
0.875	High Similarity	NPC55162
0.875	High Similarity	NPC279668
0.875	High Similarity	NPC472460
0.875	High Similarity	NPC12175
0.875	High Similarity	NPC278323
0.875	High Similarity	NPC90665
0.875	High Similarity	NPC147686
0.875	High Similarity	NPC329225
0.875	High Similarity	NPC99333
0.875	High Similarity	NPC280284
0.8741	High Similarity	NPC194281
0.8741	High Similarity	NPC235428
0.8741	High Similarity	NPC127447
0.8741	High Similarity	NPC193792
0.8741	High Similarity	NPC234133
0.8741	High Similarity	NPC231772
0.8741	High Similarity	NPC87545
0.8741	High Similarity	NPC240593
0.8741	High Similarity	NPC29353
0.8741	High Similarity	NPC473887
0.8741	High Similarity	NPC124784
0.8741	High Similarity	NPC47815
0.8733	High Similarity	NPC472421
0.8733	High Similarity	NPC29231
0.8733	High Similarity	NPC62042
0.8733	High Similarity	NPC135303
0.8733	High Similarity	NPC295036
0.8733	High Similarity	NPC101957
0.8733	High Similarity	NPC120105
0.8733	High Similarity	NPC179183

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 NPC98926 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	985
0.2-0.3	1577
0.3-0.4	2710
0.4-0.5	1821
0.5-0.6	1133
0.6-0.7	320
0.7-0.8	128
0.8-0.85	33
0.85-0.9	14
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8786	High Similarity	NPD1240	Approved
0.875	High Similarity	NPD1549	Phase 2
0.8681	High Similarity	NPD1552	Clinical (unspecified phase)
0.8681	High Similarity	NPD1550	Clinical (unspecified phase)
0.8681	High Similarity	NPD2344	Approved
0.8671	High Similarity	NPD1510	Phase 2
0.8662	High Similarity	NPD1607	Approved
0.8649	High Similarity	NPD4378	Clinical (unspecified phase)
0.8636	High Similarity	NPD3749	Approved
0.8581	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD3882	Suspended
0.8533	High Similarity	NPD920	Approved
0.8497	Intermediate Similarity	NPD1934	Approved
0.8467	Intermediate Similarity	NPD1512	Approved
0.8446	Intermediate Similarity	NPD2309	Approved
0.8442	Intermediate Similarity	NPD2801	Approved
0.8442	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1243	Approved
0.84	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD2796	Approved
0.8356	Intermediate Similarity	NPD1551	Phase 2
0.8311	Intermediate Similarity	NPD2800	Approved
0.8267	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD3926	Phase 2
0.8243	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1247	Approved
0.8232	Intermediate Similarity	NPD6559	Discontinued
0.821	Intermediate Similarity	NPD3818	Discontinued
0.8205	Intermediate Similarity	NPD7819	Suspended
0.8194	Intermediate Similarity	NPD7411	Suspended
0.8153	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4380	Phase 2
0.8125	Intermediate Similarity	NPD6959	Discontinued
0.8113	Intermediate Similarity	NPD919	Approved
0.8092	Intermediate Similarity	NPD6799	Approved
0.8086	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6166	Phase 2
0.8086	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5494	Approved
0.805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7075	Discontinued
0.8039	Intermediate Similarity	NPD2533	Approved
0.8039	Intermediate Similarity	NPD2534	Approved
0.8039	Intermediate Similarity	NPD2532	Approved
0.8028	Intermediate Similarity	NPD1203	Approved
0.8014	Intermediate Similarity	NPD943	Approved
0.8013	Intermediate Similarity	NPD3750	Approved
0.8013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7768	Phase 2
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6232	Discontinued
0.7949	Intermediate Similarity	NPD3226	Approved
0.7933	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7473	Discontinued
0.7925	Intermediate Similarity	NPD3817	Phase 2
0.7925	Intermediate Similarity	NPD5402	Approved
0.7898	Intermediate Similarity	NPD6599	Discontinued
0.7877	Intermediate Similarity	NPD2313	Discontinued
0.7838	Intermediate Similarity	NPD447	Suspended
0.7829	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD9717	Approved
0.7815	Intermediate Similarity	NPD1471	Phase 3
0.7815	Intermediate Similarity	NPD2346	Discontinued
0.7812	Intermediate Similarity	NPD2296	Approved
0.78	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6801	Discontinued
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7755	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1465	Phase 2
0.7748	Intermediate Similarity	NPD6100	Approved
0.7748	Intermediate Similarity	NPD6099	Approved
0.7746	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7054	Approved
0.7718	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5403	Approved
0.7692	Intermediate Similarity	NPD5401	Approved
0.7692	Intermediate Similarity	NPD1608	Approved
0.7682	Intermediate Similarity	NPD3748	Approved
0.7682	Intermediate Similarity	NPD2799	Discontinued
0.7679	Intermediate Similarity	NPD7472	Approved
0.7635	Intermediate Similarity	NPD411	Approved
0.7633	Intermediate Similarity	NPD5953	Discontinued
0.7633	Intermediate Similarity	NPD6797	Phase 2
0.7619	Intermediate Similarity	NPD7286	Phase 2
0.7619	Intermediate Similarity	NPD5844	Phase 1
0.7619	Intermediate Similarity	NPD6832	Phase 2
0.7619	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD230	Phase 1
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7251	Discontinued
0.7586	Intermediate Similarity	NPD4287	Approved
0.758	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6651	Approved
0.7548	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7808	Phase 3
0.7544	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1470	Approved
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7483	Intermediate Similarity	NPD17	Approved
0.7483	Intermediate Similarity	NPD2798	Approved
0.7469	Intermediate Similarity	NPD6280	Approved
0.7469	Intermediate Similarity	NPD6279	Approved
0.7451	Intermediate Similarity	NPD7033	Discontinued
0.7451	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4308	Phase 3
0.7447	Intermediate Similarity	NPD9493	Approved
0.7436	Intermediate Similarity	NPD4628	Phase 3
0.7425	Intermediate Similarity	NPD5711	Approved
0.7425	Intermediate Similarity	NPD5710	Approved
0.7425	Intermediate Similarity	NPD7229	Phase 3
0.74	Intermediate Similarity	NPD3764	Approved
0.74	Intermediate Similarity	NPD3268	Approved
0.7383	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4908	Phase 1
0.7379	Intermediate Similarity	NPD1201	Approved
0.7379	Intermediate Similarity	NPD1610	Phase 2
0.7379	Intermediate Similarity	NPD422	Phase 1
0.7372	Intermediate Similarity	NPD2654	Approved
0.7368	Intermediate Similarity	NPD1729	Discontinued
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7353	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7343	Intermediate Similarity	NPD1548	Phase 1
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7326	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6808	Phase 2
0.7317	Intermediate Similarity	NPD5761	Phase 2
0.7317	Intermediate Similarity	NPD5760	Phase 2
0.7315	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1613	Approved
0.7297	Intermediate Similarity	NPD2797	Approved
0.7296	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7256	Intermediate Similarity	NPD6844	Discontinued
0.7255	Intermediate Similarity	NPD1933	Approved
0.7235	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3225	Approved
0.7222	Intermediate Similarity	NPD9545	Approved
0.7203	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8312	Approved
0.72	Intermediate Similarity	NPD8313	Approved
0.719	Intermediate Similarity	NPD4307	Phase 2
0.7184	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3267	Approved
0.7181	Intermediate Similarity	NPD3266	Approved
0.7162	Intermediate Similarity	NPD4749	Approved
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7135	Intermediate Similarity	NPD2403	Approved
0.7118	Intermediate Similarity	NPD3787	Discontinued
0.7113	Intermediate Similarity	NPD1241	Discontinued
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3972	Approved
0.7088	Intermediate Similarity	NPD4361	Phase 2
0.7088	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD9494	Approved
0.7083	Intermediate Similarity	NPD6971	Discontinued
0.7076	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5405	Approved
0.707	Intermediate Similarity	NPD5404	Approved
0.707	Intermediate Similarity	NPD5406	Approved
0.707	Intermediate Similarity	NPD5408	Approved
0.7067	Intermediate Similarity	NPD1164	Approved
0.7066	Intermediate Similarity	NPD4288	Approved
0.7059	Intermediate Similarity	NPD1296	Phase 2
0.7052	Intermediate Similarity	NPD7177	Discontinued
0.7033	Intermediate Similarity	NPD4363	Phase 3
0.7033	Intermediate Similarity	NPD4360	Phase 2
0.7027	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD1876	Approved
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3027	Phase 3
0.6988	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.698	Remote Similarity	NPD9269	Phase 2
0.698	Remote Similarity	NPD1481	Phase 2
0.6974	Remote Similarity	NPD2861	Phase 2
0.6964	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2163	Approved
0.6948	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD37	Approved
0.6941	Remote Similarity	NPD6234	Discontinued
0.6939	Remote Similarity	NPD9268	Approved
0.6933	Remote Similarity	NPD4662	Approved
0.6933	Remote Similarity	NPD4661	Approved
0.6923	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4965	Approved
0.6923	Remote Similarity	NPD4967	Phase 2
0.6918	Remote Similarity	NPD6003	Clinical (unspecified phase)

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