NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.08
Volume:	250.242
LogP:	3.995
LogD:	3.225
LogS:	-3.656
# Rotatable Bonds:	1
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	2.192
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:	-4.892
MDCK Permeability:	1.399342727381736e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.957
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	98.90034484863281%
Volume Distribution (VD):	0.876
Pgp-substrate:	1.6424610614776611%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.786
CYP2C19-inhibitor:	0.821
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.61
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.877
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.668
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	8.952
Half-life (T1/2):	0.626

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.797
AMES Toxicity:	0.199
Rat Oral Acute Toxicity:	0.285
Maximum Recommended Daily Dose:	0.805
Skin Sensitization:	0.925
Carcinogencity:	0.196
Eye Corrosion:	0.055
Eye Irritation:	0.959
Respiratory Toxicity:	0.588

Download Data

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

Natural Product: NPC112757

Natural Product ID:	NPC112757
*Common Name:**	Stemofuran C
IUPAC Name:	5-(1-benzofuran-2-yl)-2-methylbenzene-1,3-diol
Synonyms:	Stemofuran C
Standard InCHIKey:	UJNBNDIUQWFUNM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O3/c1-9-12(16)6-11(7-13(9)17)15-8-10-4-2-3-5-14(10)18-15/h2-8,16-17H,1H3
SMILES:	Cc1c(O)cc(cc1O)c1cc2c(o1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462853
PubChem CID:	641365
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	slowly dried tubers	Bangkok, Thailand	n.a.	PMID[15679323]
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]
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	6

Activity Type	# Activity
Organism	15
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3821	Organism	Alternaria citri	Alternaria citri	EC50	=	7.0	ug.mL-1	PMID[567770]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC50	=	21.0	ug.mL-1	PMID[567770]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	3.2	ug.mL-1	PMID[567770]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	EC50	=	29.0	ug.mL-1	PMID[567770]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC50	=	8.0	ug.mL-1	PMID[567770]
NPT3821	Organism	Alternaria citri	Alternaria citri	EC90	=	528.0	ug ml-1	PMID[567770]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	EC90	>	200.0	ug ml-1	PMID[567770]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	30.0	ug ml-1	PMID[567770]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	EC90	>	200.0	ug ml-1	PMID[567770]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC90	>	200.0	ug ml-1	PMID[567770]
NPT3821	Organism	Alternaria citri	Alternaria citri	MIC	>	200.0	ug.mL-1	PMID[567770]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	MIC	>	200.0	ug.mL-1	PMID[567770]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	50.0	ug.mL-1	PMID[567770]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	>	200.0	ug.mL-1	PMID[567770]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	>	200.0	ug.mL-1	PMID[567770]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[567771]
NPT2	Others	Unspecified		Inhibition	=	10.0	%	PMID[567771]

☑ 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 NPC112757 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	453
0.1-0.2	1915
0.2-0.3	4694
0.3-0.4	12435
0.4-0.5	5248
0.5-0.6	4243
0.6-0.7	6619
0.7-0.8	6189
0.8-0.85	811
0.85-0.9	82
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC150215
0.9286	High Similarity	NPC98926
0.9231	High Similarity	NPC13282
0.9231	High Similarity	NPC167576
0.9167	High Similarity	NPC149085
0.9149	High Similarity	NPC155144
0.9041	High Similarity	NPC72370
0.9021	High Similarity	NPC17816
0.8966	High Similarity	NPC78335
0.8966	High Similarity	NPC230713
0.8904	High Similarity	NPC23668
0.8904	High Similarity	NPC193976
0.8904	High Similarity	NPC170169
0.8904	High Similarity	NPC115324
0.8897	High Similarity	NPC178202
0.8873	High Similarity	NPC53192
0.8859	High Similarity	NPC164110
0.8859	High Similarity	NPC96342
0.8859	High Similarity	NPC212967
0.8859	High Similarity	NPC246647
0.8844	High Similarity	NPC142308
0.8844	High Similarity	NPC207624
0.8811	High Similarity	NPC225884
0.8811	High Similarity	NPC302181
0.88	High Similarity	NPC226287
0.8792	High Similarity	NPC180924
0.8792	High Similarity	NPC137100
0.8784	High Similarity	NPC472462
0.8784	High Similarity	NPC235333
0.8776	High Similarity	NPC58668
0.8776	High Similarity	NPC106372
0.8767	High Similarity	NPC37226
0.8767	High Similarity	NPC226644
0.875	High Similarity	NPC230943
0.8732	High Similarity	NPC145673
0.8725	High Similarity	NPC198490
0.8725	High Similarity	NPC297531
0.8725	High Similarity	NPC213936
0.8725	High Similarity	NPC148938
0.8725	High Similarity	NPC99199
0.8723	High Similarity	NPC18457
0.869	High Similarity	NPC300267
0.869	High Similarity	NPC210826
0.869	High Similarity	NPC51641
0.8675	High Similarity	NPC472877
0.8658	High Similarity	NPC183874
0.8643	High Similarity	NPC163029
0.863	High Similarity	NPC12148
0.863	High Similarity	NPC130581
0.8621	High Similarity	NPC469764
0.8611	High Similarity	NPC1534
0.8609	High Similarity	NPC268360
0.8591	High Similarity	NPC67654
0.8591	High Similarity	NPC253872
0.8591	High Similarity	NPC125300
0.8571	High Similarity	NPC135325
0.8571	High Similarity	NPC272194
0.8571	High Similarity	NPC159508
0.8562	High Similarity	NPC469758
0.8553	High Similarity	NPC16935
0.8543	High Similarity	NPC472461
0.8543	High Similarity	NPC45131
0.8533	High Similarity	NPC158261
0.8533	High Similarity	NPC213608
0.8533	High Similarity	NPC42458
0.8533	High Similarity	NPC1477
0.8523	High Similarity	NPC116604
0.8523	High Similarity	NPC156244
0.8521	High Similarity	NPC62735
0.8516	High Similarity	NPC169471
0.8514	High Similarity	NPC221868
0.8514	High Similarity	NPC37208
0.8514	High Similarity	NPC70764
0.8514	High Similarity	NPC39929
0.8514	High Similarity	NPC296030
0.8503	High Similarity	NPC77903
0.8503	High Similarity	NPC71055
0.8503	High Similarity	NPC17101
0.85	High Similarity	NPC265793
0.8483	Intermediate Similarity	NPC169479
0.8483	Intermediate Similarity	NPC159855
0.8472	Intermediate Similarity	NPC28337
0.8467	Intermediate Similarity	NPC263676
0.8467	Intermediate Similarity	NPC5871
0.8467	Intermediate Similarity	NPC41326
0.8462	Intermediate Similarity	NPC268691
0.8451	Intermediate Similarity	NPC130976
0.8446	Intermediate Similarity	NPC5537
0.8442	Intermediate Similarity	NPC188486
0.8435	Intermediate Similarity	NPC196114
0.8435	Intermediate Similarity	NPC130176
0.8435	Intermediate Similarity	NPC99454
0.8431	Intermediate Similarity	NPC196879
0.8421	Intermediate Similarity	NPC247677
0.8421	Intermediate Similarity	NPC160015
0.8414	Intermediate Similarity	NPC18714
0.8414	Intermediate Similarity	NPC103752
0.8408	Intermediate Similarity	NPC286230
0.8408	Intermediate Similarity	NPC253730
0.8406	Intermediate Similarity	NPC197425
0.8403	Intermediate Similarity	NPC109232
0.84	Intermediate Similarity	NPC39819
0.84	Intermediate Similarity	NPC258249
0.8392	Intermediate Similarity	NPC98395
0.8392	Intermediate Similarity	NPC228661
0.8387	Intermediate Similarity	NPC84515
0.8387	Intermediate Similarity	NPC272722
0.8387	Intermediate Similarity	NPC312056
0.8387	Intermediate Similarity	NPC193998
0.838	Intermediate Similarity	NPC223616
0.8378	Intermediate Similarity	NPC46941
0.8377	Intermediate Similarity	NPC304839
0.8377	Intermediate Similarity	NPC220582
0.8369	Intermediate Similarity	NPC274876
0.8367	Intermediate Similarity	NPC131766
0.8366	Intermediate Similarity	NPC65504
0.8366	Intermediate Similarity	NPC260902
0.8366	Intermediate Similarity	NPC296957
0.8346	Intermediate Similarity	NPC246214
0.8345	Intermediate Similarity	NPC39753
0.8345	Intermediate Similarity	NPC278787
0.8345	Intermediate Similarity	NPC115998
0.8344	Intermediate Similarity	NPC75069
0.8333	Intermediate Similarity	NPC263092
0.8333	Intermediate Similarity	NPC475717
0.8333	Intermediate Similarity	NPC1755
0.8333	Intermediate Similarity	NPC39305
0.8333	Intermediate Similarity	NPC1706
0.8333	Intermediate Similarity	NPC59295
0.8323	Intermediate Similarity	NPC45124
0.8323	Intermediate Similarity	NPC304387
0.8323	Intermediate Similarity	NPC74854
0.8323	Intermediate Similarity	NPC30655
0.8323	Intermediate Similarity	NPC24761
0.8322	Intermediate Similarity	NPC37135
0.8322	Intermediate Similarity	NPC186397
0.8312	Intermediate Similarity	NPC476350
0.8312	Intermediate Similarity	NPC244750
0.8312	Intermediate Similarity	NPC476349
0.8312	Intermediate Similarity	NPC40583
0.8311	Intermediate Similarity	NPC308799
0.8311	Intermediate Similarity	NPC209278
0.8302	Intermediate Similarity	NPC476641
0.8301	Intermediate Similarity	NPC13879
0.8299	Intermediate Similarity	NPC59551
0.8298	Intermediate Similarity	NPC128216
0.8291	Intermediate Similarity	NPC470704
0.8289	Intermediate Similarity	NPC122365
0.8286	Intermediate Similarity	NPC137264
0.8286	Intermediate Similarity	NPC141549
0.828	Intermediate Similarity	NPC36320
0.8276	Intermediate Similarity	NPC137009
0.8273	Intermediate Similarity	NPC187907
0.8269	Intermediate Similarity	NPC238995
0.8267	Intermediate Similarity	NPC317492
0.8267	Intermediate Similarity	NPC200221
0.8267	Intermediate Similarity	NPC269420
0.8267	Intermediate Similarity	NPC294502
0.8267	Intermediate Similarity	NPC266499
0.8267	Intermediate Similarity	NPC223988
0.8267	Intermediate Similarity	NPC474052
0.8264	Intermediate Similarity	NPC254841
0.8258	Intermediate Similarity	NPC260296
0.8258	Intermediate Similarity	NPC115432
0.8255	Intermediate Similarity	NPC198427
0.8255	Intermediate Similarity	NPC14875
0.8255	Intermediate Similarity	NPC123202
0.8255	Intermediate Similarity	NPC7943
0.8255	Intermediate Similarity	NPC61284
0.8255	Intermediate Similarity	NPC113428
0.8255	Intermediate Similarity	NPC22005
0.8252	Intermediate Similarity	NPC239495
0.8252	Intermediate Similarity	NPC9985
0.825	Intermediate Similarity	NPC230619
0.825	Intermediate Similarity	NPC54098
0.8243	Intermediate Similarity	NPC184649
0.8243	Intermediate Similarity	NPC303185
0.8239	Intermediate Similarity	NPC57601
0.8231	Intermediate Similarity	NPC158871
0.8231	Intermediate Similarity	NPC471520
0.8231	Intermediate Similarity	NPC73028
0.8231	Intermediate Similarity	NPC313036
0.8228	Intermediate Similarity	NPC277480
0.8228	Intermediate Similarity	NPC53640
0.8227	Intermediate Similarity	NPC112192
0.8227	Intermediate Similarity	NPC164236
0.8227	Intermediate Similarity	NPC113006
0.8227	Intermediate Similarity	NPC128348
0.8227	Intermediate Similarity	NPC313618
0.8227	Intermediate Similarity	NPC66384
0.8227	Intermediate Similarity	NPC189106
0.8227	Intermediate Similarity	NPC309717
0.8224	Intermediate Similarity	NPC130015
0.8224	Intermediate Similarity	NPC473967
0.8224	Intermediate Similarity	NPC281272
0.8224	Intermediate Similarity	NPC38361
0.8219	Intermediate Similarity	NPC275734
0.8219	Intermediate Similarity	NPC182421
0.8217	Intermediate Similarity	NPC110257
0.8217	Intermediate Similarity	NPC133065

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 NPC112757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	1014
0.2-0.3	1420
0.3-0.4	2755
0.4-0.5	1849
0.5-0.6	1166
0.6-0.7	372
0.7-0.8	130
0.8-0.85	19
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8392	Intermediate Similarity	NPD2344	Approved
0.8369	Intermediate Similarity	NPD1607	Approved
0.8227	Intermediate Similarity	NPD1240	Approved
0.8194	Intermediate Similarity	NPD1551	Phase 2
0.8163	Intermediate Similarity	NPD2309	Approved
0.8138	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3749	Approved
0.8095	Intermediate Similarity	NPD3750	Approved
0.8086	Intermediate Similarity	NPD6559	Discontinued
0.8082	Intermediate Similarity	NPD1549	Phase 2
0.8054	Intermediate Similarity	NPD1511	Approved
0.8027	Intermediate Similarity	NPD1243	Approved
0.8014	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7949	Intermediate Similarity	NPD3882	Suspended
0.7947	Intermediate Similarity	NPD1512	Approved
0.7945	Intermediate Similarity	NPD6099	Approved
0.7945	Intermediate Similarity	NPD6100	Approved
0.7895	Intermediate Similarity	NPD920	Approved
0.7891	Intermediate Similarity	NPD2346	Discontinued
0.7881	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4308	Phase 3
0.7871	Intermediate Similarity	NPD1934	Approved
0.7857	Intermediate Similarity	NPD1203	Approved
0.7852	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2796	Approved
0.7821	Intermediate Similarity	NPD2801	Approved
0.7821	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3226	Approved
0.7785	Intermediate Similarity	NPD2800	Approved
0.7762	Intermediate Similarity	NPD4625	Phase 3
0.7755	Intermediate Similarity	NPD3748	Approved
0.775	Intermediate Similarity	NPD6959	Discontinued
0.7748	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD411	Approved
0.7708	Intermediate Similarity	NPD2313	Discontinued
0.7703	Intermediate Similarity	NPD2935	Discontinued
0.7671	Intermediate Similarity	NPD447	Suspended
0.7654	Intermediate Similarity	NPD3926	Phase 2
0.7647	Intermediate Similarity	NPD2534	Approved
0.7647	Intermediate Similarity	NPD2533	Approved
0.7647	Intermediate Similarity	NPD2532	Approved
0.7643	Intermediate Similarity	NPD9717	Approved
0.7643	Intermediate Similarity	NPD1608	Approved
0.764	Intermediate Similarity	NPD1247	Approved
0.7635	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3818	Discontinued
0.7616	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7768	Phase 2
0.7606	Intermediate Similarity	NPD2797	Approved
0.7603	Intermediate Similarity	NPD4307	Phase 2
0.7603	Intermediate Similarity	NPD943	Approved
0.76	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1465	Phase 2
0.7595	Intermediate Similarity	NPD7819	Suspended
0.7593	Intermediate Similarity	NPD6232	Discontinued
0.7589	Intermediate Similarity	NPD4749	Approved
0.758	Intermediate Similarity	NPD7411	Suspended
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7571	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD422	Phase 1
0.7564	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7473	Discontinued
0.755	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2296	Approved
0.7547	Intermediate Similarity	NPD5402	Approved
0.7533	Intermediate Similarity	NPD1471	Phase 3
0.7532	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD919	Approved
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1470	Approved
0.7469	Intermediate Similarity	NPD5494	Approved
0.7468	Intermediate Similarity	NPD6799	Approved
0.7466	Intermediate Similarity	NPD3268	Approved
0.7466	Intermediate Similarity	NPD3764	Approved
0.7466	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.7448	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1201	Approved
0.7447	Intermediate Similarity	NPD1610	Phase 2
0.7432	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD2798	Approved
0.7429	Intermediate Similarity	NPD17	Approved
0.741	Intermediate Similarity	NPD1548	Phase 1
0.7394	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4628	Phase 3
0.7379	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7390	Discontinued
0.7329	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6832	Phase 2
0.7329	Intermediate Similarity	NPD4908	Phase 1
0.7329	Intermediate Similarity	NPD3817	Phase 2
0.7325	Intermediate Similarity	NPD5403	Approved
0.7325	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD230	Phase 1
0.7308	Intermediate Similarity	NPD5401	Approved
0.7299	Intermediate Similarity	NPD1241	Discontinued
0.7292	Intermediate Similarity	NPD1283	Approved
0.7278	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD3972	Approved
0.7266	Intermediate Similarity	NPD9493	Approved
0.7248	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1613	Approved
0.7241	Intermediate Similarity	NPD3267	Approved
0.7241	Intermediate Similarity	NPD3266	Approved
0.7235	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1651	Approved
0.723	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7074	Phase 3
0.7215	Intermediate Similarity	NPD3873	Phase 3
0.7215	Intermediate Similarity	NPD3869	Phase 3
0.7205	Intermediate Similarity	NPD6801	Discontinued
0.7194	Intermediate Similarity	NPD6671	Approved
0.7186	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1778	Approved
0.7172	Intermediate Similarity	NPD3225	Approved
0.7172	Intermediate Similarity	NPD1876	Approved
0.7169	Intermediate Similarity	NPD7229	Phase 3
0.716	Intermediate Similarity	NPD7054	Approved
0.7153	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4287	Approved
0.7124	Intermediate Similarity	NPD5405	Approved
0.7124	Intermediate Similarity	NPD5406	Approved
0.7124	Intermediate Similarity	NPD5404	Approved
0.7124	Intermediate Similarity	NPD5408	Approved
0.7118	Intermediate Similarity	NPD7472	Approved
0.7117	Intermediate Similarity	NPD4288	Approved
0.7114	Intermediate Similarity	NPD1296	Phase 2
0.7101	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6280	Approved
0.7099	Intermediate Similarity	NPD6279	Approved
0.7083	Intermediate Similarity	NPD1611	Approved
0.7083	Intermediate Similarity	NPD1281	Approved
0.7083	Intermediate Similarity	NPD1535	Discovery
0.7076	Intermediate Similarity	NPD6797	Phase 2
0.7076	Intermediate Similarity	NPD5953	Discontinued
0.7075	Intermediate Similarity	NPD1019	Discontinued
0.7066	Intermediate Similarity	NPD5710	Approved
0.7066	Intermediate Similarity	NPD5711	Approved
0.7059	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7286	Phase 2
0.7059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6696	Suspended
0.7052	Intermediate Similarity	NPD8313	Approved
0.7052	Intermediate Similarity	NPD8312	Approved
0.7048	Intermediate Similarity	NPD6746	Phase 2
0.7044	Intermediate Similarity	NPD6273	Approved
0.7042	Intermediate Similarity	NPD9545	Approved
0.7035	Intermediate Similarity	NPD7251	Discontinued
0.703	Intermediate Similarity	NPD6971	Discontinued
0.7027	Intermediate Similarity	NPD9494	Approved
0.7027	Intermediate Similarity	NPD2861	Phase 2
0.7025	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1164	Approved
0.7007	Intermediate Similarity	NPD4750	Phase 3
0.7	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7177	Discontinued
0.6994	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD37	Approved
0.6994	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7808	Phase 3
0.6994	Remote Similarity	NPD6844	Discontinued
0.6988	Remote Similarity	NPD6234	Discontinued
0.6974	Remote Similarity	NPD1933	Approved
0.697	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4967	Phase 2
0.697	Remote Similarity	NPD4966	Approved
0.697	Remote Similarity	NPD4965	Approved
0.6959	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5761	Phase 2
0.6951	Remote Similarity	NPD5760	Phase 2
0.6948	Remote Similarity	NPD7033	Discontinued
0.6946	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3027	Phase 3
0.6932	Remote Similarity	NPD8434	Phase 2
0.6928	Remote Similarity	NPD6651	Approved
0.6919	Remote Similarity	NPD1729	Discontinued
0.6918	Remote Similarity	NPD9269	Phase 2
0.6912	Remote Similarity	NPD968	Approved
0.6905	Remote Similarity	NPD7199	Phase 2
0.6901	Remote Similarity	NPD3751	Discontinued
0.6897	Remote Similarity	NPD3496	Discontinued
0.6887	Remote Similarity	NPD1699	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