NPASS Compound

Structure

CID106372 OpenBabel06191715452D 22 24 0 0 0 0 0 0 0 0999 V2000 -1.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 20 1 0 0 0 0 3 21 1 0 0 0 0 4 10 2 0 0 0 0 4 12 1 0 0 0 0 5 10 1 0 0 0 0 5 14 2 0 0 0 0 6 11 2 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 16 2 0 0 0 0 8 13 1 0 0 0 0 8 17 2 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.1
Volume:	302.415
LogP:	4.242
LogD:	3.379
LogS:	-4.473
# Rotatable Bonds:	3
TPSA:	72.06
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.769
Synthetic Accessibility Score:	2.444
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.969
MDCK Permeability:	1.5045654436107725e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.554
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	0.819

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	98.41675567626953%
Volume Distribution (VD):	0.609
Pgp-substrate:	4.154958724975586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.754
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.59
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.803
CYP2D6-substrate:	0.946
CYP3A4-inhibitor:	0.754
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	9.167
Half-life (T1/2):	0.376

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.335
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.795
Carcinogencity:	0.031
Eye Corrosion:	0.007
Eye Irritation:	0.944
Respiratory Toxicity:	0.664

Download Data

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

Natural Product: NPC106372

Natural Product ID:	NPC106372
*Common Name:**	Stemofuran M
IUPAC Name:	2-(3-hydroxy-5-methoxy-2-methylphenyl)-6-methoxy-1-benzofuran-4-ol
Synonyms:	Stemofuran M
Standard InCHIKey:	SVJMXXOFWBJHRJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O5/c1-9-12(4-10(20-2)5-14(9)18)17-8-13-15(19)6-11(21-3)7-16(13)22-17/h4-8,18-19H,1-3H3
SMILES:	Cc1c(cc(cc1O)OC)c1cc2c(cc(cc2o1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1807146
PubChem CID:	50994475
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
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	Roots; Stems	n.a.	n.a.	PMID[19374387]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20415428]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	n.a.	root	n.a.	PMID[21126060]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	Roots	Lampang Province, Thailand	2009-APR	PMID[21126060]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21902195]
NPO10593	Aspergillus pulvinus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13984	Helenium radiatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9624	Myoporum bontioides	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO221	Stemona aphylla	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO866	Heliomeris longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28187	Duguetia confinis	Species	Annonaceae	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
MIC	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	125.0	ug.mL-1	PMID[515821]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	62.5	ug.mL-1	PMID[515821]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	31.3	ug.mL-1	PMID[515821]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	62.5	ug.mL-1	PMID[515821]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	31.3	ug.mL-1	PMID[515821]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	31.3	ug.mL-1	PMID[515821]

☑ 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 NPC106372 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	431
0.1-0.2	1876
0.2-0.3	4138
0.3-0.4	10527
0.4-0.5	7609
0.5-0.6	3733
0.6-0.7	5304
0.7-0.8	5161
0.8-0.85	2408
0.85-0.9	1363
0.9-0.95	127
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC58668
0.9931	High Similarity	NPC207624
0.9862	High Similarity	NPC193976
0.9862	High Similarity	NPC23668
0.9862	High Similarity	NPC115324
0.9796	High Similarity	NPC148938
0.9795	High Similarity	NPC142308
0.973	High Similarity	NPC180924
0.9728	High Similarity	NPC235333
0.9722	High Similarity	NPC17816
0.9664	High Similarity	NPC96342
0.9664	High Similarity	NPC164110
0.9664	High Similarity	NPC246647
0.9664	High Similarity	NPC212967
0.9662	High Similarity	NPC99199
0.9662	High Similarity	NPC213936
0.9662	High Similarity	NPC297531
0.9592	High Similarity	NPC170169
0.9589	High Similarity	NPC178202
0.9533	High Similarity	NPC268360
0.9524	High Similarity	NPC78335
0.9524	High Similarity	NPC230713
0.9524	High Similarity	NPC167576
0.9463	High Similarity	NPC183874
0.9456	High Similarity	NPC226644
0.9456	High Similarity	NPC37226
0.9448	High Similarity	NPC98926
0.9448	High Similarity	NPC155144
0.9448	High Similarity	NPC230943
0.94	High Similarity	NPC198490
0.9396	High Similarity	NPC5871
0.9388	High Similarity	NPC135325
0.9379	High Similarity	NPC302181
0.9351	High Similarity	NPC133065
0.9333	High Similarity	NPC472462
0.9333	High Similarity	NPC72370
0.9333	High Similarity	NPC213608
0.9333	High Similarity	NPC1477
0.932	High Similarity	NPC130581
0.932	High Similarity	NPC12148
0.931	High Similarity	NPC53192
0.929	High Similarity	NPC39306
0.9267	High Similarity	NPC67654
0.9262	High Similarity	NPC13282
0.9252	High Similarity	NPC210826
0.9252	High Similarity	NPC300267
0.9252	High Similarity	NPC51641
0.9241	High Similarity	NPC49108
0.9231	High Similarity	NPC53640
0.9211	High Similarity	NPC247677
0.9211	High Similarity	NPC160015
0.9211	High Similarity	NPC45131
0.9211	High Similarity	NPC137100
0.92	High Similarity	NPC156244
0.9195	High Similarity	NPC39929
0.9195	High Similarity	NPC296030
0.9178	High Similarity	NPC310340
0.9167	High Similarity	NPC474591
0.9161	High Similarity	NPC84515
0.9161	High Similarity	NPC312056
0.9156	High Similarity	NPC304839
0.9156	High Similarity	NPC220582
0.915	High Similarity	NPC260902
0.915	High Similarity	NPC65504
0.915	High Similarity	NPC296957
0.9139	High Similarity	NPC253872
0.9116	High Similarity	NPC225884
0.9097	High Similarity	NPC74854
0.9097	High Similarity	NPC188486
0.9097	High Similarity	NPC45124
0.9097	High Similarity	NPC30655
0.9091	High Similarity	NPC476349
0.9091	High Similarity	NPC476350
0.9091	High Similarity	NPC196879
0.9091	High Similarity	NPC40583
0.9091	High Similarity	NPC472877
0.9067	High Similarity	NPC288036
0.9067	High Similarity	NPC97028
0.9067	High Similarity	NPC97029
0.9067	High Similarity	NPC65775
0.9067	High Similarity	NPC100985
0.9067	High Similarity	NPC37208
0.9067	High Similarity	NPC158338
0.9067	High Similarity	NPC65589
0.9067	High Similarity	NPC221868
0.9067	High Similarity	NPC10027
0.906	High Similarity	NPC259632
0.906	High Similarity	NPC17101
0.906	High Similarity	NPC77903
0.9054	High Similarity	NPC134621
0.9045	High Similarity	NPC37183
0.9045	High Similarity	NPC291110
0.9041	High Similarity	NPC275734
0.9038	High Similarity	NPC272722
0.9038	High Similarity	NPC3448
0.9038	High Similarity	NPC477239
0.9032	High Similarity	NPC260296
0.9032	High Similarity	NPC115432
0.9013	High Similarity	NPC263676
0.9013	High Similarity	NPC154683
0.9013	High Similarity	NPC40356
0.9013	High Similarity	NPC125300
0.9013	High Similarity	NPC474843
0.9007	High Similarity	NPC227122
0.9007	High Similarity	NPC295036
0.9007	High Similarity	NPC470107
0.9	High Similarity	NPC172329
0.9	High Similarity	NPC7025
0.9	High Similarity	NPC2569
0.9	High Similarity	NPC216624
0.9	High Similarity	NPC27221
0.9	High Similarity	NPC272194
0.9	High Similarity	NPC256672
0.8994	High Similarity	NPC247136
0.8993	High Similarity	NPC237208
0.8993	High Similarity	NPC299011
0.8987	High Similarity	NPC277480
0.8986	High Similarity	NPC66404
0.8986	High Similarity	NPC95123
0.8981	High Similarity	NPC159508
0.898	High Similarity	NPC18714
0.8974	High Similarity	NPC96031
0.8968	High Similarity	NPC244750
0.8968	High Similarity	NPC16935
0.8954	High Similarity	NPC122365
0.8954	High Similarity	NPC303950
0.8947	High Similarity	NPC232645
0.8947	High Similarity	NPC474417
0.8947	High Similarity	NPC116604
0.8947	High Similarity	NPC258249
0.8947	High Similarity	NPC149526
0.8947	High Similarity	NPC72958
0.894	High Similarity	NPC266499
0.894	High Similarity	NPC317492
0.8933	High Similarity	NPC7943
0.8933	High Similarity	NPC123202
0.8933	High Similarity	NPC22005
0.8931	High Similarity	NPC247973
0.8931	High Similarity	NPC50394
0.8926	High Similarity	NPC29577
0.8926	High Similarity	NPC184649
0.8926	High Similarity	NPC303185
0.8926	High Similarity	NPC311144
0.8924	High Similarity	NPC45449
0.8924	High Similarity	NPC36320
0.8924	High Similarity	NPC169471
0.8919	High Similarity	NPC226942
0.8919	High Similarity	NPC470636
0.8919	High Similarity	NPC73028
0.8919	High Similarity	NPC84266
0.8919	High Similarity	NPC96791
0.8917	High Similarity	NPC193998
0.891	High Similarity	NPC470810
0.8904	High Similarity	NPC472368
0.8904	High Similarity	NPC124269
0.8903	High Similarity	NPC196448
0.8897	High Similarity	NPC473391
0.8897	High Similarity	NPC476333
0.8897	High Similarity	NPC472367
0.8897	High Similarity	NPC472364
0.8889	High Similarity	NPC41326
0.8889	High Similarity	NPC87708
0.8882	High Similarity	NPC119929
0.8882	High Similarity	NPC60413
0.8882	High Similarity	NPC202595
0.8874	High Similarity	NPC106328
0.8874	High Similarity	NPC186397
0.8874	High Similarity	NPC39195
0.8874	High Similarity	NPC37135
0.8874	High Similarity	NPC168085
0.8874	High Similarity	NPC35150
0.8867	High Similarity	NPC267509
0.8867	High Similarity	NPC196114
0.8867	High Similarity	NPC187282
0.8867	High Similarity	NPC99454
0.8867	High Similarity	NPC24136
0.8867	High Similarity	NPC130176
0.8867	High Similarity	NPC290133
0.8861	High Similarity	NPC155640
0.8861	High Similarity	NPC1755
0.8861	High Similarity	NPC1706
0.8861	High Similarity	NPC59295
0.8861	High Similarity	NPC263092
0.8861	High Similarity	NPC39305
0.8859	High Similarity	NPC113770
0.8859	High Similarity	NPC262935
0.8859	High Similarity	NPC172182
0.8859	High Similarity	NPC19896
0.8859	High Similarity	NPC251182
0.8854	High Similarity	NPC304387
0.8851	High Similarity	NPC182255
0.8851	High Similarity	NPC103752
0.8851	High Similarity	NPC94076
0.8851	High Similarity	NPC96692
0.8851	High Similarity	NPC105648
0.8851	High Similarity	NPC250755
0.8844	High Similarity	NPC472366
0.8839	High Similarity	NPC146211
0.8839	High Similarity	NPC472461
0.8836	High Similarity	NPC188879

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 NPC106372 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	991
0.2-0.3	1610
0.3-0.4	2684
0.4-0.5	1825
0.5-0.6	1074
0.6-0.7	390
0.7-0.8	121
0.8-0.85	46
0.85-0.9	18
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8903	High Similarity	NPD3749	Approved
0.8707	High Similarity	NPD2344	Approved
0.8675	High Similarity	NPD4378	Clinical (unspecified phase)
0.8616	High Similarity	NPD6959	Discontinued
0.8599	High Similarity	NPD3882	Suspended
0.859	High Similarity	NPD7819	Suspended
0.8553	High Similarity	NPD2533	Approved
0.8553	High Similarity	NPD2534	Approved
0.8553	High Similarity	NPD2532	Approved
0.8552	High Similarity	NPD1240	Approved
0.8523	High Similarity	NPD1549	Phase 2
0.8523	High Similarity	NPD970	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD2309	Approved
0.8471	Intermediate Similarity	NPD2801	Approved
0.8471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD2800	Approved
0.8456	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1510	Phase 2
0.8435	Intermediate Similarity	NPD1607	Approved
0.8431	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD1934	Approved
0.8395	Intermediate Similarity	NPD3926	Phase 2
0.8389	Intermediate Similarity	NPD2796	Approved
0.8366	Intermediate Similarity	NPD1511	Approved
0.8344	Intermediate Similarity	NPD1243	Approved
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD920	Approved
0.8302	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.8289	Intermediate Similarity	NPD3750	Approved
0.8263	Intermediate Similarity	NPD6559	Discontinued
0.8258	Intermediate Similarity	NPD1512	Approved
0.8242	Intermediate Similarity	NPD3818	Discontinued
0.8228	Intermediate Similarity	NPD7411	Suspended
0.821	Intermediate Similarity	NPD5494	Approved
0.8194	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD4380	Phase 2
0.8137	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7768	Phase 2
0.8129	Intermediate Similarity	NPD6799	Approved
0.8121	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6166	Phase 2
0.8121	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7075	Discontinued
0.8079	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD6599	Discontinued
0.8049	Intermediate Similarity	NPD1247	Approved
0.8026	Intermediate Similarity	NPD2935	Discontinued
0.8013	Intermediate Similarity	NPD7390	Discontinued
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.7987	Intermediate Similarity	NPD3226	Approved
0.7976	Intermediate Similarity	NPD5844	Phase 1
0.7963	Intermediate Similarity	NPD3817	Phase 2
0.7961	Intermediate Similarity	NPD3748	Approved
0.7927	Intermediate Similarity	NPD919	Approved
0.7908	Intermediate Similarity	NPD6099	Approved
0.7908	Intermediate Similarity	NPD1551	Phase 2
0.7908	Intermediate Similarity	NPD6100	Approved
0.7892	Intermediate Similarity	NPD5711	Approved
0.7892	Intermediate Similarity	NPD5710	Approved
0.7871	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1471	Phase 3
0.7857	Intermediate Similarity	NPD2346	Discontinued
0.7853	Intermediate Similarity	NPD2296	Approved
0.7843	Intermediate Similarity	NPD2799	Discontinued
0.784	Intermediate Similarity	NPD6801	Discontinued
0.7829	Intermediate Similarity	NPD4287	Approved
0.7824	Intermediate Similarity	NPD7074	Phase 3
0.7815	Intermediate Similarity	NPD943	Approved
0.78	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7229	Phase 3
0.7765	Intermediate Similarity	NPD7054	Approved
0.7744	Intermediate Similarity	NPD5402	Approved
0.7742	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7472	Approved
0.7712	Intermediate Similarity	NPD6651	Approved
0.7707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3764	Approved
0.7674	Intermediate Similarity	NPD6797	Phase 2
0.7674	Intermediate Similarity	NPD5953	Discontinued
0.7674	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7286	Phase 2
0.764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7251	Discontinued
0.7622	Intermediate Similarity	NPD6280	Approved
0.7622	Intermediate Similarity	NPD6279	Approved
0.7613	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7586	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7808	Phase 3
0.7584	Intermediate Similarity	NPD1203	Approved
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.755	Intermediate Similarity	NPD4908	Phase 1
0.7532	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD2654	Approved
0.7531	Intermediate Similarity	NPD5403	Approved
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7471	Intermediate Similarity	NPD6808	Phase 2
0.747	Intermediate Similarity	NPD5761	Phase 2
0.747	Intermediate Similarity	NPD5760	Phase 2
0.7467	Intermediate Similarity	NPD1470	Approved
0.7452	Intermediate Similarity	NPD5408	Approved
0.7452	Intermediate Similarity	NPD5406	Approved
0.7452	Intermediate Similarity	NPD5404	Approved
0.7452	Intermediate Similarity	NPD5405	Approved
0.7451	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6832	Phase 2
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD447	Suspended
0.7417	Intermediate Similarity	NPD2798	Approved
0.7416	Intermediate Similarity	NPD8434	Phase 2
0.741	Intermediate Similarity	NPD37	Approved
0.7407	Intermediate Similarity	NPD5401	Approved
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7384	Intermediate Similarity	NPD2403	Approved
0.7383	Intermediate Similarity	NPD1608	Approved
0.7383	Intermediate Similarity	NPD9717	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7368	Intermediate Similarity	NPD3787	Discontinued
0.7351	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8313	Approved
0.7345	Intermediate Similarity	NPD8312	Approved
0.7338	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4288	Approved
0.7315	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1610	Phase 2
0.7315	Intermediate Similarity	NPD1201	Approved
0.7314	Intermediate Similarity	NPD1729	Discontinued
0.7285	Intermediate Similarity	NPD1876	Approved
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7267	Intermediate Similarity	NPD7003	Approved
0.7267	Intermediate Similarity	NPD3972	Approved
0.7255	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2797	Approved
0.7228	Intermediate Similarity	NPD4361	Phase 2
0.7228	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD411	Approved
0.7225	Intermediate Similarity	NPD8151	Discontinued
0.7219	Intermediate Similarity	NPD4749	Approved
0.7208	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7177	Discontinued
0.72	Intermediate Similarity	NPD422	Phase 1
0.7195	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD17	Approved
0.7174	Intermediate Similarity	NPD4363	Phase 3
0.7174	Intermediate Similarity	NPD4360	Phase 2
0.717	Intermediate Similarity	NPD4308	Phase 3
0.7162	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7135	Intermediate Similarity	NPD6971	Discontinued
0.7134	Intermediate Similarity	NPD1613	Approved
0.7134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1651	Approved
0.7102	Intermediate Similarity	NPD7228	Approved
0.7101	Intermediate Similarity	NPD6844	Discontinued
0.7074	Intermediate Similarity	NPD6782	Approved
0.7074	Intermediate Similarity	NPD6776	Approved
0.7074	Intermediate Similarity	NPD6777	Approved
0.7074	Intermediate Similarity	NPD6780	Approved
0.7074	Intermediate Similarity	NPD6779	Approved
0.7074	Intermediate Similarity	NPD6778	Approved
0.7074	Intermediate Similarity	NPD6781	Approved
0.7072	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1283	Approved
0.7051	Intermediate Similarity	NPD3027	Phase 3
0.7047	Intermediate Similarity	NPD9545	Approved
0.7041	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5242	Approved
0.7027	Intermediate Similarity	NPD9493	Approved
0.7025	Intermediate Similarity	NPD4060	Phase 1
0.7016	Intermediate Similarity	NPD7870	Phase 2
0.7016	Intermediate Similarity	NPD7871	Phase 2
0.7013	Intermediate Similarity	NPD3266	Approved
0.7013	Intermediate Similarity	NPD1164	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