NPASS Compound

Structure

CID164110 OpenBabel06191715532D 22 24 0 0 0 0 0 0 0 0999 V2000 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 2.5411 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 1.8171 -0.1910 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 0.0000 1.6180 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 -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 -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 0.9511 0.3090 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 -0.5878 0.8090 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 -3.0878 -0.0570 0.0000 C 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 -3.5878 2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 21 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.12
Volume:	310.921
LogP:	4.636
LogD:	3.069
LogS:	-4.661
# 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:	0.734
Synthetic Accessibility Score:	2.538
Fsp3:	0.222
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:	-4.968
MDCK Permeability:	1.5188261386356317e-05
Pgp-inhibitor:	0.044
Pgp-substrate:	0.815
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.476
30% Bioavailability (F30%):	0.563

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	99.18681335449219%
Volume Distribution (VD):	0.508
Pgp-substrate:	2.7217116355895996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.857
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.626
CYP2C19-substrate:	0.365
CYP2C9-inhibitor:	0.731
CYP2C9-substrate:	0.802
CYP2D6-inhibitor:	0.395
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.363
CYP3A4-substrate:	0.454

ADMET: Excretion

Clearance (CL):	9.208
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.811
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.373
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.881
Carcinogencity:	0.182
Eye Corrosion:	0.004
Eye Irritation:	0.921
Respiratory Toxicity:	0.505

Download Data

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

Natural Product: NPC164110

Natural Product ID:	NPC164110
*Common Name:**	Stemofuran G
IUPAC Name:	2-(3-hydroxy-5-methoxy-2,4-dimethylphenyl)-5-methyl-1-benzofuran-4-ol
Synonyms:	Stemofuran G
Standard InCHIKey:	RWBWMAOKPGSLMN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O4/c1-9-5-6-14-13(17(9)19)8-16(22-14)12-7-15(21-4)11(3)18(20)10(12)2/h5-8,19-20H,1-4H3
SMILES:	COc1cc(c2oc3c(c2)c(O)c(cc3)C)c(c(c1C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513458
PubChem CID:	11748527
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	2
IC50	1
MIC	4
Others	5

Activity Type	# Activity
Organism	10
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3821	Organism	Alternaria citri	Alternaria citri	EC50	=	14.0	ug.mL-1	PMID[542987]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC50	>	200.0	ug.mL-1	PMID[542987]
NPT3821	Organism	Alternaria citri	Alternaria citri	EC90	>	200.0	ug ml-1	PMID[542987]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	EC90	>	200.0	ug ml-1	PMID[542987]
NPT3821	Organism	Alternaria citri	Alternaria citri	MIC	>	200.0	ug.mL-1	PMID[542987]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	MIC	>	200.0	ug.mL-1	PMID[542987]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	>	200.0	ug.mL-1	PMID[542987]
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	>	200.0	ug.mL-1	PMID[542987]
NPT3660	Organism	Fusarium avenaceum	Fusarium avenaceum	Inhibition	=	30.0	%	PMID[542987]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	Inhibition	=	30.0	%	PMID[542987]
NPT2	Others	Unspecified		IC50	=	3700.0	nM	PMID[542988]
NPT2	Others	Unspecified		Inhibition	=	10.0	%	PMID[542988]

☑ 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 NPC164110 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	416
0.1-0.2	1836
0.2-0.3	3966
0.3-0.4	10740
0.4-0.5	7579
0.5-0.6	3626
0.6-0.7	5558
0.7-0.8	5013
0.8-0.85	2675
0.85-0.9	1125
0.9-0.95	137
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC96342
1.0	High Similarity	NPC212967
1.0	High Similarity	NPC246647
0.9933	High Similarity	NPC180924
0.9866	High Similarity	NPC148938
0.9799	High Similarity	NPC235333
0.9733	High Similarity	NPC213936
0.9733	High Similarity	NPC297531
0.9732	High Similarity	NPC207624
0.9664	High Similarity	NPC23668
0.9664	High Similarity	NPC170169
0.9664	High Similarity	NPC193976
0.9664	High Similarity	NPC106372
0.9664	High Similarity	NPC58668
0.9664	High Similarity	NPC115324
0.9605	High Similarity	NPC268360
0.96	High Similarity	NPC142308
0.9597	High Similarity	NPC230713
0.9597	High Similarity	NPC13282
0.9597	High Similarity	NPC78335
0.9597	High Similarity	NPC167576
0.953	High Similarity	NPC226644
0.953	High Similarity	NPC37226
0.953	High Similarity	NPC178202
0.9474	High Similarity	NPC99199
0.9474	High Similarity	NPC198490
0.9463	High Similarity	NPC135325
0.9408	High Similarity	NPC472462
0.9408	High Similarity	NPC72370
0.9408	High Similarity	NPC213608
0.9408	High Similarity	NPC183874
0.9408	High Similarity	NPC1477
0.9396	High Similarity	NPC12148
0.9396	High Similarity	NPC17816
0.9396	High Similarity	NPC130581
0.9342	High Similarity	NPC5871
0.9329	High Similarity	NPC51641
0.9329	High Similarity	NPC300267
0.9329	High Similarity	NPC210826
0.9304	High Similarity	NPC53640
0.9286	High Similarity	NPC160015
0.9286	High Similarity	NPC137100
0.9286	High Similarity	NPC247677
0.9276	High Similarity	NPC258249
0.9272	High Similarity	NPC158338
0.9272	High Similarity	NPC97029
0.9272	High Similarity	NPC97028
0.9272	High Similarity	NPC65589
0.9272	High Similarity	NPC288036
0.9272	High Similarity	NPC39929
0.9272	High Similarity	NPC296030
0.9272	High Similarity	NPC100985
0.9262	High Similarity	NPC98926
0.9262	High Similarity	NPC155144
0.9262	High Similarity	NPC230943
0.9226	High Similarity	NPC260902
0.9226	High Similarity	NPC296957
0.9226	High Similarity	NPC65504
0.9216	High Similarity	NPC40356
0.9216	High Similarity	NPC154683
0.9205	High Similarity	NPC7025
0.9205	High Similarity	NPC256672
0.9205	High Similarity	NPC27221
0.9195	High Similarity	NPC302181
0.9195	High Similarity	NPC225884
0.9177	High Similarity	NPC159508
0.9167	High Similarity	NPC40583
0.9167	High Similarity	NPC476350
0.9167	High Similarity	NPC472877
0.9167	High Similarity	NPC476349
0.9156	High Similarity	NPC329844
0.9156	High Similarity	NPC169990
0.9156	High Similarity	NPC210942
0.915	High Similarity	NPC232645
0.915	High Similarity	NPC474417
0.915	High Similarity	NPC72958
0.915	High Similarity	NPC149526
0.9145	High Similarity	NPC65775
0.9145	High Similarity	NPC37208
0.9145	High Similarity	NPC221868
0.9145	High Similarity	NPC10027
0.9139	High Similarity	NPC7943
0.9139	High Similarity	NPC22005
0.9139	High Similarity	NPC123202
0.9128	High Similarity	NPC53192
0.9128	High Similarity	NPC84266
0.9125	High Similarity	NPC253730
0.9125	High Similarity	NPC286230
0.9119	High Similarity	NPC169471
0.9108	High Similarity	NPC304839
0.9108	High Similarity	NPC470810
0.9108	High Similarity	NPC115432
0.9108	High Similarity	NPC260296
0.9108	High Similarity	NPC220582
0.9097	High Similarity	NPC66508
0.9097	High Similarity	NPC226656
0.9091	High Similarity	NPC87708
0.9091	High Similarity	NPC253872
0.9091	High Similarity	NPC67654
0.9091	High Similarity	NPC263676
0.9085	High Similarity	NPC202595
0.9085	High Similarity	NPC227122
0.9085	High Similarity	NPC119929
0.9079	High Similarity	NPC272194
0.9062	High Similarity	NPC277480
0.906	High Similarity	NPC182255
0.906	High Similarity	NPC94076
0.906	High Similarity	NPC49108
0.9057	High Similarity	NPC133065
0.9051	High Similarity	NPC74854
0.9051	High Similarity	NPC45124
0.9051	High Similarity	NPC30655
0.9045	High Similarity	NPC244750
0.9045	High Similarity	NPC324736
0.9038	High Similarity	NPC146211
0.9032	High Similarity	NPC135522
0.9032	High Similarity	NPC122365
0.9026	High Similarity	NPC478148
0.9026	High Similarity	NPC156244
0.9026	High Similarity	NPC116604
0.902	High Similarity	NPC329933
0.902	High Similarity	NPC291049
0.902	High Similarity	NPC233267
0.902	High Similarity	NPC317492
0.902	High Similarity	NPC266499
0.9018	High Similarity	NPC65885
0.9013	High Similarity	NPC289042
0.9013	High Similarity	NPC56433
0.9013	High Similarity	NPC150215
0.9013	High Similarity	NPC190648
0.9013	High Similarity	NPC245584
0.9013	High Similarity	NPC118027
0.9013	High Similarity	NPC312929
0.9013	High Similarity	NPC126767
0.9013	High Similarity	NPC34802
0.9006	High Similarity	NPC50394
0.9006	High Similarity	NPC247973
0.9	High Similarity	NPC474591
0.9	High Similarity	NPC136641
0.9	High Similarity	NPC39306
0.9	High Similarity	NPC37183
0.8994	High Similarity	NPC312056
0.8994	High Similarity	NPC84515
0.8994	High Similarity	NPC193998
0.8987	High Similarity	NPC313368
0.8987	High Similarity	NPC186325
0.8968	High Similarity	NPC273483
0.8968	High Similarity	NPC217447
0.8968	High Similarity	NPC271681
0.8963	High Similarity	NPC227906
0.8961	High Similarity	NPC470568
0.8961	High Similarity	NPC290954
0.8961	High Similarity	NPC255641
0.8961	High Similarity	NPC325983
0.8961	High Similarity	NPC147735
0.8961	High Similarity	NPC294646
0.8954	High Similarity	NPC2569
0.8954	High Similarity	NPC186397
0.8954	High Similarity	NPC39195
0.8954	High Similarity	NPC37135
0.8954	High Similarity	NPC168085
0.8954	High Similarity	NPC105415
0.8954	High Similarity	NPC172329
0.8947	High Similarity	NPC196114
0.8947	High Similarity	NPC225173
0.8947	High Similarity	NPC163846
0.8947	High Similarity	NPC99454
0.8947	High Similarity	NPC130176
0.894	High Similarity	NPC189650
0.8938	High Similarity	NPC155640
0.8931	High Similarity	NPC273467
0.8931	High Similarity	NPC66288
0.8931	High Similarity	NPC188486
0.8931	High Similarity	NPC24761
0.8931	High Similarity	NPC304387
0.8931	High Similarity	NPC269117
0.8931	High Similarity	NPC18380
0.8931	High Similarity	NPC189552
0.8926	High Similarity	NPC472366
0.8924	High Similarity	NPC177650
0.8924	High Similarity	NPC226287
0.8917	High Similarity	NPC45131
0.891	High Similarity	NPC214632
0.891	High Similarity	NPC280530
0.891	High Similarity	NPC95842
0.891	High Similarity	NPC178964
0.8909	High Similarity	NPC49667
0.8909	High Similarity	NPC8127
0.8903	High Similarity	NPC133856
0.8903	High Similarity	NPC149085
0.8903	High Similarity	NPC470569
0.8896	High Similarity	NPC476641
0.8896	High Similarity	NPC269420
0.8896	High Similarity	NPC223988
0.8896	High Similarity	NPC131866
0.8889	High Similarity	NPC308200
0.8889	High Similarity	NPC137296
0.8889	High Similarity	NPC125801
0.8889	High Similarity	NPC71055
0.8889	High Similarity	NPC77903

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 NPC164110 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	1006
0.2-0.3	1503
0.3-0.4	2668
0.4-0.5	1880
0.5-0.6	1107
0.6-0.7	395
0.7-0.8	138
0.8-0.85	50
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8812	High Similarity	NPD6959	Discontinued
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.8758	High Similarity	NPD2532	Approved
0.8758	High Similarity	NPD2534	Approved
0.8758	High Similarity	NPD2533	Approved
0.8742	High Similarity	NPD3749	Approved
0.8671	High Similarity	NPD7819	Suspended
0.8642	High Similarity	NPD6232	Discontinued
0.8598	High Similarity	NPD7473	Discontinued
0.8563	High Similarity	NPD6559	Discontinued
0.8553	High Similarity	NPD2393	Clinical (unspecified phase)
0.8543	High Similarity	NPD2344	Approved
0.8523	High Similarity	NPD1607	Approved
0.8516	High Similarity	NPD7410	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD3882	Suspended
0.8431	Intermediate Similarity	NPD2800	Approved
0.8408	Intermediate Similarity	NPD920	Approved
0.8389	Intermediate Similarity	NPD1240	Approved
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD1549	Phase 2
0.8323	Intermediate Similarity	NPD2309	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8313	Intermediate Similarity	NPD7411	Suspended
0.8312	Intermediate Similarity	NPD1243	Approved
0.8302	Intermediate Similarity	NPD3226	Approved
0.8301	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5494	Approved
0.8289	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.828	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD5844	Phase 1
0.8261	Intermediate Similarity	NPD1934	Approved
0.8253	Intermediate Similarity	NPD3926	Phase 2
0.825	Intermediate Similarity	NPD4380	Phase 2
0.8247	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD2796	Approved
0.8221	Intermediate Similarity	NPD7768	Phase 2
0.8217	Intermediate Similarity	NPD1511	Approved
0.8217	Intermediate Similarity	NPD7390	Discontinued
0.8204	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2346	Discontinued
0.8171	Intermediate Similarity	NPD7075	Discontinued
0.8153	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD3750	Approved
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.8133	Intermediate Similarity	NPD1247	Approved
0.8117	Intermediate Similarity	NPD2935	Discontinued
0.8113	Intermediate Similarity	NPD1512	Approved
0.8107	Intermediate Similarity	NPD3818	Discontinued
0.8098	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5710	Approved
0.8084	Intermediate Similarity	NPD5711	Approved
0.8012	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7988	Intermediate Similarity	NPD6166	Phase 2
0.7988	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6799	Approved
0.7962	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1471	Phase 3
0.7935	Intermediate Similarity	NPD2799	Discontinued
0.7927	Intermediate Similarity	NPD6801	Discontinued
0.7892	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6100	Approved
0.7885	Intermediate Similarity	NPD6099	Approved
0.787	Intermediate Similarity	NPD7229	Phase 3
0.7834	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD3817	Phase 2
0.7829	Intermediate Similarity	NPD4625	Phase 3
0.7821	Intermediate Similarity	NPD3748	Approved
0.7791	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5408	Approved
0.7771	Intermediate Similarity	NPD1465	Phase 2
0.7771	Intermediate Similarity	NPD5404	Approved
0.7771	Intermediate Similarity	NPD5406	Approved
0.7771	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5405	Approved
0.7759	Intermediate Similarity	NPD5953	Discontinued
0.7746	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7286	Phase 2
0.7744	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD2296	Approved
0.7709	Intermediate Similarity	NPD4287	Approved
0.7701	Intermediate Similarity	NPD7074	Phase 3
0.7692	Intermediate Similarity	NPD6651	Approved
0.7688	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.7677	Intermediate Similarity	NPD943	Approved
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7662	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7054	Approved
0.7627	Intermediate Similarity	NPD8312	Approved
0.7627	Intermediate Similarity	NPD8313	Approved
0.7624	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5402	Approved
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7472	Approved
0.7578	Intermediate Similarity	NPD7003	Approved
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1470	Approved
0.756	Intermediate Similarity	NPD5761	Phase 2
0.756	Intermediate Similarity	NPD5760	Phase 2
0.7557	Intermediate Similarity	NPD6797	Phase 2
0.7548	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3764	Approved
0.7515	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD6279	Approved
0.75	Intermediate Similarity	NPD6280	Approved
0.75	Intermediate Similarity	NPD8434	Phase 2
0.7486	Intermediate Similarity	NPD7177	Discontinued
0.7484	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7808	Phase 3
0.7458	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1203	Approved
0.745	Intermediate Similarity	NPD1651	Approved
0.7433	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4908	Phase 1
0.7417	Intermediate Similarity	NPD1201	Approved
0.7416	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5403	Approved
0.7401	Intermediate Similarity	NPD1729	Discontinued
0.7399	Intermediate Similarity	NPD7199	Phase 2
0.7396	Intermediate Similarity	NPD37	Approved
0.7396	Intermediate Similarity	NPD8151	Discontinued
0.7394	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3751	Discontinued
0.7386	Intermediate Similarity	NPD1283	Approved
0.7384	Intermediate Similarity	NPD6234	Discontinued
0.7368	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD4965	Approved
0.7368	Intermediate Similarity	NPD3972	Approved
0.7356	Intermediate Similarity	NPD6808	Phase 2
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.7325	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD411	Approved
0.7314	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4361	Phase 2
0.7312	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7301	Intermediate Similarity	NPD2654	Approved
0.7296	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD230	Phase 1
0.729	Intermediate Similarity	NPD2798	Approved
0.7289	Intermediate Similarity	NPD5401	Approved
0.7277	Intermediate Similarity	NPD7871	Phase 2
0.7277	Intermediate Similarity	NPD7870	Phase 2
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7258	Intermediate Similarity	NPD4363	Phase 3
0.7258	Intermediate Similarity	NPD4360	Phase 2
0.7257	Intermediate Similarity	NPD3787	Discontinued
0.7255	Intermediate Similarity	NPD9717	Approved
0.7255	Intermediate Similarity	NPD1608	Approved
0.7246	Intermediate Similarity	NPD6273	Approved
0.7233	Intermediate Similarity	NPD2979	Phase 3
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7229	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7698	Approved
0.7225	Intermediate Similarity	NPD7696	Phase 3
0.7225	Intermediate Similarity	NPD7697	Approved
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7215	Intermediate Similarity	NPD3268	Approved
0.7213	Intermediate Similarity	NPD8150	Discontinued
0.7209	Intermediate Similarity	NPD4288	Approved
0.7208	Intermediate Similarity	NPD4749	Approved
0.719	Intermediate Similarity	NPD1610	Phase 2
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1281	Approved
0.7175	Intermediate Similarity	NPD2403	Approved
0.7171	Intermediate Similarity	NPD4626	Approved
0.7161	Intermediate Similarity	NPD1876	Approved
0.7161	Intermediate Similarity	NPD6696	Suspended
0.716	Intermediate Similarity	NPD7033	Discontinued
0.7158	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4060	Phase 1
0.7115	Intermediate Similarity	NPD2797	Approved
0.7115	Intermediate Similarity	NPD1164	Approved
0.7107	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7228	Approved
0.7091	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6823	Phase 2
0.7079	Intermediate Similarity	NPD4575	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