NPASS Compound

Structure

NPC226942 OpenBabel07101719512D 30 32 0 0 1 0 0 0 0 0999 V2000 0.0850 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5714 1.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7524 -0.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4013 2.6361 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 -0.0000 1.6180 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 -1.5823 0.9135 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 -2.1701 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.5316 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 -1.9890 1.8271 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 -0.5878 0.8090 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 -1.7634 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 3.3406 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 -2.9836 1.9316 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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 8 1 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 8 16 1 0 0 0 0 9 4 1 6 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 10 20 1 0 0 0 0 11 19 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 12 22 2 0 0 0 0 13 19 1 0 0 0 0 13 23 2 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 24 2 0 0 0 0 17 25 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.17
Volume:	421.135
LogP:	5.586
LogD:	2.684
LogS:	-3.942
# Rotatable Bonds:	5
TPSA:	128.2
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	3.702
Fsp3:	0.391
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.046
MDCK Permeability:	1.057509689417202e-05
Pgp-inhibitor:	0.209
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.269
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	97.85071563720703%
Volume Distribution (VD):	0.424
Pgp-substrate:	1.9173672199249268%

ADMET: Metabolism

CYP1A2-inhibitor:	0.626
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.156
CYP2C19-substrate:	0.252
CYP2C9-inhibitor:	0.821
CYP2C9-substrate:	0.609
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.199

ADMET: Excretion

Clearance (CL):	4.753
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.548
Rat Oral Acute Toxicity:	0.158
Maximum Recommended Daily Dose:	0.297
Skin Sensitization:	0.847
Carcinogencity:	0.183
Eye Corrosion:	0.003
Eye Irritation:	0.491
Respiratory Toxicity:	0.151

Download Data

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

Natural Product: NPC226942

Natural Product ID:	NPC226942
*Common Name:**	(2S)-2-Methyl-1-[1,3,7,9-Tetrahydroxy-2,8-Dimethyl-6-(2-Methylpropanoyl)Dibenzofuran-4-Yl]Butan-1-One
IUPAC Name:	(2S)-2-methyl-1-[1,3,7,9-tetrahydroxy-2,8-dimethyl-6-(2-methylpropanoyl)dibenzofuran-4-yl]butan-1-one
Synonyms:
Standard InCHIKey:	SIPJAOYDFTWIRY-VIFPVBQESA-N
Standard InCHI:	InChI=1S/C23H26O7/c1-7-9(4)17(25)15-21(29)11(6)19(27)13-12-18(26)10(5)20(28)14(16(24)8(2)3)22(12)30-23(13)15/h8-9,26-29H,7H2,1-6H3/t9-/m0/s1
SMILES:	CC[C@@H](C(=O)c1c(O)c(C)c(c2c1oc1c2c(O)c(c(c1C(=O)C(C)C)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2146931
PubChem CID:	71461795
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0000015] Dibenzofurans

*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
NPO32572	pilidostigma glabrum	Species	n.a.	n.a.	n.a.	Australian	n.a.	PMID[22934671]

☑ 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
ED50	2
IC50	2
MIC	3
Others	5

Activity Type	# Activity
Cell Line	5
Organism	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4400.0	nM	PMID[532996]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	>	200000.0	nM	PMID[532996]
NPT113	Cell Line	RAW264.7	Mus musculus	ED50	=	17.6	uM	PMID[532996]
NPT886	Cell Line	NIH3T3	Mus musculus	ED50	=	22.3	uM	PMID[532996]
NPT113	Cell Line	RAW264.7	Mus musculus	Selectivity Index	=	4.0	n.a.	PMID[532996]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12100.0	nM	PMID[532996]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	24.1	uM	PMID[532996]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6000.0	nM	PMID[532996]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	6000.0	nM	PMID[532996]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	=	6.0	uM	PMID[532996]
NPT35	Others	n.a.		Activity	=	6281.0	umol/g	PMID[532996]

☑ 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 NPC226942 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	390
0.1-0.2	1765
0.2-0.3	4149
0.3-0.4	11027
0.4-0.5	8365
0.5-0.6	4649
0.6-0.7	5631
0.7-0.8	4533
0.8-0.85	1720
0.85-0.9	444
0.9-0.95	18
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC96791
1.0	High Similarity	NPC470636
0.9783	High Similarity	NPC172182
0.9783	High Similarity	NPC251182
0.9783	High Similarity	NPC262935
0.922	High Similarity	NPC111201
0.9189	High Similarity	NPC474386
0.9172	High Similarity	NPC226644
0.9172	High Similarity	NPC37226
0.9172	High Similarity	NPC178202
0.9149	High Similarity	NPC164697
0.9149	High Similarity	NPC289660
0.9149	High Similarity	NPC82920
0.9116	High Similarity	NPC5871
0.911	High Similarity	NPC78335
0.911	High Similarity	NPC230713
0.9103	High Similarity	NPC135325
0.9097	High Similarity	NPC210826
0.9078	High Similarity	NPC270913
0.906	High Similarity	NPC160015
0.906	High Similarity	NPC247677
0.9054	High Similarity	NPC213608
0.9054	High Similarity	NPC1477
0.9054	High Similarity	NPC235333
0.9048	High Similarity	NPC170169
0.9034	High Similarity	NPC130581
0.9034	High Similarity	NPC12148
0.9	High Similarity	NPC260902
0.9	High Similarity	NPC296957
0.8993	High Similarity	NPC297531
0.8993	High Similarity	NPC148938
0.8993	High Similarity	NPC213936
0.8966	High Similarity	NPC51641
0.8966	High Similarity	NPC300267
0.8958	High Similarity	NPC225884
0.8947	High Similarity	NPC472346
0.894	High Similarity	NPC476350
0.894	High Similarity	NPC40583
0.894	High Similarity	NPC476349
0.894	High Similarity	NPC244750
0.8933	High Similarity	NPC180924
0.8926	High Similarity	NPC183874
0.8926	High Similarity	NPC472462
0.8919	High Similarity	NPC193976
0.8919	High Similarity	NPC106372
0.8919	High Similarity	NPC58668
0.8919	High Similarity	NPC23668
0.8912	High Similarity	NPC221868
0.8912	High Similarity	NPC39929
0.8912	High Similarity	NPC37208
0.8912	High Similarity	NPC296030
0.8904	High Similarity	NPC17816
0.8897	High Similarity	NPC230943
0.8882	High Similarity	NPC115432
0.8882	High Similarity	NPC260296
0.8874	High Similarity	NPC268360
0.8874	High Similarity	NPC164110
0.8874	High Similarity	NPC96342
0.8874	High Similarity	NPC65504
0.8874	High Similarity	NPC212967
0.8874	High Similarity	NPC246647
0.8867	High Similarity	NPC198490
0.8859	High Similarity	NPC142308
0.8859	High Similarity	NPC207624
0.8859	High Similarity	NPC67654
0.8851	High Similarity	NPC167576
0.8844	High Similarity	NPC272194
0.8828	High Similarity	NPC302181
0.8792	High Similarity	NPC156244
0.8792	High Similarity	NPC115324
0.8776	High Similarity	NPC308200
0.8768	High Similarity	NPC186628
0.8767	High Similarity	NPC155144
0.8759	High Similarity	NPC472344
0.8759	High Similarity	NPC53192
0.875	High Similarity	NPC469818
0.8742	High Similarity	NPC99199
0.8733	High Similarity	NPC263676
0.8725	High Similarity	NPC476509
0.8716	High Similarity	NPC145467
0.8716	High Similarity	NPC39195
0.871	High Similarity	NPC155640
0.8705	High Similarity	NPC279566
0.869	High Similarity	NPC157497
0.869	High Similarity	NPC285659
0.869	High Similarity	NPC81337
0.8681	High Similarity	NPC240305
0.8675	High Similarity	NPC122365
0.8675	High Similarity	NPC72370
0.8671	High Similarity	NPC255801
0.8671	High Similarity	NPC322301
0.8667	High Similarity	NPC116604
0.8658	High Similarity	NPC317492
0.8658	High Similarity	NPC471114
0.8654	High Similarity	NPC136641
0.8654	High Similarity	NPC204088
0.8654	High Similarity	NPC259007
0.8654	High Similarity	NPC329215
0.8639	High Similarity	NPC271288
0.8639	High Similarity	NPC98926
0.8639	High Similarity	NPC311144
0.8639	High Similarity	NPC326500
0.8636	High Similarity	NPC304839
0.8636	High Similarity	NPC220582
0.8621	High Similarity	NPC477272
0.8621	High Similarity	NPC28337
0.8611	High Similarity	NPC183639
0.8611	High Similarity	NPC474487
0.8611	High Similarity	NPC254168
0.8611	High Similarity	NPC248995
0.8611	High Similarity	NPC199458
0.8611	High Similarity	NPC474504
0.8611	High Similarity	NPC272844
0.8611	High Similarity	NPC470672
0.8611	High Similarity	NPC470671
0.8609	High Similarity	NPC41326
0.8609	High Similarity	NPC253872
0.8601	High Similarity	NPC470983
0.8601	High Similarity	NPC470982
0.86	High Similarity	NPC472406
0.86	High Similarity	NPC476185
0.86	High Similarity	NPC29777
0.86	High Similarity	NPC321896
0.86	High Similarity	NPC471115
0.8599	High Similarity	NPC323137
0.8591	High Similarity	NPC168085
0.859	High Similarity	NPC38591
0.859	High Similarity	NPC109180
0.859	High Similarity	NPC159508
0.8582	High Similarity	NPC215875
0.8582	High Similarity	NPC15834
0.8581	High Similarity	NPC45124
0.8581	High Similarity	NPC477955
0.8581	High Similarity	NPC74854
0.8581	High Similarity	NPC299011
0.8581	High Similarity	NPC30655
0.8571	High Similarity	NPC9117
0.8571	High Similarity	NPC24821
0.8571	High Similarity	NPC190637
0.8571	High Similarity	NPC112749
0.8571	High Similarity	NPC293053
0.8571	High Similarity	NPC113770
0.8571	High Similarity	NPC212932
0.8571	High Similarity	NPC11700
0.8562	High Similarity	NPC476508
0.8562	High Similarity	NPC74397
0.8562	High Similarity	NPC137100
0.8562	High Similarity	NPC282300
0.8552	High Similarity	NPC55018
0.8552	High Similarity	NPC477956
0.8552	High Similarity	NPC216978
0.8552	High Similarity	NPC220062
0.8552	High Similarity	NPC301217
0.8552	High Similarity	NPC53181
0.8552	High Similarity	NPC241975
0.8552	High Similarity	NPC19476
0.8552	High Similarity	NPC217186
0.8552	High Similarity	NPC96565
0.8552	High Similarity	NPC303633
0.8544	High Similarity	NPC50394
0.8544	High Similarity	NPC286230
0.8544	High Similarity	NPC253730
0.8544	High Similarity	NPC476459
0.8543	High Similarity	NPC290671
0.8542	High Similarity	NPC138047
0.8542	High Similarity	NPC474624
0.8542	High Similarity	NPC62735
0.8542	High Similarity	NPC131782
0.8535	High Similarity	NPC169471
0.8535	High Similarity	NPC37183
0.8531	High Similarity	NPC101752
0.8526	High Similarity	NPC219861
0.8521	High Similarity	NPC16197
0.8514	High Similarity	NPC184649
0.8514	High Similarity	NPC273538
0.8514	High Similarity	NPC224714
0.8514	High Similarity	NPC470673
0.8514	High Similarity	NPC311741
0.8514	High Similarity	NPC470890
0.8514	High Similarity	NPC117716
0.8514	High Similarity	NPC303185
0.8514	High Similarity	NPC196137
0.8514	High Similarity	NPC1886
0.8514	High Similarity	NPC470674
0.8514	High Similarity	NPC234629
0.8514	High Similarity	NPC216538
0.8506	High Similarity	NPC270044
0.8503	High Similarity	NPC473042
0.8503	High Similarity	NPC470556
0.8503	High Similarity	NPC144499
0.8503	High Similarity	NPC200694
0.8497	Intermediate Similarity	NPC469934
0.8493	Intermediate Similarity	NPC69769
0.8493	Intermediate Similarity	NPC241100
0.8493	Intermediate Similarity	NPC270883
0.8493	Intermediate Similarity	NPC172986
0.8493	Intermediate Similarity	NPC159275
0.8493	Intermediate Similarity	NPC261227
0.8483	Intermediate Similarity	NPC268178
0.8483	Intermediate Similarity	NPC201395

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 NPC226942 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	1024
0.2-0.3	1901
0.3-0.4	2832
0.4-0.5	1821
0.5-0.6	855
0.6-0.7	233
0.7-0.8	100
0.8-0.85	26
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9078	High Similarity	NPD2800	Approved
0.8521	High Similarity	NPD6651	Approved
0.8514	High Similarity	NPD4378	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD2344	Approved
0.8389	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD3749	Approved
0.8267	Intermediate Similarity	NPD2534	Approved
0.8267	Intermediate Similarity	NPD2533	Approved
0.8267	Intermediate Similarity	NPD2532	Approved
0.8258	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2309	Approved
0.8176	Intermediate Similarity	NPD1243	Approved
0.8158	Intermediate Similarity	NPD920	Approved
0.8113	Intermediate Similarity	NPD6959	Discontinued
0.8077	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD1549	Phase 2
0.7949	Intermediate Similarity	NPD7411	Suspended
0.7908	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1510	Phase 2
0.7891	Intermediate Similarity	NPD1607	Approved
0.7885	Intermediate Similarity	NPD4380	Phase 2
0.7862	Intermediate Similarity	NPD7768	Phase 2
0.7862	Intermediate Similarity	NPD3882	Suspended
0.7853	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD2796	Approved
0.7848	Intermediate Similarity	NPD7819	Suspended
0.7848	Intermediate Similarity	NPD2801	Approved
0.7843	Intermediate Similarity	NPD1511	Approved
0.7826	Intermediate Similarity	NPD5494	Approved
0.7812	Intermediate Similarity	NPD7075	Discontinued
0.7805	Intermediate Similarity	NPD7473	Discontinued
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7785	Intermediate Similarity	NPD2799	Discontinued
0.7785	Intermediate Similarity	NPD1934	Approved
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1512	Approved
0.7736	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6232	Discontinued
0.7682	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6801	Discontinued
0.7647	Intermediate Similarity	NPD3750	Approved
0.7633	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5710	Approved
0.7622	Intermediate Similarity	NPD5711	Approved
0.7613	Intermediate Similarity	NPD6799	Approved
0.7593	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2296	Approved
0.7561	Intermediate Similarity	NPD1247	Approved
0.7547	Intermediate Similarity	NPD6599	Discontinued
0.7545	Intermediate Similarity	NPD3818	Discontinued
0.753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6166	Phase 2
0.753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7439	Intermediate Similarity	NPD919	Approved
0.7434	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5953	Discontinued
0.7386	Intermediate Similarity	NPD6099	Approved
0.7386	Intermediate Similarity	NPD6100	Approved
0.7386	Intermediate Similarity	NPD1551	Phase 2
0.7383	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3226	Approved
0.7371	Intermediate Similarity	NPD4287	Approved
0.7362	Intermediate Similarity	NPD3817	Phase 2
0.7338	Intermediate Similarity	NPD1471	Phase 3
0.7338	Intermediate Similarity	NPD2346	Discontinued
0.7337	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3748	Approved
0.7305	Intermediate Similarity	NPD7229	Phase 3
0.7301	Intermediate Similarity	NPD1465	Phase 2
0.7294	Intermediate Similarity	NPD5844	Phase 1
0.7251	Intermediate Similarity	NPD7074	Phase 3
0.7248	Intermediate Similarity	NPD4908	Phase 1
0.7239	Intermediate Similarity	NPD6280	Approved
0.7239	Intermediate Similarity	NPD6279	Approved
0.7219	Intermediate Similarity	NPD2403	Approved
0.7197	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7054	Approved
0.7171	Intermediate Similarity	NPD943	Approved
0.7167	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4361	Phase 2
0.7162	Intermediate Similarity	NPD1203	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1729	Discontinued
0.7151	Intermediate Similarity	NPD7472	Approved
0.7134	Intermediate Similarity	NPD2654	Approved
0.7114	Intermediate Similarity	NPD2798	Approved
0.7111	Intermediate Similarity	NPD4360	Phase 2
0.7111	Intermediate Similarity	NPD4363	Phase 3
0.711	Intermediate Similarity	NPD6797	Phase 2
0.7101	Intermediate Similarity	NPD6808	Phase 2
0.7089	Intermediate Similarity	NPD4628	Phase 3
0.7069	Intermediate Similarity	NPD7251	Discontinued
0.7048	Intermediate Similarity	NPD5402	Approved
0.7047	Intermediate Similarity	NPD2797	Approved
0.7039	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD5403	Approved
0.7029	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7808	Phase 3
0.7024	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5124	Phase 1
0.7011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1610	Phase 2
0.6988	Remote Similarity	NPD5761	Phase 2
0.6988	Remote Similarity	NPD5760	Phase 2
0.6974	Remote Similarity	NPD4625	Phase 3
0.697	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD8434	Phase 2
0.6959	Remote Similarity	NPD1608	Approved
0.6959	Remote Similarity	NPD9717	Approved
0.6943	Remote Similarity	NPD5404	Approved
0.6943	Remote Similarity	NPD5405	Approved
0.6943	Remote Similarity	NPD5406	Approved
0.6943	Remote Similarity	NPD5408	Approved
0.6933	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5401	Approved
0.6908	Remote Similarity	NPD6832	Phase 2
0.6899	Remote Similarity	NPD6004	Phase 3
0.6899	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6005	Phase 3
0.6899	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6002	Phase 3
0.6892	Remote Similarity	NPD422	Phase 1
0.6879	Remote Similarity	NPD7033	Discontinued
0.6875	Remote Similarity	NPD7003	Approved
0.6848	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3972	Approved
0.6842	Remote Similarity	NPD7199	Phase 2
0.6826	Remote Similarity	NPD37	Approved
0.6824	Remote Similarity	NPD6234	Discontinued
0.6821	Remote Similarity	NPD3267	Approved
0.6821	Remote Similarity	NPD1164	Approved
0.6821	Remote Similarity	NPD3266	Approved
0.6813	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4967	Phase 2
0.6805	Remote Similarity	NPD4966	Approved
0.6805	Remote Similarity	NPD4965	Approved
0.68	Remote Similarity	NPD4749	Approved
0.6798	Remote Similarity	NPD8313	Approved
0.6798	Remote Similarity	NPD8312	Approved
0.6795	Remote Similarity	NPD230	Phase 1
0.6795	Remote Similarity	NPD447	Suspended
0.678	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4308	Phase 3
0.6772	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD17	Approved
0.6755	Remote Similarity	NPD1876	Approved
0.6748	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7458	Discontinued
0.6746	Remote Similarity	NPD4288	Approved
0.6738	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1548	Phase 1
0.6732	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1470	Approved
0.6703	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6355	Discontinued
0.6688	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3446	Phase 1
0.6667	Remote Similarity	NPD1201	Approved
0.6648	Remote Similarity	NPD3751	Discontinued
0.6646	Remote Similarity	NPD2424	Discontinued
0.6645	Remote Similarity	NPD3225	Approved
0.6632	Remote Similarity	NPD8151	Discontinued
0.6623	Remote Similarity	NPD2861	Phase 2
0.6609	Remote Similarity	NPD3787	Discontinued
0.6603	Remote Similarity	NPD411	Approved
0.6603	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD1296	Phase 2
0.6599	Remote Similarity	NPD7340	Approved
0.6592	Remote Similarity	NPD6104	Discontinued
0.6588	Remote Similarity	NPD8455	Phase 2
0.6566	Remote Similarity	NPD5049	Phase 3
0.6554	Remote Similarity	NPD7177	Discontinued
0.6554	Remote Similarity	NPD7228	Approved
0.6538	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1283	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