NPASS Compound

Structure

NPC172182 OpenBabel07101719252D 29 31 0 0 0 0 0 0 0 0999 V2000 -0.2257 4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6269 5.2722 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 5.2812 1.8090 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 -1.2202 4.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 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 -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 -1.4013 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 -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 -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 -0.4067 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 -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 -2.8025 3.6542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 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 0.1810 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 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 7 1 0 0 0 0 3 8 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 9 21 2 0 0 0 0 10 18 1 0 0 0 0 10 22 2 0 0 0 0 11 12 1 0 0 0 0 11 19 2 0 0 0 0 11 21 1 0 0 0 0 12 20 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 23 2 0 0 0 0 16 24 2 0 0 0 0 17 25 1 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 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.15
Volume:	403.839
LogP:	5.848
LogD:	2.502
LogS:	-4.024
# Rotatable Bonds:	4
TPSA:	128.2
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	3.202
Fsp3:	0.364
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:	-5.103
MDCK Permeability:	1.0487301551620476e-05
Pgp-inhibitor:	0.13
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.419
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	97.69879150390625%
Volume Distribution (VD):	0.407
Pgp-substrate:	2.127363681793213%

ADMET: Metabolism

CYP1A2-inhibitor:	0.736
CYP1A2-substrate:	0.893
CYP2C19-inhibitor:	0.111
CYP2C19-substrate:	0.169
CYP2C9-inhibitor:	0.777
CYP2C9-substrate:	0.55
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	2.101
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.536
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.484
Skin Sensitization:	0.794
Carcinogencity:	0.261
Eye Corrosion:	0.003
Eye Irritation:	0.362
Respiratory Toxicity:	0.162

Download Data

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

Natural Product: NPC172182

Natural Product ID:	NPC172182
*Common Name:**	1,3,7,9-Tetrahydroxy-4,6-Dimethyl-2,8-Di(2-Methylpropionyl)Dibenzofuran
IUPAC Name:	2-methyl-1-[1,3,7,9-tetrahydroxy-4,6-dimethyl-8-(2-methylpropanoyl)dibenzofuran-2-yl]propan-1-one
Synonyms:
Standard InCHIKey:	YZDDRPAVFBMBPD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H24O7/c1-7(2)15(23)13-17(25)9(5)21-11(19(13)27)12-20(28)14(16(24)8(3)4)18(26)10(6)22(12)29-21/h7-8,25-28H,1-6H3
SMILES:	CC(C(=O)c1c(O)c(C)c2c(c1O)c1c(O)c(C(=O)C(C)C)c(c(c1o2)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2146934
PubChem CID:	71456371
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	6

Activity Type	# Activity
Cell Line	6
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	=	3400.0	nM	PMID[488813]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	4500.0	nM	PMID[488813]
NPT113	Cell Line	RAW264.7	Mus musculus	ED50	=	12.0	uM	PMID[488813]
NPT886	Cell Line	NIH3T3	Mus musculus	ED50	=	15.3	uM	PMID[488813]
NPT113	Cell Line	RAW264.7	Mus musculus	Selectivity Index	=	3.53	n.a.	PMID[488813]
NPT886	Cell Line	NIH3T3	Mus musculus	Selectivity Index	=	3.4	n.a.	PMID[488813]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2700.0	nM	PMID[488813]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	11.4	uM	PMID[488813]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	5.7	uM	PMID[488813]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	2700.0	nM	PMID[488813]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	=	22.7	uM	PMID[488813]
NPT35	Others	n.a.		Activity	=	1451.0	umol/g	PMID[488813]

☑ 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 NPC172182 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	394
0.1-0.2	1800
0.2-0.3	4186
0.3-0.4	11179
0.4-0.5	8227
0.5-0.6	4756
0.6-0.7	5592
0.7-0.8	4605
0.8-0.85	1613
0.85-0.9	331
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC262935
1.0	High Similarity	NPC251182
0.9783	High Similarity	NPC96791
0.9783	High Similarity	NPC470636
0.9783	High Similarity	NPC226942
0.9257	High Similarity	NPC474386
0.911	High Similarity	NPC226644
0.911	High Similarity	NPC178202
0.911	High Similarity	NPC37226
0.9054	High Similarity	NPC5871
0.9048	High Similarity	NPC230713
0.9048	High Similarity	NPC78335
0.9041	High Similarity	NPC135325
0.9034	High Similarity	NPC210826
0.9021	High Similarity	NPC111201
0.9013	High Similarity	NPC472346
0.8993	High Similarity	NPC235333
0.8993	High Similarity	NPC213608
0.8993	High Similarity	NPC1477
0.8986	High Similarity	NPC170169
0.8973	High Similarity	NPC130581
0.8973	High Similarity	NPC12148
0.8951	High Similarity	NPC164697
0.8951	High Similarity	NPC82920
0.8951	High Similarity	NPC289660
0.8933	High Similarity	NPC213936
0.8933	High Similarity	NPC148938
0.8933	High Similarity	NPC297531
0.8926	High Similarity	NPC263676
0.8904	High Similarity	NPC51641
0.8904	High Similarity	NPC300267
0.8897	High Similarity	NPC225884
0.8882	High Similarity	NPC40583
0.8881	High Similarity	NPC270913
0.8874	High Similarity	NPC160015
0.8874	High Similarity	NPC180924
0.8874	High Similarity	NPC247677
0.8867	High Similarity	NPC183874
0.8867	High Similarity	NPC472462
0.8859	High Similarity	NPC58668
0.8859	High Similarity	NPC23668
0.8859	High Similarity	NPC193976
0.8859	High Similarity	NPC106372
0.8859	High Similarity	NPC116604
0.8851	High Similarity	NPC296030
0.8851	High Similarity	NPC39929
0.8851	High Similarity	NPC221868
0.8851	High Similarity	NPC37208
0.8844	High Similarity	NPC17816
0.8836	High Similarity	NPC230943
0.8819	High Similarity	NPC28337
0.8816	High Similarity	NPC96342
0.8816	High Similarity	NPC296957
0.8816	High Similarity	NPC65504
0.8816	High Similarity	NPC260902
0.8816	High Similarity	NPC246647
0.8816	High Similarity	NPC212967
0.8816	High Similarity	NPC164110
0.8816	High Similarity	NPC268360
0.8808	High Similarity	NPC198490
0.88	High Similarity	NPC207624
0.88	High Similarity	NPC142308
0.88	High Similarity	NPC253872
0.8792	High Similarity	NPC167576
0.8792	High Similarity	NPC472406
0.8784	High Similarity	NPC272194
0.8774	High Similarity	NPC109180
0.8767	High Similarity	NPC302181
0.8759	High Similarity	NPC157497
0.8759	High Similarity	NPC285659
0.8759	High Similarity	NPC81337
0.8758	High Similarity	NPC244750
0.8758	High Similarity	NPC476349
0.8758	High Similarity	NPC476350
0.8733	High Similarity	NPC115324
0.8716	High Similarity	NPC308200
0.871	High Similarity	NPC219861
0.8707	High Similarity	NPC155144
0.8705	High Similarity	NPC186628
0.8701	High Similarity	NPC260296
0.8701	High Similarity	NPC115432
0.8699	High Similarity	NPC472344
0.8699	High Similarity	NPC53192
0.869	High Similarity	NPC469818
0.8684	High Similarity	NPC99199
0.8675	High Similarity	NPC67654
0.8667	High Similarity	NPC476509
0.8658	High Similarity	NPC39195
0.8658	High Similarity	NPC145467
0.8654	High Similarity	NPC472581
0.8652	High Similarity	NPC285054
0.8643	High Similarity	NPC279566
0.8621	High Similarity	NPC240305
0.8618	High Similarity	NPC72370
0.8618	High Similarity	NPC122365
0.8611	High Similarity	NPC255801
0.8611	High Similarity	NPC322301
0.8609	High Similarity	NPC156244
0.86	High Similarity	NPC317492
0.86	High Similarity	NPC471114
0.8591	High Similarity	NPC198427
0.859	High Similarity	NPC193998
0.8581	High Similarity	NPC98926
0.8581	High Similarity	NPC311144
0.8581	High Similarity	NPC326500
0.8581	High Similarity	NPC304839
0.8581	High Similarity	NPC220582
0.8581	High Similarity	NPC271288
0.8562	High Similarity	NPC477272
0.8553	High Similarity	NPC148480
0.8552	High Similarity	NPC474504
0.8552	High Similarity	NPC470671
0.8552	High Similarity	NPC183639
0.8552	High Similarity	NPC474487
0.8552	High Similarity	NPC199458
0.8552	High Similarity	NPC254168
0.8552	High Similarity	NPC248995
0.8552	High Similarity	NPC272844
0.8552	High Similarity	NPC470672
0.8543	High Similarity	NPC321896
0.8543	High Similarity	NPC471115
0.8543	High Similarity	NPC29777
0.8543	High Similarity	NPC148423
0.8543	High Similarity	NPC135303
0.8543	High Similarity	NPC476185
0.8542	High Similarity	NPC470982
0.8542	High Similarity	NPC470983
0.8535	High Similarity	NPC155640
0.8535	High Similarity	NPC159508
0.8533	High Similarity	NPC168085
0.8526	High Similarity	NPC30655
0.8526	High Similarity	NPC45124
0.8526	High Similarity	NPC74854
0.8526	High Similarity	NPC304387
0.8523	High Similarity	NPC299011
0.8523	High Similarity	NPC477955
0.8523	High Similarity	NPC82534
0.8521	High Similarity	NPC15834
0.8521	High Similarity	NPC215875
0.8514	High Similarity	NPC24821
0.8514	High Similarity	NPC9117
0.8514	High Similarity	NPC112749
0.8514	High Similarity	NPC190637
0.8514	High Similarity	NPC212932
0.8514	High Similarity	NPC293053
0.8514	High Similarity	NPC113770
0.8514	High Similarity	NPC11700
0.8506	High Similarity	NPC137100
0.8503	High Similarity	NPC282300
0.8503	High Similarity	NPC476508
0.8503	High Similarity	NPC74397
0.8493	Intermediate Similarity	NPC216978
0.8493	Intermediate Similarity	NPC220062
0.8493	Intermediate Similarity	NPC477956
0.8493	Intermediate Similarity	NPC217186
0.8493	Intermediate Similarity	NPC301217
0.8493	Intermediate Similarity	NPC241975
0.8493	Intermediate Similarity	NPC96565
0.8493	Intermediate Similarity	NPC19476
0.8493	Intermediate Similarity	NPC55018
0.8493	Intermediate Similarity	NPC53181
0.8493	Intermediate Similarity	NPC303633
0.8491	Intermediate Similarity	NPC286230
0.8491	Intermediate Similarity	NPC476459
0.8491	Intermediate Similarity	NPC253730
0.8487	Intermediate Similarity	NPC290671
0.8483	Intermediate Similarity	NPC62735
0.8483	Intermediate Similarity	NPC474624
0.8483	Intermediate Similarity	NPC138047
0.8483	Intermediate Similarity	NPC131782
0.8481	Intermediate Similarity	NPC169471
0.8481	Intermediate Similarity	NPC329215
0.8481	Intermediate Similarity	NPC37183
0.8481	Intermediate Similarity	NPC204088
0.8481	Intermediate Similarity	NPC136641
0.8481	Intermediate Similarity	NPC259007
0.8472	Intermediate Similarity	NPC101752
0.8471	Intermediate Similarity	NPC3448
0.8471	Intermediate Similarity	NPC477239
0.8462	Intermediate Similarity	NPC16197
0.8456	Intermediate Similarity	NPC470673
0.8456	Intermediate Similarity	NPC470674
0.8456	Intermediate Similarity	NPC1886
0.8456	Intermediate Similarity	NPC117716
0.8456	Intermediate Similarity	NPC234629
0.8456	Intermediate Similarity	NPC216538
0.8456	Intermediate Similarity	NPC273538
0.8456	Intermediate Similarity	NPC224714
0.8456	Intermediate Similarity	NPC311741
0.8456	Intermediate Similarity	NPC196137
0.8456	Intermediate Similarity	NPC303185
0.8456	Intermediate Similarity	NPC184649
0.8456	Intermediate Similarity	NPC470890
0.8452	Intermediate Similarity	NPC270044
0.8446	Intermediate Similarity	NPC473042
0.8446	Intermediate Similarity	NPC200694
0.8446	Intermediate Similarity	NPC470556
0.8446	Intermediate Similarity	NPC144499
0.8442	Intermediate Similarity	NPC469934
0.8435	Intermediate Similarity	NPC172986

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 NPC172182 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	1029
0.2-0.3	1937
0.3-0.4	2823
0.4-0.5	1828
0.5-0.6	818
0.6-0.7	234
0.7-0.8	95
0.8-0.85	22
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD2800	Approved
0.8456	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6651	Approved
0.8333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD2344	Approved
0.8217	Intermediate Similarity	NPD3749	Approved
0.8212	Intermediate Similarity	NPD2533	Approved
0.8212	Intermediate Similarity	NPD2534	Approved
0.8212	Intermediate Similarity	NPD2532	Approved
0.8129	Intermediate Similarity	NPD7411	Suspended
0.8121	Intermediate Similarity	NPD1243	Approved
0.8105	Intermediate Similarity	NPD920	Approved
0.8063	Intermediate Similarity	NPD6959	Discontinued
0.8025	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2309	Approved
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD1240	Approved
0.7933	Intermediate Similarity	NPD1549	Phase 2
0.7857	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1510	Phase 2
0.7838	Intermediate Similarity	NPD1607	Approved
0.7834	Intermediate Similarity	NPD4380	Phase 2
0.7812	Intermediate Similarity	NPD3882	Suspended
0.7812	Intermediate Similarity	NPD7768	Phase 2
0.78	Intermediate Similarity	NPD2796	Approved
0.7799	Intermediate Similarity	NPD7819	Suspended
0.7799	Intermediate Similarity	NPD2801	Approved
0.7792	Intermediate Similarity	NPD1511	Approved
0.7778	Intermediate Similarity	NPD5494	Approved
0.7764	Intermediate Similarity	NPD7075	Discontinued
0.7763	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7473	Discontinued
0.7738	Intermediate Similarity	NPD6559	Discontinued
0.7736	Intermediate Similarity	NPD1934	Approved
0.7733	Intermediate Similarity	NPD2799	Discontinued
0.773	Intermediate Similarity	NPD1247	Approved
0.7727	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1512	Approved
0.7688	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6232	Discontinued
0.7636	Intermediate Similarity	NPD3926	Phase 2
0.7632	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6801	Discontinued
0.7597	Intermediate Similarity	NPD3750	Approved
0.7588	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5710	Approved
0.7576	Intermediate Similarity	NPD5711	Approved
0.7564	Intermediate Similarity	NPD6799	Approved
0.7547	Intermediate Similarity	NPD3226	Approved
0.7546	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD3818	Discontinued
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7286	Phase 2
0.7456	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7390	Discontinued
0.7451	Intermediate Similarity	NPD2935	Discontinued
0.745	Intermediate Similarity	NPD2313	Discontinued
0.7423	Intermediate Similarity	NPD2296	Approved
0.7403	Intermediate Similarity	NPD1471	Phase 3
0.7396	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD919	Approved
0.7386	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2403	Approved
0.7378	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5953	Discontinued
0.7338	Intermediate Similarity	NPD6100	Approved
0.7338	Intermediate Similarity	NPD6099	Approved
0.7338	Intermediate Similarity	NPD1551	Phase 2
0.7333	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4287	Approved
0.7317	Intermediate Similarity	NPD3817	Phase 2
0.729	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD3748	Approved
0.7262	Intermediate Similarity	NPD7229	Phase 3
0.7256	Intermediate Similarity	NPD1465	Phase 2
0.7251	Intermediate Similarity	NPD5844	Phase 1
0.7209	Intermediate Similarity	NPD7074	Phase 3
0.72	Intermediate Similarity	NPD4908	Phase 1
0.716	Intermediate Similarity	NPD6808	Phase 2
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7054	Approved
0.7127	Intermediate Similarity	NPD4361	Phase 2
0.7127	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD943	Approved
0.7114	Intermediate Similarity	NPD1203	Approved
0.711	Intermediate Similarity	NPD7472	Approved
0.711	Intermediate Similarity	NPD1729	Discontinued
0.7105	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6280	Approved
0.7091	Intermediate Similarity	NPD6279	Approved
0.7089	Intermediate Similarity	NPD2654	Approved
0.7083	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4363	Phase 3
0.7072	Intermediate Similarity	NPD4360	Phase 2
0.7069	Intermediate Similarity	NPD6797	Phase 2
0.7067	Intermediate Similarity	NPD2798	Approved
0.7044	Intermediate Similarity	NPD4628	Phase 3
0.7029	Intermediate Similarity	NPD7251	Discontinued
0.7022	Intermediate Similarity	NPD8434	Phase 2
0.7006	Intermediate Similarity	NPD5402	Approved
0.7	Intermediate Similarity	NPD2797	Approved
0.7	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD3266	Approved
0.6994	Remote Similarity	NPD5403	Approved
0.6993	Remote Similarity	NPD3764	Approved
0.6989	Remote Similarity	NPD7808	Phase 3
0.6989	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5124	Phase 1
0.6968	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1610	Phase 2
0.6946	Remote Similarity	NPD5761	Phase 2
0.6946	Remote Similarity	NPD5760	Phase 2
0.6928	Remote Similarity	NPD4625	Phase 3
0.6928	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1608	Approved
0.6913	Remote Similarity	NPD9717	Approved
0.6899	Remote Similarity	NPD5404	Approved
0.6899	Remote Similarity	NPD5406	Approved
0.6899	Remote Similarity	NPD5405	Approved
0.6899	Remote Similarity	NPD5408	Approved
0.689	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5401	Approved
0.6863	Remote Similarity	NPD6832	Phase 2
0.6855	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6005	Phase 3
0.6855	Remote Similarity	NPD6004	Phase 3
0.6855	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6002	Phase 3
0.6846	Remote Similarity	NPD422	Phase 1
0.6835	Remote Similarity	NPD7033	Discontinued
0.6832	Remote Similarity	NPD7003	Approved
0.6807	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7199	Phase 2
0.6786	Remote Similarity	NPD37	Approved
0.6784	Remote Similarity	NPD6234	Discontinued
0.6776	Remote Similarity	NPD1164	Approved
0.6768	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4966	Approved
0.6765	Remote Similarity	NPD4965	Approved
0.6765	Remote Similarity	NPD4967	Phase 2
0.676	Remote Similarity	NPD8313	Approved
0.676	Remote Similarity	NPD8312	Approved
0.6755	Remote Similarity	NPD4749	Approved
0.6752	Remote Similarity	NPD230	Phase 1
0.6752	Remote Similarity	NPD447	Suspended
0.6742	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.673	Remote Similarity	NPD651	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4308	Phase 3
0.6724	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3225	Approved
0.6711	Remote Similarity	NPD17	Approved
0.6707	Remote Similarity	NPD7458	Discontinued
0.6707	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4288	Approved
0.6689	Remote Similarity	NPD3972	Approved
0.6689	Remote Similarity	NPD1548	Phase 1
0.6688	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6585	Discontinued
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD3446	Phase 1
0.6646	Remote Similarity	NPD6355	Discontinued
0.6646	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5889	Approved
0.6627	Remote Similarity	NPD5890	Approved
0.6623	Remote Similarity	NPD1201	Approved
0.661	Remote Similarity	NPD3751	Discontinued
0.6605	Remote Similarity	NPD2424	Discontinued
0.6601	Remote Similarity	NPD1876	Approved
0.6598	Remote Similarity	NPD8151	Discontinued
0.6581	Remote Similarity	NPD2861	Phase 2
0.6571	Remote Similarity	NPD3787	Discontinued
0.6561	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1296	Phase 2
0.6561	Remote Similarity	NPD411	Approved
0.6556	Remote Similarity	NPD6104	Discontinued
0.6554	Remote Similarity	NPD7340	Approved
0.655	Remote Similarity	NPD8455	Phase 2
0.6527	Remote Similarity	NPD5049	Phase 3
0.6517	Remote Similarity	NPD7177	Discontinued

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