NPASS Compound

Structure

CID183345 OpenBabel06191715562D 22 23 0 0 0 0 0 0 0 0999 V2000 4.1497 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1497 -0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6599 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6599 0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 -0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 -0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 -0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 -0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4898 1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6599 -1.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 -1.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 0.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 1.4375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 -1.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4898 2.3958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3198 0.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 6 8 1 0 0 0 0 6 16 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 13 14 1 0 0 0 0 14 20 2 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.04
Volume:	288.687
LogP:	3.189
LogD:	1.501
LogS:	-3.907
# Rotatable Bonds:	4
TPSA:	132.13
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	2.58
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.755
MDCK Permeability:	5.248596607998479e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.155
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	96.55937194824219%
Volume Distribution (VD):	0.447
Pgp-substrate:	2.932243585586548%

ADMET: Metabolism

CYP1A2-inhibitor:	0.353
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.489
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.046

ADMET: Excretion

Clearance (CL):	1.106
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.801
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.755
Carcinogencity:	0.111
Eye Corrosion:	0.006
Eye Irritation:	0.949
Respiratory Toxicity:	0.381

Download Data

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

Natural Product: NPC183345

Natural Product ID:	NPC183345
*Common Name:**	4-(2,6-Dihydroxybenzoyl)-3-Formyl-5-Hydroxybenzoic Acid
IUPAC Name:	4-(2,6-dihydroxybenzoyl)-3-formyl-5-hydroxybenzoic acid
Synonyms:	TAN-931
Standard InCHIKey:	INVAPAXTQZQLGN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O7/c16-6-8-4-7(15(21)22)5-11(19)12(8)14(20)13-9(17)2-1-3-10(13)18/h1-6,17-19H,(H,21,22)
SMILES:	O=Cc1cc(cc(c1C(=O)c1c(O)cccc1O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823113
PubChem CID:	130935
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2010354]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21879714]
NPO29948	Penicillium purpurogenum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32293887]

☑ 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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	58600.0	nM	PMID[479720]

☑ 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 NPC183345 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	372
0.1-0.2	1693
0.2-0.3	3894
0.3-0.4	10186
0.4-0.5	9208
0.5-0.6	4715
0.6-0.7	7363
0.7-0.8	4744
0.8-0.85	436
0.85-0.9	76
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9478	High Similarity	NPC161632
0.9281	High Similarity	NPC73061
0.9209	High Similarity	NPC290550
0.9118	High Similarity	NPC288089
0.9071	High Similarity	NPC187843
0.9065	High Similarity	NPC190457
0.9051	High Similarity	NPC278375
0.8971	High Similarity	NPC70622
0.8921	High Similarity	NPC53206
0.8921	High Similarity	NPC53414
0.8849	High Similarity	NPC118919
0.8849	High Similarity	NPC254847
0.8841	High Similarity	NPC44437
0.8841	High Similarity	NPC474519
0.8824	High Similarity	NPC199253
0.8824	High Similarity	NPC136588
0.8824	High Similarity	NPC31799
0.8824	High Similarity	NPC31539
0.8803	High Similarity	NPC204045
0.8803	High Similarity	NPC305845
0.8794	High Similarity	NPC242994
0.8794	High Similarity	NPC143438
0.8794	High Similarity	NPC26924
0.8794	High Similarity	NPC162939
0.8794	High Similarity	NPC138099
0.8786	High Similarity	NPC471905
0.8768	High Similarity	NPC48036
0.8767	High Similarity	NPC471907
0.875	High Similarity	NPC471906
0.875	High Similarity	NPC21599
0.875	High Similarity	NPC244691
0.875	High Similarity	NPC193703
0.8741	High Similarity	NPC135524
0.8741	High Similarity	NPC193555
0.8732	High Similarity	NPC181560
0.8732	High Similarity	NPC169452
0.8732	High Similarity	NPC99441
0.8732	High Similarity	NPC315578
0.8723	High Similarity	NPC4214
0.8705	High Similarity	NPC166480
0.8705	High Similarity	NPC282780
0.8686	High Similarity	NPC62219
0.8676	High Similarity	NPC282923
0.8671	High Similarity	NPC37530
0.8657	High Similarity	NPC236189
0.8633	High Similarity	NPC52407
0.8633	High Similarity	NPC267205
0.8623	High Similarity	NPC205992
0.8621	High Similarity	NPC48762
0.8611	High Similarity	NPC474961
0.86	High Similarity	NPC208806
0.8593	High Similarity	NPC103540
0.8581	High Similarity	NPC70764
0.8571	High Similarity	NPC474394
0.8562	High Similarity	NPC34482
0.8552	High Similarity	NPC66593
0.8551	High Similarity	NPC147757
0.8542	High Similarity	NPC246638
0.854	High Similarity	NPC95537
0.8529	High Similarity	NPC8745
0.8529	High Similarity	NPC160499
0.8521	High Similarity	NPC471452
0.8514	High Similarity	NPC2569
0.8514	High Similarity	NPC172329
0.8511	High Similarity	NPC290803
0.8503	High Similarity	NPC147250
0.8503	High Similarity	NPC470570
0.8503	High Similarity	NPC314437
0.85	High Similarity	NPC115458
0.85	High Similarity	NPC180261
0.85	High Similarity	NPC37299
0.8489	Intermediate Similarity	NPC93015
0.8487	Intermediate Similarity	NPC474861
0.8478	Intermediate Similarity	NPC476119
0.8478	Intermediate Similarity	NPC109123
0.8478	Intermediate Similarity	NPC99731
0.8477	Intermediate Similarity	NPC182921
0.8477	Intermediate Similarity	NPC474824
0.8477	Intermediate Similarity	NPC218870
0.8477	Intermediate Similarity	NPC470408
0.8472	Intermediate Similarity	NPC203063
0.8467	Intermediate Similarity	NPC39819
0.8456	Intermediate Similarity	NPC10926
0.8451	Intermediate Similarity	NPC191976
0.8451	Intermediate Similarity	NPC86524
0.8451	Intermediate Similarity	NPC158481
0.8451	Intermediate Similarity	NPC272268
0.8446	Intermediate Similarity	NPC119767
0.8444	Intermediate Similarity	NPC375356
0.8431	Intermediate Similarity	NPC263483
0.8429	Intermediate Similarity	NPC478190
0.8425	Intermediate Similarity	NPC238629
0.8414	Intermediate Similarity	NPC110810
0.8414	Intermediate Similarity	NPC470842
0.8406	Intermediate Similarity	NPC41263
0.84	Intermediate Similarity	NPC315520
0.84	Intermediate Similarity	NPC119929
0.84	Intermediate Similarity	NPC205766
0.84	Intermediate Similarity	NPC255641
0.84	Intermediate Similarity	NPC147735
0.84	Intermediate Similarity	NPC290954
0.8394	Intermediate Similarity	NPC231774
0.8394	Intermediate Similarity	NPC3224
0.8394	Intermediate Similarity	NPC96915
0.8392	Intermediate Similarity	NPC305060
0.8387	Intermediate Similarity	NPC24761
0.8382	Intermediate Similarity	NPC152525
0.8382	Intermediate Similarity	NPC173978
0.8382	Intermediate Similarity	NPC68756
0.8382	Intermediate Similarity	NPC13238
0.8382	Intermediate Similarity	NPC142956
0.8378	Intermediate Similarity	NPC163846
0.8378	Intermediate Similarity	NPC225173
0.8378	Intermediate Similarity	NPC300540
0.837	Intermediate Similarity	NPC300274
0.837	Intermediate Similarity	NPC283514
0.837	Intermediate Similarity	NPC307174
0.8369	Intermediate Similarity	NPC213485
0.8369	Intermediate Similarity	NPC40524
0.8369	Intermediate Similarity	NPC139074
0.8369	Intermediate Similarity	NPC314048
0.8367	Intermediate Similarity	NPC151607
0.8367	Intermediate Similarity	NPC42540
0.8357	Intermediate Similarity	NPC85342
0.8357	Intermediate Similarity	NPC275504
0.8357	Intermediate Similarity	NPC41847
0.8356	Intermediate Similarity	NPC257644
0.8356	Intermediate Similarity	NPC474300
0.8356	Intermediate Similarity	NPC471733
0.8356	Intermediate Similarity	NPC137649
0.8345	Intermediate Similarity	NPC92624
0.8345	Intermediate Similarity	NPC34414
0.8345	Intermediate Similarity	NPC155205
0.8345	Intermediate Similarity	NPC278928
0.8345	Intermediate Similarity	NPC146647
0.8345	Intermediate Similarity	NPC225243
0.8333	Intermediate Similarity	NPC61590
0.8333	Intermediate Similarity	NPC13715
0.8333	Intermediate Similarity	NPC9121
0.8333	Intermediate Similarity	NPC177307
0.8323	Intermediate Similarity	NPC143050
0.8322	Intermediate Similarity	NPC289042
0.8322	Intermediate Similarity	NPC56433
0.8322	Intermediate Similarity	NPC245584
0.8322	Intermediate Similarity	NPC37709
0.8322	Intermediate Similarity	NPC125801
0.8322	Intermediate Similarity	NPC474813
0.8322	Intermediate Similarity	NPC126767
0.8322	Intermediate Similarity	NPC118027
0.8322	Intermediate Similarity	NPC190648
0.8322	Intermediate Similarity	NPC315275
0.8322	Intermediate Similarity	NPC71055
0.8322	Intermediate Similarity	NPC312929
0.8321	Intermediate Similarity	NPC262671
0.8321	Intermediate Similarity	NPC201728
0.831	Intermediate Similarity	NPC12070
0.8301	Intermediate Similarity	NPC149618
0.8301	Intermediate Similarity	NPC89625
0.8301	Intermediate Similarity	NPC66029
0.8299	Intermediate Similarity	NPC471731
0.8299	Intermediate Similarity	NPC159721
0.8299	Intermediate Similarity	NPC476473
0.8299	Intermediate Similarity	NPC471682
0.8298	Intermediate Similarity	NPC242358
0.8298	Intermediate Similarity	NPC309430
0.8298	Intermediate Similarity	NPC110609
0.8298	Intermediate Similarity	NPC246693
0.8298	Intermediate Similarity	NPC58685
0.8296	Intermediate Similarity	NPC198336
0.8289	Intermediate Similarity	NPC281272
0.8288	Intermediate Similarity	NPC257003
0.8286	Intermediate Similarity	NPC55949
0.8286	Intermediate Similarity	NPC259942
0.8286	Intermediate Similarity	NPC17840
0.8286	Intermediate Similarity	NPC247477
0.8286	Intermediate Similarity	NPC198305
0.8284	Intermediate Similarity	NPC294964
0.8278	Intermediate Similarity	NPC470107
0.8278	Intermediate Similarity	NPC470568
0.8278	Intermediate Similarity	NPC294646
0.8276	Intermediate Similarity	NPC92655
0.8276	Intermediate Similarity	NPC216312
0.8276	Intermediate Similarity	NPC275356
0.8276	Intermediate Similarity	NPC471602
0.8276	Intermediate Similarity	NPC29771
0.8276	Intermediate Similarity	NPC306835
0.8276	Intermediate Similarity	NPC256463
0.8276	Intermediate Similarity	NPC299405
0.8276	Intermediate Similarity	NPC295339
0.8276	Intermediate Similarity	NPC476477
0.8276	Intermediate Similarity	NPC111422
0.8273	Intermediate Similarity	NPC48248
0.8273	Intermediate Similarity	NPC179898
0.8267	Intermediate Similarity	NPC153417
0.8267	Intermediate Similarity	NPC5537
0.8264	Intermediate Similarity	NPC474849
0.8264	Intermediate Similarity	NPC178467
0.8264	Intermediate Similarity	NPC474771
0.8264	Intermediate Similarity	NPC149372
0.8264	Intermediate Similarity	NPC62272

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 NPC183345 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	957
0.2-0.3	1654
0.3-0.4	2818
0.4-0.5	1983
0.5-0.6	966
0.6-0.7	301
0.7-0.8	97
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8849	High Similarity	NPD1509	Clinical (unspecified phase)
0.8593	High Similarity	NPD1470	Approved
0.8296	Intermediate Similarity	NPD1201	Approved
0.8264	Intermediate Similarity	NPD5408	Approved
0.8264	Intermediate Similarity	NPD5404	Approved
0.8264	Intermediate Similarity	NPD5406	Approved
0.8264	Intermediate Similarity	NPD5405	Approved
0.8169	Intermediate Similarity	NPD943	Approved
0.8138	Intermediate Similarity	NPD1551	Phase 2
0.8121	Intermediate Similarity	NPD7390	Discontinued
0.8092	Intermediate Similarity	NPD3226	Approved
0.7987	Intermediate Similarity	NPD6232	Discontinued
0.7985	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7473	Discontinued
0.7947	Intermediate Similarity	NPD2534	Approved
0.7947	Intermediate Similarity	NPD2532	Approved
0.7947	Intermediate Similarity	NPD2533	Approved
0.7945	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1164	Approved
0.7885	Intermediate Similarity	NPD7819	Suspended
0.7838	Intermediate Similarity	NPD2346	Discontinued
0.7823	Intermediate Similarity	NPD1510	Phase 2
0.7808	Intermediate Similarity	NPD1607	Approved
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2935	Discontinued
0.7712	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1240	Approved
0.7566	Intermediate Similarity	NPD3750	Approved
0.755	Intermediate Similarity	NPD1549	Phase 2
0.7532	Intermediate Similarity	NPD7411	Suspended
0.7519	Intermediate Similarity	NPD74	Approved
0.7519	Intermediate Similarity	NPD9266	Approved
0.75	Intermediate Similarity	NPD920	Approved
0.7485	Intermediate Similarity	NPD6959	Discontinued
0.7484	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4380	Phase 2
0.7465	Intermediate Similarity	NPD9269	Phase 2
0.7464	Intermediate Similarity	NPD9493	Approved
0.7444	Intermediate Similarity	NPD9264	Approved
0.7444	Intermediate Similarity	NPD9267	Approved
0.7444	Intermediate Similarity	NPD9263	Approved
0.7438	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD9268	Approved
0.7415	Intermediate Similarity	NPD2313	Discontinued
0.7407	Intermediate Similarity	NPD3749	Approved
0.7407	Intermediate Similarity	NPD7075	Discontinued
0.7396	Intermediate Similarity	NPD6559	Discontinued
0.7383	Intermediate Similarity	NPD230	Phase 1
0.7358	Intermediate Similarity	NPD6599	Discontinued
0.7355	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7768	Phase 2
0.7333	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD5711	Approved
0.7329	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5844	Phase 1
0.7314	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1203	Approved
0.7308	Intermediate Similarity	NPD1511	Approved
0.7297	Intermediate Similarity	NPD3764	Approved
0.7296	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5402	Approved
0.7284	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8150	Discontinued
0.7267	Intermediate Similarity	NPD1934	Approved
0.7255	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3300	Phase 2
0.7237	Intermediate Similarity	NPD2799	Discontinued
0.7237	Intermediate Similarity	NPD3748	Approved
0.7215	Intermediate Similarity	NPD1512	Approved
0.7209	Intermediate Similarity	NPD8313	Approved
0.7209	Intermediate Similarity	NPD8312	Approved
0.7197	Intermediate Similarity	NPD6799	Approved
0.7194	Intermediate Similarity	NPD9281	Approved
0.7161	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6801	Discontinued
0.7152	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD9261	Approved
0.7135	Intermediate Similarity	NPD5953	Discontinued
0.7134	Intermediate Similarity	NPD3882	Suspended
0.7134	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1283	Approved
0.7117	Intermediate Similarity	NPD1465	Phase 2
0.7117	Intermediate Similarity	NPD2801	Approved
0.7115	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2796	Approved
0.7073	Intermediate Similarity	NPD3817	Phase 2
0.7071	Intermediate Similarity	NPD5951	Approved
0.7067	Intermediate Similarity	NPD411	Approved
0.7066	Intermediate Similarity	NPD1247	Approved
0.7063	Intermediate Similarity	NPD5403	Approved
0.7059	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3818	Discontinued
0.7051	Intermediate Similarity	NPD1243	Approved
0.7051	Intermediate Similarity	NPD2800	Approved
0.7044	Intermediate Similarity	NPD5401	Approved
0.7039	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD447	Suspended
0.702	Intermediate Similarity	NPD520	Approved
0.7018	Intermediate Similarity	NPD7286	Phase 2
0.7013	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7003	Approved
0.7006	Intermediate Similarity	NPD5494	Approved
0.7006	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9545	Approved
0.6986	Remote Similarity	NPD9717	Approved
0.6957	Remote Similarity	NPD4750	Phase 3
0.6944	Remote Similarity	NPD6534	Approved
0.6944	Remote Similarity	NPD6535	Approved
0.6933	Remote Similarity	NPD6832	Phase 2
0.6923	Remote Similarity	NPD2344	Approved
0.6923	Remote Similarity	NPD1471	Phase 3
0.6919	Remote Similarity	NPD7435	Discontinued
0.6918	Remote Similarity	NPD1281	Approved
0.6913	Remote Similarity	NPD2798	Approved
0.6903	Remote Similarity	NPD4308	Phase 3
0.6899	Remote Similarity	NPD3400	Discontinued
0.6899	Remote Similarity	NPD4628	Phase 3
0.6893	Remote Similarity	NPD8434	Phase 2
0.6882	Remote Similarity	NPD8320	Phase 1
0.6882	Remote Similarity	NPD8319	Approved
0.6871	Remote Similarity	NPD7458	Discontinued
0.6859	Remote Similarity	NPD6100	Approved
0.6859	Remote Similarity	NPD6099	Approved
0.6857	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6777	Approved
0.6848	Remote Similarity	NPD6778	Approved
0.6848	Remote Similarity	NPD6776	Approved
0.6848	Remote Similarity	NPD6779	Approved
0.6848	Remote Similarity	NPD6780	Approved
0.6848	Remote Similarity	NPD6782	Approved
0.6848	Remote Similarity	NPD37	Approved
0.6848	Remote Similarity	NPD6781	Approved
0.6842	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3268	Approved
0.6842	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6166	Phase 2
0.6842	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7700	Phase 2
0.6831	Remote Similarity	NPD7699	Phase 2
0.6828	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8151	Discontinued
0.6821	Remote Similarity	NPD6020	Phase 2
0.6821	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1932	Approved
0.6812	Remote Similarity	NPD2342	Discontinued
0.6809	Remote Similarity	NPD7635	Approved
0.6809	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6212	Phase 3
0.6796	Remote Similarity	NPD6213	Phase 3
0.6796	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7074	Phase 3
0.6781	Remote Similarity	NPD2932	Approved
0.6781	Remote Similarity	NPD3019	Approved
0.6781	Remote Similarity	NPD4626	Approved
0.6781	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4625	Phase 3
0.6776	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6651	Approved
0.6765	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1929	Approved
0.6765	Remote Similarity	NPD1930	Approved
0.6763	Remote Similarity	NPD3751	Discontinued
0.6763	Remote Similarity	NPD7177	Discontinued
0.6757	Remote Similarity	NPD1608	Approved
0.6753	Remote Similarity	NPD2979	Phase 3
0.675	Remote Similarity	NPD6190	Approved
0.675	Remote Similarity	NPD2309	Approved
0.6746	Remote Similarity	NPD6234	Discontinued
0.6743	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD1242	Phase 1
0.6738	Remote Similarity	NPD7698	Approved
0.6738	Remote Similarity	NPD7697	Approved
0.6738	Remote Similarity	NPD7696	Phase 3
0.6732	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4966	Approved
0.6726	Remote Similarity	NPD4965	Approved
0.6726	Remote Similarity	NPD4967	Phase 2
0.6725	Remote Similarity	NPD7229	Phase 3
0.6724	Remote Similarity	NPD7054	Approved
0.6715	Remote Similarity	NPD1237	Approved
0.6712	Remote Similarity	NPD1651	Approved
0.6702	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7874	Approved
0.6702	Remote Similarity	NPD7870	Phase 2
0.6702	Remote Similarity	NPD7871	Phase 2
0.6689	Remote Similarity	NPD1019	Discontinued
0.6688	Remote Similarity	NPD6663	Approved
0.6687	Remote Similarity	NPD8166	Discontinued
0.6686	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD7893	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