NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.1
Volume:	226.298
LogP:	0.409
LogD:	1.348
LogS:	-1.304
# Rotatable Bonds:	5
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.589
Synthetic Accessibility Score:	3.153
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.443
MDCK Permeability:	1.8299118892173283e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.059
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.108
30% Bioavailability (F30%):	0.081

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.374
Plasma Protein Binding (PPB):	49.22415542602539%
Volume Distribution (VD):	1.261
Pgp-substrate:	50.681732177734375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.777
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.366
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.246
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.379
CYP3A4-inhibitor:	0.06
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	9.159
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.649
Rat Oral Acute Toxicity:	0.152
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.931
Carcinogencity:	0.188
Eye Corrosion:	0.006
Eye Irritation:	0.892
Respiratory Toxicity:	0.057

Download Data

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

Natural Product: NPC477803

Natural Product ID:	NPC477803
*Common Name:**	4-(1,2,2-Trimethoxyethyl)benzene-1,2-diol
IUPAC Name:	4-(1,2,2-trimethoxyethyl)benzene-1,2-diol
Synonyms:
Standard InCHIKey:	GJZGSHAHIYNSKQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H16O5/c1-14-10(11(15-2)16-3)7-4-5-8(12)9(13)6-7/h4-6,10-13H,1-3H3
SMILES:	COC(C1=CC(=C(C=C1)O)O)C(OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10013990
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002542] Benzylethers

*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
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	Vanuatu islands	n.a.	PMID[10924170]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277766]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640526]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326327]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	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
IC50	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	28.7	ug/ml	PMID[18407691]
NPT2	Others	Unspecified		IC50	>	200	ug/ml	PMID[18407691]

☑ 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 NPC477803 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	290
0.1-0.2	1545
0.2-0.3	4505
0.3-0.4	12087
0.4-0.5	6661
0.5-0.6	6894
0.6-0.7	7486
0.7-0.8	2799
0.8-0.85	394
0.85-0.9	34
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9068	High Similarity	NPC266045
0.8974	High Similarity	NPC181969
0.8974	High Similarity	NPC320987
0.8952	High Similarity	NPC65942
0.8952	High Similarity	NPC248307
0.8908	High Similarity	NPC470804
0.8898	High Similarity	NPC148615
0.8898	High Similarity	NPC35071
0.8898	High Similarity	NPC177475
0.8889	High Similarity	NPC255675
0.8814	High Similarity	NPC135961
0.879	High Similarity	NPC307110
0.877	High Similarity	NPC90318
0.875	High Similarity	NPC476343
0.874	High Similarity	NPC35731
0.874	High Similarity	NPC470881
0.873	High Similarity	NPC471505
0.873	High Similarity	NPC254275
0.8718	High Similarity	NPC221049
0.8718	High Similarity	NPC175771
0.8678	High Similarity	NPC209567
0.8661	High Similarity	NPC6836
0.864	High Similarity	NPC270849
0.864	High Similarity	NPC26653
0.864	High Similarity	NPC166040
0.8629	High Similarity	NPC231607
0.8629	High Similarity	NPC79715
0.8629	High Similarity	NPC264900
0.8629	High Similarity	NPC108659
0.8621	High Similarity	NPC264558
0.8607	High Similarity	NPC220598
0.8607	High Similarity	NPC471693
0.8607	High Similarity	NPC165375
0.8605	High Similarity	NPC199459
0.8605	High Similarity	NPC52277
0.8605	High Similarity	NPC177035
0.8594	High Similarity	NPC107478
0.8583	High Similarity	NPC106739
0.8583	High Similarity	NPC252833
0.8583	High Similarity	NPC470270
0.8571	High Similarity	NPC80600
0.8571	High Similarity	NPC472024
0.856	High Similarity	NPC148982
0.856	High Similarity	NPC232880
0.8559	High Similarity	NPC148055
0.8548	High Similarity	NPC191037
0.8548	High Similarity	NPC178284
0.8548	High Similarity	NPC58607
0.8548	High Similarity	NPC94179
0.8547	High Similarity	NPC157338
0.8547	High Similarity	NPC313193
0.8538	High Similarity	NPC304152
0.8538	High Similarity	NPC470413
0.8538	High Similarity	NPC138738
0.8527	High Similarity	NPC101624
0.8527	High Similarity	NPC135777
0.8527	High Similarity	NPC184938
0.8527	High Similarity	NPC142547
0.8516	High Similarity	NPC132895
0.8512	High Similarity	NPC470414
0.85	High Similarity	NPC311595
0.85	High Similarity	NPC24474
0.8492	Intermediate Similarity	NPC184092
0.8492	Intermediate Similarity	NPC477294
0.8492	Intermediate Similarity	NPC229784
0.8492	Intermediate Similarity	NPC248355
0.8492	Intermediate Similarity	NPC477293
0.8487	Intermediate Similarity	NPC164386
0.8482	Intermediate Similarity	NPC12278
0.848	Intermediate Similarity	NPC292056
0.848	Intermediate Similarity	NPC118533
0.848	Intermediate Similarity	NPC476873
0.848	Intermediate Similarity	NPC118787
0.848	Intermediate Similarity	NPC165045
0.848	Intermediate Similarity	NPC147821
0.848	Intermediate Similarity	NPC111247
0.848	Intermediate Similarity	NPC41706
0.848	Intermediate Similarity	NPC183181
0.848	Intermediate Similarity	NPC163332
0.848	Intermediate Similarity	NPC319625
0.8468	Intermediate Similarity	NPC194519
0.8468	Intermediate Similarity	NPC148627
0.8455	Intermediate Similarity	NPC473451
0.845	Intermediate Similarity	NPC886
0.845	Intermediate Similarity	NPC287597
0.845	Intermediate Similarity	NPC34293
0.8448	Intermediate Similarity	NPC173746
0.8448	Intermediate Similarity	NPC156840
0.8448	Intermediate Similarity	NPC8547
0.8448	Intermediate Similarity	NPC257124
0.8443	Intermediate Similarity	NPC49341
0.8438	Intermediate Similarity	NPC473285
0.8425	Intermediate Similarity	NPC275950
0.8417	Intermediate Similarity	NPC309434
0.8413	Intermediate Similarity	NPC11258
0.8413	Intermediate Similarity	NPC245826
0.8413	Intermediate Similarity	NPC282703
0.8413	Intermediate Similarity	NPC184733
0.8413	Intermediate Similarity	NPC21867
0.8413	Intermediate Similarity	NPC128208
0.8413	Intermediate Similarity	NPC474178
0.8413	Intermediate Similarity	NPC45774
0.8413	Intermediate Similarity	NPC302378
0.8413	Intermediate Similarity	NPC252307
0.8413	Intermediate Similarity	NPC129570
0.84	Intermediate Similarity	NPC473960
0.8397	Intermediate Similarity	NPC78363
0.8387	Intermediate Similarity	NPC94276
0.8387	Intermediate Similarity	NPC131747
0.8387	Intermediate Similarity	NPC257682
0.8387	Intermediate Similarity	NPC146355
0.8387	Intermediate Similarity	NPC109822
0.8372	Intermediate Similarity	NPC25821
0.8372	Intermediate Similarity	NPC254398
0.8361	Intermediate Similarity	NPC207613
0.8359	Intermediate Similarity	NPC166168
0.8359	Intermediate Similarity	NPC476345
0.8359	Intermediate Similarity	NPC219677
0.8359	Intermediate Similarity	NPC9912
0.8347	Intermediate Similarity	NPC20674
0.8346	Intermediate Similarity	NPC134405
0.8346	Intermediate Similarity	NPC472711
0.8346	Intermediate Similarity	NPC5851
0.8346	Intermediate Similarity	NPC476385
0.8346	Intermediate Similarity	NPC476968
0.8346	Intermediate Similarity	NPC170844
0.8346	Intermediate Similarity	NPC86030
0.8333	Intermediate Similarity	NPC293619
0.8333	Intermediate Similarity	NPC472350
0.8333	Intermediate Similarity	NPC123526
0.8333	Intermediate Similarity	NPC81515
0.8333	Intermediate Similarity	NPC197316
0.8333	Intermediate Similarity	NPC5428
0.8333	Intermediate Similarity	NPC88640
0.8333	Intermediate Similarity	NPC89105
0.8333	Intermediate Similarity	NPC64141
0.8333	Intermediate Similarity	NPC68092
0.8333	Intermediate Similarity	NPC193666
0.8333	Intermediate Similarity	NPC476383
0.8321	Intermediate Similarity	NPC157554
0.8319	Intermediate Similarity	NPC233669
0.8308	Intermediate Similarity	NPC187194
0.8308	Intermediate Similarity	NPC48863
0.8308	Intermediate Similarity	NPC251981
0.8308	Intermediate Similarity	NPC13745
0.8308	Intermediate Similarity	NPC471883
0.8306	Intermediate Similarity	NPC212176
0.8304	Intermediate Similarity	NPC110764
0.8295	Intermediate Similarity	NPC473924
0.8295	Intermediate Similarity	NPC147616
0.8295	Intermediate Similarity	NPC259742
0.8295	Intermediate Similarity	NPC104077
0.8295	Intermediate Similarity	NPC299144
0.8295	Intermediate Similarity	NPC219671
0.8293	Intermediate Similarity	NPC312675
0.8293	Intermediate Similarity	NPC473853
0.8293	Intermediate Similarity	NPC343720
0.8293	Intermediate Similarity	NPC470212
0.8293	Intermediate Similarity	NPC324571
0.8293	Intermediate Similarity	NPC113865
0.8293	Intermediate Similarity	NPC184651
0.8293	Intermediate Similarity	NPC262156
0.8293	Intermediate Similarity	NPC147654
0.8293	Intermediate Similarity	NPC54872
0.8291	Intermediate Similarity	NPC78918
0.8291	Intermediate Similarity	NPC139617
0.8284	Intermediate Similarity	NPC140502
0.8284	Intermediate Similarity	NPC189115
0.8284	Intermediate Similarity	NPC222433
0.8284	Intermediate Similarity	NPC469559
0.8284	Intermediate Similarity	NPC48309
0.8284	Intermediate Similarity	NPC265648
0.8284	Intermediate Similarity	NPC253878
0.8281	Intermediate Similarity	NPC142985
0.8281	Intermediate Similarity	NPC187998
0.8281	Intermediate Similarity	NPC181079
0.8281	Intermediate Similarity	NPC42300
0.8281	Intermediate Similarity	NPC145305
0.8281	Intermediate Similarity	NPC143483
0.8281	Intermediate Similarity	NPC64201
0.8281	Intermediate Similarity	NPC242807
0.8281	Intermediate Similarity	NPC153739
0.8281	Intermediate Similarity	NPC257582
0.8281	Intermediate Similarity	NPC174495
0.8281	Intermediate Similarity	NPC92164
0.8281	Intermediate Similarity	NPC77040
0.8281	Intermediate Similarity	NPC241522
0.8281	Intermediate Similarity	NPC173308
0.8279	Intermediate Similarity	NPC229401
0.8279	Intermediate Similarity	NPC469702
0.8279	Intermediate Similarity	NPC282409
0.8276	Intermediate Similarity	NPC246358
0.8276	Intermediate Similarity	NPC233731
0.8276	Intermediate Similarity	NPC36108
0.8276	Intermediate Similarity	NPC7097
0.8271	Intermediate Similarity	NPC473799
0.8271	Intermediate Similarity	NPC475530
0.8271	Intermediate Similarity	NPC106944
0.8268	Intermediate Similarity	NPC98631
0.8268	Intermediate Similarity	NPC72529

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 NPC477803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	901
0.2-0.3	1947
0.3-0.4	2873
0.4-0.5	1604
0.5-0.6	1048
0.6-0.7	444
0.7-0.8	64
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8448	Intermediate Similarity	NPD228	Approved
0.8346	Intermediate Similarity	NPD3027	Phase 3
0.8333	Intermediate Similarity	NPD7266	Discontinued
0.8197	Intermediate Similarity	NPD1357	Approved
0.8145	Intermediate Similarity	NPD3705	Approved
0.7966	Intermediate Similarity	NPD3022	Approved
0.7966	Intermediate Similarity	NPD3021	Approved
0.7879	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1613	Approved
0.7857	Intermediate Similarity	NPD1091	Approved
0.771	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD9381	Approved
0.7698	Intermediate Similarity	NPD9384	Approved
0.7634	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1653	Approved
0.7603	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD9622	Approved
0.7597	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5283	Phase 1
0.7556	Intermediate Similarity	NPD230	Phase 1
0.7438	Intermediate Similarity	NPD2684	Approved
0.7424	Intermediate Similarity	NPD9619	Approved
0.7424	Intermediate Similarity	NPD9621	Approved
0.7424	Intermediate Similarity	NPD9620	Approved
0.741	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2978	Approved
0.7365	Intermediate Similarity	NPD2977	Approved
0.7353	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3620	Phase 2
0.7353	Intermediate Similarity	NPD1558	Phase 1
0.7339	Intermediate Similarity	NPD9377	Approved
0.7339	Intermediate Similarity	NPD7843	Approved
0.7339	Intermediate Similarity	NPD9379	Approved
0.7333	Intermediate Similarity	NPD598	Approved
0.7333	Intermediate Similarity	NPD601	Approved
0.7333	Intermediate Similarity	NPD597	Approved
0.7324	Intermediate Similarity	NPD6190	Approved
0.7305	Intermediate Similarity	NPD6674	Discontinued
0.7304	Intermediate Similarity	NPD2934	Approved
0.7304	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD2933	Approved
0.7302	Intermediate Similarity	NPD7157	Approved
0.7286	Intermediate Similarity	NPD1375	Discontinued
0.7279	Intermediate Similarity	NPD1130	Approved
0.7279	Intermediate Similarity	NPD1136	Approved
0.7279	Intermediate Similarity	NPD1132	Approved
0.7279	Intermediate Similarity	NPD2674	Phase 3
0.7241	Intermediate Similarity	NPD2859	Approved
0.7241	Intermediate Similarity	NPD2860	Approved
0.7241	Intermediate Similarity	NPD844	Approved
0.7239	Intermediate Similarity	NPD2861	Phase 2
0.7239	Intermediate Similarity	NPD9494	Approved
0.7227	Intermediate Similarity	NPD846	Approved
0.7227	Intermediate Similarity	NPD940	Approved
0.7226	Intermediate Similarity	NPD3061	Approved
0.7226	Intermediate Similarity	NPD3062	Approved
0.7226	Intermediate Similarity	NPD3059	Approved
0.7222	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD290	Approved
0.7203	Intermediate Similarity	NPD3020	Approved
0.7197	Intermediate Similarity	NPD2983	Phase 2
0.7197	Intermediate Similarity	NPD2982	Phase 2
0.7183	Intermediate Similarity	NPD3060	Approved
0.7171	Intermediate Similarity	NPD6234	Discontinued
0.7155	Intermediate Similarity	NPD9296	Approved
0.7153	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1242	Phase 1
0.7143	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9545	Approved
0.7122	Intermediate Similarity	NPD5314	Approved
0.7121	Intermediate Similarity	NPD2981	Phase 2
0.7117	Intermediate Similarity	NPD111	Approved
0.7111	Intermediate Similarity	NPD3018	Phase 2
0.7101	Intermediate Similarity	NPD4060	Phase 1
0.7101	Intermediate Similarity	NPD825	Approved
0.7101	Intermediate Similarity	NPD826	Approved
0.709	Intermediate Similarity	NPD3094	Phase 2
0.708	Intermediate Similarity	NPD3145	Approved
0.708	Intermediate Similarity	NPD3144	Approved
0.7073	Intermediate Similarity	NPD1358	Approved
0.7067	Intermediate Similarity	NPD37	Approved
0.7063	Intermediate Similarity	NPD4236	Phase 3
0.7063	Intermediate Similarity	NPD4237	Approved
0.7055	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5536	Phase 2
0.7045	Intermediate Similarity	NPD3092	Approved
0.7034	Intermediate Similarity	NPD288	Approved
0.7031	Intermediate Similarity	NPD6671	Approved
0.7027	Intermediate Similarity	NPD3687	Approved
0.7027	Intermediate Similarity	NPD3686	Approved
0.7025	Intermediate Similarity	NPD7054	Approved
0.7023	Intermediate Similarity	NPD5126	Approved
0.7023	Intermediate Similarity	NPD5125	Phase 3
0.7	Intermediate Similarity	NPD823	Approved
0.7	Intermediate Similarity	NPD817	Approved
0.7	Intermediate Similarity	NPD1548	Phase 1
0.6992	Remote Similarity	NPD968	Approved
0.6984	Remote Similarity	NPD969	Suspended
0.6981	Remote Similarity	NPD7472	Approved
0.6981	Remote Similarity	NPD7074	Phase 3
0.6972	Remote Similarity	NPD9570	Approved
0.697	Remote Similarity	NPD3496	Discontinued
0.6962	Remote Similarity	NPD7228	Approved
0.6962	Remote Similarity	NPD3818	Discontinued
0.696	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1934	Approved
0.6942	Remote Similarity	NPD291	Approved
0.694	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6797	Phase 2
0.6934	Remote Similarity	NPD4908	Phase 1
0.6929	Remote Similarity	NPD821	Approved
0.6929	Remote Similarity	NPD555	Phase 2
0.6928	Remote Similarity	NPD4966	Approved
0.6928	Remote Similarity	NPD4965	Approved
0.6928	Remote Similarity	NPD4967	Phase 2
0.6918	Remote Similarity	NPD5058	Phase 3
0.6917	Remote Similarity	NPD1610	Phase 2
0.6912	Remote Similarity	NPD257	Approved
0.6912	Remote Similarity	NPD258	Approved
0.6908	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD259	Phase 1
0.6897	Remote Similarity	NPD8166	Discontinued
0.6894	Remote Similarity	NPD7251	Discontinued
0.6894	Remote Similarity	NPD4626	Approved
0.6894	Remote Similarity	NPD1778	Approved
0.6889	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8651	Approved
0.6879	Remote Similarity	NPD6653	Approved
0.687	Remote Similarity	NPD3091	Approved
0.6867	Remote Similarity	NPD3455	Phase 2
0.6866	Remote Similarity	NPD9269	Phase 2
0.6849	Remote Similarity	NPD2677	Approved
0.6838	Remote Similarity	NPD3053	Approved
0.6838	Remote Similarity	NPD3055	Approved
0.6835	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4538	Approved
0.6831	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4536	Approved
0.6828	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4750	Phase 3
0.6824	Remote Similarity	NPD4123	Phase 3
0.6822	Remote Similarity	NPD9618	Approved
0.6822	Remote Similarity	NPD9614	Approved
0.6818	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3685	Discontinued
0.6807	Remote Similarity	NPD1809	Phase 2
0.6797	Remote Similarity	NPD2801	Approved
0.6794	Remote Similarity	NPD16	Approved
0.6794	Remote Similarity	NPD856	Approved
0.6791	Remote Similarity	NPD422	Phase 1
0.679	Remote Similarity	NPD7685	Pre-registration
0.6788	Remote Similarity	NPD6584	Phase 3
0.6786	Remote Similarity	NPD6233	Phase 2
0.6786	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4110	Phase 3
0.6781	Remote Similarity	NPD4628	Phase 3
0.6781	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.678	Remote Similarity	NPD845	Approved
0.6765	Remote Similarity	NPD5311	Approved
0.6765	Remote Similarity	NPD5310	Approved
0.6763	Remote Similarity	NPD3179	Approved
0.6763	Remote Similarity	NPD3180	Approved
0.6763	Remote Similarity	NPD7095	Approved
0.6757	Remote Similarity	NPD1774	Approved
0.6757	Remote Similarity	NPD1511	Approved
0.6748	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7808	Phase 3
0.6741	Remote Similarity	NPD2231	Phase 2
0.6741	Remote Similarity	NPD2235	Phase 2
0.6739	Remote Similarity	NPD9569	Approved
0.6738	Remote Similarity	NPD2238	Phase 2
0.6736	Remote Similarity	NPD2161	Phase 2
0.6735	Remote Similarity	NPD2219	Phase 1
0.672	Remote Similarity	NPD1445	Approved
0.672	Remote Similarity	NPD1444	Approved
0.672	Remote Similarity	NPD3134	Approved
0.6714	Remote Similarity	NPD6798	Discontinued
0.6712	Remote Similarity	NPD1652	Phase 2
0.6712	Remote Similarity	NPD4162	Approved
0.6711	Remote Similarity	NPD4739	Approved
0.671	Remote Similarity	NPD3882	Suspended
0.6693	Remote Similarity	NPD556	Approved
0.6692	Remote Similarity	NPD5691	Approved
0.6691	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4749	Approved
0.669	Remote Similarity	NPD5762	Approved
0.669	Remote Similarity	NPD5735	Approved
0.669	Remote Similarity	NPD6355	Discontinued
0.669	Remote Similarity	NPD4340	Discontinued
0.669	Remote Similarity	NPD5763	Approved
0.6688	Remote Similarity	NPD5773	Approved
0.6688	Remote Similarity	NPD5772	Approved
0.6667	Remote Similarity	NPD9616	Approved
0.6667	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9613	Approved
0.6667	Remote Similarity	NPD4108	Discontinued
0.6667	Remote Similarity	NPD5960	Phase 3
0.6667	Remote Similarity	NPD4062	Phase 3

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