NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	215.94
Volume:	156.18
LogP:	1.425
LogD:	1.085
LogS:	-2.469
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	2.454
Fsp3:	0.0
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:	-4.745
MDCK Permeability:	1.605704346729908e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.074

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	92.23021697998047%
Volume Distribution (VD):	0.348
Pgp-substrate:	9.442561149597168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.823
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.359
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	3.208
Half-life (T1/2):	0.896

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.185
Skin Sensitization:	0.862
Carcinogencity:	0.127
Eye Corrosion:	0.969
Eye Irritation:	0.982
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC214553

Natural Product ID:	NPC214553
*Common Name:**	3-Bromo-4,5-Dihydroxybenzaldehyde
IUPAC Name:	3-bromo-4,5-dihydroxybenzaldehyde
Synonyms:
Standard InCHIKey:	GVSGSHGXUXLQNS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H5BrO3/c8-5-1-4(3-9)2-6(10)7(5)11/h1-3,10-11H
SMILES:	c1c(cc(c(c1Br)O)O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401368
PubChem CID:	85405
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000124] Aldehydes [CHEMONTID:0003213] Aryl-aldehydes [CHEMONTID:0001345] Benzaldehydes [CHEMONTID:0003978] Hydroxybenzaldehydes

*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
NPO28396	Rudbeckia laciniata	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0031-9422(98)00251-9]
NPO32930	polysiphonia lanosa	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387639]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17765551]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18088100]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18324823]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21875052]
NPO28396	Rudbeckia laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19169	Helichrysum caespititium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28396	Rudbeckia laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3778	Perityle emoryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15014	Senecio linearifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22076	Laurus novocanariensis	Species	Lauraceae	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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	27900.0	nM	PMID[507987]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	354200.0	nM	PMID[507988]
NPT35	Others	n.a.		IC50	=	20300.0	nM	PMID[507986]

☑ 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 NPC214553 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	452
0.1-0.2	2995
0.2-0.3	8994
0.3-0.4	11046
0.4-0.5	5633
0.5-0.6	10895
0.6-0.7	2533
0.7-0.8	138
0.8-0.85	3
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC474135
0.9453	High Similarity	NPC199089
0.9098	High Similarity	NPC250597
0.871	High Similarity	NPC100395
0.8689	High Similarity	NPC278102
0.8643	High Similarity	NPC473608
0.8561	High Similarity	NPC110800
0.8413	Intermediate Similarity	NPC117759
0.831	Intermediate Similarity	NPC178097
0.8175	Intermediate Similarity	NPC79844
0.797	Intermediate Similarity	NPC142776
0.7969	Intermediate Similarity	NPC150919
0.7969	Intermediate Similarity	NPC28169
0.7899	Intermediate Similarity	NPC471328
0.7869	Intermediate Similarity	NPC163734
0.7869	Intermediate Similarity	NPC219913
0.7852	Intermediate Similarity	NPC473787
0.7852	Intermediate Similarity	NPC203719
0.7852	Intermediate Similarity	NPC117237
0.7846	Intermediate Similarity	NPC156654
0.7832	Intermediate Similarity	NPC184632
0.7803	Intermediate Similarity	NPC136543
0.7786	Intermediate Similarity	NPC474146
0.7744	Intermediate Similarity	NPC47790
0.7744	Intermediate Similarity	NPC229213
0.771	Intermediate Similarity	NPC38483
0.7687	Intermediate Similarity	NPC473572
0.7687	Intermediate Similarity	NPC474169
0.7681	Intermediate Similarity	NPC298268
0.7661	Intermediate Similarity	NPC19149
0.763	Intermediate Similarity	NPC137117
0.7616	Intermediate Similarity	NPC294870
0.7612	Intermediate Similarity	NPC225710
0.7482	Intermediate Similarity	NPC226855
0.7465	Intermediate Similarity	NPC237330
0.7465	Intermediate Similarity	NPC144662
0.7464	Intermediate Similarity	NPC16651
0.7464	Intermediate Similarity	NPC32163
0.7464	Intermediate Similarity	NPC158654
0.7413	Intermediate Similarity	NPC274613
0.741	Intermediate Similarity	NPC150929
0.7391	Intermediate Similarity	NPC43706
0.7388	Intermediate Similarity	NPC180207
0.7357	Intermediate Similarity	NPC85049
0.7357	Intermediate Similarity	NPC474614
0.7338	Intermediate Similarity	NPC107672
0.7338	Intermediate Similarity	NPC473708
0.7338	Intermediate Similarity	NPC474147
0.7333	Intermediate Similarity	NPC295317
0.7328	Intermediate Similarity	NPC163154
0.7324	Intermediate Similarity	NPC50763
0.7319	Intermediate Similarity	NPC220311
0.731	Intermediate Similarity	NPC471236
0.731	Intermediate Similarity	NPC197766
0.7308	Intermediate Similarity	NPC231717
0.7305	Intermediate Similarity	NPC226493
0.7305	Intermediate Similarity	NPC160081
0.7286	Intermediate Similarity	NPC234175
0.7273	Intermediate Similarity	NPC156124
0.7273	Intermediate Similarity	NPC304929
0.7273	Intermediate Similarity	NPC1321
0.7273	Intermediate Similarity	NPC4665
0.7259	Intermediate Similarity	NPC260837
0.7254	Intermediate Similarity	NPC264145
0.7244	Intermediate Similarity	NPC305490
0.7244	Intermediate Similarity	NPC187913
0.7244	Intermediate Similarity	NPC6984
0.7241	Intermediate Similarity	NPC177967
0.7241	Intermediate Similarity	NPC471237
0.7234	Intermediate Similarity	NPC94810
0.7234	Intermediate Similarity	NPC261759
0.7234	Intermediate Similarity	NPC105702
0.7231	Intermediate Similarity	NPC114682
0.7231	Intermediate Similarity	NPC212718
0.7222	Intermediate Similarity	NPC79672
0.7222	Intermediate Similarity	NPC204582
0.7218	Intermediate Similarity	NPC61062
0.7218	Intermediate Similarity	NPC277394
0.7218	Intermediate Similarity	NPC299252
0.7214	Intermediate Similarity	NPC214620
0.7214	Intermediate Similarity	NPC324209
0.7206	Intermediate Similarity	NPC294361
0.7206	Intermediate Similarity	NPC236520
0.7203	Intermediate Similarity	NPC300678
0.7203	Intermediate Similarity	NPC111888
0.7188	Intermediate Similarity	NPC226699
0.7188	Intermediate Similarity	NPC29883
0.7188	Intermediate Similarity	NPC303264
0.7188	Intermediate Similarity	NPC34715
0.7183	Intermediate Similarity	NPC66905
0.7183	Intermediate Similarity	NPC117609
0.7179	Intermediate Similarity	NPC474535
0.7172	Intermediate Similarity	NPC139519
0.7172	Intermediate Similarity	NPC18646
0.7162	Intermediate Similarity	NPC476534
0.7154	Intermediate Similarity	NPC222084
0.7153	Intermediate Similarity	NPC239855
0.7153	Intermediate Similarity	NPC283823
0.7153	Intermediate Similarity	NPC163560
0.7153	Intermediate Similarity	NPC159418
0.7143	Intermediate Similarity	NPC50782
0.7134	Intermediate Similarity	NPC475697
0.7133	Intermediate Similarity	NPC34070
0.7133	Intermediate Similarity	NPC469526
0.7132	Intermediate Similarity	NPC17525
0.7123	Intermediate Similarity	NPC475111
0.7123	Intermediate Similarity	NPC156892
0.7121	Intermediate Similarity	NPC148969
0.7121	Intermediate Similarity	NPC11824
0.7113	Intermediate Similarity	NPC474536
0.7111	Intermediate Similarity	NPC283844
0.7109	Intermediate Similarity	NPC1786
0.7109	Intermediate Similarity	NPC1075
0.7109	Intermediate Similarity	NPC294902
0.7109	Intermediate Similarity	NPC184658
0.7103	Intermediate Similarity	NPC245386
0.7101	Intermediate Similarity	NPC86900
0.7097	Intermediate Similarity	NPC135103
0.7092	Intermediate Similarity	NPC13004
0.7087	Intermediate Similarity	NPC52087
0.7083	Intermediate Similarity	NPC135801
0.708	Intermediate Similarity	NPC216216
0.708	Intermediate Similarity	NPC227976
0.7077	Intermediate Similarity	NPC95172
0.7071	Intermediate Similarity	NPC120066
0.7071	Intermediate Similarity	NPC473626
0.7067	Intermediate Similarity	NPC299154
0.7063	Intermediate Similarity	NPC26697
0.7055	Intermediate Similarity	NPC208760
0.7045	Intermediate Similarity	NPC51698
0.704	Intermediate Similarity	NPC131587
0.7037	Intermediate Similarity	NPC230349
0.7037	Intermediate Similarity	NPC39793
0.7037	Intermediate Similarity	NPC174087
0.7034	Intermediate Similarity	NPC294226
0.7034	Intermediate Similarity	NPC474715
0.7029	Intermediate Similarity	NPC295034
0.7027	Intermediate Similarity	NPC239943
0.7027	Intermediate Similarity	NPC325625
0.7023	Intermediate Similarity	NPC116842
0.7014	Intermediate Similarity	NPC43613
0.7007	Intermediate Similarity	NPC324929
0.7007	Intermediate Similarity	NPC224663
0.7	Intermediate Similarity	NPC288945
0.7	Intermediate Similarity	NPC85565
0.6992	Remote Similarity	NPC95381
0.6985	Remote Similarity	NPC63126
0.698	Remote Similarity	NPC12218
0.698	Remote Similarity	NPC105525
0.698	Remote Similarity	NPC75763
0.698	Remote Similarity	NPC225036
0.698	Remote Similarity	NPC4796
0.6978	Remote Similarity	NPC139171
0.6978	Remote Similarity	NPC114298
0.6974	Remote Similarity	NPC275278
0.697	Remote Similarity	NPC226250
0.697	Remote Similarity	NPC268388
0.6959	Remote Similarity	NPC112068
0.6959	Remote Similarity	NPC156356
0.6959	Remote Similarity	NPC110899
0.6959	Remote Similarity	NPC25305
0.6959	Remote Similarity	NPC125417
0.6959	Remote Similarity	NPC95679
0.6957	Remote Similarity	NPC225245
0.6944	Remote Similarity	NPC285776
0.6944	Remote Similarity	NPC233056
0.694	Remote Similarity	NPC328593
0.694	Remote Similarity	NPC217472
0.694	Remote Similarity	NPC261453
0.694	Remote Similarity	NPC33749
0.694	Remote Similarity	NPC81808
0.6939	Remote Similarity	NPC72918
0.6935	Remote Similarity	NPC286006
0.6935	Remote Similarity	NPC107522
0.6934	Remote Similarity	NPC473767
0.6929	Remote Similarity	NPC242372
0.6929	Remote Similarity	NPC164778
0.6929	Remote Similarity	NPC4181
0.6929	Remote Similarity	NPC257976
0.6929	Remote Similarity	NPC110764
0.6928	Remote Similarity	NPC9370
0.6928	Remote Similarity	NPC287495
0.6923	Remote Similarity	NPC247250
0.6923	Remote Similarity	NPC767
0.6923	Remote Similarity	NPC3009
0.6923	Remote Similarity	NPC304747
0.6918	Remote Similarity	NPC244890
0.6918	Remote Similarity	NPC138472
0.6918	Remote Similarity	NPC111845
0.6918	Remote Similarity	NPC4170
0.6913	Remote Similarity	NPC141368
0.6913	Remote Similarity	NPC112135
0.6913	Remote Similarity	NPC160932
0.6913	Remote Similarity	NPC206207
0.6913	Remote Similarity	NPC175552
0.6908	Remote Similarity	NPC272868
0.6908	Remote Similarity	NPC122599
0.6908	Remote Similarity	NPC270848
0.6906	Remote Similarity	NPC120545
0.6906	Remote Similarity	NPC322332

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 NPC214553 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	472
0.1-0.2	1157
0.2-0.3	2350
0.3-0.4	3065
0.4-0.5	1542
0.5-0.6	499
0.6-0.7	59
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7852	Intermediate Similarity	NPD9494	Approved
0.7612	Intermediate Similarity	NPD9269	Phase 2
0.7313	Intermediate Similarity	NPD9268	Approved
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7188	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD943	Approved
0.6892	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD9545	Approved
0.6715	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2296	Approved
0.6617	Remote Similarity	NPD9266	Approved
0.6617	Remote Similarity	NPD74	Approved
0.6573	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD9244	Approved
0.6541	Remote Similarity	NPD9267	Approved
0.6541	Remote Similarity	NPD9264	Approved
0.6541	Remote Similarity	NPD9263	Approved
0.6531	Remote Similarity	NPD9718	Approved
0.6516	Remote Similarity	NPD6190	Approved
0.6497	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD824	Approved
0.6357	Remote Similarity	NPD9493	Approved
0.635	Remote Similarity	NPD228	Approved
0.6329	Remote Similarity	NPD1511	Approved
0.6327	Remote Similarity	NPD257	Approved
0.6327	Remote Similarity	NPD258	Approved
0.6324	Remote Similarity	NPD3021	Approved
0.6324	Remote Similarity	NPD3022	Approved
0.6303	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD3882	Suspended
0.6291	Remote Similarity	NPD825	Approved
0.6291	Remote Similarity	NPD826	Approved
0.6284	Remote Similarity	NPD9569	Approved
0.6277	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.627	Remote Similarity	NPD9258	Approved
0.627	Remote Similarity	NPD9256	Approved
0.6259	Remote Similarity	NPD1470	Approved
0.625	Remote Similarity	NPD555	Phase 2
0.625	Remote Similarity	NPD447	Suspended
0.625	Remote Similarity	NPD1512	Approved
0.6242	Remote Similarity	NPD8166	Discontinued
0.6241	Remote Similarity	NPD9261	Approved
0.6235	Remote Similarity	NPD3455	Phase 2
0.6234	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD259	Phase 1
0.622	Remote Similarity	NPD1934	Approved
0.6214	Remote Similarity	NPD9281	Approved
0.6207	Remote Similarity	NPD1201	Approved
0.62	Remote Similarity	NPD9536	Phase 1
0.62	Remote Similarity	NPD9537	Phase 1
0.6187	Remote Similarity	NPD9377	Approved
0.6187	Remote Similarity	NPD9379	Approved
0.6182	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD2801	Approved
0.6149	Remote Similarity	NPD1164	Approved
0.6145	Remote Similarity	NPD4288	Approved
0.6129	Remote Similarity	NPD1510	Phase 2
0.6129	Remote Similarity	NPD111	Approved
0.609	Remote Similarity	NPD9570	Approved
0.6084	Remote Similarity	NPD1465	Phase 2
0.6084	Remote Similarity	NPD5536	Phase 2
0.6078	Remote Similarity	NPD1240	Approved
0.6074	Remote Similarity	NPD1237	Approved
0.6069	Remote Similarity	NPD9381	Approved
0.6069	Remote Similarity	NPD9384	Approved
0.6053	Remote Similarity	NPD3764	Approved
0.6039	Remote Similarity	NPD274	Approved
0.6039	Remote Similarity	NPD275	Approved
0.6038	Remote Similarity	NPD4628	Phase 3
0.6028	Remote Similarity	NPD1241	Discontinued
0.6013	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1607	Approved
0.5987	Remote Similarity	NPD2935	Discontinued
0.5977	Remote Similarity	NPD3818	Discontinued
0.597	Remote Similarity	NPD1242	Phase 1
0.5959	Remote Similarity	NPD3019	Approved
0.5959	Remote Similarity	NPD2932	Approved
0.5952	Remote Similarity	NPD9259	Approved
0.5952	Remote Similarity	NPD9257	Approved
0.5949	Remote Similarity	NPD2344	Approved
0.5946	Remote Similarity	NPD3972	Approved
0.594	Remote Similarity	NPD9495	Approved
0.5932	Remote Similarity	NPD1298	Discontinued
0.5926	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD1549	Phase 2
0.5906	Remote Similarity	NPD9622	Approved
0.5906	Remote Similarity	NPD1755	Approved
0.5886	Remote Similarity	NPD1551	Phase 2
0.5876	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD1220	Phase 1
0.5862	Remote Similarity	NPD6166	Phase 2
0.5849	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7266	Discontinued
0.5844	Remote Similarity	NPD411	Approved
0.5843	Remote Similarity	NPD7685	Pre-registration
0.5839	Remote Similarity	NPD9717	Approved
0.5833	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2934	Approved
0.5833	Remote Similarity	NPD256	Approved
0.5833	Remote Similarity	NPD255	Approved
0.5833	Remote Similarity	NPD2933	Approved
0.5828	Remote Similarity	NPD1203	Approved
0.5815	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD4380	Phase 2
0.5806	Remote Similarity	NPD520	Approved
0.5802	Remote Similarity	NPD2309	Approved
0.5799	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.5793	Remote Similarity	NPD9568	Approved
0.5792	Remote Similarity	NPD4287	Approved
0.5789	Remote Similarity	NPD2860	Approved
0.5789	Remote Similarity	NPD844	Approved
0.5789	Remote Similarity	NPD9620	Approved
0.5789	Remote Similarity	NPD9619	Approved
0.5789	Remote Similarity	NPD9621	Approved
0.5789	Remote Similarity	NPD2859	Approved
0.5786	Remote Similarity	NPD5408	Approved
0.5786	Remote Similarity	NPD5404	Approved
0.5786	Remote Similarity	NPD5406	Approved
0.5786	Remote Similarity	NPD5405	Approved
0.5782	Remote Similarity	NPD1357	Approved
0.5778	Remote Similarity	NPD3020	Approved
0.5776	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.5774	Remote Similarity	NPD6385	Approved
0.5774	Remote Similarity	NPD6386	Approved
0.5767	Remote Similarity	NPD3300	Phase 2
0.5765	Remote Similarity	NPD3817	Phase 2
0.5763	Remote Similarity	NPD7054	Approved
0.5763	Remote Similarity	NPD1221	Approved
0.5762	Remote Similarity	NPD1283	Approved
0.5762	Remote Similarity	NPD1876	Approved
0.5756	Remote Similarity	NPD1168	Approved
0.5747	Remote Similarity	NPD1161	Approved
0.5747	Remote Similarity	NPD6232	Discontinued
0.5746	Remote Similarity	NPD288	Approved
0.5736	Remote Similarity	NPD9094	Approved
0.5735	Remote Similarity	NPD289	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD1608	Approved
0.5733	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD7390	Discontinued
0.573	Remote Similarity	NPD7074	Phase 3
0.573	Remote Similarity	NPD7472	Approved
0.5723	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1358	Approved
0.5705	Remote Similarity	NPD6663	Approved
0.5698	Remote Similarity	NPD6797	Phase 2
0.5697	Remote Similarity	NPD2533	Approved
0.5697	Remote Similarity	NPD2532	Approved
0.5697	Remote Similarity	NPD2534	Approved
0.569	Remote Similarity	NPD1247	Approved
0.5677	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.5677	Remote Similarity	NPD3027	Phase 3
0.5673	Remote Similarity	NPD5353	Approved
0.5669	Remote Similarity	NPD3140	Approved
0.5669	Remote Similarity	NPD3142	Approved
0.5669	Remote Similarity	NPD4445	Approved
0.5667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7251	Discontinued
0.5665	Remote Similarity	NPD919	Approved
0.5662	Remote Similarity	NPD1238	Approved
0.5658	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD5311	Approved
0.5658	Remote Similarity	NPD5310	Approved
0.5655	Remote Similarity	NPD7458	Discontinued
0.5652	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.565	Remote Similarity	NPD7473	Discontinued
0.5649	Remote Similarity	NPD5736	Approved
0.5646	Remote Similarity	NPD9092	Discovery
0.5644	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.5643	Remote Similarity	NPD3134	Approved
0.5641	Remote Similarity	NPD597	Approved
0.5641	Remote Similarity	NPD598	Approved
0.5641	Remote Similarity	NPD601	Approved
0.5639	Remote Similarity	NPD1202	Approved
0.5638	Remote Similarity	NPD1778	Approved
0.5636	Remote Similarity	NPD6799	Approved
0.5629	Remote Similarity	NPD1481	Phase 2
0.5625	Remote Similarity	NPD2799	Discontinued
0.5622	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.5621	Remote Similarity	NPD3053	Approved
0.5621	Remote Similarity	NPD3055	Approved
0.561	Remote Similarity	NPD2354	Approved
0.5608	Remote Similarity	NPD1894	Discontinued
0.5607	Remote Similarity	NPD7075	Discontinued
0.5607	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.5605	Remote Similarity	NPD1132	Approved
0.5605	Remote Similarity	NPD1130	Approved
0.5605	Remote Similarity	NPD1136	Approved
0.5602	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.5602	Remote Similarity	NPD642	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