NPASS Compound

Structure

NPC474614 OpenBabel07101719152D 21 22 0 0 0 0 0 0 0 0999 V2000 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -3.4641 1.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 1 8 1 0 0 0 0 2 6 2 0 0 0 0 2 9 1 0 0 0 0 3 6 1 0 0 0 0 3 10 2 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 7 1 0 0 0 0 5 17 1 0 0 0 0 7 8 1 0 0 0 0 8 12 2 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	417.91
Volume:	300.287
LogP:	3.057
LogD:	1.719
LogS:	-2.699
# Rotatable Bonds:	3
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.492
Synthetic Accessibility Score:	2.875
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.274
MDCK Permeability:	1.191815590573242e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.332
20% Bioavailability (F20%):	0.754
30% Bioavailability (F30%):	0.066

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	99.13526153564453%
Volume Distribution (VD):	0.404
Pgp-substrate:	1.0241382122039795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.48
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.312
CYP2C9-substrate:	0.249
CYP2D6-inhibitor:	0.51
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	5.65
Half-life (T1/2):	0.956

ADMET: Toxicity

hERG Blockers:	0.242
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.705
AMES Toxicity:	0.236
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.955
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.919
Respiratory Toxicity:	0.072

Download Data

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

Natural Product: NPC474614

Natural Product ID:	NPC474614
*Common Name:**	5'-Hydroxyisoavrainvilleol
IUPAC Name:	3-bromo-4-[(3-bromo-4,5-dihydroxyphenyl)methyl]-5-(hydroxymethyl)benzene-1,2-diol
Synonyms:	5'-Hydroxyisoavrainvilleol
Standard InCHIKey:	SEXYDDXUERLOFL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12Br2O5/c15-9-2-6(3-10(18)13(9)20)1-8-7(5-17)4-11(19)14(21)12(8)16/h2-4,17-21H,1,5H2
SMILES:	OCc1cc(O)c(c(c1Cc1cc(O)c(c(c1)Br)O)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476883
PubChem CID:	3081007
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180830]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3668556]
NPO17785	Avrainvillea nigricans	Species	Udoteaceae	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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	9.0	mm	PMID[475036]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	10.0	mm	PMID[475036]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	11.0	mm	PMID[475036]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.0	mm	PMID[475036]

☑ 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 NPC474614 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	545
0.1-0.2	2070
0.2-0.3	7733
0.3-0.4	12911
0.4-0.5	6315
0.5-0.6	9623
0.6-0.7	3280
0.7-0.8	179
0.8-0.85	20
0.85-0.9	12
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9683	High Similarity	NPC163560
0.9449	High Similarity	NPC300678
0.9237	High Similarity	NPC156356
0.9167	High Similarity	NPC160932
0.916	High Similarity	NPC224663
0.9098	High Similarity	NPC38483
0.903	High Similarity	NPC89341
0.9008	High Similarity	NPC312155
0.8968	High Similarity	NPC137117
0.8898	High Similarity	NPC220311
0.8871	High Similarity	NPC474146
0.8852	High Similarity	NPC79844
0.8841	High Similarity	NPC88896
0.8832	High Similarity	NPC109346
0.881	High Similarity	NPC47790
0.8779	High Similarity	NPC43613
0.873	High Similarity	NPC136543
0.8722	High Similarity	NPC245386
0.8692	High Similarity	NPC150929
0.8647	High Similarity	NPC244890
0.8538	High Similarity	NPC43706
0.8516	High Similarity	NPC229213
0.8485	Intermediate Similarity	NPC85049
0.8473	Intermediate Similarity	NPC13004
0.8473	Intermediate Similarity	NPC474147
0.8473	Intermediate Similarity	NPC473708
0.8455	Intermediate Similarity	NPC471485
0.845	Intermediate Similarity	NPC473572
0.845	Intermediate Similarity	NPC474169
0.8421	Intermediate Similarity	NPC226493
0.8421	Intermediate Similarity	NPC160081
0.8394	Intermediate Similarity	NPC271942
0.8394	Intermediate Similarity	NPC168680
0.8264	Intermediate Similarity	NPC7398
0.8235	Intermediate Similarity	NPC471328
0.8214	Intermediate Similarity	NPC118794
0.8168	Intermediate Similarity	NPC84606
0.8092	Intermediate Similarity	NPC219444
0.8077	Intermediate Similarity	NPC227976
0.8049	Intermediate Similarity	NPC471495
0.8029	Intermediate Similarity	NPC303011
0.8	Intermediate Similarity	NPC472071
0.7953	Intermediate Similarity	NPC120280
0.7923	Intermediate Similarity	NPC117759
0.792	Intermediate Similarity	NPC473358
0.791	Intermediate Similarity	NPC142776
0.7891	Intermediate Similarity	NPC152947
0.784	Intermediate Similarity	NPC54543
0.7803	Intermediate Similarity	NPC470414
0.7778	Intermediate Similarity	NPC226401
0.7778	Intermediate Similarity	NPC79793
0.7778	Intermediate Similarity	NPC147634
0.7778	Intermediate Similarity	NPC174096
0.7778	Intermediate Similarity	NPC120982
0.7752	Intermediate Similarity	NPC472893
0.7724	Intermediate Similarity	NPC12278
0.7724	Intermediate Similarity	NPC471511
0.7721	Intermediate Similarity	NPC134219
0.7717	Intermediate Similarity	NPC179002
0.7717	Intermediate Similarity	NPC187583
0.7717	Intermediate Similarity	NPC257430
0.7712	Intermediate Similarity	NPC38980
0.7698	Intermediate Similarity	NPC55617
0.7698	Intermediate Similarity	NPC62258
0.7697	Intermediate Similarity	NPC474535
0.7681	Intermediate Similarity	NPC474536
0.7661	Intermediate Similarity	NPC239291
0.7647	Intermediate Similarity	NPC475697
0.7638	Intermediate Similarity	NPC471487
0.7619	Intermediate Similarity	NPC233835
0.7597	Intermediate Similarity	NPC471488
0.7578	Intermediate Similarity	NPC268032
0.7561	Intermediate Similarity	NPC110764
0.7559	Intermediate Similarity	NPC473372
0.7559	Intermediate Similarity	NPC228343
0.7559	Intermediate Similarity	NPC254833
0.7554	Intermediate Similarity	NPC105702
0.7538	Intermediate Similarity	NPC94217
0.7537	Intermediate Similarity	NPC471486
0.75	Intermediate Similarity	NPC473451
0.7481	Intermediate Similarity	NPC50782
0.748	Intermediate Similarity	NPC223393
0.7462	Intermediate Similarity	NPC33244
0.7415	Intermediate Similarity	NPC184632
0.7398	Intermediate Similarity	NPC131587
0.7394	Intermediate Similarity	NPC474135
0.7388	Intermediate Similarity	NPC217174
0.7388	Intermediate Similarity	NPC176893
0.7376	Intermediate Similarity	NPC473724
0.7361	Intermediate Similarity	NPC199089
0.7357	Intermediate Similarity	NPC214553
0.7353	Intermediate Similarity	NPC237667
0.7353	Intermediate Similarity	NPC39029
0.7344	Intermediate Similarity	NPC105727
0.7344	Intermediate Similarity	NPC58427
0.7344	Intermediate Similarity	NPC114392
0.7344	Intermediate Similarity	NPC34864
0.7333	Intermediate Similarity	NPC113862
0.7333	Intermediate Similarity	NPC475245
0.7328	Intermediate Similarity	NPC76400
0.7319	Intermediate Similarity	NPC146355
0.7319	Intermediate Similarity	NPC257682
0.7319	Intermediate Similarity	NPC131747
0.7317	Intermediate Similarity	NPC109955
0.7302	Intermediate Similarity	NPC323810
0.7302	Intermediate Similarity	NPC120719
0.7299	Intermediate Similarity	NPC85488
0.7299	Intermediate Similarity	NPC471794
0.7286	Intermediate Similarity	NPC106511
0.7286	Intermediate Similarity	NPC165045
0.7286	Intermediate Similarity	NPC476536
0.7286	Intermediate Similarity	NPC5428
0.7286	Intermediate Similarity	NPC118533
0.7273	Intermediate Similarity	NPC12656
0.7273	Intermediate Similarity	NPC473137
0.7266	Intermediate Similarity	NPC148627
0.7266	Intermediate Similarity	NPC176527
0.7259	Intermediate Similarity	NPC109371
0.7259	Intermediate Similarity	NPC470214
0.7259	Intermediate Similarity	NPC470215
0.7252	Intermediate Similarity	NPC471179
0.7246	Intermediate Similarity	NPC280704
0.7246	Intermediate Similarity	NPC471693
0.7246	Intermediate Similarity	NPC53567
0.7239	Intermediate Similarity	NPC277588
0.7239	Intermediate Similarity	NPC610
0.7239	Intermediate Similarity	NPC175799
0.7239	Intermediate Similarity	NPC145023
0.7239	Intermediate Similarity	NPC278652
0.7239	Intermediate Similarity	NPC200988
0.7234	Intermediate Similarity	NPC277458
0.7234	Intermediate Similarity	NPC472968
0.7234	Intermediate Similarity	NPC307050
0.7206	Intermediate Similarity	NPC34634
0.7206	Intermediate Similarity	NPC265454
0.7197	Intermediate Similarity	NPC264558
0.7194	Intermediate Similarity	NPC224342
0.7188	Intermediate Similarity	NPC477814
0.7185	Intermediate Similarity	NPC144343
0.7185	Intermediate Similarity	NPC86198
0.7183	Intermediate Similarity	NPC475875
0.7177	Intermediate Similarity	NPC32674
0.7176	Intermediate Similarity	NPC297657
0.7176	Intermediate Similarity	NPC308689
0.7174	Intermediate Similarity	NPC321402
0.7174	Intermediate Similarity	NPC296202
0.7172	Intermediate Similarity	NPC311256
0.7163	Intermediate Similarity	NPC231607
0.7163	Intermediate Similarity	NPC108659
0.7163	Intermediate Similarity	NPC79715
0.7163	Intermediate Similarity	NPC264900
0.7154	Intermediate Similarity	NPC274678
0.7153	Intermediate Similarity	NPC207613
0.7143	Intermediate Similarity	NPC33654
0.7133	Intermediate Similarity	NPC174495
0.7133	Intermediate Similarity	NPC64201
0.7133	Intermediate Similarity	NPC187998
0.7133	Intermediate Similarity	NPC145305
0.7133	Intermediate Similarity	NPC92164
0.7133	Intermediate Similarity	NPC77040
0.7133	Intermediate Similarity	NPC143483
0.7133	Intermediate Similarity	NPC242807
0.7133	Intermediate Similarity	NPC42300
0.7133	Intermediate Similarity	NPC257582
0.7133	Intermediate Similarity	NPC153739
0.7133	Intermediate Similarity	NPC241522
0.7132	Intermediate Similarity	NPC191866
0.7132	Intermediate Similarity	NPC181969
0.7132	Intermediate Similarity	NPC320987
0.7132	Intermediate Similarity	NPC70084
0.7122	Intermediate Similarity	NPC84086
0.7113	Intermediate Similarity	NPC474178
0.7113	Intermediate Similarity	NPC21867
0.7113	Intermediate Similarity	NPC128208
0.7113	Intermediate Similarity	NPC282703
0.7113	Intermediate Similarity	NPC252307
0.7113	Intermediate Similarity	NPC11258
0.7113	Intermediate Similarity	NPC184733
0.7113	Intermediate Similarity	NPC45774
0.7113	Intermediate Similarity	NPC245826
0.7113	Intermediate Similarity	NPC129570
0.7111	Intermediate Similarity	NPC293619
0.7103	Intermediate Similarity	NPC474453
0.7101	Intermediate Similarity	NPC470212
0.7101	Intermediate Similarity	NPC54872
0.7101	Intermediate Similarity	NPC184651
0.7101	Intermediate Similarity	NPC472271
0.7101	Intermediate Similarity	NPC473853
0.7101	Intermediate Similarity	NPC147654
0.7101	Intermediate Similarity	NPC262156
0.7101	Intermediate Similarity	NPC343720
0.7101	Intermediate Similarity	NPC266045
0.7101	Intermediate Similarity	NPC476343
0.7101	Intermediate Similarity	NPC113865
0.7101	Intermediate Similarity	NPC7830
0.7101	Intermediate Similarity	NPC324571
0.7101	Intermediate Similarity	NPC312675
0.7099	Intermediate Similarity	NPC44732
0.7092	Intermediate Similarity	NPC58607
0.7092	Intermediate Similarity	NPC191037

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 NPC474614 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	465
0.1-0.2	1038
0.2-0.3	2217
0.3-0.4	3112
0.4-0.5	1489
0.5-0.6	724
0.6-0.7	102
0.7-0.8	3
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
0.7559	Intermediate Similarity	NPD3022	Approved
0.7559	Intermediate Similarity	NPD3021	Approved
0.7063	Intermediate Similarity	NPD3027	Phase 3
0.6957	Remote Similarity	NPD9381	Approved
0.6957	Remote Similarity	NPD9384	Approved
0.6918	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1613	Approved
0.6901	Remote Similarity	NPD3094	Phase 2
0.6899	Remote Similarity	NPD9244	Approved
0.6871	Remote Similarity	NPD4010	Discontinued
0.6857	Remote Similarity	NPD3092	Approved
0.685	Remote Similarity	NPD3020	Approved
0.6842	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3059	Approved
0.6803	Remote Similarity	NPD3062	Approved
0.6803	Remote Similarity	NPD3061	Approved
0.6797	Remote Similarity	NPD1242	Phase 1
0.6791	Remote Similarity	NPD228	Approved
0.6761	Remote Similarity	NPD9622	Approved
0.6759	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2859	Approved
0.6746	Remote Similarity	NPD2860	Approved
0.6711	Remote Similarity	NPD5314	Approved
0.6691	Remote Similarity	NPD3091	Approved
0.6689	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD2933	Approved
0.6667	Remote Similarity	NPD2934	Approved
0.6621	Remote Similarity	NPD9620	Approved
0.6621	Remote Similarity	NPD9619	Approved
0.6621	Remote Similarity	NPD9621	Approved
0.6618	Remote Similarity	NPD9379	Approved
0.6618	Remote Similarity	NPD9377	Approved
0.6569	Remote Similarity	NPD5283	Phase 1
0.6554	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7266	Discontinued
0.6535	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD7635	Approved
0.6493	Remote Similarity	NPD2342	Discontinued
0.649	Remote Similarity	NPD817	Approved
0.649	Remote Similarity	NPD823	Approved
0.6486	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3095	Discontinued
0.6467	Remote Similarity	NPD943	Approved
0.6456	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD597	Approved
0.6443	Remote Similarity	NPD598	Approved
0.6443	Remote Similarity	NPD601	Approved
0.6438	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD288	Approved
0.6414	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1130	Approved
0.64	Remote Similarity	NPD1136	Approved
0.64	Remote Similarity	NPD1132	Approved
0.6397	Remote Similarity	NPD4750	Phase 3
0.6389	Remote Similarity	NPD3705	Approved
0.637	Remote Similarity	NPD5310	Approved
0.637	Remote Similarity	NPD5311	Approved
0.6364	Remote Similarity	NPD940	Approved
0.6364	Remote Similarity	NPD846	Approved
0.6364	Remote Similarity	NPD2286	Discontinued
0.6364	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4060	Phase 1
0.6357	Remote Similarity	NPD844	Approved
0.6352	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD2861	Phase 2
0.6331	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD3055	Approved
0.6327	Remote Similarity	NPD3053	Approved
0.6303	Remote Similarity	NPD4288	Approved
0.6299	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4093	Discontinued
0.6277	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD1792	Phase 2
0.6276	Remote Similarity	NPD1201	Approved
0.6276	Remote Similarity	NPD1610	Phase 2
0.6267	Remote Similarity	NPD9718	Approved
0.6266	Remote Similarity	NPD6190	Approved
0.6258	Remote Similarity	NPD9570	Approved
0.625	Remote Similarity	NPD1558	Phase 1
0.625	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2932	Approved
0.625	Remote Similarity	NPD3019	Approved
0.625	Remote Similarity	NPD4059	Approved
0.6242	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD9269	Phase 2
0.6233	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD1809	Phase 2
0.6216	Remote Similarity	NPD1470	Approved
0.621	Remote Similarity	NPD111	Approved
0.6209	Remote Similarity	NPD230	Phase 1
0.6203	Remote Similarity	NPD8166	Discontinued
0.6176	Remote Similarity	NPD968	Approved
0.6174	Remote Similarity	NPD257	Approved
0.6174	Remote Similarity	NPD258	Approved
0.617	Remote Similarity	NPD497	Approved
0.6149	Remote Similarity	NPD3645	Discontinued
0.6149	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD826	Approved
0.6144	Remote Similarity	NPD825	Approved
0.6139	Remote Similarity	NPD3060	Approved
0.6138	Remote Similarity	NPD1751	Approved
0.6133	Remote Similarity	NPD5736	Approved
0.6127	Remote Similarity	NPD7157	Approved
0.6111	Remote Similarity	NPD1548	Phase 1
0.6107	Remote Similarity	NPD4103	Phase 2
0.6107	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD5735	Approved
0.6099	Remote Similarity	NPD2234	Approved
0.6099	Remote Similarity	NPD2229	Approved
0.6099	Remote Similarity	NPD2228	Approved
0.6099	Remote Similarity	NPD498	Approved
0.6099	Remote Similarity	NPD495	Approved
0.6099	Remote Similarity	NPD496	Approved
0.6095	Remote Similarity	NPD6234	Discontinued
0.6093	Remote Similarity	NPD4908	Phase 1
0.6087	Remote Similarity	NPD2684	Approved
0.6084	Remote Similarity	NPD37	Approved
0.6081	Remote Similarity	NPD4659	Approved
0.6077	Remote Similarity	NPD845	Approved
0.6071	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD1357	Approved
0.6065	Remote Similarity	NPD2568	Approved
0.6058	Remote Similarity	NPD1445	Approved
0.6058	Remote Similarity	NPD1444	Approved
0.6056	Remote Similarity	NPD9614	Approved
0.6056	Remote Similarity	NPD9618	Approved
0.6056	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6688	Approved
0.6047	Remote Similarity	NPD6687	Approved
0.6045	Remote Similarity	NPD3028	Approved
0.604	Remote Similarity	NPD1283	Approved
0.6039	Remote Similarity	NPD2238	Phase 2
0.6038	Remote Similarity	NPD6674	Discontinued
0.6028	Remote Similarity	NPD7843	Approved
0.6026	Remote Similarity	NPD9569	Approved
0.6025	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD3845	Phase 1
0.6014	Remote Similarity	NPD1840	Phase 2
0.6014	Remote Similarity	NPD2562	Approved
0.6014	Remote Similarity	NPD2561	Approved
0.6013	Remote Similarity	NPD5109	Approved
0.6013	Remote Similarity	NPD5111	Phase 2
0.6013	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD3764	Approved
0.6013	Remote Similarity	NPD5110	Phase 2
0.6012	Remote Similarity	NPD2296	Approved
0.6	Remote Similarity	NPD555	Phase 2
0.6	Remote Similarity	NPD4005	Discontinued
0.5988	Remote Similarity	NPD1511	Approved
0.5988	Remote Similarity	NPD1934	Approved
0.5988	Remote Similarity	NPD2420	Approved
0.5988	Remote Similarity	NPD2421	Approved
0.5987	Remote Similarity	NPD1169	Approved
0.5987	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD4966	Approved
0.5976	Remote Similarity	NPD4967	Phase 2
0.5976	Remote Similarity	NPD4965	Approved
0.5974	Remote Similarity	NPD6407	Approved
0.5974	Remote Similarity	NPD6663	Approved
0.5974	Remote Similarity	NPD259	Phase 1
0.5974	Remote Similarity	NPD6405	Approved
0.5973	Remote Similarity	NPD2983	Phase 2
0.5973	Remote Similarity	NPD2982	Phase 2
0.5973	Remote Similarity	NPD1669	Approved
0.5963	Remote Similarity	NPD2677	Approved
0.5963	Remote Similarity	NPD5241	Discontinued
0.596	Remote Similarity	NPD6584	Phase 3
0.596	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD9268	Approved
0.5959	Remote Similarity	NPD1651	Approved
0.5956	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD2977	Approved
0.5952	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD2978	Approved
0.5948	Remote Similarity	NPD9537	Phase 1
0.5948	Remote Similarity	NPD9536	Phase 1
0.5948	Remote Similarity	NPD4625	Phase 3
0.5943	Remote Similarity	NPD7228	Approved
0.5938	Remote Similarity	NPD9094	Approved
0.5936	Remote Similarity	NPD8095	Phase 1
0.5931	Remote Similarity	NPD317	Approved
0.5931	Remote Similarity	NPD9615	Approved
0.5931	Remote Similarity	NPD5536	Phase 2
0.5931	Remote Similarity	NPD9616	Approved
0.5931	Remote Similarity	NPD856	Approved
0.5931	Remote Similarity	NPD9613	Approved
0.5931	Remote Similarity	NPD16	Approved
0.5931	Remote Similarity	NPD318	Approved
0.5924	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD4538	Approved
0.5924	Remote Similarity	NPD4536	Approved
0.5921	Remote Similarity	NPD9494	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data