NPASS Compound

Structure

NPC118794 OpenBabel07101718322D 32 34 0 0 0 0 0 0 0 0999 V2000 -2.5981 -1.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -1.7321 -1.0000 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 1.7321 2.0000 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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 7 1 0 0 0 0 2 6 1 0 0 0 0 2 8 1 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 16 2 0 0 0 0 7 17 1 0 0 0 0 8 16 1 0 0 0 0 8 18 2 0 0 0 0 9 19 2 0 0 0 0 9 26 1 0 0 0 0 10 20 2 0 0 0 0 10 27 1 0 0 0 0 11 13 2 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 19 1 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	759.66
Volume:	463.028
LogP:	6.24
LogD:	2.499
LogS:	-2.24
# Rotatable Bonds:	4
TPSA:	141.61
# H-Bond Aceptor:	7
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.148
Synthetic Accessibility Score:	3.36
Fsp3:	0.1
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	4
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.21
MDCK Permeability:	1.713239362288732e-05
Pgp-inhibitor:	0.661
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.57
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	103.99081420898438%
Volume Distribution (VD):	0.55
Pgp-substrate:	0.8440788984298706%

ADMET: Metabolism

CYP1A2-inhibitor:	0.309
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.591
CYP2C9-substrate:	0.411
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	1.782
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.053
Skin Sensitization:	0.976
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.921
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC118794

Natural Product ID:	NPC118794
*Common Name:**	Vidalol B
IUPAC Name:	2-bromo-4,6-bis[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]benzene-1,3,5-triol
Synonyms:
Standard InCHIKey:	KNHOTGMNAPTUGT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H13Br5O7/c21-11-5(3-9(26)19(31)13(11)23)1-7-16(28)8(18(30)15(25)17(7)29)2-6-4-10(27)20(32)14(24)12(6)22/h3-4,26-32H,1-2H2
SMILES:	C(c1cc(c(c(c1Br)Br)O)O)c1c(c(Cc2cc(c(c(c2Br)Br)O)O)c(c(c1O)Br)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477748
PubChem CID:	132037
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO32463	vidalia obtusaloba	Species	Tephritidae	Eukaryota	n.a.	Caribbean	n.a.	Database[Title]

☑ 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
Ki	4
Others	1

Activity Type	# Activity
Individual Protein	4
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1062	Individual Protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	1840.0	nM	PMID[489291]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	1130.0	nM	PMID[489291]
NPT1063	Individual Protein	Carbonic anhydrase VI	Homo sapiens	Ki	=	3410.0	nM	PMID[489291]
NPT24397	SINGLE PROTEIN	Phospholipase A2	Apis mellifera	Activity	=	96.0	%	PMID[489290]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	12240.0	nM	PMID[489291]

☑ 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 NPC118794 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	725
0.1-0.2	2828
0.2-0.3	12349
0.3-0.4	8802
0.4-0.5	5371
0.5-0.6	9968
0.6-0.7	2512
0.7-0.8	119
0.8-0.85	18
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC244890
0.8872	High Similarity	NPC220311
0.8571	High Similarity	NPC312155
0.85	High Similarity	NPC163560
0.8467	Intermediate Similarity	NPC13004
0.8435	Intermediate Similarity	NPC88896
0.8382	Intermediate Similarity	NPC137117
0.8357	Intermediate Similarity	NPC43613
0.8346	Intermediate Similarity	NPC38483
0.8322	Intermediate Similarity	NPC224663
0.831	Intermediate Similarity	NPC245386
0.8299	Intermediate Similarity	NPC109346
0.8273	Intermediate Similarity	NPC150929
0.8222	Intermediate Similarity	NPC471486
0.8219	Intermediate Similarity	NPC89341
0.8214	Intermediate Similarity	NPC474614
0.8207	Intermediate Similarity	NPC160932
0.8175	Intermediate Similarity	NPC84606
0.8102	Intermediate Similarity	NPC219444
0.8102	Intermediate Similarity	NPC47790
0.8042	Intermediate Similarity	NPC300678
0.8026	Intermediate Similarity	NPC7398
0.8014	Intermediate Similarity	NPC271942
0.7958	Intermediate Similarity	NPC85049
0.7926	Intermediate Similarity	NPC277588
0.7908	Intermediate Similarity	NPC152947
0.7902	Intermediate Similarity	NPC160081
0.7902	Intermediate Similarity	NPC226493
0.781	Intermediate Similarity	NPC191866
0.7801	Intermediate Similarity	NPC142776
0.777	Intermediate Similarity	NPC156356
0.777	Intermediate Similarity	NPC136543
0.773	Intermediate Similarity	NPC224342
0.7698	Intermediate Similarity	NPC24125
0.7671	Intermediate Similarity	NPC303011
0.7651	Intermediate Similarity	NPC168680
0.7643	Intermediate Similarity	NPC237667
0.763	Intermediate Similarity	NPC471488
0.7626	Intermediate Similarity	NPC474146
0.7612	Intermediate Similarity	NPC268032
0.7609	Intermediate Similarity	NPC144343
0.7591	Intermediate Similarity	NPC79844
0.7586	Intermediate Similarity	NPC474536
0.7537	Intermediate Similarity	NPC471487
0.7535	Intermediate Similarity	NPC53567
0.75	Intermediate Similarity	NPC471328
0.75	Intermediate Similarity	NPC43706
0.75	Intermediate Similarity	NPC474535
0.7466	Intermediate Similarity	NPC105702
0.7465	Intermediate Similarity	NPC229213
0.7463	Intermediate Similarity	NPC473372
0.7453	Intermediate Similarity	NPC475697
0.7448	Intermediate Similarity	NPC473708
0.7448	Intermediate Similarity	NPC474147
0.7447	Intermediate Similarity	NPC227976
0.7429	Intermediate Similarity	NPC217174
0.7426	Intermediate Similarity	NPC43525
0.7413	Intermediate Similarity	NPC474169
0.7413	Intermediate Similarity	NPC473572
0.7394	Intermediate Similarity	NPC39029
0.7391	Intermediate Similarity	NPC50782
0.7391	Intermediate Similarity	NPC472893
0.7388	Intermediate Similarity	NPC58427
0.7388	Intermediate Similarity	NPC105727
0.7388	Intermediate Similarity	NPC471495
0.7388	Intermediate Similarity	NPC114392
0.7388	Intermediate Similarity	NPC34864
0.7376	Intermediate Similarity	NPC472071
0.7372	Intermediate Similarity	NPC113862
0.7353	Intermediate Similarity	NPC476632
0.7353	Intermediate Similarity	NPC225679
0.7353	Intermediate Similarity	NPC165770
0.7353	Intermediate Similarity	NPC4493
0.7333	Intermediate Similarity	NPC54543
0.7329	Intermediate Similarity	NPC252131
0.7313	Intermediate Similarity	NPC176527
0.7305	Intermediate Similarity	NPC176893
0.7305	Intermediate Similarity	NPC117759
0.7279	Intermediate Similarity	NPC473358
0.7279	Intermediate Similarity	NPC28765
0.726	Intermediate Similarity	NPC134219
0.7254	Intermediate Similarity	NPC223451
0.7246	Intermediate Similarity	NPC33244
0.7246	Intermediate Similarity	NPC117846
0.7194	Intermediate Similarity	NPC107240
0.7194	Intermediate Similarity	NPC94217
0.719	Intermediate Similarity	NPC230919
0.719	Intermediate Similarity	NPC22902
0.719	Intermediate Similarity	NPC200935
0.719	Intermediate Similarity	NPC266453
0.7164	Intermediate Similarity	NPC292452
0.7143	Intermediate Similarity	NPC243759
0.7143	Intermediate Similarity	NPC105847
0.7143	Intermediate Similarity	NPC275061
0.7143	Intermediate Similarity	NPC220344
0.7143	Intermediate Similarity	NPC132804
0.7143	Intermediate Similarity	NPC243996
0.7143	Intermediate Similarity	NPC218131
0.7133	Intermediate Similarity	NPC15543
0.7133	Intermediate Similarity	NPC475245
0.7133	Intermediate Similarity	NPC69006
0.7132	Intermediate Similarity	NPC61885
0.7132	Intermediate Similarity	NPC63698
0.7105	Intermediate Similarity	NPC125649
0.7105	Intermediate Similarity	NPC66840
0.7105	Intermediate Similarity	NPC256307
0.7097	Intermediate Similarity	NPC73505
0.7097	Intermediate Similarity	NPC12668
0.7097	Intermediate Similarity	NPC295719
0.7097	Intermediate Similarity	NPC20520
0.7097	Intermediate Similarity	NPC34431
0.7097	Intermediate Similarity	NPC61783
0.7097	Intermediate Similarity	NPC308768
0.7097	Intermediate Similarity	NPC165026
0.7095	Intermediate Similarity	NPC324112
0.7095	Intermediate Similarity	NPC293054
0.7095	Intermediate Similarity	NPC5447
0.7095	Intermediate Similarity	NPC124452
0.7095	Intermediate Similarity	NPC169474
0.7095	Intermediate Similarity	NPC82679
0.7095	Intermediate Similarity	NPC159968
0.7095	Intermediate Similarity	NPC246620
0.7095	Intermediate Similarity	NPC250432
0.7095	Intermediate Similarity	NPC236791
0.7095	Intermediate Similarity	NPC282000
0.7095	Intermediate Similarity	NPC74817
0.7092	Intermediate Similarity	NPC261973
0.709	Intermediate Similarity	NPC102216
0.709	Intermediate Similarity	NPC30506
0.709	Intermediate Similarity	NPC471511
0.7078	Intermediate Similarity	NPC242715
0.7078	Intermediate Similarity	NPC56329
0.7078	Intermediate Similarity	NPC151656
0.7059	Intermediate Similarity	NPC199089
0.7059	Intermediate Similarity	NPC69029
0.7059	Intermediate Similarity	NPC313081
0.7059	Intermediate Similarity	NPC108198
0.7059	Intermediate Similarity	NPC158142
0.7059	Intermediate Similarity	NPC294884
0.7059	Intermediate Similarity	NPC241241
0.7059	Intermediate Similarity	NPC200557
0.7059	Intermediate Similarity	NPC473413
0.7059	Intermediate Similarity	NPC10314
0.7055	Intermediate Similarity	NPC136319
0.705	Intermediate Similarity	NPC166995
0.7047	Intermediate Similarity	NPC226331
0.7047	Intermediate Similarity	NPC46274
0.7039	Intermediate Similarity	NPC474453
0.7037	Intermediate Similarity	NPC474839
0.7037	Intermediate Similarity	NPC246056
0.7027	Intermediate Similarity	NPC28730
0.7027	Intermediate Similarity	NPC44748
0.7027	Intermediate Similarity	NPC223136
0.7027	Intermediate Similarity	NPC103823
0.7027	Intermediate Similarity	NPC214406
0.7027	Intermediate Similarity	NPC18924
0.7027	Intermediate Similarity	NPC78974
0.7021	Intermediate Similarity	NPC84999
0.7021	Intermediate Similarity	NPC246760
0.702	Intermediate Similarity	NPC259017
0.7013	Intermediate Similarity	NPC143139
0.7013	Intermediate Similarity	NPC470802
0.7013	Intermediate Similarity	NPC114155
0.7013	Intermediate Similarity	NPC476639
0.7013	Intermediate Similarity	NPC30632
0.7013	Intermediate Similarity	NPC202846
0.7013	Intermediate Similarity	NPC300846
0.7007	Intermediate Similarity	NPC139774
0.7006	Intermediate Similarity	NPC183709
0.7006	Intermediate Similarity	NPC175838
0.7	Intermediate Similarity	NPC206183
0.7	Intermediate Similarity	NPC222684
0.7	Intermediate Similarity	NPC212015
0.7	Intermediate Similarity	NPC76400
0.6995	Remote Similarity	NPC156055
0.6993	Remote Similarity	NPC160697
0.6993	Remote Similarity	NPC209199
0.6988	Remote Similarity	NPC38980
0.6986	Remote Similarity	NPC120172
0.6985	Remote Similarity	NPC39097
0.6985	Remote Similarity	NPC248904
0.6985	Remote Similarity	NPC302681
0.6985	Remote Similarity	NPC39664
0.6985	Remote Similarity	NPC470700
0.6985	Remote Similarity	NPC109691
0.6985	Remote Similarity	NPC118286
0.698	Remote Similarity	NPC266555
0.6978	Remote Similarity	NPC179002
0.6978	Remote Similarity	NPC187583
0.6978	Remote Similarity	NPC257430
0.6974	Remote Similarity	NPC131128
0.6974	Remote Similarity	NPC127624
0.6974	Remote Similarity	NPC474134
0.6974	Remote Similarity	NPC86655
0.6974	Remote Similarity	NPC14224
0.6974	Remote Similarity	NPC161958
0.6974	Remote Similarity	NPC202762
0.6972	Remote Similarity	NPC115808
0.6968	Remote Similarity	NPC272157
0.6968	Remote Similarity	NPC6262

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 NPC118794 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	588
0.1-0.2	1106
0.2-0.3	2739
0.3-0.4	2831
0.4-0.5	1339
0.5-0.6	498
0.6-0.7	49
0.7-0.8	0
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
0.7095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3022	Approved
0.6957	Remote Similarity	NPD3021	Approved
0.6866	Remote Similarity	NPD1242	Phase 1
0.6863	Remote Similarity	NPD1613	Approved
0.6863	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3027	Phase 3
0.6753	Remote Similarity	NPD943	Approved
0.6714	Remote Similarity	NPD4750	Phase 3
0.6691	Remote Similarity	NPD940	Approved
0.6691	Remote Similarity	NPD846	Approved
0.6667	Remote Similarity	NPD4288	Approved
0.6623	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD9244	Approved
0.6571	Remote Similarity	NPD2342	Discontinued
0.6494	Remote Similarity	NPD4908	Phase 1
0.6437	Remote Similarity	NPD4010	Discontinued
0.6375	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1610	Phase 2
0.6349	Remote Similarity	NPD8095	Phase 1
0.6346	Remote Similarity	NPD4625	Phase 3
0.6324	Remote Similarity	NPD2859	Approved
0.6324	Remote Similarity	NPD2860	Approved
0.6316	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD1548	Phase 1
0.6304	Remote Similarity	NPD3020	Approved
0.627	Remote Similarity	NPD4287	Approved
0.6265	Remote Similarity	NPD1511	Approved
0.6265	Remote Similarity	NPD7390	Discontinued
0.625	Remote Similarity	NPD2934	Approved
0.625	Remote Similarity	NPD2933	Approved
0.6243	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD2286	Discontinued
0.6218	Remote Similarity	NPD3018	Phase 2
0.6209	Remote Similarity	NPD9269	Phase 2
0.6207	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD3094	Phase 2
0.619	Remote Similarity	NPD1512	Approved
0.6173	Remote Similarity	NPD1169	Approved
0.6173	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD4749	Approved
0.6164	Remote Similarity	NPD228	Approved
0.6163	Remote Similarity	NPD1934	Approved
0.6144	Remote Similarity	NPD3092	Approved
0.6135	Remote Similarity	NPD5406	Approved
0.6135	Remote Similarity	NPD5408	Approved
0.6135	Remote Similarity	NPD5405	Approved
0.6135	Remote Similarity	NPD5404	Approved
0.6122	Remote Similarity	NPD7635	Approved
0.6122	Remote Similarity	NPD9379	Approved
0.6122	Remote Similarity	NPD9377	Approved
0.6098	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.609	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD1809	Phase 2
0.6087	Remote Similarity	NPD844	Approved
0.608	Remote Similarity	NPD6234	Discontinued
0.6067	Remote Similarity	NPD6232	Discontinued
0.6065	Remote Similarity	NPD2982	Phase 2
0.6065	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD2983	Phase 2
0.6045	Remote Similarity	NPD9094	Approved
0.6043	Remote Similarity	NPD288	Approved
0.6039	Remote Similarity	NPD1201	Approved
0.6038	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD2801	Approved
0.6028	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD5311	Approved
0.6026	Remote Similarity	NPD5310	Approved
0.6025	Remote Similarity	NPD3059	Approved
0.6025	Remote Similarity	NPD3062	Approved
0.6025	Remote Similarity	NPD3620	Phase 2
0.6025	Remote Similarity	NPD3061	Approved
0.6025	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD9381	Approved
0.6013	Remote Similarity	NPD9384	Approved
0.6	Remote Similarity	NPD6166	Phase 2
0.6	Remote Similarity	NPD2981	Phase 2
0.6	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7266	Discontinued
0.6	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD230	Phase 1
0.5987	Remote Similarity	NPD3091	Approved
0.5987	Remote Similarity	NPD1470	Approved
0.5987	Remote Similarity	NPD3055	Approved
0.5987	Remote Similarity	NPD3053	Approved
0.5977	Remote Similarity	NPD37	Approved
0.5976	Remote Similarity	NPD2420	Approved
0.5976	Remote Similarity	NPD2421	Approved
0.5973	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD5283	Phase 1
0.5967	Remote Similarity	NPD7473	Discontinued
0.5963	Remote Similarity	NPD6407	Approved
0.5963	Remote Similarity	NPD6405	Approved
0.5962	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6190	Approved
0.5951	Remote Similarity	NPD5314	Approved
0.5949	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD4093	Discontinued
0.5948	Remote Similarity	NPD9268	Approved
0.5942	Remote Similarity	NPD845	Approved
0.5941	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4060	Phase 1
0.5926	Remote Similarity	NPD1555	Discontinued
0.5917	Remote Similarity	NPD3845	Phase 1
0.5912	Remote Similarity	NPD2861	Phase 2
0.5909	Remote Similarity	NPD4059	Approved
0.5909	Remote Similarity	NPD3019	Approved
0.5909	Remote Similarity	NPD2296	Approved
0.5906	Remote Similarity	NPD2184	Approved
0.5906	Remote Similarity	NPD2183	Approved
0.5901	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD1510	Phase 2
0.5876	Remote Similarity	NPD3882	Suspended
0.5876	Remote Similarity	NPD4965	Approved
0.5876	Remote Similarity	NPD4966	Approved
0.5876	Remote Similarity	NPD4967	Phase 2
0.5862	Remote Similarity	NPD4380	Phase 2
0.586	Remote Similarity	NPD9622	Approved
0.5858	Remote Similarity	NPD302	Approved
0.5854	Remote Similarity	NPD2568	Approved
0.5852	Remote Similarity	NPD1465	Phase 2
0.5848	Remote Similarity	NPD7447	Phase 1
0.5848	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD7228	Approved
0.5839	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD9718	Approved
0.5838	Remote Similarity	NPD1653	Approved
0.5838	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD422	Phase 1
0.5833	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7199	Phase 2
0.5828	Remote Similarity	NPD1558	Phase 1
0.5815	Remote Similarity	NPD5844	Phase 1
0.5808	Remote Similarity	NPD3540	Phase 1
0.5806	Remote Similarity	NPD3095	Discontinued
0.5806	Remote Similarity	NPD4589	Approved
0.5806	Remote Similarity	NPD2932	Approved
0.5799	Remote Similarity	NPD3750	Approved
0.5799	Remote Similarity	NPD8166	Discontinued
0.5789	Remote Similarity	NPD7213	Phase 3
0.5789	Remote Similarity	NPD7212	Phase 2
0.5786	Remote Similarity	NPD1164	Approved
0.5779	Remote Similarity	NPD5303	Approved
0.5779	Remote Similarity	NPD5304	Approved
0.5769	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6687	Approved
0.5769	Remote Similarity	NPD6688	Approved
0.5762	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD3818	Discontinued
0.5758	Remote Similarity	NPD4097	Suspended
0.575	Remote Similarity	NPD257	Approved
0.575	Remote Similarity	NPD258	Approved
0.575	Remote Similarity	NPD9621	Approved
0.575	Remote Similarity	NPD6584	Phase 3
0.575	Remote Similarity	NPD9620	Approved
0.575	Remote Similarity	NPD9619	Approved
0.5749	Remote Similarity	NPD6099	Approved
0.5749	Remote Similarity	NPD2935	Discontinued
0.5749	Remote Similarity	NPD6100	Approved
0.5749	Remote Similarity	NPD3539	Phase 1
0.574	Remote Similarity	NPD6674	Discontinued
0.5732	Remote Similarity	NPD1240	Approved
0.5731	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.573	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD497	Approved
0.5724	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8053	Approved
0.5714	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4005	Discontinued
0.5714	Remote Similarity	NPD8054	Approved
0.5714	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD3764	Approved
0.5706	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.5705	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD111	Approved
0.5699	Remote Similarity	NPD7074	Phase 3
0.5698	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD7041	Phase 2
0.5698	Remote Similarity	NPD7768	Phase 2
0.5698	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD3028	Approved
0.569	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.5689	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6671	Approved
0.568	Remote Similarity	NPD1549	Phase 2
0.5667	Remote Similarity	NPD7075	Discontinued
0.5663	Remote Similarity	NPD817	Approved
0.5663	Remote Similarity	NPD1607	Approved
0.5663	Remote Similarity	NPD823	Approved
0.5659	Remote Similarity	NPD6959	Discontinued
0.5658	Remote Similarity	NPD498	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