NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.13
Volume:	284.601
LogP:	3.978
LogD:	3.897
LogS:	-3.841
# Rotatable Bonds:	3
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.797
Synthetic Accessibility Score:	2.155
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.879
MDCK Permeability:	1.5848472685320303e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.531
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204
Plasma Protein Binding (PPB):	99.3848648071289%
Volume Distribution (VD):	0.933
Pgp-substrate:	0.7131226062774658%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.473
CYP2C19-inhibitor:	0.693
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.71
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.671
CYP2D6-substrate:	0.42
CYP3A4-inhibitor:	0.582
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	4.845
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.731
AMES Toxicity:	0.226
Rat Oral Acute Toxicity:	0.105
Maximum Recommended Daily Dose:	0.124
Skin Sensitization:	0.871
Carcinogencity:	0.203
Eye Corrosion:	0.007
Eye Irritation:	0.954
Respiratory Toxicity:	0.762

Download Data

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

Natural Product: NPC224527

Natural Product ID:	NPC224527
*Common Name:**	3,5-Dihydroxy-4-Isopropylstilbene
IUPAC Name:	5-[(E)-2-phenylethenyl]-2-propan-2-ylbenzene-1,3-diol
Synonyms:
Standard InCHIKey:	ZISJNXNHJRQYJO-CMDGGOBGSA-N
Standard InCHI:	InChI=1S/C17H18O2/c1-12(2)17-15(18)10-14(11-16(17)19)9-8-13-6-4-3-5-7-13/h3-12,18-19H,1-2H3/b9-8+
SMILES:	CC(c1c(O)cc(cc1O)/C=C/c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL259571
PubChem CID:	6439522
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22909174]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25988621]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	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	7

Activity Type	# Activity
Organism	5
SINGLE PROTEIN	1
TISSUE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT26019	TISSUE	Hemolymph	Manduca sexta	Drug uptake	=	275.0	ug ml-1	PMID[490064]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	LC50	=	50.0	ug.mL-1	PMID[490065]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	4.0	mm	PMID[490066]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	17.67	%	PMID[490067]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.06	%	PMID[490068]

☑ 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 NPC224527 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	311
0.1-0.2	1765
0.2-0.3	4606
0.3-0.4	13745
0.4-0.5	5337
0.5-0.6	7681
0.6-0.7	6886
0.7-0.8	1951
0.8-0.85	262
0.85-0.9	93
0.9-0.95	49
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC19808
0.9806	High Similarity	NPC33728
0.9709	High Similarity	NPC174981
0.9626	High Similarity	NPC246760
0.9626	High Similarity	NPC84999
0.9623	High Similarity	NPC23804
0.9615	High Similarity	NPC299568
0.9615	High Similarity	NPC186385
0.9528	High Similarity	NPC166995
0.9439	High Similarity	NPC117846
0.9423	High Similarity	NPC158253
0.9423	High Similarity	NPC204901
0.9423	High Similarity	NPC232523
0.9417	High Similarity	NPC37802
0.9327	High Similarity	NPC12640
0.9327	High Similarity	NPC201662
0.9327	High Similarity	NPC99836
0.932	High Similarity	NPC241891
0.932	High Similarity	NPC244513
0.932	High Similarity	NPC102216
0.932	High Similarity	NPC227458
0.932	High Similarity	NPC218879
0.9259	High Similarity	NPC319803
0.9259	High Similarity	NPC261343
0.9252	High Similarity	NPC165770
0.9252	High Similarity	NPC225679
0.9252	High Similarity	NPC4493
0.9252	High Similarity	NPC476632
0.9231	High Similarity	NPC134829
0.9189	High Similarity	NPC9592
0.9189	High Similarity	NPC48781
0.9174	High Similarity	NPC107240
0.9167	High Similarity	NPC43525
0.9143	High Similarity	NPC109691
0.9143	High Similarity	NPC248904
0.9143	High Similarity	NPC39664
0.9143	High Similarity	NPC302681
0.9143	High Similarity	NPC39097
0.9143	High Similarity	NPC118286
0.9143	High Similarity	NPC470700
0.9126	High Similarity	NPC100340
0.9126	High Similarity	NPC143659
0.9099	High Similarity	NPC470760
0.9057	High Similarity	NPC54844
0.9048	High Similarity	NPC246056
0.9048	High Similarity	NPC474839
0.9038	High Similarity	NPC94351
0.9038	High Similarity	NPC302219
0.9038	High Similarity	NPC242342
0.9038	High Similarity	NPC168303
0.9038	High Similarity	NPC249828
0.9038	High Similarity	NPC53051
0.9038	High Similarity	NPC24404
0.9038	High Similarity	NPC313030
0.9038	High Similarity	NPC146798
0.9038	High Similarity	NPC85479
0.9038	High Similarity	NPC106396
0.9038	High Similarity	NPC222522
0.9038	High Similarity	NPC71002
0.9029	High Similarity	NPC166761
0.9029	High Similarity	NPC10588
0.9027	High Similarity	NPC69006
0.9018	High Similarity	NPC190514
0.9018	High Similarity	NPC144343
0.9018	High Similarity	NPC206
0.9009	High Similarity	NPC115808
0.8972	High Similarity	NPC63698
0.8972	High Similarity	NPC61885
0.8952	High Similarity	NPC30506
0.8952	High Similarity	NPC119860
0.8942	High Similarity	NPC147310
0.8942	High Similarity	NPC294186
0.8942	High Similarity	NPC24407
0.8942	High Similarity	NPC192032
0.8942	High Similarity	NPC284011
0.8942	High Similarity	NPC137415
0.8942	High Similarity	NPC11280
0.8942	High Similarity	NPC72947
0.8942	High Similarity	NPC166313
0.8938	High Similarity	NPC184302
0.8909	High Similarity	NPC263753
0.8889	High Similarity	NPC202647
0.8868	High Similarity	NPC292452
0.8846	High Similarity	NPC72729
0.8835	High Similarity	NPC79241
0.8835	High Similarity	NPC6597
0.8835	High Similarity	NPC291789
0.8829	High Similarity	NPC249270
0.8807	High Similarity	NPC224870
0.8793	High Similarity	NPC122175
0.8783	High Similarity	NPC24125
0.8772	High Similarity	NPC191866
0.8761	High Similarity	NPC33270
0.8761	High Similarity	NPC69261
0.875	High Similarity	NPC808
0.8738	High Similarity	NPC312132
0.8738	High Similarity	NPC259512
0.8727	High Similarity	NPC151537
0.8707	High Similarity	NPC39029
0.8704	High Similarity	NPC66834
0.8704	High Similarity	NPC305603
0.8704	High Similarity	NPC61033
0.8692	High Similarity	NPC117115
0.8679	High Similarity	NPC168393
0.8673	High Similarity	NPC150624
0.8667	High Similarity	NPC248573
0.8667	High Similarity	NPC275053
0.8667	High Similarity	NPC161571
0.8649	High Similarity	NPC473521
0.8644	High Similarity	NPC139774
0.8644	High Similarity	NPC174729
0.8636	High Similarity	NPC475018
0.8632	High Similarity	NPC18128
0.8632	High Similarity	NPC77789
0.8609	High Similarity	NPC217174
0.8598	High Similarity	NPC475225
0.8596	High Similarity	NPC50521
0.8596	High Similarity	NPC221549
0.8596	High Similarity	NPC277588
0.8596	High Similarity	NPC244816
0.8585	High Similarity	NPC12221
0.8585	High Similarity	NPC252105
0.8584	High Similarity	NPC53906
0.8584	High Similarity	NPC232165
0.8571	High Similarity	NPC299762
0.8571	High Similarity	NPC33675
0.8571	High Similarity	NPC105031
0.8571	High Similarity	NPC80027
0.8559	High Similarity	NPC54373
0.8547	High Similarity	NPC237667
0.8545	High Similarity	NPC58865
0.8544	High Similarity	NPC76938
0.8534	High Similarity	NPC223451
0.8532	High Similarity	NPC151477
0.8532	High Similarity	NPC320439
0.8519	High Similarity	NPC47284
0.8505	High Similarity	NPC471228
0.8505	High Similarity	NPC235762
0.85	High Similarity	NPC111723
0.85	High Similarity	NPC237517
0.85	High Similarity	NPC91204
0.8496	Intermediate Similarity	NPC276737
0.8496	Intermediate Similarity	NPC22610
0.8487	Intermediate Similarity	NPC224342
0.8482	Intermediate Similarity	NPC228452
0.8482	Intermediate Similarity	NPC46940
0.8475	Intermediate Similarity	NPC120172
0.8468	Intermediate Similarity	NPC132720
0.8462	Intermediate Similarity	NPC218753
0.8462	Intermediate Similarity	NPC102639
0.8462	Intermediate Similarity	NPC32714
0.8455	Intermediate Similarity	NPC306295
0.8455	Intermediate Similarity	NPC11554
0.8448	Intermediate Similarity	NPC151197
0.8448	Intermediate Similarity	NPC121866
0.8447	Intermediate Similarity	NPC295295
0.8443	Intermediate Similarity	NPC222108
0.8443	Intermediate Similarity	NPC96719
0.844	Intermediate Similarity	NPC67250
0.844	Intermediate Similarity	NPC53740
0.8435	Intermediate Similarity	NPC219070
0.8435	Intermediate Similarity	NPC127894
0.8435	Intermediate Similarity	NPC470759
0.8435	Intermediate Similarity	NPC15860
0.8435	Intermediate Similarity	NPC474933
0.843	Intermediate Similarity	NPC473221
0.843	Intermediate Similarity	NPC32715
0.843	Intermediate Similarity	NPC46978
0.843	Intermediate Similarity	NPC66331
0.843	Intermediate Similarity	NPC257947
0.843	Intermediate Similarity	NPC98200
0.8426	Intermediate Similarity	NPC323810
0.8426	Intermediate Similarity	NPC238696
0.8421	Intermediate Similarity	NPC167934
0.8411	Intermediate Similarity	NPC477685
0.8407	Intermediate Similarity	NPC715
0.8403	Intermediate Similarity	NPC96940
0.8403	Intermediate Similarity	NPC53567
0.8393	Intermediate Similarity	NPC268032
0.8393	Intermediate Similarity	NPC95716
0.8393	Intermediate Similarity	NPC266937
0.8393	Intermediate Similarity	NPC469912
0.8393	Intermediate Similarity	NPC77772
0.8393	Intermediate Similarity	NPC470770
0.839	Intermediate Similarity	NPC476633
0.8381	Intermediate Similarity	NPC292730
0.8381	Intermediate Similarity	NPC473388
0.8381	Intermediate Similarity	NPC132271
0.8381	Intermediate Similarity	NPC82664
0.8381	Intermediate Similarity	NPC216520
0.835	Intermediate Similarity	NPC231150
0.8349	Intermediate Similarity	NPC138942
0.8349	Intermediate Similarity	NPC471350
0.8348	Intermediate Similarity	NPC85292
0.8348	Intermediate Similarity	NPC114064
0.8348	Intermediate Similarity	NPC141090
0.8348	Intermediate Similarity	NPC54507
0.8348	Intermediate Similarity	NPC229147
0.8348	Intermediate Similarity	NPC141001
0.8347	Intermediate Similarity	NPC82299

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 NPC224527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	1027
0.2-0.3	1271
0.3-0.4	3015
0.4-0.5	1833
0.5-0.6	1158
0.6-0.7	442
0.7-0.8	58
0.8-0.85	14
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9615	High Similarity	NPD4750	Phase 3
0.8762	High Similarity	NPD940	Approved
0.8762	High Similarity	NPD846	Approved
0.8738	High Similarity	NPD288	Approved
0.8667	High Similarity	NPD1242	Phase 1
0.8641	High Similarity	NPD844	Approved
0.8571	High Similarity	NPD3020	Approved
0.8482	Intermediate Similarity	NPD7635	Approved
0.8403	Intermediate Similarity	NPD4749	Approved
0.8293	Intermediate Similarity	NPD4625	Phase 3
0.8286	Intermediate Similarity	NPD2860	Approved
0.8286	Intermediate Similarity	NPD2859	Approved
0.8214	Intermediate Similarity	NPD3022	Approved
0.8214	Intermediate Similarity	NPD3021	Approved
0.8198	Intermediate Similarity	NPD2342	Discontinued
0.819	Intermediate Similarity	NPD2934	Approved
0.819	Intermediate Similarity	NPD2933	Approved
0.8148	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD845	Approved
0.8049	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD1610	Phase 2
0.792	Intermediate Similarity	NPD4908	Phase 1
0.785	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD1792	Phase 2
0.7652	Intermediate Similarity	NPD6100	Approved
0.7652	Intermediate Similarity	NPD6099	Approved
0.7632	Intermediate Similarity	NPD1445	Approved
0.7632	Intermediate Similarity	NPD1444	Approved
0.7615	Intermediate Similarity	NPD1809	Phase 2
0.7603	Intermediate Similarity	NPD1548	Phase 1
0.7603	Intermediate Similarity	NPD3091	Approved
0.7583	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3027	Phase 3
0.7563	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD3092	Approved
0.75	Intermediate Similarity	NPD6671	Approved
0.748	Intermediate Similarity	NPD2932	Approved
0.748	Intermediate Similarity	NPD3019	Approved
0.748	Intermediate Similarity	NPD4059	Approved
0.7479	Intermediate Similarity	NPD2229	Approved
0.7479	Intermediate Similarity	NPD2228	Approved
0.7479	Intermediate Similarity	NPD2234	Approved
0.7444	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD2861	Phase 2
0.7422	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD497	Approved
0.7402	Intermediate Similarity	NPD3094	Phase 2
0.7398	Intermediate Similarity	NPD4093	Discontinued
0.7379	Intermediate Similarity	NPD9089	Approved
0.7339	Intermediate Similarity	NPD2286	Discontinued
0.7333	Intermediate Similarity	NPD495	Approved
0.7333	Intermediate Similarity	NPD496	Approved
0.7333	Intermediate Similarity	NPD498	Approved
0.7333	Intermediate Similarity	NPD111	Approved
0.7317	Intermediate Similarity	NPD5304	Approved
0.7317	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5303	Approved
0.7299	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD9093	Approved
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD1613	Approved
0.7266	Intermediate Similarity	NPD7390	Discontinued
0.7266	Intermediate Similarity	NPD1470	Approved
0.7266	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD422	Phase 1
0.7217	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3095	Discontinued
0.72	Intermediate Similarity	NPD4626	Approved
0.72	Intermediate Similarity	NPD4589	Approved
0.72	Intermediate Similarity	NPD1751	Approved
0.72	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3028	Approved
0.719	Intermediate Similarity	NPD5283	Phase 1
0.7188	Intermediate Similarity	NPD6696	Suspended
0.7168	Intermediate Similarity	NPD9273	Approved
0.7165	Intermediate Similarity	NPD2233	Approved
0.7165	Intermediate Similarity	NPD2232	Approved
0.7165	Intermediate Similarity	NPD2230	Approved
0.7164	Intermediate Similarity	NPD4097	Suspended
0.7164	Intermediate Similarity	NPD1607	Approved
0.7164	Intermediate Similarity	NPD2568	Approved
0.7154	Intermediate Similarity	NPD3018	Phase 2
0.7143	Intermediate Similarity	NPD1983	Approved
0.7143	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD1980	Approved
0.7143	Intermediate Similarity	NPD1981	Approved
0.7132	Intermediate Similarity	NPD5408	Approved
0.7132	Intermediate Similarity	NPD2797	Approved
0.7132	Intermediate Similarity	NPD5406	Approved
0.7132	Intermediate Similarity	NPD5404	Approved
0.7132	Intermediate Similarity	NPD5405	Approved
0.7073	Intermediate Similarity	NPD709	Approved
0.705	Intermediate Similarity	NPD3892	Phase 2
0.704	Intermediate Similarity	NPD7330	Discontinued
0.7031	Intermediate Similarity	NPD1608	Approved
0.7025	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5736	Approved
0.7016	Intermediate Similarity	NPD7340	Approved
0.7015	Intermediate Similarity	NPD1240	Approved
0.7015	Intermediate Similarity	NPD4060	Phase 1
0.6992	Remote Similarity	NPD1793	Approved
0.6992	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1791	Approved
0.6977	Remote Similarity	NPD2983	Phase 2
0.6977	Remote Similarity	NPD2982	Phase 2
0.6977	Remote Similarity	NPD4659	Approved
0.6972	Remote Similarity	NPD9094	Approved
0.6947	Remote Similarity	NPD2194	Approved
0.6947	Remote Similarity	NPD2195	Approved
0.6947	Remote Similarity	NPD599	Approved
0.6947	Remote Similarity	NPD858	Approved
0.6947	Remote Similarity	NPD602	Approved
0.6947	Remote Similarity	NPD859	Approved
0.694	Remote Similarity	NPD6405	Approved
0.694	Remote Similarity	NPD6407	Approved
0.6934	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1283	Approved
0.6923	Remote Similarity	NPD9500	Approved
0.6917	Remote Similarity	NPD5155	Approved
0.6917	Remote Similarity	NPD5156	Approved
0.6911	Remote Similarity	NPD1398	Phase 1
0.6911	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2981	Phase 2
0.6897	Remote Similarity	NPD1616	Discontinued
0.6894	Remote Similarity	NPD3637	Approved
0.6894	Remote Similarity	NPD3635	Approved
0.6894	Remote Similarity	NPD3636	Approved
0.6891	Remote Similarity	NPD968	Approved
0.6889	Remote Similarity	NPD1555	Discontinued
0.6885	Remote Similarity	NPD228	Approved
0.688	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3026	Approved
0.6875	Remote Similarity	NPD3023	Approved
0.687	Remote Similarity	NPD4103	Phase 2
0.687	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1164	Approved
0.6866	Remote Similarity	NPD3268	Approved
0.6857	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5691	Approved
0.685	Remote Similarity	NPD1651	Approved
0.685	Remote Similarity	NPD3024	Approved
0.685	Remote Similarity	NPD3025	Approved
0.6842	Remote Similarity	NPD2606	Approved
0.6842	Remote Similarity	NPD2605	Approved
0.6822	Remote Similarity	NPD1611	Approved
0.6818	Remote Similarity	NPD6584	Phase 3
0.6818	Remote Similarity	NPD4624	Approved
0.6815	Remote Similarity	NPD6663	Approved
0.6812	Remote Similarity	NPD1510	Phase 2
0.6809	Remote Similarity	NPD3750	Approved
0.68	Remote Similarity	NPD6387	Discontinued
0.6797	Remote Similarity	NPD1778	Approved
0.6797	Remote Similarity	NPD17	Approved
0.6797	Remote Similarity	NPD2668	Approved
0.6797	Remote Similarity	NPD2667	Approved
0.6786	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD2562	Approved
0.6769	Remote Similarity	NPD2561	Approved
0.6765	Remote Similarity	NPD6346	Approved
0.6763	Remote Similarity	NPD1551	Phase 2
0.6763	Remote Similarity	NPD2935	Discontinued
0.6742	Remote Similarity	NPD3055	Approved
0.6742	Remote Similarity	NPD1131	Approved
0.6742	Remote Similarity	NPD1133	Approved
0.6742	Remote Similarity	NPD3053	Approved
0.6742	Remote Similarity	NPD1134	Approved
0.6742	Remote Similarity	NPD1129	Approved
0.6742	Remote Similarity	NPD1135	Approved
0.6741	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3553	Approved
0.6739	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3554	Approved
0.6739	Remote Similarity	NPD3555	Approved
0.6739	Remote Similarity	NPD3552	Approved
0.6736	Remote Similarity	NPD7447	Phase 1
0.6736	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD9608	Approved
0.6723	Remote Similarity	NPD9610	Approved
0.6721	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5451	Approved
0.672	Remote Similarity	NPD9614	Approved
0.672	Remote Similarity	NPD9618	Approved
0.6718	Remote Similarity	NPD1755	Approved
0.6716	Remote Similarity	NPD3595	Approved
0.6716	Remote Similarity	NPD3594	Approved
0.6714	Remote Similarity	NPD4725	Approved
0.6714	Remote Similarity	NPD4721	Approved
0.6714	Remote Similarity	NPD5763	Approved
0.6714	Remote Similarity	NPD4726	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