NPASS Compound

Structure

NPC87113 OpenBabel07101719152D 21 22 0 0 0 0 0 0 0 0999 V2000 -3.4641 0.0000 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 5.1962 -1.0000 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 4.3301 -1.5000 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 3.4641 -0.0000 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 1.7321 -1.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 -1.0000 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 1.7321 -0.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 1 2 2 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 14 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	280.11
Volume:	305.414
LogP:	3.889
LogD:	3.511
LogS:	-4.401
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.492
Synthetic Accessibility Score:	2.393
Fsp3:	0.056
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.738
MDCK Permeability:	1.5097200957825407e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.894
30% Bioavailability (F30%):	0.722

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	99.5390853881836%
Volume Distribution (VD):	0.455
Pgp-substrate:	0.549679696559906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.946
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.789
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.781
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.691
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	5.209
Half-life (T1/2):	0.564

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.148
AMES Toxicity:	0.616
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.952
Carcinogencity:	0.86
Eye Corrosion:	0.005
Eye Irritation:	0.961
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC87113

Natural Product ID:	NPC87113
*Common Name:**	Isostrebluslignanaldehyde
IUPAC Name:	(E)-3-[4-(2-hydroxy-4-prop-2-enylphenoxy)phenyl]prop-2-enal
Synonyms:	isostrebluslignanaldehyde
Standard InCHIKey:	OEMPNLUEIYKHQQ-HWKANZROSA-N
Standard InCHI:	InChI=1S/C18H16O3/c1-2-4-15-8-11-18(17(20)13-15)21-16-9-6-14(7-10-16)5-3-12-19/h2-3,5-13,20H,1,4H2/b5-3+
SMILES:	C=CCc1ccc(c(c1)O)Oc1ccc(/C=C/C=O)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346746
PubChem CID:	71580866
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[23434030]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4093781]
NPO28043	Streblus asper	Species	Moraceae	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
Others	4

Activity Type	# Activity
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio CC50/IC50	=	3.27	n.a.	PMID[503801]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	61220.0	nM	PMID[503801]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	19.11	n.a.	PMID[503801]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	10490.0	nM	PMID[503801]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	16.46	n.a.	PMID[503801]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	12180.0	nM	PMID[503801]
NPT27	Others	Unspecified		CC50	=	200430.0	nM	PMID[503801]

☑ 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 NPC87113 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	312
0.1-0.2	1824
0.2-0.3	5254
0.3-0.4	13469
0.4-0.5	3938
0.5-0.6	4621
0.6-0.7	9057
0.7-0.8	3596
0.8-0.85	458
0.85-0.9	153
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9291	High Similarity	NPC237594
0.9291	High Similarity	NPC249791
0.9291	High Similarity	NPC119060
0.9291	High Similarity	NPC476387
0.9268	High Similarity	NPC213552
0.9268	High Similarity	NPC120225
0.9237	High Similarity	NPC86947
0.9219	High Similarity	NPC214729
0.9213	High Similarity	NPC36490
0.9187	High Similarity	NPC289459
0.9174	High Similarity	NPC290451
0.9174	High Similarity	NPC127389
0.9106	High Similarity	NPC246704
0.9091	High Similarity	NPC189844
0.9091	High Similarity	NPC109083
0.9091	High Similarity	NPC60962
0.9091	High Similarity	NPC224814
0.9091	High Similarity	NPC14007
0.9091	High Similarity	NPC269843
0.9076	High Similarity	NPC39793
0.9048	High Similarity	NPC83062
0.8992	High Similarity	NPC144662
0.896	High Similarity	NPC179777
0.8952	High Similarity	NPC20443
0.8952	High Similarity	NPC60517
0.8952	High Similarity	NPC146886
0.8939	High Similarity	NPC267291
0.8898	High Similarity	NPC241354
0.8889	High Similarity	NPC123228
0.8889	High Similarity	NPC151167
0.8889	High Similarity	NPC123722
0.8889	High Similarity	NPC5018
0.8889	High Similarity	NPC276466
0.888	High Similarity	NPC194519
0.888	High Similarity	NPC3221
0.8872	High Similarity	NPC224876
0.8872	High Similarity	NPC83375
0.8871	High Similarity	NPC229084
0.8871	High Similarity	NPC18984
0.8871	High Similarity	NPC160900
0.8871	High Similarity	NPC106659
0.8855	High Similarity	NPC471664
0.8855	High Similarity	NPC471665
0.8843	High Similarity	NPC470626
0.8843	High Similarity	NPC212743
0.8819	High Similarity	NPC110313
0.8819	High Similarity	NPC226661
0.881	High Similarity	NPC303680
0.881	High Similarity	NPC178284
0.881	High Similarity	NPC191037
0.881	High Similarity	NPC90128
0.881	High Similarity	NPC58607
0.881	High Similarity	NPC84076
0.8806	High Similarity	NPC278469
0.8806	High Similarity	NPC193722
0.88	High Similarity	NPC114901
0.88	High Similarity	NPC293701
0.88	High Similarity	NPC48990
0.8788	High Similarity	NPC126206
0.878	High Similarity	NPC207613
0.878	High Similarity	NPC204466
0.877	High Similarity	NPC281298
0.877	High Similarity	NPC263386
0.877	High Similarity	NPC310338
0.877	High Similarity	NPC141791
0.876	High Similarity	NPC293619
0.876	High Similarity	NPC280001
0.875	High Similarity	NPC304622
0.874	High Similarity	NPC111247
0.874	High Similarity	NPC41706
0.874	High Similarity	NPC183181
0.874	High Similarity	NPC163332
0.874	High Similarity	NPC292056
0.874	High Similarity	NPC319625
0.874	High Similarity	NPC118787
0.874	High Similarity	NPC147821
0.872	High Similarity	NPC317769
0.872	High Similarity	NPC31344
0.872	High Similarity	NPC242372
0.872	High Similarity	NPC257976
0.872	High Similarity	NPC4181
0.872	High Similarity	NPC164778
0.871	High Similarity	NPC324571
0.871	High Similarity	NPC54872
0.871	High Similarity	NPC70752
0.871	High Similarity	NPC470212
0.871	High Similarity	NPC312675
0.871	High Similarity	NPC473853
0.871	High Similarity	NPC113865
0.871	High Similarity	NPC262156
0.871	High Similarity	NPC184651
0.871	High Similarity	NPC343720
0.8702	High Similarity	NPC135127
0.8699	High Similarity	NPC165133
0.8699	High Similarity	NPC232316
0.8699	High Similarity	NPC242885
0.8699	High Similarity	NPC56214
0.8699	High Similarity	NPC227217
0.8699	High Similarity	NPC95614
0.8699	High Similarity	NPC117780
0.8699	High Similarity	NPC202474
0.8689	High Similarity	NPC275519
0.8676	High Similarity	NPC474444
0.8676	High Similarity	NPC264706
0.8676	High Similarity	NPC93433
0.8676	High Similarity	NPC284881
0.8672	High Similarity	NPC478215
0.8672	High Similarity	NPC72529
0.8661	High Similarity	NPC17837
0.8661	High Similarity	NPC276014
0.8661	High Similarity	NPC304630
0.8651	High Similarity	NPC228972
0.8651	High Similarity	NPC312404
0.8651	High Similarity	NPC74478
0.8651	High Similarity	NPC122792
0.8651	High Similarity	NPC273686
0.8651	High Similarity	NPC109822
0.8651	High Similarity	NPC94276
0.864	High Similarity	NPC71090
0.864	High Similarity	NPC85488
0.864	High Similarity	NPC114298
0.864	High Similarity	NPC286573
0.8629	High Similarity	NPC470848
0.8629	High Similarity	NPC470849
0.8618	High Similarity	NPC37858
0.8607	High Similarity	NPC164386
0.8605	High Similarity	NPC86030
0.8605	High Similarity	NPC5851
0.8594	High Similarity	NPC210355
0.8583	High Similarity	NPC53305
0.8583	High Similarity	NPC257589
0.8571	High Similarity	NPC280704
0.8571	High Similarity	NPC90431
0.8571	High Similarity	NPC173746
0.8571	High Similarity	NPC120852
0.8571	High Similarity	NPC156840
0.8571	High Similarity	NPC8547
0.8571	High Similarity	NPC471693
0.8571	High Similarity	NPC257124
0.8561	High Similarity	NPC111635
0.856	High Similarity	NPC147654
0.856	High Similarity	NPC38996
0.856	High Similarity	NPC160380
0.8551	High Similarity	NPC287495
0.8551	High Similarity	NPC9370
0.8548	High Similarity	NPC2058
0.8538	High Similarity	NPC472338
0.8538	High Similarity	NPC298268
0.8537	High Similarity	NPC70744
0.8537	High Similarity	NPC272471
0.8537	High Similarity	NPC107588
0.8537	High Similarity	NPC277460
0.8537	High Similarity	NPC137537
0.8537	High Similarity	NPC164706
0.8516	High Similarity	NPC127937
0.8516	High Similarity	NPC92207
0.8516	High Similarity	NPC134431
0.8516	High Similarity	NPC156854
0.85	High Similarity	NPC165646
0.8496	Intermediate Similarity	NPC204592
0.8487	Intermediate Similarity	NPC179309
0.848	Intermediate Similarity	NPC307253
0.848	Intermediate Similarity	NPC158949
0.8473	Intermediate Similarity	NPC472597
0.8468	Intermediate Similarity	NPC24474
0.8468	Intermediate Similarity	NPC311595
0.8456	Intermediate Similarity	NPC82336
0.8456	Intermediate Similarity	NPC78987
0.845	Intermediate Similarity	NPC470699
0.8444	Intermediate Similarity	NPC284409
0.8438	Intermediate Similarity	NPC280767
0.8438	Intermediate Similarity	NPC271985
0.8438	Intermediate Similarity	NPC148627
0.8429	Intermediate Similarity	NPC473408
0.8429	Intermediate Similarity	NPC236166
0.8421	Intermediate Similarity	NPC473054
0.8417	Intermediate Similarity	NPC78918
0.8417	Intermediate Similarity	NPC55300
0.8417	Intermediate Similarity	NPC139617
0.8417	Intermediate Similarity	NPC297657
0.8413	Intermediate Similarity	NPC201777
0.8409	Intermediate Similarity	NPC470752
0.8409	Intermediate Similarity	NPC16208
0.8409	Intermediate Similarity	NPC245120
0.8409	Intermediate Similarity	NPC2190
0.8409	Intermediate Similarity	NPC7903
0.8409	Intermediate Similarity	NPC35932
0.8409	Intermediate Similarity	NPC160991
0.8409	Intermediate Similarity	NPC184447
0.8406	Intermediate Similarity	NPC160378
0.8403	Intermediate Similarity	NPC36108
0.8403	Intermediate Similarity	NPC233731
0.8403	Intermediate Similarity	NPC7097
0.8403	Intermediate Similarity	NPC246358
0.8397	Intermediate Similarity	NPC172673
0.8397	Intermediate Similarity	NPC244246
0.8397	Intermediate Similarity	NPC65935
0.8397	Intermediate Similarity	NPC137427
0.8397	Intermediate Similarity	NPC66905
0.8397	Intermediate Similarity	NPC91291

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 NPC87113 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	1024
0.2-0.3	1567
0.3-0.4	2780
0.4-0.5	1677
0.5-0.6	971
0.6-0.7	689
0.7-0.8	114
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8871	High Similarity	NPD4379	Clinical (unspecified phase)
0.8571	High Similarity	NPD228	Approved
0.8308	Intermediate Similarity	NPD9494	Approved
0.8306	Intermediate Similarity	NPD5536	Phase 2
0.8182	Intermediate Similarity	NPD3027	Phase 3
0.813	Intermediate Similarity	NPD5283	Phase 1
0.8017	Intermediate Similarity	NPD2684	Approved
0.8	Intermediate Similarity	NPD4060	Phase 1
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1613	Approved
0.797	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1558	Phase 1
0.7851	Intermediate Similarity	NPD968	Approved
0.7805	Intermediate Similarity	NPD3022	Approved
0.7805	Intermediate Similarity	NPD3021	Approved
0.776	Intermediate Similarity	NPD7843	Approved
0.7737	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD3620	Phase 2
0.7733	Intermediate Similarity	NPD3882	Suspended
0.7717	Intermediate Similarity	NPD7157	Approved
0.7704	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5846	Approved
0.7692	Intermediate Similarity	NPD6516	Phase 2
0.7687	Intermediate Similarity	NPD6584	Phase 3
0.766	Intermediate Similarity	NPD7266	Discontinued
0.7651	Intermediate Similarity	NPD1934	Approved
0.7647	Intermediate Similarity	NPD7095	Approved
0.7642	Intermediate Similarity	NPD1358	Approved
0.7634	Intermediate Similarity	NPD3496	Discontinued
0.763	Intermediate Similarity	NPD2861	Phase 2
0.7619	Intermediate Similarity	NPD1653	Approved
0.7615	Intermediate Similarity	NPD1357	Approved
0.76	Intermediate Similarity	NPD2801	Approved
0.7578	Intermediate Similarity	NPD6671	Approved
0.7561	Intermediate Similarity	NPD3134	Approved
0.7559	Intermediate Similarity	NPD1241	Discontinued
0.7554	Intermediate Similarity	NPD4340	Discontinued
0.7538	Intermediate Similarity	NPD1548	Phase 1
0.7538	Intermediate Similarity	NPD1894	Discontinued
0.7536	Intermediate Similarity	NPD2674	Phase 3
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD290	Approved
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5535	Approved
0.7466	Intermediate Similarity	NPD1511	Approved
0.7466	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD6798	Discontinued
0.7463	Intermediate Similarity	NPD6582	Phase 2
0.7463	Intermediate Similarity	NPD6583	Phase 3
0.7444	Intermediate Similarity	NPD1610	Phase 2
0.7431	Intermediate Similarity	NPD4162	Approved
0.7429	Intermediate Similarity	NPD6355	Discontinued
0.7424	Intermediate Similarity	NPD4626	Approved
0.741	Intermediate Similarity	NPD6233	Phase 2
0.741	Intermediate Similarity	NPD4062	Phase 3
0.7388	Intermediate Similarity	NPD2231	Phase 2
0.7388	Intermediate Similarity	NPD2235	Phase 2
0.7379	Intermediate Similarity	NPD6331	Phase 2
0.7365	Intermediate Similarity	NPD1512	Approved
0.7348	Intermediate Similarity	NPD5691	Approved
0.7348	Intermediate Similarity	NPD5585	Approved
0.7344	Intermediate Similarity	NPD821	Approved
0.7338	Intermediate Similarity	NPD3144	Approved
0.7338	Intermediate Similarity	NPD3145	Approved
0.7333	Intermediate Similarity	NPD2982	Phase 2
0.7333	Intermediate Similarity	NPD2983	Phase 2
0.7333	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6190	Approved
0.7319	Intermediate Similarity	NPD4908	Phase 1
0.7313	Intermediate Similarity	NPD1535	Discovery
0.7313	Intermediate Similarity	NPD422	Phase 1
0.7313	Intermediate Similarity	NPD3705	Approved
0.7311	Intermediate Similarity	NPD2933	Approved
0.7311	Intermediate Similarity	NPD2934	Approved
0.7311	Intermediate Similarity	NPD9296	Approved
0.731	Intermediate Similarity	NPD3060	Approved
0.7305	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD3818	Discontinued
0.7286	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6166	Phase 2
0.7273	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1182	Approved
0.726	Intermediate Similarity	NPD8166	Discontinued
0.7259	Intermediate Similarity	NPD1481	Phase 2
0.7259	Intermediate Similarity	NPD2981	Phase 2
0.725	Intermediate Similarity	NPD2860	Approved
0.725	Intermediate Similarity	NPD2859	Approved
0.7246	Intermediate Similarity	NPD3018	Phase 2
0.7236	Intermediate Similarity	NPD291	Approved
0.7234	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4140	Approved
0.723	Intermediate Similarity	NPD4357	Discontinued
0.7226	Intermediate Similarity	NPD2797	Approved
0.7222	Intermediate Similarity	NPD2161	Phase 2
0.7222	Intermediate Similarity	NPD2935	Discontinued
0.7219	Intermediate Similarity	NPD3455	Phase 2
0.7214	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3020	Approved
0.7208	Intermediate Similarity	NPD3817	Phase 2
0.72	Intermediate Similarity	NPD9697	Approved
0.7183	Intermediate Similarity	NPD5735	Approved
0.7181	Intermediate Similarity	NPD4123	Phase 3
0.7164	Intermediate Similarity	NPD1778	Approved
0.7143	Intermediate Similarity	NPD5163	Phase 2
0.7143	Intermediate Similarity	NPD7054	Approved
0.7133	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6653	Approved
0.7132	Intermediate Similarity	NPD1840	Phase 2
0.7132	Intermediate Similarity	NPD1608	Approved
0.7123	Intermediate Similarity	NPD5958	Discontinued
0.7123	Intermediate Similarity	NPD2424	Discontinued
0.7123	Intermediate Similarity	NPD4534	Discontinued
0.7123	Intermediate Similarity	NPD7153	Discontinued
0.7121	Intermediate Similarity	NPD3596	Phase 2
0.7111	Intermediate Similarity	NPD3847	Discontinued
0.7109	Intermediate Similarity	NPD5451	Approved
0.7103	Intermediate Similarity	NPD6032	Approved
0.7103	Intermediate Similarity	NPD1551	Phase 2
0.7101	Intermediate Similarity	NPD1203	Approved
0.7099	Intermediate Similarity	NPD7472	Approved
0.7099	Intermediate Similarity	NPD7074	Phase 3
0.7095	Intermediate Similarity	NPD5241	Discontinued
0.7092	Intermediate Similarity	NPD5109	Approved
0.7092	Intermediate Similarity	NPD5110	Phase 2
0.7092	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5111	Phase 2
0.7092	Intermediate Similarity	NPD5718	Phase 2
0.709	Intermediate Similarity	NPD1651	Approved
0.7083	Intermediate Similarity	NPD4536	Approved
0.7083	Intermediate Similarity	NPD4538	Approved
0.7083	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4359	Approved
0.708	Intermediate Similarity	NPD5327	Phase 3
0.7075	Intermediate Similarity	NPD4236	Phase 3
0.7075	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4237	Approved
0.7067	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD230	Phase 1
0.7063	Intermediate Similarity	NPD1933	Approved
0.7059	Intermediate Similarity	NPD9365	Approved
0.7059	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1091	Approved
0.7055	Intermediate Similarity	NPD2344	Approved
0.7055	Intermediate Similarity	NPD5763	Approved
0.7055	Intermediate Similarity	NPD5762	Approved
0.7055	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3686	Approved
0.7039	Intermediate Similarity	NPD3687	Approved
0.7037	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5960	Phase 3
0.7034	Intermediate Similarity	NPD2799	Discontinued
0.7034	Intermediate Similarity	NPD5588	Approved
0.7032	Intermediate Similarity	NPD1465	Phase 2
0.7029	Intermediate Similarity	NPD1283	Approved
0.7029	Intermediate Similarity	NPD8651	Approved
0.7029	Intermediate Similarity	NPD2922	Phase 1
0.7029	Intermediate Similarity	NPD3225	Approved
0.7027	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4625	Phase 3
0.702	Intermediate Similarity	NPD6273	Approved
0.7015	Intermediate Similarity	NPD6580	Approved
0.7015	Intermediate Similarity	NPD6581	Approved
0.7014	Intermediate Similarity	NPD2653	Approved
0.7014	Intermediate Similarity	NPD2492	Phase 1
0.7007	Intermediate Similarity	NPD1549	Phase 2
0.7007	Intermediate Similarity	NPD3972	Approved
0.7007	Intermediate Similarity	NPD7037	Approved
0.7	Intermediate Similarity	NPD6799	Approved
0.6993	Remote Similarity	NPD3111	Phase 1
0.6986	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD8127	Discontinued
0.6978	Remote Similarity	NPD987	Approved
0.6972	Remote Similarity	NPD3268	Approved
0.697	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7097	Phase 1
0.6963	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6234	Discontinued
0.6959	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6674	Discontinued
0.6959	Remote Similarity	NPD5177	Phase 3
0.6957	Remote Similarity	NPD4749	Approved
0.6954	Remote Similarity	NPD3536	Discontinued
0.6951	Remote Similarity	NPD6797	Phase 2
0.6951	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2614	Approved
0.695	Remote Similarity	NPD6832	Phase 2
0.6948	Remote Similarity	NPD4678	Approved
0.6948	Remote Similarity	NPD4380	Phase 2
0.6948	Remote Similarity	NPD4675	Approved
0.6947	Remote Similarity	NPD9377	Approved
0.6947	Remote Similarity	NPD9379	Approved
0.6939	Remote Similarity	NPD1552	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