NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	164.05
Volume:	168.852
LogP:	1.35
LogD:	1.179
LogS:	-1.38
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.393
Synthetic Accessibility Score:	2.408
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.638
MDCK Permeability:	1.3586606655735523e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	86.2394027709961%
Volume Distribution (VD):	0.652
Pgp-substrate:	11.498905181884766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.588
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.784
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.821
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	14.315
Half-life (T1/2):	0.917

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.274
AMES Toxicity:	0.708
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.403
Skin Sensitization:	0.953
Carcinogencity:	0.669
Eye Corrosion:	0.3
Eye Irritation:	0.977
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC19149

Natural Product ID:	NPC19149
*Common Name:**	Caffeoyl Aldehyde
IUPAC Name:	(E)-3-(3,4-dihydroxyphenyl)prop-2-enal
Synonyms:	Caffeoyl Aldehyde
Standard InCHIKey:	AXMVYSVVTMKQSL-OWOJBTEDSA-N
Standard InCHI:	InChI=1S/C9H8O3/c10-5-1-2-7-3-4-8(11)9(12)6-7/h1-6,11-12H/b2-1+
SMILES:	C(=Cc1ccc(c(c1)O)O)/C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL17291
PubChem CID:	5281871
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000029] Cinnamaldehydes

*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
NPO11248	Tachigalia paniculata	n.a.	n.a.	n.a.	leaves	n.a.	n.a.	PMID[12444671]
NPO8287	Piper taiwanense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8287	Piper taiwanense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11248	Tachigalia paniculata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8287	Piper taiwanense	Species	Piperaceae	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	4
Others	1

Activity Type	# Activity
Cell Line	3
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	>	30.0	ug.mL-1	PMID[523658]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[523658]
NPT762	Cell Line	A-431	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[523658]
NPT35	Others	n.a.		Activity	=	0.713	mM	PMID[523659]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	31500.0	nM	PMID[523659]

☑ 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 NPC19149 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	285
0.1-0.2	2235
0.2-0.3	6667
0.3-0.4	12909
0.4-0.5	4830
0.5-0.6	9726
0.6-0.7	4917
0.7-0.8	991
0.8-0.85	101
0.85-0.9	28
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.94	High Similarity	NPC79672
0.9216	High Similarity	NPC1075
0.9216	High Similarity	NPC294902
0.9216	High Similarity	NPC1786
0.9208	High Similarity	NPC52087
0.9192	High Similarity	NPC131587
0.9082	High Similarity	NPC286006
0.901	High Similarity	NPC110764
0.8991	High Similarity	NPC39793
0.8972	High Similarity	NPC95381
0.8962	High Similarity	NPC226250
0.89	High Similarity	NPC109955
0.8889	High Similarity	NPC107522
0.8889	High Similarity	NPC328593
0.8889	High Similarity	NPC261453
0.8889	High Similarity	NPC217472
0.8889	High Similarity	NPC33749
0.8835	High Similarity	NPC12278
0.8807	High Similarity	NPC233669
0.8807	High Similarity	NPC474967
0.8807	High Similarity	NPC278102
0.8785	High Similarity	NPC297657
0.8738	High Similarity	NPC477802
0.8738	High Similarity	NPC477801
0.8727	High Similarity	NPC281277
0.8725	High Similarity	NPC223393
0.8704	High Similarity	NPC51698
0.8649	High Similarity	NPC65791
0.8614	High Similarity	NPC283711
0.8571	High Similarity	NPC203124
0.8571	High Similarity	NPC212743
0.8571	High Similarity	NPC275519
0.8571	High Similarity	NPC309434
0.8558	High Similarity	NPC196479
0.8532	High Similarity	NPC131530
0.8515	High Similarity	NPC257182
0.85	High Similarity	NPC181709
0.8496	Intermediate Similarity	NPC141791
0.8496	Intermediate Similarity	NPC263386
0.8476	Intermediate Similarity	NPC120719
0.8476	Intermediate Similarity	NPC471511
0.8455	Intermediate Similarity	NPC264558
0.8426	Intermediate Similarity	NPC55617
0.8426	Intermediate Similarity	NPC62258
0.8421	Intermediate Similarity	NPC202474
0.8416	Intermediate Similarity	NPC32977
0.8416	Intermediate Similarity	NPC81010
0.8407	Intermediate Similarity	NPC70744
0.8407	Intermediate Similarity	NPC137537
0.8407	Intermediate Similarity	NPC272471
0.8407	Intermediate Similarity	NPC107588
0.8407	Intermediate Similarity	NPC164706
0.8396	Intermediate Similarity	NPC239291
0.8393	Intermediate Similarity	NPC277394
0.8393	Intermediate Similarity	NPC299252
0.8393	Intermediate Similarity	NPC61062
0.8349	Intermediate Similarity	NPC179309
0.8349	Intermediate Similarity	NPC174096
0.8349	Intermediate Similarity	NPC226401
0.8349	Intermediate Similarity	NPC222084
0.8349	Intermediate Similarity	NPC147634
0.8349	Intermediate Similarity	NPC79793
0.8349	Intermediate Similarity	NPC120982
0.8348	Intermediate Similarity	NPC204466
0.8348	Intermediate Similarity	NPC470849
0.8348	Intermediate Similarity	NPC470848
0.8319	Intermediate Similarity	NPC278652
0.8319	Intermediate Similarity	NPC28169
0.8319	Intermediate Similarity	NPC150919
0.8318	Intermediate Similarity	NPC477814
0.8305	Intermediate Similarity	NPC271985
0.8305	Intermediate Similarity	NPC87113
0.8288	Intermediate Similarity	NPC148969
0.8286	Intermediate Similarity	NPC94343
0.8283	Intermediate Similarity	NPC104216
0.8276	Intermediate Similarity	NPC70752
0.8276	Intermediate Similarity	NPC147654
0.8273	Intermediate Similarity	NPC139617
0.8273	Intermediate Similarity	NPC78918
0.8273	Intermediate Similarity	NPC179002
0.8273	Intermediate Similarity	NPC187583
0.8273	Intermediate Similarity	NPC257430
0.8257	Intermediate Similarity	NPC246358
0.8257	Intermediate Similarity	NPC98392
0.8257	Intermediate Similarity	NPC233731
0.8257	Intermediate Similarity	NPC36108
0.8257	Intermediate Similarity	NPC7097
0.8241	Intermediate Similarity	NPC176527
0.8224	Intermediate Similarity	NPC163734
0.8208	Intermediate Similarity	NPC304638
0.8205	Intermediate Similarity	NPC86900
0.819	Intermediate Similarity	NPC189844
0.819	Intermediate Similarity	NPC109083
0.819	Intermediate Similarity	NPC269843
0.819	Intermediate Similarity	NPC224814
0.819	Intermediate Similarity	NPC14007
0.819	Intermediate Similarity	NPC253746
0.819	Intermediate Similarity	NPC60962
0.8182	Intermediate Similarity	NPC471535
0.8174	Intermediate Similarity	NPC241634
0.8174	Intermediate Similarity	NPC117759
0.8173	Intermediate Similarity	NPC201967
0.8167	Intermediate Similarity	NPC203719
0.8167	Intermediate Similarity	NPC117237
0.8165	Intermediate Similarity	NPC233835
0.8165	Intermediate Similarity	NPC105727
0.8165	Intermediate Similarity	NPC114392
0.8165	Intermediate Similarity	NPC34864
0.8165	Intermediate Similarity	NPC58427
0.8158	Intermediate Similarity	NPC200988
0.8158	Intermediate Similarity	NPC175799
0.8158	Intermediate Similarity	NPC610
0.8158	Intermediate Similarity	NPC145023
0.8136	Intermediate Similarity	NPC474275
0.8136	Intermediate Similarity	NPC224208
0.8125	Intermediate Similarity	NPC471485
0.8119	Intermediate Similarity	NPC300017
0.8119	Intermediate Similarity	NPC312304
0.8108	Intermediate Similarity	NPC257124
0.8108	Intermediate Similarity	NPC156840
0.8108	Intermediate Similarity	NPC173746
0.8108	Intermediate Similarity	NPC8547
0.8103	Intermediate Similarity	NPC2058
0.8095	Intermediate Similarity	NPC130193
0.8091	Intermediate Similarity	NPC254833
0.8091	Intermediate Similarity	NPC228343
0.8087	Intermediate Similarity	NPC63126
0.8087	Intermediate Similarity	NPC86198
0.8067	Intermediate Similarity	NPC246704
0.8067	Intermediate Similarity	NPC20443
0.8067	Intermediate Similarity	NPC60517
0.8067	Intermediate Similarity	NPC146886
0.8061	Intermediate Similarity	NPC265146
0.8056	Intermediate Similarity	NPC219913
0.8053	Intermediate Similarity	NPC294941
0.8053	Intermediate Similarity	NPC120280
0.8051	Intermediate Similarity	NPC286573
0.8051	Intermediate Similarity	NPC114298
0.8036	Intermediate Similarity	NPC228988
0.8034	Intermediate Similarity	NPC158949
0.8017	Intermediate Similarity	NPC473787
0.8017	Intermediate Similarity	NPC470215
0.8017	Intermediate Similarity	NPC70084
0.8017	Intermediate Similarity	NPC470214
0.8017	Intermediate Similarity	NPC109371
0.8	Intermediate Similarity	NPC132921
0.8	Intermediate Similarity	NPC289459
0.7983	Intermediate Similarity	NPC106659
0.7983	Intermediate Similarity	NPC164778
0.7983	Intermediate Similarity	NPC18984
0.7983	Intermediate Similarity	NPC242372
0.7983	Intermediate Similarity	NPC4181
0.7983	Intermediate Similarity	NPC238810
0.7983	Intermediate Similarity	NPC160900
0.7983	Intermediate Similarity	NPC257976
0.7983	Intermediate Similarity	NPC229084
0.7982	Intermediate Similarity	NPC4665
0.7981	Intermediate Similarity	NPC274678
0.7981	Intermediate Similarity	NPC246679
0.798	Intermediate Similarity	NPC175313
0.798	Intermediate Similarity	NPC150837
0.798	Intermediate Similarity	NPC248817
0.7967	Intermediate Similarity	NPC298268
0.7963	Intermediate Similarity	NPC93831
0.7961	Intermediate Similarity	NPC325292
0.7961	Intermediate Similarity	NPC138117
0.7949	Intermediate Similarity	NPC265454
0.7949	Intermediate Similarity	NPC34634
0.7946	Intermediate Similarity	NPC470355
0.7946	Intermediate Similarity	NPC268032
0.7944	Intermediate Similarity	NPC471578
0.7944	Intermediate Similarity	NPC101025
0.7941	Intermediate Similarity	NPC300478
0.7934	Intermediate Similarity	NPC475695
0.7934	Intermediate Similarity	NPC147192
0.7934	Intermediate Similarity	NPC251407
0.7934	Intermediate Similarity	NPC118584
0.7934	Intermediate Similarity	NPC213552
0.7934	Intermediate Similarity	NPC120225
0.7934	Intermediate Similarity	NPC168653
0.7925	Intermediate Similarity	NPC171843
0.7921	Intermediate Similarity	NPC27974
0.7917	Intermediate Similarity	NPC273686
0.7917	Intermediate Similarity	NPC312404
0.7917	Intermediate Similarity	NPC288945
0.7913	Intermediate Similarity	NPC221049
0.7913	Intermediate Similarity	NPC111225
0.7909	Intermediate Similarity	NPC227894
0.7909	Intermediate Similarity	NPC260952
0.79	Intermediate Similarity	NPC197783
0.7881	Intermediate Similarity	NPC98305
0.7881	Intermediate Similarity	NPC294361
0.7881	Intermediate Similarity	NPC236520
0.7879	Intermediate Similarity	NPC124436
0.7876	Intermediate Similarity	NPC146422
0.787	Intermediate Similarity	NPC470202
0.787	Intermediate Similarity	NPC68269
0.787	Intermediate Similarity	NPC135784
0.7869	Intermediate Similarity	NPC476873
0.7863	Intermediate Similarity	NPC37858

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 NPC19149 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	1131
0.2-0.3	1664
0.3-0.4	3112
0.4-0.5	1663
0.5-0.6	1026
0.6-0.7	233
0.7-0.8	41
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8167	Intermediate Similarity	NPD9494	Approved
0.8108	Intermediate Similarity	NPD228	Approved
0.8091	Intermediate Similarity	NPD3021	Approved
0.8091	Intermediate Similarity	NPD3022	Approved
0.7983	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD111	Approved
0.7876	Intermediate Similarity	NPD9377	Approved
0.7876	Intermediate Similarity	NPD9379	Approved
0.7699	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD1242	Phase 1
0.7647	Intermediate Similarity	NPD9384	Approved
0.7647	Intermediate Similarity	NPD9381	Approved
0.7547	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2934	Approved
0.7547	Intermediate Similarity	NPD2933	Approved
0.7477	Intermediate Similarity	NPD2859	Approved
0.7477	Intermediate Similarity	NPD2860	Approved
0.7477	Intermediate Similarity	NPD844	Approved
0.7459	Intermediate Similarity	NPD9269	Phase 2
0.7431	Intermediate Similarity	NPD3020	Approved
0.7407	Intermediate Similarity	NPD288	Approved
0.7398	Intermediate Similarity	NPD9622	Approved
0.7395	Intermediate Similarity	NPD5536	Phase 2
0.7364	Intermediate Similarity	NPD230	Phase 1
0.7364	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD943	Approved
0.7281	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD1358	Approved
0.7273	Intermediate Similarity	NPD1357	Approved
0.7222	Intermediate Similarity	NPD9620	Approved
0.7222	Intermediate Similarity	NPD257	Approved
0.7222	Intermediate Similarity	NPD9621	Approved
0.7222	Intermediate Similarity	NPD258	Approved
0.7222	Intermediate Similarity	NPD9619	Approved
0.7218	Intermediate Similarity	NPD7266	Discontinued
0.7193	Intermediate Similarity	NPD3134	Approved
0.719	Intermediate Similarity	NPD9545	Approved
0.7177	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD9569	Approved
0.7154	Intermediate Similarity	NPD826	Approved
0.7154	Intermediate Similarity	NPD825	Approved
0.7143	Intermediate Similarity	NPD9094	Approved
0.7143	Intermediate Similarity	NPD846	Approved
0.7143	Intermediate Similarity	NPD940	Approved
0.7131	Intermediate Similarity	NPD9268	Approved
0.7099	Intermediate Similarity	NPD555	Phase 2
0.7077	Intermediate Similarity	NPD259	Phase 1
0.7068	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD9296	Approved
0.7063	Intermediate Similarity	NPD5311	Approved
0.7063	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5310	Approved
0.7059	Intermediate Similarity	NPD8166	Discontinued
0.7054	Intermediate Similarity	NPD3027	Phase 3
0.7025	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3055	Approved
0.7008	Intermediate Similarity	NPD3053	Approved
0.7007	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD597	Approved
0.7	Intermediate Similarity	NPD601	Approved
0.7	Intermediate Similarity	NPD1809	Phase 2
0.7	Intermediate Similarity	NPD598	Approved
0.6972	Remote Similarity	NPD845	Approved
0.696	Remote Similarity	NPD3092	Approved
0.6947	Remote Similarity	NPD1136	Approved
0.6947	Remote Similarity	NPD1130	Approved
0.6947	Remote Similarity	NPD1132	Approved
0.6939	Remote Similarity	NPD9087	Approved
0.6935	Remote Similarity	NPD4626	Approved
0.693	Remote Similarity	NPD9500	Approved
0.6923	Remote Similarity	NPD9536	Phase 1
0.6923	Remote Similarity	NPD2684	Approved
0.6923	Remote Similarity	NPD74	Approved
0.6923	Remote Similarity	NPD9537	Phase 1
0.6923	Remote Similarity	NPD9266	Approved
0.6917	Remote Similarity	NPD5283	Phase 1
0.6911	Remote Similarity	NPD3091	Approved
0.69	Remote Similarity	NPD9294	Approved
0.6897	Remote Similarity	NPD1445	Approved
0.6897	Remote Similarity	NPD968	Approved
0.6897	Remote Similarity	NPD1444	Approved
0.6894	Remote Similarity	NPD3062	Approved
0.6894	Remote Similarity	NPD3059	Approved
0.6894	Remote Similarity	NPD1613	Approved
0.6894	Remote Similarity	NPD3061	Approved
0.6894	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD9570	Approved
0.6885	Remote Similarity	NPD9493	Approved
0.687	Remote Similarity	NPD9610	Approved
0.687	Remote Similarity	NPD3144	Approved
0.687	Remote Similarity	NPD3145	Approved
0.687	Remote Similarity	NPD9608	Approved
0.686	Remote Similarity	NPD9618	Approved
0.686	Remote Similarity	NPD9614	Approved
0.6846	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD275	Approved
0.6842	Remote Similarity	NPD274	Approved
0.6838	Remote Similarity	NPD9264	Approved
0.6838	Remote Similarity	NPD9263	Approved
0.6838	Remote Similarity	NPD9267	Approved
0.6838	Remote Similarity	NPD290	Approved
0.6832	Remote Similarity	NPD9088	Approved
0.6818	Remote Similarity	NPD2674	Phase 3
0.68	Remote Similarity	NPD2932	Approved
0.68	Remote Similarity	NPD3019	Approved
0.6791	Remote Similarity	NPD823	Approved
0.6791	Remote Similarity	NPD5314	Approved
0.6791	Remote Similarity	NPD817	Approved
0.6777	Remote Similarity	NPD1241	Discontinued
0.6769	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3620	Phase 2
0.6767	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3496	Discontinued
0.6744	Remote Similarity	NPD3094	Phase 2
0.6742	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD9495	Approved
0.6726	Remote Similarity	NPD9273	Approved
0.6723	Remote Similarity	NPD4750	Phase 3
0.6723	Remote Similarity	NPD1792	Phase 2
0.672	Remote Similarity	NPD5691	Approved
0.6713	Remote Similarity	NPD1653	Approved
0.6695	Remote Similarity	NPD2342	Discontinued
0.6694	Remote Similarity	NPD9613	Approved
0.6694	Remote Similarity	NPD9616	Approved
0.6694	Remote Similarity	NPD7843	Approved
0.6694	Remote Similarity	NPD9615	Approved
0.6693	Remote Similarity	NPD1201	Approved
0.6667	Remote Similarity	NPD7157	Approved
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD3455	Phase 2
0.6667	Remote Similarity	NPD255	Approved
0.6642	Remote Similarity	NPD1558	Phase 1
0.6642	Remote Similarity	NPD4060	Phase 1
0.6641	Remote Similarity	NPD5736	Approved
0.664	Remote Similarity	NPD316	Approved
0.6639	Remote Similarity	NPD2234	Approved
0.6639	Remote Similarity	NPD2228	Approved
0.6639	Remote Similarity	NPD2229	Approved
0.6615	Remote Similarity	NPD1164	Approved
0.6615	Remote Similarity	NPD1470	Approved
0.6613	Remote Similarity	NPD9568	Approved
0.6612	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3028	Approved
0.6594	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD447	Suspended
0.6587	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1237	Approved
0.6571	Remote Similarity	NPD9089	Approved
0.6562	Remote Similarity	NPD422	Phase 1
0.656	Remote Similarity	NPD856	Approved
0.656	Remote Similarity	NPD317	Approved
0.656	Remote Similarity	NPD16	Approved
0.656	Remote Similarity	NPD318	Approved
0.6557	Remote Similarity	NPD7635	Approved
0.6557	Remote Similarity	NPD821	Approved
0.6552	Remote Similarity	NPD291	Approved
0.6552	Remote Similarity	NPD824	Approved
0.6549	Remote Similarity	NPD1511	Approved
0.6545	Remote Similarity	NPD9258	Approved
0.6545	Remote Similarity	NPD9256	Approved
0.6535	Remote Similarity	NPD1778	Approved
0.6535	Remote Similarity	NPD2286	Discontinued
0.6535	Remote Similarity	NPD4059	Approved
0.6535	Remote Similarity	NPD9716	Approved
0.6535	Remote Similarity	NPD3095	Discontinued
0.6532	Remote Similarity	NPD6671	Approved
0.6525	Remote Similarity	NPD9697	Approved
0.6508	Remote Similarity	NPD1548	Phase 1
0.6504	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD9261	Approved
0.6486	Remote Similarity	NPD9365	Approved
0.6476	Remote Similarity	NPD9093	Approved
0.6462	Remote Similarity	NPD2983	Phase 2
0.6462	Remote Similarity	NPD2982	Phase 2
0.6462	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD1512	Approved
0.6457	Remote Similarity	NPD4093	Discontinued
0.6455	Remote Similarity	NPD9295	Approved
0.6452	Remote Similarity	NPD1791	Approved
0.6452	Remote Similarity	NPD1793	Approved
0.6452	Remote Similarity	NPD9281	Approved
0.6444	Remote Similarity	NPD6663	Approved
0.6439	Remote Similarity	NPD6584	Phase 3
0.6434	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD3705	Approved
0.6434	Remote Similarity	NPD4357	Discontinued
0.6434	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1610	Phase 2
0.6423	Remote Similarity	NPD2492	Phase 1
0.6419	Remote Similarity	NPD1934	Approved
0.6414	Remote Similarity	NPD711	Discontinued
0.6412	Remote Similarity	NPD1283	Approved
0.6408	Remote Similarity	NPD302	Approved
0.6406	Remote Similarity	NPD1751	Approved
0.6406	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD2935	Discontinued
0.6403	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3882	Suspended

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