NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.15
Volume:	298.714
LogP:	4.248
LogD:	3.514
LogS:	-3.489
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	2.692
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.702
MDCK Permeability:	2.6820907805813476e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.591
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148
Plasma Protein Binding (PPB):	97.18716430664062%
Volume Distribution (VD):	0.979
Pgp-substrate:	3.2993786334991455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.331
CYP2C19-inhibitor:	0.739
CYP2C19-substrate:	0.109
CYP2C9-inhibitor:	0.76
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.883
CYP2D6-substrate:	0.822
CYP3A4-inhibitor:	0.39
CYP3A4-substrate:	0.186

ADMET: Excretion

Clearance (CL):	12.864
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.499
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.406
Maximum Recommended Daily Dose:	0.786
Skin Sensitization:	0.949
Carcinogencity:	0.587
Eye Corrosion:	0.4
Eye Irritation:	0.797
Respiratory Toxicity:	0.783

Download Data

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

Natural Product: NPC281277

Natural Product ID:	NPC281277
*Common Name:**	(S)-1'-Methylhexyl Caffeate
IUPAC Name:	[(2S)-heptan-2-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	(S)-1'-Methylhexyl Caffeate
Standard InCHIKey:	NCSRSZJMEGATGP-OANVXVOSSA-N
Standard InCHI:	InChI=1S/C16H22O4/c1-3-4-5-6-12(2)20-16(19)10-8-13-7-9-14(17)15(18)11-13/h7-12,17-18H,3-6H2,1-2H3/b10-8+/t12-/m0/s1
SMILES:	CCCCC[C@H](C)OC(=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641897
PubChem CID:	50901245
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO20527	Piper sanguineispicum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20954722]
NPO20527	Piper sanguineispicum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20954722]
NPO20527	Piper sanguineispicum	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

Activity Type	# Activity
Cell Line	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	89800.0	nM	PMID[526027]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	10600.0	nM	PMID[526027]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	10000.0	nM	PMID[526027]
NPT27	Others	Unspecified		IC50	=	16100.0	nM	PMID[526027]

☑ 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 NPC281277 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	226
0.1-0.2	1202
0.2-0.3	4321
0.3-0.4	10467
0.4-0.5	8202
0.5-0.6	7089
0.6-0.7	8681
0.7-0.8	2209
0.8-0.85	202
0.85-0.9	57
0.9-0.95	28
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC233669
0.9818	High Similarity	NPC309434
0.9815	High Similarity	NPC33749
0.9815	High Similarity	NPC261453
0.9815	High Similarity	NPC328593
0.9725	High Similarity	NPC474967
0.9722	High Similarity	NPC95381
0.964	High Similarity	NPC203124
0.9558	High Similarity	NPC470848
0.9558	High Similarity	NPC470849
0.955	High Similarity	NPC65791
0.9537	High Similarity	NPC226250
0.9455	High Similarity	NPC217472
0.9381	High Similarity	NPC141791
0.9381	High Similarity	NPC263386
0.9292	High Similarity	NPC275519
0.9217	High Similarity	NPC204466
0.9138	High Similarity	NPC70752
0.9138	High Similarity	NPC147654
0.913	High Similarity	NPC202474
0.9099	High Similarity	NPC131530
0.9074	High Similarity	NPC1075
0.9074	High Similarity	NPC294902
0.9074	High Similarity	NPC1786
0.9068	High Similarity	NPC20443
0.9068	High Similarity	NPC60517
0.9068	High Similarity	NPC246704
0.9068	High Similarity	NPC146886
0.9035	High Similarity	NPC200988
0.9035	High Similarity	NPC610
0.9035	High Similarity	NPC175799
0.9035	High Similarity	NPC145023
0.8992	High Similarity	NPC289459
0.8983	High Similarity	NPC474275
0.8983	High Similarity	NPC224208
0.8957	High Similarity	NPC164706
0.8957	High Similarity	NPC137537
0.8957	High Similarity	NPC86198
0.8957	High Similarity	NPC70744
0.8957	High Similarity	NPC272471
0.8957	High Similarity	NPC107588
0.8917	High Similarity	NPC120225
0.8917	High Similarity	NPC118584
0.8917	High Similarity	NPC213552
0.8879	High Similarity	NPC470214
0.8879	High Similarity	NPC70084
0.8879	High Similarity	NPC470215
0.8879	High Similarity	NPC109371
0.8879	High Similarity	NPC241634
0.885	High Similarity	NPC264558
0.8833	High Similarity	NPC67951
0.8803	High Similarity	NPC2058
0.8796	High Similarity	NPC304638
0.877	High Similarity	NPC110313
0.876	High Similarity	NPC147192
0.876	High Similarity	NPC475695
0.875	High Similarity	NPC469568
0.8727	High Similarity	NPC19149
0.8718	High Similarity	NPC37858
0.8716	High Similarity	NPC79672
0.8716	High Similarity	NPC52087
0.8704	High Similarity	NPC94343
0.8699	High Similarity	NPC30174
0.8699	High Similarity	NPC229784
0.8699	High Similarity	NPC83062
0.8699	High Similarity	NPC477294
0.8699	High Similarity	NPC477293
0.8689	High Similarity	NPC476873
0.8678	High Similarity	NPC132921
0.8678	High Similarity	NPC197832
0.8673	High Similarity	NPC139946
0.8667	High Similarity	NPC285345
0.8667	High Similarity	NPC306100
0.8649	High Similarity	NPC260952
0.864	High Similarity	NPC473285
0.8629	High Similarity	NPC329344
0.8629	High Similarity	NPC237506
0.8629	High Similarity	NPC32626
0.8629	High Similarity	NPC217052
0.8618	High Similarity	NPC232880
0.8618	High Similarity	NPC109275
0.8611	High Similarity	NPC253746
0.8609	High Similarity	NPC294941
0.8607	High Similarity	NPC168653
0.8607	High Similarity	NPC251407
0.8595	High Similarity	NPC288945
0.8584	High Similarity	NPC183700
0.8571	High Similarity	NPC254398
0.8571	High Similarity	NPC168799
0.8571	High Similarity	NPC155209
0.8571	High Similarity	NPC224814
0.8571	High Similarity	NPC60962
0.8571	High Similarity	NPC475468
0.8571	High Similarity	NPC14007
0.8571	High Similarity	NPC269843
0.8571	High Similarity	NPC189844
0.8571	High Similarity	NPC109083
0.856	High Similarity	NPC198388
0.856	High Similarity	NPC219677
0.8548	High Similarity	NPC48315
0.8547	High Similarity	NPC39793
0.8525	High Similarity	NPC280767
0.8522	High Similarity	NPC148969
0.8519	High Similarity	NPC171843
0.8512	High Similarity	NPC212541
0.8509	High Similarity	NPC297657
0.8504	High Similarity	NPC106406
0.8504	High Similarity	NPC471883
0.8504	High Similarity	NPC135127
0.8504	High Similarity	NPC471110
0.8492	Intermediate Similarity	NPC61
0.8492	Intermediate Similarity	NPC18074
0.8492	Intermediate Similarity	NPC25581
0.8492	Intermediate Similarity	NPC473924
0.8492	Intermediate Similarity	NPC5419
0.8475	Intermediate Similarity	NPC124916
0.8475	Intermediate Similarity	NPC277460
0.8468	Intermediate Similarity	NPC127676
0.8468	Intermediate Similarity	NPC478215
0.8435	Intermediate Similarity	NPC51698
0.843	Intermediate Similarity	NPC286573
0.8417	Intermediate Similarity	NPC158949
0.8413	Intermediate Similarity	NPC318799
0.8407	Intermediate Similarity	NPC206341
0.84	Intermediate Similarity	NPC477300
0.84	Intermediate Similarity	NPC226855
0.839	Intermediate Similarity	NPC122117
0.839	Intermediate Similarity	NPC278652
0.8374	Intermediate Similarity	NPC58279
0.8374	Intermediate Similarity	NPC300326
0.8372	Intermediate Similarity	NPC476699
0.8372	Intermediate Similarity	NPC157554
0.8372	Intermediate Similarity	NPC154485
0.8372	Intermediate Similarity	NPC471872
0.8361	Intermediate Similarity	NPC229084
0.8361	Intermediate Similarity	NPC106659
0.8361	Intermediate Similarity	NPC160900
0.8361	Intermediate Similarity	NPC18984
0.8359	Intermediate Similarity	NPC287597
0.8359	Intermediate Similarity	NPC886
0.8359	Intermediate Similarity	NPC34293
0.8349	Intermediate Similarity	NPC131587
0.8347	Intermediate Similarity	NPC472271
0.8333	Intermediate Similarity	NPC285361
0.832	Intermediate Similarity	NPC46192
0.8308	Intermediate Similarity	NPC126206
0.8308	Intermediate Similarity	NPC476376
0.8295	Intermediate Similarity	NPC476870
0.8291	Intermediate Similarity	NPC41851
0.8288	Intermediate Similarity	NPC196479
0.8279	Intermediate Similarity	NPC327070
0.8261	Intermediate Similarity	NPC120982
0.8261	Intermediate Similarity	NPC174096
0.8261	Intermediate Similarity	NPC226401
0.8261	Intermediate Similarity	NPC147634
0.8261	Intermediate Similarity	NPC79793
0.8261	Intermediate Similarity	NPC222084
0.8254	Intermediate Similarity	NPC64111
0.8254	Intermediate Similarity	NPC208536
0.825	Intermediate Similarity	NPC24474
0.825	Intermediate Similarity	NPC311595
0.825	Intermediate Similarity	NPC477803
0.8244	Intermediate Similarity	NPC476383
0.8244	Intermediate Similarity	NPC226005
0.8244	Intermediate Similarity	NPC197316
0.8244	Intermediate Similarity	NPC182249
0.8244	Intermediate Similarity	NPC68092
0.8244	Intermediate Similarity	NPC220942
0.8244	Intermediate Similarity	NPC64141
0.8244	Intermediate Similarity	NPC472350
0.8244	Intermediate Similarity	NPC89105
0.8244	Intermediate Similarity	NPC81515
0.8244	Intermediate Similarity	NPC100389
0.8241	Intermediate Similarity	NPC257182
0.8241	Intermediate Similarity	NPC107522
0.824	Intermediate Similarity	NPC158654
0.8235	Intermediate Similarity	NPC280001
0.8235	Intermediate Similarity	NPC164386
0.8231	Intermediate Similarity	NPC470572
0.8231	Intermediate Similarity	NPC471665
0.8231	Intermediate Similarity	NPC90431
0.8231	Intermediate Similarity	NPC120852
0.8231	Intermediate Similarity	NPC471664
0.8226	Intermediate Similarity	NPC87113
0.8226	Intermediate Similarity	NPC27352
0.8217	Intermediate Similarity	NPC111635
0.8217	Intermediate Similarity	NPC474895
0.8211	Intermediate Similarity	NPC257976
0.8211	Intermediate Similarity	NPC164778
0.8211	Intermediate Similarity	NPC4181
0.8211	Intermediate Similarity	NPC242372
0.8198	Intermediate Similarity	NPC110764
0.8197	Intermediate Similarity	NPC114845
0.8197	Intermediate Similarity	NPC177291
0.8197	Intermediate Similarity	NPC322332
0.8197	Intermediate Similarity	NPC194416
0.819	Intermediate Similarity	NPC139617
0.819	Intermediate Similarity	NPC179002
0.819	Intermediate Similarity	NPC187583
0.819	Intermediate Similarity	NPC257430

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 NPC281277 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	805
0.2-0.3	1740
0.3-0.4	2816
0.4-0.5	1836
0.5-0.6	1186
0.6-0.7	511
0.7-0.8	57
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8361	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD7266	Discontinued
0.8158	Intermediate Similarity	NPD1358	Approved
0.807	Intermediate Similarity	NPD3134	Approved
0.8034	Intermediate Similarity	NPD228	Approved
0.8017	Intermediate Similarity	NPD3022	Approved
0.8017	Intermediate Similarity	NPD3021	Approved
0.8	Intermediate Similarity	NPD230	Phase 1
0.7926	Intermediate Similarity	NPD8166	Discontinued
0.7868	Intermediate Similarity	NPD6190	Approved
0.7812	Intermediate Similarity	NPD9494	Approved
0.7787	Intermediate Similarity	NPD5536	Phase 2
0.7724	Intermediate Similarity	NPD9545	Approved
0.768	Intermediate Similarity	NPD3496	Discontinued
0.7661	Intermediate Similarity	NPD1357	Approved
0.7652	Intermediate Similarity	NPD826	Approved
0.7652	Intermediate Similarity	NPD825	Approved
0.7606	Intermediate Similarity	NPD3455	Phase 2
0.76	Intermediate Similarity	NPD4626	Approved
0.7557	Intermediate Similarity	NPD3027	Phase 3
0.752	Intermediate Similarity	NPD5691	Approved
0.7519	Intermediate Similarity	NPD4060	Phase 1
0.7463	Intermediate Similarity	NPD555	Phase 2
0.7422	Intermediate Similarity	NPD9269	Phase 2
0.7413	Intermediate Similarity	NPD1653	Approved
0.7345	Intermediate Similarity	NPD2934	Approved
0.7345	Intermediate Similarity	NPD2933	Approved
0.7333	Intermediate Similarity	NPD2684	Approved
0.7328	Intermediate Similarity	NPD257	Approved
0.7328	Intermediate Similarity	NPD258	Approved
0.7317	Intermediate Similarity	NPD5283	Phase 1
0.7315	Intermediate Similarity	NPD111	Approved
0.7313	Intermediate Similarity	NPD259	Phase 1
0.7281	Intermediate Similarity	NPD2860	Approved
0.7281	Intermediate Similarity	NPD2859	Approved
0.728	Intermediate Similarity	NPD9493	Approved
0.7273	Intermediate Similarity	NPD5736	Approved
0.7241	Intermediate Similarity	NPD3020	Approved
0.7236	Intermediate Similarity	NPD7843	Approved
0.7236	Intermediate Similarity	NPD9379	Approved
0.7236	Intermediate Similarity	NPD9377	Approved
0.7213	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD447	Suspended
0.72	Intermediate Similarity	NPD7157	Approved
0.7193	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD9384	Approved
0.7188	Intermediate Similarity	NPD9381	Approved
0.7188	Intermediate Similarity	NPD1778	Approved
0.7164	Intermediate Similarity	NPD7095	Approved
0.7163	Intermediate Similarity	NPD4628	Phase 3
0.7163	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4110	Phase 3
0.7153	Intermediate Similarity	NPD6653	Approved
0.7143	Intermediate Similarity	NPD9569	Approved
0.7133	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1613	Approved
0.7132	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3620	Phase 2
0.7132	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD844	Approved
0.7122	Intermediate Similarity	NPD2935	Discontinued
0.7111	Intermediate Similarity	NPD6798	Discontinued
0.7111	Intermediate Similarity	NPD3145	Approved
0.7111	Intermediate Similarity	NPD3144	Approved
0.7109	Intermediate Similarity	NPD9268	Approved
0.7107	Intermediate Similarity	NPD290	Approved
0.7107	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD9622	Approved
0.7097	Intermediate Similarity	NPD5535	Approved
0.708	Intermediate Similarity	NPD6355	Discontinued
0.7077	Intermediate Similarity	NPD422	Phase 1
0.7077	Intermediate Similarity	NPD3705	Approved
0.7067	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4062	Phase 3
0.7059	Intermediate Similarity	NPD6663	Approved
0.7059	Intermediate Similarity	NPD2674	Phase 3
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7043	Intermediate Similarity	NPD9296	Approved
0.7034	Intermediate Similarity	NPD1242	Phase 1
0.7016	Intermediate Similarity	NPD969	Suspended
0.7008	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD9570	Approved
0.7	Intermediate Similarity	NPD3847	Discontinued
0.6985	Remote Similarity	NPD3764	Approved
0.6977	Remote Similarity	NPD5585	Approved
0.6975	Remote Similarity	NPD291	Approved
0.6963	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4340	Discontinued
0.6957	Remote Similarity	NPD274	Approved
0.6957	Remote Similarity	NPD275	Approved
0.695	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3092	Approved
0.6942	Remote Similarity	NPD9697	Approved
0.694	Remote Similarity	NPD9621	Approved
0.694	Remote Similarity	NPD9619	Approved
0.694	Remote Similarity	NPD9620	Approved
0.694	Remote Similarity	NPD5647	Approved
0.6939	Remote Similarity	NPD3686	Approved
0.6939	Remote Similarity	NPD3687	Approved
0.6934	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4198	Discontinued
0.6929	Remote Similarity	NPD6671	Approved
0.6923	Remote Similarity	NPD288	Approved
0.6917	Remote Similarity	NPD6647	Phase 2
0.6912	Remote Similarity	NPD9537	Phase 1
0.6912	Remote Similarity	NPD9536	Phase 1
0.6905	Remote Similarity	NPD1241	Discontinued
0.6899	Remote Similarity	NPD1894	Discontinued
0.6899	Remote Similarity	NPD3091	Approved
0.6894	Remote Similarity	NPD9717	Approved
0.6892	Remote Similarity	NPD3111	Phase 1
0.6891	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD968	Approved
0.6884	Remote Similarity	NPD943	Approved
0.6884	Remote Similarity	NPD3059	Approved
0.6884	Remote Similarity	NPD3062	Approved
0.6884	Remote Similarity	NPD3061	Approved
0.6875	Remote Similarity	NPD1282	Approved
0.6867	Remote Similarity	NPD1934	Approved
0.6866	Remote Similarity	NPD3094	Phase 2
0.6866	Remote Similarity	NPD3055	Approved
0.6866	Remote Similarity	NPD3053	Approved
0.6861	Remote Similarity	NPD597	Approved
0.6861	Remote Similarity	NPD601	Approved
0.6861	Remote Similarity	NPD598	Approved
0.685	Remote Similarity	NPD2629	Approved
0.6842	Remote Similarity	NPD2982	Phase 2
0.6842	Remote Similarity	NPD3882	Suspended
0.6842	Remote Similarity	NPD2983	Phase 2
0.6842	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD846	Approved
0.6833	Remote Similarity	NPD940	Approved
0.6831	Remote Similarity	NPD5762	Approved
0.6831	Remote Similarity	NPD5763	Approved
0.6825	Remote Similarity	NPD821	Approved
0.6818	Remote Similarity	NPD1535	Discovery
0.6815	Remote Similarity	NPD6584	Phase 3
0.6812	Remote Similarity	NPD1130	Approved
0.6812	Remote Similarity	NPD1132	Approved
0.6812	Remote Similarity	NPD1136	Approved
0.6791	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1283	Approved
0.6791	Remote Similarity	NPD5310	Approved
0.6791	Remote Similarity	NPD5311	Approved
0.6786	Remote Similarity	NPD5314	Approved
0.6786	Remote Similarity	NPD2653	Approved
0.6781	Remote Similarity	NPD4357	Discontinued
0.6774	Remote Similarity	NPD74	Approved
0.6774	Remote Similarity	NPD9266	Approved
0.6767	Remote Similarity	NPD1481	Phase 2
0.6767	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD2981	Phase 2
0.6765	Remote Similarity	NPD2861	Phase 2
0.6763	Remote Similarity	NPD1558	Phase 1
0.6761	Remote Similarity	NPD6032	Approved
0.6753	Remote Similarity	NPD6234	Discontinued
0.6741	Remote Similarity	NPD987	Approved
0.6741	Remote Similarity	NPD1203	Approved
0.6741	Remote Similarity	NPD2797	Approved
0.6739	Remote Similarity	NPD411	Approved
0.6739	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1048	Approved
0.6738	Remote Similarity	NPD7097	Phase 1
0.6736	Remote Similarity	NPD3060	Approved
0.6736	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1652	Phase 2
0.6723	Remote Similarity	NPD9495	Approved
0.672	Remote Similarity	NPD2067	Discontinued
0.6719	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD4359	Approved
0.6716	Remote Similarity	NPD3685	Discontinued
0.6714	Remote Similarity	NPD5124	Phase 1
0.6714	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2801	Approved
0.6708	Remote Similarity	NPD7685	Pre-registration
0.6695	Remote Similarity	NPD1809	Phase 2
0.6694	Remote Similarity	NPD9267	Approved
0.6694	Remote Similarity	NPD9264	Approved
0.6694	Remote Similarity	NPD9263	Approved
0.6692	Remote Similarity	NPD1091	Approved
0.669	Remote Similarity	NPD651	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2799	Discontinued
0.6689	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD824	Approved
0.6667	Remote Similarity	NPD2492	Phase 1
0.6667	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD2424	Discontinued
0.6667	Remote Similarity	NPD3095	Discontinued
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD5163	Phase 2
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD2932	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD255	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