NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.09
Volume:	273.146
LogP:	1.053
LogD:	0.7
LogS:	-0.704
# Rotatable Bonds:	4
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.366
Synthetic Accessibility Score:	3.482
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.696
MDCK Permeability:	8.041840374062303e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.708
Human Intestinal Absorption (HIA):	0.582
20% Bioavailability (F20%):	0.413
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.274
Plasma Protein Binding (PPB):	78.97328186035156%
Volume Distribution (VD):	1.549
Pgp-substrate:	23.984333038330078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.22
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.379
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	13.962
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.228
Rat Oral Acute Toxicity:	0.534
Maximum Recommended Daily Dose:	0.392
Skin Sensitization:	0.943
Carcinogencity:	0.185
Eye Corrosion:	0.004
Eye Irritation:	0.062
Respiratory Toxicity:	0.293

Download Data

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

Natural Product: NPC474275

Natural Product ID:	NPC474275
*Common Name:**	(2S,5R)-2,5-Dihydroxycyclopentyl) 3-(3,4-Dihydroxyphenyl)Acrylate
IUPAC Name:	[(2S,5R)-2,5-dihydroxycyclopentyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	XYGMVEGBGQSULF-RQEVDEIRSA-N
Standard InCHI:	InChI=1S/C14H16O6/c15-9-3-1-8(7-12(9)18)2-6-13(19)20-14-10(16)4-5-11(14)17/h1-3,6-7,10-11,14-18H,4-5H2/b6-2+/t10-,11+,14?
SMILES:	C1CC(C(C1O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464608
PubChem CID:	9903815
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
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917288]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO24693	Prunus cerasus	Species	Rosaceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	80.0	%	PMID[543914]

☑ 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 NPC474275 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	273
0.1-0.2	1204
0.2-0.3	3775
0.3-0.4	9589
0.4-0.5	9473
0.5-0.6	7670
0.6-0.7	8545
0.7-0.8	1959
0.8-0.85	175
0.85-0.9	30
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC224208
0.9138	High Similarity	NPC217472
0.9068	High Similarity	NPC65791
0.906	High Similarity	NPC233669
0.9032	High Similarity	NPC476873
0.8983	High Similarity	NPC281277
0.8974	High Similarity	NPC33749
0.8974	High Similarity	NPC261453
0.8974	High Similarity	NPC328593
0.896	High Similarity	NPC232880
0.8898	High Similarity	NPC219677
0.8898	High Similarity	NPC474967
0.8889	High Similarity	NPC95381
0.8889	High Similarity	NPC229784
0.8889	High Similarity	NPC477293
0.8889	High Similarity	NPC477294
0.8833	High Similarity	NPC309434
0.8828	High Similarity	NPC473924
0.88	High Similarity	NPC475695
0.876	High Similarity	NPC254398
0.8718	High Similarity	NPC226250
0.8699	High Similarity	NPC147654
0.8692	High Similarity	NPC474895
0.8692	High Similarity	NPC471883
0.8682	High Similarity	NPC473285
0.8678	High Similarity	NPC203124
0.8651	High Similarity	NPC147192
0.8651	High Similarity	NPC251407
0.8651	High Similarity	NPC168653
0.8618	High Similarity	NPC470848
0.8618	High Similarity	NPC204466
0.8618	High Similarity	NPC470849
0.8607	High Similarity	NPC263386
0.8607	High Similarity	NPC141791
0.8594	High Similarity	NPC48315
0.8571	High Similarity	NPC132921
0.8561	High Similarity	NPC470572
0.855	High Similarity	NPC135127
0.855	High Similarity	NPC287597
0.855	High Similarity	NPC34293
0.855	High Similarity	NPC886
0.8548	High Similarity	NPC70752
0.8537	High Similarity	NPC202474
0.8525	High Similarity	NPC275519
0.8516	High Similarity	NPC109275
0.8487	Intermediate Similarity	NPC131530
0.8485	Intermediate Similarity	NPC476870
0.8468	Intermediate Similarity	NPC476872
0.8448	Intermediate Similarity	NPC1075
0.8448	Intermediate Similarity	NPC294902
0.8448	Intermediate Similarity	NPC1786
0.8433	Intermediate Similarity	NPC321184
0.8433	Intermediate Similarity	NPC321638
0.8433	Intermediate Similarity	NPC171134
0.8433	Intermediate Similarity	NPC226005
0.8433	Intermediate Similarity	NPC220942
0.8433	Intermediate Similarity	NPC328273
0.8421	Intermediate Similarity	NPC186418
0.8421	Intermediate Similarity	NPC157554
0.8421	Intermediate Similarity	NPC471664
0.8421	Intermediate Similarity	NPC471665
0.8417	Intermediate Similarity	NPC264558
0.8413	Intermediate Similarity	NPC212541
0.84	Intermediate Similarity	NPC11724
0.8385	Intermediate Similarity	NPC217052
0.8385	Intermediate Similarity	NPC329344
0.8385	Intermediate Similarity	NPC32626
0.8385	Intermediate Similarity	NPC237506
0.8374	Intermediate Similarity	NPC137537
0.8374	Intermediate Similarity	NPC272471
0.8374	Intermediate Similarity	NPC107588
0.8374	Intermediate Similarity	NPC70744
0.8374	Intermediate Similarity	NPC164706
0.8358	Intermediate Similarity	NPC78363
0.8358	Intermediate Similarity	NPC476376
0.8358	Intermediate Similarity	NPC260425
0.8358	Intermediate Similarity	NPC126206
0.8346	Intermediate Similarity	NPC469568
0.8346	Intermediate Similarity	NPC246704
0.8346	Intermediate Similarity	NPC146886
0.8346	Intermediate Similarity	NPC20443
0.8346	Intermediate Similarity	NPC60517
0.8345	Intermediate Similarity	NPC18789
0.8333	Intermediate Similarity	NPC52097
0.8321	Intermediate Similarity	NPC198388
0.8321	Intermediate Similarity	NPC318799
0.8306	Intermediate Similarity	NPC470215
0.8306	Intermediate Similarity	NPC470214
0.8306	Intermediate Similarity	NPC241634
0.8306	Intermediate Similarity	NPC109371
0.8296	Intermediate Similarity	NPC100389
0.8296	Intermediate Similarity	NPC89105
0.8296	Intermediate Similarity	NPC37250
0.8296	Intermediate Similarity	NPC205195
0.8296	Intermediate Similarity	NPC152942
0.8296	Intermediate Similarity	NPC302857
0.8296	Intermediate Similarity	NPC197316
0.8296	Intermediate Similarity	NPC142703
0.8296	Intermediate Similarity	NPC278068
0.8296	Intermediate Similarity	NPC81515
0.8296	Intermediate Similarity	NPC64141
0.8296	Intermediate Similarity	NPC476383
0.8296	Intermediate Similarity	NPC472350
0.8296	Intermediate Similarity	NPC68092
0.8296	Intermediate Similarity	NPC219428
0.8281	Intermediate Similarity	NPC58279
0.8281	Intermediate Similarity	NPC300326
0.8281	Intermediate Similarity	NPC126991
0.8281	Intermediate Similarity	NPC289459
0.8281	Intermediate Similarity	NPC27352
0.8281	Intermediate Similarity	NPC83218
0.8271	Intermediate Similarity	NPC106406
0.8258	Intermediate Similarity	NPC25581
0.8258	Intermediate Similarity	NPC5419
0.8258	Intermediate Similarity	NPC61
0.8258	Intermediate Similarity	NPC18074
0.8254	Intermediate Similarity	NPC470804
0.824	Intermediate Similarity	NPC2058
0.8235	Intermediate Similarity	NPC202700
0.8235	Intermediate Similarity	NPC474875
0.8235	Intermediate Similarity	NPC476820
0.8235	Intermediate Similarity	NPC295492
0.8235	Intermediate Similarity	NPC205751
0.8235	Intermediate Similarity	NPC303683
0.8235	Intermediate Similarity	NPC274891
0.8235	Intermediate Similarity	NPC26241
0.8235	Intermediate Similarity	NPC476819
0.8226	Intermediate Similarity	NPC86198
0.8217	Intermediate Similarity	NPC61181
0.8217	Intermediate Similarity	NPC471157
0.8217	Intermediate Similarity	NPC120225
0.8217	Intermediate Similarity	NPC118584
0.8217	Intermediate Similarity	NPC213552
0.8195	Intermediate Similarity	NPC155209
0.8195	Intermediate Similarity	NPC168799
0.8188	Intermediate Similarity	NPC105005
0.8188	Intermediate Similarity	NPC40305
0.8175	Intermediate Similarity	NPC476385
0.8175	Intermediate Similarity	NPC134405
0.8175	Intermediate Similarity	NPC476377
0.8175	Intermediate Similarity	NPC186406
0.8175	Intermediate Similarity	NPC47471
0.8168	Intermediate Similarity	NPC30174
0.8168	Intermediate Similarity	NPC226855
0.816	Intermediate Similarity	NPC70084
0.816	Intermediate Similarity	NPC477803
0.816	Intermediate Similarity	NPC37858
0.8154	Intermediate Similarity	NPC45224
0.8154	Intermediate Similarity	NPC103533
0.8154	Intermediate Similarity	NPC471881
0.8154	Intermediate Similarity	NPC471882
0.8154	Intermediate Similarity	NPC156692
0.8154	Intermediate Similarity	NPC35288
0.8154	Intermediate Similarity	NPC173150
0.8148	Intermediate Similarity	NPC471872
0.8148	Intermediate Similarity	NPC37468
0.8148	Intermediate Similarity	NPC154485
0.8145	Intermediate Similarity	NPC145023
0.8145	Intermediate Similarity	NPC175799
0.8145	Intermediate Similarity	NPC610
0.8145	Intermediate Similarity	NPC200988
0.814	Intermediate Similarity	NPC67951
0.8136	Intermediate Similarity	NPC19149
0.8134	Intermediate Similarity	NPC471110
0.8134	Intermediate Similarity	NPC67247
0.8134	Intermediate Similarity	NPC249791
0.8134	Intermediate Similarity	NPC237594
0.8134	Intermediate Similarity	NPC119060
0.8134	Intermediate Similarity	NPC476387
0.8129	Intermediate Similarity	NPC110063
0.8129	Intermediate Similarity	NPC196063
0.8129	Intermediate Similarity	NPC141455
0.8129	Intermediate Similarity	NPC297342
0.8129	Intermediate Similarity	NPC296954
0.8129	Intermediate Similarity	NPC300894
0.8125	Intermediate Similarity	NPC473451
0.8125	Intermediate Similarity	NPC285345
0.8116	Intermediate Similarity	NPC477335
0.8116	Intermediate Similarity	NPC140502
0.8116	Intermediate Similarity	NPC297517
0.8116	Intermediate Similarity	NPC471027
0.8116	Intermediate Similarity	NPC157816
0.8116	Intermediate Similarity	NPC222433
0.8116	Intermediate Similarity	NPC265648
0.8116	Intermediate Similarity	NPC13818
0.8116	Intermediate Similarity	NPC224389
0.8116	Intermediate Similarity	NPC67467
0.8116	Intermediate Similarity	NPC35702
0.8116	Intermediate Similarity	NPC206095
0.811	Intermediate Similarity	NPC322332
0.811	Intermediate Similarity	NPC266045
0.8102	Intermediate Similarity	NPC475530
0.8102	Intermediate Similarity	NPC12218
0.8102	Intermediate Similarity	NPC473799
0.8102	Intermediate Similarity	NPC105525
0.8102	Intermediate Similarity	NPC75763
0.8102	Intermediate Similarity	NPC225036
0.8095	Intermediate Similarity	NPC35071
0.8095	Intermediate Similarity	NPC177475
0.8095	Intermediate Similarity	NPC148615

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 NPC474275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	743
0.2-0.3	1915
0.3-0.4	2900
0.4-0.5	1828
0.5-0.6	1180
0.6-0.7	348
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8296	Intermediate Similarity	NPD7266	Discontinued
0.8058	Intermediate Similarity	NPD6190	Approved
0.7926	Intermediate Similarity	NPD230	Phase 1
0.7724	Intermediate Similarity	NPD1653	Approved
0.771	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3027	Phase 3
0.7623	Intermediate Similarity	NPD1358	Approved
0.752	Intermediate Similarity	NPD228	Approved
0.7464	Intermediate Similarity	NPD1613	Approved
0.7464	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD1357	Approved
0.7385	Intermediate Similarity	NPD9545	Approved
0.7368	Intermediate Similarity	NPD9269	Phase 2
0.7357	Intermediate Similarity	NPD6653	Approved
0.7353	Intermediate Similarity	NPD9494	Approved
0.7258	Intermediate Similarity	NPD3134	Approved
0.7241	Intermediate Similarity	NPD8166	Discontinued
0.7222	Intermediate Similarity	NPD3021	Approved
0.7222	Intermediate Similarity	NPD3022	Approved
0.7206	Intermediate Similarity	NPD3094	Phase 2
0.7205	Intermediate Similarity	NPD7685	Pre-registration
0.7176	Intermediate Similarity	NPD5536	Phase 2
0.7174	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9384	Approved
0.7143	Intermediate Similarity	NPD9381	Approved
0.7109	Intermediate Similarity	NPD969	Suspended
0.7101	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD826	Approved
0.7092	Intermediate Similarity	NPD825	Approved
0.709	Intermediate Similarity	NPD3496	Discontinued
0.7086	Intermediate Similarity	NPD3455	Phase 2
0.7083	Intermediate Similarity	NPD9570	Approved
0.7068	Intermediate Similarity	NPD9268	Approved
0.7042	Intermediate Similarity	NPD447	Suspended
0.7037	Intermediate Similarity	NPD1091	Approved
0.7037	Intermediate Similarity	NPD3705	Approved
0.7031	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4628	Phase 3
0.698	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4060	Phase 1
0.6972	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3620	Phase 2
0.697	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1652	Phase 2
0.6934	Remote Similarity	NPD9622	Approved
0.6929	Remote Similarity	NPD290	Approved
0.6923	Remote Similarity	NPD555	Phase 2
0.6912	Remote Similarity	NPD3092	Approved
0.6912	Remote Similarity	NPD422	Phase 1
0.6908	Remote Similarity	NPD3686	Approved
0.6908	Remote Similarity	NPD3687	Approved
0.6892	Remote Similarity	NPD4110	Phase 3
0.6892	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1778	Approved
0.6889	Remote Similarity	NPD4626	Approved
0.6875	Remote Similarity	NPD2684	Approved
0.6857	Remote Similarity	NPD2861	Phase 2
0.6857	Remote Similarity	NPD5736	Approved
0.6855	Remote Similarity	NPD1242	Phase 1
0.6852	Remote Similarity	NPD3818	Discontinued
0.6842	Remote Similarity	NPD9493	Approved
0.6839	Remote Similarity	NPD1934	Approved
0.6835	Remote Similarity	NPD6234	Discontinued
0.6831	Remote Similarity	NPD3764	Approved
0.6815	Remote Similarity	NPD5691	Approved
0.6815	Remote Similarity	NPD3882	Suspended
0.6806	Remote Similarity	NPD4340	Discontinued
0.6806	Remote Similarity	NPD6355	Discontinued
0.6803	Remote Similarity	NPD5763	Approved
0.6803	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5762	Approved
0.68	Remote Similarity	NPD291	Approved
0.6797	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD9377	Approved
0.6794	Remote Similarity	NPD9379	Approved
0.6794	Remote Similarity	NPD7843	Approved
0.6786	Remote Similarity	NPD258	Approved
0.6786	Remote Similarity	NPD257	Approved
0.6786	Remote Similarity	NPD9619	Approved
0.6786	Remote Similarity	NPD9621	Approved
0.6786	Remote Similarity	NPD9620	Approved
0.6786	Remote Similarity	NPD5647	Approved
0.6783	Remote Similarity	NPD6233	Phase 2
0.6783	Remote Similarity	NPD259	Phase 1
0.6783	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7157	Approved
0.6755	Remote Similarity	NPD1511	Approved
0.6755	Remote Similarity	NPD4357	Discontinued
0.675	Remote Similarity	NPD8127	Discontinued
0.6742	Remote Similarity	NPD5283	Phase 1
0.6738	Remote Similarity	NPD9569	Approved
0.6736	Remote Similarity	NPD943	Approved
0.6736	Remote Similarity	NPD3059	Approved
0.6736	Remote Similarity	NPD4140	Approved
0.6736	Remote Similarity	NPD3062	Approved
0.6736	Remote Similarity	NPD3061	Approved
0.6735	Remote Similarity	NPD2935	Discontinued
0.6731	Remote Similarity	NPD37	Approved
0.6727	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6362	Approved
0.6713	Remote Similarity	NPD601	Approved
0.6713	Remote Similarity	NPD597	Approved
0.6713	Remote Similarity	NPD598	Approved
0.6709	Remote Similarity	NPD4965	Approved
0.6709	Remote Similarity	NPD4967	Phase 2
0.6709	Remote Similarity	NPD4966	Approved
0.6691	Remote Similarity	NPD2982	Phase 2
0.6691	Remote Similarity	NPD2983	Phase 2
0.6689	Remote Similarity	NPD6002	Phase 3
0.6689	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6005	Phase 3
0.6689	Remote Similarity	NPD6004	Phase 3
0.6688	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD1132	Approved
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1136	Approved
0.6667	Remote Similarity	NPD1130	Approved
0.6667	Remote Similarity	NPD1512	Approved
0.6647	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3817	Phase 2
0.6646	Remote Similarity	NPD7228	Approved
0.6644	Remote Similarity	NPD2424	Discontinued
0.6644	Remote Similarity	NPD5314	Approved
0.6643	Remote Similarity	NPD7095	Approved
0.6627	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6166	Phase 2
0.6621	Remote Similarity	NPD1558	Phase 1
0.6619	Remote Similarity	NPD2981	Phase 2
0.6618	Remote Similarity	NPD3091	Approved
0.6606	Remote Similarity	NPD5844	Phase 1
0.6606	Remote Similarity	NPD7054	Approved
0.6603	Remote Similarity	NPD4380	Phase 2
0.66	Remote Similarity	NPD4236	Phase 3
0.66	Remote Similarity	NPD4237	Approved
0.6597	Remote Similarity	NPD3144	Approved
0.6597	Remote Similarity	NPD3145	Approved
0.6597	Remote Similarity	NPD6798	Discontinued
0.6589	Remote Similarity	NPD968	Approved
0.6585	Remote Similarity	NPD2933	Approved
0.6585	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD9296	Approved
0.6585	Remote Similarity	NPD2934	Approved
0.6582	Remote Similarity	NPD1465	Phase 2
0.6577	Remote Similarity	NPD1375	Discontinued
0.6575	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5124	Phase 1
0.6575	Remote Similarity	NPD5735	Approved
0.6566	Remote Similarity	NPD7472	Approved
0.6566	Remote Similarity	NPD7074	Phase 3
0.6558	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7033	Discontinued
0.6552	Remote Similarity	NPD4062	Phase 3
0.6552	Remote Similarity	NPD2674	Phase 3
0.6547	Remote Similarity	NPD1535	Discovery
0.6543	Remote Similarity	NPD7199	Phase 2
0.6541	Remote Similarity	NPD5402	Approved
0.6538	Remote Similarity	NPD3111	Phase 1
0.6535	Remote Similarity	NPD846	Approved
0.6535	Remote Similarity	NPD940	Approved
0.6533	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD2859	Approved
0.6532	Remote Similarity	NPD2860	Approved
0.6532	Remote Similarity	NPD844	Approved
0.6531	Remote Similarity	NPD823	Approved
0.6531	Remote Similarity	NPD817	Approved
0.6528	Remote Similarity	NPD9537	Phase 1
0.6528	Remote Similarity	NPD9536	Phase 1
0.6527	Remote Similarity	NPD6797	Phase 2
0.6525	Remote Similarity	NPD3225	Approved
0.6516	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD9697	Approved
0.651	Remote Similarity	NPD1551	Phase 2
0.6508	Remote Similarity	NPD3020	Approved
0.6503	Remote Similarity	NPD3018	Phase 2
0.65	Remote Similarity	NPD1481	Phase 2
0.65	Remote Similarity	NPD9717	Approved
0.6496	Remote Similarity	NPD1548	Phase 1
0.6494	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.649	Remote Similarity	NPD3060	Approved
0.649	Remote Similarity	NPD6674	Discontinued
0.6489	Remote Similarity	NPD74	Approved
0.6489	Remote Similarity	NPD9266	Approved
0.6488	Remote Similarity	NPD7251	Discontinued
0.6484	Remote Similarity	NPD6647	Phase 2
0.6484	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD1048	Approved
0.6479	Remote Similarity	NPD1203	Approved
0.6478	Remote Similarity	NPD2977	Approved
0.6478	Remote Similarity	NPD2978	Approved
0.6463	Remote Similarity	NPD275	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