NPASS Compound

Structure

NPC474875 OpenBabel07101718202D 27 28 0 0 1 0 0 0 0 0999 V2000 -2.5085 1.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2497 0.9319 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 5.1962 2.0000 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 3.4641 3.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6980 -0.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4051 -1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6015 -1.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9568 0.2247 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 1 0 0 0 0 2 26 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 6 0 0 0 14 16 1 0 0 0 0 14 22 1 1 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 16 27 1 6 0 0 0 17 18 1 0 0 0 0 17 24 2 0 0 0 0 17 26 1 0 0 0 0 18 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.13
Volume:	366.065
LogP:	0.937
LogD:	0.53
LogS:	-1.439
# Rotatable Bonds:	7
TPSA:	153.75
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.265
Synthetic Accessibility Score:	3.59
Fsp3:	0.444
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:	-6.198
MDCK Permeability:	3.411438228795305e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.947
Human Intestinal Absorption (HIA):	0.89
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.69
Plasma Protein Binding (PPB):	58.024559020996094%
Volume Distribution (VD):	1.735
Pgp-substrate:	39.349403381347656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.244
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.797
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.072
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	10.583
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.224
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.075
AMES Toxicity:	0.173
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.477
Skin Sensitization:	0.792
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC474875

Natural Product ID:	NPC474875
*Common Name:**	HPJJCRNQEWRFQW-HTWICIHYSA-N
IUPAC Name:	n.a.
Synonyms:	Ethyl 4-O-Caffeoylquinate
Standard InCHIKey:	HPJJCRNQEWRFQW-HTWICIHYSA-N
Standard InCHI:	InChI=1S/C18H22O9/c1-2-26-17(24)18(25)8-13(21)16(14(22)9-18)27-15(23)6-4-10-3-5-11(19)12(20)7-10/h3-7,13-14,16,19-22,25H,2,8-9H2,1H3/b6-4+/t13-,14-,16-,18-/m1/s1
SMILES:	CCOC(=O)[C@]1(O)C[C@@H](O)[C@@H]([C@@H](C1)O)OC(=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485994
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002512] Quinic 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
NPO32987	vittaria anguste-elongata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124757]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	234000.0	nM	PMID[538466]

☑ 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 NPC474875 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	297
0.1-0.2	1204
0.2-0.3	3118
0.3-0.4	7027
0.4-0.5	10211
0.5-0.6	5988
0.6-0.7	8618
0.7-0.8	5827
0.8-0.85	289
0.85-0.9	58
0.9-0.95	18
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC26241
1.0	High Similarity	NPC303683
1.0	High Similarity	NPC476820
1.0	High Similarity	NPC205751
1.0	High Similarity	NPC476819
1.0	High Similarity	NPC274891
1.0	High Similarity	NPC295492
0.9924	High Similarity	NPC37250
0.9924	High Similarity	NPC278068
0.9924	High Similarity	NPC152942
0.9924	High Similarity	NPC302857
0.9924	High Similarity	NPC219428
0.9924	High Similarity	NPC142703
0.9778	High Similarity	NPC43158
0.9778	High Similarity	NPC258469
0.9778	High Similarity	NPC472016
0.9778	High Similarity	NPC277315
0.9778	High Similarity	NPC192831
0.9704	High Similarity	NPC477335
0.9704	High Similarity	NPC13818
0.9704	High Similarity	NPC206095
0.9704	High Similarity	NPC471027
0.9704	High Similarity	NPC224389
0.9704	High Similarity	NPC297517
0.9704	High Similarity	NPC35702
0.9697	High Similarity	NPC233350
0.9697	High Similarity	NPC70680
0.9697	High Similarity	NPC182217
0.9632	High Similarity	NPC319628
0.9632	High Similarity	NPC303090
0.9632	High Similarity	NPC220664
0.9632	High Similarity	NPC284948
0.9632	High Similarity	NPC37331
0.9621	High Similarity	NPC68517
0.9565	High Similarity	NPC98356
0.9429	High Similarity	NPC192568
0.9429	High Similarity	NPC471076
0.9357	High Similarity	NPC322660
0.9353	High Similarity	NPC477333
0.9338	High Similarity	NPC24295
0.9338	High Similarity	NPC283560
0.9296	High Similarity	NPC306343
0.9281	High Similarity	NPC114242
0.9281	High Similarity	NPC50221
0.9225	High Similarity	NPC42464
0.9167	High Similarity	NPC93498
0.9167	High Similarity	NPC163883
0.9155	High Similarity	NPC43123
0.9111	High Similarity	NPC168799
0.9111	High Similarity	NPC155209
0.9103	High Similarity	NPC19380
0.9103	High Similarity	NPC146277
0.9044	High Similarity	NPC474895
0.9037	High Similarity	NPC25581
0.9037	High Similarity	NPC18074
0.9037	High Similarity	NPC61
0.9037	High Similarity	NPC5419
0.9	High Similarity	NPC477277
0.9	High Similarity	NPC477278
0.8993	High Similarity	NPC156709
0.8993	High Similarity	NPC179505
0.898	High Similarity	NPC145425
0.8966	High Similarity	NPC477334
0.8963	High Similarity	NPC198388
0.8951	High Similarity	NPC229264
0.8929	High Similarity	NPC477279
0.8919	High Similarity	NPC473275
0.8919	High Similarity	NPC470896
0.8905	High Similarity	NPC106406
0.8873	High Similarity	NPC226738
0.8873	High Similarity	NPC190587
0.8873	High Similarity	NPC22176
0.8873	High Similarity	NPC121573
0.8857	High Similarity	NPC225036
0.8857	High Similarity	NPC12218
0.8857	High Similarity	NPC75763
0.8857	High Similarity	NPC105525
0.8849	High Similarity	NPC67349
0.8849	High Similarity	NPC279676
0.8836	High Similarity	NPC252979
0.8786	High Similarity	NPC239943
0.8759	High Similarity	NPC472969
0.875	High Similarity	NPC473867
0.8731	High Similarity	NPC475695
0.8723	High Similarity	NPC289690
0.8723	High Similarity	NPC288452
0.8716	High Similarity	NPC44730
0.8705	High Similarity	NPC18646
0.8699	High Similarity	NPC75945
0.8696	High Similarity	NPC471749
0.869	High Similarity	NPC221383
0.869	High Similarity	NPC299090
0.869	High Similarity	NPC283081
0.869	High Similarity	NPC143892
0.8686	High Similarity	NPC318799
0.8676	High Similarity	NPC226855
0.8649	High Similarity	NPC95498
0.8649	High Similarity	NPC246566
0.8649	High Similarity	NPC75695
0.8643	High Similarity	NPC156892
0.863	High Similarity	NPC98009
0.863	High Similarity	NPC120621
0.863	High Similarity	NPC248257
0.863	High Similarity	NPC142528
0.8613	High Similarity	NPC217052
0.8613	High Similarity	NPC329344
0.8613	High Similarity	NPC32626
0.8613	High Similarity	NPC237506
0.8611	High Similarity	NPC474692
0.8611	High Similarity	NPC229036
0.8581	High Similarity	NPC140151
0.8571	High Similarity	NPC98809
0.8571	High Similarity	NPC476394
0.8571	High Similarity	NPC92117
0.8561	High Similarity	NPC156124
0.8561	High Similarity	NPC1321
0.8561	High Similarity	NPC304929
0.8552	High Similarity	NPC108455
0.8552	High Similarity	NPC53884
0.8552	High Similarity	NPC258671
0.8543	High Similarity	NPC134925
0.854	High Similarity	NPC94810
0.8531	High Similarity	NPC38473
0.8529	High Similarity	NPC158654
0.8521	High Similarity	NPC220942
0.8514	High Similarity	NPC32197
0.8514	High Similarity	NPC473091
0.85	High Similarity	NPC135127
0.85	High Similarity	NPC248150
0.8483	Intermediate Similarity	NPC304956
0.8483	Intermediate Similarity	NPC473090
0.8477	Intermediate Similarity	NPC203757
0.8467	Intermediate Similarity	NPC327225
0.8462	Intermediate Similarity	NPC471823
0.8456	Intermediate Similarity	NPC147192
0.8456	Intermediate Similarity	NPC168653
0.8456	Intermediate Similarity	NPC251407
0.8452	Intermediate Similarity	NPC227297
0.8451	Intermediate Similarity	NPC302583
0.8451	Intermediate Similarity	NPC100558
0.8451	Intermediate Similarity	NPC310252
0.8451	Intermediate Similarity	NPC84789
0.8446	Intermediate Similarity	NPC478242
0.8444	Intermediate Similarity	NPC85565
0.8429	Intermediate Similarity	NPC307006
0.8429	Intermediate Similarity	NPC477281
0.8429	Intermediate Similarity	NPC254398
0.8429	Intermediate Similarity	NPC129889
0.8429	Intermediate Similarity	NPC19719
0.8429	Intermediate Similarity	NPC477280
0.8425	Intermediate Similarity	NPC469683
0.8417	Intermediate Similarity	NPC264145
0.8417	Intermediate Similarity	NPC108553
0.8411	Intermediate Similarity	NPC327032
0.8411	Intermediate Similarity	NPC194095
0.8411	Intermediate Similarity	NPC191046
0.8406	Intermediate Similarity	NPC229784
0.8406	Intermediate Similarity	NPC477293
0.8406	Intermediate Similarity	NPC477294
0.8403	Intermediate Similarity	NPC326065
0.8403	Intermediate Similarity	NPC9218
0.84	Intermediate Similarity	NPC106818
0.8394	Intermediate Similarity	NPC476873
0.8392	Intermediate Similarity	NPC284409
0.8382	Intermediate Similarity	NPC132921
0.838	Intermediate Similarity	NPC475111
0.838	Intermediate Similarity	NPC470572
0.8369	Intermediate Similarity	NPC34293
0.8369	Intermediate Similarity	NPC287597
0.8369	Intermediate Similarity	NPC886
0.8367	Intermediate Similarity	NPC9370
0.8367	Intermediate Similarity	NPC287495
0.8366	Intermediate Similarity	NPC226759
0.8366	Intermediate Similarity	NPC472860
0.8358	Intermediate Similarity	NPC472271
0.8358	Intermediate Similarity	NPC147654
0.8357	Intermediate Similarity	NPC327204
0.8357	Intermediate Similarity	NPC473285
0.8357	Intermediate Similarity	NPC323379
0.8357	Intermediate Similarity	NPC473924
0.8356	Intermediate Similarity	NPC469615
0.8356	Intermediate Similarity	NPC183824
0.8356	Intermediate Similarity	NPC470130
0.8356	Intermediate Similarity	NPC160378
0.8355	Intermediate Similarity	NPC156624
0.8355	Intermediate Similarity	NPC172920
0.8345	Intermediate Similarity	NPC253481
0.8345	Intermediate Similarity	NPC253722
0.8345	Intermediate Similarity	NPC296643
0.8345	Intermediate Similarity	NPC31751
0.8344	Intermediate Similarity	NPC16024
0.8344	Intermediate Similarity	NPC61152
0.8344	Intermediate Similarity	NPC44260
0.8344	Intermediate Similarity	NPC87403
0.8344	Intermediate Similarity	NPC3746
0.8344	Intermediate Similarity	NPC205037
0.8333	Intermediate Similarity	NPC232880
0.8333	Intermediate Similarity	NPC322021
0.8333	Intermediate Similarity	NPC243891
0.8333	Intermediate Similarity	NPC300329

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 NPC474875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	764
0.2-0.3	1739
0.3-0.4	2703
0.4-0.5	2020
0.5-0.6	1082
0.6-0.7	510
0.7-0.8	79
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9632	High Similarity	NPD6190	Approved
0.8561	High Similarity	NPD230	Phase 1
0.8264	Intermediate Similarity	NPD7266	Discontinued
0.8065	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD9269	Phase 2
0.7892	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD3882	Suspended
0.7818	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD9545	Approved
0.7771	Intermediate Similarity	NPD3817	Phase 2
0.7758	Intermediate Similarity	NPD7685	Pre-registration
0.7733	Intermediate Similarity	NPD4628	Phase 3
0.7716	Intermediate Similarity	NPD6166	Phase 2
0.7716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2801	Approved
0.7643	Intermediate Similarity	NPD1934	Approved
0.7639	Intermediate Similarity	NPD3027	Phase 3
0.7622	Intermediate Similarity	NPD3818	Discontinued
0.7622	Intermediate Similarity	NPD9494	Approved
0.7616	Intermediate Similarity	NPD8166	Discontinued
0.7613	Intermediate Similarity	NPD1653	Approved
0.7609	Intermediate Similarity	NPD9268	Approved
0.7595	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6797	Phase 2
0.7589	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7075	Discontinued
0.7547	Intermediate Similarity	NPD5402	Approved
0.7545	Intermediate Similarity	NPD7251	Discontinued
0.7534	Intermediate Similarity	NPD6233	Phase 2
0.7516	Intermediate Similarity	NPD6234	Discontinued
0.7484	Intermediate Similarity	NPD1512	Approved
0.7483	Intermediate Similarity	NPD943	Approved
0.747	Intermediate Similarity	NPD7054	Approved
0.747	Intermediate Similarity	NPD5844	Phase 1
0.7468	Intermediate Similarity	NPD6799	Approved
0.7452	Intermediate Similarity	NPD3455	Phase 2
0.7425	Intermediate Similarity	NPD7074	Phase 3
0.7425	Intermediate Similarity	NPD7472	Approved
0.7421	Intermediate Similarity	NPD6801	Discontinued
0.7421	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD4380	Phase 2
0.74	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7808	Phase 3
0.7391	Intermediate Similarity	NPD4965	Approved
0.7391	Intermediate Similarity	NPD4966	Approved
0.7391	Intermediate Similarity	NPD4967	Phase 2
0.7378	Intermediate Similarity	NPD6232	Discontinued
0.7375	Intermediate Similarity	NPD1465	Phase 2
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1511	Approved
0.7347	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3764	Approved
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.7325	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7228	Approved
0.7305	Intermediate Similarity	NPD3751	Discontinued
0.7257	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6386	Approved
0.725	Intermediate Similarity	NPD6385	Approved
0.7248	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1613	Approved
0.7246	Intermediate Similarity	NPD7473	Discontinued
0.7239	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2935	Discontinued
0.723	Intermediate Similarity	NPD6798	Discontinued
0.7229	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD5353	Approved
0.7215	Intermediate Similarity	NPD5403	Approved
0.7212	Intermediate Similarity	NPD7199	Phase 2
0.72	Intermediate Similarity	NPD447	Suspended
0.72	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD6599	Discontinued
0.7181	Intermediate Similarity	NPD4062	Phase 3
0.7169	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD826	Approved
0.7133	Intermediate Similarity	NPD825	Approved
0.7124	Intermediate Similarity	NPD9570	Approved
0.7122	Intermediate Similarity	NPD2629	Approved
0.7111	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8127	Discontinued
0.7097	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5536	Phase 2
0.7089	Intermediate Similarity	NPD5401	Approved
0.7089	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7819	Suspended
0.7051	Intermediate Similarity	NPD4110	Phase 3
0.7051	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5494	Approved
0.7047	Intermediate Similarity	NPD7095	Approved
0.7034	Intermediate Similarity	NPD1608	Approved
0.7024	Intermediate Similarity	NPD5242	Approved
0.702	Intermediate Similarity	NPD4060	Phase 1
0.7007	Intermediate Similarity	NPD3021	Approved
0.7007	Intermediate Similarity	NPD3022	Approved
0.6981	Remote Similarity	NPD2532	Approved
0.6981	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2533	Approved
0.6981	Remote Similarity	NPD2534	Approved
0.6981	Remote Similarity	NPD3146	Approved
0.698	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD555	Phase 2
0.6948	Remote Similarity	NPD1510	Phase 2
0.6943	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6559	Discontinued
0.6933	Remote Similarity	NPD7411	Suspended
0.6928	Remote Similarity	NPD6653	Approved
0.6923	Remote Similarity	NPD1549	Phase 2
0.6918	Remote Similarity	NPD4357	Discontinued
0.6913	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1240	Approved
0.6906	Remote Similarity	NPD228	Approved
0.6903	Remote Similarity	NPD1551	Phase 2
0.6901	Remote Similarity	NPD9493	Approved
0.6899	Remote Similarity	NPD3887	Approved
0.6899	Remote Similarity	NPD2354	Approved
0.6889	Remote Similarity	NPD6535	Approved
0.6889	Remote Similarity	NPD6534	Approved
0.6886	Remote Similarity	NPD919	Approved
0.6884	Remote Similarity	NPD2067	Discontinued
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7435	Discontinued
0.6863	Remote Similarity	NPD4340	Discontinued
0.6861	Remote Similarity	NPD1358	Approved
0.6859	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1535	Discovery
0.6846	Remote Similarity	NPD258	Approved
0.6846	Remote Similarity	NPD257	Approved
0.6842	Remote Similarity	NPD6663	Approved
0.6842	Remote Similarity	NPD259	Phase 1
0.6839	Remote Similarity	NPD7038	Approved
0.6839	Remote Similarity	NPD7039	Approved
0.6839	Remote Similarity	NPD7240	Approved
0.6835	Remote Similarity	NPD3750	Approved
0.6832	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1778	Approved
0.6828	Remote Similarity	NPD17	Approved
0.6824	Remote Similarity	NPD3926	Phase 2
0.6818	Remote Similarity	NPD1607	Approved
0.6815	Remote Similarity	NPD4534	Discontinued
0.6805	Remote Similarity	NPD1247	Approved
0.6803	Remote Similarity	NPD1481	Phase 2
0.68	Remote Similarity	NPD5736	Approved
0.6795	Remote Similarity	NPD2438	Suspended
0.6795	Remote Similarity	NPD2796	Approved
0.6793	Remote Similarity	NPD6778	Approved
0.6793	Remote Similarity	NPD6782	Approved
0.6793	Remote Similarity	NPD6779	Approved
0.6793	Remote Similarity	NPD6776	Approved
0.6793	Remote Similarity	NPD6781	Approved
0.6793	Remote Similarity	NPD6777	Approved
0.6793	Remote Similarity	NPD6780	Approved
0.6781	Remote Similarity	NPD3496	Discontinued
0.6776	Remote Similarity	NPD7699	Phase 2
0.6776	Remote Similarity	NPD7700	Phase 2
0.6774	Remote Similarity	NPD7097	Phase 1
0.6772	Remote Similarity	NPD1652	Phase 2
0.677	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2983	Phase 2
0.6757	Remote Similarity	NPD2982	Phase 2
0.6752	Remote Similarity	NPD5763	Approved
0.6752	Remote Similarity	NPD5762	Approved
0.6748	Remote Similarity	NPD3687	Approved
0.6748	Remote Similarity	NPD3686	Approved
0.6747	Remote Similarity	NPD8455	Phase 2
0.6743	Remote Similarity	NPD8368	Discontinued
0.6738	Remote Similarity	NPD8320	Phase 1
0.6738	Remote Similarity	NPD8319	Approved
0.6735	Remote Similarity	NPD422	Phase 1
0.6733	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5647	Approved
0.6715	Remote Similarity	NPD5048	Discontinued
0.6713	Remote Similarity	NPD4198	Discontinued
0.6711	Remote Similarity	NPD3225	Approved
0.6709	Remote Similarity	NPD5958	Discontinued
0.6709	Remote Similarity	NPD2424	Discontinued
0.6707	Remote Similarity	NPD3226	Approved
0.6707	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1894	Discontinued
0.6689	Remote Similarity	NPD9569	Approved
0.6689	Remote Similarity	NPD2981	Phase 2
0.6689	Remote Similarity	NPD3018	Phase 2
0.6688	Remote Similarity	NPD6100	Approved
0.6688	Remote Similarity	NPD6099	Approved
0.6686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8312	Approved
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD2797	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