NPASS Compound

Structure

NPC70680 OpenBabel07101718182D 25 26 0 0 1 0 0 0 0 0999 V2000 1.9319 -1.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 6.0622 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7071 -2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 -3.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9239 -2.3827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 -2.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 5 1 0 0 0 0 2 10 2 0 0 0 0 3 6 2 0 0 0 0 3 10 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 1 0 0 0 13 15 1 0 0 0 0 13 25 1 6 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 21 1 1 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.18
Volume:	388.895
LogP:	5.389
LogD:	3.738
LogS:	-4.231
# Rotatable Bonds:	5
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	3.313
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.805
MDCK Permeability:	1.7094251234084368e-05
Pgp-inhibitor:	0.481
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.295
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	97.20207214355469%
Volume Distribution (VD):	1.236
Pgp-substrate:	4.427156448364258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.822
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.928
CYP2C19-substrate:	0.666
CYP2C9-inhibitor:	0.783
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.675
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.453
CYP3A4-substrate:	0.593

ADMET: Excretion

Clearance (CL):	11.876
Half-life (T1/2):	0.342

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.521
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.311
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.934
Carcinogencity:	0.129
Eye Corrosion:	0.003
Eye Irritation:	0.712
Respiratory Toxicity:	0.671

Download Data

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

Natural Product: NPC70680

Natural Product ID:	NPC70680
*Common Name:**	5-O-Trans-Coumaroylquinic Acid Methyl Ester
IUPAC Name:	methyl (1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate
Synonyms:
Standard InCHIKey:	WZYLCZULUZFCHF-YKTSSCPESA-N
Standard InCHI:	InChI=1S/C17H20O8/c1-24-16(22)17(23)8-12(19)15(21)13(9-17)25-14(20)7-4-10-2-5-11(18)6-3-10/h2-7,12-13,15,18-19,21,23H,8-9H2,1H3/b7-4+/t12-,13-,15-,17+/m1/s1
SMILES:	COC(=O)[C@]1(O)C[C@@H](O)[C@H]([C@@H](C1)OC(=O)/C=C/c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2349429
PubChem CID:	14018342
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
NPO33307	pimpinella brachycarpa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23462643]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	108.8	%	PMID[567225]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	81970.0	nM	PMID[567225]

☑ 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 NPC70680 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	282
0.1-0.2	1146
0.2-0.3	2848
0.3-0.4	6467
0.4-0.5	10150
0.5-0.6	6657
0.6-0.7	9250
0.7-0.8	5604
0.8-0.85	215
0.85-0.9	27
0.9-0.95	29
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233350
1.0	High Similarity	NPC182217
0.9922	High Similarity	NPC68517
0.9697	High Similarity	NPC474875
0.9697	High Similarity	NPC476820
0.9697	High Similarity	NPC303683
0.9697	High Similarity	NPC295492
0.9697	High Similarity	NPC274891
0.9697	High Similarity	NPC26241
0.9697	High Similarity	NPC476819
0.9697	High Similarity	NPC205751
0.9621	High Similarity	NPC278068
0.9621	High Similarity	NPC24295
0.9621	High Similarity	NPC152942
0.9621	High Similarity	NPC142703
0.9621	High Similarity	NPC37250
0.9621	High Similarity	NPC219428
0.9621	High Similarity	NPC302857
0.9621	High Similarity	NPC283560
0.9481	High Similarity	NPC258469
0.9481	High Similarity	NPC192831
0.9481	High Similarity	NPC472016
0.9481	High Similarity	NPC43158
0.9481	High Similarity	NPC277315
0.9407	High Similarity	NPC206095
0.9407	High Similarity	NPC471027
0.9407	High Similarity	NPC13818
0.9407	High Similarity	NPC224389
0.9407	High Similarity	NPC35702
0.9407	High Similarity	NPC297517
0.9407	High Similarity	NPC477335
0.9338	High Similarity	NPC319628
0.9338	High Similarity	NPC303090
0.9338	High Similarity	NPC284948
0.9338	High Similarity	NPC37331
0.9338	High Similarity	NPC220664
0.9275	High Similarity	NPC98356
0.9143	High Similarity	NPC192568
0.9143	High Similarity	NPC471076
0.9071	High Similarity	NPC322660
0.9065	High Similarity	NPC477333
0.9014	High Similarity	NPC306343
0.8993	High Similarity	NPC50221
0.8993	High Similarity	NPC114242
0.8944	High Similarity	NPC42464
0.8889	High Similarity	NPC163883
0.8889	High Similarity	NPC93498
0.8873	High Similarity	NPC43123
0.8828	High Similarity	NPC19380
0.8828	High Similarity	NPC146277
0.8815	High Similarity	NPC168799
0.8815	High Similarity	NPC155209
0.875	High Similarity	NPC474895
0.8741	High Similarity	NPC5419
0.8741	High Similarity	NPC61
0.8741	High Similarity	NPC18074
0.8741	High Similarity	NPC25581
0.8714	High Similarity	NPC477277
0.8714	High Similarity	NPC477278
0.8707	High Similarity	NPC145425
0.8705	High Similarity	NPC179505
0.8705	High Similarity	NPC156709
0.869	High Similarity	NPC477334
0.8676	High Similarity	NPC477281
0.8676	High Similarity	NPC477280
0.8676	High Similarity	NPC19719
0.8671	High Similarity	NPC229264
0.8667	High Similarity	NPC108553
0.8667	High Similarity	NPC198388
0.8649	High Similarity	NPC470896
0.8649	High Similarity	NPC473275
0.8643	High Similarity	NPC477279
0.8613	High Similarity	NPC106406
0.8603	High Similarity	NPC323379
0.8603	High Similarity	NPC327204
0.8592	High Similarity	NPC22176
0.8592	High Similarity	NPC190587
0.8592	High Similarity	NPC121573
0.8592	High Similarity	NPC226738
0.8571	High Similarity	NPC75763
0.8571	High Similarity	NPC105525
0.8571	High Similarity	NPC225036
0.8571	High Similarity	NPC12218
0.8562	High Similarity	NPC252979
0.8561	High Similarity	NPC279676
0.8561	High Similarity	NPC67349
0.85	High Similarity	NPC239943
0.8483	Intermediate Similarity	NPC472969
0.8472	Intermediate Similarity	NPC473867
0.8446	Intermediate Similarity	NPC44730
0.844	Intermediate Similarity	NPC288452
0.844	Intermediate Similarity	NPC289690
0.8433	Intermediate Similarity	NPC475695
0.8425	Intermediate Similarity	NPC75945
0.8417	Intermediate Similarity	NPC18646
0.8414	Intermediate Similarity	NPC283081
0.8414	Intermediate Similarity	NPC299090
0.8414	Intermediate Similarity	NPC221383
0.8414	Intermediate Similarity	NPC143892
0.8406	Intermediate Similarity	NPC471749
0.8406	Intermediate Similarity	NPC114116
0.8394	Intermediate Similarity	NPC318799
0.8382	Intermediate Similarity	NPC226855
0.8378	Intermediate Similarity	NPC95498
0.8378	Intermediate Similarity	NPC246566
0.8378	Intermediate Similarity	NPC75695
0.8367	Intermediate Similarity	NPC473091
0.8357	Intermediate Similarity	NPC156892
0.8356	Intermediate Similarity	NPC120621
0.8356	Intermediate Similarity	NPC248257
0.8356	Intermediate Similarity	NPC142528
0.8356	Intermediate Similarity	NPC98009
0.8333	Intermediate Similarity	NPC304956
0.8333	Intermediate Similarity	NPC474692
0.8333	Intermediate Similarity	NPC229036
0.8333	Intermediate Similarity	NPC473090
0.8321	Intermediate Similarity	NPC329344
0.8321	Intermediate Similarity	NPC217052
0.8321	Intermediate Similarity	NPC32626
0.8321	Intermediate Similarity	NPC237506
0.8311	Intermediate Similarity	NPC140151
0.8299	Intermediate Similarity	NPC98809
0.8299	Intermediate Similarity	NPC92117
0.8299	Intermediate Similarity	NPC476394
0.8296	Intermediate Similarity	NPC471157
0.8278	Intermediate Similarity	NPC134925
0.8276	Intermediate Similarity	NPC258671
0.8276	Intermediate Similarity	NPC53884
0.8276	Intermediate Similarity	NPC108455
0.8273	Intermediate Similarity	NPC156124
0.8273	Intermediate Similarity	NPC1321
0.8273	Intermediate Similarity	NPC304929
0.8264	Intermediate Similarity	NPC478250
0.8261	Intermediate Similarity	NPC281798
0.8261	Intermediate Similarity	NPC473777
0.8252	Intermediate Similarity	NPC38473
0.8248	Intermediate Similarity	NPC94810
0.8243	Intermediate Similarity	NPC44378
0.8243	Intermediate Similarity	NPC280753
0.8243	Intermediate Similarity	NPC32197
0.8239	Intermediate Similarity	NPC220942
0.8235	Intermediate Similarity	NPC158654
0.8231	Intermediate Similarity	NPC81835
0.8227	Intermediate Similarity	NPC64230
0.8227	Intermediate Similarity	NPC471345
0.8227	Intermediate Similarity	NPC71638
0.8222	Intermediate Similarity	NPC126991
0.8222	Intermediate Similarity	NPC83218
0.8219	Intermediate Similarity	NPC143246
0.8219	Intermediate Similarity	NPC475539
0.8219	Intermediate Similarity	NPC119773
0.8219	Intermediate Similarity	NPC474268
0.8214	Intermediate Similarity	NPC135127
0.8214	Intermediate Similarity	NPC248150
0.8212	Intermediate Similarity	NPC203757
0.8209	Intermediate Similarity	NPC14141
0.8205	Intermediate Similarity	NPC471823
0.8201	Intermediate Similarity	NPC302844
0.82	Intermediate Similarity	NPC327225
0.8194	Intermediate Similarity	NPC130485
0.8194	Intermediate Similarity	NPC227297
0.8194	Intermediate Similarity	NPC161151
0.8188	Intermediate Similarity	NPC119252
0.8188	Intermediate Similarity	NPC56204
0.8182	Intermediate Similarity	NPC475045
0.8176	Intermediate Similarity	NPC478242
0.8175	Intermediate Similarity	NPC79332
0.8169	Intermediate Similarity	NPC302583
0.8169	Intermediate Similarity	NPC310252
0.8169	Intermediate Similarity	NPC100558
0.8169	Intermediate Similarity	NPC84789
0.8162	Intermediate Similarity	NPC61181
0.8162	Intermediate Similarity	NPC251407
0.8162	Intermediate Similarity	NPC147192
0.8162	Intermediate Similarity	NPC110211
0.8162	Intermediate Similarity	NPC168653
0.8151	Intermediate Similarity	NPC469683
0.8151	Intermediate Similarity	NPC475528
0.8148	Intermediate Similarity	NPC85565
0.8146	Intermediate Similarity	NPC194095
0.8146	Intermediate Similarity	NPC327032
0.8146	Intermediate Similarity	NPC191046
0.8143	Intermediate Similarity	NPC215484
0.8143	Intermediate Similarity	NPC254398
0.8143	Intermediate Similarity	NPC129889
0.8143	Intermediate Similarity	NPC307006
0.8134	Intermediate Similarity	NPC52097
0.8133	Intermediate Similarity	NPC106818
0.8133	Intermediate Similarity	NPC36130
0.8133	Intermediate Similarity	NPC134905
0.8133	Intermediate Similarity	NPC205918
0.8129	Intermediate Similarity	NPC264145
0.8125	Intermediate Similarity	NPC326065
0.8125	Intermediate Similarity	NPC9218
0.8125	Intermediate Similarity	NPC136649
0.8121	Intermediate Similarity	NPC117346
0.8121	Intermediate Similarity	NPC240592
0.812	Intermediate Similarity	NPC476872
0.8116	Intermediate Similarity	NPC477294
0.8116	Intermediate Similarity	NPC214246

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 NPC70680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	736
0.2-0.3	1638
0.3-0.4	2694
0.4-0.5	2072
0.5-0.6	1152
0.6-0.7	555
0.7-0.8	68
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9338	High Similarity	NPD6190	Approved
0.8273	Intermediate Similarity	NPD230	Phase 1
0.803	Intermediate Similarity	NPD9545	Approved
0.7986	Intermediate Similarity	NPD7266	Discontinued
0.7945	Intermediate Similarity	NPD4628	Phase 3
0.7806	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7075	Discontinued
0.7746	Intermediate Similarity	NPD6233	Phase 2
0.7667	Intermediate Similarity	NPD6799	Approved
0.7651	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5402	Approved
0.7628	Intermediate Similarity	NPD3817	Phase 2
0.7613	Intermediate Similarity	NPD6801	Discontinued
0.7609	Intermediate Similarity	NPD9269	Phase 2
0.7597	Intermediate Similarity	NPD4380	Phase 2
0.758	Intermediate Similarity	NPD3882	Suspended
0.7576	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3764	Approved
0.7515	Intermediate Similarity	NPD7685	Pre-registration
0.7469	Intermediate Similarity	NPD6166	Phase 2
0.7469	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2801	Approved
0.7448	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD9268	Approved
0.7434	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6798	Discontinued
0.7421	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5403	Approved
0.7397	Intermediate Similarity	NPD6355	Discontinued
0.7396	Intermediate Similarity	NPD8150	Discontinued
0.7396	Intermediate Similarity	NPD8434	Phase 2
0.7389	Intermediate Similarity	NPD1934	Approved
0.7379	Intermediate Similarity	NPD4062	Phase 3
0.7378	Intermediate Similarity	NPD3818	Discontinued
0.7378	Intermediate Similarity	NPD3751	Discontinued
0.7372	Intermediate Similarity	NPD6599	Discontinued
0.7361	Intermediate Similarity	NPD3027	Phase 3
0.7355	Intermediate Similarity	NPD1653	Approved
0.7351	Intermediate Similarity	NPD8166	Discontinued
0.7349	Intermediate Similarity	NPD6797	Phase 2
0.7343	Intermediate Similarity	NPD9494	Approved
0.7342	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5844	Phase 1
0.7333	Intermediate Similarity	NPD2629	Approved
0.7328	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2935	Discontinued
0.7305	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7251	Discontinued
0.7285	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5401	Approved
0.7267	Intermediate Similarity	NPD6234	Discontinued
0.7262	Intermediate Similarity	NPD7808	Phase 3
0.725	Intermediate Similarity	NPD4965	Approved
0.725	Intermediate Similarity	NPD4966	Approved
0.725	Intermediate Similarity	NPD4967	Phase 2
0.7248	Intermediate Similarity	NPD7033	Discontinued
0.7239	Intermediate Similarity	NPD3787	Discontinued
0.7239	Intermediate Similarity	NPD6232	Discontinued
0.7229	Intermediate Similarity	NPD7054	Approved
0.7229	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1512	Approved
0.7219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD943	Approved
0.7197	Intermediate Similarity	NPD3455	Phase 2
0.7186	Intermediate Similarity	NPD7472	Approved
0.7186	Intermediate Similarity	NPD7074	Phase 3
0.7179	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1510	Phase 2
0.7133	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7819	Suspended
0.7125	Intermediate Similarity	NPD1465	Phase 2
0.7124	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7095	Approved
0.7113	Intermediate Similarity	NPD1608	Approved
0.7108	Intermediate Similarity	NPD7473	Discontinued
0.7107	Intermediate Similarity	NPD7411	Suspended
0.7107	Intermediate Similarity	NPD6386	Approved
0.7107	Intermediate Similarity	NPD6385	Approved
0.7105	Intermediate Similarity	NPD1549	Phase 2
0.7101	Intermediate Similarity	NPD9493	Approved
0.7097	Intermediate Similarity	NPD1511	Approved
0.7095	Intermediate Similarity	NPD1240	Approved
0.7095	Intermediate Similarity	NPD4060	Phase 1
0.7091	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD2067	Discontinued
0.7086	Intermediate Similarity	NPD1551	Phase 2
0.7081	Intermediate Similarity	NPD5353	Approved
0.7078	Intermediate Similarity	NPD3887	Approved
0.7078	Intermediate Similarity	NPD2354	Approved
0.7073	Intermediate Similarity	NPD7199	Phase 2
0.7068	Intermediate Similarity	NPD1358	Approved
0.7066	Intermediate Similarity	NPD7228	Approved
0.7051	Intermediate Similarity	NPD2532	Approved
0.7051	Intermediate Similarity	NPD2534	Approved
0.7051	Intermediate Similarity	NPD2533	Approved
0.7047	Intermediate Similarity	NPD447	Suspended
0.7047	Intermediate Similarity	NPD4340	Discontinued
0.7042	Intermediate Similarity	NPD1535	Discovery
0.7039	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3750	Approved
0.7013	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1607	Approved
0.7	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD6653	Approved
0.6993	Remote Similarity	NPD4534	Discontinued
0.6993	Remote Similarity	NPD1481	Phase 2
0.698	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1613	Approved
0.6974	Remote Similarity	NPD2796	Approved
0.697	Remote Similarity	NPD8127	Discontinued
0.6957	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7097	Phase 1
0.6949	Remote Similarity	NPD6534	Approved
0.6949	Remote Similarity	NPD6535	Approved
0.6948	Remote Similarity	NPD1652	Phase 2
0.6943	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5536	Phase 2
0.6923	Remote Similarity	NPD7435	Discontinued
0.6923	Remote Similarity	NPD422	Phase 1
0.6918	Remote Similarity	NPD5647	Approved
0.6918	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5048	Discontinued
0.6914	Remote Similarity	NPD8455	Phase 2
0.6914	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6663	Approved
0.6909	Remote Similarity	NPD5494	Approved
0.6906	Remote Similarity	NPD4198	Discontinued
0.6903	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4110	Phase 3
0.6901	Remote Similarity	NPD1778	Approved
0.6901	Remote Similarity	NPD17	Approved
0.6901	Remote Similarity	NPD8368	Discontinued
0.6897	Remote Similarity	NPD3225	Approved
0.6886	Remote Similarity	NPD5242	Approved
0.6883	Remote Similarity	NPD5958	Discontinued
0.6883	Remote Similarity	NPD2424	Discontinued
0.6879	Remote Similarity	NPD1894	Discontinued
0.6871	Remote Similarity	NPD5736	Approved
0.6871	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD826	Approved
0.6867	Remote Similarity	NPD825	Approved
0.6866	Remote Similarity	NPD3134	Approved
0.6863	Remote Similarity	NPD9570	Approved
0.6863	Remote Similarity	NPD2438	Suspended
0.6853	Remote Similarity	NPD3496	Discontinued
0.6851	Remote Similarity	NPD6780	Approved
0.6851	Remote Similarity	NPD6776	Approved
0.6851	Remote Similarity	NPD6782	Approved
0.6851	Remote Similarity	NPD6779	Approved
0.6851	Remote Similarity	NPD6777	Approved
0.6851	Remote Similarity	NPD6778	Approved
0.6851	Remote Similarity	NPD6781	Approved
0.6849	Remote Similarity	NPD2797	Approved
0.6849	Remote Similarity	NPD1203	Approved
0.6846	Remote Similarity	NPD3268	Approved
0.6846	Remote Similarity	NPD9495	Approved
0.6845	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3146	Approved
0.6833	Remote Similarity	NPD7700	Phase 2
0.6833	Remote Similarity	NPD7699	Phase 2
0.6829	Remote Similarity	NPD7768	Phase 2
0.6824	Remote Similarity	NPD6832	Phase 2
0.6821	Remote Similarity	NPD5124	Phase 1
0.6821	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6002	Phase 3
0.6818	Remote Similarity	NPD6005	Phase 3
0.6818	Remote Similarity	NPD5762	Approved
0.6818	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6004	Phase 3
0.6818	Remote Similarity	NPD2353	Approved
0.6818	Remote Similarity	NPD5763	Approved
0.6818	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7236	Approved
0.6806	Remote Similarity	NPD1091	Approved
0.6797	Remote Similarity	NPD2799	Discontinued
0.6795	Remote Similarity	NPD3400	Discontinued
0.6793	Remote Similarity	NPD8320	Phase 1
0.6793	Remote Similarity	NPD8319	Approved
0.679	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3749	Approved
0.6782	Remote Similarity	NPD8407	Phase 2
0.6772	Remote Similarity	NPD4357	Discontinued
0.677	Remote Similarity	NPD7458	Discontinued
0.677	Remote Similarity	NPD3226	Approved
0.6763	Remote Similarity	NPD1241	Discontinued
0.6759	Remote Similarity	NPD9717	Approved
0.6753	Remote Similarity	NPD6100	Approved
0.6753	Remote Similarity	NPD6099	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