NPASS Compound

Structure

NPC192568 OpenBabel07101718182D 39 41 0 0 1 0 0 0 0 0999 V2000 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 3.3301 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 -2.7321 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 3.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 -2.7321 2.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.1962 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 -2.7321 4.1962 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 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 1 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 -3.2321 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 -2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2321 5.0622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 5.0622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 -4.2321 -0.1340 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 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 -2.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 37 1 0 0 0 0 2 5 2 0 0 0 0 2 13 1 0 0 0 0 3 7 2 0 0 0 0 3 13 1 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 22 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 23 1 0 0 0 0 11 19 1 0 0 0 0 11 26 1 0 0 0 0 12 21 1 0 0 0 0 12 26 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 24 1 0 0 0 0 19 31 1 6 0 0 0 20 10 1 6 0 0 0 20 37 1 0 0 0 0 21 24 1 0 0 0 0 21 38 1 1 0 0 0 22 32 2 0 0 0 0 22 39 1 0 0 0 0 23 33 2 0 0 0 0 23 38 1 0 0 0 0 24 34 1 6 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 26 25 1 1 0 0 0 26 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.15
Volume:	520.491
LogP:	1.003
LogD:	0.085
LogS:	-1.795
# Rotatable Bonds:	11
TPSA:	220.51
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.133
Synthetic Accessibility Score:	4.424
Fsp3:	0.346
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.436
MDCK Permeability:	3.169532283209264e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.441
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	92.13292694091797%
Volume Distribution (VD):	0.44
Pgp-substrate:	11.120035171508789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.164
CYP2C9-substrate:	0.252
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.395
CYP3A4-substrate:	0.036

ADMET: Excretion

Clearance (CL):	4.803
Half-life (T1/2):	0.937

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.524
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.706
Skin Sensitization:	0.919
Carcinogencity:	0.278
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.067

Download Data

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

Natural Product: NPC192568

Natural Product ID:	NPC192568
*Common Name:**	1-O-Trans-Caffeoyl-5-O-7,8-Dihydro-7Alpha-Methoxycaffeoylquinic Acid
IUPAC Name:	(1S,3R,4R,5R)-3-[(3S)-3-(3,4-dihydroxyphenyl)-3-methoxypropanoyl]oxy-1-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexane-1-carboxylic acid
Synonyms:
Standard InCHIKey:	LJQOTSZZGZIZEG-OQJUOGDSSA-N
Standard InCHI:	InChI=1S/C26H28O13/c1-37-20(14-4-6-16(28)18(30)9-14)10-23(33)38-21-12-26(25(35)36,11-19(31)24(21)34)39-22(32)7-3-13-2-5-15(27)17(29)8-13/h2-9,19-21,24,27-31,34H,10-12H2,1H3,(H,35,36)/b7-3+/t19-,20+,21-,24-,26+/m1/s1
SMILES:	CO[C@H](c1ccc(c(c1)O)O)CC(=O)O[C@@H]1C[C@@](OC(=O)/C=C/c2ccc(c(c2)O)O)(C[C@H]([C@H]1O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2349422
PubChem CID:	71719001
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	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	174890.0	nM	PMID[458330]
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	93.2	%	PMID[458330]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	4660.0	nM	PMID[458330]

☑ 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 NPC192568 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	323
0.1-0.2	1271
0.2-0.3	3064
0.3-0.4	6836
0.4-0.5	10168
0.5-0.6	6093
0.6-0.7	7109
0.7-0.8	7241
0.8-0.85	461
0.85-0.9	70
0.9-0.95	37
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471076
0.9643	High Similarity	NPC472016
0.9643	High Similarity	NPC220664
0.9643	High Similarity	NPC192831
0.9643	High Similarity	NPC277315
0.9643	High Similarity	NPC37331
0.9643	High Similarity	NPC284948
0.9643	High Similarity	NPC258469
0.9643	High Similarity	NPC303090
0.9643	High Similarity	NPC319628
0.9643	High Similarity	NPC43158
0.9571	High Similarity	NPC35702
0.9571	High Similarity	NPC224389
0.9571	High Similarity	NPC477335
0.9571	High Similarity	NPC297517
0.9571	High Similarity	NPC13818
0.9571	High Similarity	NPC471027
0.9571	High Similarity	NPC206095
0.951	High Similarity	NPC322660
0.9429	High Similarity	NPC26241
0.9429	High Similarity	NPC274891
0.9429	High Similarity	NPC303683
0.9429	High Similarity	NPC476819
0.9429	High Similarity	NPC205751
0.9429	High Similarity	NPC295492
0.9429	High Similarity	NPC474875
0.9429	High Similarity	NPC476820
0.9357	High Similarity	NPC24295
0.9357	High Similarity	NPC302857
0.9357	High Similarity	NPC283560
0.9357	High Similarity	NPC152942
0.9357	High Similarity	NPC37250
0.9357	High Similarity	NPC278068
0.9357	High Similarity	NPC142703
0.9357	High Similarity	NPC219428
0.9315	High Similarity	NPC306343
0.9247	High Similarity	NPC42464
0.9241	High Similarity	NPC229264
0.9236	High Similarity	NPC477333
0.92	High Similarity	NPC473275
0.92	High Similarity	NPC470896
0.9189	High Similarity	NPC93498
0.9189	High Similarity	NPC163883
0.9178	High Similarity	NPC43123
0.9172	High Similarity	NPC98356
0.9155	High Similarity	NPC156709
0.9155	High Similarity	NPC179505
0.9143	High Similarity	NPC182217
0.9143	High Similarity	NPC70680
0.9143	High Similarity	NPC233350
0.9128	High Similarity	NPC146277
0.9128	High Similarity	NPC19380
0.9071	High Similarity	NPC68517
0.9071	High Similarity	NPC106406
0.9014	High Similarity	NPC279676
0.9014	High Similarity	NPC67349
0.9007	High Similarity	NPC145425
0.9	High Similarity	NPC155209
0.9	High Similarity	NPC168799
0.8993	High Similarity	NPC477334
0.898	High Similarity	NPC221383
0.898	High Similarity	NPC143892
0.898	High Similarity	NPC283081
0.898	High Similarity	NPC299090
0.8933	High Similarity	NPC95498
0.8933	High Similarity	NPC246566
0.8929	High Similarity	NPC61
0.8929	High Similarity	NPC25581
0.8929	High Similarity	NPC5419
0.8929	High Similarity	NPC18074
0.8926	High Similarity	NPC32197
0.8904	High Similarity	NPC114242
0.8904	High Similarity	NPC50221
0.8874	High Similarity	NPC44730
0.8867	High Similarity	NPC252979
0.8867	High Similarity	NPC300329
0.8857	High Similarity	NPC198388
0.8844	High Similarity	NPC53884
0.8844	High Similarity	NPC258671
0.8803	High Similarity	NPC474895
0.88	High Similarity	NPC259576
0.88	High Similarity	NPC221091
0.8776	High Similarity	NPC226738
0.8776	High Similarity	NPC121573
0.8776	High Similarity	NPC190587
0.8776	High Similarity	NPC22176
0.8776	High Similarity	NPC304956
0.8767	High Similarity	NPC477277
0.8767	High Similarity	NPC477278
0.8759	High Similarity	NPC288452
0.8759	High Similarity	NPC289690
0.8701	High Similarity	NPC134925
0.8699	High Similarity	NPC38473
0.8699	High Similarity	NPC477279
0.8693	High Similarity	NPC477299
0.8684	High Similarity	NPC106818
0.8667	High Similarity	NPC472969
0.8667	High Similarity	NPC142528
0.8654	High Similarity	NPC44507
0.8652	High Similarity	NPC217052
0.8652	High Similarity	NPC329344
0.8652	High Similarity	NPC32626
0.8652	High Similarity	NPC237506
0.8649	High Similarity	NPC470130
0.8649	High Similarity	NPC474692
0.8649	High Similarity	NPC160378
0.8649	High Similarity	NPC183824
0.8645	High Similarity	NPC40920
0.8645	High Similarity	NPC223335
0.8636	High Similarity	NPC203757
0.8627	High Similarity	NPC327225
0.8627	High Similarity	NPC87403
0.8618	High Similarity	NPC140151
0.8616	High Similarity	NPC471823
0.8609	High Similarity	NPC476394
0.8609	High Similarity	NPC98809
0.8608	High Similarity	NPC272750
0.8608	High Similarity	NPC134047
0.8608	High Similarity	NPC223006
0.8608	High Similarity	NPC173729
0.8592	High Similarity	NPC108553
0.8592	High Similarity	NPC318799
0.859	High Similarity	NPC469654
0.8581	High Similarity	NPC285550
0.8562	High Similarity	NPC75695
0.8562	High Similarity	NPC128403
0.8544	High Similarity	NPC144557
0.8543	High Similarity	NPC248257
0.8543	High Similarity	NPC120621
0.8543	High Similarity	NPC98009
0.8503	High Similarity	NPC225036
0.8503	High Similarity	NPC12218
0.8503	High Similarity	NPC105525
0.8503	High Similarity	NPC75763
0.85	High Similarity	NPC475695
0.8497	Intermediate Similarity	NPC243891
0.8491	Intermediate Similarity	NPC227297
0.8487	Intermediate Similarity	NPC92117
0.8487	Intermediate Similarity	NPC75945
0.8481	Intermediate Similarity	NPC112418
0.8472	Intermediate Similarity	NPC471749
0.8466	Intermediate Similarity	NPC476374
0.8452	Intermediate Similarity	NPC125487
0.8452	Intermediate Similarity	NPC281703
0.8446	Intermediate Similarity	NPC9218
0.8442	Intermediate Similarity	NPC227485
0.8442	Intermediate Similarity	NPC476434
0.8442	Intermediate Similarity	NPC267091
0.8438	Intermediate Similarity	NPC471788
0.8435	Intermediate Similarity	NPC239943
0.8435	Intermediate Similarity	NPC284409
0.8431	Intermediate Similarity	NPC473091
0.8428	Intermediate Similarity	NPC471745
0.8425	Intermediate Similarity	NPC156892
0.8421	Intermediate Similarity	NPC28776
0.8421	Intermediate Similarity	NPC473138
0.8421	Intermediate Similarity	NPC1580
0.8418	Intermediate Similarity	NPC471744
0.8414	Intermediate Similarity	NPC135127
0.8411	Intermediate Similarity	NPC473867
0.8408	Intermediate Similarity	NPC472860
0.8408	Intermediate Similarity	NPC226759
0.8405	Intermediate Similarity	NPC476370
0.84	Intermediate Similarity	NPC473090
0.8395	Intermediate Similarity	NPC280493
0.8387	Intermediate Similarity	NPC61152
0.8387	Intermediate Similarity	NPC3746
0.8387	Intermediate Similarity	NPC16024
0.8387	Intermediate Similarity	NPC205037
0.8387	Intermediate Similarity	NPC44260
0.8378	Intermediate Similarity	NPC474784
0.8369	Intermediate Similarity	NPC168653
0.8369	Intermediate Similarity	NPC251407
0.8367	Intermediate Similarity	NPC308976
0.8367	Intermediate Similarity	NPC302583
0.8367	Intermediate Similarity	NPC100558
0.8367	Intermediate Similarity	NPC84789
0.8367	Intermediate Similarity	NPC310252
0.8366	Intermediate Similarity	NPC478242
0.8356	Intermediate Similarity	NPC18646
0.8344	Intermediate Similarity	NPC475058
0.8344	Intermediate Similarity	NPC471405
0.8333	Intermediate Similarity	NPC469888
0.8333	Intermediate Similarity	NPC194095
0.8333	Intermediate Similarity	NPC283041
0.8333	Intermediate Similarity	NPC327032
0.8333	Intermediate Similarity	NPC191046
0.8322	Intermediate Similarity	NPC226855
0.8322	Intermediate Similarity	NPC94810
0.8313	Intermediate Similarity	NPC35167
0.8311	Intermediate Similarity	NPC220942
0.8302	Intermediate Similarity	NPC301089
0.8302	Intermediate Similarity	NPC24164
0.8302	Intermediate Similarity	NPC239966
0.8302	Intermediate Similarity	NPC203020
0.8302	Intermediate Similarity	NPC476373
0.8302	Intermediate Similarity	NPC53889
0.8298	Intermediate Similarity	NPC132921
0.8293	Intermediate Similarity	NPC190003
0.8293	Intermediate Similarity	NPC175107

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 NPC192568 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	789
0.2-0.3	1660
0.3-0.4	2665
0.4-0.5	2043
0.5-0.6	1110
0.6-0.7	491
0.7-0.8	115
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9643	High Similarity	NPD6190	Approved
0.8228	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD230	Phase 1
0.8193	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD7266	Discontinued
0.8165	Intermediate Similarity	NPD3817	Phase 2
0.8113	Intermediate Similarity	NPD3882	Suspended
0.8098	Intermediate Similarity	NPD6166	Phase 2
0.8098	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2801	Approved
0.7964	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6797	Phase 2
0.795	Intermediate Similarity	NPD7075	Discontinued
0.7937	Intermediate Similarity	NPD5402	Approved
0.7925	Intermediate Similarity	NPD1934	Approved
0.7917	Intermediate Similarity	NPD7251	Discontinued
0.7892	Intermediate Similarity	NPD3818	Discontinued
0.7875	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6233	Phase 2
0.7812	Intermediate Similarity	NPD6801	Discontinued
0.7784	Intermediate Similarity	NPD3751	Discontinued
0.7771	Intermediate Similarity	NPD1512	Approved
0.7765	Intermediate Similarity	NPD7808	Phase 3
0.7764	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6232	Discontinued
0.7756	Intermediate Similarity	NPD6799	Approved
0.7756	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7054	Approved
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7685	Pre-registration
0.7692	Intermediate Similarity	NPD7472	Approved
0.7692	Intermediate Similarity	NPD7074	Phase 3
0.7688	Intermediate Similarity	NPD8150	Discontinued
0.7688	Intermediate Similarity	NPD4380	Phase 2
0.7683	Intermediate Similarity	NPD6234	Discontinued
0.7677	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD3787	Discontinued
0.7643	Intermediate Similarity	NPD1511	Approved
0.7633	Intermediate Similarity	NPD5844	Phase 1
0.7619	Intermediate Similarity	NPD7473	Discontinued
0.761	Intermediate Similarity	NPD5403	Approved
0.7593	Intermediate Similarity	NPD37	Approved
0.7584	Intermediate Similarity	NPD3027	Phase 3
0.7564	Intermediate Similarity	NPD8166	Discontinued
0.7561	Intermediate Similarity	NPD4966	Approved
0.7561	Intermediate Similarity	NPD4965	Approved
0.7561	Intermediate Similarity	NPD4967	Phase 2
0.755	Intermediate Similarity	NPD943	Approved
0.7533	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD6798	Discontinued
0.7515	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7484	Intermediate Similarity	NPD5401	Approved
0.7483	Intermediate Similarity	NPD9545	Approved
0.7471	Intermediate Similarity	NPD7228	Approved
0.7469	Intermediate Similarity	NPD6599	Discontinued
0.7466	Intermediate Similarity	NPD9269	Phase 2
0.7453	Intermediate Similarity	NPD1653	Approved
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7427	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2935	Discontinued
0.7415	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3455	Phase 2
0.7381	Intermediate Similarity	NPD7199	Phase 2
0.7375	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7033	Discontinued
0.7351	Intermediate Similarity	NPD7095	Approved
0.7333	Intermediate Similarity	NPD9494	Approved
0.7333	Intermediate Similarity	NPD7819	Suspended
0.7321	Intermediate Similarity	NPD5494	Approved
0.732	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1613	Approved
0.7317	Intermediate Similarity	NPD7411	Suspended
0.7303	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7255	Intermediate Similarity	NPD4062	Phase 3
0.7244	Intermediate Similarity	NPD1510	Phase 2
0.7238	Intermediate Similarity	NPD6535	Approved
0.7238	Intermediate Similarity	NPD6534	Approved
0.7215	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1549	Phase 2
0.7212	Intermediate Similarity	NPD6386	Approved
0.7212	Intermediate Similarity	NPD6385	Approved
0.72	Intermediate Similarity	NPD6559	Discontinued
0.7192	Intermediate Similarity	NPD9268	Approved
0.7176	Intermediate Similarity	NPD8127	Discontinued
0.7166	Intermediate Similarity	NPD8320	Phase 1
0.7166	Intermediate Similarity	NPD8319	Approved
0.7161	Intermediate Similarity	NPD447	Suspended
0.716	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD919	Approved
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6777	Approved
0.7135	Intermediate Similarity	NPD6779	Approved
0.7135	Intermediate Similarity	NPD6776	Approved
0.7135	Intermediate Similarity	NPD6781	Approved
0.7135	Intermediate Similarity	NPD6778	Approved
0.7135	Intermediate Similarity	NPD6780	Approved
0.7135	Intermediate Similarity	NPD6782	Approved
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7097	Intermediate Similarity	NPD1240	Approved
0.7097	Intermediate Similarity	NPD4060	Phase 1
0.7091	Intermediate Similarity	NPD3226	Approved
0.7089	Intermediate Similarity	NPD9570	Approved
0.7089	Intermediate Similarity	NPD2796	Approved
0.7083	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1247	Approved
0.7068	Intermediate Similarity	NPD7874	Approved
0.7068	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2532	Approved
0.7055	Intermediate Similarity	NPD2534	Approved
0.7055	Intermediate Similarity	NPD2533	Approved
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4340	Discontinued
0.7041	Intermediate Similarity	NPD7768	Phase 2
0.7022	Intermediate Similarity	NPD8313	Approved
0.7022	Intermediate Similarity	NPD8312	Approved
0.7019	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7039	Approved
0.7006	Intermediate Similarity	NPD7240	Approved
0.7006	Intermediate Similarity	NPD1607	Approved
0.7006	Intermediate Similarity	NPD7038	Approved
0.7006	Intermediate Similarity	NPD8368	Discontinued
0.7	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD3749	Approved
0.6994	Remote Similarity	NPD5242	Approved
0.6994	Remote Similarity	NPD3926	Phase 2
0.6993	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5353	Approved
0.6981	Remote Similarity	NPD1551	Phase 2
0.6977	Remote Similarity	NPD6959	Discontinued
0.6975	Remote Similarity	NPD3887	Approved
0.6975	Remote Similarity	NPD2354	Approved
0.6973	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3146	Approved
0.6951	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5536	Phase 2
0.6931	Remote Similarity	NPD7697	Approved
0.6931	Remote Similarity	NPD7698	Approved
0.6931	Remote Similarity	NPD7696	Phase 3
0.6923	Remote Similarity	NPD8435	Approved
0.6923	Remote Similarity	NPD8455	Phase 2
0.6923	Remote Similarity	NPD8361	Approved
0.6923	Remote Similarity	NPD8360	Approved
0.6918	Remote Similarity	NPD4198	Discontinued
0.6918	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3750	Approved
0.6914	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4110	Phase 3
0.6895	Remote Similarity	NPD7870	Phase 2
0.6895	Remote Similarity	NPD7871	Phase 2
0.6894	Remote Similarity	NPD4534	Discontinued
0.6889	Remote Similarity	NPD8407	Phase 2
0.6879	Remote Similarity	NPD825	Approved
0.6879	Remote Similarity	NPD826	Approved
0.6875	Remote Similarity	NPD7701	Phase 2
0.6875	Remote Similarity	NPD5404	Approved
0.6875	Remote Similarity	NPD5406	Approved
0.6875	Remote Similarity	NPD5408	Approved
0.6875	Remote Similarity	NPD5405	Approved
0.6871	Remote Similarity	NPD9493	Approved
0.6855	Remote Similarity	NPD7097	Phase 1
0.6853	Remote Similarity	NPD3021	Approved
0.6853	Remote Similarity	NPD3022	Approved
0.6849	Remote Similarity	NPD2629	Approved
0.6839	Remote Similarity	NPD6832	Phase 2
0.6835	Remote Similarity	NPD1933	Approved
0.6829	Remote Similarity	NPD7236	Approved
0.6821	Remote Similarity	NPD1535	Discovery
0.6818	Remote Similarity	NPD5647	Approved
0.6815	Remote Similarity	NPD6663	Approved
0.6813	Remote Similarity	NPD2799	Discontinued
0.6809	Remote Similarity	NPD5048	Discontinued
0.6807	Remote Similarity	NPD6273	Approved
0.68	Remote Similarity	NPD17	Approved
0.6796	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6653	Approved
0.6791	Remote Similarity	NPD8485	Approved
0.679	Remote Similarity	NPD5958	Discontinued
0.6788	Remote Similarity	NPD4357	Discontinued
0.6788	Remote Similarity	NPD7390	Discontinued
0.6786	Remote Similarity	NPD7458	Discontinued
0.678	Remote Similarity	NPD7799	Discontinued
0.6776	Remote Similarity	NPD1481	Phase 2
0.6774	Remote Similarity	NPD5736	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