NPASS Compound

Structure

CID168653 OpenBabel06191715542D 22 22 0 0 1 0 0 0 0 0999 V2000 1.7321 1.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -0.0000 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 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 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 7.7942 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 6 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.05
Volume:	285.505
LogP:	-0.368
LogD:	-0.307
LogS:	-1.093
# Rotatable Bonds:	7
TPSA:	161.59
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.146
Synthetic Accessibility Score:	3.248
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.201
MDCK Permeability:	0.0002583330497145653
Pgp-inhibitor:	0.0
Pgp-substrate:	0.152
Human Intestinal Absorption (HIA):	0.86
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.462
Plasma Protein Binding (PPB):	79.98907470703125%
Volume Distribution (VD):	0.28
Pgp-substrate:	24.264009475708008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.561
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	3.007
Half-life (T1/2):	0.963

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.862
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.322
Carcinogencity:	0.065
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC168653

Natural Product ID:	NPC168653
*Common Name:**	Caffeoyltartaric Acid
IUPAC Name:	2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxybutanedioic acid
Synonyms:	Caffeoyltartaric Acid
Standard InCHIKey:	SWGKAHCIOQPKFW-DUXPYHPUSA-N
Standard InCHI:	InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+
SMILES:	O=C(OC(C(C(=O)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499757
PubChem CID:	9857913
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
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25590529]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO14022	Salvia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20285	Monarda didyma	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16931	Cichorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14022	Salvia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20285	Monarda didyma	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	3

Activity Type	# Activity
NON-MOLECULAR	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	873000.0	nM	PMID[517749]
NPT2	Others	Unspecified		IC50	=	433000.0	nM	PMID[517749]
NPT2	Others	Unspecified		Activity	=	55.0	%	PMID[517749]
NPT2	Others	Unspecified		Activity	=	57.9	%	PMID[517749]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	125.3	uM/L	PMID[517750]

☑ 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 NPC168653 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	313
0.1-0.2	1344
0.2-0.3	4604
0.3-0.4	10050
0.4-0.5	8402
0.5-0.6	6465
0.6-0.7	9792
0.7-0.8	1560
0.8-0.85	132
0.85-0.9	23
0.9-0.95	3
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC251407
0.9916	High Similarity	NPC132921
0.9669	High Similarity	NPC475695
0.9516	High Similarity	NPC32626
0.9516	High Similarity	NPC237506
0.9516	High Similarity	NPC217052
0.9516	High Similarity	NPC329344
0.935	High Similarity	NPC147192
0.907	High Similarity	NPC474895
0.9008	High Similarity	NPC279676
0.9008	High Similarity	NPC67349
0.8908	High Similarity	NPC217472
0.8872	High Similarity	NPC156709
0.8872	High Similarity	NPC179505
0.8689	High Similarity	NPC65791
0.8678	High Similarity	NPC233669
0.8667	High Similarity	NPC95381
0.8651	High Similarity	NPC224208
0.8651	High Similarity	NPC474275
0.8647	High Similarity	NPC470572
0.8607	High Similarity	NPC281277
0.8595	High Similarity	NPC328593
0.8595	High Similarity	NPC261453
0.8595	High Similarity	NPC33749
0.8594	High Similarity	NPC118584
0.8551	High Similarity	NPC53884
0.8551	High Similarity	NPC258671
0.855	High Similarity	NPC108553
0.8548	High Similarity	NPC241634
0.8527	High Similarity	NPC476873
0.8525	High Similarity	NPC474967
0.8519	High Similarity	NPC278068
0.8519	High Similarity	NPC152942
0.8519	High Similarity	NPC220942
0.8519	High Similarity	NPC142703
0.8519	High Similarity	NPC219428
0.8519	High Similarity	NPC37250
0.8519	High Similarity	NPC302857
0.8516	High Similarity	NPC67951
0.8504	High Similarity	NPC285345
0.85	High Similarity	NPC226250
0.8485	Intermediate Similarity	NPC18074
0.8485	Intermediate Similarity	NPC25581
0.8485	Intermediate Similarity	NPC61
0.8485	Intermediate Similarity	NPC5419
0.8478	Intermediate Similarity	NPC304956
0.8468	Intermediate Similarity	NPC309434
0.8462	Intermediate Similarity	NPC232880
0.8456	Intermediate Similarity	NPC303683
0.8456	Intermediate Similarity	NPC26241
0.8456	Intermediate Similarity	NPC274891
0.8456	Intermediate Similarity	NPC295492
0.8456	Intermediate Similarity	NPC476820
0.8456	Intermediate Similarity	NPC474875
0.8456	Intermediate Similarity	NPC476819
0.8456	Intermediate Similarity	NPC205751
0.8429	Intermediate Similarity	NPC283081
0.8429	Intermediate Similarity	NPC299090
0.8429	Intermediate Similarity	NPC229264
0.8429	Intermediate Similarity	NPC221383
0.8429	Intermediate Similarity	NPC143892
0.8421	Intermediate Similarity	NPC155209
0.8421	Intermediate Similarity	NPC168799
0.8409	Intermediate Similarity	NPC198388
0.8406	Intermediate Similarity	NPC319628
0.8406	Intermediate Similarity	NPC303090
0.8406	Intermediate Similarity	NPC37331
0.8406	Intermediate Similarity	NPC284948
0.8406	Intermediate Similarity	NPC220664
0.8397	Intermediate Similarity	NPC477293
0.8397	Intermediate Similarity	NPC477294
0.8397	Intermediate Similarity	NPC229784
0.8369	Intermediate Similarity	NPC192568
0.8369	Intermediate Similarity	NPC471076
0.8358	Intermediate Similarity	NPC106406
0.8333	Intermediate Similarity	NPC202474
0.8333	Intermediate Similarity	NPC477335
0.8333	Intermediate Similarity	NPC471027
0.8333	Intermediate Similarity	NPC13818
0.8333	Intermediate Similarity	NPC206095
0.8333	Intermediate Similarity	NPC35702
0.8333	Intermediate Similarity	NPC224389
0.8333	Intermediate Similarity	NPC297517
0.832	Intermediate Similarity	NPC275519
0.832	Intermediate Similarity	NPC203124
0.8298	Intermediate Similarity	NPC322660
0.8279	Intermediate Similarity	NPC131530
0.8273	Intermediate Similarity	NPC472016
0.8273	Intermediate Similarity	NPC192831
0.8273	Intermediate Similarity	NPC258469
0.8273	Intermediate Similarity	NPC43158
0.8273	Intermediate Similarity	NPC277315
0.8271	Intermediate Similarity	NPC219677
0.8268	Intermediate Similarity	NPC470848
0.8268	Intermediate Similarity	NPC470849
0.8268	Intermediate Similarity	NPC204466
0.8254	Intermediate Similarity	NPC141791
0.8254	Intermediate Similarity	NPC263386
0.8235	Intermediate Similarity	NPC1786
0.8235	Intermediate Similarity	NPC294902
0.8235	Intermediate Similarity	NPC1075
0.8231	Intermediate Similarity	NPC197832
0.8222	Intermediate Similarity	NPC68517
0.8217	Intermediate Similarity	NPC306100
0.8214	Intermediate Similarity	NPC474692
0.8209	Intermediate Similarity	NPC473924
0.8209	Intermediate Similarity	NPC473285
0.8203	Intermediate Similarity	NPC70752
0.8201	Intermediate Similarity	NPC477277
0.8201	Intermediate Similarity	NPC477278
0.8188	Intermediate Similarity	NPC471875
0.8182	Intermediate Similarity	NPC110313
0.8175	Intermediate Similarity	NPC70744
0.8175	Intermediate Similarity	NPC63126
0.8175	Intermediate Similarity	NPC272471
0.8175	Intermediate Similarity	NPC137537
0.8175	Intermediate Similarity	NPC164706
0.8175	Intermediate Similarity	NPC104514
0.8175	Intermediate Similarity	NPC107588
0.8162	Intermediate Similarity	NPC182217
0.8162	Intermediate Similarity	NPC233350
0.8162	Intermediate Similarity	NPC70680
0.8148	Intermediate Similarity	NPC475468
0.8148	Intermediate Similarity	NPC254398
0.8138	Intermediate Similarity	NPC95498
0.8138	Intermediate Similarity	NPC246566
0.8134	Intermediate Similarity	NPC318799
0.8129	Intermediate Similarity	NPC477279
0.8125	Intermediate Similarity	NPC32197
0.812	Intermediate Similarity	NPC226855
0.8116	Intermediate Similarity	NPC239943
0.8116	Intermediate Similarity	NPC283560
0.8116	Intermediate Similarity	NPC24295
0.8099	Intermediate Similarity	NPC98356
0.8088	Intermediate Similarity	NPC135127
0.8088	Intermediate Similarity	NPC34293
0.8088	Intermediate Similarity	NPC886
0.8088	Intermediate Similarity	NPC471883
0.8088	Intermediate Similarity	NPC471110
0.8088	Intermediate Similarity	NPC287597
0.8085	Intermediate Similarity	NPC50221
0.8085	Intermediate Similarity	NPC114242
0.8062	Intermediate Similarity	NPC147654
0.8058	Intermediate Similarity	NPC289690
0.8058	Intermediate Similarity	NPC105525
0.8058	Intermediate Similarity	NPC75763
0.8058	Intermediate Similarity	NPC12218
0.8058	Intermediate Similarity	NPC225036
0.8058	Intermediate Similarity	NPC288452
0.8047	Intermediate Similarity	NPC2058
0.8029	Intermediate Similarity	NPC470990
0.8029	Intermediate Similarity	NPC476870
0.8028	Intermediate Similarity	NPC477333
0.8015	Intermediate Similarity	NPC60517
0.8015	Intermediate Similarity	NPC20443
0.8015	Intermediate Similarity	NPC288945
0.8015	Intermediate Similarity	NPC157478
0.8015	Intermediate Similarity	NPC246704
0.8015	Intermediate Similarity	NPC295406
0.8015	Intermediate Similarity	NPC200422
0.8015	Intermediate Similarity	NPC146886
0.8015	Intermediate Similarity	NPC289572
0.8015	Intermediate Similarity	NPC471749
0.8	Intermediate Similarity	NPC38473
0.8	Intermediate Similarity	NPC259576
0.8	Intermediate Similarity	NPC221091
0.8	Intermediate Similarity	NPC281798
0.7985	Intermediate Similarity	NPC477300
0.7985	Intermediate Similarity	NPC48315
0.7984	Intermediate Similarity	NPC476872
0.7971	Intermediate Similarity	NPC186418
0.7971	Intermediate Similarity	NPC157554
0.797	Intermediate Similarity	NPC158654
0.7969	Intermediate Similarity	NPC470214
0.7969	Intermediate Similarity	NPC109371
0.7969	Intermediate Similarity	NPC470215
0.7969	Intermediate Similarity	NPC70084
0.7958	Intermediate Similarity	NPC183824
0.7955	Intermediate Similarity	NPC289459
0.7945	Intermediate Similarity	NPC300329
0.7939	Intermediate Similarity	NPC212541
0.7934	Intermediate Similarity	NPC19149
0.7931	Intermediate Similarity	NPC42464
0.7923	Intermediate Similarity	NPC322332
0.7923	Intermediate Similarity	NPC11724
0.792	Intermediate Similarity	NPC148969
0.792	Intermediate Similarity	NPC264558
0.7914	Intermediate Similarity	NPC476376
0.7914	Intermediate Similarity	NPC78363
0.7914	Intermediate Similarity	NPC260425
0.791	Intermediate Similarity	NPC109275
0.7905	Intermediate Similarity	NPC477299
0.7899	Intermediate Similarity	NPC176102
0.7899	Intermediate Similarity	NPC254832
0.7899	Intermediate Similarity	NPC229638
0.7899	Intermediate Similarity	NPC267539
0.7899	Intermediate Similarity	NPC29317
0.7899	Intermediate Similarity	NPC71108
0.7899	Intermediate Similarity	NPC311742
0.7899	Intermediate Similarity	NPC204257

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 NPC168653 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	808
0.2-0.3	2000
0.3-0.4	2902
0.4-0.5	1707
0.5-0.6	1085
0.6-0.7	357
0.7-0.8	29
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8406	Intermediate Similarity	NPD6190	Approved
0.7883	Intermediate Similarity	NPD230	Phase 1
0.7857	Intermediate Similarity	NPD7266	Discontinued
0.7669	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD447	Suspended
0.7463	Intermediate Similarity	NPD9269	Phase 2
0.7344	Intermediate Similarity	NPD228	Approved
0.7333	Intermediate Similarity	NPD1653	Approved
0.7302	Intermediate Similarity	NPD1358	Approved
0.7292	Intermediate Similarity	NPD9570	Approved
0.7222	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9545	Approved
0.7211	Intermediate Similarity	NPD8166	Discontinued
0.7197	Intermediate Similarity	NPD9493	Approved
0.7164	Intermediate Similarity	NPD9268	Approved
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7134	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3882	Suspended
0.7113	Intermediate Similarity	NPD6233	Phase 2
0.7092	Intermediate Similarity	NPD3027	Phase 3
0.7077	Intermediate Similarity	NPD969	Suspended
0.7063	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7063	Intermediate Similarity	NPD943	Approved
0.7063	Intermediate Similarity	NPD1613	Approved
0.7063	Intermediate Similarity	NPD825	Approved
0.7063	Intermediate Similarity	NPD826	Approved
0.7059	Intermediate Similarity	NPD3455	Phase 2
0.7051	Intermediate Similarity	NPD5402	Approved
0.7051	Intermediate Similarity	NPD3817	Phase 2
0.7037	Intermediate Similarity	NPD1357	Approved
0.7014	Intermediate Similarity	NPD555	Phase 2
0.6974	Remote Similarity	NPD1512	Approved
0.6972	Remote Similarity	NPD7095	Approved
0.6966	Remote Similarity	NPD6653	Approved
0.6953	Remote Similarity	NPD3134	Approved
0.6939	Remote Similarity	NPD2935	Discontinued
0.6933	Remote Similarity	NPD3818	Discontinued
0.6923	Remote Similarity	NPD1934	Approved
0.6923	Remote Similarity	NPD3021	Approved
0.6923	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD3022	Approved
0.6914	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6166	Phase 2
0.6909	Remote Similarity	NPD6797	Phase 2
0.6909	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6355	Discontinued
0.6879	Remote Similarity	NPD257	Approved
0.6879	Remote Similarity	NPD258	Approved
0.6879	Remote Similarity	NPD5647	Approved
0.6875	Remote Similarity	NPD4062	Phase 3
0.6875	Remote Similarity	NPD259	Phase 1
0.6867	Remote Similarity	NPD7251	Discontinued
0.6861	Remote Similarity	NPD9381	Approved
0.6861	Remote Similarity	NPD9384	Approved
0.6855	Remote Similarity	NPD7075	Discontinued
0.6846	Remote Similarity	NPD9266	Approved
0.6846	Remote Similarity	NPD74	Approved
0.6842	Remote Similarity	NPD1511	Approved
0.6835	Remote Similarity	NPD9717	Approved
0.6831	Remote Similarity	NPD9569	Approved
0.6818	Remote Similarity	NPD5403	Approved
0.6812	Remote Similarity	NPD3496	Discontinued
0.6809	Remote Similarity	NPD1203	Approved
0.68	Remote Similarity	NPD9495	Approved
0.6797	Remote Similarity	NPD5401	Approved
0.6794	Remote Similarity	NPD2067	Discontinued
0.6791	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2801	Approved
0.6769	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD290	Approved
0.6769	Remote Similarity	NPD9267	Approved
0.6769	Remote Similarity	NPD9264	Approved
0.6769	Remote Similarity	NPD9263	Approved
0.6766	Remote Similarity	NPD7685	Pre-registration
0.6755	Remote Similarity	NPD4628	Phase 3
0.6742	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6799	Approved
0.6727	Remote Similarity	NPD3751	Discontinued
0.6726	Remote Similarity	NPD7808	Phase 3
0.6713	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6801	Discontinued
0.6708	Remote Similarity	NPD6234	Discontinued
0.6706	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD405	Clinical (unspecified phase)
0.669	Remote Similarity	NPD411	Approved
0.669	Remote Similarity	NPD987	Approved
0.669	Remote Similarity	NPD3764	Approved
0.6689	Remote Similarity	NPD7097	Phase 1
0.6688	Remote Similarity	NPD4380	Phase 2
0.6687	Remote Similarity	NPD7054	Approved
0.6687	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD4340	Discontinued
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9622	Approved
0.6667	Remote Similarity	NPD1465	Phase 2
0.6647	Remote Similarity	NPD7074	Phase 3
0.6647	Remote Similarity	NPD7472	Approved
0.6645	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4110	Phase 3
0.6645	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1535	Discovery
0.6642	Remote Similarity	NPD9379	Approved
0.6642	Remote Similarity	NPD7843	Approved
0.6642	Remote Similarity	NPD9377	Approved
0.6641	Remote Similarity	NPD291	Approved
0.6623	Remote Similarity	NPD2424	Discontinued
0.6623	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD9537	Phase 1
0.6621	Remote Similarity	NPD9536	Phase 1
0.6619	Remote Similarity	NPD1778	Approved
0.6619	Remote Similarity	NPD4626	Approved
0.6618	Remote Similarity	NPD7157	Approved
0.6618	Remote Similarity	NPD4198	Discontinued
0.6604	Remote Similarity	NPD37	Approved
0.66	Remote Similarity	NPD6032	Approved
0.66	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1551	Phase 2
0.6597	Remote Similarity	NPD5736	Approved
0.6596	Remote Similarity	NPD1481	Phase 2
0.6591	Remote Similarity	NPD2684	Approved
0.6584	Remote Similarity	NPD4967	Phase 2
0.6584	Remote Similarity	NPD4966	Approved
0.6584	Remote Similarity	NPD4965	Approved
0.6575	Remote Similarity	NPD1048	Approved
0.6573	Remote Similarity	NPD1164	Approved
0.6566	Remote Similarity	NPD7473	Discontinued
0.6562	Remote Similarity	NPD1242	Phase 1
0.6561	Remote Similarity	NPD3687	Approved
0.6561	Remote Similarity	NPD3686	Approved
0.6556	Remote Similarity	NPD5763	Approved
0.6556	Remote Similarity	NPD5762	Approved
0.6554	Remote Similarity	NPD274	Approved
0.6554	Remote Similarity	NPD1933	Approved
0.6554	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD275	Approved
0.6547	Remote Similarity	NPD5691	Approved
0.6544	Remote Similarity	NPD9281	Approved
0.6543	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD520	Approved
0.6528	Remote Similarity	NPD9619	Approved
0.6528	Remote Similarity	NPD1019	Discontinued
0.6528	Remote Similarity	NPD9620	Approved
0.6528	Remote Similarity	NPD9621	Approved
0.6527	Remote Similarity	NPD7228	Approved
0.6525	Remote Similarity	NPD422	Phase 1
0.6525	Remote Similarity	NPD1091	Approved
0.6524	Remote Similarity	NPD8127	Discontinued
0.6516	Remote Similarity	NPD4357	Discontinued
0.6514	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5958	Discontinued
0.6513	Remote Similarity	NPD4534	Discontinued
0.6503	Remote Similarity	NPD919	Approved
0.65	Remote Similarity	NPD111	Approved
0.6494	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3620	Phase 2
0.6486	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6599	Discontinued
0.6475	Remote Similarity	NPD1894	Discontinued
0.6474	Remote Similarity	NPD8150	Discontinued
0.6474	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5283	Phase 1
0.6471	Remote Similarity	NPD1652	Phase 2
0.6471	Remote Similarity	NPD1241	Discontinued
0.6463	Remote Similarity	NPD2313	Discontinued
0.6462	Remote Similarity	NPD9261	Approved
0.6458	Remote Similarity	NPD1470	Approved
0.6439	Remote Similarity	NPD968	Approved
0.6438	Remote Similarity	NPD6832	Phase 2
0.6429	Remote Similarity	NPD5585	Approved
0.6429	Remote Similarity	NPD9296	Approved
0.6424	Remote Similarity	NPD2799	Discontinued
0.6424	Remote Similarity	NPD1510	Phase 2
0.6419	Remote Similarity	NPD6663	Approved
0.6415	Remote Similarity	NPD824	Approved
0.6408	Remote Similarity	NPD3705	Approved
0.6405	Remote Similarity	NPD1549	Phase 2
0.6391	Remote Similarity	NPD5844	Phase 1
0.6391	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3225	Approved
0.6389	Remote Similarity	NPD1283	Approved
0.6387	Remote Similarity	NPD2354	Approved
0.6386	Remote Similarity	NPD3787	Discontinued
0.6382	Remote Similarity	NPD2438	Suspended
0.6379	Remote Similarity	NPD8434	Phase 2
0.6376	Remote Similarity	NPD3062	Approved
0.6376	Remote Similarity	NPD3061	Approved
0.6376	Remote Similarity	NPD3059	Approved
0.6374	Remote Similarity	NPD6559	Discontinued
0.6369	Remote Similarity	NPD3536	Discontinued
0.6369	Remote Similarity	NPD3688	Clinical (unspecified phase)

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