NPASS Compound

Structure

NPC219428 OpenBabel07101718222D 25 26 0 0 1 0 0 0 0 0999 V2000 -4.3301 -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 -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 -5.1962 -0.0000 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 -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 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 2.2321 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 1 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 0.8660 -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 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 2.7321 1.0000 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 3 2 0 0 0 0 1 8 1 0 0 0 0 2 4 2 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 6 16 1 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 6 0 0 0 12 14 1 0 0 0 0 12 20 1 1 0 0 0 13 21 2 0 0 0 0 13 25 1 0 0 0 0 14 25 1 6 0 0 0 15 16 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.1
Volume:	331.473
LogP:	0.3
LogD:	-0.149
LogS:	-1.179
# Rotatable Bonds:	5
TPSA:	164.75
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.234
Synthetic Accessibility Score:	3.585
Fsp3:	0.375
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:	-6.451
MDCK Permeability:	0.00010924896923825145
Pgp-inhibitor:	0.0
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.864
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.732
Plasma Protein Binding (PPB):	44.11622619628906%
Volume Distribution (VD):	0.48
Pgp-substrate:	49.692535400390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.169
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.107
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	1.828
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.46
Skin Sensitization:	0.557
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.05
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC219428

Natural Product ID:	NPC219428
*Common Name:**	GYFFKZTYYAFCTR-QHEBTOHLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GYFFKZTYYAFCTR-QHEBTOHLSA-N
Standard InCHI:	InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16-/m1/s1
SMILES:	c1cc(c(cc1/C=C/C(=O)O[C@@H]1[C@@H](C[C@@](C[C@H]1O)(C(=O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3092676
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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT380	Cell Line	U-251	Homo sapiens	Activity	=	52.79	%	PMID[463233]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	132.64	%	PMID[463233]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	30.0	%	PMID[463232]

☑ 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 NPC219428 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	320
0.1-0.2	1243
0.2-0.3	3282
0.3-0.4	7308
0.4-0.5	10149
0.5-0.6	5814
0.6-0.7	8865
0.7-0.8	5334
0.8-0.85	265
0.85-0.9	57
0.9-0.95	19
0.95-1	41

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC302857
1.0	High Similarity	NPC142703
1.0	High Similarity	NPC152942
1.0	High Similarity	NPC278068
1.0	High Similarity	NPC37250
0.9924	High Similarity	NPC295492
0.9924	High Similarity	NPC205751
0.9924	High Similarity	NPC274891
0.9924	High Similarity	NPC474875
0.9924	High Similarity	NPC476820
0.9924	High Similarity	NPC26241
0.9924	High Similarity	NPC476819
0.9924	High Similarity	NPC303683
0.9776	High Similarity	NPC224389
0.9776	High Similarity	NPC35702
0.9776	High Similarity	NPC297517
0.9776	High Similarity	NPC477335
0.9776	High Similarity	NPC13818
0.9776	High Similarity	NPC206095
0.9776	High Similarity	NPC471027
0.9704	High Similarity	NPC37331
0.9704	High Similarity	NPC284948
0.9704	High Similarity	NPC472016
0.9704	High Similarity	NPC277315
0.9704	High Similarity	NPC220664
0.9704	High Similarity	NPC192831
0.9704	High Similarity	NPC319628
0.9704	High Similarity	NPC303090
0.9704	High Similarity	NPC43158
0.9704	High Similarity	NPC258469
0.9695	High Similarity	NPC68517
0.9621	High Similarity	NPC70680
0.9621	High Similarity	NPC182217
0.9621	High Similarity	NPC233350
0.9493	High Similarity	NPC98356
0.942	High Similarity	NPC477333
0.9407	High Similarity	NPC283560
0.9407	High Similarity	NPC24295
0.9357	High Similarity	NPC192568
0.9357	High Similarity	NPC471076
0.9348	High Similarity	NPC50221
0.9348	High Similarity	NPC114242
0.9291	High Similarity	NPC42464
0.9286	High Similarity	NPC322660
0.9225	High Similarity	NPC306343
0.922	High Similarity	NPC43123
0.9111	High Similarity	NPC474895
0.9104	High Similarity	NPC18074
0.9104	High Similarity	NPC5419
0.9104	High Similarity	NPC61
0.9104	High Similarity	NPC25581
0.9097	High Similarity	NPC163883
0.9097	High Similarity	NPC93498
0.9058	High Similarity	NPC179505
0.9058	High Similarity	NPC156709
0.9037	High Similarity	NPC155209
0.9037	High Similarity	NPC168799
0.9034	High Similarity	NPC19380
0.9034	High Similarity	NPC146277
0.903	High Similarity	NPC198388
0.9028	High Similarity	NPC477334
0.9014	High Similarity	NPC229264
0.8936	High Similarity	NPC226738
0.8936	High Similarity	NPC190587
0.8936	High Similarity	NPC22176
0.8936	High Similarity	NPC121573
0.8929	High Similarity	NPC477278
0.8929	High Similarity	NPC477277
0.8921	High Similarity	NPC12218
0.8921	High Similarity	NPC225036
0.8921	High Similarity	NPC75763
0.8921	High Similarity	NPC105525
0.8913	High Similarity	NPC67349
0.8913	High Similarity	NPC279676
0.8912	High Similarity	NPC145425
0.8897	High Similarity	NPC252979
0.8857	High Similarity	NPC477279
0.8851	High Similarity	NPC470896
0.8851	High Similarity	NPC473275
0.8849	High Similarity	NPC239943
0.8832	High Similarity	NPC106406
0.8811	High Similarity	NPC473867
0.8797	High Similarity	NPC475695
0.8759	High Similarity	NPC471749
0.8759	High Similarity	NPC75945
0.875	High Similarity	NPC318799
0.869	High Similarity	NPC248257
0.869	High Similarity	NPC120621
0.869	High Similarity	NPC142528
0.869	High Similarity	NPC472969
0.8676	High Similarity	NPC217052
0.8676	High Similarity	NPC329344
0.8676	High Similarity	NPC237506
0.8676	High Similarity	NPC32626
0.8671	High Similarity	NPC474692
0.8671	High Similarity	NPC229036
0.8652	High Similarity	NPC288452
0.8652	High Similarity	NPC289690
0.8649	High Similarity	NPC44730
0.8639	High Similarity	NPC140151
0.8633	High Similarity	NPC18646
0.863	High Similarity	NPC92117
0.8621	High Similarity	NPC221383
0.8621	High Similarity	NPC143892
0.8621	High Similarity	NPC283081
0.8621	High Similarity	NPC299090
0.8611	High Similarity	NPC108455
0.8603	High Similarity	NPC94810
0.8603	High Similarity	NPC226855
0.86	High Similarity	NPC134925
0.8592	High Similarity	NPC38473
0.8581	High Similarity	NPC246566
0.8581	High Similarity	NPC95498
0.8581	High Similarity	NPC75695
0.8571	High Similarity	NPC156892
0.8562	High Similarity	NPC98009
0.8561	High Similarity	NPC248150
0.8533	High Similarity	NPC203757
0.8519	High Similarity	NPC168653
0.8519	High Similarity	NPC251407
0.8511	High Similarity	NPC84789
0.8511	High Similarity	NPC302583
0.8511	High Similarity	NPC100558
0.8511	High Similarity	NPC310252
0.8507	High Similarity	NPC85565
0.8506	High Similarity	NPC227297
0.8503	High Similarity	NPC98809
0.8503	High Similarity	NPC476394
0.8489	Intermediate Similarity	NPC304929
0.8489	Intermediate Similarity	NPC1321
0.8489	Intermediate Similarity	NPC156124
0.8483	Intermediate Similarity	NPC258671
0.8483	Intermediate Similarity	NPC53884
0.8478	Intermediate Similarity	NPC108553
0.8467	Intermediate Similarity	NPC477293
0.8467	Intermediate Similarity	NPC229784
0.8467	Intermediate Similarity	NPC477294
0.8462	Intermediate Similarity	NPC9218
0.8456	Intermediate Similarity	NPC158654
0.8456	Intermediate Similarity	NPC476873
0.8451	Intermediate Similarity	NPC220942
0.8446	Intermediate Similarity	NPC473091
0.8446	Intermediate Similarity	NPC32197
0.8444	Intermediate Similarity	NPC132921
0.844	Intermediate Similarity	NPC470572
0.8429	Intermediate Similarity	NPC135127
0.8429	Intermediate Similarity	NPC287597
0.8429	Intermediate Similarity	NPC34293
0.8429	Intermediate Similarity	NPC886
0.8421	Intermediate Similarity	NPC147654
0.8421	Intermediate Similarity	NPC472271
0.8417	Intermediate Similarity	NPC473924
0.8414	Intermediate Similarity	NPC470130
0.8414	Intermediate Similarity	NPC160378
0.8414	Intermediate Similarity	NPC304956
0.8414	Intermediate Similarity	NPC473090
0.84	Intermediate Similarity	NPC44260
0.84	Intermediate Similarity	NPC327225
0.84	Intermediate Similarity	NPC205037
0.84	Intermediate Similarity	NPC16024
0.84	Intermediate Similarity	NPC61152
0.84	Intermediate Similarity	NPC3746
0.8397	Intermediate Similarity	NPC471823
0.8394	Intermediate Similarity	NPC232880
0.8382	Intermediate Similarity	NPC147192
0.8378	Intermediate Similarity	NPC478242
0.8369	Intermediate Similarity	NPC123988
0.8366	Intermediate Similarity	NPC287872
0.8366	Intermediate Similarity	NPC74319
0.8357	Intermediate Similarity	NPC477280
0.8357	Intermediate Similarity	NPC19719
0.8357	Intermediate Similarity	NPC477281
0.8357	Intermediate Similarity	NPC254398
0.8357	Intermediate Similarity	NPC129889
0.8357	Intermediate Similarity	NPC307006
0.8356	Intermediate Similarity	NPC469683
0.8345	Intermediate Similarity	NPC219677
0.8345	Intermediate Similarity	NPC264145
0.8344	Intermediate Similarity	NPC191046
0.8344	Intermediate Similarity	NPC128403
0.8344	Intermediate Similarity	NPC194095
0.8344	Intermediate Similarity	NPC327032
0.8333	Intermediate Similarity	NPC106818
0.8333	Intermediate Similarity	NPC326065
0.8322	Intermediate Similarity	NPC284409
0.8322	Intermediate Similarity	NPC259576
0.8322	Intermediate Similarity	NPC328273
0.8322	Intermediate Similarity	NPC321184
0.8322	Intermediate Similarity	NPC321638
0.8322	Intermediate Similarity	NPC171134
0.8322	Intermediate Similarity	NPC221091
0.831	Intermediate Similarity	NPC475111
0.8301	Intermediate Similarity	NPC226759
0.8301	Intermediate Similarity	NPC472860
0.8299	Intermediate Similarity	NPC9370
0.8299	Intermediate Similarity	NPC474465
0.8299	Intermediate Similarity	NPC287495
0.8296	Intermediate Similarity	NPC474275
0.8296	Intermediate Similarity	NPC224208
0.8289	Intermediate Similarity	NPC156624

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 NPC219428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	786
0.2-0.3	1765
0.3-0.4	2740
0.4-0.5	1985
0.5-0.6	1052
0.6-0.7	479
0.7-0.8	76
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9704	High Similarity	NPD6190	Approved
0.8489	Intermediate Similarity	NPD230	Phase 1
0.8194	Intermediate Similarity	NPD7266	Discontinued
0.8117	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD9269	Phase 2
0.7866	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3882	Suspended
0.7721	Intermediate Similarity	NPD9545	Approved
0.7707	Intermediate Similarity	NPD3817	Phase 2
0.7697	Intermediate Similarity	NPD7685	Pre-registration
0.7669	Intermediate Similarity	NPD3818	Discontinued
0.7667	Intermediate Similarity	NPD4628	Phase 3
0.7664	Intermediate Similarity	NPD9268	Approved
0.7662	Intermediate Similarity	NPD1653	Approved
0.7654	Intermediate Similarity	NPD6166	Phase 2
0.7654	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2801	Approved
0.7595	Intermediate Similarity	NPD5402	Approved
0.758	Intermediate Similarity	NPD1934	Approved
0.7569	Intermediate Similarity	NPD3027	Phase 3
0.7552	Intermediate Similarity	NPD9494	Approved
0.755	Intermediate Similarity	NPD8166	Discontinued
0.7534	Intermediate Similarity	NPD943	Approved
0.7532	Intermediate Similarity	NPD1512	Approved
0.7532	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6797	Phase 2
0.7518	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7075	Discontinued
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7466	Intermediate Similarity	NPD6233	Phase 2
0.7453	Intermediate Similarity	NPD6234	Discontinued
0.7452	Intermediate Similarity	NPD4380	Phase 2
0.745	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1465	Phase 2
0.741	Intermediate Similarity	NPD7054	Approved
0.741	Intermediate Similarity	NPD5844	Phase 1
0.7403	Intermediate Similarity	NPD1511	Approved
0.7403	Intermediate Similarity	NPD6799	Approved
0.7397	Intermediate Similarity	NPD3764	Approved
0.7389	Intermediate Similarity	NPD3455	Phase 2
0.7365	Intermediate Similarity	NPD7472	Approved
0.7365	Intermediate Similarity	NPD7074	Phase 3
0.7358	Intermediate Similarity	NPD6801	Discontinued
0.7358	Intermediate Similarity	NPD37	Approved
0.7349	Intermediate Similarity	NPD3751	Discontinued
0.7337	Intermediate Similarity	NPD7808	Phase 3
0.7329	Intermediate Similarity	NPD4966	Approved
0.7329	Intermediate Similarity	NPD4965	Approved
0.7329	Intermediate Similarity	NPD4967	Phase 2
0.7317	Intermediate Similarity	NPD6232	Discontinued
0.7312	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1613	Approved
0.7297	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8150	Discontinued
0.7261	Intermediate Similarity	NPD5403	Approved
0.7261	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7228	Approved
0.7212	Intermediate Similarity	NPD3787	Discontinued
0.72	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6385	Approved
0.7188	Intermediate Similarity	NPD6386	Approved
0.7186	Intermediate Similarity	NPD7473	Discontinued
0.7181	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2935	Discontinued
0.7171	Intermediate Similarity	NPD9570	Approved
0.7169	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8434	Phase 2
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6798	Discontinued
0.716	Intermediate Similarity	NPD5353	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7134	Intermediate Similarity	NPD5401	Approved
0.7133	Intermediate Similarity	NPD6355	Discontinued
0.7133	Intermediate Similarity	NPD447	Suspended
0.7125	Intermediate Similarity	NPD6599	Discontinued
0.7114	Intermediate Similarity	NPD4062	Phase 3
0.7086	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD825	Approved
0.7067	Intermediate Similarity	NPD826	Approved
0.705	Intermediate Similarity	NPD2629	Approved
0.7048	Intermediate Similarity	NPD8127	Discontinued
0.7032	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5536	Phase 2
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7819	Suspended
0.6993	Remote Similarity	NPD1510	Phase 2
0.6993	Remote Similarity	NPD7033	Discontinued
0.6988	Remote Similarity	NPD5494	Approved
0.6987	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4110	Phase 3
0.698	Remote Similarity	NPD7095	Approved
0.6968	Remote Similarity	NPD1549	Phase 2
0.6966	Remote Similarity	NPD1608	Approved
0.6964	Remote Similarity	NPD5242	Approved
0.6959	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4060	Phase 1
0.6948	Remote Similarity	NPD1551	Phase 2
0.6934	Remote Similarity	NPD3021	Approved
0.6934	Remote Similarity	NPD3022	Approved
0.6918	Remote Similarity	NPD2533	Approved
0.6918	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3146	Approved
0.6918	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2532	Approved
0.6918	Remote Similarity	NPD2534	Approved
0.6908	Remote Similarity	NPD4340	Discontinued
0.6908	Remote Similarity	NPD555	Phase 2
0.6903	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1535	Discovery
0.6879	Remote Similarity	NPD6559	Discontinued
0.6879	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3750	Approved
0.6871	Remote Similarity	NPD7411	Suspended
0.6863	Remote Similarity	NPD6653	Approved
0.6855	Remote Similarity	NPD4357	Discontinued
0.6849	Remote Similarity	NPD1481	Phase 2
0.6842	Remote Similarity	NPD1240	Approved
0.6835	Remote Similarity	NPD228	Approved
0.6835	Remote Similarity	NPD3887	Approved
0.6835	Remote Similarity	NPD2354	Approved
0.6833	Remote Similarity	NPD6535	Approved
0.6833	Remote Similarity	NPD6534	Approved
0.6831	Remote Similarity	NPD9493	Approved
0.6826	Remote Similarity	NPD919	Approved
0.6813	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2067	Discontinued
0.6811	Remote Similarity	NPD7435	Discontinued
0.6788	Remote Similarity	NPD8455	Phase 2
0.6788	Remote Similarity	NPD1358	Approved
0.6782	Remote Similarity	NPD7039	Approved
0.6782	Remote Similarity	NPD7038	Approved
0.6782	Remote Similarity	NPD7240	Approved
0.6779	Remote Similarity	NPD257	Approved
0.6779	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD258	Approved
0.6776	Remote Similarity	NPD259	Phase 1
0.6776	Remote Similarity	NPD6663	Approved
0.677	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3926	Phase 2
0.6759	Remote Similarity	NPD1778	Approved
0.6759	Remote Similarity	NPD17	Approved
0.6757	Remote Similarity	NPD3225	Approved
0.6753	Remote Similarity	NPD1607	Approved
0.6752	Remote Similarity	NPD5958	Discontinued
0.6752	Remote Similarity	NPD4534	Discontinued
0.6746	Remote Similarity	NPD1247	Approved
0.6739	Remote Similarity	NPD6779	Approved
0.6739	Remote Similarity	NPD6776	Approved
0.6739	Remote Similarity	NPD6780	Approved
0.6739	Remote Similarity	NPD6778	Approved
0.6739	Remote Similarity	NPD6781	Approved
0.6739	Remote Similarity	NPD6782	Approved
0.6739	Remote Similarity	NPD6777	Approved
0.6736	Remote Similarity	NPD1894	Discontinued
0.6733	Remote Similarity	NPD5736	Approved
0.6733	Remote Similarity	NPD9569	Approved
0.6731	Remote Similarity	NPD2438	Suspended
0.6731	Remote Similarity	NPD2796	Approved
0.6721	Remote Similarity	NPD7700	Phase 2
0.6721	Remote Similarity	NPD7699	Phase 2
0.6712	Remote Similarity	NPD3496	Discontinued
0.6711	Remote Similarity	NPD1203	Approved
0.671	Remote Similarity	NPD7097	Phase 1
0.6709	Remote Similarity	NPD1652	Phase 2
0.6708	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8313	Approved
0.6705	Remote Similarity	NPD8312	Approved
0.6692	Remote Similarity	NPD9495	Approved
0.669	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2983	Phase 2
0.6689	Remote Similarity	NPD2982	Phase 2
0.6688	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5763	Approved
0.6688	Remote Similarity	NPD5762	Approved
0.6687	Remote Similarity	NPD3687	Approved
0.6687	Remote Similarity	NPD3686	Approved
0.6686	Remote Similarity	NPD8368	Discontinued
0.6684	Remote Similarity	NPD8320	Phase 1
0.6684	Remote Similarity	NPD8319	Approved
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD1091	Approved
0.6647	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2424	Discontinued
0.6646	Remote Similarity	NPD3226	Approved
0.6644	Remote Similarity	NPD9381	Approved
0.6644	Remote Similarity	NPD9384	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