NPASS Compound

Structure

NPC164172 OpenBabel07101718222D 43 46 0 0 1 0 0 0 0 0999 V2000 -8.7648 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6308 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6308 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4968 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2872 -1.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4968 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -2.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8366 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8366 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7026 -4.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5686 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5686 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2007 -0.8392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3629 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6308 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 -0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 17 2 0 0 0 0 2 8 2 0 0 0 0 2 17 1 0 0 0 0 3 9 1 0 0 0 0 3 18 2 0 0 0 0 4 10 2 0 0 0 0 4 18 1 0 0 0 0 5 11 1 0 0 0 0 5 17 1 0 0 0 0 6 12 1 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 14 40 1 0 0 0 0 15 30 1 0 0 0 0 15 31 1 0 0 0 0 16 30 1 0 0 0 0 16 41 1 0 0 0 0 19 32 1 0 0 0 0 20 33 1 0 0 0 0 21 34 2 0 0 0 0 22 12 1 6 0 0 0 22 42 1 0 0 0 0 23 14 1 6 0 0 0 23 24 1 0 0 0 0 23 43 1 0 0 0 0 24 25 1 0 0 0 0 24 35 1 1 0 0 0 25 26 1 0 0 0 0 25 36 1 6 0 0 0 26 28 1 0 0 0 0 26 37 1 1 0 0 0 27 29 1 0 0 0 0 27 30 1 1 0 0 0 27 38 1 0 0 0 0 28 42 1 6 0 0 0 28 43 1 0 0 0 0 29 40 1 6 0 0 0 29 41 1 0 0 0 0 30 39 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.25
Volume:	589.028
LogP:	0.157
LogD:	-0.212
LogS:	-2.681
# Rotatable Bonds:	14
TPSA:	215.83
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.133
Synthetic Accessibility Score:	4.711
Fsp3:	0.567
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.3
MDCK Permeability:	5.046303613198688e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.991
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	67.11104583740234%
Volume Distribution (VD):	0.218
Pgp-substrate:	14.702471733093262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.241
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	1.255
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.413
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.381
Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.17
Skin Sensitization:	0.925
Carcinogencity:	0.163
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.059

Download Data

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

Natural Product: NPC164172

Natural Product ID:	NPC164172
*Common Name:**	(5S)-5-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-Dihydroxy-4-(Hydroxymethyl)Oxolan-2-Yl]Oxymethyl]-3,4,5-Trihydroxyoxan-2-Yl]Oxy-1,7-Bis(4-Hydroxyphenyl)Heptan-3-One
IUPAC Name:	(5S)-5-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-1,7-bis(4-hydroxyphenyl)heptan-3-one
Synonyms:
Standard InCHIKey:	FBJBPTHRQGMFOK-ZRAWXLKHSA-N
Standard InCHI:	InChI=1S/C30H40O13/c31-15-30(39)16-41-29(27(30)38)40-14-23-24(35)25(36)26(37)28(43-23)42-22(12-6-18-3-9-20(33)10-4-18)13-21(34)11-5-17-1-7-19(32)8-2-17/h1-4,7-10,22-29,31-33,35-39H,5-6,11-16H2/t22-,23+,24+,25-,26+,27-,28+,29+,30+/m0/s1
SMILES:	c1cc(ccc1CCC(=O)C[C@H](CCc1ccc(cc1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@@](CO)(CO2)O)O)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774771
PubChem CID:	54582487
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO4971	Alnus firma	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504848]
NPO4971	Alnus firma	Species	Betulaceae	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	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	22.7	%	PMID[484930]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34900.0	nM	PMID[484930]

☑ 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 NPC164172 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	295
0.1-0.2	1012
0.2-0.3	2475
0.3-0.4	5932
0.4-0.5	11783
0.5-0.6	8113
0.6-0.7	10921
0.7-0.8	2030
0.8-0.85	103
0.85-0.9	20
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC471095
0.9921	High Similarity	NPC471066
0.9762	High Similarity	NPC469705
0.9762	High Similarity	NPC17968
0.9762	High Similarity	NPC470122
0.9692	High Similarity	NPC469696
0.9603	High Similarity	NPC158673
0.938	High Similarity	NPC476407
0.9206	High Similarity	NPC470907
0.9206	High Similarity	NPC232454
0.9206	High Similarity	NPC178449
0.9127	High Similarity	NPC471067
0.9098	High Similarity	NPC103398
0.9098	High Similarity	NPC180171
0.9098	High Similarity	NPC158325
0.8978	High Similarity	NPC469623
0.8978	High Similarity	NPC148080
0.8968	High Similarity	NPC201402
0.8968	High Similarity	NPC160854
0.8968	High Similarity	NPC469703
0.8968	High Similarity	NPC469704
0.8931	High Similarity	NPC469549
0.8923	High Similarity	NPC469687
0.8898	High Similarity	NPC469686
0.8819	High Similarity	NPC469548
0.8819	High Similarity	NPC476445
0.8819	High Similarity	NPC476448
0.8797	High Similarity	NPC478255
0.8777	High Similarity	NPC478250
0.874	High Similarity	NPC469702
0.874	High Similarity	NPC282409
0.8676	High Similarity	NPC123988
0.8613	High Similarity	NPC471345
0.8571	High Similarity	NPC225307
0.8551	High Similarity	NPC84789
0.8551	High Similarity	NPC302583
0.8551	High Similarity	NPC100558
0.8551	High Similarity	NPC310252
0.8538	High Similarity	NPC469927
0.8519	High Similarity	NPC281798
0.8496	Intermediate Similarity	NPC288416
0.8496	Intermediate Similarity	NPC231607
0.8496	Intermediate Similarity	NPC108659
0.8496	Intermediate Similarity	NPC264900
0.8496	Intermediate Similarity	NPC79715
0.8485	Intermediate Similarity	NPC123704
0.8483	Intermediate Similarity	NPC35097
0.8473	Intermediate Similarity	NPC236981
0.8472	Intermediate Similarity	NPC473138
0.8472	Intermediate Similarity	NPC28776
0.8472	Intermediate Similarity	NPC120728
0.8462	Intermediate Similarity	NPC212808
0.8462	Intermediate Similarity	NPC55608
0.8425	Intermediate Similarity	NPC148055
0.8421	Intermediate Similarity	NPC94179
0.8413	Intermediate Similarity	NPC157338
0.8403	Intermediate Similarity	NPC470330
0.8392	Intermediate Similarity	NPC475528
0.8382	Intermediate Similarity	NPC235294
0.8382	Intermediate Similarity	NPC46137
0.837	Intermediate Similarity	NPC184092
0.8357	Intermediate Similarity	NPC171134
0.8357	Intermediate Similarity	NPC328273
0.8357	Intermediate Similarity	NPC321184
0.8357	Intermediate Similarity	NPC321638
0.8346	Intermediate Similarity	NPC90318
0.8345	Intermediate Similarity	NPC116229
0.8333	Intermediate Similarity	NPC119773
0.8333	Intermediate Similarity	NPC169398
0.8333	Intermediate Similarity	NPC475539
0.8333	Intermediate Similarity	NPC474268
0.8333	Intermediate Similarity	NPC143246
0.8322	Intermediate Similarity	NPC194938
0.8322	Intermediate Similarity	NPC296659
0.8322	Intermediate Similarity	NPC202391
0.8311	Intermediate Similarity	NPC87403
0.8284	Intermediate Similarity	NPC252114
0.8267	Intermediate Similarity	NPC265480
0.8267	Intermediate Similarity	NPC149368
0.8261	Intermediate Similarity	NPC28637
0.8255	Intermediate Similarity	NPC160882
0.8248	Intermediate Similarity	NPC138777
0.8248	Intermediate Similarity	NPC225384
0.8248	Intermediate Similarity	NPC246869
0.8243	Intermediate Similarity	NPC106818
0.8227	Intermediate Similarity	NPC324262
0.8227	Intermediate Similarity	NPC62800
0.8224	Intermediate Similarity	NPC200708
0.8222	Intermediate Similarity	NPC35288
0.8222	Intermediate Similarity	NPC106677
0.8222	Intermediate Similarity	NPC45224
0.8222	Intermediate Similarity	NPC156692
0.8222	Intermediate Similarity	NPC173150
0.8222	Intermediate Similarity	NPC471881
0.8222	Intermediate Similarity	NPC471882
0.8214	Intermediate Similarity	NPC472132
0.8212	Intermediate Similarity	NPC122809
0.8209	Intermediate Similarity	NPC126991
0.8209	Intermediate Similarity	NPC83218
0.8207	Intermediate Similarity	NPC473147
0.82	Intermediate Similarity	NPC38699
0.8194	Intermediate Similarity	NPC63304
0.8188	Intermediate Similarity	NPC245615
0.8188	Intermediate Similarity	NPC257847
0.8188	Intermediate Similarity	NPC259182
0.8188	Intermediate Similarity	NPC121001
0.8188	Intermediate Similarity	NPC61604
0.8188	Intermediate Similarity	NPC299706
0.8188	Intermediate Similarity	NPC254275
0.8188	Intermediate Similarity	NPC115466
0.8176	Intermediate Similarity	NPC474620
0.8175	Intermediate Similarity	NPC177576
0.8163	Intermediate Similarity	NPC287294
0.8162	Intermediate Similarity	NPC148982
0.8156	Intermediate Similarity	NPC101686
0.8156	Intermediate Similarity	NPC65262
0.8156	Intermediate Similarity	NPC469364
0.8148	Intermediate Similarity	NPC471157
0.8148	Intermediate Similarity	NPC61181
0.8146	Intermediate Similarity	NPC478055
0.8146	Intermediate Similarity	NPC163635
0.8143	Intermediate Similarity	NPC263829
0.814	Intermediate Similarity	NPC473556
0.814	Intermediate Similarity	NPC175771
0.814	Intermediate Similarity	NPC301651
0.8133	Intermediate Similarity	NPC106625
0.8125	Intermediate Similarity	NPC105005
0.8125	Intermediate Similarity	NPC313193
0.8125	Intermediate Similarity	NPC40305
0.812	Intermediate Similarity	NPC52097
0.8108	Intermediate Similarity	NPC12006
0.8108	Intermediate Similarity	NPC158635
0.8108	Intermediate Similarity	NPC229882
0.8108	Intermediate Similarity	NPC117346
0.8108	Intermediate Similarity	NPC240592
0.8105	Intermediate Similarity	NPC208676
0.8105	Intermediate Similarity	NPC130489
0.8102	Intermediate Similarity	NPC11025
0.8099	Intermediate Similarity	NPC220942
0.8095	Intermediate Similarity	NPC252544
0.8095	Intermediate Similarity	NPC321252
0.8095	Intermediate Similarity	NPC472339
0.8088	Intermediate Similarity	NPC103533
0.8085	Intermediate Similarity	NPC470572
0.8082	Intermediate Similarity	NPC291153
0.8079	Intermediate Similarity	NPC97052
0.8079	Intermediate Similarity	NPC26195
0.8079	Intermediate Similarity	NPC131532
0.8079	Intermediate Similarity	NPC72649
0.8079	Intermediate Similarity	NPC99233
0.8079	Intermediate Similarity	NPC39351
0.8079	Intermediate Similarity	NPC169248
0.8077	Intermediate Similarity	NPC469419
0.8071	Intermediate Similarity	NPC471029
0.8071	Intermediate Similarity	NPC287597
0.8071	Intermediate Similarity	NPC886
0.8071	Intermediate Similarity	NPC34293
0.8069	Intermediate Similarity	NPC141455
0.8069	Intermediate Similarity	NPC251062
0.8069	Intermediate Similarity	NPC296954
0.8069	Intermediate Similarity	NPC196063
0.8069	Intermediate Similarity	NPC184464
0.8069	Intermediate Similarity	NPC300894
0.8067	Intermediate Similarity	NPC259767
0.8067	Intermediate Similarity	NPC88484
0.8052	Intermediate Similarity	NPC477627
0.8045	Intermediate Similarity	NPC266045
0.8045	Intermediate Similarity	NPC11724
0.8041	Intermediate Similarity	NPC96599
0.8041	Intermediate Similarity	NPC478242
0.8039	Intermediate Similarity	NPC469654
0.8028	Intermediate Similarity	NPC260425
0.8026	Intermediate Similarity	NPC127406
0.8026	Intermediate Similarity	NPC206378
0.8026	Intermediate Similarity	NPC170475
0.8014	Intermediate Similarity	NPC210330
0.8013	Intermediate Similarity	NPC39360
0.8013	Intermediate Similarity	NPC83283
0.8013	Intermediate Similarity	NPC29763
0.8013	Intermediate Similarity	NPC476194
0.8013	Intermediate Similarity	NPC210003
0.8013	Intermediate Similarity	NPC143851
0.8	Intermediate Similarity	NPC244454
0.8	Intermediate Similarity	NPC150164
0.8	Intermediate Similarity	NPC114116
0.8	Intermediate Similarity	NPC287429
0.8	Intermediate Similarity	NPC186296
0.8	Intermediate Similarity	NPC46092
0.7987	Intermediate Similarity	NPC246469
0.7987	Intermediate Similarity	NPC142860
0.7987	Intermediate Similarity	NPC271270
0.7987	Intermediate Similarity	NPC97285
0.7986	Intermediate Similarity	NPC472711
0.7986	Intermediate Similarity	NPC108553
0.7984	Intermediate Similarity	NPC285350
0.7974	Intermediate Similarity	NPC313163
0.7974	Intermediate Similarity	NPC43638
0.7974	Intermediate Similarity	NPC161749
0.7974	Intermediate Similarity	NPC40920
0.7974	Intermediate Similarity	NPC258035

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 NPC164172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	678
0.2-0.3	1376
0.3-0.4	2780
0.4-0.5	2430
0.5-0.6	1235
0.6-0.7	386
0.7-0.8	29
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7974	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD7266	Discontinued
0.7688	Intermediate Similarity	NPD3818	Discontinued
0.7662	Intermediate Similarity	NPD8455	Phase 2
0.764	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6559	Discontinued
0.7593	Intermediate Similarity	NPD7074	Phase 3
0.7582	Intermediate Similarity	NPD4380	Phase 2
0.7531	Intermediate Similarity	NPD7054	Approved
0.7517	Intermediate Similarity	NPD6190	Approved
0.7485	Intermediate Similarity	NPD7472	Approved
0.7469	Intermediate Similarity	NPD7228	Approved
0.7397	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7251	Discontinued
0.7391	Intermediate Similarity	NPD1091	Approved
0.7372	Intermediate Similarity	NPD37	Approved
0.7358	Intermediate Similarity	NPD6234	Discontinued
0.7349	Intermediate Similarity	NPD7808	Phase 3
0.7347	Intermediate Similarity	NPD7033	Discontinued
0.7342	Intermediate Similarity	NPD4965	Approved
0.7342	Intermediate Similarity	NPD4967	Phase 2
0.7342	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD6797	Phase 2
0.7303	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7075	Discontinued
0.7292	Intermediate Similarity	NPD3764	Approved
0.7248	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5126	Approved
0.7246	Intermediate Similarity	NPD5125	Phase 3
0.7241	Intermediate Similarity	NPD6233	Phase 2
0.7237	Intermediate Similarity	NPD5058	Phase 3
0.7202	Intermediate Similarity	NPD8313	Approved
0.7202	Intermediate Similarity	NPD8312	Approved
0.72	Intermediate Similarity	NPD1549	Phase 2
0.7192	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7685	Pre-registration
0.7172	Intermediate Similarity	NPD6798	Discontinued
0.7162	Intermediate Similarity	NPD7097	Phase 1
0.7152	Intermediate Similarity	NPD1934	Approved
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3787	Discontinued
0.711	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4628	Phase 3
0.7105	Intermediate Similarity	NPD3400	Discontinued
0.7083	Intermediate Similarity	NPD7240	Approved
0.7055	Intermediate Similarity	NPD7199	Phase 2
0.7055	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5403	Approved
0.7044	Intermediate Similarity	NPD6801	Discontinued
0.703	Intermediate Similarity	NPD6166	Phase 2
0.703	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5048	Discontinued
0.7007	Intermediate Similarity	NPD6663	Approved
0.7	Intermediate Similarity	NPD1510	Phase 2
0.6986	Remote Similarity	NPD3027	Phase 3
0.6966	Remote Similarity	NPD5736	Approved
0.6959	Remote Similarity	NPD1613	Approved
0.6959	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3751	Discontinued
0.6943	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2860	Approved
0.6929	Remote Similarity	NPD2859	Approved
0.6923	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5401	Approved
0.6914	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1653	Approved
0.6897	Remote Similarity	NPD5647	Approved
0.6897	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4062	Phase 3
0.6887	Remote Similarity	NPD5588	Approved
0.6879	Remote Similarity	NPD3019	Approved
0.6879	Remote Similarity	NPD2932	Approved
0.6875	Remote Similarity	NPD7411	Suspended
0.6867	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6799	Approved
0.6857	Remote Similarity	NPD9545	Approved
0.6852	Remote Similarity	NPD5402	Approved
0.685	Remote Similarity	NPD2933	Approved
0.685	Remote Similarity	NPD2934	Approved
0.6849	Remote Similarity	NPD2861	Phase 2
0.6846	Remote Similarity	NPD1240	Approved
0.6846	Remote Similarity	NPD943	Approved
0.6836	Remote Similarity	NPD6535	Approved
0.6836	Remote Similarity	NPD6534	Approved
0.6828	Remote Similarity	NPD3094	Phase 2
0.6818	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7700	Phase 2
0.6816	Remote Similarity	NPD7699	Phase 2
0.6815	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2629	Approved
0.681	Remote Similarity	NPD3882	Suspended
0.679	Remote Similarity	NPD2801	Approved
0.679	Remote Similarity	NPD7819	Suspended
0.6788	Remote Similarity	NPD7843	Approved
0.6783	Remote Similarity	NPD1201	Approved
0.6783	Remote Similarity	NPD1535	Discovery
0.6774	Remote Similarity	NPD2575	Approved
0.6774	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8166	Discontinued
0.677	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3020	Approved
0.6761	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6823	Phase 2
0.6757	Remote Similarity	NPD7095	Approved
0.6755	Remote Similarity	NPD1607	Approved
0.6753	Remote Similarity	NPD2424	Discontinued
0.6752	Remote Similarity	NPD1511	Approved
0.675	Remote Similarity	NPD7458	Discontinued
0.6748	Remote Similarity	NPD3817	Phase 2
0.674	Remote Similarity	NPD6780	Approved
0.674	Remote Similarity	NPD6777	Approved
0.674	Remote Similarity	NPD6782	Approved
0.674	Remote Similarity	NPD6781	Approved
0.674	Remote Similarity	NPD6778	Approved
0.674	Remote Similarity	NPD6779	Approved
0.674	Remote Similarity	NPD6776	Approved
0.6738	Remote Similarity	NPD1894	Discontinued
0.6736	Remote Similarity	NPD1481	Phase 2
0.6732	Remote Similarity	NPD9570	Approved
0.6732	Remote Similarity	NPD2935	Discontinued
0.6732	Remote Similarity	NPD2796	Approved
0.6721	Remote Similarity	NPD7435	Discontinued
0.6715	Remote Similarity	NPD969	Suspended
0.6712	Remote Similarity	NPD1470	Approved
0.6711	Remote Similarity	NPD4536	Approved
0.6711	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4538	Approved
0.671	Remote Similarity	NPD6674	Discontinued
0.6708	Remote Similarity	NPD6599	Discontinued
0.6705	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7584	Approved
0.6691	Remote Similarity	NPD3022	Approved
0.6691	Remote Similarity	NPD3021	Approved
0.6689	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4908	Phase 1
0.6688	Remote Similarity	NPD6002	Phase 3
0.6688	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6005	Phase 3
0.6688	Remote Similarity	NPD6004	Phase 3
0.6686	Remote Similarity	NPD8434	Phase 2
0.6686	Remote Similarity	NPD8150	Discontinued
0.6685	Remote Similarity	NPD8320	Phase 1
0.6685	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD8319	Approved
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD3092	Approved
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD3705	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD5960	Phase 3
0.6667	Remote Similarity	NPD1512	Approved
0.6647	Remote Similarity	NPD7799	Discontinued
0.6645	Remote Similarity	NPD5958	Discontinued
0.6645	Remote Similarity	NPD6653	Approved
0.6644	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7157	Approved
0.663	Remote Similarity	NPD7680	Approved
0.663	Remote Similarity	NPD7698	Approved
0.663	Remote Similarity	NPD7696	Phase 3
0.663	Remote Similarity	NPD7697	Approved
0.6628	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5406	Approved
0.6623	Remote Similarity	NPD6099	Approved
0.6623	Remote Similarity	NPD6100	Approved
0.6623	Remote Similarity	NPD5408	Approved
0.6623	Remote Similarity	NPD5404	Approved
0.6623	Remote Similarity	NPD5405	Approved
0.6622	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1548	Phase 1
0.6618	Remote Similarity	NPD2684	Approved
0.6606	Remote Similarity	NPD7768	Phase 2
0.6605	Remote Similarity	NPD7028	Phase 2
0.6604	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3268	Approved
0.66	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1164	Approved
0.6599	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD4103	Phase 2
0.6599	Remote Similarity	NPD2797	Approved
0.6597	Remote Similarity	NPD3847	Discontinued
0.6595	Remote Similarity	NPD7870	Phase 2
0.6595	Remote Similarity	NPD7871	Phase 2
0.6592	Remote Similarity	NPD6213	Phase 3
0.6592	Remote Similarity	NPD6212	Phase 3
0.6592	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7473	Discontinued
0.6587	Remote Similarity	NPD5494	Approved
0.6579	Remote Similarity	NPD230	Phase 1

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