NPASS Compound

Structure

CID270751 OpenBabel06191716072D 40 43 0 0 1 0 0 0 0 0999 V2000 -2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3690 -7.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8690 -3.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3690 -5.8660 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 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3690 -5.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3690 -4.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5902 -3.2399 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 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8690 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -4.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3690 -5.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3690 -4.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8690 -5.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8690 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5683 -3.0320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8690 -6.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8690 -3.2679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8690 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -5.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 35 1 0 0 0 0 3 36 1 0 0 0 0 4 37 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 14 1 0 0 0 0 7 38 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 18 2 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 20 2 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 16 17 1 0 0 0 0 16 26 2 0 0 0 0 17 12 1 6 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 18 34 1 0 0 0 0 19 27 2 0 0 0 0 19 35 1 0 0 0 0 20 27 1 0 0 0 0 20 36 1 0 0 0 0 21 13 1 6 0 0 0 21 22 1 0 0 0 0 21 39 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 1 0 0 0 23 24 1 0 0 0 0 23 32 1 6 0 0 0 24 28 1 0 0 0 0 24 33 1 1 0 0 0 25 15 1 1 0 0 0 25 40 1 0 0 0 0 26 40 1 0 0 0 0 27 37 1 0 0 0 0 28 38 1 6 0 0 0 28 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	564.22
Volume:	545.646
LogP:	0.937
LogD:	1.215
LogS:	-3.285
# Rotatable Bonds:	11
TPSA:	165.76
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.261
Synthetic Accessibility Score:	4.412
Fsp3:	0.5
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:	-5.704
MDCK Permeability:	2.112701622536406e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.245
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.448
Plasma Protein Binding (PPB):	51.856597900390625%
Volume Distribution (VD):	0.327
Pgp-substrate:	28.680335998535156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.183
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.85

ADMET: Excretion

Clearance (CL):	3.429
Half-life (T1/2):	0.641

ADMET: Toxicity

hERG Blockers:	0.399
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.16
AMES Toxicity:	0.439
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.135
Skin Sensitization:	0.567
Carcinogencity:	0.08
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC270751

Natural Product ID:	NPC270751
*Common Name:**	Woorenoside I
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-[(2R,3S)-3-(hydroxymethyl)-7-methoxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoxy]oxane-3,4,5-triol
Synonyms:	Woorenoside I
Standard InCHIKey:	PFZHVYHTUGZLMZ-CDRUZBNESA-N
Standard InCHI:	InChI=1S/C28H36O12/c1-34-18-9-14(6-5-7-38-28-24(33)23(32)22(31)21(13-30)39-28)8-16-17(12-29)25(40-26(16)18)15-10-19(35-2)27(37-4)20(11-15)36-3/h5-6,8-11,17,21-25,28-33H,7,12-13H2,1-4H3/b6-5+/t17-,21-,22-,23+,24-,25+,28-/m1/s1
SMILES:	COc1cc(/C=C/CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)cc2[C@@H](CO)[C@H](c3cc(c(c(c3)OC)OC)OC)Oc12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486989
PubChem CID:	10347890
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[11000020]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21401114]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	15.4	%	PMID[484889]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	34.7	%	PMID[484889]
NPT2157	Cell Line	SUP-T1	Homo sapiens	Inhibition	=	32.1	%	PMID[484889]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	8.5	%	PMID[484889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	24.8	%	PMID[484889]
NPT2	Others	Unspecified		Inhibition	=	-5.4	%	PMID[484889]

☑ 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 NPC270751 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	443
0.1-0.2	1510
0.2-0.3	3731
0.3-0.4	9564
0.4-0.5	9032
0.5-0.6	4747
0.6-0.7	7587
0.7-0.8	4824
0.8-0.85	845
0.85-0.9	342
0.9-0.95	60
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC302610
0.972	High Similarity	NPC472709
0.972	High Similarity	NPC472710
0.9714	High Similarity	NPC79429
0.9714	High Similarity	NPC471667
0.9714	High Similarity	NPC217635
0.9645	High Similarity	NPC476301
0.9645	High Similarity	NPC43508
0.951	High Similarity	NPC213074
0.951	High Similarity	NPC39657
0.951	High Similarity	NPC193473
0.951	High Similarity	NPC275284
0.951	High Similarity	NPC114505
0.951	High Similarity	NPC15956
0.951	High Similarity	NPC224674
0.951	High Similarity	NPC31325
0.9379	High Similarity	NPC51328
0.9379	High Similarity	NPC286235
0.9379	High Similarity	NPC55158
0.9371	High Similarity	NPC475096
0.9333	High Similarity	NPC241600
0.9333	High Similarity	NPC173726
0.9315	High Similarity	NPC238140
0.9315	High Similarity	NPC98624
0.931	High Similarity	NPC248132
0.931	High Similarity	NPC130449
0.9306	High Similarity	NPC190714
0.9306	High Similarity	NPC99515
0.9301	High Similarity	NPC472713
0.9301	High Similarity	NPC187774
0.9301	High Similarity	NPC473046
0.9301	High Similarity	NPC118385
0.9301	High Similarity	NPC472712
0.9296	High Similarity	NPC246947
0.9247	High Similarity	NPC95392
0.9247	High Similarity	NPC55715
0.9247	High Similarity	NPC35877
0.9241	High Similarity	NPC227902
0.9236	High Similarity	NPC181615
0.9236	High Similarity	NPC180953
0.9231	High Similarity	NPC470950
0.9231	High Similarity	NPC185307
0.9225	High Similarity	NPC108674
0.9178	High Similarity	NPC71726
0.9178	High Similarity	NPC175976
0.9172	High Similarity	NPC125755
0.9172	High Similarity	NPC260397
0.9167	High Similarity	NPC283995
0.9167	High Similarity	NPC470235
0.9167	High Similarity	NPC25292
0.9167	High Similarity	NPC471063
0.9167	High Similarity	NPC473045
0.9167	High Similarity	NPC129417
0.9161	High Similarity	NPC5262
0.9161	High Similarity	NPC472714
0.9161	High Similarity	NPC189115
0.9161	High Similarity	NPC469559
0.9161	High Similarity	NPC253878
0.9161	High Similarity	NPC476356
0.9161	High Similarity	NPC475084
0.9155	High Similarity	NPC226547
0.9149	High Similarity	NPC477938
0.9143	High Similarity	NPC236522
0.9116	High Similarity	NPC240521
0.9103	High Similarity	NPC279298
0.9103	High Similarity	NPC22150
0.9103	High Similarity	NPC307466
0.9103	High Similarity	NPC38041
0.9103	High Similarity	NPC161700
0.9103	High Similarity	NPC277867
0.9097	High Similarity	NPC81638
0.9097	High Similarity	NPC46092
0.9097	High Similarity	NPC473044
0.9091	High Similarity	NPC471414
0.9091	High Similarity	NPC87725
0.9091	High Similarity	NPC472711
0.9091	High Similarity	NPC469661
0.9091	High Similarity	NPC263261
0.9085	High Similarity	NPC156376
0.9085	High Similarity	NPC292487
0.9078	High Similarity	NPC25695
0.9078	High Similarity	NPC172818
0.9071	High Similarity	NPC476411
0.9071	High Similarity	NPC187194
0.9067	High Similarity	NPC159922
0.906	High Similarity	NPC21902
0.906	High Similarity	NPC474442
0.906	High Similarity	NPC59692
0.9054	High Similarity	NPC145979
0.9054	High Similarity	NPC214326
0.9054	High Similarity	NPC185955
0.9054	High Similarity	NPC9933
0.9054	High Similarity	NPC182368
0.9054	High Similarity	NPC469706
0.9054	High Similarity	NPC225815
0.9054	High Similarity	NPC469707
0.9054	High Similarity	NPC218041
0.9054	High Similarity	NPC260781
0.9048	High Similarity	NPC301961
0.9048	High Similarity	NPC166584
0.9041	High Similarity	NPC276753
0.9041	High Similarity	NPC162193
0.9041	High Similarity	NPC205796
0.9041	High Similarity	NPC112861
0.9034	High Similarity	NPC168579
0.9034	High Similarity	NPC138227
0.9034	High Similarity	NPC12641
0.9034	High Similarity	NPC93323
0.9034	High Similarity	NPC469313
0.9034	High Similarity	NPC76176
0.9034	High Similarity	NPC280092
0.9034	High Similarity	NPC63879
0.9034	High Similarity	NPC45257
0.9028	High Similarity	NPC80326
0.9028	High Similarity	NPC472562
0.9028	High Similarity	NPC41782
0.9021	High Similarity	NPC309124
0.9021	High Similarity	NPC184797
0.9014	High Similarity	NPC283949
0.9014	High Similarity	NPC185908
0.9007	High Similarity	NPC470236
0.9	High Similarity	NPC263064
0.9	High Similarity	NPC196937
0.9	High Similarity	NPC215833
0.9	High Similarity	NPC69513
0.898	High Similarity	NPC473480
0.898	High Similarity	NPC15538
0.8973	High Similarity	NPC42716
0.8973	High Similarity	NPC205316
0.8973	High Similarity	NPC11422
0.8973	High Similarity	NPC178014
0.8973	High Similarity	NPC18979
0.8973	High Similarity	NPC474749
0.8966	High Similarity	NPC252169
0.8966	High Similarity	NPC47633
0.8966	High Similarity	NPC37793
0.8966	High Similarity	NPC85264
0.8966	High Similarity	NPC102044
0.8966	High Similarity	NPC477898
0.8958	High Similarity	NPC58137
0.8958	High Similarity	NPC210192
0.8958	High Similarity	NPC300798
0.8958	High Similarity	NPC471908
0.8951	High Similarity	NPC70682
0.8951	High Similarity	NPC212770
0.8951	High Similarity	NPC236306
0.8951	High Similarity	NPC473739
0.8951	High Similarity	NPC260741
0.8951	High Similarity	NPC232164
0.8951	High Similarity	NPC98777
0.8947	High Similarity	NPC228357
0.8944	High Similarity	NPC164857
0.8944	High Similarity	NPC78047
0.8936	High Similarity	NPC251981
0.8936	High Similarity	NPC13745
0.8936	High Similarity	NPC48863
0.8933	High Similarity	NPC470264
0.8929	High Similarity	NPC162093
0.8929	High Similarity	NPC230219
0.8919	High Similarity	NPC93924
0.8919	High Similarity	NPC280945
0.8912	High Similarity	NPC324492
0.8912	High Similarity	NPC226540
0.8912	High Similarity	NPC317053
0.8904	High Similarity	NPC84181
0.8897	High Similarity	NPC174522
0.8897	High Similarity	NPC472353
0.8897	High Similarity	NPC302506
0.8897	High Similarity	NPC107161
0.8889	High Similarity	NPC46591
0.8889	High Similarity	NPC27495
0.8889	High Similarity	NPC56091
0.8881	High Similarity	NPC138738
0.8881	High Similarity	NPC474039
0.8881	High Similarity	NPC65530
0.8881	High Similarity	NPC470413
0.8881	High Similarity	NPC59324
0.8874	High Similarity	NPC78809
0.8873	High Similarity	NPC61946
0.8873	High Similarity	NPC150534
0.8867	High Similarity	NPC473621
0.8865	High Similarity	NPC49074
0.8865	High Similarity	NPC58585
0.8865	High Similarity	NPC26394
0.8859	High Similarity	NPC44452
0.8857	High Similarity	NPC473412
0.8857	High Similarity	NPC469698
0.8851	High Similarity	NPC328567
0.8851	High Similarity	NPC320671
0.8851	High Similarity	NPC101376
0.8851	High Similarity	NPC327412
0.8851	High Similarity	NPC16269
0.8851	High Similarity	NPC320970
0.8851	High Similarity	NPC21776
0.8844	High Similarity	NPC469557
0.8836	High Similarity	NPC116922
0.8836	High Similarity	NPC324962
0.8836	High Similarity	NPC474808
0.8831	High Similarity	NPC478269
0.8831	High Similarity	NPC185231

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 NPC270751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	830
0.2-0.3	1807
0.3-0.4	2831
0.4-0.5	1730
0.5-0.6	940
0.6-0.7	542
0.7-0.8	103
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8699	High Similarity	NPD6674	Discontinued
0.8531	High Similarity	NPD1612	Clinical (unspecified phase)
0.8531	High Similarity	NPD1613	Approved
0.8387	Intermediate Similarity	NPD37	Approved
0.8365	Intermediate Similarity	NPD7199	Phase 2
0.8344	Intermediate Similarity	NPD4965	Approved
0.8344	Intermediate Similarity	NPD4966	Approved
0.8344	Intermediate Similarity	NPD4967	Phase 2
0.8333	Intermediate Similarity	NPD7228	Approved
0.8322	Intermediate Similarity	NPD3027	Phase 3
0.8252	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD1653	Approved
0.8239	Intermediate Similarity	NPD6234	Discontinued
0.8182	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7240	Approved
0.8121	Intermediate Similarity	NPD7074	Phase 3
0.811	Intermediate Similarity	NPD3818	Discontinued
0.8061	Intermediate Similarity	NPD7054	Approved
0.8014	Intermediate Similarity	NPD1091	Approved
0.8012	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD4908	Phase 1
0.7922	Intermediate Similarity	NPD5058	Phase 3
0.7917	Intermediate Similarity	NPD6559	Discontinued
0.7887	Intermediate Similarity	NPD3705	Approved
0.7887	Intermediate Similarity	NPD1610	Phase 2
0.7875	Intermediate Similarity	NPD8455	Phase 2
0.787	Intermediate Similarity	NPD7808	Phase 3
0.7843	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7266	Discontinued
0.7811	Intermediate Similarity	NPD7251	Discontinued
0.7808	Intermediate Similarity	NPD2861	Phase 2
0.777	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6797	Phase 2
0.7744	Intermediate Similarity	NPD5494	Approved
0.7738	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4625	Phase 3
0.7702	Intermediate Similarity	NPD1934	Approved
0.7687	Intermediate Similarity	NPD3018	Phase 2
0.7661	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5844	Phase 1
0.7603	Intermediate Similarity	NPD8651	Approved
0.7582	Intermediate Similarity	NPD5588	Approved
0.7561	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6166	Phase 2
0.756	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1357	Approved
0.755	Intermediate Similarity	NPD4060	Phase 1
0.7534	Intermediate Similarity	NPD4749	Approved
0.7534	Intermediate Similarity	NPD2982	Phase 2
0.7534	Intermediate Similarity	NPD2983	Phase 2
0.7516	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4538	Approved
0.7516	Intermediate Similarity	NPD4536	Approved
0.75	Intermediate Similarity	NPD5126	Approved
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5125	Phase 3
0.75	Intermediate Similarity	NPD5283	Phase 1
0.75	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5763	Approved
0.7484	Intermediate Similarity	NPD5762	Approved
0.7483	Intermediate Similarity	NPD1548	Phase 1
0.7466	Intermediate Similarity	NPD2981	Phase 2
0.7459	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6841	Approved
0.7443	Intermediate Similarity	NPD6843	Phase 3
0.7443	Intermediate Similarity	NPD6842	Approved
0.7439	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7819	Suspended
0.7429	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7075	Discontinued
0.7407	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7097	Phase 1
0.7394	Intermediate Similarity	NPD7157	Approved
0.7391	Intermediate Similarity	NPD7680	Approved
0.7389	Intermediate Similarity	NPD1652	Phase 2
0.7386	Intermediate Similarity	NPD5735	Approved
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7383	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4380	Phase 2
0.7355	Intermediate Similarity	NPD4108	Discontinued
0.7355	Intermediate Similarity	NPD5960	Phase 3
0.7349	Intermediate Similarity	NPD3882	Suspended
0.7342	Intermediate Similarity	NPD6331	Phase 2
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.7333	Intermediate Similarity	NPD2801	Approved
0.732	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3620	Phase 2
0.7317	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7473	Discontinued
0.7305	Intermediate Similarity	NPD7843	Approved
0.7299	Intermediate Similarity	NPD7685	Pre-registration
0.7289	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3382	Approved
0.7273	Intermediate Similarity	NPD3384	Approved
0.7273	Intermediate Similarity	NPD3383	Approved
0.7261	Intermediate Similarity	NPD1375	Discontinued
0.7235	Intermediate Similarity	NPD6232	Discontinued
0.7235	Intermediate Similarity	NPD3051	Approved
0.7233	Intermediate Similarity	NPD3892	Phase 2
0.7233	Intermediate Similarity	NPD7466	Approved
0.7216	Intermediate Similarity	NPD8312	Approved
0.7216	Intermediate Similarity	NPD8313	Approved
0.7215	Intermediate Similarity	NPD2424	Discontinued
0.7193	Intermediate Similarity	NPD2970	Approved
0.7193	Intermediate Similarity	NPD2969	Approved
0.7188	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5177	Phase 3
0.7169	Intermediate Similarity	NPD6801	Discontinued
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7549	Discontinued
0.7152	Intermediate Similarity	NPD3540	Phase 1
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2684	Approved
0.7134	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2977	Approved
0.7126	Intermediate Similarity	NPD2978	Approved
0.7126	Intermediate Similarity	NPD1465	Phase 2
0.7125	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4110	Phase 3
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7095	Approved
0.7117	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1511	Approved
0.7097	Intermediate Similarity	NPD4140	Approved
0.7091	Intermediate Similarity	NPD4005	Discontinued
0.7089	Intermediate Similarity	NPD6100	Approved
0.7089	Intermediate Similarity	NPD3539	Phase 1
0.7089	Intermediate Similarity	NPD6099	Approved
0.7081	Intermediate Similarity	NPD2677	Approved
0.7081	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6798	Discontinued
0.7071	Intermediate Similarity	NPD290	Approved
0.7069	Intermediate Similarity	NPD3751	Discontinued
0.7067	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5327	Phase 3
0.7063	Intermediate Similarity	NPD4236	Phase 3
0.7063	Intermediate Similarity	NPD4237	Approved
0.7056	Intermediate Similarity	NPD7906	Approved
0.7055	Intermediate Similarity	NPD7447	Phase 1
0.7055	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2489	Approved
0.7052	Intermediate Similarity	NPD27	Approved
0.7048	Intermediate Similarity	NPD4678	Approved
0.7048	Intermediate Similarity	NPD4675	Approved
0.7044	Intermediate Similarity	NPD6002	Phase 3
0.7044	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6004	Phase 3
0.7044	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6005	Phase 3
0.7037	Intermediate Similarity	NPD7124	Phase 2
0.7035	Intermediate Similarity	NPD6071	Discontinued
0.7034	Intermediate Similarity	NPD6671	Approved
0.7033	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7311	Approved
0.7022	Intermediate Similarity	NPD7310	Approved
0.7022	Intermediate Similarity	NPD7313	Approved
0.7022	Intermediate Similarity	NPD7312	Approved
0.702	Intermediate Similarity	NPD6696	Suspended
0.7019	Intermediate Similarity	NPD4535	Phase 3
0.7012	Intermediate Similarity	NPD1512	Approved
0.7012	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7411	Suspended
0.7006	Intermediate Similarity	NPD6653	Approved
0.7	Intermediate Similarity	NPD4663	Approved
0.6994	Remote Similarity	NPD7213	Phase 3
0.6994	Remote Similarity	NPD7212	Phase 2
0.6993	Remote Similarity	NPD228	Approved
0.6983	Remote Similarity	NPD7309	Approved
0.6982	Remote Similarity	NPD2560	Approved
0.6982	Remote Similarity	NPD5402	Approved
0.6982	Remote Similarity	NPD2563	Approved
0.6977	Remote Similarity	NPD6959	Discontinued
0.6959	Remote Similarity	NPD919	Approved
0.6946	Remote Similarity	NPD7028	Phase 2
0.6941	Remote Similarity	NPD7768	Phase 2
0.6937	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6667	Approved
0.6933	Remote Similarity	NPD6666	Approved
0.6933	Remote Similarity	NPD422	Phase 1
0.6927	Remote Similarity	NPD4577	Approved
0.6927	Remote Similarity	NPD4578	Approved
0.6923	Remote Similarity	NPD6233	Phase 2

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