NPASS Compound

Structure

CID302610 OpenBabel06191716112D 43 46 0 0 1 0 0 0 0 0999 V2000 -10.4536 -2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9670 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4670 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9670 1.3660 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 -4.3301 -0.5000 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9670 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9670 -0.3660 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 -8.1883 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4754 -2.4190 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 -9.4670 0.5000 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 -7.8793 -0.3090 0.0000 C 0 0 2 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 -10.9670 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9670 -0.3660 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -8.4670 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4670 0.5000 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 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8063 -3.1622 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 0.0000 -3.0000 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 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4670 2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4670 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4670 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1664 -1.4680 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 -7.8793 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 36 1 0 0 0 0 3 37 1 0 0 0 0 4 38 1 0 0 0 0 5 39 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 16 1 0 0 0 0 8 40 1 0 0 0 0 9 16 2 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 10 20 2 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 22 2 0 0 0 0 13 31 1 0 0 0 0 14 41 1 0 0 0 0 15 32 2 0 0 0 0 15 41 1 0 0 0 0 18 19 1 0 0 0 0 18 28 2 0 0 0 0 19 14 1 1 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 20 36 1 0 0 0 0 21 29 2 0 0 0 0 21 37 1 0 0 0 0 22 29 1 0 0 0 0 22 38 1 0 0 0 0 23 13 1 6 0 0 0 23 24 1 0 0 0 0 23 42 1 0 0 0 0 24 25 1 0 0 0 0 24 33 1 1 0 0 0 25 26 1 0 0 0 0 25 34 1 6 0 0 0 26 30 1 0 0 0 0 26 35 1 1 0 0 0 27 17 1 6 0 0 0 27 43 1 0 0 0 0 28 43 1 0 0 0 0 29 39 1 0 0 0 0 30 40 1 6 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	606.23
Volume:	586.391
LogP:	1.43
LogD:	1.57
LogS:	-3.944
# Rotatable Bonds:	13
TPSA:	171.83
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	4.5
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:	-5.605
MDCK Permeability:	3.405985262361355e-05
Pgp-inhibitor:	0.635
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.124
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.392
Plasma Protein Binding (PPB):	48.54005432128906%
Volume Distribution (VD):	0.338
Pgp-substrate:	24.432697296142578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.122
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.869

ADMET: Excretion

Clearance (CL):	3.321
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.448
Human Hepatotoxicity (H-HT):	0.328
Drug-inuced Liver Injury (DILI):	0.419
AMES Toxicity:	0.543
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.181
Skin Sensitization:	0.578
Carcinogencity:	0.123
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC302610

Natural Product ID:	NPC302610
*Common Name:**	Woorenoside Ii
IUPAC Name:	[(2R,3S)-7-methoxy-5-[(E)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-enyl]-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]methyl acetate
Synonyms:	Woorenoside II
Standard InCHIKey:	ZIFCIVGCLRSBBD-DSLKXWCTSA-N
Standard InCHI:	InChI=1S/C30H38O13/c1-15(32)41-14-19-18-9-16(7-6-8-40-30-26(35)25(34)24(33)23(13-31)42-30)10-20(36-2)28(18)43-27(19)17-11-21(37-3)29(39-5)22(12-17)38-4/h6-7,9-12,19,23-27,30-31,33-35H,8,13-14H2,1-5H3/b7-6+/t19-,23-,24-,25+,26-,27+,30-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC/C=C/c2cc(OC)c3c(c2)[C@@H](COC(=O)C)[C@@H](O3)c2cc(OC)c(c(c2)OC)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453722
PubChem CID:	10326334
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
IC50	4
Others	2

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2157	Cell Line	SUP-T1	Homo sapiens	Inhibition	=	42.6	%	PMID[517755]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	75200.0	nM	PMID[517755]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	23700.0	nM	PMID[517755]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	20.5	%	PMID[517755]
NPT2	Others	Unspecified		IC50	=	39700.0	nM	PMID[517755]
NPT2	Others	Unspecified		IC50	=	48200.0	nM	PMID[517755]

☑ 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 NPC302610 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	329
0.1-0.2	1474
0.2-0.3	3401
0.3-0.4	8453
0.4-0.5	9774
0.5-0.6	5052
0.6-0.7	7288
0.7-0.8	5663
0.8-0.85	960
0.85-0.9	275
0.9-0.95	23
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC270751
0.96	High Similarity	NPC173726
0.96	High Similarity	NPC241600
0.9456	High Similarity	NPC472710
0.9456	High Similarity	NPC472709
0.9444	High Similarity	NPC79429
0.9444	High Similarity	NPC217635
0.9444	High Similarity	NPC471667
0.9379	High Similarity	NPC43508
0.9379	High Similarity	NPC476301
0.9252	High Similarity	NPC275284
0.9252	High Similarity	NPC224674
0.9252	High Similarity	NPC193473
0.9252	High Similarity	NPC15956
0.9252	High Similarity	NPC39657
0.9252	High Similarity	NPC114505
0.9252	High Similarity	NPC213074
0.9252	High Similarity	NPC31325
0.9211	High Similarity	NPC228357
0.92	High Similarity	NPC470264
0.9189	High Similarity	NPC93924
0.9128	High Similarity	NPC55158
0.9128	High Similarity	NPC286235
0.9128	High Similarity	NPC51328
0.9116	High Similarity	NPC475096
0.9091	High Similarity	NPC478269
0.9067	High Similarity	NPC238140
0.9067	High Similarity	NPC98624
0.9067	High Similarity	NPC158635
0.9067	High Similarity	NPC229882
0.906	High Similarity	NPC130449
0.906	High Similarity	NPC248132
0.9054	High Similarity	NPC190714
0.9054	High Similarity	NPC99515
0.9048	High Similarity	NPC187774
0.9048	High Similarity	NPC472713
0.9048	High Similarity	NPC473046
0.9048	High Similarity	NPC472712
0.9048	High Similarity	NPC118385
0.9045	High Similarity	NPC222531
0.9041	High Similarity	NPC246947
0.9041	High Similarity	NPC287124
0.9013	High Similarity	NPC150442
0.9	High Similarity	NPC55715
0.9	High Similarity	NPC106138
0.9	High Similarity	NPC95392
0.9	High Similarity	NPC35877
0.8993	High Similarity	NPC227902
0.8987	High Similarity	NPC475621
0.8986	High Similarity	NPC181615
0.8986	High Similarity	NPC180953
0.898	High Similarity	NPC470950
0.898	High Similarity	NPC185307
0.8974	High Similarity	NPC478267
0.8973	High Similarity	NPC108674
0.8958	High Similarity	NPC143895
0.8954	High Similarity	NPC473425
0.8947	High Similarity	NPC215060
0.8947	High Similarity	NPC169404
0.8947	High Similarity	NPC53587
0.8947	High Similarity	NPC176186
0.8947	High Similarity	NPC476352
0.894	High Similarity	NPC24425
0.8933	High Similarity	NPC325720
0.8933	High Similarity	NPC71726
0.8933	High Similarity	NPC175976
0.8933	High Similarity	NPC316676
0.8926	High Similarity	NPC212890
0.8926	High Similarity	NPC125755
0.8926	High Similarity	NPC260397
0.8919	High Similarity	NPC477701
0.8919	High Similarity	NPC166884
0.8919	High Similarity	NPC473045
0.8919	High Similarity	NPC470235
0.8919	High Similarity	NPC471063
0.8919	High Similarity	NPC283995
0.8919	High Similarity	NPC25292
0.8919	High Similarity	NPC129417
0.8919	High Similarity	NPC141569
0.8912	High Similarity	NPC253878
0.8912	High Similarity	NPC476356
0.8912	High Similarity	NPC131971
0.8912	High Similarity	NPC189115
0.8912	High Similarity	NPC5262
0.8912	High Similarity	NPC475084
0.8912	High Similarity	NPC469559
0.8912	High Similarity	NPC472714
0.8904	High Similarity	NPC226547
0.8897	High Similarity	NPC477938
0.8889	High Similarity	NPC245615
0.8889	High Similarity	NPC61604
0.8889	High Similarity	NPC236522
0.8889	High Similarity	NPC299706
0.8889	High Similarity	NPC115466
0.8882	High Similarity	NPC224472
0.8874	High Similarity	NPC240521
0.8867	High Similarity	NPC296377
0.8859	High Similarity	NPC307466
0.8859	High Similarity	NPC279298
0.8859	High Similarity	NPC22150
0.8859	High Similarity	NPC477702
0.8859	High Similarity	NPC161700
0.8859	High Similarity	NPC38041
0.8859	High Similarity	NPC277867
0.8854	High Similarity	NPC100465
0.8854	High Similarity	NPC152424
0.8854	High Similarity	NPC115624
0.8851	High Similarity	NPC81638
0.8851	High Similarity	NPC473044
0.8851	High Similarity	NPC46092
0.8844	High Similarity	NPC469661
0.8844	High Similarity	NPC263261
0.8844	High Similarity	NPC471414
0.8844	High Similarity	NPC87725
0.8844	High Similarity	NPC472711
0.8839	High Similarity	NPC29727
0.8839	High Similarity	NPC473323
0.8836	High Similarity	NPC292487
0.8836	High Similarity	NPC156376
0.8831	High Similarity	NPC159922
0.8828	High Similarity	NPC172818
0.8828	High Similarity	NPC471719
0.8828	High Similarity	NPC25695
0.8824	High Similarity	NPC471154
0.8824	High Similarity	NPC21902
0.8824	High Similarity	NPC474442
0.8824	High Similarity	NPC59692
0.8819	High Similarity	NPC476411
0.8819	High Similarity	NPC187194
0.8816	High Similarity	NPC225815
0.8816	High Similarity	NPC473989
0.8816	High Similarity	NPC185955
0.8816	High Similarity	NPC214326
0.8816	High Similarity	NPC469706
0.8816	High Similarity	NPC260781
0.8816	High Similarity	NPC218041
0.8816	High Similarity	NPC182368
0.8816	High Similarity	NPC9933
0.8816	High Similarity	NPC145979
0.8816	High Similarity	NPC469707
0.8808	High Similarity	NPC301961
0.8808	High Similarity	NPC159697
0.8808	High Similarity	NPC96294
0.8808	High Similarity	NPC303013
0.8808	High Similarity	NPC474795
0.8808	High Similarity	NPC130959
0.8808	High Similarity	NPC166584
0.8808	High Similarity	NPC169510
0.8808	High Similarity	NPC474940
0.88	High Similarity	NPC199928
0.88	High Similarity	NPC276753
0.88	High Similarity	NPC74320
0.88	High Similarity	NPC162193
0.88	High Similarity	NPC107120
0.88	High Similarity	NPC112861
0.88	High Similarity	NPC205796
0.8792	High Similarity	NPC93323
0.8792	High Similarity	NPC280092
0.8792	High Similarity	NPC12641
0.8792	High Similarity	NPC469313
0.8792	High Similarity	NPC138227
0.8792	High Similarity	NPC326144
0.8792	High Similarity	NPC63879
0.8792	High Similarity	NPC168579
0.8792	High Similarity	NPC45257
0.8792	High Similarity	NPC76176
0.8784	High Similarity	NPC41782
0.8784	High Similarity	NPC80326
0.8784	High Similarity	NPC472562
0.8782	High Similarity	NPC125495
0.8776	High Similarity	NPC309124
0.8776	High Similarity	NPC184797
0.8767	High Similarity	NPC185908
0.8767	High Similarity	NPC124149
0.8767	High Similarity	NPC283949
0.8766	High Similarity	NPC308739
0.8766	High Similarity	NPC474606
0.8766	High Similarity	NPC126405
0.8766	High Similarity	NPC53669
0.8766	High Similarity	NPC24562
0.8766	High Similarity	NPC16791
0.8766	High Similarity	NPC297271
0.8766	High Similarity	NPC217708
0.8766	High Similarity	NPC77237
0.8766	High Similarity	NPC470769
0.8759	High Similarity	NPC470236
0.8759	High Similarity	NPC224941
0.8759	High Similarity	NPC311430
0.8758	High Similarity	NPC475756
0.875	High Similarity	NPC283839
0.875	High Similarity	NPC215833
0.875	High Similarity	NPC69513
0.875	High Similarity	NPC263064
0.875	High Similarity	NPC90896
0.875	High Similarity	NPC59516
0.875	High Similarity	NPC196937
0.8742	High Similarity	NPC52740
0.8742	High Similarity	NPC473480
0.8742	High Similarity	NPC15538
0.8733	High Similarity	NPC85624

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 NPC302610 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	854
0.2-0.3	1751
0.3-0.4	2769
0.4-0.5	1837
0.5-0.6	979
0.6-0.7	564
0.7-0.8	113
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8645	High Similarity	NPD37	Approved
0.8616	High Similarity	NPD7199	Phase 2
0.8599	High Similarity	NPD4965	Approved
0.8599	High Similarity	NPD4967	Phase 2
0.8599	High Similarity	NPD4966	Approved
0.858	High Similarity	NPD7228	Approved
0.8506	High Similarity	NPD1653	Approved
0.8491	Intermediate Similarity	NPD6234	Discontinued
0.8467	Intermediate Similarity	NPD6674	Discontinued
0.8395	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7240	Approved
0.8299	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1613	Approved
0.8144	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD3818	Discontinued
0.8125	Intermediate Similarity	NPD8455	Phase 2
0.8095	Intermediate Similarity	NPD3027	Phase 3
0.8092	Intermediate Similarity	NPD7266	Discontinued
0.8084	Intermediate Similarity	NPD7054	Approved
0.8047	Intermediate Similarity	NPD6559	Discontinued
0.8036	Intermediate Similarity	NPD7472	Approved
0.8027	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7808	Phase 3
0.7895	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5844	Phase 1
0.7836	Intermediate Similarity	NPD7251	Discontinued
0.7815	Intermediate Similarity	NPD4060	Phase 1
0.7805	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1091	Approved
0.7791	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4908	Phase 1
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7771	Intermediate Similarity	NPD5494	Approved
0.7765	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD5124	Phase 1
0.7763	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3817	Phase 2
0.7742	Intermediate Similarity	NPD5763	Approved
0.7742	Intermediate Similarity	NPD5762	Approved
0.773	Intermediate Similarity	NPD1934	Approved
0.7722	Intermediate Similarity	NPD5058	Phase 3
0.7683	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7819	Suspended
0.7682	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1610	Phase 2
0.7671	Intermediate Similarity	NPD3705	Approved
0.7662	Intermediate Similarity	NPD7097	Phase 1
0.7657	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7075	Discontinued
0.7647	Intermediate Similarity	NPD6355	Discontinued
0.7643	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1652	Phase 2
0.7609	Intermediate Similarity	NPD7680	Approved
0.76	Intermediate Similarity	NPD2861	Phase 2
0.7588	Intermediate Similarity	NPD6166	Phase 2
0.7588	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7229	Phase 3
0.7566	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7473	Discontinued
0.7529	Intermediate Similarity	NPD7685	Pre-registration
0.7515	Intermediate Similarity	NPD8127	Discontinued
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3018	Phase 2
0.7472	Intermediate Similarity	NPD6843	Phase 3
0.7472	Intermediate Similarity	NPD6842	Approved
0.7472	Intermediate Similarity	NPD6841	Approved
0.7471	Intermediate Similarity	NPD6232	Discontinued
0.7443	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD8312	Approved
0.741	Intermediate Similarity	NPD6801	Discontinued
0.7407	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD8651	Approved
0.7394	Intermediate Similarity	NPD4380	Phase 2
0.7389	Intermediate Similarity	NPD5588	Approved
0.7386	Intermediate Similarity	NPD7095	Approved
0.7386	Intermediate Similarity	NPD7549	Discontinued
0.7381	Intermediate Similarity	NPD3882	Suspended
0.7375	Intermediate Similarity	NPD4110	Phase 3
0.7375	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3787	Discontinued
0.7365	Intermediate Similarity	NPD2801	Approved
0.7365	Intermediate Similarity	NPD1465	Phase 2
0.7362	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4140	Approved
0.7347	Intermediate Similarity	NPD1357	Approved
0.7338	Intermediate Similarity	NPD6798	Discontinued
0.7333	Intermediate Similarity	NPD2982	Phase 2
0.7333	Intermediate Similarity	NPD4749	Approved
0.7333	Intermediate Similarity	NPD2983	Phase 2
0.7325	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4536	Approved
0.7325	Intermediate Similarity	NPD4538	Approved
0.7321	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5125	Phase 3
0.7297	Intermediate Similarity	NPD5126	Approved
0.7296	Intermediate Similarity	NPD6002	Phase 3
0.7296	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6004	Phase 3
0.7296	Intermediate Similarity	NPD6005	Phase 3
0.7296	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5283	Phase 1
0.7279	Intermediate Similarity	NPD1548	Phase 1
0.7267	Intermediate Similarity	NPD2981	Phase 2
0.7261	Intermediate Similarity	NPD6653	Approved
0.7253	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2424	Discontinued
0.7246	Intermediate Similarity	NPD7411	Suspended
0.7229	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5402	Approved
0.72	Intermediate Similarity	NPD422	Phase 1
0.7197	Intermediate Similarity	NPD5735	Approved
0.7193	Intermediate Similarity	NPD919	Approved
0.7192	Intermediate Similarity	NPD7157	Approved
0.719	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6233	Phase 2
0.7178	Intermediate Similarity	NPD6667	Approved
0.7178	Intermediate Similarity	NPD6666	Approved
0.7176	Intermediate Similarity	NPD7768	Phase 2
0.717	Intermediate Similarity	NPD4108	Discontinued
0.717	Intermediate Similarity	NPD5960	Phase 3
0.717	Intermediate Similarity	NPD7033	Discontinued
0.716	Intermediate Similarity	NPD6331	Phase 2
0.716	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3620	Phase 2
0.7134	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1511	Approved
0.7134	Intermediate Similarity	NPD6799	Approved
0.7125	Intermediate Similarity	NPD6099	Approved
0.7125	Intermediate Similarity	NPD6100	Approved
0.7108	Intermediate Similarity	NPD5403	Approved
0.7107	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7843	Approved
0.7102	Intermediate Similarity	NPD3751	Discontinued
0.7101	Intermediate Similarity	NPD3382	Approved
0.7101	Intermediate Similarity	NPD3383	Approved
0.7101	Intermediate Similarity	NPD3384	Approved
0.7091	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5401	Approved
0.7091	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1933	Approved
0.7086	Intermediate Similarity	NPD4481	Phase 3
0.7083	Intermediate Similarity	NPD6599	Discontinued
0.7081	Intermediate Similarity	NPD1375	Discontinued
0.7069	Intermediate Similarity	NPD3051	Approved
0.7059	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7466	Approved
0.7055	Intermediate Similarity	NPD3892	Phase 2
0.7055	Intermediate Similarity	NPD3750	Approved
0.7055	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1512	Approved
0.7039	Intermediate Similarity	NPD1608	Approved
0.7029	Intermediate Similarity	NPD2970	Approved
0.7029	Intermediate Similarity	NPD2969	Approved
0.7024	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7458	Discontinued
0.7019	Intermediate Similarity	NPD2438	Suspended
0.7019	Intermediate Similarity	NPD6032	Approved
0.7013	Intermediate Similarity	NPD2797	Approved
0.7012	Intermediate Similarity	NPD6190	Approved
0.7012	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6959	Discontinued
0.7006	Intermediate Similarity	NPD7985	Registered
0.7	Intermediate Similarity	NPD4433	Discontinued
0.7	Intermediate Similarity	NPD5691	Approved
0.6994	Remote Similarity	NPD5177	Phase 3
0.6994	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2532	Approved
0.6988	Remote Similarity	NPD2533	Approved
0.6988	Remote Similarity	NPD2534	Approved
0.6986	Remote Similarity	NPD5535	Approved
0.6982	Remote Similarity	NPD7028	Phase 2
0.6975	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3540	Phase 1
0.6974	Remote Similarity	NPD1611	Approved
0.6964	Remote Similarity	NPD3686	Approved
0.6964	Remote Similarity	NPD3687	Approved
0.6959	Remote Similarity	NPD2978	Approved
0.6959	Remote Similarity	NPD2977	Approved
0.6959	Remote Similarity	NPD8151	Discontinued
0.6957	Remote Similarity	NPD3748	Approved
0.6957	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4666	Phase 3

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