NPASS Compound

Structure

NPC474234 OpenBabel07101719252D 36 40 0 0 1 0 0 0 0 0999 V2000 -7.5836 -0.4184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9801 -0.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6492 -1.0421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6199 1.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2514 3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6418 1.1873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6146 3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2672 0.8600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8108 1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4062 0.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2891 0.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2514 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6273 -0.8342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9364 0.1169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9448 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6146 1.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9448 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0787 3.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2127 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4807 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2127 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6768 2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9349 0.0982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2965 -1.5773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8108 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0787 4.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3467 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9145 0.3248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9727 1.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0787 1.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3467 1.8917 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 1 31 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 3 13 1 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 7 2 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 12 5 1 6 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 27 1 0 0 0 0 14 31 1 0 0 0 0 15 9 1 1 0 0 0 15 17 1 0 0 0 0 15 34 1 0 0 0 0 16 22 1 0 0 0 0 16 24 1 6 0 0 0 17 18 1 0 0 0 0 17 28 1 6 0 0 0 18 19 1 0 0 0 0 18 29 1 1 0 0 0 19 23 1 0 0 0 0 19 30 1 6 0 0 0 20 21 1 0 0 0 0 20 32 1 1 0 0 0 21 24 1 6 0 0 0 21 36 1 0 0 0 0 22 33 1 0 0 0 0 22 35 1 1 0 0 0 23 34 1 0 0 0 0 23 35 1 1 0 0 0 24 10 1 1 0 0 0 24 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.17
Volume:	473.178
LogP:	0.455
LogD:	0.105
LogS:	-2.489
# Rotatable Bonds:	8
TPSA:	180.06
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.182
Synthetic Accessibility Score:	5.178
Fsp3:	0.583
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.194
MDCK Permeability:	7.365662895608693e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.87
Human Intestinal Absorption (HIA):	0.937
20% Bioavailability (F20%):	0.593
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.183
Plasma Protein Binding (PPB):	59.712806701660156%
Volume Distribution (VD):	0.334
Pgp-substrate:	25.420135498046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.281
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	2.464
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.201
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.119
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.291
Carcinogencity:	0.948
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC474234

Natural Product ID:	NPC474234
*Common Name:**	(-)-6-Feruloyl-Catalpol
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(1aR,1bS,2S,5aR,6S,6aS)-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenoxy]-1a-(hydroxymethyl)-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	PZQJSFUXSDAPFA-KXANSVNUSA-N
Standard InCHI:	InChI=1S/C24H30O12/c1-31-14-8-11(2-3-13(14)27)4-6-32-20-12-5-7-33-22(16(12)24(10-26)21(20)36-24)35-23-19(30)18(29)17(28)15(9-25)34-23/h2-8,12,15-23,25-30H,9-10H2,1H3/b6-4+/t12-,15-,16-,17-,18+,19-,20+,21+,22+,23+,24+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@]2(CO)O[C@H]2[C@H]3O/C=C/c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463912
PubChem CID:	44566578
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO10745	Stereospermum personatum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309309]
NPO10745	Stereospermum personatum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10745	Stereospermum personatum	Species	Bignoniaceae	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
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	SC50	=	40.49	uM	PMID[447452]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	150400.0	nM	PMID[447452]

☑ 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 NPC474234 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	459
0.1-0.2	1483
0.2-0.3	3883
0.3-0.4	9233
0.4-0.5	9721
0.5-0.6	8958
0.6-0.7	6772
0.7-0.8	1923
0.8-0.85	221
0.85-0.9	37
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9517	High Similarity	NPC89693
0.9517	High Similarity	NPC229548
0.9517	High Similarity	NPC478241
0.9247	High Similarity	NPC478249
0.9247	High Similarity	NPC269914
0.9195	High Similarity	NPC478248
0.9178	High Similarity	NPC147224
0.9139	High Similarity	NPC478265
0.9103	High Similarity	NPC18789
0.9041	High Similarity	NPC308178
0.8993	High Similarity	NPC6836
0.8986	High Similarity	NPC475824
0.8929	High Similarity	NPC470881
0.8921	High Similarity	NPC252833
0.8897	High Similarity	NPC478240
0.8873	High Similarity	NPC304152
0.8849	High Similarity	NPC248307
0.8849	High Similarity	NPC65942
0.8846	High Similarity	NPC301910
0.8846	High Similarity	NPC130730
0.8841	High Similarity	NPC307110
0.8819	High Similarity	NPC472711
0.8816	High Similarity	NPC478266
0.8794	High Similarity	NPC35731
0.8767	High Similarity	NPC84181
0.8767	High Similarity	NPC283995
0.8767	High Similarity	NPC470235
0.8767	High Similarity	NPC129417
0.8723	High Similarity	NPC25821
0.8699	High Similarity	NPC185307
0.8699	High Similarity	NPC263397
0.8699	High Similarity	NPC302286
0.8699	High Similarity	NPC88754
0.8699	High Similarity	NPC470950
0.8699	High Similarity	NPC237872
0.8699	High Similarity	NPC477898
0.8699	High Similarity	NPC116104
0.8699	High Similarity	NPC46092
0.869	High Similarity	NPC46644
0.8671	High Similarity	NPC199459
0.8671	High Similarity	NPC177035
0.8671	High Similarity	NPC52277
0.8654	High Similarity	NPC206815
0.8654	High Similarity	NPC476011
0.8649	High Similarity	NPC112861
0.863	High Similarity	NPC476356
0.8611	High Similarity	NPC138738
0.8611	High Similarity	NPC195196
0.8611	High Similarity	NPC470413
0.8601	High Similarity	NPC101624
0.8601	High Similarity	NPC184938
0.8592	High Similarity	NPC132895
0.8581	High Similarity	NPC22150
0.8581	High Similarity	NPC18979
0.8581	High Similarity	NPC38041
0.8581	High Similarity	NPC279298
0.8581	High Similarity	NPC179914
0.8571	High Similarity	NPC278961
0.8571	High Similarity	NPC113680
0.8571	High Similarity	NPC248355
0.8571	High Similarity	NPC166040
0.8552	High Similarity	NPC49597
0.8531	High Similarity	NPC107478
0.8526	High Similarity	NPC138993
0.8523	High Similarity	NPC37838
0.8521	High Similarity	NPC470270
0.8514	High Similarity	NPC472712
0.8514	High Similarity	NPC118385
0.8514	High Similarity	NPC472713
0.8514	High Similarity	NPC187774
0.8514	High Similarity	NPC473046
0.8511	High Similarity	NPC80600
0.8511	High Similarity	NPC472024
0.8503	High Similarity	NPC5262
0.8503	High Similarity	NPC48309
0.8503	High Similarity	NPC472714
0.85	High Similarity	NPC302378
0.8467	Intermediate Similarity	NPC39657
0.8467	Intermediate Similarity	NPC275284
0.8467	Intermediate Similarity	NPC114505
0.8467	Intermediate Similarity	NPC15956
0.8467	Intermediate Similarity	NPC193473
0.8467	Intermediate Similarity	NPC213074
0.8467	Intermediate Similarity	NPC224674
0.8467	Intermediate Similarity	NPC31325
0.8456	Intermediate Similarity	NPC469586
0.8456	Intermediate Similarity	NPC286245
0.8456	Intermediate Similarity	NPC272619
0.8451	Intermediate Similarity	NPC9912
0.844	Intermediate Similarity	NPC270849
0.844	Intermediate Similarity	NPC26653
0.8438	Intermediate Similarity	NPC208818
0.8431	Intermediate Similarity	NPC203664
0.8425	Intermediate Similarity	NPC212770
0.8425	Intermediate Similarity	NPC98777
0.8425	Intermediate Similarity	NPC156376
0.8425	Intermediate Similarity	NPC226005
0.8421	Intermediate Similarity	NPC98624
0.8421	Intermediate Similarity	NPC475224
0.8414	Intermediate Similarity	NPC157554
0.8408	Intermediate Similarity	NPC474936
0.8403	Intermediate Similarity	NPC87696
0.8403	Intermediate Similarity	NPC187194
0.8392	Intermediate Similarity	NPC106739
0.8392	Intermediate Similarity	NPC471505
0.8389	Intermediate Similarity	NPC253015
0.8389	Intermediate Similarity	NPC110063
0.8389	Intermediate Similarity	NPC473045
0.8389	Intermediate Similarity	NPC471065
0.8389	Intermediate Similarity	NPC25292
0.8378	Intermediate Similarity	NPC469559
0.8378	Intermediate Similarity	NPC246947
0.8378	Intermediate Similarity	NPC140502
0.8378	Intermediate Similarity	NPC475084
0.8378	Intermediate Similarity	NPC189115
0.8367	Intermediate Similarity	NPC106944
0.8356	Intermediate Similarity	NPC59324
0.8356	Intermediate Similarity	NPC65530
0.8355	Intermediate Similarity	NPC44452
0.8355	Intermediate Similarity	NPC51328
0.8355	Intermediate Similarity	NPC286235
0.8355	Intermediate Similarity	NPC55158
0.8345	Intermediate Similarity	NPC174191
0.8345	Intermediate Similarity	NPC142547
0.8345	Intermediate Similarity	NPC135777
0.8333	Intermediate Similarity	NPC43508
0.8333	Intermediate Similarity	NPC476301
0.8333	Intermediate Similarity	NPC49074
0.8333	Intermediate Similarity	NPC189730
0.8323	Intermediate Similarity	NPC478232
0.8322	Intermediate Similarity	NPC277804
0.8322	Intermediate Similarity	NPC166168
0.8322	Intermediate Similarity	NPC478239
0.8322	Intermediate Similarity	NPC473044
0.8311	Intermediate Similarity	NPC471908
0.8311	Intermediate Similarity	NPC469661
0.8311	Intermediate Similarity	NPC476334
0.8299	Intermediate Similarity	NPC100389
0.8299	Intermediate Similarity	NPC193666
0.8299	Intermediate Similarity	NPC88640
0.8299	Intermediate Similarity	NPC123526
0.8289	Intermediate Similarity	NPC130449
0.8289	Intermediate Similarity	NPC248132
0.8288	Intermediate Similarity	NPC164857
0.8288	Intermediate Similarity	NPC242028
0.8288	Intermediate Similarity	NPC203230
0.8286	Intermediate Similarity	NPC90318
0.8278	Intermediate Similarity	NPC190714
0.8278	Intermediate Similarity	NPC99515
0.8276	Intermediate Similarity	NPC476411
0.8276	Intermediate Similarity	NPC48863
0.8276	Intermediate Similarity	NPC251981
0.8276	Intermediate Similarity	NPC13745
0.8272	Intermediate Similarity	NPC21956
0.8269	Intermediate Similarity	NPC475484
0.8269	Intermediate Similarity	NPC164152
0.8267	Intermediate Similarity	NPC217635
0.8267	Intermediate Similarity	NPC184464
0.8267	Intermediate Similarity	NPC251062
0.8267	Intermediate Similarity	NPC471063
0.8267	Intermediate Similarity	NPC79429
0.8267	Intermediate Similarity	NPC471667
0.8264	Intermediate Similarity	NPC299144
0.8264	Intermediate Similarity	NPC162093
0.8261	Intermediate Similarity	NPC475621
0.8255	Intermediate Similarity	NPC157816
0.8255	Intermediate Similarity	NPC60249
0.8255	Intermediate Similarity	NPC253878
0.8252	Intermediate Similarity	NPC77040
0.8252	Intermediate Similarity	NPC241522
0.8252	Intermediate Similarity	NPC92164
0.8252	Intermediate Similarity	NPC187998
0.8252	Intermediate Similarity	NPC275950
0.8252	Intermediate Similarity	NPC145305
0.8252	Intermediate Similarity	NPC64201
0.8252	Intermediate Similarity	NPC181079
0.8252	Intermediate Similarity	NPC173308
0.8252	Intermediate Similarity	NPC242807
0.8252	Intermediate Similarity	NPC42300
0.8252	Intermediate Similarity	NPC153739
0.8252	Intermediate Similarity	NPC257582
0.8252	Intermediate Similarity	NPC174495
0.8243	Intermediate Similarity	NPC202700
0.8239	Intermediate Similarity	NPC474178
0.8239	Intermediate Similarity	NPC252307
0.8239	Intermediate Similarity	NPC245826
0.8231	Intermediate Similarity	NPC474039
0.8224	Intermediate Similarity	NPC99183
0.8219	Intermediate Similarity	NPC470236
0.8212	Intermediate Similarity	NPC476382
0.8212	Intermediate Similarity	NPC287615
0.8212	Intermediate Similarity	NPC83743
0.8212	Intermediate Similarity	NPC34587
0.8212	Intermediate Similarity	NPC262182
0.8212	Intermediate Similarity	NPC252292
0.8212	Intermediate Similarity	NPC475096
0.8212	Intermediate Similarity	NPC216819
0.8212	Intermediate Similarity	NPC34927
0.8212	Intermediate Similarity	NPC100998
0.821	Intermediate Similarity	NPC286809

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 NPC474234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	808
0.2-0.3	2100
0.3-0.4	2904
0.4-0.5	1743
0.5-0.6	965
0.6-0.7	266
0.7-0.8	26
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7685	Pre-registration
0.7885	Intermediate Similarity	NPD1653	Approved
0.7815	Intermediate Similarity	NPD7266	Discontinued
0.7808	Intermediate Similarity	NPD3027	Phase 3
0.777	Intermediate Similarity	NPD3620	Phase 2
0.777	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3705	Approved
0.766	Intermediate Similarity	NPD1357	Approved
0.7622	Intermediate Similarity	NPD1091	Approved
0.7597	Intermediate Similarity	NPD6674	Discontinued
0.7533	Intermediate Similarity	NPD1613	Approved
0.7533	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7228	Approved
0.7455	Intermediate Similarity	NPD6234	Discontinued
0.7432	Intermediate Similarity	NPD2861	Phase 2
0.7365	Intermediate Similarity	NPD7199	Phase 2
0.7362	Intermediate Similarity	NPD37	Approved
0.7338	Intermediate Similarity	NPD228	Approved
0.7333	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD4966	Approved
0.732	Intermediate Similarity	NPD6653	Approved
0.731	Intermediate Similarity	NPD7054	Approved
0.7297	Intermediate Similarity	NPD3094	Phase 2
0.7267	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7472	Approved
0.7255	Intermediate Similarity	NPD5735	Approved
0.7251	Intermediate Similarity	NPD3818	Discontinued
0.7216	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7074	Phase 3
0.7134	Intermediate Similarity	NPD5762	Approved
0.7134	Intermediate Similarity	NPD7028	Phase 2
0.7134	Intermediate Similarity	NPD5763	Approved
0.7126	Intermediate Similarity	NPD6797	Phase 2
0.7125	Intermediate Similarity	NPD5058	Phase 3
0.7113	Intermediate Similarity	NPD5283	Phase 1
0.7108	Intermediate Similarity	NPD2977	Approved
0.7108	Intermediate Similarity	NPD2978	Approved
0.7086	Intermediate Similarity	NPD7251	Discontinued
0.7081	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7808	Phase 3
0.7027	Intermediate Similarity	NPD3092	Approved
0.7025	Intermediate Similarity	NPD1375	Discontinued
0.6989	Remote Similarity	NPD7240	Approved
0.6968	Remote Similarity	NPD4140	Approved
0.6957	Remote Similarity	NPD6190	Approved
0.6933	Remote Similarity	NPD2983	Phase 2
0.6933	Remote Similarity	NPD2982	Phase 2
0.6928	Remote Similarity	NPD4908	Phase 1
0.6923	Remote Similarity	NPD3657	Discovery
0.6908	Remote Similarity	NPD4624	Approved
0.6897	Remote Similarity	NPD7157	Approved
0.6882	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6353	Approved
0.6867	Remote Similarity	NPD2981	Phase 2
0.6863	Remote Similarity	NPD3018	Phase 2
0.686	Remote Similarity	NPD8127	Discontinued
0.6845	Remote Similarity	NPD1934	Approved
0.6839	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4236	Phase 3
0.6832	Remote Similarity	NPD4237	Approved
0.6831	Remote Similarity	NPD3021	Approved
0.6831	Remote Similarity	NPD3022	Approved
0.6821	Remote Similarity	NPD5327	Phase 3
0.6821	Remote Similarity	NPD4749	Approved
0.6813	Remote Similarity	NPD6005	Phase 3
0.6813	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6002	Phase 3
0.6813	Remote Similarity	NPD6004	Phase 3
0.6813	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7843	Approved
0.6805	Remote Similarity	NPD8455	Phase 2
0.68	Remote Similarity	NPD1610	Phase 2
0.6792	Remote Similarity	NPD4108	Discontinued
0.679	Remote Similarity	NPD6331	Phase 2
0.679	Remote Similarity	NPD4110	Phase 3
0.679	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5126	Approved
0.6779	Remote Similarity	NPD5125	Phase 3
0.6761	Remote Similarity	NPD2684	Approved
0.6757	Remote Similarity	NPD3091	Approved
0.6752	Remote Similarity	NPD1558	Phase 1
0.6752	Remote Similarity	NPD4060	Phase 1
0.6743	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6166	Phase 2
0.6743	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6362	Approved
0.673	Remote Similarity	NPD4536	Approved
0.673	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4538	Approved
0.673	Remote Similarity	NPD7097	Phase 1
0.6728	Remote Similarity	NPD3060	Approved
0.6725	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3787	Discontinued
0.6708	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD2801	Approved
0.6706	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6559	Discontinued
0.6702	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.669	Remote Similarity	NPD290	Approved
0.6688	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5647	Approved
0.6687	Remote Similarity	NPD5960	Phase 3
0.6687	Remote Similarity	NPD5588	Approved
0.6667	Remote Similarity	NPD6671	Approved
0.6667	Remote Similarity	NPD8651	Approved
0.6649	Remote Similarity	NPD7680	Approved
0.6647	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2238	Phase 2
0.6646	Remote Similarity	NPD2161	Phase 2
0.6644	Remote Similarity	NPD1548	Phase 1
0.663	Remote Similarity	NPD7311	Approved
0.663	Remote Similarity	NPD7312	Approved
0.663	Remote Similarity	NPD7310	Approved
0.663	Remote Similarity	NPD7313	Approved
0.6629	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD1652	Phase 2
0.6626	Remote Similarity	NPD5177	Phase 3
0.6624	Remote Similarity	NPD3145	Approved
0.6624	Remote Similarity	NPD3144	Approved
0.6608	Remote Similarity	NPD5772	Approved
0.6608	Remote Similarity	NPD5773	Approved
0.6607	Remote Similarity	NPD3687	Approved
0.6607	Remote Similarity	NPD3686	Approved
0.6604	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6355	Discontinued
0.6604	Remote Similarity	NPD5124	Phase 1
0.6593	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7309	Approved
0.659	Remote Similarity	NPD5604	Discontinued
0.6584	Remote Similarity	NPD7033	Discontinued
0.6582	Remote Similarity	NPD2674	Phase 3
0.6577	Remote Similarity	NPD5536	Phase 2
0.6573	Remote Similarity	NPD3751	Discontinued
0.6571	Remote Similarity	NPD291	Approved
0.657	Remote Similarity	NPD3817	Phase 2
0.6561	Remote Similarity	NPD4625	Phase 3
0.6561	Remote Similarity	NPD7095	Approved
0.6556	Remote Similarity	NPD3095	Discontinued
0.6554	Remote Similarity	NPD2489	Approved
0.6554	Remote Similarity	NPD27	Approved
0.6548	Remote Similarity	NPD2122	Discontinued
0.6545	Remote Similarity	NPD2677	Approved
0.6538	Remote Similarity	NPD5736	Approved
0.6538	Remote Similarity	NPD9494	Approved
0.6538	Remote Similarity	NPD4578	Approved
0.6538	Remote Similarity	NPD4577	Approved
0.6533	Remote Similarity	NPD7741	Discontinued
0.6532	Remote Similarity	NPD3882	Suspended
0.6529	Remote Similarity	NPD4380	Phase 2
0.6527	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD4123	Phase 3
0.6522	Remote Similarity	NPD4663	Approved
0.6509	Remote Similarity	NPD4210	Discontinued
0.6506	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.65	Remote Similarity	NPD230	Phase 1
0.6497	Remote Similarity	NPD2970	Approved
0.6497	Remote Similarity	NPD2969	Approved
0.6494	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3685	Discontinued
0.6488	Remote Similarity	NPD7526	Approved
0.6488	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD52	Approved
0.6486	Remote Similarity	NPD6841	Approved
0.6486	Remote Similarity	NPD7906	Approved
0.6486	Remote Similarity	NPD6842	Approved
0.6486	Remote Similarity	NPD6843	Phase 3
0.6485	Remote Similarity	NPD4628	Phase 3
0.6483	Remote Similarity	NPD556	Approved
0.6478	Remote Similarity	NPD6233	Phase 2
0.6474	Remote Similarity	NPD2563	Approved
0.6474	Remote Similarity	NPD2560	Approved
0.6474	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4005	Discontinued
0.6467	Remote Similarity	NPD1511	Approved
0.6467	Remote Similarity	NPD1774	Approved
0.6463	Remote Similarity	NPD2424	Discontinued
0.6453	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD8312	Approved
0.6448	Remote Similarity	NPD8313	Approved
0.6447	Remote Similarity	NPD4059	Approved
0.6446	Remote Similarity	NPD5241	Discontinued
0.6446	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5844	Phase 1
0.6441	Remote Similarity	NPD3051	Approved
0.6441	Remote Similarity	NPD6071	Discontinued
0.6433	Remote Similarity	NPD4678	Approved
0.6433	Remote Similarity	NPD4675	Approved
0.6429	Remote Similarity	NPD2231	Phase 2
0.6429	Remote Similarity	NPD1754	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data