NPASS Compound

Structure

NPC475824 OpenBabel07101719252D 34 38 0 0 1 0 0 0 0 0999 V2000 3.9801 0.2990 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 4.6492 1.0421 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 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 -5.8108 -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 5.6273 0.8342 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 -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 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 3 1 0 0 0 0 1 11 2 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 12 1 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 7 30 1 0 0 0 0 8 31 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 12 26 1 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 9 1 1 0 0 0 14 16 1 0 0 0 0 14 32 1 0 0 0 0 15 21 1 0 0 0 0 15 23 1 6 0 0 0 16 17 1 0 0 0 0 16 27 1 6 0 0 0 17 18 1 0 0 0 0 17 28 1 1 0 0 0 18 22 1 0 0 0 0 18 29 1 6 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 23 1 6 0 0 0 20 34 1 0 0 0 0 21 31 1 0 0 0 0 21 33 1 1 0 0 0 22 32 1 0 0 0 0 22 33 1 1 0 0 0 23 10 1 1 0 0 0 23 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.16
Volume:	447.092
LogP:	0.39
LogD:	0.244
LogS:	-2.442
# Rotatable Bonds:	7
TPSA:	170.83
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.205
Synthetic Accessibility Score:	5.163
Fsp3:	0.565
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.104
MDCK Permeability:	6.575594306923449e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.543
Human Intestinal Absorption (HIA):	0.889
20% Bioavailability (F20%):	0.566
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	60.1287727355957%
Volume Distribution (VD):	0.406
Pgp-substrate:	33.713218688964844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	1.781
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.183
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.31
Carcinogencity:	0.945
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC475824

Natural Product ID:	NPC475824
*Common Name:**	(-)-Specioside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(1aR,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-6-[(E)-2-(4-hydroxyphenyl)ethenoxy]-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:	(-)-Specioside
Standard InCHIKey:	AWKRVVGAVDYMNU-XKVKTCGNSA-N
Standard InCHI:	InChI=1S/C23H28O11/c24-9-14-16(27)17(28)18(29)22(32-14)33-21-15-13(6-8-31-21)19(20-23(15,10-25)34-20)30-7-5-11-1-3-12(26)4-2-11/h1-8,13-22,24-29H,9-10H2/b7-5+/t13-,14-,15-,16-,17+,18-,19+,20+,21+,22+,23+/m1/s1
SMILES:	C1=COC(C2C1C(C3C2(O3)CO)OC=CC4=CC=C(C=C4)O)OC5C(C(C(C(O5)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516849
PubChem CID:	44566579
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	=	160.85	uM	PMID[460119]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	79880.0	nM	PMID[460119]

☑ 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 NPC475824 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	396
0.1-0.2	1315
0.2-0.3	3324
0.3-0.4	8907
0.4-0.5	10930
0.5-0.6	12605
0.6-0.7	4466
0.7-0.8	690
0.8-0.85	40
0.85-0.9	20
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9323	High Similarity	NPC46644
0.903	High Similarity	NPC49597
0.8986	High Similarity	NPC474234
0.8921	High Similarity	NPC18789
0.8841	High Similarity	NPC478240
0.8705	High Similarity	NPC184464
0.8705	High Similarity	NPC251062
0.8633	High Similarity	NPC237872
0.8633	High Similarity	NPC88754
0.8633	High Similarity	NPC302286
0.8633	High Similarity	NPC116104
0.8633	High Similarity	NPC263397
0.8623	High Similarity	NPC7518
0.8623	High Similarity	NPC154262
0.8623	High Similarity	NPC159387
0.8623	High Similarity	NPC137501
0.8611	High Similarity	NPC194705
0.8552	High Similarity	NPC89693
0.8552	High Similarity	NPC229548
0.8552	High Similarity	NPC478241
0.8516	High Similarity	NPC476445
0.8516	High Similarity	NPC469548
0.8516	High Similarity	NPC476448
0.8507	High Similarity	NPC254819
0.85	High Similarity	NPC186296
0.8462	Intermediate Similarity	NPC232454
0.8462	Intermediate Similarity	NPC178449
0.8462	Intermediate Similarity	NPC470907
0.8451	Intermediate Similarity	NPC37838
0.845	Intermediate Similarity	NPC469686
0.8438	Intermediate Similarity	NPC469702
0.8438	Intermediate Similarity	NPC282409
0.8413	Intermediate Similarity	NPC148055
0.8403	Intermediate Similarity	NPC478236
0.84	Intermediate Similarity	NPC157338
0.8385	Intermediate Similarity	NPC471067
0.8378	Intermediate Similarity	NPC475378
0.8372	Intermediate Similarity	NPC469703
0.8372	Intermediate Similarity	NPC201402
0.8372	Intermediate Similarity	NPC469704
0.8372	Intermediate Similarity	NPC160854
0.8346	Intermediate Similarity	NPC175333
0.8345	Intermediate Similarity	NPC117346
0.8345	Intermediate Similarity	NPC240592
0.8345	Intermediate Similarity	NPC147224
0.8333	Intermediate Similarity	NPC90318
0.8308	Intermediate Similarity	NPC55608
0.8299	Intermediate Similarity	NPC229354
0.8288	Intermediate Similarity	NPC478249
0.8288	Intermediate Similarity	NPC269914
0.8276	Intermediate Similarity	NPC96599
0.8276	Intermediate Similarity	NPC478234
0.8268	Intermediate Similarity	NPC175771
0.8255	Intermediate Similarity	NPC478248
0.8254	Intermediate Similarity	NPC313193
0.8243	Intermediate Similarity	NPC478232
0.8212	Intermediate Similarity	NPC478265
0.8212	Intermediate Similarity	NPC138993
0.8209	Intermediate Similarity	NPC469687
0.8207	Intermediate Similarity	NPC308178
0.8182	Intermediate Similarity	NPC202391
0.8182	Intermediate Similarity	NPC296659
0.8168	Intermediate Similarity	NPC266045
0.8163	Intermediate Similarity	NPC289021
0.8163	Intermediate Similarity	NPC158546
0.8134	Intermediate Similarity	NPC267733
0.8134	Intermediate Similarity	NPC276047
0.8085	Intermediate Similarity	NPC31745
0.8085	Intermediate Similarity	NPC220936
0.8074	Intermediate Similarity	NPC108659
0.8074	Intermediate Similarity	NPC264900
0.8074	Intermediate Similarity	NPC231607
0.8074	Intermediate Similarity	NPC79715
0.8015	Intermediate Similarity	NPC148982
0.8	Intermediate Similarity	NPC252114
0.8	Intermediate Similarity	NPC94179
0.7987	Intermediate Similarity	NPC478235
0.7986	Intermediate Similarity	NPC6836
0.7985	Intermediate Similarity	NPC287429
0.7985	Intermediate Similarity	NPC145287
0.7971	Intermediate Similarity	NPC478255
0.797	Intermediate Similarity	NPC52097
0.797	Intermediate Similarity	NPC476142
0.7956	Intermediate Similarity	NPC184092
0.7956	Intermediate Similarity	NPC253595
0.7955	Intermediate Similarity	NPC469412
0.7955	Intermediate Similarity	NPC269242
0.7955	Intermediate Similarity	NPC198734
0.7949	Intermediate Similarity	NPC130730
0.7949	Intermediate Similarity	NPC301910
0.7947	Intermediate Similarity	NPC475484
0.7943	Intermediate Similarity	NPC472132
0.7941	Intermediate Similarity	NPC106677
0.7941	Intermediate Similarity	NPC288416
0.7931	Intermediate Similarity	NPC473281
0.7931	Intermediate Similarity	NPC77922
0.7929	Intermediate Similarity	NPC470881
0.7929	Intermediate Similarity	NPC169398
0.7926	Intermediate Similarity	NPC470510
0.7926	Intermediate Similarity	NPC126991
0.7926	Intermediate Similarity	NPC83218
0.7919	Intermediate Similarity	NPC475379
0.7914	Intermediate Similarity	NPC252833
0.7902	Intermediate Similarity	NPC164743
0.7895	Intermediate Similarity	NPC11724
0.7895	Intermediate Similarity	NPC478266
0.7887	Intermediate Similarity	NPC304152
0.7883	Intermediate Similarity	NPC225307
0.7877	Intermediate Similarity	NPC475528
0.7872	Intermediate Similarity	NPC79957
0.7871	Intermediate Similarity	NPC206815
0.7868	Intermediate Similarity	NPC471157
0.7862	Intermediate Similarity	NPC293154
0.7857	Intermediate Similarity	NPC164172
0.7857	Intermediate Similarity	NPC25821
0.7847	Intermediate Similarity	NPC472711
0.7842	Intermediate Similarity	NPC248307
0.7842	Intermediate Similarity	NPC65942
0.7826	Intermediate Similarity	NPC307110
0.7826	Intermediate Similarity	NPC469549
0.7823	Intermediate Similarity	NPC143246
0.7823	Intermediate Similarity	NPC474268
0.7823	Intermediate Similarity	NPC119773
0.7823	Intermediate Similarity	NPC475539
0.782	Intermediate Similarity	NPC476872
0.781	Intermediate Similarity	NPC471882
0.781	Intermediate Similarity	NPC156692
0.781	Intermediate Similarity	NPC35288
0.781	Intermediate Similarity	NPC45224
0.781	Intermediate Similarity	NPC471881
0.781	Intermediate Similarity	NPC173150
0.7808	Intermediate Similarity	NPC470235
0.7808	Intermediate Similarity	NPC84181
0.7808	Intermediate Similarity	NPC283995
0.7808	Intermediate Similarity	NPC194938
0.7808	Intermediate Similarity	NPC63304
0.7808	Intermediate Similarity	NPC129417
0.7801	Intermediate Similarity	NPC35731
0.7793	Intermediate Similarity	NPC472353
0.7786	Intermediate Similarity	NPC303422
0.7786	Intermediate Similarity	NPC254275
0.7786	Intermediate Similarity	NPC26080
0.7786	Intermediate Similarity	NPC471066
0.7786	Intermediate Similarity	NPC85799
0.7786	Intermediate Similarity	NPC471095
0.7786	Intermediate Similarity	NPC473924
0.7786	Intermediate Similarity	NPC165686
0.7778	Intermediate Similarity	NPC212176
0.777	Intermediate Similarity	NPC470122
0.777	Intermediate Similarity	NPC17968
0.777	Intermediate Similarity	NPC469705
0.7762	Intermediate Similarity	NPC469364
0.7762	Intermediate Similarity	NPC65262
0.7762	Intermediate Similarity	NPC101686
0.7756	Intermediate Similarity	NPC476011
0.7754	Intermediate Similarity	NPC158673
0.7746	Intermediate Similarity	NPC476870
0.7744	Intermediate Similarity	NPC469708
0.7744	Intermediate Similarity	NPC60589
0.774	Intermediate Similarity	NPC46092
0.774	Intermediate Similarity	NPC475213
0.774	Intermediate Similarity	NPC477898
0.774	Intermediate Similarity	NPC470950
0.774	Intermediate Similarity	NPC152796
0.774	Intermediate Similarity	NPC185307
0.7737	Intermediate Similarity	NPC61181
0.7733	Intermediate Similarity	NPC35097
0.773	Intermediate Similarity	NPC254398
0.773	Intermediate Similarity	NPC115022
0.773	Intermediate Similarity	NPC294166
0.7718	Intermediate Similarity	NPC120728
0.7714	Intermediate Similarity	NPC476407
0.7714	Intermediate Similarity	NPC225384
0.7714	Intermediate Similarity	NPC46137
0.7714	Intermediate Similarity	NPC246869
0.7714	Intermediate Similarity	NPC219677
0.7714	Intermediate Similarity	NPC121376
0.7714	Intermediate Similarity	NPC138777
0.7714	Intermediate Similarity	NPC9912
0.7714	Intermediate Similarity	NPC235294
0.771	Intermediate Similarity	NPC473556
0.771	Intermediate Similarity	NPC301651
0.7708	Intermediate Similarity	NPC321638
0.7708	Intermediate Similarity	NPC328273
0.7708	Intermediate Similarity	NPC171134
0.7708	Intermediate Similarity	NPC321184
0.7708	Intermediate Similarity	NPC156376
0.7703	Intermediate Similarity	NPC112861
0.7703	Intermediate Similarity	NPC473147
0.7698	Intermediate Similarity	NPC248355
0.7698	Intermediate Similarity	NPC477294
0.7698	Intermediate Similarity	NPC229784
0.7698	Intermediate Similarity	NPC477293
0.7698	Intermediate Similarity	NPC295970
0.7698	Intermediate Similarity	NPC166040
0.7692	Intermediate Similarity	NPC177035
0.7692	Intermediate Similarity	NPC199459
0.7692	Intermediate Similarity	NPC52277
0.7687	Intermediate Similarity	NPC96447
0.7681	Intermediate Similarity	NPC103533

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 NPC475824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	744
0.2-0.3	1870
0.3-0.4	3187
0.4-0.5	1904
0.5-0.6	1018
0.6-0.7	126
0.7-0.8	6
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
0.7702	Intermediate Similarity	NPD7685	Pre-registration
0.7664	Intermediate Similarity	NPD3094	Phase 2
0.763	Intermediate Similarity	NPD1091	Approved
0.7466	Intermediate Similarity	NPD7266	Discontinued
0.7372	Intermediate Similarity	NPD3092	Approved
0.7183	Intermediate Similarity	NPD2861	Phase 2
0.7097	Intermediate Similarity	NPD1653	Approved
0.708	Intermediate Similarity	NPD3091	Approved
0.6993	Remote Similarity	NPD5058	Phase 3
0.6978	Remote Similarity	NPD5126	Approved
0.6978	Remote Similarity	NPD5125	Phase 3
0.6959	Remote Similarity	NPD6653	Approved
0.6892	Remote Similarity	NPD5735	Approved
0.6879	Remote Similarity	NPD3705	Approved
0.6857	Remote Similarity	NPD3095	Discontinued
0.6852	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3027	Phase 3
0.6828	Remote Similarity	NPD5736	Approved
0.6824	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3620	Phase 2
0.6824	Remote Similarity	NPD1613	Approved
0.6824	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6674	Discontinued
0.6786	Remote Similarity	NPD1357	Approved
0.6781	Remote Similarity	NPD4908	Phase 1
0.6776	Remote Similarity	NPD5763	Approved
0.6776	Remote Similarity	NPD5762	Approved
0.677	Remote Similarity	NPD8455	Phase 2
0.6761	Remote Similarity	NPD1610	Phase 2
0.6744	Remote Similarity	NPD3020	Approved
0.6739	Remote Similarity	NPD7157	Approved
0.6738	Remote Similarity	NPD4059	Approved
0.6714	Remote Similarity	NPD7741	Discontinued
0.671	Remote Similarity	NPD6190	Approved
0.6689	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3021	Approved
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD3022	Approved
0.6645	Remote Similarity	NPD5960	Phase 3
0.6645	Remote Similarity	NPD5588	Approved
0.6644	Remote Similarity	NPD6663	Approved
0.6644	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7843	Approved
0.6627	Remote Similarity	NPD7199	Phase 2
0.6627	Remote Similarity	NPD7228	Approved
0.6606	Remote Similarity	NPD6234	Discontinued
0.6605	Remote Similarity	NPD37	Approved
0.66	Remote Similarity	NPD4140	Approved
0.6596	Remote Similarity	NPD1548	Phase 1
0.6593	Remote Similarity	NPD2684	Approved
0.6585	Remote Similarity	NPD4967	Phase 2
0.6585	Remote Similarity	NPD4966	Approved
0.6585	Remote Similarity	NPD4965	Approved
0.6579	Remote Similarity	NPD4538	Approved
0.6579	Remote Similarity	NPD4536	Approved
0.6579	Remote Similarity	NPD7097	Phase 1
0.6579	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6362	Approved
0.6562	Remote Similarity	NPD2933	Approved
0.6562	Remote Similarity	NPD2934	Approved
0.6554	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5647	Approved
0.6531	Remote Similarity	NPD4624	Approved
0.6529	Remote Similarity	NPD3818	Discontinued
0.6519	Remote Similarity	NPD290	Approved
0.6513	Remote Similarity	NPD6353	Approved
0.6512	Remote Similarity	NPD2860	Approved
0.6512	Remote Similarity	NPD2859	Approved
0.6507	Remote Similarity	NPD8651	Approved
0.6503	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7054	Approved
0.6491	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4380	Phase 2
0.6474	Remote Similarity	NPD1652	Phase 2
0.6474	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7472	Approved
0.645	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD969	Suspended
0.6447	Remote Similarity	NPD5124	Phase 1
0.6447	Remote Similarity	NPD6355	Discontinued
0.6447	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6685	Approved
0.6439	Remote Similarity	NPD1242	Phase 1
0.6438	Remote Similarity	NPD4749	Approved
0.6438	Remote Similarity	NPD5327	Phase 3
0.6434	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4108	Discontinued
0.6429	Remote Similarity	NPD7033	Discontinued
0.642	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD6797	Phase 2
0.6391	Remote Similarity	NPD940	Approved
0.6391	Remote Similarity	NPD3787	Discontinued
0.6391	Remote Similarity	NPD846	Approved
0.6382	Remote Similarity	NPD4060	Phase 1
0.638	Remote Similarity	NPD7028	Phase 2
0.6379	Remote Similarity	NPD6559	Discontinued
0.6379	Remote Similarity	NPD7251	Discontinued
0.6358	Remote Similarity	NPD7074	Phase 3
0.6351	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD4103	Phase 2
0.6346	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD7808	Phase 3
0.6343	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5765	Approved
0.634	Remote Similarity	NPD4340	Discontinued
0.6331	Remote Similarity	NPD6912	Phase 3
0.6331	Remote Similarity	NPD228	Approved
0.6329	Remote Similarity	NPD4628	Phase 3
0.6327	Remote Similarity	NPD4659	Approved
0.6327	Remote Similarity	NPD3685	Discontinued
0.6324	Remote Similarity	NPD968	Approved
0.6316	Remote Similarity	NPD6233	Phase 2
0.6312	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD2424	Discontinued
0.6304	Remote Similarity	NPD4750	Phase 3
0.6304	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7240	Approved
0.6276	Remote Similarity	NPD9381	Approved
0.6276	Remote Similarity	NPD9384	Approved
0.6276	Remote Similarity	NPD3019	Approved
0.6276	Remote Similarity	NPD2932	Approved
0.6276	Remote Similarity	NPD5846	Approved
0.6276	Remote Similarity	NPD6516	Phase 2
0.6275	Remote Similarity	NPD2238	Phase 2
0.6273	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD6671	Approved
0.6265	Remote Similarity	NPD2977	Approved
0.6265	Remote Similarity	NPD2978	Approved
0.625	Remote Similarity	NPD3122	Phase 3
0.625	Remote Similarity	NPD3764	Approved
0.6243	Remote Similarity	NPD3751	Discontinued
0.6242	Remote Similarity	NPD1375	Discontinued
0.6241	Remote Similarity	NPD2228	Approved
0.6241	Remote Similarity	NPD2229	Approved
0.6241	Remote Similarity	NPD2234	Approved
0.6241	Remote Similarity	NPD5283	Phase 1
0.624	Remote Similarity	NPD111	Approved
0.6218	Remote Similarity	NPD7743	Approved
0.6218	Remote Similarity	NPD7742	Approved
0.6215	Remote Similarity	NPD8312	Approved
0.6215	Remote Similarity	NPD8313	Approved
0.6209	Remote Similarity	NPD6405	Approved
0.6209	Remote Similarity	NPD6407	Approved
0.619	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.619	Remote Similarity	NPD422	Phase 1
0.619	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7095	Approved
0.6184	Remote Similarity	NPD4625	Phase 3
0.6184	Remote Similarity	NPD3180	Approved
0.6184	Remote Similarity	NPD3179	Approved
0.6173	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD3062	Approved
0.6169	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD3059	Approved
0.6169	Remote Similarity	NPD3061	Approved
0.6159	Remote Similarity	NPD6406	Approved
0.6159	Remote Similarity	NPD1358	Approved
0.6149	Remote Similarity	NPD2231	Phase 2
0.6149	Remote Similarity	NPD2235	Phase 2
0.6149	Remote Similarity	NPD7799	Discontinued
0.6144	Remote Similarity	NPD6798	Discontinued
0.6143	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.614	Remote Similarity	NPD8127	Discontinued
0.6138	Remote Similarity	NPD9545	Approved
0.6135	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3657	Discovery
0.6125	Remote Similarity	NPD3892	Phase 2
0.6125	Remote Similarity	NPD4535	Phase 3
0.6107	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD845	Approved
0.6107	Remote Similarity	NPD2982	Phase 2
0.6107	Remote Similarity	NPD9622	Approved
0.6107	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD2983	Phase 2
0.6101	Remote Similarity	NPD5958	Discontinued
0.6095	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.609	Remote Similarity	NPD5314	Approved
0.609	Remote Similarity	NPD288	Approved
0.6087	Remote Similarity	NPD2677	Approved
0.6087	Remote Similarity	NPD3134	Approved
0.6074	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD3028	Approved
0.6069	Remote Similarity	NPD16	Approved
0.6069	Remote Similarity	NPD856	Approved
0.6066	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD4237	Approved
0.6062	Remote Similarity	NPD4236	Phase 3
0.6059	Remote Similarity	NPD7975	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