NPASS Compound

Structure

CID289438 OpenBabel06191716092D 30 32 0 0 1 0 0 0 0 0999 V2000 6.1667 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 -1.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8366 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7026 -4.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5686 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5686 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8988 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2007 -0.8392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3917 -0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 8 1 0 0 0 0 2 10 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 8 1 0 0 0 0 4 19 2 0 0 0 0 5 27 1 0 0 0 0 6 18 1 0 0 0 0 6 20 1 0 0 0 0 7 18 1 0 0 0 0 7 28 1 0 0 0 0 9 10 2 0 0 0 0 9 21 1 0 0 0 0 10 29 1 0 0 0 0 11 5 1 1 0 0 0 11 12 1 0 0 0 0 11 30 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 6 0 0 0 13 14 1 0 0 0 0 13 23 1 1 0 0 0 14 16 1 0 0 0 0 14 24 1 6 0 0 0 15 17 1 0 0 0 0 15 18 1 6 0 0 0 15 25 1 0 0 0 0 16 29 1 1 0 0 0 16 30 1 0 0 0 0 17 27 1 1 0 0 0 17 28 1 0 0 0 0 18 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.13
Volume:	389.152
LogP:	-1.294
LogD:	-0.858
LogS:	-2.036
# Rotatable Bonds:	7
TPSA:	195.6
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.214
Synthetic Accessibility Score:	4.507
Fsp3:	0.611
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.562
MDCK Permeability:	2.9770057153655216e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.94
20% Bioavailability (F20%):	0.82
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.207
Plasma Protein Binding (PPB):	44.03428649902344%
Volume Distribution (VD):	0.408
Pgp-substrate:	53.97146224975586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	1.327
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.208
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.416
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.493
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.092
Respiratory Toxicity:	0.062

Download Data

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

Natural Product: NPC289438

Natural Product ID:	NPC289438
*Common Name:**	Bretschneideroside B
IUPAC Name:	4-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxybenzaldehyde
Synonyms:
Standard InCHIKey:	HNPKQZLEUUJVIJ-FQXXIRCGSA-N
Standard InCHI:	InChI=1S/C18H24O12/c19-4-8-1-2-10(9(21)3-8)29-16-14(24)13(23)12(22)11(30-16)5-27-17-15(25)18(26,6-20)7-28-17/h1-4,11-17,20-26H,5-7H2/t11-,12-,13+,14-,15+,16-,17-,18-/m1/s1
SMILES:	c1cc(c(cc1C=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@@](CO)(CO2)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223634
PubChem CID:	46938555
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:0004165] Phenolic glycosides

*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
NPO1813	Bretschneidera sinensis	Species	Akaniaceae	Eukaryota	stems	Jiujiang, Jiangxi Province, China	2008-AUG	PMID[20722446]
NPO1813	Bretschneidera sinensis	Species	Akaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1813	Bretschneidera sinensis	Species	Akaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1813	Bretschneidera sinensis	Species	Akaniaceae	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	4

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT937	Cell Line	NCI-H446	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[523672]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[523672]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[523672]
NPT937	Cell Line	NCI-H446	Homo sapiens	GI	=	38.43	%	PMID[523672]
NPT116	Cell Line	HL-60	Homo sapiens	GI	=	7.25	%	PMID[523672]
NPT393	Cell Line	HCT-116	Homo sapiens	GI	=	0.0	%	PMID[523672]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[523672]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	0.0	%	PMID[523672]

☑ 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 NPC289438 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	368
0.1-0.2	1521
0.2-0.3	3752
0.3-0.4	8920
0.4-0.5	9589
0.5-0.6	4580
0.6-0.7	7447
0.7-0.8	5950
0.8-0.85	495
0.85-0.9	67
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9724	High Similarity	NPC227980
0.9324	High Similarity	NPC205054
0.9205	High Similarity	NPC194095
0.9205	High Similarity	NPC191046
0.9205	High Similarity	NPC327032
0.9184	High Similarity	NPC473867
0.915	High Similarity	NPC226759
0.9085	High Similarity	NPC471405
0.9073	High Similarity	NPC134905
0.9073	High Similarity	NPC36130
0.9026	High Similarity	NPC133984
0.902	High Similarity	NPC10205
0.9013	High Similarity	NPC310661
0.9013	High Similarity	NPC157898
0.9013	High Similarity	NPC105827
0.8968	High Similarity	NPC289811
0.8968	High Similarity	NPC160780
0.8926	High Similarity	NPC9370
0.8926	High Similarity	NPC287495
0.891	High Similarity	NPC239966
0.891	High Similarity	NPC203020
0.8903	High Similarity	NPC1913
0.8889	High Similarity	NPC137813
0.8889	High Similarity	NPC212729
0.8874	High Similarity	NPC111785
0.8854	High Similarity	NPC472859
0.8854	High Similarity	NPC311803
0.8854	High Similarity	NPC25389
0.8851	High Similarity	NPC242756
0.8846	High Similarity	NPC74319
0.8846	High Similarity	NPC287872
0.882	High Similarity	NPC212748
0.8808	High Similarity	NPC472969
0.8797	High Similarity	NPC33298
0.8797	High Similarity	NPC41009
0.8797	High Similarity	NPC285108
0.8797	High Similarity	NPC476011
0.879	High Similarity	NPC119125
0.879	High Similarity	NPC166277
0.879	High Similarity	NPC289346
0.8782	High Similarity	NPC472860
0.8759	High Similarity	NPC55040
0.875	High Similarity	NPC98809
0.875	High Similarity	NPC476394
0.8742	High Similarity	NPC88043
0.8707	High Similarity	NPC100389
0.8707	High Similarity	NPC226005
0.8704	High Similarity	NPC72249
0.8699	High Similarity	NPC186418
0.8688	High Similarity	NPC180586
0.8688	High Similarity	NPC165720
0.8679	High Similarity	NPC4013
0.8679	High Similarity	NPC148273
0.8679	High Similarity	NPC90905
0.8659	High Similarity	NPC84482
0.8659	High Similarity	NPC169645
0.8654	High Similarity	NPC180901
0.8654	High Similarity	NPC300757
0.865	High Similarity	NPC235575
0.8649	High Similarity	NPC202700
0.8645	High Similarity	NPC44730
0.8634	High Similarity	NPC130730
0.8634	High Similarity	NPC301910
0.8627	High Similarity	NPC478242
0.8627	High Similarity	NPC75945
0.8609	High Similarity	NPC108455
0.8598	High Similarity	NPC316539
0.8591	High Similarity	NPC79908
0.8591	High Similarity	NPC80098
0.8581	High Similarity	NPC75695
0.8581	High Similarity	NPC203664
0.858	High Similarity	NPC149244
0.858	High Similarity	NPC45400
0.858	High Similarity	NPC48640
0.858	High Similarity	NPC116745
0.8571	High Similarity	NPC37468
0.8571	High Similarity	NPC294470
0.8571	High Similarity	NPC157554
0.8571	High Similarity	NPC104172
0.8571	High Similarity	NPC88886
0.8571	High Similarity	NPC475738
0.8562	High Similarity	NPC22324
0.8553	High Similarity	NPC291153
0.8553	High Similarity	NPC474936
0.8552	High Similarity	NPC252833
0.8544	High Similarity	NPC286919
0.8544	High Similarity	NPC475663
0.8543	High Similarity	NPC110063
0.8543	High Similarity	NPC229036
0.8543	High Similarity	NPC473090
0.8537	High Similarity	NPC261254
0.8533	High Similarity	NPC157816
0.8528	High Similarity	NPC197708
0.8528	High Similarity	NPC658
0.8528	High Similarity	NPC229687
0.8526	High Similarity	NPC183536
0.8526	High Similarity	NPC245615
0.8526	High Similarity	NPC299706
0.8526	High Similarity	NPC131121
0.8526	High Similarity	NPC61604
0.8526	High Similarity	NPC34965
0.8526	High Similarity	NPC115466
0.8523	High Similarity	NPC210478
0.8519	High Similarity	NPC254306
0.8519	High Similarity	NPC282551
0.8516	High Similarity	NPC140151
0.8509	High Similarity	NPC168822
0.8509	High Similarity	NPC94777
0.8509	High Similarity	NPC191306
0.8509	High Similarity	NPC227297
0.8509	High Similarity	NPC270335
0.8506	High Similarity	NPC92117
0.8494	Intermediate Similarity	NPC473713
0.8493	Intermediate Similarity	NPC6836
0.8493	Intermediate Similarity	NPC25821
0.8491	Intermediate Similarity	NPC76211
0.8491	Intermediate Similarity	NPC469384
0.8481	Intermediate Similarity	NPC163635
0.8477	Intermediate Similarity	NPC478239
0.8476	Intermediate Similarity	NPC471416
0.8476	Intermediate Similarity	NPC149011
0.8476	Intermediate Similarity	NPC204937
0.8476	Intermediate Similarity	NPC34287
0.8467	Intermediate Similarity	NPC326065
0.8467	Intermediate Similarity	NPC186406
0.8466	Intermediate Similarity	NPC45618
0.8466	Intermediate Similarity	NPC229729
0.8466	Intermediate Similarity	NPC146792
0.8466	Intermediate Similarity	NPC58716
0.8462	Intermediate Similarity	NPC99772
0.8457	Intermediate Similarity	NPC311830
0.8457	Intermediate Similarity	NPC22832
0.8456	Intermediate Similarity	NPC220942
0.8452	Intermediate Similarity	NPC473091
0.8447	Intermediate Similarity	NPC77660
0.8447	Intermediate Similarity	NPC206815
0.8447	Intermediate Similarity	NPC300537
0.8447	Intermediate Similarity	NPC127782
0.8447	Intermediate Similarity	NPC246024
0.8447	Intermediate Similarity	NPC189142
0.8446	Intermediate Similarity	NPC470572
0.8442	Intermediate Similarity	NPC116229
0.8442	Intermediate Similarity	NPC248257
0.8442	Intermediate Similarity	NPC120621
0.8438	Intermediate Similarity	NPC138993
0.8438	Intermediate Similarity	NPC44507
0.8435	Intermediate Similarity	NPC144662
0.8435	Intermediate Similarity	NPC45404
0.8435	Intermediate Similarity	NPC470881
0.8434	Intermediate Similarity	NPC469354
0.8434	Intermediate Similarity	NPC469438
0.8434	Intermediate Similarity	NPC472607
0.8431	Intermediate Similarity	NPC474044
0.8431	Intermediate Similarity	NPC98356
0.8428	Intermediate Similarity	NPC40920
0.8428	Intermediate Similarity	NPC104275
0.8428	Intermediate Similarity	NPC4747
0.8428	Intermediate Similarity	NPC223335
0.8425	Intermediate Similarity	NPC473924
0.8424	Intermediate Similarity	NPC205076
0.8424	Intermediate Similarity	NPC48773
0.8424	Intermediate Similarity	NPC245452
0.8424	Intermediate Similarity	NPC307518
0.8424	Intermediate Similarity	NPC102851
0.8424	Intermediate Similarity	NPC5786
0.8421	Intermediate Similarity	NPC232228
0.8421	Intermediate Similarity	NPC297342
0.8415	Intermediate Similarity	NPC469931
0.8415	Intermediate Similarity	NPC226294
0.8415	Intermediate Similarity	NPC45638
0.8415	Intermediate Similarity	NPC475942
0.8415	Intermediate Similarity	NPC58053
0.8415	Intermediate Similarity	NPC186807
0.8415	Intermediate Similarity	NPC201292
0.8415	Intermediate Similarity	NPC21956
0.8415	Intermediate Similarity	NPC471457
0.8415	Intermediate Similarity	NPC170675
0.8415	Intermediate Similarity	NPC93337
0.8415	Intermediate Similarity	NPC476771
0.8415	Intermediate Similarity	NPC95421
0.8415	Intermediate Similarity	NPC198125
0.8415	Intermediate Similarity	NPC105025
0.8415	Intermediate Similarity	NPC112755
0.8414	Intermediate Similarity	NPC298268
0.8408	Intermediate Similarity	NPC215811
0.8405	Intermediate Similarity	NPC255615
0.8405	Intermediate Similarity	NPC197285
0.8405	Intermediate Similarity	NPC236934
0.8405	Intermediate Similarity	NPC67037
0.8405	Intermediate Similarity	NPC5778
0.8405	Intermediate Similarity	NPC99957
0.8405	Intermediate Similarity	NPC21100
0.8405	Intermediate Similarity	NPC181616
0.8397	Intermediate Similarity	NPC243891
0.8395	Intermediate Similarity	NPC284960
0.8395	Intermediate Similarity	NPC243930
0.8395	Intermediate Similarity	NPC470178
0.8395	Intermediate Similarity	NPC100425
0.8395	Intermediate Similarity	NPC19709
0.8395	Intermediate Similarity	NPC88023

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 NPC289438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	814
0.2-0.3	1934
0.3-0.4	2724
0.4-0.5	1882
0.5-0.6	1007
0.6-0.7	404
0.7-0.8	72
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD3818	Discontinued
0.8373	Intermediate Similarity	NPD7685	Pre-registration
0.8303	Intermediate Similarity	NPD7054	Approved
0.8253	Intermediate Similarity	NPD7074	Phase 3
0.8253	Intermediate Similarity	NPD7472	Approved
0.8214	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD9494	Approved
0.8137	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6797	Phase 2
0.8086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7251	Discontinued
0.8038	Intermediate Similarity	NPD1653	Approved
0.8025	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD7808	Phase 3
0.795	Intermediate Similarity	NPD1934	Approved
0.7941	Intermediate Similarity	NPD6559	Discontinued
0.7898	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6190	Approved
0.7798	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6166	Phase 2
0.7798	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2801	Approved
0.7791	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD230	Phase 1
0.7759	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7266	Discontinued
0.7707	Intermediate Similarity	NPD4628	Phase 3
0.7674	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6234	Discontinued
0.7602	Intermediate Similarity	NPD7228	Approved
0.7576	Intermediate Similarity	NPD1465	Phase 2
0.7562	Intermediate Similarity	NPD1511	Approved
0.7558	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3817	Phase 2
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.7515	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD4380	Phase 2
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD4966	Approved
0.7469	Intermediate Similarity	NPD1512	Approved
0.7457	Intermediate Similarity	NPD5844	Phase 1
0.7456	Intermediate Similarity	NPD5494	Approved
0.745	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1091	Approved
0.7419	Intermediate Similarity	NPD447	Suspended
0.7347	Intermediate Similarity	NPD1357	Approved
0.7345	Intermediate Similarity	NPD8313	Approved
0.7345	Intermediate Similarity	NPD8312	Approved
0.7337	Intermediate Similarity	NPD7075	Discontinued
0.7326	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3751	Discontinued
0.7273	Intermediate Similarity	NPD3027	Phase 3
0.7262	Intermediate Similarity	NPD8455	Phase 2
0.7253	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1549	Phase 2
0.7244	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1613	Approved
0.7238	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD5353	Approved
0.7219	Intermediate Similarity	NPD5402	Approved
0.7209	Intermediate Similarity	NPD1247	Approved
0.72	Intermediate Similarity	NPD3705	Approved
0.7197	Intermediate Similarity	NPD1933	Approved
0.7193	Intermediate Similarity	NPD919	Approved
0.7188	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6232	Discontinued
0.7168	Intermediate Similarity	NPD3787	Discontinued
0.7162	Intermediate Similarity	NPD9545	Approved
0.716	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD9269	Phase 2
0.7143	Intermediate Similarity	NPD6386	Approved
0.7143	Intermediate Similarity	NPD6385	Approved
0.7135	Intermediate Similarity	NPD7240	Approved
0.7134	Intermediate Similarity	NPD6799	Approved
0.7125	Intermediate Similarity	NPD1551	Phase 2
0.7124	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6801	Discontinued
0.7099	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7819	Suspended
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7473	Discontinued
0.7029	Intermediate Similarity	NPD3926	Phase 2
0.7015	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.7006	Intermediate Similarity	NPD3764	Approved
0.7006	Intermediate Similarity	NPD5403	Approved
0.6994	Remote Similarity	NPD6674	Discontinued
0.6988	Remote Similarity	NPD2532	Approved
0.6988	Remote Similarity	NPD2533	Approved
0.6988	Remote Similarity	NPD2534	Approved
0.6988	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6781	Approved
0.6984	Remote Similarity	NPD6777	Approved
0.6984	Remote Similarity	NPD6779	Approved
0.6984	Remote Similarity	NPD6776	Approved
0.6984	Remote Similarity	NPD6782	Approved
0.6984	Remote Similarity	NPD6780	Approved
0.6984	Remote Similarity	NPD6778	Approved
0.698	Remote Similarity	NPD5536	Phase 2
0.6957	Remote Similarity	NPD1510	Phase 2
0.6951	Remote Similarity	NPD4110	Phase 3
0.6951	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7039	Approved
0.6944	Remote Similarity	NPD7038	Approved
0.6941	Remote Similarity	NPD7411	Suspended
0.6936	Remote Similarity	NPD3749	Approved
0.6933	Remote Similarity	NPD2424	Discontinued
0.6933	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD824	Approved
0.6923	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD943	Approved
0.6914	Remote Similarity	NPD2796	Approved
0.6914	Remote Similarity	NPD2935	Discontinued
0.691	Remote Similarity	NPD2163	Approved
0.6905	Remote Similarity	NPD920	Approved
0.6899	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD9268	Approved
0.6886	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5401	Approved
0.6886	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7028	Phase 2
0.6882	Remote Similarity	NPD6599	Discontinued
0.6875	Remote Similarity	NPD7435	Discontinued
0.6871	Remote Similarity	NPD2344	Approved
0.6867	Remote Similarity	NPD5058	Phase 3
0.686	Remote Similarity	NPD5761	Phase 2
0.686	Remote Similarity	NPD5760	Phase 2
0.6855	Remote Similarity	NPD6233	Phase 2
0.6852	Remote Similarity	NPD7033	Discontinued
0.6848	Remote Similarity	NPD3750	Approved
0.6842	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD5242	Approved
0.6832	Remote Similarity	NPD6653	Approved
0.6826	Remote Similarity	NPD4357	Discontinued
0.6824	Remote Similarity	NPD7458	Discontinued
0.6824	Remote Similarity	NPD3455	Phase 2
0.6818	Remote Similarity	NPD1608	Approved
0.6818	Remote Similarity	NPD6959	Discontinued
0.6813	Remote Similarity	NPD1240	Approved
0.6803	Remote Similarity	NPD228	Approved
0.6802	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7783	Phase 2
0.6795	Remote Similarity	NPD1203	Approved
0.679	Remote Similarity	NPD7097	Phase 1
0.6788	Remote Similarity	NPD7698	Approved
0.6788	Remote Similarity	NPD7696	Phase 3
0.6788	Remote Similarity	NPD2800	Approved
0.6788	Remote Similarity	NPD7697	Approved
0.6788	Remote Similarity	NPD7680	Approved
0.6786	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3146	Approved
0.6784	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6355	Discontinued
0.6769	Remote Similarity	NPD7584	Approved
0.6768	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2978	Approved
0.6763	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2977	Approved
0.6753	Remote Similarity	NPD7871	Phase 2
0.6753	Remote Similarity	NPD7870	Phase 2
0.6752	Remote Similarity	NPD5647	Approved
0.6748	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6273	Approved
0.6739	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6823	Phase 2
0.6735	Remote Similarity	NPD7701	Phase 2
0.6735	Remote Similarity	NPD7585	Approved
0.6733	Remote Similarity	NPD4665	Approved
0.6733	Remote Similarity	NPD4111	Phase 1
0.6728	Remote Similarity	NPD2492	Phase 1
0.6728	Remote Similarity	NPD1607	Approved
0.6725	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3226	Approved
0.672	Remote Similarity	NPD6534	Approved
0.672	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6535	Approved
0.6718	Remote Similarity	NPD7999	Approved
0.6711	Remote Similarity	NPD1241	Discontinued
0.671	Remote Similarity	NPD9717	Approved
0.6709	Remote Similarity	NPD2861	Phase 2
0.6708	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2309	Approved
0.6707	Remote Similarity	NPD3887	Approved
0.6707	Remote Similarity	NPD2354	Approved
0.6704	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD8151	Discontinued
0.6687	Remote Similarity	NPD6798	Discontinued
0.6684	Remote Similarity	NPD7583	Approved
0.6667	Remote Similarity	NPD1375	Discontinued
0.6667	Remote Similarity	NPD1899	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