NPASS Compound

Structure

NPC80098 OpenBabel07101719512D 32 34 0 0 1 0 0 0 0 0999 V2000 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 5.1962 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 6.0622 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 7 2 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 4 8 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 17 1 0 0 0 0 8 29 1 0 0 0 0 9 5 1 6 0 0 0 9 11 1 0 0 0 0 9 30 1 0 0 0 0 10 6 1 6 0 0 0 10 12 1 0 0 0 0 10 31 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 1 0 0 0 12 14 1 0 0 0 0 12 23 1 1 0 0 0 13 15 1 0 0 0 0 13 24 1 6 0 0 0 14 16 1 0 0 0 0 14 25 1 6 0 0 0 15 18 1 0 0 0 0 15 26 1 1 0 0 0 16 19 1 0 0 0 0 16 27 1 1 0 0 0 17 28 2 0 0 0 0 17 32 1 0 0 0 0 18 29 1 6 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 19 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.14
Volume:	415.238
LogP:	-1.396
LogD:	-0.692
LogS:	-1.502
# Rotatable Bonds:	7
TPSA:	215.83
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.189
Synthetic Accessibility Score:	4.172
Fsp3:	0.632
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.381
MDCK Permeability:	0.00011789517157012597
Pgp-inhibitor:	0.003
Pgp-substrate:	0.892
Human Intestinal Absorption (HIA):	0.96
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.208
Plasma Protein Binding (PPB):	28.468603134155273%
Volume Distribution (VD):	0.416
Pgp-substrate:	30.628725051879883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	1.045
Half-life (T1/2):	0.823

ADMET: Toxicity

hERG Blockers:	0.285
Human Hepatotoxicity (H-HT):	0.018
Drug-inuced Liver Injury (DILI):	0.565
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.057
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.089
Respiratory Toxicity:	0.005

Download Data

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

Natural Product: NPC80098

Natural Product ID:	NPC80098
*Common Name:**	Beta-D-Glucopyranosyl 4-O-Beta-D-Glucopyranosylbenzoate
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
Synonyms:
Standard InCHIKey:	MMVLVHFEKMGNDI-XXQLXNJGSA-N
Standard InCHI:	InChI=1S/C19H26O13/c20-5-9-11(22)13(24)15(26)18(30-9)29-8-3-1-7(2-4-8)17(28)32-19-16(27)14(25)12(23)10(6-21)31-19/h1-4,9-16,18-27H,5-6H2/t9-,10-,11-,12-,13+,14+,15-,16-,18-,19+/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480476
PubChem CID:	11259755
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
NPO14305	Moricandia arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844940]
NPO14305	Moricandia arvensis	Species	Brassicaceae	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
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.28	mM	PMID[454966]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	735.4	ug.mL-1	PMID[454966]

☑ 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 NPC80098 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	331
0.1-0.2	1343
0.2-0.3	3253
0.3-0.4	7665
0.4-0.5	10419
0.5-0.6	5343
0.6-0.7	7949
0.7-0.8	5772
0.8-0.85	511
0.85-0.9	94
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9559	High Similarity	NPC79908
0.9493	High Similarity	NPC471028
0.9366	High Similarity	NPC182350
0.9357	High Similarity	NPC291153
0.9333	High Similarity	NPC212729
0.9265	High Similarity	NPC294470
0.9209	High Similarity	NPC245219
0.9209	High Similarity	NPC31081
0.9209	High Similarity	NPC65833
0.9155	High Similarity	NPC473149
0.9103	High Similarity	NPC134905
0.9103	High Similarity	NPC36130
0.9085	High Similarity	NPC474044
0.9044	High Similarity	NPC114116
0.9041	High Similarity	NPC137813
0.9034	High Similarity	NPC213723
0.9028	High Similarity	NPC111785
0.9007	High Similarity	NPC242756
0.8986	High Similarity	NPC471345
0.898	High Similarity	NPC191046
0.898	High Similarity	NPC194095
0.898	High Similarity	NPC327032
0.8978	High Similarity	NPC34456
0.8971	High Similarity	NPC269421
0.8944	High Similarity	NPC77922
0.8944	High Similarity	NPC473281
0.8919	High Similarity	NPC10205
0.8912	High Similarity	NPC157898
0.8889	High Similarity	NPC295970
0.8873	High Similarity	NPC469367
0.8873	High Similarity	NPC478250
0.8859	High Similarity	NPC471405
0.8841	High Similarity	NPC471029
0.8836	High Similarity	NPC104172
0.8836	High Similarity	NPC88886
0.8828	High Similarity	NPC218685
0.8828	High Similarity	NPC140722
0.8828	High Similarity	NPC4958
0.8828	High Similarity	NPC92054
0.88	High Similarity	NPC43638
0.88	High Similarity	NPC133984
0.8784	High Similarity	NPC259767
0.8784	High Similarity	NPC88484
0.8767	High Similarity	NPC22137
0.8742	High Similarity	NPC160780
0.8742	High Similarity	NPC74319
0.8742	High Similarity	NPC289811
0.8742	High Similarity	NPC43761
0.8742	High Similarity	NPC287872
0.8733	High Similarity	NPC127406
0.8733	High Similarity	NPC170475
0.8725	High Similarity	NPC478232
0.8716	High Similarity	NPC23253
0.8714	High Similarity	NPC166180
0.8707	High Similarity	NPC227980
0.8707	High Similarity	NPC205054
0.8699	High Similarity	NPC302989
0.8693	High Similarity	NPC472876
0.8684	High Similarity	NPC239966
0.8684	High Similarity	NPC328093
0.8684	High Similarity	NPC203020
0.8684	High Similarity	NPC289346
0.8676	High Similarity	NPC146540
0.8675	High Similarity	NPC1913
0.8671	High Similarity	NPC184053
0.8667	High Similarity	NPC97052
0.8667	High Similarity	NPC99233
0.8667	High Similarity	NPC26195
0.8667	High Similarity	NPC39351
0.8667	High Similarity	NPC169248
0.8667	High Similarity	NPC72649
0.8658	High Similarity	NPC105827
0.8658	High Similarity	NPC259182
0.8658	High Similarity	NPC310661
0.8658	High Similarity	NPC121001
0.8649	High Similarity	NPC93619
0.8649	High Similarity	NPC131874
0.8649	High Similarity	NPC191154
0.8639	High Similarity	NPC478234
0.8639	High Similarity	NPC478236
0.8639	High Similarity	NPC199335
0.8627	High Similarity	NPC195685
0.8627	High Similarity	NPC25389
0.8627	High Similarity	NPC477628
0.8627	High Similarity	NPC472859
0.8627	High Similarity	NPC311803
0.8627	High Similarity	NPC472994
0.8627	High Similarity	NPC477629
0.8627	High Similarity	NPC101636
0.8627	High Similarity	NPC210961
0.8627	High Similarity	NPC270675
0.8623	High Similarity	NPC104854
0.8611	High Similarity	NPC475213
0.8611	High Similarity	NPC152796
0.8609	High Similarity	NPC295613
0.8609	High Similarity	NPC473657
0.8609	High Similarity	NPC265480
0.8609	High Similarity	NPC45165
0.8609	High Similarity	NPC149368
0.8609	High Similarity	NPC206378
0.86	High Similarity	NPC185103
0.86	High Similarity	NPC143851
0.86	High Similarity	NPC210003
0.86	High Similarity	NPC29763
0.86	High Similarity	NPC83283
0.86	High Similarity	NPC106625
0.86	High Similarity	NPC39360
0.8591	High Similarity	NPC289438
0.8591	High Similarity	NPC134819
0.8582	High Similarity	NPC103409
0.8581	High Similarity	NPC100818
0.8581	High Similarity	NPC107197
0.8571	High Similarity	NPC83975
0.8571	High Similarity	NPC23084
0.8571	High Similarity	NPC472339
0.8571	High Similarity	NPC90905
0.8571	High Similarity	NPC285108
0.8571	High Similarity	NPC298171
0.8571	High Similarity	NPC33298
0.8571	High Similarity	NPC4013
0.8562	High Similarity	NPC472320
0.8562	High Similarity	NPC166277
0.8562	High Similarity	NPC119125
0.8562	High Similarity	NPC271479
0.8562	High Similarity	NPC473867
0.8562	High Similarity	NPC200708
0.8553	High Similarity	NPC65003
0.8553	High Similarity	NPC473512
0.8553	High Similarity	NPC23817
0.8553	High Similarity	NPC44931
0.8553	High Similarity	NPC313163
0.8553	High Similarity	NPC161749
0.8553	High Similarity	NPC129827
0.8553	High Similarity	NPC197896
0.8553	High Similarity	NPC472860
0.8553	High Similarity	NPC226759
0.8553	High Similarity	NPC258035
0.8553	High Similarity	NPC156457
0.8543	High Similarity	NPC27408
0.8543	High Similarity	NPC95090
0.8542	High Similarity	NPC164599
0.8533	High Similarity	NPC215811
0.8531	High Similarity	NPC202700
0.8529	High Similarity	NPC114096
0.8526	High Similarity	NPC282551
0.8523	High Similarity	NPC158546
0.8523	High Similarity	NPC475379
0.8523	High Similarity	NPC106025
0.8523	High Similarity	NPC477240
0.8523	High Similarity	NPC214454
0.8523	High Similarity	NPC289021
0.8519	High Similarity	NPC221798
0.8516	High Similarity	NPC80068
0.8514	High Similarity	NPC98809
0.8514	High Similarity	NPC476394
0.8506	High Similarity	NPC303913
0.8506	High Similarity	NPC224530
0.8506	High Similarity	NPC216496
0.8506	High Similarity	NPC85707
0.8506	High Similarity	NPC282169
0.8506	High Similarity	NPC259957
0.8506	High Similarity	NPC129217
0.8506	High Similarity	NPC159579
0.8506	High Similarity	NPC48093
0.8497	Intermediate Similarity	NPC73511
0.8497	Intermediate Similarity	NPC138811
0.8497	Intermediate Similarity	NPC473634
0.8497	Intermediate Similarity	NPC308265
0.8497	Intermediate Similarity	NPC22062
0.8496	Intermediate Similarity	NPC469412
0.8496	Intermediate Similarity	NPC198734
0.8487	Intermediate Similarity	NPC307938
0.8487	Intermediate Similarity	NPC323593
0.8487	Intermediate Similarity	NPC203500
0.8477	Intermediate Similarity	NPC230439
0.8477	Intermediate Similarity	NPC92153
0.8477	Intermediate Similarity	NPC268950
0.8477	Intermediate Similarity	NPC279281
0.8477	Intermediate Similarity	NPC108706
0.8477	Intermediate Similarity	NPC78021
0.8477	Intermediate Similarity	NPC299761
0.8477	Intermediate Similarity	NPC87304
0.8477	Intermediate Similarity	NPC211158
0.8472	Intermediate Similarity	NPC186406
0.8472	Intermediate Similarity	NPC215512
0.8472	Intermediate Similarity	NPC476442
0.8467	Intermediate Similarity	NPC190217
0.8467	Intermediate Similarity	NPC478235
0.8467	Intermediate Similarity	NPC194705
0.8467	Intermediate Similarity	NPC148026
0.8462	Intermediate Similarity	NPC99216
0.8462	Intermediate Similarity	NPC129264
0.8462	Intermediate Similarity	NPC205824
0.8462	Intermediate Similarity	NPC85751
0.8462	Intermediate Similarity	NPC19240
0.8462	Intermediate Similarity	NPC139060
0.8462	Intermediate Similarity	NPC475979
0.8452	Intermediate Similarity	NPC27942
0.8452	Intermediate Similarity	NPC148273
0.8452	Intermediate Similarity	NPC41009

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 NPC80098 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	794
0.2-0.3	1639
0.3-0.4	2597
0.4-0.5	2110
0.5-0.6	1136
0.6-0.7	466
0.7-0.8	123
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
0.8553	High Similarity	NPD4381	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD4628	Phase 3
0.8235	Intermediate Similarity	NPD8455	Phase 2
0.8075	Intermediate Similarity	NPD7054	Approved
0.8075	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD1091	Approved
0.8025	Intermediate Similarity	NPD7074	Phase 3
0.8025	Intermediate Similarity	NPD7472	Approved
0.8013	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6799	Approved
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6797	Phase 2
0.7973	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7075	Discontinued
0.7935	Intermediate Similarity	NPD6801	Discontinued
0.7927	Intermediate Similarity	NPD7251	Discontinued
0.7927	Intermediate Similarity	NPD7685	Pre-registration
0.7922	Intermediate Similarity	NPD4380	Phase 2
0.7908	Intermediate Similarity	NPD1653	Approved
0.7879	Intermediate Similarity	NPD7808	Phase 3
0.7868	Intermediate Similarity	NPD9545	Approved
0.7847	Intermediate Similarity	NPD6233	Phase 2
0.7843	Intermediate Similarity	NPD5403	Approved
0.7838	Intermediate Similarity	NPD7266	Discontinued
0.7829	Intermediate Similarity	NPD5401	Approved
0.7818	Intermediate Similarity	NPD6559	Discontinued
0.7785	Intermediate Similarity	NPD1549	Phase 2
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7411	Suspended
0.774	Intermediate Similarity	NPD1933	Approved
0.7727	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8313	Approved
0.7725	Intermediate Similarity	NPD8312	Approved
0.7722	Intermediate Similarity	NPD3817	Phase 2
0.7718	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6599	Discontinued
0.7658	Intermediate Similarity	NPD7819	Suspended
0.7655	Intermediate Similarity	NPD6798	Discontinued
0.7651	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6190	Approved
0.761	Intermediate Similarity	NPD5402	Approved
0.7595	Intermediate Similarity	NPD1934	Approved
0.7561	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6166	Phase 2
0.7547	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2796	Approved
0.753	Intermediate Similarity	NPD5844	Phase 1
0.7517	Intermediate Similarity	NPD7097	Phase 1
0.7517	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7483	Intermediate Similarity	NPD4062	Phase 3
0.7467	Intermediate Similarity	NPD7033	Discontinued
0.7465	Intermediate Similarity	NPD9717	Approved
0.7451	Intermediate Similarity	NPD3750	Approved
0.7451	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7431	Intermediate Similarity	NPD1203	Approved
0.7417	Intermediate Similarity	NPD1551	Phase 2
0.7414	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2354	Approved
0.7403	Intermediate Similarity	NPD3887	Approved
0.7383	Intermediate Similarity	NPD6355	Discontinued
0.7372	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1241	Discontinued
0.7361	Intermediate Similarity	NPD3225	Approved
0.7357	Intermediate Similarity	NPD1894	Discontinued
0.7355	Intermediate Similarity	NPD7440	Discontinued
0.7351	Intermediate Similarity	NPD3748	Approved
0.7351	Intermediate Similarity	NPD1510	Phase 2
0.7343	Intermediate Similarity	NPD1608	Approved
0.7329	Intermediate Similarity	NPD2801	Approved
0.7313	Intermediate Similarity	NPD1358	Approved
0.7308	Intermediate Similarity	NPD1511	Approved
0.7297	Intermediate Similarity	NPD2313	Discontinued
0.7289	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD37	Approved
0.7267	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD4340	Discontinued
0.7262	Intermediate Similarity	NPD3751	Discontinued
0.7262	Intermediate Similarity	NPD7228	Approved
0.7261	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1019	Discontinued
0.7246	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4967	Phase 2
0.7239	Intermediate Similarity	NPD4965	Approved
0.7239	Intermediate Similarity	NPD3882	Suspended
0.7239	Intermediate Similarity	NPD4966	Approved
0.7237	Intermediate Similarity	NPD2799	Discontinued
0.7229	Intermediate Similarity	NPD3787	Discontinued
0.7225	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1481	Phase 2
0.7215	Intermediate Similarity	NPD1512	Approved
0.7215	Intermediate Similarity	NPD6273	Approved
0.7212	Intermediate Similarity	NPD5494	Approved
0.7211	Intermediate Similarity	NPD9494	Approved
0.7208	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1240	Approved
0.72	Intermediate Similarity	NPD3142	Approved
0.72	Intermediate Similarity	NPD3140	Approved
0.7192	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2797	Approved
0.719	Intermediate Similarity	NPD2935	Discontinued
0.7188	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3764	Approved
0.7181	Intermediate Similarity	NPD3268	Approved
0.7178	Intermediate Similarity	NPD5353	Approved
0.7174	Intermediate Similarity	NPD7843	Approved
0.7174	Intermediate Similarity	NPD7583	Approved
0.7153	Intermediate Similarity	NPD1535	Discovery
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5647	Approved
0.7135	Intermediate Similarity	NPD7585	Approved
0.7134	Intermediate Similarity	NPD5058	Phase 3
0.7134	Intermediate Similarity	NPD7768	Phase 2
0.7133	Intermediate Similarity	NPD17	Approved
0.7133	Intermediate Similarity	NPD1778	Approved
0.7132	Intermediate Similarity	NPD2684	Approved
0.7124	Intermediate Similarity	NPD4308	Phase 3
0.7111	Intermediate Similarity	NPD3134	Approved
0.7107	Intermediate Similarity	NPD2186	Approved
0.7105	Intermediate Similarity	NPD1607	Approved
0.7105	Intermediate Similarity	NPD6653	Approved
0.7103	Intermediate Similarity	NPD3972	Approved
0.7099	Intermediate Similarity	NPD6385	Approved
0.7099	Intermediate Similarity	NPD6386	Approved
0.7097	Intermediate Similarity	NPD2424	Discontinued
0.7093	Intermediate Similarity	NPD7240	Approved
0.7091	Intermediate Similarity	NPD3749	Approved
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7081	Intermediate Similarity	NPD3226	Approved
0.7078	Intermediate Similarity	NPD2240	Approved
0.7078	Intermediate Similarity	NPD2239	Approved
0.7066	Intermediate Similarity	NPD8127	Discontinued
0.7066	Intermediate Similarity	NPD6959	Discontinued
0.7063	Intermediate Similarity	NPD920	Approved
0.7059	Intermediate Similarity	NPD290	Approved
0.7044	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD422	Phase 1
0.7032	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2346	Discontinued
0.7032	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6004	Phase 3
0.7032	Intermediate Similarity	NPD6005	Phase 3
0.7032	Intermediate Similarity	NPD6002	Phase 3
0.7027	Intermediate Similarity	NPD2798	Approved
0.7025	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6232	Discontinued
0.7021	Intermediate Similarity	NPD7157	Approved
0.7021	Intermediate Similarity	NPD7783	Phase 2
0.7021	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7435	Discontinued
0.7006	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7095	Approved
0.7	Intermediate Similarity	NPD5049	Phase 3
0.6994	Remote Similarity	NPD7039	Approved
0.6994	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7038	Approved
0.6989	Remote Similarity	NPD7584	Approved
0.6987	Remote Similarity	NPD5958	Discontinued
0.6987	Remote Similarity	NPD4534	Discontinued
0.6978	Remote Similarity	NPD969	Suspended
0.6974	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1613	Approved
0.6974	Remote Similarity	NPD4307	Phase 2
0.6972	Remote Similarity	NPD9493	Approved
0.6959	Remote Similarity	NPD3267	Approved
0.6959	Remote Similarity	NPD6362	Approved
0.6959	Remote Similarity	NPD3266	Approved
0.6954	Remote Similarity	NPD411	Approved
0.6954	Remote Similarity	NPD1296	Phase 2
0.6948	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4538	Approved
0.6948	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4536	Approved
0.6943	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1243	Approved
0.6943	Remote Similarity	NPD6674	Discontinued
0.694	Remote Similarity	NPD6780	Approved
0.694	Remote Similarity	NPD6776	Approved
0.694	Remote Similarity	NPD6778	Approved

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