NPASS Compound

Structure

NPC215811 OpenBabel07101718202D 29 31 0 0 1 0 0 0 0 0999 V2000 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 21 2 0 0 0 0 10 27 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 13 22 1 0 0 0 0 14 28 1 0 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 20 1 0 0 0 0 18 25 1 6 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 20 28 1 1 0 0 0 20 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.11
Volume:	386.827
LogP:	1.622
LogD:	1.2
LogS:	-3.52
# Rotatable Bonds:	7
TPSA:	142.75
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.393
Synthetic Accessibility Score:	3.572
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
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:	-6.096
MDCK Permeability:	2.649112866492942e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.621
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.524
Plasma Protein Binding (PPB):	94.33220672607422%
Volume Distribution (VD):	0.818
Pgp-substrate:	4.134923458099365%

ADMET: Metabolism

CYP1A2-inhibitor:	0.182
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.715
CYP2D6-inhibitor:	0.192
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	6.974
Half-life (T1/2):	0.88

ADMET: Toxicity

hERG Blockers:	0.201
Human Hepatotoxicity (H-HT):	0.021
Drug-inuced Liver Injury (DILI):	0.168
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.447
Carcinogencity:	0.219
Eye Corrosion:	0.005
Eye Irritation:	0.918
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC215811

Natural Product ID:	NPC215811
*Common Name:**	Flacourtoside B
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-(2-formyl-4-hydroxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl benzoate
Synonyms:	Flacourtoside B
Standard InCHIKey:	SSJSZNSQHPLDCR-BFMVXSJESA-N
Standard InCHI:	InChI=1S/C20H20O9/c21-9-12-8-13(22)6-7-14(12)28-20-18(25)17(24)16(23)15(29-20)10-27-19(26)11-4-2-1-3-5-11/h1-9,15-18,20,22-25H,10H2/t15-,16-,17+,18-,20-/m1/s1
SMILES:	c1ccc(cc1)C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2ccc(cc2C=O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036484
PubChem CID:	57409244
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
NPO33462	flacourtia ramontchi	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22439591]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	71100.0	nM	PMID[495409]

☑ 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 NPC215811 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	352
0.1-0.2	1507
0.2-0.3	3760
0.3-0.4	8458
0.4-0.5	9870
0.5-0.6	4391
0.6-0.7	6655
0.7-0.8	6844
0.8-0.85	728
0.85-0.9	100
0.9-0.95	23
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9539	High Similarity	NPC132737
0.953	High Similarity	NPC230439
0.953	High Similarity	NPC279281
0.953	High Similarity	NPC92153
0.953	High Similarity	NPC299761
0.9521	High Similarity	NPC83975
0.9521	High Similarity	NPC140722
0.9521	High Similarity	NPC4958
0.9521	High Similarity	NPC92054
0.94	High Similarity	NPC260604
0.94	High Similarity	NPC299435
0.9333	High Similarity	NPC34965
0.9333	High Similarity	NPC183536
0.9329	High Similarity	NPC93619
0.9281	High Similarity	NPC57072
0.9281	High Similarity	NPC231475
0.9241	High Similarity	NPC65833
0.9216	High Similarity	NPC476026
0.9216	High Similarity	NPC474401
0.9216	High Similarity	NPC474398
0.9216	High Similarity	NPC474441
0.9161	High Similarity	NPC217950
0.9145	High Similarity	NPC185103
0.9128	High Similarity	NPC302989
0.911	High Similarity	NPC245219
0.911	High Similarity	NPC31081
0.9091	High Similarity	NPC177742
0.8987	High Similarity	NPC280923
0.894	High Similarity	NPC22137
0.8924	High Similarity	NPC127415
0.8924	High Similarity	NPC475183
0.8896	High Similarity	NPC470331
0.8868	High Similarity	NPC178281
0.8861	High Similarity	NPC22324
0.8861	High Similarity	NPC56735
0.8861	High Similarity	NPC61594
0.8854	High Similarity	NPC328093
0.8851	High Similarity	NPC145319
0.8851	High Similarity	NPC164599
0.8824	High Similarity	NPC131874
0.8816	High Similarity	NPC111785
0.8812	High Similarity	NPC475174
0.8805	High Similarity	NPC147596
0.8797	High Similarity	NPC71780
0.8792	High Similarity	NPC242756
0.879	High Similarity	NPC287872
0.879	High Similarity	NPC74319
0.8774	High Similarity	NPC327032
0.8774	High Similarity	NPC191046
0.8774	High Similarity	NPC194095
0.8766	High Similarity	NPC36130
0.8766	High Similarity	NPC134905
0.8765	High Similarity	NPC280385
0.8758	High Similarity	NPC116745
0.8758	High Similarity	NPC182350
0.8742	High Similarity	NPC212099
0.8742	High Similarity	NPC101116
0.8742	High Similarity	NPC278329
0.8742	High Similarity	NPC146837
0.8726	High Similarity	NPC43638
0.8718	High Similarity	NPC10205
0.8712	High Similarity	NPC254540
0.8712	High Similarity	NPC172807
0.8712	High Similarity	NPC211594
0.8712	High Similarity	NPC472386
0.871	High Similarity	NPC259767
0.871	High Similarity	NPC88484
0.8704	High Similarity	NPC472133
0.8688	High Similarity	NPC17432
0.8688	High Similarity	NPC88043
0.8684	High Similarity	NPC474422
0.8679	High Similarity	NPC311803
0.8679	High Similarity	NPC472859
0.8679	High Similarity	NPC25389
0.8675	High Similarity	NPC138915
0.8667	High Similarity	NPC472991
0.8667	High Similarity	NPC472992
0.8662	High Similarity	NPC471405
0.8662	High Similarity	NPC261866
0.8662	High Similarity	NPC127406
0.8659	High Similarity	NPC470438
0.865	High Similarity	NPC34287
0.865	High Similarity	NPC472129
0.865	High Similarity	NPC204937
0.865	High Similarity	NPC210808
0.865	High Similarity	NPC44558
0.865	High Similarity	NPC149011
0.865	High Similarity	NPC105511
0.865	High Similarity	NPC471416
0.865	High Similarity	NPC199079
0.865	High Similarity	NPC43434
0.8642	High Similarity	NPC58716
0.8642	High Similarity	NPC45618
0.8642	High Similarity	NPC146792
0.8634	High Similarity	NPC165720
0.8634	High Similarity	NPC99216
0.8634	High Similarity	NPC472130
0.8634	High Similarity	NPC472131
0.8625	High Similarity	NPC90905
0.8625	High Similarity	NPC4013
0.8618	High Similarity	NPC291153
0.8616	High Similarity	NPC166277
0.8616	High Similarity	NPC119125
0.8614	High Similarity	NPC476620
0.8614	High Similarity	NPC476622
0.8614	High Similarity	NPC472387
0.8614	High Similarity	NPC476621
0.8614	High Similarity	NPC476623
0.8614	High Similarity	NPC476619
0.8614	High Similarity	NPC476618
0.8609	High Similarity	NPC471028
0.8608	High Similarity	NPC156457
0.8608	High Similarity	NPC313163
0.8608	High Similarity	NPC60966
0.8608	High Similarity	NPC258035
0.8608	High Similarity	NPC161749
0.8608	High Similarity	NPC133984
0.8608	High Similarity	NPC197896
0.8606	High Similarity	NPC49344
0.8606	High Similarity	NPC264735
0.8606	High Similarity	NPC43211
0.8606	High Similarity	NPC135277
0.8606	High Similarity	NPC210094
0.8606	High Similarity	NPC101191
0.8606	High Similarity	NPC237435
0.8606	High Similarity	NPC115760
0.8606	High Similarity	NPC477848
0.8599	High Similarity	NPC99233
0.8598	High Similarity	NPC307518
0.8598	High Similarity	NPC9002
0.8598	High Similarity	NPC288152
0.8598	High Similarity	NPC257011
0.8598	High Similarity	NPC137871
0.8598	High Similarity	NPC205076
0.8598	High Similarity	NPC48773
0.859	High Similarity	NPC121001
0.859	High Similarity	NPC259182
0.859	High Similarity	NPC137813
0.859	High Similarity	NPC157898
0.8589	High Similarity	NPC186807
0.8589	High Similarity	NPC93337
0.8589	High Similarity	NPC45638
0.8589	High Similarity	NPC58053
0.8589	High Similarity	NPC472383
0.8589	High Similarity	NPC472381
0.8589	High Similarity	NPC469931
0.8589	High Similarity	NPC246274
0.8589	High Similarity	NPC226294
0.8589	High Similarity	NPC170675
0.8589	High Similarity	NPC475942
0.8589	High Similarity	NPC105025
0.8589	High Similarity	NPC112755
0.8589	High Similarity	NPC201292
0.8589	High Similarity	NPC471457
0.8581	High Similarity	NPC475890
0.858	High Similarity	NPC70441
0.8571	High Similarity	NPC168822
0.8562	High Similarity	NPC195685
0.8562	High Similarity	NPC472994
0.8562	High Similarity	NPC210961
0.8562	High Similarity	NPC477628
0.8562	High Similarity	NPC282169
0.8562	High Similarity	NPC270675
0.8562	High Similarity	NPC477629
0.8554	High Similarity	NPC211532
0.8554	High Similarity	NPC472380
0.8554	High Similarity	NPC472385
0.8554	High Similarity	NPC233994
0.8554	High Similarity	NPC198324
0.8554	High Similarity	NPC472384
0.8554	High Similarity	NPC472382
0.8554	High Similarity	NPC268533
0.8553	High Similarity	NPC289811
0.8553	High Similarity	NPC73511
0.8553	High Similarity	NPC43761
0.8553	High Similarity	NPC160780
0.8545	High Similarity	NPC172033
0.8545	High Similarity	NPC88560
0.8545	High Similarity	NPC175230
0.8544	High Similarity	NPC170475
0.8544	High Similarity	NPC149368
0.8544	High Similarity	NPC265480
0.8537	High Similarity	NPC235260
0.8537	High Similarity	NPC474434
0.8537	High Similarity	NPC224462
0.8537	High Similarity	NPC84265
0.8537	High Similarity	NPC155763
0.8537	High Similarity	NPC245014
0.8537	High Similarity	NPC183357
0.8537	High Similarity	NPC22195
0.8537	High Similarity	NPC20505
0.8537	High Similarity	NPC21190
0.8537	High Similarity	NPC282987
0.8535	High Similarity	NPC29763
0.8535	High Similarity	NPC83283
0.8535	High Similarity	NPC472128
0.8535	High Similarity	NPC210003
0.8535	High Similarity	NPC143851
0.8535	High Similarity	NPC39360
0.8535	High Similarity	NPC106625

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 NPC215811 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	851
0.2-0.3	1836
0.3-0.4	2633
0.4-0.5	1901
0.5-0.6	1094
0.6-0.7	377
0.7-0.8	144
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8608	High Similarity	NPD4381	Clinical (unspecified phase)
0.8606	High Similarity	NPD4338	Clinical (unspecified phase)
0.8599	High Similarity	NPD5402	Approved
0.8545	High Similarity	NPD6559	Discontinued
0.8443	Intermediate Similarity	NPD8313	Approved
0.8443	Intermediate Similarity	NPD8312	Approved
0.8415	Intermediate Similarity	NPD3818	Discontinued
0.8253	Intermediate Similarity	NPD7054	Approved
0.8212	Intermediate Similarity	NPD1551	Phase 2
0.8204	Intermediate Similarity	NPD7472	Approved
0.8204	Intermediate Similarity	NPD7074	Phase 3
0.8155	Intermediate Similarity	NPD6797	Phase 2
0.8153	Intermediate Similarity	NPD5403	Approved
0.8107	Intermediate Similarity	NPD7251	Discontinued
0.8103	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD1653	Approved
0.8086	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7808	Phase 3
0.8037	Intermediate Similarity	NPD7075	Discontinued
0.8036	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD4380	Phase 2
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.7963	Intermediate Similarity	NPD2801	Approved
0.7947	Intermediate Similarity	NPD1933	Approved
0.7901	Intermediate Similarity	NPD1934	Approved
0.7891	Intermediate Similarity	NPD1203	Approved
0.7885	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8455	Phase 2
0.7853	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD447	Suspended
0.7805	Intermediate Similarity	NPD3817	Phase 2
0.7791	Intermediate Similarity	NPD7685	Pre-registration
0.7791	Intermediate Similarity	NPD6801	Discontinued
0.7771	Intermediate Similarity	NPD4628	Phase 3
0.7756	Intermediate Similarity	NPD1549	Phase 2
0.7751	Intermediate Similarity	NPD6166	Phase 2
0.7751	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2313	Discontinued
0.7744	Intermediate Similarity	NPD7819	Suspended
0.774	Intermediate Similarity	NPD1091	Approved
0.7736	Intermediate Similarity	NPD6799	Approved
0.7733	Intermediate Similarity	NPD6832	Phase 2
0.7716	Intermediate Similarity	NPD3226	Approved
0.7712	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2346	Discontinued
0.7692	Intermediate Similarity	NPD7266	Discontinued
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD7435	Discontinued
0.7661	Intermediate Similarity	NPD3751	Discontinued
0.7651	Intermediate Similarity	NPD3882	Suspended
0.763	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1511	Approved
0.7622	Intermediate Similarity	NPD7411	Suspended
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.761	Intermediate Similarity	NPD6190	Approved
0.7596	Intermediate Similarity	NPD6779	Approved
0.7596	Intermediate Similarity	NPD6781	Approved
0.7596	Intermediate Similarity	NPD6776	Approved
0.7596	Intermediate Similarity	NPD6777	Approved
0.7596	Intermediate Similarity	NPD6778	Approved
0.7596	Intermediate Similarity	NPD6780	Approved
0.7596	Intermediate Similarity	NPD6782	Approved
0.7576	Intermediate Similarity	NPD6844	Discontinued
0.7568	Intermediate Similarity	NPD9717	Approved
0.7531	Intermediate Similarity	NPD1512	Approved
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7515	Intermediate Similarity	NPD5494	Approved
0.7514	Intermediate Similarity	NPD6823	Phase 2
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7783	Phase 2
0.7472	Intermediate Similarity	NPD8434	Phase 2
0.7469	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6233	Phase 2
0.7455	Intermediate Similarity	NPD6599	Discontinued
0.7452	Intermediate Similarity	NPD7033	Discontinued
0.7452	Intermediate Similarity	NPD2799	Discontinued
0.7452	Intermediate Similarity	NPD1510	Phase 2
0.744	Intermediate Similarity	NPD7768	Phase 2
0.7438	Intermediate Similarity	NPD3750	Approved
0.7427	Intermediate Similarity	NPD6232	Discontinued
0.7425	Intermediate Similarity	NPD1465	Phase 2
0.7421	Intermediate Similarity	NPD7874	Approved
0.7421	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2796	Approved
0.7403	Intermediate Similarity	NPD411	Approved
0.7381	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7697	Approved
0.738	Intermediate Similarity	NPD7696	Phase 3
0.738	Intermediate Similarity	NPD7698	Approved
0.7368	Intermediate Similarity	NPD2798	Approved
0.7365	Intermediate Similarity	NPD37	Approved
0.7356	Intermediate Similarity	NPD7228	Approved
0.7353	Intermediate Similarity	NPD6234	Discontinued
0.7341	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7871	Phase 2
0.734	Intermediate Similarity	NPD7870	Phase 2
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7337	Intermediate Similarity	NPD4966	Approved
0.7322	Intermediate Similarity	NPD6534	Approved
0.7322	Intermediate Similarity	NPD6535	Approved
0.7318	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7701	Phase 2
0.7312	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7473	Discontinued
0.7294	Intermediate Similarity	NPD3749	Approved
0.729	Intermediate Similarity	NPD6798	Discontinued
0.7278	Intermediate Similarity	NPD8150	Discontinued
0.7273	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6213	Phase 3
0.7268	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6212	Phase 3
0.7267	Intermediate Similarity	NPD6959	Discontinued
0.7267	Intermediate Similarity	NPD7199	Phase 2
0.7256	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1019	Discontinued
0.725	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3225	Approved
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD9493	Approved
0.7208	Intermediate Similarity	NPD2861	Phase 2
0.7204	Intermediate Similarity	NPD7699	Phase 2
0.7204	Intermediate Similarity	NPD7700	Phase 2
0.7202	Intermediate Similarity	NPD7801	Approved
0.72	Intermediate Similarity	NPD3496	Discontinued
0.7197	Intermediate Similarity	NPD1240	Approved
0.7197	Intermediate Similarity	NPD1613	Approved
0.7197	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2797	Approved
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7179	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD920	Approved
0.7152	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD230	Phase 1
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD2533	Approved
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7125	Intermediate Similarity	NPD3748	Approved
0.7107	Intermediate Similarity	NPD1607	Approved
0.7105	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD1481	Phase 2
0.7097	Intermediate Similarity	NPD9494	Approved
0.7086	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7584	Approved
0.707	Intermediate Similarity	NPD3268	Approved
0.707	Intermediate Similarity	NPD3764	Approved
0.7069	Intermediate Similarity	NPD1247	Approved
0.7068	Intermediate Similarity	NPD8320	Phase 1
0.7068	Intermediate Similarity	NPD8319	Approved
0.7063	Intermediate Similarity	NPD7097	Phase 1
0.7063	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD919	Approved
0.705	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4661	Approved
0.7048	Intermediate Similarity	NPD4662	Approved
0.7039	Intermediate Similarity	NPD5953	Discontinued
0.7039	Intermediate Similarity	NPD1535	Discovery
0.7037	Intermediate Similarity	NPD2344	Approved
0.7032	Intermediate Similarity	NPD5647	Approved
0.703	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1778	Approved
0.7006	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD6653	Approved
0.7	Intermediate Similarity	NPD9545	Approved
0.7	Intermediate Similarity	NPD7240	Approved
0.6981	Remote Similarity	NPD4060	Phase 1
0.6981	Remote Similarity	NPD4307	Phase 2
0.6975	Remote Similarity	NPD6032	Approved
0.6968	Remote Similarity	NPD1470	Approved
0.6962	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7585	Approved
0.6951	Remote Similarity	NPD1652	Phase 2
0.6949	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6004	Phase 3
0.6933	Remote Similarity	NPD6005	Phase 3
0.6933	Remote Similarity	NPD6002	Phase 3
0.6933	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7440	Discontinued
0.6927	Remote Similarity	NPD7286	Phase 2
0.6919	Remote Similarity	NPD7930	Approved
0.6918	Remote Similarity	NPD4062	Phase 3
0.6908	Remote Similarity	NPD17	Approved
0.6907	Remote Similarity	NPD7583	Approved
0.6906	Remote Similarity	NPD7039	Approved
0.6906	Remote Similarity	NPD7038	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