NPASS Compound

Structure

NPC279732 OpenBabel07101718302D 30 32 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 3.4641 -0.0000 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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 1.6691 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 3.4641 1.0000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -1.7321 0.0000 0.0000 C 0 0 2 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8060 2.4781 0.0000 C 0 0 0 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 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -2.5981 1.5000 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 2.1369 3.2213 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 2.5827 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 7 2 0 0 0 0 2 8 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 4 12 1 0 0 0 0 5 7 1 0 0 0 0 5 28 1 0 0 0 0 6 27 1 0 0 0 0 7 13 1 0 0 0 0 8 26 1 0 0 0 0 9 13 2 0 0 0 0 9 29 1 0 0 0 0 10 6 1 6 0 0 0 10 14 1 0 0 0 0 10 30 1 0 0 0 0 11 19 2 0 0 0 0 11 20 1 0 0 0 0 12 21 2 0 0 0 0 12 27 1 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 1 0 0 0 15 16 1 0 0 0 0 15 23 1 6 0 0 0 16 18 1 0 0 0 0 16 24 1 1 0 0 0 17 25 2 0 0 0 0 17 28 1 0 0 0 0 18 29 1 6 0 0 0 18 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.1
Volume:	383.879
LogP:	-0.211
LogD:	-0.315
LogS:	-1.827
# Rotatable Bonds:	8
TPSA:	178.28
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.294
Synthetic Accessibility Score:	3.976
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
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:	-6.297
MDCK Permeability:	6.612684956053272e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.43
Human Intestinal Absorption (HIA):	0.928
20% Bioavailability (F20%):	0.142
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	32.2183952331543%
Volume Distribution (VD):	0.244
Pgp-substrate:	34.203269958496094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.393
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	3.007
Half-life (T1/2):	0.951

ADMET: Toxicity

hERG Blockers:	0.253
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.306
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.135
Carcinogencity:	0.129
Eye Corrosion:	0.004
Eye Irritation:	0.298
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC279732

Natural Product ID:	NPC279732
*Common Name:**	7-O-Beta-D-(6'-O-Malonyl)-Glucopyranosyl-5-Methoxy-1(3H)-Isobenzofuranone
IUPAC Name:	3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(6-methoxy-3-oxo-1H-2-benzofuran-4-yl)oxy]oxan-2-yl]methoxy]propanoic acid
Synonyms:
Standard InCHIKey:	ITXSQBBBWUMWDG-PFNPHEKDSA-N
Standard InCHI:	InChI=1S/C18H20O12/c1-26-8-2-7-5-28-17(25)13(7)9(3-8)29-18-16(24)15(23)14(22)10(30-18)6-27-12(21)4-11(19)20/h2-3,10,14-16,18,22-24H,4-6H2,1H3,(H,19,20)/t10-,14-,15+,16-,18-/m1/s1
SMILES:	COc1cc2COC(=O)c2c(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)CC(=O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2442456
PubChem CID:	72697730
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
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678669]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24094434]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25148	Helichrysum italicum	Species	Asteraceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	27.0	%	PMID[508804]

☑ 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 NPC279732 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	347
0.1-0.2	1455
0.2-0.3	3448
0.3-0.4	7399
0.4-0.5	10289
0.5-0.6	5030
0.6-0.7	5565
0.7-0.8	7003
0.8-0.85	1849
0.85-0.9	299
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9182	High Similarity	NPC7752
0.9172	High Similarity	NPC470358
0.9091	High Similarity	NPC215921
0.9091	High Similarity	NPC200773
0.9091	High Similarity	NPC23253
0.9091	High Similarity	NPC240768
0.9091	High Similarity	NPC70016
0.9068	High Similarity	NPC249977
0.902	High Similarity	NPC199335
0.9012	High Similarity	NPC473202
0.8981	High Similarity	NPC17521
0.8974	High Similarity	NPC185103
0.8968	High Similarity	NPC190217
0.8957	High Similarity	NPC298778
0.8954	High Similarity	NPC218685
0.8954	High Similarity	NPC23084
0.8938	High Similarity	NPC22324
0.8931	High Similarity	NPC328093
0.8924	High Similarity	NPC470606
0.8924	High Similarity	NPC190020
0.8924	High Similarity	NPC77679
0.8924	High Similarity	NPC84935
0.891	High Similarity	NPC475116
0.8909	High Similarity	NPC470454
0.8909	High Similarity	NPC68381
0.8909	High Similarity	NPC199533
0.8903	High Similarity	NPC106025
0.8903	High Similarity	NPC477240
0.8903	High Similarity	NPC191154
0.8903	High Similarity	NPC214454
0.8903	High Similarity	NPC213723
0.8896	High Similarity	NPC191653
0.8889	High Similarity	NPC178851
0.8875	High Similarity	NPC69868
0.8874	High Similarity	NPC469579
0.8868	High Similarity	NPC43761
0.8868	High Similarity	NPC470607
0.8861	High Similarity	NPC127406
0.8861	High Similarity	NPC150227
0.8861	High Similarity	NPC261866
0.8855	High Similarity	NPC475233
0.8848	High Similarity	NPC98776
0.8846	High Similarity	NPC473732
0.8846	High Similarity	NPC134819
0.8834	High Similarity	NPC116745
0.8827	High Similarity	NPC99216
0.8812	High Similarity	NPC110349
0.8805	High Similarity	NPC43638
0.8805	High Similarity	NPC257309
0.8797	High Similarity	NPC199926
0.8797	High Similarity	NPC470605
0.8797	High Similarity	NPC470603
0.8797	High Similarity	NPC82592
0.8797	High Similarity	NPC16082
0.8797	High Similarity	NPC470604
0.8795	High Similarity	NPC63105
0.8795	High Similarity	NPC474345
0.879	High Similarity	NPC183536
0.879	High Similarity	NPC34965
0.8788	High Similarity	NPC38438
0.8788	High Similarity	NPC271385
0.8788	High Similarity	NPC111536
0.8788	High Similarity	NPC5029
0.8788	High Similarity	NPC76128
0.8788	High Similarity	NPC30432
0.8782	High Similarity	NPC179178
0.8782	High Similarity	NPC469619
0.8782	High Similarity	NPC469670
0.878	High Similarity	NPC222455
0.878	High Similarity	NPC259905
0.8766	High Similarity	NPC469700
0.8765	High Similarity	NPC94777
0.8758	High Similarity	NPC210425
0.8758	High Similarity	NPC182045
0.8758	High Similarity	NPC277426
0.8758	High Similarity	NPC280404
0.8758	High Similarity	NPC86373
0.875	High Similarity	NPC245059
0.875	High Similarity	NPC84494
0.8742	High Similarity	NPC265480
0.8742	High Similarity	NPC149368
0.8742	High Similarity	NPC45165
0.8742	High Similarity	NPC301897
0.8734	High Similarity	NPC268950
0.8734	High Similarity	NPC260604
0.8734	High Similarity	NPC108706
0.8734	High Similarity	NPC299435
0.8734	High Similarity	NPC281477
0.8734	High Similarity	NPC78021
0.8734	High Similarity	NPC87304
0.8734	High Similarity	NPC211158
0.8734	High Similarity	NPC106625
0.8727	High Similarity	NPC212748
0.872	High Similarity	NPC298847
0.872	High Similarity	NPC471180
0.8718	High Similarity	NPC270160
0.8718	High Similarity	NPC237440
0.8712	High Similarity	NPC294722
0.8712	High Similarity	NPC72016
0.8712	High Similarity	NPC475979
0.8704	High Similarity	NPC27942
0.8704	High Similarity	NPC473043
0.8704	High Similarity	NPC300537
0.8704	High Similarity	NPC127782
0.8698	High Similarity	NPC164047
0.8698	High Similarity	NPC475161
0.8698	High Similarity	NPC170203
0.8698	High Similarity	NPC470452
0.8698	High Similarity	NPC470453
0.8698	High Similarity	NPC470448
0.8698	High Similarity	NPC477860
0.8693	High Similarity	NPC51106
0.8693	High Similarity	NPC469542
0.8688	High Similarity	NPC177742
0.8688	High Similarity	NPC6985
0.8688	High Similarity	NPC122809
0.8684	High Similarity	NPC90411
0.8683	High Similarity	NPC146803
0.8679	High Similarity	NPC95090
0.8679	High Similarity	NPC99233
0.8679	High Similarity	NPC27408
0.8679	High Similarity	NPC79998
0.8675	High Similarity	NPC254540
0.8675	High Similarity	NPC172807
0.8675	High Similarity	NPC175107
0.8675	High Similarity	NPC471181
0.8675	High Similarity	NPC190003
0.8675	High Similarity	NPC211594
0.8675	High Similarity	NPC472386
0.8671	High Similarity	NPC259767
0.8671	High Similarity	NPC121001
0.8671	High Similarity	NPC259182
0.8671	High Similarity	NPC105827
0.8671	High Similarity	NPC310661
0.8671	High Similarity	NPC88484
0.8667	High Similarity	NPC476771
0.8667	High Similarity	NPC138927
0.8662	High Similarity	NPC96501
0.8659	High Similarity	NPC99957
0.8659	High Similarity	NPC181616
0.8654	High Similarity	NPC240253
0.8654	High Similarity	NPC240622
0.8654	High Similarity	NPC471642
0.8654	High Similarity	NPC471641
0.865	High Similarity	NPC327809
0.865	High Similarity	NPC309025
0.865	High Similarity	NPC243930
0.865	High Similarity	NPC222936
0.865	High Similarity	NPC88043
0.865	High Similarity	NPC88023
0.865	High Similarity	NPC19709
0.865	High Similarity	NPC284960
0.8642	High Similarity	NPC129217
0.8642	High Similarity	NPC282169
0.8642	High Similarity	NPC85707
0.8642	High Similarity	NPC224530
0.8642	High Similarity	NPC48093
0.8642	High Similarity	NPC216496
0.8642	High Similarity	NPC159579
0.8642	High Similarity	NPC101636
0.8642	High Similarity	NPC259957
0.8642	High Similarity	NPC317544
0.8636	High Similarity	NPC27106
0.8636	High Similarity	NPC470932
0.8634	High Similarity	NPC73511
0.8634	High Similarity	NPC308265
0.8631	High Similarity	NPC46958
0.8631	High Similarity	NPC473713
0.8631	High Similarity	NPC475246
0.8627	High Similarity	NPC242756
0.8627	High Similarity	NPC474385
0.8625	High Similarity	NPC295613
0.8625	High Similarity	NPC473657
0.8625	High Similarity	NPC54928
0.8625	High Similarity	NPC206378
0.8623	High Similarity	NPC4390
0.8623	High Similarity	NPC88560
0.8623	High Similarity	NPC472054
0.8623	High Similarity	NPC172033
0.8623	High Similarity	NPC175230
0.8623	High Similarity	NPC213052
0.8616	High Similarity	NPC210003
0.8616	High Similarity	NPC470331
0.8616	High Similarity	NPC143851
0.8616	High Similarity	NPC301233
0.8616	High Similarity	NPC29763
0.8616	High Similarity	NPC83283
0.8616	High Similarity	NPC39360
0.8614	High Similarity	NPC149011
0.8614	High Similarity	NPC235260
0.8614	High Similarity	NPC20505
0.8614	High Similarity	NPC477572
0.8614	High Similarity	NPC210808
0.8614	High Similarity	NPC155763
0.8614	High Similarity	NPC244776
0.8614	High Similarity	NPC477573
0.8614	High Similarity	NPC199079
0.8614	High Similarity	NPC72249
0.8614	High Similarity	NPC477571
0.8614	High Similarity	NPC116864

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 NPC279732 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	882
0.2-0.3	1908
0.3-0.4	2570
0.4-0.5	1913
0.5-0.6	1002
0.6-0.7	393
0.7-0.8	162
0.8-0.85	27
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8606	High Similarity	NPD3818	Discontinued
0.8571	High Similarity	NPD4381	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7054	Approved
0.8402	Intermediate Similarity	NPD6559	Discontinued
0.8393	Intermediate Similarity	NPD7472	Approved
0.8393	Intermediate Similarity	NPD7074	Phase 3
0.8385	Intermediate Similarity	NPD7819	Suspended
0.8344	Intermediate Similarity	NPD2533	Approved
0.8344	Intermediate Similarity	NPD2532	Approved
0.8344	Intermediate Similarity	NPD2534	Approved
0.8343	Intermediate Similarity	NPD6797	Phase 2
0.8312	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7251	Discontinued
0.8246	Intermediate Similarity	NPD7808	Phase 3
0.8225	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD3817	Phase 2
0.8193	Intermediate Similarity	NPD7199	Phase 2
0.8171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD6799	Approved
0.816	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7075	Discontinued
0.8098	Intermediate Similarity	NPD37	Approved
0.8098	Intermediate Similarity	NPD1934	Approved
0.8061	Intermediate Similarity	NPD4965	Approved
0.8061	Intermediate Similarity	NPD4967	Phase 2
0.8061	Intermediate Similarity	NPD4966	Approved
0.8061	Intermediate Similarity	NPD3882	Suspended
0.8049	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5402	Approved
0.7988	Intermediate Similarity	NPD6801	Discontinued
0.7988	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4380	Phase 2
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7964	Intermediate Similarity	NPD6234	Discontinued
0.7953	Intermediate Similarity	NPD7228	Approved
0.7941	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6166	Phase 2
0.7941	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD2801	Approved
0.7929	Intermediate Similarity	NPD6232	Discontinued
0.7917	Intermediate Similarity	NPD5494	Approved
0.7907	Intermediate Similarity	NPD5844	Phase 1
0.7886	Intermediate Similarity	NPD8312	Approved
0.7886	Intermediate Similarity	NPD8313	Approved
0.787	Intermediate Similarity	NPD6959	Discontinued
0.7862	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD1465	Phase 2
0.7824	Intermediate Similarity	NPD3787	Discontinued
0.7824	Intermediate Similarity	NPD5711	Approved
0.7824	Intermediate Similarity	NPD5710	Approved
0.7818	Intermediate Similarity	NPD7411	Suspended
0.7799	Intermediate Similarity	NPD2800	Approved
0.7798	Intermediate Similarity	NPD3749	Approved
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.7791	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5403	Approved
0.7785	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5401	Approved
0.7771	Intermediate Similarity	NPD7240	Approved
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7746	Intermediate Similarity	NPD3751	Discontinued
0.7744	Intermediate Similarity	NPD1653	Approved
0.7736	Intermediate Similarity	NPD1549	Phase 2
0.7727	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2796	Approved
0.7716	Intermediate Similarity	NPD1511	Approved
0.7714	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD920	Approved
0.7679	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD8151	Discontinued
0.7622	Intermediate Similarity	NPD1512	Approved
0.7619	Intermediate Similarity	NPD8455	Phase 2
0.758	Intermediate Similarity	NPD230	Phase 1
0.7578	Intermediate Similarity	NPD1243	Approved
0.7572	Intermediate Similarity	NPD3926	Phase 2
0.7571	Intermediate Similarity	NPD7685	Pre-registration
0.7561	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7435	Discontinued
0.7552	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7783	Phase 2
0.7544	Intermediate Similarity	NPD919	Approved
0.7531	Intermediate Similarity	NPD3750	Approved
0.7529	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7485	Intermediate Similarity	NPD3226	Approved
0.7468	Intermediate Similarity	NPD447	Suspended
0.7453	Intermediate Similarity	NPD2346	Discontinued
0.7439	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3748	Approved
0.7438	Intermediate Similarity	NPD1510	Phase 2
0.7427	Intermediate Similarity	NPD7768	Phase 2
0.7414	Intermediate Similarity	NPD7229	Phase 3
0.7405	Intermediate Similarity	NPD1240	Approved
0.7403	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2935	Discontinued
0.7377	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6832	Phase 2
0.7368	Intermediate Similarity	NPD1091	Approved
0.7363	Intermediate Similarity	NPD8434	Phase 2
0.7362	Intermediate Similarity	NPD1652	Phase 2
0.7358	Intermediate Similarity	NPD1933	Approved
0.7356	Intermediate Similarity	NPD1247	Approved
0.7349	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2799	Discontinued
0.732	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7874	Approved
0.7317	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1607	Approved
0.7278	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7698	Approved
0.7277	Intermediate Similarity	NPD7697	Approved
0.7277	Intermediate Similarity	NPD7696	Phase 3
0.7267	Intermediate Similarity	NPD5353	Approved
0.7259	Intermediate Similarity	NPD7930	Approved
0.7256	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6355	Discontinued
0.725	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7870	Phase 2
0.724	Intermediate Similarity	NPD7871	Phase 2
0.7239	Intermediate Similarity	NPD2344	Approved
0.7225	Intermediate Similarity	NPD5006	Approved
0.7225	Intermediate Similarity	NPD6823	Phase 2
0.7225	Intermediate Similarity	NPD5005	Approved
0.7222	Intermediate Similarity	NPD7033	Discontinued
0.7222	Intermediate Similarity	NPD5953	Discontinued
0.7219	Intermediate Similarity	NPD6534	Approved
0.7219	Intermediate Similarity	NPD6535	Approved
0.7216	Intermediate Similarity	NPD7701	Phase 2
0.7208	Intermediate Similarity	NPD9717	Approved
0.7205	Intermediate Similarity	NPD6651	Approved
0.7178	Intermediate Similarity	NPD6100	Approved
0.7178	Intermediate Similarity	NPD6099	Approved
0.7176	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7584	Approved
0.7158	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2654	Approved
0.7152	Intermediate Similarity	NPD6674	Discontinued
0.715	Intermediate Similarity	NPD8319	Approved
0.715	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD3705	Approved
0.7135	Intermediate Similarity	NPD2403	Approved
0.7134	Intermediate Similarity	NPD7266	Discontinued
0.7117	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7286	Phase 2
0.7107	Intermediate Similarity	NPD7801	Approved
0.7105	Intermediate Similarity	NPD7700	Phase 2
0.7105	Intermediate Similarity	NPD4420	Approved
0.7105	Intermediate Similarity	NPD7699	Phase 2
0.7101	Intermediate Similarity	NPD6273	Approved
0.7097	Intermediate Similarity	NPD1608	Approved
0.7091	Intermediate Similarity	NPD2424	Discontinued
0.7081	Intermediate Similarity	NPD1613	Approved
0.7081	Intermediate Similarity	NPD8150	Discontinued
0.7081	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7583	Approved
0.7076	Intermediate Similarity	NPD7458	Discontinued
0.707	Intermediate Similarity	NPD1203	Approved
0.7066	Intermediate Similarity	NPD2309	Approved
0.7066	Intermediate Similarity	NPD6190	Approved
0.7063	Intermediate Similarity	NPD411	Approved
0.7063	Intermediate Similarity	NPD6798	Discontinued
0.7063	Intermediate Similarity	NPD2313	Discontinued
0.7049	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6843	Phase 3
0.7043	Intermediate Similarity	NPD6841	Approved
0.7043	Intermediate Similarity	NPD6842	Approved
0.7041	Intermediate Similarity	NPD7585	Approved
0.7037	Intermediate Similarity	NPD5124	Phase 1
0.7037	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD422	Phase 1
0.703	Intermediate Similarity	NPD6005	Phase 3
0.703	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5762	Approved
0.703	Intermediate Similarity	NPD6002	Phase 3
0.703	Intermediate Similarity	NPD6004	Phase 3
0.703	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5763	Approved
0.7026	Intermediate Similarity	NPD7999	Approved
0.7025	Intermediate Similarity	NPD1019	Discontinued
0.7025	Intermediate Similarity	NPD5647	Approved
0.7019	Intermediate Similarity	NPD6233	Phase 2
0.7012	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7680	Approved
0.6994	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6653	Approved
0.6984	Remote Similarity	NPD6212	Phase 3

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