NPASS Compound

Structure

NPC88886 OpenBabel07101718242D 28 30 0 0 1 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9128 -2.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9128 -2.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -2.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9128 -0.8364 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 -0.5000 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 8.4128 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4128 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -1.7024 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 5.2437 -0.0933 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 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 4.3301 -0.5000 0.0000 C 0 0 1 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 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9128 -0.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4516 0.8849 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -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 1 8 2 0 0 0 0 2 9 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 20 1 0 0 0 0 7 8 1 0 0 0 0 7 26 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 11 12 2 0 0 0 0 11 14 1 0 0 0 0 12 27 1 0 0 0 0 13 6 1 1 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 14 18 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 17 1 0 0 0 0 16 24 1 1 0 0 0 17 19 1 0 0 0 0 17 25 1 6 0 0 0 18 8 1 1 0 0 0 18 27 1 0 0 0 0 19 26 1 1 0 0 0 19 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.14
Volume:	377.441
LogP:	-0.092
LogD:	-0.163
LogS:	-2.169
# Rotatable Bonds:	6
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.304
Synthetic Accessibility Score:	4.381
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.96
MDCK Permeability:	3.47215318470262e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.295
Human Intestinal Absorption (HIA):	0.716
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.899

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.315
Plasma Protein Binding (PPB):	33.235130310058594%
Volume Distribution (VD):	0.377
Pgp-substrate:	65.35201263427734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	1.335
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.796
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.157
Carcinogencity:	0.872
Eye Corrosion:	0.003
Eye Irritation:	0.051
Respiratory Toxicity:	0.18

Download Data

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

Natural Product: NPC88886

Natural Product ID:	NPC88886
*Common Name:**	1-[(2S,3S)-3-Hydroxy-2-[3-[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyprop-1-En-2-Yl]-2,3-Dihydro-1-Benzofuran-5-Yl]Ethanone
IUPAC Name:	1-[(2S,3S)-3-hydroxy-2-[3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-en-2-yl]-2,3-dihydro-1-benzofuran-5-yl]ethanone
Synonyms:
Standard InCHIKey:	HUIKZEJYJIMIBW-XJBBOAPUSA-N
Standard InCHI:	InChI=1S/C19H24O9/c1-8(7-26-19-17(25)16(24)15(23)13(6-20)28-19)18-14(22)11-5-10(9(2)21)3-4-12(11)27-18/h3-5,13-20,22-25H,1,6-7H2,2H3/t13-,14+,15-,16+,17-,18+,19-/m1/s1
SMILES:	C=C(CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@H]1[C@H](c2cc(ccc2O1)C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2442460
PubChem CID:	73348074
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	1.881	log10CFU/ml	PMID[551988]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	1.927	log10CFU/ml	PMID[551988]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	1.974	log10CFU/ml	PMID[551988]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	2.136	log10CFU/ml	PMID[551988]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	GI	=	17.0	%	PMID[551988]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	16.0	%	PMID[551988]

☑ 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 NPC88886 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	345
0.1-0.2	1293
0.2-0.3	2944
0.3-0.4	7012
0.4-0.5	10831
0.5-0.6	4920
0.6-0.7	5500
0.7-0.8	8150
0.8-0.85	1482
0.85-0.9	211
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC104172
0.958	High Similarity	NPC474044
0.9272	High Similarity	NPC470606
0.9211	High Similarity	NPC470607
0.9205	High Similarity	NPC17521
0.9195	High Similarity	NPC23253
0.9145	High Similarity	NPC23817
0.9139	High Similarity	NPC470604
0.9139	High Similarity	NPC470603
0.9139	High Similarity	NPC470605
0.9097	High Similarity	NPC79908
0.9085	High Similarity	NPC294470
0.9073	High Similarity	NPC108706
0.9073	High Similarity	NPC211158
0.9073	High Similarity	NPC87304
0.9073	High Similarity	NPC268950
0.9073	High Similarity	NPC78021
0.9067	High Similarity	NPC190217
0.9054	High Similarity	NPC218685
0.9034	High Similarity	NPC184053
0.9026	High Similarity	NPC472320
0.9013	High Similarity	NPC99233
0.9	High Similarity	NPC477240
0.9	High Similarity	NPC213723
0.9	High Similarity	NPC106025
0.9	High Similarity	NPC214454
0.8993	High Similarity	NPC199335
0.8986	High Similarity	NPC469700
0.8974	High Similarity	NPC471286
0.8961	High Similarity	NPC73511
0.8954	High Similarity	NPC45165
0.8954	High Similarity	NPC149368
0.8954	High Similarity	NPC265480
0.8947	High Similarity	NPC106625
0.894	High Similarity	NPC318424
0.8926	High Similarity	NPC23084
0.8926	High Similarity	NPC14875
0.8919	High Similarity	NPC291153
0.891	High Similarity	NPC131745
0.891	High Similarity	NPC259834
0.891	High Similarity	NPC93215
0.891	High Similarity	NPC44947
0.8903	High Similarity	NPC200708
0.8903	High Similarity	NPC306978
0.8896	High Similarity	NPC313163
0.8896	High Similarity	NPC156457
0.8896	High Similarity	NPC43638
0.8896	High Similarity	NPC197896
0.8896	High Similarity	NPC161749
0.8896	High Similarity	NPC258035
0.8882	High Similarity	NPC259182
0.8882	High Similarity	NPC259767
0.8882	High Similarity	NPC121001
0.8882	High Similarity	NPC88484
0.8874	High Similarity	NPC38775
0.8874	High Similarity	NPC191154
0.8854	High Similarity	NPC183672
0.8854	High Similarity	NPC179198
0.8854	High Similarity	NPC278419
0.8854	High Similarity	NPC124155
0.8854	High Similarity	NPC257566
0.8854	High Similarity	NPC66087
0.8846	High Similarity	NPC47923
0.8846	High Similarity	NPC303913
0.8839	High Similarity	NPC43761
0.8836	High Similarity	NPC80098
0.8831	High Similarity	NPC170475
0.8831	High Similarity	NPC206378
0.8831	High Similarity	NPC127406
0.8824	High Similarity	NPC470331
0.8816	High Similarity	NPC472423
0.8816	High Similarity	NPC474744
0.8816	High Similarity	NPC134819
0.8816	High Similarity	NPC474772
0.8808	High Similarity	NPC205054
0.88	High Similarity	NPC472339
0.879	High Similarity	NPC125991
0.879	High Similarity	NPC190450
0.8782	High Similarity	NPC271479
0.8776	High Similarity	NPC31081
0.8776	High Similarity	NPC245219
0.8774	High Similarity	NPC6985
0.8774	High Similarity	NPC122809
0.8766	High Similarity	NPC39351
0.8766	High Similarity	NPC97052
0.8766	High Similarity	NPC27408
0.8766	High Similarity	NPC169248
0.8766	High Similarity	NPC26195
0.8766	High Similarity	NPC72649
0.8766	High Similarity	NPC95090
0.8758	High Similarity	NPC473996
0.875	High Similarity	NPC212729
0.875	High Similarity	NPC472421
0.8742	High Similarity	NPC10097
0.8734	High Similarity	NPC91288
0.8718	High Similarity	NPC308265
0.8716	High Similarity	NPC242756
0.8701	High Similarity	NPC29763
0.8701	High Similarity	NPC143851
0.8701	High Similarity	NPC210003
0.8701	High Similarity	NPC39360
0.8701	High Similarity	NPC83283
0.8696	High Similarity	NPC76047
0.8696	High Similarity	NPC135370
0.8696	High Similarity	NPC212748
0.8693	High Similarity	NPC472422
0.8693	High Similarity	NPC472636
0.8693	High Similarity	NPC471676
0.8693	High Similarity	NPC244577
0.8693	High Similarity	NPC472580
0.8693	High Similarity	NPC263384
0.8693	High Similarity	NPC472420
0.8684	High Similarity	NPC227980
0.8684	High Similarity	NPC139966
0.8684	High Similarity	NPC89442
0.8684	High Similarity	NPC307052
0.8681	High Similarity	NPC34456
0.8675	High Similarity	NPC202494
0.8675	High Similarity	NPC91902
0.8675	High Similarity	NPC473133
0.8675	High Similarity	NPC169510
0.8675	High Similarity	NPC47388
0.8675	High Similarity	NPC470670
0.8671	High Similarity	NPC300537
0.8671	High Similarity	NPC127782
0.8671	High Similarity	NPC216752
0.8671	High Similarity	NPC150164
0.8667	High Similarity	NPC297788
0.8662	High Similarity	NPC97285
0.8662	High Similarity	NPC246469
0.8662	High Similarity	NPC271270
0.8662	High Similarity	NPC153342
0.8662	High Similarity	NPC142860
0.8654	High Similarity	NPC288084
0.8654	High Similarity	NPC473512
0.8654	High Similarity	NPC44931
0.8654	High Similarity	NPC108831
0.8654	High Similarity	NPC129827
0.8654	High Similarity	NPC182634
0.8654	High Similarity	NPC60966
0.8654	High Similarity	NPC65003
0.8645	High Similarity	NPC10205
0.8642	High Similarity	NPC235575
0.8636	High Similarity	NPC171651
0.8636	High Similarity	NPC157898
0.8636	High Similarity	NPC327269
0.8636	High Similarity	NPC183536
0.8636	High Similarity	NPC476238
0.8636	High Similarity	NPC161881
0.8636	High Similarity	NPC243171
0.8636	High Similarity	NPC137813
0.8636	High Similarity	NPC31627
0.8636	High Similarity	NPC150123
0.8636	High Similarity	NPC34965
0.8636	High Similarity	NPC477957
0.8636	High Similarity	NPC10807
0.8636	High Similarity	NPC256141
0.8636	High Similarity	NPC244583
0.8636	High Similarity	NPC56232
0.8636	High Similarity	NPC285623
0.8636	High Similarity	NPC35567
0.8634	High Similarity	NPC191653
0.8634	High Similarity	NPC473202
0.8634	High Similarity	NPC5319
0.8627	High Similarity	NPC473966
0.8625	High Similarity	NPC178851
0.8609	High Similarity	NPC474302
0.8609	High Similarity	NPC296377
0.8609	High Similarity	NPC473149
0.8599	High Similarity	NPC111929
0.8599	High Similarity	NPC320283
0.8599	High Similarity	NPC138811
0.8599	High Similarity	NPC41121
0.8599	High Similarity	NPC22062
0.8599	High Similarity	NPC473634
0.8599	High Similarity	NPC472459
0.8599	High Similarity	NPC279732
0.8598	High Similarity	NPC325176
0.8598	High Similarity	NPC475233
0.8592	High Similarity	NPC939
0.8591	High Similarity	NPC171870
0.859	High Similarity	NPC211482
0.859	High Similarity	NPC295613
0.859	High Similarity	NPC307938
0.859	High Similarity	NPC323593
0.859	High Similarity	NPC471405
0.859	High Similarity	NPC261866
0.859	High Similarity	NPC473657
0.859	High Similarity	NPC203500
0.859	High Similarity	NPC476652
0.8589	High Similarity	NPC316539
0.8589	High Similarity	NPC98776
0.8581	High Similarity	NPC472583
0.8581	High Similarity	NPC223701
0.8581	High Similarity	NPC293286
0.8581	High Similarity	NPC7989
0.858	High Similarity	NPC150767
0.858	High Similarity	NPC78734
0.8571	High Similarity	NPC289438
0.8571	High Similarity	NPC471677

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 NPC88886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	818
0.2-0.3	1583
0.3-0.4	2535
0.4-0.5	2059
0.5-0.6	1174
0.6-0.7	475
0.7-0.8	197
0.8-0.85	17
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8896	High Similarity	NPD4381	Clinical (unspecified phase)
0.8634	High Similarity	NPD7804	Clinical (unspecified phase)
0.8589	High Similarity	NPD6559	Discontinued
0.8571	High Similarity	NPD3818	Discontinued
0.8506	High Similarity	NPD4380	Phase 2
0.8418	Intermediate Similarity	NPD7075	Discontinued
0.8354	Intermediate Similarity	NPD7074	Phase 3
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7054	Approved
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8278	Intermediate Similarity	NPD4628	Phase 3
0.8242	Intermediate Similarity	NPD7472	Approved
0.8228	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6797	Phase 2
0.8144	Intermediate Similarity	NPD7251	Discontinued
0.8113	Intermediate Similarity	NPD8455	Phase 2
0.8101	Intermediate Similarity	NPD7411	Suspended
0.8095	Intermediate Similarity	NPD7808	Phase 3
0.8065	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1934	Approved
0.8028	Intermediate Similarity	NPD1091	Approved
0.8026	Intermediate Similarity	NPD1549	Phase 2
0.8012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD6799	Approved
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2424	Discontinued
0.7901	Intermediate Similarity	NPD3882	Suspended
0.7895	Intermediate Similarity	NPD2796	Approved
0.7892	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6166	Phase 2
0.7866	Intermediate Similarity	NPD5494	Approved
0.7862	Intermediate Similarity	NPD7458	Discontinued
0.7857	Intermediate Similarity	NPD5844	Phase 1
0.7848	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD8313	Approved
0.7836	Intermediate Similarity	NPD8312	Approved
0.7834	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6599	Discontinued
0.7771	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2800	Approved
0.7736	Intermediate Similarity	NPD920	Approved
0.7736	Intermediate Similarity	NPD5403	Approved
0.773	Intermediate Similarity	NPD3817	Phase 2
0.7712	Intermediate Similarity	NPD1510	Phase 2
0.7711	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1653	Approved
0.7682	Intermediate Similarity	NPD1240	Approved
0.7679	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2801	Approved
0.7667	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2935	Discontinued
0.7661	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1243	Approved
0.7622	Intermediate Similarity	NPD5402	Approved
0.7616	Intermediate Similarity	NPD7685	Pre-registration
0.7613	Intermediate Similarity	NPD6004	Phase 3
0.7613	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6005	Phase 3
0.7613	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6002	Phase 3
0.761	Intermediate Similarity	NPD5401	Approved
0.761	Intermediate Similarity	NPD2533	Approved
0.761	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2532	Approved
0.761	Intermediate Similarity	NPD2534	Approved
0.7607	Intermediate Similarity	NPD37	Approved
0.7605	Intermediate Similarity	NPD6959	Discontinued
0.7597	Intermediate Similarity	NPD2799	Discontinued
0.7595	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1607	Approved
0.758	Intermediate Similarity	NPD3750	Approved
0.7576	Intermediate Similarity	NPD4966	Approved
0.7576	Intermediate Similarity	NPD4965	Approved
0.7576	Intermediate Similarity	NPD4967	Phase 2
0.7568	Intermediate Similarity	NPD7584	Approved
0.7547	Intermediate Similarity	NPD1511	Approved
0.7543	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6779	Approved
0.7527	Intermediate Similarity	NPD6781	Approved
0.7527	Intermediate Similarity	NPD6778	Approved
0.7527	Intermediate Similarity	NPD6782	Approved
0.7527	Intermediate Similarity	NPD6776	Approved
0.7527	Intermediate Similarity	NPD6777	Approved
0.7527	Intermediate Similarity	NPD6780	Approved
0.7516	Intermediate Similarity	NPD6355	Discontinued
0.7515	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD919	Approved
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD7228	Approved
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7484	Intermediate Similarity	NPD5058	Phase 3
0.7473	Intermediate Similarity	NPD7583	Approved
0.747	Intermediate Similarity	NPD7768	Phase 2
0.7453	Intermediate Similarity	NPD1512	Approved
0.7434	Intermediate Similarity	NPD2313	Discontinued
0.7434	Intermediate Similarity	NPD6798	Discontinued
0.7433	Intermediate Similarity	NPD7585	Approved
0.7425	Intermediate Similarity	NPD3749	Approved
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3226	Approved
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7405	Intermediate Similarity	NPD7435	Discontinued
0.7403	Intermediate Similarity	NPD5124	Phase 1
0.7403	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1933	Approved
0.7401	Intermediate Similarity	NPD8434	Phase 2
0.7396	Intermediate Similarity	NPD1247	Approved
0.7389	Intermediate Similarity	NPD7266	Discontinued
0.7379	Intermediate Similarity	NPD9545	Approved
0.7372	Intermediate Similarity	NPD3748	Approved
0.7365	Intermediate Similarity	NPD9717	Approved
0.7356	Intermediate Similarity	NPD3823	Discontinued
0.7356	Intermediate Similarity	NPD5953	Discontinued
0.7355	Intermediate Similarity	NPD6651	Approved
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7353	Intermediate Similarity	NPD6232	Discontinued
0.7349	Intermediate Similarity	NPD1465	Phase 2
0.7342	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7473	Discontinued
0.7325	Intermediate Similarity	NPD1551	Phase 2
0.732	Intermediate Similarity	NPD3268	Approved
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7697	Approved
0.7312	Intermediate Similarity	NPD7698	Approved
0.7312	Intermediate Similarity	NPD2309	Approved
0.7312	Intermediate Similarity	NPD7696	Phase 3
0.7308	Intermediate Similarity	NPD7097	Phase 1
0.7297	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1652	Phase 2
0.7296	Intermediate Similarity	NPD6674	Discontinued
0.729	Intermediate Similarity	NPD447	Suspended
0.729	Intermediate Similarity	NPD230	Phase 1
0.7285	Intermediate Similarity	NPD2798	Approved
0.7278	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.7273	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD7870	Phase 2
0.7267	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4308	Phase 3
0.7258	Intermediate Similarity	NPD6823	Phase 2
0.7253	Intermediate Similarity	NPD6535	Approved
0.7253	Intermediate Similarity	NPD6534	Approved
0.725	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7701	Phase 2
0.7241	Intermediate Similarity	NPD7286	Phase 2
0.7239	Intermediate Similarity	NPD5049	Phase 3
0.7229	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7783	Phase 2
0.7219	Intermediate Similarity	NPD1203	Approved
0.7219	Intermediate Similarity	NPD2797	Approved
0.7216	Intermediate Similarity	NPD7240	Approved
0.7211	Intermediate Similarity	NPD8151	Discontinued
0.7209	Intermediate Similarity	NPD3926	Phase 2
0.7208	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3887	Approved
0.7205	Intermediate Similarity	NPD2354	Approved
0.7174	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7874	Approved
0.7173	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8651	Approved
0.7152	Intermediate Similarity	NPD5588	Approved
0.7151	Intermediate Similarity	NPD5710	Approved
0.7151	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD5761	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7801	Approved
0.7134	Intermediate Similarity	NPD6273	Approved
0.7133	Intermediate Similarity	NPD1608	Approved
0.7133	Intermediate Similarity	NPD3972	Approved
0.7124	Intermediate Similarity	NPD9494	Approved
0.7115	Intermediate Similarity	NPD3140	Approved
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7115	Intermediate Similarity	NPD3142	Approved
0.7113	Intermediate Similarity	NPD7930	Approved
0.7107	Intermediate Similarity	NPD6100	Approved
0.7107	Intermediate Similarity	NPD6099	Approved
0.7105	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6212	Phase 3
0.7104	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6213	Phase 3
0.7099	Intermediate Similarity	NPD6190	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