NPASS Compound

Structure

NPC175976 OpenBabel07101718192D 31 33 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 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 -0.8660 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 5.1962 -0.0000 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 3.4641 1.0000 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 1.5000 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 -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 0.8660 2.5000 0.0000 C 0 0 0 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 1.7321 1.0000 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 -0.5000 0.0000 C 0 0 1 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 -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 -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 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 12 2 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 19 1 0 0 0 0 12 27 1 0 0 0 0 13 16 2 0 0 0 0 13 28 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 14 30 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 6 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 1 0 0 0 18 21 1 0 0 0 0 18 26 1 6 0 0 0 19 20 2 0 0 0 0 19 31 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 21 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.15
Volume:	418.186
LogP:	0.699
LogD:	0.746
LogS:	-2.325
# Rotatable Bonds:	7
TPSA:	147.3
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	3.71
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.798
MDCK Permeability:	3.0699891794938594e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.476
Plasma Protein Binding (PPB):	75.44152069091797%
Volume Distribution (VD):	0.336
Pgp-substrate:	16.48138999938965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.764
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.582
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.531
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	6.566
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.364
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.137
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.551
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC175976

Natural Product ID:	NPC175976
*Common Name:**	Fortuneanoside B
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[3-hydroxy-2,4-dimethoxy-6-(2-methoxyphenyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	fortuneanoside B
Standard InCHIKey:	YGNDHZPKLQTLBF-LOYVVIFBSA-N
Standard InCHI:	InChI=1S/C21H26O10/c1-27-12-7-5-4-6-10(12)11-8-13(28-2)16(24)20(29-3)19(11)31-21-18(26)17(25)15(23)14(9-22)30-21/h4-8,14-15,17-18,21-26H,9H2,1-3H3/t14-,15-,17+,18-,21+/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2c(OC)c(O)c(cc2c2ccccc2OC)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497444
PubChem CID:	11844492
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
NPO27360	Pyracantha fortuneana	Species	Rosaceae	Eukaryota	fruit	n.a.	n.a.	PMID[16872137]
NPO27360	Pyracantha fortuneana	Species	Rosaceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT741	Individual Protein	Tyrosinase	Homo sapiens	IC50	=	2210000.0	nM	PMID[520638]

☑ 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 NPC175976 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	454
0.1-0.2	1629
0.2-0.3	4309
0.3-0.4	10708
0.4-0.5	7712
0.5-0.6	4411
0.6-0.7	6348
0.7-0.8	5255
0.8-0.85	1170
0.85-0.9	564
0.9-0.95	117
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC190714
0.9857	High Similarity	NPC99515
0.9787	High Similarity	NPC227902
0.9714	High Similarity	NPC473045
0.9714	High Similarity	NPC25292
0.9655	High Similarity	NPC78809
0.9645	High Similarity	NPC475096
0.9643	High Similarity	NPC252169
0.9643	High Similarity	NPC473044
0.9577	High Similarity	NPC125755
0.9571	High Similarity	NPC475084
0.9571	High Similarity	NPC189115
0.9507	High Similarity	NPC277867
0.9507	High Similarity	NPC161700
0.95	High Similarity	NPC469661
0.9452	High Similarity	NPC21902
0.9437	High Similarity	NPC168579
0.9437	High Similarity	NPC76176
0.9437	High Similarity	NPC138227
0.9437	High Similarity	NPC469313
0.9433	High Similarity	NPC469559
0.9375	High Similarity	NPC473480
0.9375	High Similarity	NPC39657
0.9375	High Similarity	NPC15538
0.9371	High Similarity	NPC307466
0.9366	High Similarity	NPC37793
0.9362	High Similarity	NPC471389
0.9357	High Similarity	NPC212770
0.9357	High Similarity	NPC98777
0.9315	High Similarity	NPC472709
0.9315	High Similarity	NPC472710
0.931	High Similarity	NPC166584
0.931	High Similarity	NPC301961
0.9296	High Similarity	NPC5262
0.9296	High Similarity	NPC472714
0.9286	High Similarity	NPC103976
0.9286	High Similarity	NPC326797
0.9286	High Similarity	NPC65530
0.9286	High Similarity	NPC102904
0.9286	High Similarity	NPC176051
0.9286	High Similarity	NPC107551
0.9286	High Similarity	NPC474282
0.9286	High Similarity	NPC59324
0.9247	High Similarity	NPC55158
0.9247	High Similarity	NPC51328
0.9247	High Similarity	NPC286235
0.9231	High Similarity	NPC81638
0.9225	High Similarity	NPC210192
0.922	High Similarity	NPC245207
0.922	High Similarity	NPC471388
0.922	High Similarity	NPC127218
0.922	High Similarity	NPC319647
0.922	High Similarity	NPC25966
0.9214	High Similarity	NPC242028
0.9214	High Similarity	NPC306441
0.9214	High Similarity	NPC16435
0.9214	High Similarity	NPC203230
0.9214	High Similarity	NPC472336
0.9214	High Similarity	NPC472334
0.9214	High Similarity	NPC104167
0.9184	High Similarity	NPC238140
0.9178	High Similarity	NPC280945
0.9178	High Similarity	NPC248132
0.9178	High Similarity	NPC130449
0.9178	High Similarity	NPC270751
0.9172	High Similarity	NPC226540
0.9172	High Similarity	NPC162193
0.9167	High Similarity	NPC187774
0.9167	High Similarity	NPC472712
0.9167	High Similarity	NPC472713
0.9167	High Similarity	NPC118385
0.9167	High Similarity	NPC473046
0.9161	High Similarity	NPC107161
0.9149	High Similarity	NPC470413
0.9149	High Similarity	NPC138738
0.9149	High Similarity	NPC276490
0.9143	High Similarity	NPC121812
0.9143	High Similarity	NPC61946
0.9143	High Similarity	NPC472337
0.9143	High Similarity	NPC112246
0.9143	High Similarity	NPC260898
0.9143	High Similarity	NPC234333
0.9143	High Similarity	NPC112939
0.9143	High Similarity	NPC47398
0.9143	High Similarity	NPC474206
0.9143	High Similarity	NPC470356
0.9143	High Similarity	NPC94750
0.9128	High Similarity	NPC150442
0.9122	High Similarity	NPC473621
0.911	High Similarity	NPC275284
0.911	High Similarity	NPC213074
0.911	High Similarity	NPC193473
0.911	High Similarity	NPC114505
0.911	High Similarity	NPC224674
0.911	High Similarity	NPC31325
0.911	High Similarity	NPC15956
0.9103	High Similarity	NPC178014
0.9103	High Similarity	NPC42716
0.9103	High Similarity	NPC474749
0.9103	High Similarity	NPC11422
0.9097	High Similarity	NPC185307
0.9097	High Similarity	NPC46092
0.9097	High Similarity	NPC470950
0.9091	High Similarity	NPC247291
0.9091	High Similarity	NPC311530
0.9085	High Similarity	NPC22517
0.9085	High Similarity	NPC292487
0.9078	High Similarity	NPC173660
0.9078	High Similarity	NPC270456
0.9078	High Similarity	NPC162659
0.9078	High Similarity	NPC227503
0.9078	High Similarity	NPC474639
0.9078	High Similarity	NPC177035
0.9078	High Similarity	NPC302701
0.9078	High Similarity	NPC230734
0.9078	High Similarity	NPC269091
0.9078	High Similarity	NPC52277
0.9078	High Similarity	NPC248727
0.9078	High Similarity	NPC199459
0.9078	High Similarity	NPC265433
0.9071	High Similarity	NPC251981
0.9071	High Similarity	NPC48863
0.9071	High Similarity	NPC310854
0.9071	High Similarity	NPC107478
0.9071	High Similarity	NPC13745
0.9071	High Similarity	NPC170694
0.9067	High Similarity	NPC159922
0.906	High Similarity	NPC176186
0.906	High Similarity	NPC169404
0.906	High Similarity	NPC53587
0.9054	High Similarity	NPC145979
0.9054	High Similarity	NPC185955
0.9054	High Similarity	NPC214326
0.9054	High Similarity	NPC9933
0.9054	High Similarity	NPC182368
0.9054	High Similarity	NPC469706
0.9054	High Similarity	NPC225815
0.9054	High Similarity	NPC469707
0.9054	High Similarity	NPC218041
0.9054	High Similarity	NPC260781
0.9048	High Similarity	NPC71726
0.9048	High Similarity	NPC478237
0.9034	High Similarity	NPC50250
0.9034	High Similarity	NPC283995
0.9034	High Similarity	NPC93323
0.9034	High Similarity	NPC129417
0.9034	High Similarity	NPC12641
0.9034	High Similarity	NPC280092
0.9034	High Similarity	NPC45257
0.9034	High Similarity	NPC470235
0.9028	High Similarity	NPC476356
0.9028	High Similarity	NPC60249
0.9028	High Similarity	NPC41782
0.9028	High Similarity	NPC48309
0.9021	High Similarity	NPC27495
0.9021	High Similarity	NPC309124
0.9021	High Similarity	NPC259519
0.9021	High Similarity	NPC106944
0.9021	High Similarity	NPC184797
0.9021	High Similarity	NPC160283
0.9021	High Similarity	NPC284464
0.9021	High Similarity	NPC254759
0.902	High Similarity	NPC100936
0.902	High Similarity	NPC1253
0.9014	High Similarity	NPC134260
0.9014	High Similarity	NPC87777
0.9014	High Similarity	NPC262328
0.9014	High Similarity	NPC211549
0.9007	High Similarity	NPC164787
0.9007	High Similarity	NPC195022
0.9007	High Similarity	NPC151224
0.9	High Similarity	NPC294166
0.9	High Similarity	NPC49074
0.9	High Similarity	NPC263064
0.9	High Similarity	NPC115022
0.9	High Similarity	NPC215833
0.9	High Similarity	NPC475840
0.9	High Similarity	NPC132895
0.9	High Similarity	NPC69513
0.9	High Similarity	NPC11060
0.8993	High Similarity	NPC213197
0.8986	High Similarity	NPC106138
0.8973	High Similarity	NPC22150
0.8973	High Similarity	NPC38041
0.8973	High Similarity	NPC476301
0.8973	High Similarity	NPC43508
0.8973	High Similarity	NPC279298
0.8973	High Similarity	NPC18979
0.8966	High Similarity	NPC47633
0.8966	High Similarity	NPC474808
0.8966	High Similarity	NPC477616
0.8966	High Similarity	NPC102044
0.8966	High Similarity	NPC85264
0.8966	High Similarity	NPC472451
0.8958	High Similarity	NPC472711
0.8958	High Similarity	NPC178054
0.8958	High Similarity	NPC76871
0.8951	High Similarity	NPC70682
0.8951	High Similarity	NPC236306
0.8951	High Similarity	NPC292882

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 NPC175976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	880
0.2-0.3	1941
0.3-0.4	2755
0.4-0.5	1620
0.5-0.6	906
0.6-0.7	552
0.7-0.8	117
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD1612	Clinical (unspecified phase)
0.8929	High Similarity	NPD1613	Approved
0.8859	High Similarity	NPD1653	Approved
0.8714	High Similarity	NPD3027	Phase 3
0.8643	High Similarity	NPD1529	Clinical (unspecified phase)
0.8571	High Similarity	NPD1530	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7074	Phase 3
0.8282	Intermediate Similarity	NPD7054	Approved
0.8232	Intermediate Similarity	NPD7472	Approved
0.8221	Intermediate Similarity	NPD3818	Discontinued
0.82	Intermediate Similarity	NPD6674	Discontinued
0.8193	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1091	Approved
0.8125	Intermediate Similarity	NPD4908	Phase 1
0.8125	Intermediate Similarity	NPD6234	Discontinued
0.811	Intermediate Similarity	NPD7228	Approved
0.8072	Intermediate Similarity	NPD6797	Phase 2
0.8067	Intermediate Similarity	NPD7266	Discontinued
0.8056	Intermediate Similarity	NPD2861	Phase 2
0.8038	Intermediate Similarity	NPD1934	Approved
0.8038	Intermediate Similarity	NPD37	Approved
0.8025	Intermediate Similarity	NPD7199	Phase 2
0.8024	Intermediate Similarity	NPD7251	Discontinued
0.8014	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1610	Phase 2
0.8	Intermediate Similarity	NPD4967	Phase 2
0.8	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD4965	Approved
0.7976	Intermediate Similarity	NPD7808	Phase 3
0.795	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6166	Phase 2
0.7879	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2801	Approved
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.7823	Intermediate Similarity	NPD4625	Phase 3
0.7818	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6559	Discontinued
0.773	Intermediate Similarity	NPD1548	Phase 1
0.7687	Intermediate Similarity	NPD3018	Phase 2
0.7655	Intermediate Similarity	NPD4749	Approved
0.7654	Intermediate Similarity	NPD8455	Phase 2
0.7651	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3705	Approved
0.7633	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7240	Approved
0.7546	Intermediate Similarity	NPD1465	Phase 2
0.7545	Intermediate Similarity	NPD3787	Discontinued
0.7534	Intermediate Similarity	NPD2982	Phase 2
0.7534	Intermediate Similarity	NPD2983	Phase 2
0.7515	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3817	Phase 2
0.7468	Intermediate Similarity	NPD5058	Phase 3
0.7466	Intermediate Similarity	NPD2981	Phase 2
0.7455	Intermediate Similarity	NPD3882	Suspended
0.7442	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4060	Phase 1
0.7431	Intermediate Similarity	NPD1357	Approved
0.7425	Intermediate Similarity	NPD5494	Approved
0.7421	Intermediate Similarity	NPD1511	Approved
0.7394	Intermediate Similarity	NPD6671	Approved
0.7389	Intermediate Similarity	NPD1652	Phase 2
0.7376	Intermediate Similarity	NPD5283	Phase 1
0.7368	Intermediate Similarity	NPD3751	Discontinued
0.7362	Intermediate Similarity	NPD4380	Phase 2
0.7357	Intermediate Similarity	NPD228	Approved
0.7356	Intermediate Similarity	NPD7549	Discontinued
0.7345	Intermediate Similarity	NPD6843	Phase 3
0.7345	Intermediate Similarity	NPD6841	Approved
0.7345	Intermediate Similarity	NPD6842	Approved
0.7337	Intermediate Similarity	NPD6232	Discontinued
0.733	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1512	Approved
0.732	Intermediate Similarity	NPD3620	Phase 2
0.732	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7075	Discontinued
0.7303	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7685	Pre-registration
0.729	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4536	Approved
0.729	Intermediate Similarity	NPD4538	Approved
0.7289	Intermediate Similarity	NPD5402	Approved
0.7284	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7157	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8651	Approved
0.7229	Intermediate Similarity	NPD2977	Approved
0.7229	Intermediate Similarity	NPD2978	Approved
0.7209	Intermediate Similarity	NPD7473	Discontinued
0.7208	Intermediate Similarity	NPD1558	Phase 1
0.7207	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7213	Phase 3
0.7205	Intermediate Similarity	NPD7212	Phase 2
0.7204	Intermediate Similarity	NPD7680	Approved
0.7188	Intermediate Similarity	NPD6190	Approved
0.7188	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7843	Approved
0.7181	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5177	Phase 3
0.7169	Intermediate Similarity	NPD3382	Approved
0.7169	Intermediate Similarity	NPD3383	Approved
0.7169	Intermediate Similarity	NPD3384	Approved
0.7162	Intermediate Similarity	NPD422	Phase 1
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7447	Phase 1
0.7152	Intermediate Similarity	NPD4678	Approved
0.7152	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1375	Discontinued
0.7152	Intermediate Similarity	NPD4675	Approved
0.7152	Intermediate Similarity	NPD3540	Phase 1
0.7152	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD2684	Approved
0.7134	Intermediate Similarity	NPD5588	Approved
0.7134	Intermediate Similarity	NPD5960	Phase 3
0.7134	Intermediate Similarity	NPD4108	Discontinued
0.7127	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7819	Suspended
0.7107	Intermediate Similarity	NPD1549	Phase 2
0.7092	Intermediate Similarity	NPD3021	Approved
0.7092	Intermediate Similarity	NPD3022	Approved
0.7091	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4005	Discontinued
0.7089	Intermediate Similarity	NPD6100	Approved
0.7089	Intermediate Similarity	NPD3539	Phase 1
0.7089	Intermediate Similarity	NPD6099	Approved
0.7083	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2677	Approved
0.7079	Intermediate Similarity	NPD8053	Approved
0.7079	Intermediate Similarity	NPD8054	Approved
0.7079	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6798	Discontinued
0.7076	Intermediate Similarity	NPD6959	Discontinued
0.7071	Intermediate Similarity	NPD290	Approved
0.707	Intermediate Similarity	NPD7097	Phase 1
0.7066	Intermediate Similarity	NPD6801	Discontinued
0.7056	Intermediate Similarity	NPD7906	Approved
0.7055	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6355	Discontinued
0.7044	Intermediate Similarity	NPD5762	Approved
0.7044	Intermediate Similarity	NPD5763	Approved
0.7027	Intermediate Similarity	NPD5126	Approved
0.7027	Intermediate Similarity	NPD5125	Phase 3
0.7025	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8313	Approved
0.7022	Intermediate Similarity	NPD8312	Approved
0.7019	Intermediate Similarity	NPD3750	Approved
0.7019	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4628	Phase 3
0.7019	Intermediate Similarity	NPD3892	Phase 2
0.7013	Intermediate Similarity	NPD7095	Approved
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD968	Approved
0.7	Intermediate Similarity	NPD4663	Approved
0.698	Remote Similarity	NPD3496	Discontinued
0.697	Remote Similarity	NPD5403	Approved
0.6962	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3060	Approved
0.6954	Remote Similarity	NPD2489	Approved
0.6954	Remote Similarity	NPD27	Approved
0.6954	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5735	Approved
0.6941	Remote Similarity	NPD7768	Phase 2
0.6928	Remote Similarity	NPD6584	Phase 3
0.6918	Remote Similarity	NPD7033	Discontinued
0.6914	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4110	Phase 3
0.6914	Remote Similarity	NPD6331	Phase 2
0.6913	Remote Similarity	NPD6516	Phase 2
0.6913	Remote Similarity	NPD5846	Approved
0.6908	Remote Similarity	NPD6696	Suspended
0.6905	Remote Similarity	NPD7411	Suspended
0.6901	Remote Similarity	NPD4055	Discovery
0.6897	Remote Similarity	NPD2970	Approved
0.6897	Remote Similarity	NPD2969	Approved
0.6894	Remote Similarity	NPD2424	Discontinued
0.689	Remote Similarity	NPD6799	Approved
0.689	Remote Similarity	NPD1774	Approved
0.6882	Remote Similarity	NPD2563	Approved
0.6882	Remote Similarity	NPD2560	Approved
0.6879	Remote Similarity	NPD8127	Discontinued
0.6879	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2238	Phase 2
0.6875	Remote Similarity	NPD2796	Approved
0.6875	Remote Similarity	NPD2935	Discontinued
0.6875	Remote Similarity	NPD3454	Phase 3
0.6862	Remote Similarity	NPD6776	Approved
0.6862	Remote Similarity	NPD6782	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