NPASS Compound

Structure

NPC190714 OpenBabel07101719142D 30 32 0 0 1 0 0 0 0 0999 V2000 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 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 -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 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 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 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 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 27 1 0 0 0 0 2 28 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 11 29 1 0 0 0 0 12 16 2 0 0 0 0 12 27 1 0 0 0 0 13 16 1 0 0 0 0 13 28 1 0 0 0 0 14 8 1 6 0 0 0 14 17 1 0 0 0 0 14 30 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 19 1 0 0 0 0 18 25 1 6 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 29 1 6 0 0 0 20 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.14
Volume:	400.89
LogP:	0.373
LogD:	0.464
LogS:	-2.745
# Rotatable Bonds:	6
TPSA:	158.3
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.372
Synthetic Accessibility Score:	3.685
Fsp3:	0.4
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:	-6.301
MDCK Permeability:	2.2658407033304684e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.204
Human Intestinal Absorption (HIA):	0.556
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.839

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.31
Plasma Protein Binding (PPB):	89.2213363647461%
Volume Distribution (VD):	0.396
Pgp-substrate:	13.55585765838623%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.326
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.482
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.222
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.436
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	7.101
Half-life (T1/2):	0.93

ADMET: Toxicity

hERG Blockers:	0.313
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.085
AMES Toxicity:	0.279
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.896
Carcinogencity:	0.079
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC190714

Natural Product ID:	NPC190714
*Common Name:**	Fortuneanoside D
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[2-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	fortuneanoside D
Standard InCHIKey:	IFVMNCUQIWXERP-LWUBGYQZSA-N
Standard InCHI:	InChI=1S/C20H24O10/c1-27-12-6-9(7-13(28-2)16(12)23)10-4-3-5-11(15(10)22)29-20-19(26)18(25)17(24)14(8-21)30-20/h3-7,14,17-26H,8H2,1-2H3/t14-,17-,18+,19-,20-/m1/s1
SMILES:	COc1cc(cc(c1O)OC)c1cccc(c1O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526100
PubChem CID:	11844493
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	=	70000.0	nM	PMID[540204]

☑ 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 NPC190714 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	447
0.1-0.2	1588
0.2-0.3	4159
0.3-0.4	10414
0.4-0.5	8009
0.5-0.6	4272
0.6-0.7	6350
0.7-0.8	5387
0.8-0.85	1288
0.85-0.9	603
0.9-0.95	157
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC99515
0.9857	High Similarity	NPC175976
0.9855	High Similarity	NPC25292
0.9855	High Similarity	NPC473045
0.9784	High Similarity	NPC475096
0.9783	High Similarity	NPC473044
0.9714	High Similarity	NPC125755
0.971	High Similarity	NPC475084
0.971	High Similarity	NPC189115
0.9645	High Similarity	NPC227902
0.9643	High Similarity	NPC161700
0.9643	High Similarity	NPC277867
0.9638	High Similarity	NPC469661
0.9583	High Similarity	NPC21902
0.9571	High Similarity	NPC76176
0.9571	High Similarity	NPC168579
0.9571	High Similarity	NPC138227
0.9571	High Similarity	NPC469313
0.9568	High Similarity	NPC469559
0.9517	High Similarity	NPC78809
0.9507	High Similarity	NPC473480
0.9507	High Similarity	NPC15538
0.9507	High Similarity	NPC39657
0.95	High Similarity	NPC37793
0.95	High Similarity	NPC252169
0.9493	High Similarity	NPC212770
0.9493	High Similarity	NPC98777
0.9444	High Similarity	NPC472709
0.9444	High Similarity	NPC472710
0.9429	High Similarity	NPC472714
0.9429	High Similarity	NPC5262
0.942	High Similarity	NPC65530
0.942	High Similarity	NPC59324
0.9375	High Similarity	NPC51328
0.9375	High Similarity	NPC286235
0.9375	High Similarity	NPC55158
0.9362	High Similarity	NPC81638
0.9357	High Similarity	NPC210192
0.9348	High Similarity	NPC306441
0.9348	High Similarity	NPC203230
0.9348	High Similarity	NPC16435
0.9348	High Similarity	NPC242028
0.9306	High Similarity	NPC270751
0.9306	High Similarity	NPC248132
0.9306	High Similarity	NPC130449
0.9306	High Similarity	NPC280945
0.9296	High Similarity	NPC472713
0.9296	High Similarity	NPC187774
0.9296	High Similarity	NPC473046
0.9296	High Similarity	NPC118385
0.9296	High Similarity	NPC472712
0.9281	High Similarity	NPC138738
0.9281	High Similarity	NPC470413
0.9275	High Similarity	NPC234333
0.9275	High Similarity	NPC260898
0.9275	High Similarity	NPC474206
0.9275	High Similarity	NPC94750
0.9275	High Similarity	NPC47398
0.9275	High Similarity	NPC121812
0.9275	High Similarity	NPC112939
0.9275	High Similarity	NPC112246
0.9275	High Similarity	NPC61946
0.9275	High Similarity	NPC470356
0.9252	High Similarity	NPC150442
0.9247	High Similarity	NPC473621
0.9236	High Similarity	NPC224674
0.9236	High Similarity	NPC275284
0.9236	High Similarity	NPC15956
0.9236	High Similarity	NPC193473
0.9236	High Similarity	NPC31325
0.9236	High Similarity	NPC114505
0.9236	High Similarity	NPC213074
0.9231	High Similarity	NPC307466
0.9225	High Similarity	NPC46092
0.9225	High Similarity	NPC470950
0.9225	High Similarity	NPC185307
0.922	High Similarity	NPC471389
0.9214	High Similarity	NPC292487
0.9214	High Similarity	NPC22517
0.9209	High Similarity	NPC199459
0.9209	High Similarity	NPC269091
0.9209	High Similarity	NPC302701
0.9209	High Similarity	NPC227503
0.9209	High Similarity	NPC474639
0.9209	High Similarity	NPC265433
0.9209	High Similarity	NPC248727
0.9209	High Similarity	NPC162659
0.9209	High Similarity	NPC270456
0.9209	High Similarity	NPC52277
0.9209	High Similarity	NPC230734
0.9209	High Similarity	NPC177035
0.9203	High Similarity	NPC251981
0.9203	High Similarity	NPC107478
0.9203	High Similarity	NPC170694
0.9203	High Similarity	NPC48863
0.9203	High Similarity	NPC13745
0.9184	High Similarity	NPC176186
0.9184	High Similarity	NPC169404
0.9184	High Similarity	NPC53587
0.9178	High Similarity	NPC9933
0.9178	High Similarity	NPC260781
0.9178	High Similarity	NPC214326
0.9178	High Similarity	NPC185955
0.9178	High Similarity	NPC182368
0.9178	High Similarity	NPC225815
0.9178	High Similarity	NPC469707
0.9178	High Similarity	NPC469706
0.9178	High Similarity	NPC145979
0.9178	High Similarity	NPC218041
0.9172	High Similarity	NPC301961
0.9172	High Similarity	NPC166584
0.9161	High Similarity	NPC470235
0.9161	High Similarity	NPC283995
0.9161	High Similarity	NPC129417
0.9155	High Similarity	NPC48309
0.9155	High Similarity	NPC41782
0.9155	High Similarity	NPC476356
0.9155	High Similarity	NPC60249
0.9149	High Similarity	NPC106944
0.9149	High Similarity	NPC184797
0.9149	High Similarity	NPC309124
0.9143	High Similarity	NPC103976
0.9143	High Similarity	NPC326797
0.9143	High Similarity	NPC211549
0.9143	High Similarity	NPC102904
0.9143	High Similarity	NPC107551
0.9143	High Similarity	NPC87777
0.9143	High Similarity	NPC262328
0.9143	High Similarity	NPC474282
0.9143	High Similarity	NPC134260
0.9143	High Similarity	NPC176051
0.9137	High Similarity	NPC151224
0.9137	High Similarity	NPC164787
0.913	High Similarity	NPC475840
0.913	High Similarity	NPC11060
0.913	High Similarity	NPC215833
0.913	High Similarity	NPC69513
0.913	High Similarity	NPC132895
0.913	High Similarity	NPC49074
0.913	High Similarity	NPC115022
0.913	High Similarity	NPC294166
0.913	High Similarity	NPC263064
0.911	High Similarity	NPC106138
0.9097	High Similarity	NPC43508
0.9097	High Similarity	NPC18979
0.9097	High Similarity	NPC279298
0.9097	High Similarity	NPC22150
0.9097	High Similarity	NPC38041
0.9097	High Similarity	NPC476301
0.9085	High Similarity	NPC472711
0.9085	High Similarity	NPC178054
0.9085	High Similarity	NPC76871
0.9078	High Similarity	NPC473739
0.9078	High Similarity	NPC25966
0.9078	High Similarity	NPC127218
0.9078	High Similarity	NPC471388
0.9078	High Similarity	NPC232164
0.9078	High Similarity	NPC319647
0.9078	High Similarity	NPC70682
0.9078	High Similarity	NPC236306
0.9078	High Similarity	NPC245207
0.9078	High Similarity	NPC260741
0.9071	High Similarity	NPC164857
0.9071	High Similarity	NPC470802
0.9071	High Similarity	NPC25695
0.9071	High Similarity	NPC472336
0.9071	High Similarity	NPC472334
0.9071	High Similarity	NPC234952
0.9071	High Similarity	NPC172818
0.9071	High Similarity	NPC104167
0.9065	High Similarity	NPC317380
0.9065	High Similarity	NPC478085
0.9065	High Similarity	NPC87696
0.9065	High Similarity	NPC476411
0.9065	High Similarity	NPC187194
0.9058	High Similarity	NPC160991
0.9058	High Similarity	NPC126029
0.9058	High Similarity	NPC201587
0.9058	High Similarity	NPC85799
0.9058	High Similarity	NPC15658
0.9058	High Similarity	NPC127624
0.9058	High Similarity	NPC78770
0.9058	High Similarity	NPC184447
0.9058	High Similarity	NPC303422
0.9058	High Similarity	NPC26080
0.9058	High Similarity	NPC253105
0.9058	High Similarity	NPC261619
0.9058	High Similarity	NPC86655
0.9058	High Similarity	NPC219876
0.9058	High Similarity	NPC7903
0.9058	High Similarity	NPC35932
0.9058	High Similarity	NPC162093
0.9058	High Similarity	NPC185604
0.9058	High Similarity	NPC61477
0.9058	High Similarity	NPC16208
0.9058	High Similarity	NPC165686
0.9058	High Similarity	NPC299144
0.9058	High Similarity	NPC202762
0.9058	High Similarity	NPC470270
0.9054	High Similarity	NPC302610

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 NPC190714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	864
0.2-0.3	1888
0.3-0.4	2722
0.4-0.5	1664
0.5-0.6	918
0.6-0.7	582
0.7-0.8	134
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9058	High Similarity	NPD1612	Clinical (unspecified phase)
0.9058	High Similarity	NPD1613	Approved
0.8841	High Similarity	NPD3027	Phase 3
0.8768	High Similarity	NPD1529	Clinical (unspecified phase)
0.8725	High Similarity	NPD1653	Approved
0.8696	High Similarity	NPD1530	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7074	Phase 3
0.8385	Intermediate Similarity	NPD7054	Approved
0.8333	Intermediate Similarity	NPD7472	Approved
0.8323	Intermediate Similarity	NPD3818	Discontinued
0.8311	Intermediate Similarity	NPD6674	Discontinued
0.8261	Intermediate Similarity	NPD1091	Approved
0.8239	Intermediate Similarity	NPD4908	Phase 1
0.8228	Intermediate Similarity	NPD6234	Discontinued
0.821	Intermediate Similarity	NPD7228	Approved
0.8176	Intermediate Similarity	NPD7266	Discontinued
0.8171	Intermediate Similarity	NPD6797	Phase 2
0.8141	Intermediate Similarity	NPD1934	Approved
0.8141	Intermediate Similarity	NPD37	Approved
0.8129	Intermediate Similarity	NPD1610	Phase 2
0.8125	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7199	Phase 2
0.8121	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD4967	Phase 2
0.8101	Intermediate Similarity	NPD4966	Approved
0.8101	Intermediate Similarity	NPD4965	Approved
0.8072	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7808	Phase 3
0.805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4625	Phase 3
0.7917	Intermediate Similarity	NPD2861	Phase 2
0.7914	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6559	Discontinued
0.7842	Intermediate Similarity	NPD1548	Phase 1
0.7793	Intermediate Similarity	NPD3018	Phase 2
0.7762	Intermediate Similarity	NPD4749	Approved
0.7755	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2801	Approved
0.775	Intermediate Similarity	NPD8455	Phase 2
0.7746	Intermediate Similarity	NPD3705	Approved
0.7725	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7712	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7240	Approved
0.764	Intermediate Similarity	NPD1465	Phase 2
0.7639	Intermediate Similarity	NPD2982	Phase 2
0.7639	Intermediate Similarity	NPD2983	Phase 2
0.7607	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3817	Phase 2
0.7569	Intermediate Similarity	NPD2981	Phase 2
0.7564	Intermediate Similarity	NPD5058	Phase 3
0.7546	Intermediate Similarity	NPD3882	Suspended
0.7535	Intermediate Similarity	NPD1357	Approved
0.7533	Intermediate Similarity	NPD4060	Phase 1
0.753	Intermediate Similarity	NPD3787	Discontinued
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1511	Approved
0.7484	Intermediate Similarity	NPD1652	Phase 2
0.7482	Intermediate Similarity	NPD5283	Phase 1
0.7464	Intermediate Similarity	NPD228	Approved
0.7453	Intermediate Similarity	NPD4380	Phase 2
0.7429	Intermediate Similarity	NPD6842	Approved
0.7429	Intermediate Similarity	NPD6841	Approved
0.7429	Intermediate Similarity	NPD6843	Phase 3
0.7425	Intermediate Similarity	NPD6232	Discontinued
0.7421	Intermediate Similarity	NPD1512	Approved
0.7417	Intermediate Similarity	NPD3620	Phase 2
0.7417	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7075	Discontinued
0.7386	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4538	Approved
0.7386	Intermediate Similarity	NPD4536	Approved
0.7384	Intermediate Similarity	NPD7685	Pre-registration
0.7376	Intermediate Similarity	NPD7157	Approved
0.7375	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5124	Phase 1
0.7368	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7348	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8651	Approved
0.7317	Intermediate Similarity	NPD2978	Approved
0.7317	Intermediate Similarity	NPD2977	Approved
0.7314	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5494	Approved
0.7303	Intermediate Similarity	NPD1558	Phase 1
0.7296	Intermediate Similarity	NPD7212	Phase 2
0.7296	Intermediate Similarity	NPD7213	Phase 3
0.7294	Intermediate Similarity	NPD7473	Discontinued
0.7286	Intermediate Similarity	NPD7843	Approved
0.7283	Intermediate Similarity	NPD7680	Approved
0.7279	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5177	Phase 3
0.726	Intermediate Similarity	NPD422	Phase 1
0.7254	Intermediate Similarity	NPD6671	Approved
0.725	Intermediate Similarity	NPD7447	Phase 1
0.725	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2684	Approved
0.7244	Intermediate Similarity	NPD3540	Phase 1
0.7244	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1375	Discontinued
0.7244	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7549	Discontinued
0.7239	Intermediate Similarity	NPD4678	Approved
0.7239	Intermediate Similarity	NPD4675	Approved
0.7226	Intermediate Similarity	NPD4108	Discontinued
0.7226	Intermediate Similarity	NPD5960	Phase 3
0.7226	Intermediate Similarity	NPD5588	Approved
0.7212	Intermediate Similarity	NPD7819	Suspended
0.7212	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1549	Phase 2
0.7194	Intermediate Similarity	NPD3022	Approved
0.7194	Intermediate Similarity	NPD3021	Approved
0.7179	Intermediate Similarity	NPD3539	Phase 1
0.7179	Intermediate Similarity	NPD6099	Approved
0.7179	Intermediate Similarity	NPD6100	Approved
0.7178	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4005	Discontinued
0.7174	Intermediate Similarity	NPD290	Approved
0.7171	Intermediate Similarity	NPD6798	Discontinued
0.717	Intermediate Similarity	NPD6190	Approved
0.717	Intermediate Similarity	NPD2677	Approved
0.7169	Intermediate Similarity	NPD5402	Approved
0.7169	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7097	Phase 1
0.716	Intermediate Similarity	NPD6959	Discontinued
0.7159	Intermediate Similarity	NPD8053	Approved
0.7159	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8054	Approved
0.7152	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD5762	Approved
0.7134	Intermediate Similarity	NPD5763	Approved
0.7123	Intermediate Similarity	NPD5125	Phase 3
0.7123	Intermediate Similarity	NPD5126	Approved
0.7115	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3892	Phase 2
0.7107	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3750	Approved
0.7107	Intermediate Similarity	NPD4628	Phase 3
0.7105	Intermediate Similarity	NPD7095	Approved
0.7102	Intermediate Similarity	NPD8312	Approved
0.7102	Intermediate Similarity	NPD8313	Approved
0.7095	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5403	Approved
0.7051	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3383	Approved
0.7048	Intermediate Similarity	NPD3384	Approved
0.7048	Intermediate Similarity	NPD3382	Approved
0.7047	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3060	Approved
0.7039	Intermediate Similarity	NPD7906	Approved
0.7035	Intermediate Similarity	NPD27	Approved
0.7035	Intermediate Similarity	NPD2489	Approved
0.7032	Intermediate Similarity	NPD5735	Approved
0.7024	Intermediate Similarity	NPD7768	Phase 2
0.702	Intermediate Similarity	NPD6584	Phase 3
0.7017	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6233	Phase 2
0.7007	Intermediate Similarity	NPD5846	Approved
0.7007	Intermediate Similarity	NPD6516	Phase 2
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6331	Phase 2
0.7	Intermediate Similarity	NPD4110	Phase 3
0.6988	Remote Similarity	NPD7411	Suspended
0.6983	Remote Similarity	NPD4663	Approved
0.6982	Remote Similarity	NPD4055	Discovery
0.6981	Remote Similarity	NPD2424	Discontinued
0.6977	Remote Similarity	NPD2969	Approved
0.6977	Remote Similarity	NPD2970	Approved
0.6975	Remote Similarity	NPD1774	Approved
0.6975	Remote Similarity	NPD6799	Approved
0.6968	Remote Similarity	NPD2238	Phase 2
0.6968	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2563	Approved
0.6964	Remote Similarity	NPD2560	Approved
0.6962	Remote Similarity	NPD2796	Approved
0.6959	Remote Similarity	NPD8127	Discontinued
0.6937	Remote Similarity	NPD4237	Approved
0.6937	Remote Similarity	NPD4236	Phase 3
0.6937	Remote Similarity	NPD4162	Approved
0.6936	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4123	Phase 3
0.6933	Remote Similarity	NPD5401	Approved
0.6933	Remote Similarity	NPD4160	Clinical (unspecified phase)

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