NPASS Compound

Structure

NPC6985 OpenBabel07101718312D 32 34 0 0 1 0 0 0 0 0999 V2000 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 4.0000 0.0000 C 0 0 0 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 -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 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 1.0000 0.0000 C 0 0 2 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 7.7942 4.5000 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 2.5981 4.5000 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 -0.8660 4.5000 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 30 1 0 0 0 0 2 5 1 0 0 0 0 2 11 2 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 7 1 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 16 2 0 0 0 0 10 23 1 0 0 0 0 12 24 1 0 0 0 0 13 30 1 0 0 0 0 14 18 1 0 0 0 0 14 25 2 0 0 0 0 15 18 2 0 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 16 31 1 0 0 0 0 17 10 1 6 0 0 0 17 19 1 0 0 0 0 17 32 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 1 0 0 0 20 21 1 0 0 0 0 20 28 2 0 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 31 1 6 0 0 0 22 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.14
Volume:	430.209
LogP:	1.178
LogD:	0.657
LogS:	-1.885
# Rotatable Bonds:	8
TPSA:	162.98
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	3.943
Fsp3:	0.364
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:	-6.074
MDCK Permeability:	5.336883987183683e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.488
20% Bioavailability (F20%):	0.245
30% Bioavailability (F30%):	0.893

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.346
Plasma Protein Binding (PPB):	75.79693603515625%
Volume Distribution (VD):	1.071
Pgp-substrate:	15.582914352416992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.823
CYP2D6-inhibitor:	0.399
CYP2D6-substrate:	0.572
CYP3A4-inhibitor:	0.063
CYP3A4-substrate:	0.095

ADMET: Excretion

Clearance (CL):	8.74
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.469
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.451
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.201
Carcinogencity:	0.121
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC6985

Natural Product ID:	NPC6985
*Common Name:**	2',4,6'-Trihydroxy-4'-Methoxydihydrochalcone 2'-O-Beta-D-Ribohexo-3-Ulopyranoside
IUPAC Name:	(2S,3S,5R,6R)-3,5-dihydroxy-2-[3-hydroxy-2-[3-(4-hydroxyphenyl)propanoyl]-5-methoxyphenoxy]-6-(hydroxymethyl)oxan-4-one
Synonyms:	Asebogenin 2'-O-beta-D-ribohexo-3-ulopyranoside
Standard InCHIKey:	NTMBWMBWUUMBLE-JHMKDJTOSA-N
Standard InCHI:	InChI=1S/C22H24O10/c1-30-13-8-15(26)18(14(25)7-4-11-2-5-12(24)6-3-11)16(9-13)31-22-21(29)20(28)19(27)17(10-23)32-22/h2-3,5-6,8-9,17,19,21-24,26-27,29H,4,7,10H2,1H3/t17-,19-,21-,22-/m1/s1
SMILES:	COc1cc(c(C(=O)CCc2ccc(cc2)O)c(c1)O[C@H]1[C@@H](C(=O)[C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482049
PubChem CID:	11247865
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-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
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31809052]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13961	Pieris japonica	Species	Ericaceae	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
NON-MOLECULAR	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	16.41	10'-3cpm	PMID[517569]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	35.0	10'-3cpm	PMID[517569]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	34.21	10'-3cpm	PMID[517569]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	32.04	10'-3cpm	PMID[517569]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	26.73	10'-3cpm	PMID[517569]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	38.28	10'-3cpm	PMID[517569]

☑ 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 NPC6985 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	374
0.1-0.2	1457
0.2-0.3	3529
0.3-0.4	8516
0.4-0.5	9709
0.5-0.6	4535
0.6-0.7	5284
0.7-0.8	5520
0.8-0.85	2554
0.85-0.9	985
0.9-0.95	213
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC106625
0.9737	High Similarity	NPC153342
0.9735	High Similarity	NPC182634
0.9735	High Similarity	NPC108831
0.9733	High Similarity	NPC99233
0.9732	High Similarity	NPC121001
0.9732	High Similarity	NPC259182
0.9671	High Similarity	NPC320283
0.9671	High Similarity	NPC41121
0.9671	High Similarity	NPC472459
0.9671	High Similarity	NPC111929
0.9669	High Similarity	NPC127406
0.9669	High Similarity	NPC203500
0.9669	High Similarity	NPC307938
0.9669	High Similarity	NPC323593
0.9669	High Similarity	NPC206378
0.961	High Similarity	NPC27942
0.961	High Similarity	NPC259834
0.961	High Similarity	NPC131745
0.9608	High Similarity	NPC187379
0.9605	High Similarity	NPC135391
0.9605	High Similarity	NPC78263
0.9605	High Similarity	NPC23817
0.9605	High Similarity	NPC197304
0.9605	High Similarity	NPC133671
0.9605	High Similarity	NPC77672
0.9605	High Similarity	NPC54802
0.9605	High Similarity	NPC43638
0.9603	High Similarity	NPC97052
0.9603	High Similarity	NPC95090
0.9603	High Similarity	NPC27408
0.9603	High Similarity	NPC72649
0.9603	High Similarity	NPC169248
0.9603	High Similarity	NPC26195
0.9603	High Similarity	NPC39351
0.96	High Similarity	NPC259767
0.96	High Similarity	NPC88484
0.9548	High Similarity	NPC183672
0.9548	High Similarity	NPC179198
0.9548	High Similarity	NPC66087
0.9548	High Similarity	NPC278419
0.9545	High Similarity	NPC476215
0.9545	High Similarity	NPC249281
0.9545	High Similarity	NPC246943
0.9545	High Similarity	NPC259957
0.9545	High Similarity	NPC253788
0.9545	High Similarity	NPC139320
0.9545	High Similarity	NPC282169
0.9545	High Similarity	NPC173582
0.9545	High Similarity	NPC276377
0.9545	High Similarity	NPC129217
0.9545	High Similarity	NPC159579
0.9545	High Similarity	NPC48093
0.9545	High Similarity	NPC116458
0.9545	High Similarity	NPC181465
0.9545	High Similarity	NPC163242
0.9545	High Similarity	NPC215710
0.9545	High Similarity	NPC473438
0.9545	High Similarity	NPC224530
0.9545	High Similarity	NPC265885
0.9545	High Similarity	NPC216496
0.9545	High Similarity	NPC85707
0.9542	High Similarity	NPC73511
0.9539	High Similarity	NPC170475
0.9536	High Similarity	NPC210003
0.9536	High Similarity	NPC83283
0.9536	High Similarity	NPC39360
0.9536	High Similarity	NPC143851
0.9536	High Similarity	NPC29763
0.9484	High Similarity	NPC150164
0.9484	High Similarity	NPC240306
0.9481	High Similarity	NPC136761
0.9481	High Similarity	NPC304741
0.9481	High Similarity	NPC246469
0.9481	High Similarity	NPC142860
0.9481	High Similarity	NPC97285
0.9481	High Similarity	NPC471079
0.9481	High Similarity	NPC271270
0.9481	High Similarity	NPC470405
0.9477	High Similarity	NPC156457
0.9477	High Similarity	NPC65003
0.9477	High Similarity	NPC60966
0.9477	High Similarity	NPC161749
0.9477	High Similarity	NPC197896
0.9477	High Similarity	NPC473512
0.9477	High Similarity	NPC44931
0.9477	High Similarity	NPC313163
0.9477	High Similarity	NPC288084
0.9477	High Similarity	NPC258035
0.9477	High Similarity	NPC129827
0.9467	High Similarity	NPC477240
0.9467	High Similarity	NPC214454
0.9467	High Similarity	NPC106025
0.9467	High Similarity	NPC191154
0.9463	High Similarity	NPC199335
0.9423	High Similarity	NPC121703
0.9419	High Similarity	NPC470125
0.9419	High Similarity	NPC135846
0.9419	High Similarity	NPC64305
0.9419	High Similarity	NPC170052
0.9419	High Similarity	NPC303913
0.9419	High Similarity	NPC297987
0.9416	High Similarity	NPC308265
0.9416	High Similarity	NPC104677
0.9416	High Similarity	NPC138811
0.9416	High Similarity	NPC473634
0.9416	High Similarity	NPC22062
0.9412	High Similarity	NPC149368
0.9412	High Similarity	NPC45165
0.9412	High Similarity	NPC265480
0.9408	High Similarity	NPC268950
0.9408	High Similarity	NPC108706
0.9408	High Similarity	NPC211158
0.9408	High Similarity	NPC78021
0.9408	High Similarity	NPC87304
0.9404	High Similarity	NPC190217
0.9404	High Similarity	NPC134819
0.9396	High Similarity	NPC176869
0.9396	High Similarity	NPC211466
0.9396	High Similarity	NPC44721
0.9396	High Similarity	NPC40086
0.9396	High Similarity	NPC122828
0.9396	High Similarity	NPC3779
0.9396	High Similarity	NPC23084
0.9396	High Similarity	NPC476182
0.9363	High Similarity	NPC72016
0.9363	High Similarity	NPC139060
0.9363	High Similarity	NPC287889
0.9363	High Similarity	NPC135358
0.9359	High Similarity	NPC190450
0.9359	High Similarity	NPC44947
0.9359	High Similarity	NPC127782
0.9359	High Similarity	NPC300537
0.9355	High Similarity	NPC473623
0.9355	High Similarity	NPC271479
0.9355	High Similarity	NPC200708
0.9355	High Similarity	NPC472320
0.9351	High Similarity	NPC122809
0.9346	High Similarity	NPC470603
0.9346	High Similarity	NPC470605
0.9346	High Similarity	NPC470604
0.9338	High Similarity	NPC213723
0.9308	High Similarity	NPC270578
0.9308	High Similarity	NPC5319
0.9308	High Similarity	NPC52382
0.9304	High Similarity	NPC256188
0.9304	High Similarity	NPC476470
0.9304	High Similarity	NPC12013
0.9304	High Similarity	NPC11432
0.9304	High Similarity	NPC32641
0.9304	High Similarity	NPC64425
0.9304	High Similarity	NPC189564
0.9304	High Similarity	NPC221342
0.9304	High Similarity	NPC142142
0.9304	High Similarity	NPC477613
0.9304	High Similarity	NPC203145
0.9304	High Similarity	NPC186816
0.9299	High Similarity	NPC257566
0.9299	High Similarity	NPC124155
0.9299	High Similarity	NPC80068
0.9295	High Similarity	NPC101636
0.9295	High Similarity	NPC47923
0.929	High Similarity	NPC43761
0.9286	High Similarity	NPC261866
0.9286	High Similarity	NPC473657
0.9286	High Similarity	NPC295613
0.9276	High Similarity	NPC278476
0.9276	High Similarity	NPC319910
0.9276	High Similarity	NPC262038
0.9276	High Similarity	NPC262039
0.9276	High Similarity	NPC254412
0.9267	High Similarity	NPC472918
0.9267	High Similarity	NPC218685
0.9262	High Similarity	NPC62290
0.9262	High Similarity	NPC4152
0.9262	High Similarity	NPC279417
0.9262	High Similarity	NPC326506
0.9262	High Similarity	NPC142731
0.9262	High Similarity	NPC306607
0.9262	High Similarity	NPC208176
0.9262	High Similarity	NPC49130
0.9245	High Similarity	NPC160156
0.9245	High Similarity	NPC92565
0.9245	High Similarity	NPC84362
0.9245	High Similarity	NPC317489
0.9245	High Similarity	NPC223424
0.9245	High Similarity	NPC173637
0.9245	High Similarity	NPC127546
0.9245	High Similarity	NPC52550
0.9241	High Similarity	NPC289667
0.9241	High Similarity	NPC292929
0.9241	High Similarity	NPC205824
0.9241	High Similarity	NPC277205
0.9241	High Similarity	NPC165720
0.9241	High Similarity	NPC85751
0.9241	High Similarity	NPC76831
0.9241	High Similarity	NPC129264
0.9241	High Similarity	NPC19240
0.9236	High Similarity	NPC475382
0.9236	High Similarity	NPC472876

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 NPC6985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	847
0.2-0.3	1711
0.3-0.4	2657
0.4-0.5	1954
0.5-0.6	1080
0.6-0.7	380
0.7-0.8	150
0.8-0.85	25
0.85-0.9	23
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9477	High Similarity	NPD4381	Clinical (unspecified phase)
0.9308	High Similarity	NPD7804	Clinical (unspecified phase)
0.9074	High Similarity	NPD6797	Phase 2
0.9018	High Similarity	NPD7251	Discontinued
0.9012	High Similarity	NPD7074	Phase 3
0.9006	High Similarity	NPD3818	Discontinued
0.8981	High Similarity	NPD7075	Discontinued
0.8963	High Similarity	NPD7808	Phase 3
0.8963	High Similarity	NPD4338	Clinical (unspecified phase)
0.8951	High Similarity	NPD7054	Approved
0.8896	High Similarity	NPD7472	Approved
0.8846	High Similarity	NPD6801	Discontinued
0.8839	High Similarity	NPD4380	Phase 2
0.8792	High Similarity	NPD1550	Clinical (unspecified phase)
0.8792	High Similarity	NPD1552	Clinical (unspecified phase)
0.879	High Similarity	NPD7096	Clinical (unspecified phase)
0.8765	High Similarity	NPD6166	Phase 2
0.8765	High Similarity	NPD6168	Clinical (unspecified phase)
0.8765	High Similarity	NPD6167	Clinical (unspecified phase)
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.8733	High Similarity	NPD1549	Phase 2
0.8726	High Similarity	NPD1934	Approved
0.8693	High Similarity	NPD6799	Approved
0.8675	High Similarity	NPD6559	Discontinued
0.8671	High Similarity	NPD2393	Clinical (unspecified phase)
0.8526	High Similarity	NPD5403	Approved
0.85	High Similarity	NPD3817	Phase 2
0.8481	Intermediate Similarity	NPD6599	Discontinued
0.8447	Intermediate Similarity	NPD3882	Suspended
0.8438	Intermediate Similarity	NPD2801	Approved
0.8428	Intermediate Similarity	NPD7411	Suspended
0.8397	Intermediate Similarity	NPD5401	Approved
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5402	Approved
0.8355	Intermediate Similarity	NPD2796	Approved
0.8344	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.828	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1240	Approved
0.8229	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1511	Approved
0.821	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1607	Approved
0.8025	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD3751	Discontinued
0.7988	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD3787	Discontinued
0.7964	Intermediate Similarity	NPD5494	Approved
0.7931	Intermediate Similarity	NPD8313	Approved
0.7931	Intermediate Similarity	NPD8312	Approved
0.7912	Intermediate Similarity	NPD6780	Approved
0.7912	Intermediate Similarity	NPD6777	Approved
0.7912	Intermediate Similarity	NPD6779	Approved
0.7912	Intermediate Similarity	NPD6776	Approved
0.7912	Intermediate Similarity	NPD6781	Approved
0.7912	Intermediate Similarity	NPD6778	Approved
0.7912	Intermediate Similarity	NPD6782	Approved
0.7911	Intermediate Similarity	NPD4628	Phase 3
0.7895	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6232	Discontinued
0.7849	Intermediate Similarity	NPD7584	Approved
0.7848	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD3749	Approved
0.7836	Intermediate Similarity	NPD7473	Discontinued
0.7799	Intermediate Similarity	NPD3750	Approved
0.7784	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD7435	Discontinued
0.7771	Intermediate Similarity	NPD8455	Phase 2
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7747	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5844	Phase 1
0.7736	Intermediate Similarity	NPD2800	Approved
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7688	Intermediate Similarity	NPD7697	Approved
0.7688	Intermediate Similarity	NPD7696	Phase 3
0.7688	Intermediate Similarity	NPD7698	Approved
0.7683	Intermediate Similarity	NPD1653	Approved
0.7673	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7662	Intermediate Similarity	NPD6798	Discontinued
0.7657	Intermediate Similarity	NPD5953	Discontinued
0.7651	Intermediate Similarity	NPD1091	Approved
0.7647	Intermediate Similarity	NPD7870	Phase 2
0.7647	Intermediate Similarity	NPD7871	Phase 2
0.7644	Intermediate Similarity	NPD7286	Phase 2
0.7637	Intermediate Similarity	NPD6534	Approved
0.7637	Intermediate Similarity	NPD6535	Approved
0.7628	Intermediate Similarity	NPD1933	Approved
0.7622	Intermediate Similarity	NPD920	Approved
0.7619	Intermediate Similarity	NPD7701	Phase 2
0.7616	Intermediate Similarity	NPD3926	Phase 2
0.7607	Intermediate Similarity	NPD2532	Approved
0.7607	Intermediate Similarity	NPD2534	Approved
0.7607	Intermediate Similarity	NPD2533	Approved
0.7605	Intermediate Similarity	NPD37	Approved
0.7595	Intermediate Similarity	NPD7033	Discontinued
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7586	Intermediate Similarity	NPD7228	Approved
0.758	Intermediate Similarity	NPD6651	Approved
0.7579	Intermediate Similarity	NPD8151	Discontinued
0.7574	Intermediate Similarity	NPD4966	Approved
0.7574	Intermediate Similarity	NPD4965	Approved
0.7574	Intermediate Similarity	NPD4967	Phase 2
0.7564	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1613	Approved
0.7547	Intermediate Similarity	NPD2935	Discontinued
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7874	Approved
0.7539	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6832	Phase 2
0.7514	Intermediate Similarity	NPD7699	Phase 2
0.7514	Intermediate Similarity	NPD7700	Phase 2
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7783	Phase 2
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7801	Approved
0.75	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD919	Approved
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD3748	Approved
0.7472	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD943	Approved
0.7451	Intermediate Similarity	NPD1203	Approved
0.7447	Intermediate Similarity	NPD6823	Phase 2
0.744	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7435	Intermediate Similarity	NPD7585	Approved
0.7425	Intermediate Similarity	NPD3226	Approved
0.7425	Intermediate Similarity	NPD7458	Discontinued
0.7423	Intermediate Similarity	NPD6190	Approved
0.7419	Intermediate Similarity	NPD4908	Phase 1
0.7418	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1652	Phase 2
0.7407	Intermediate Similarity	NPD1243	Approved
0.7405	Intermediate Similarity	NPD6355	Discontinued
0.7403	Intermediate Similarity	NPD2798	Approved
0.7382	Intermediate Similarity	NPD7583	Approved
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8320	Phase 1
0.7368	Intermediate Similarity	NPD8319	Approved
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.7329	Intermediate Similarity	NPD6099	Approved
0.7329	Intermediate Similarity	NPD6100	Approved
0.7325	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3268	Approved
0.7317	Intermediate Similarity	NPD2309	Approved
0.7308	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7303	Intermediate Similarity	NPD1610	Phase 2
0.7296	Intermediate Similarity	NPD5124	Phase 1
0.7296	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD230	Phase 1
0.7289	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2346	Discontinued
0.7284	Intermediate Similarity	NPD7266	Discontinued
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7261	Intermediate Similarity	NPD3027	Phase 3
0.7255	Intermediate Similarity	NPD9717	Approved
0.7244	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2424	Discontinued
0.7226	Intermediate Similarity	NPD2797	Approved
0.7222	Intermediate Similarity	NPD7240	Approved
0.7212	Intermediate Similarity	NPD2354	Approved
0.7212	Intermediate Similarity	NPD3887	Approved
0.7205	Intermediate Similarity	NPD7097	Phase 1
0.7204	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6212	Phase 3
0.7204	Intermediate Similarity	NPD6213	Phase 3
0.719	Intermediate Similarity	NPD422	Phase 1
0.7188	Intermediate Similarity	NPD447	Suspended
0.7186	Intermediate Similarity	NPD4661	Approved
0.7186	Intermediate Similarity	NPD4662	Approved
0.7175	Intermediate Similarity	NPD2403	Approved
0.717	Intermediate Similarity	NPD4062	Phase 3
0.7164	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5710	Approved
0.7159	Intermediate Similarity	NPD5711	Approved
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7390	Discontinued
0.7093	Intermediate Similarity	NPD6844	Discontinued
0.7091	Intermediate Similarity	NPD2654	Approved
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4308	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