NPASS Compound

Structure

NPC470183 OpenBabel07101719132D 37 39 0 0 1 0 0 0 0 0999 V2000 -7.4686 -2.1046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6933 -3.3294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6742 -4.6742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 -3.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0544 -3.5188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1566 -2.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4562 1.2090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0203 -3.7777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3473 -4.2259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 -3.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4495 -3.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6628 0.6002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 0.8263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 -2.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -1.9659 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7274 -3.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3813 -3.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4836 -3.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5106 -0.1652 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 0.8660 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 -1.7172 -0.7739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 -0.5478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8478 -1.7654 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 18 2 0 0 0 0 9 19 1 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 23 2 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 25 2 0 0 0 0 21 31 1 0 0 0 0 22 27 2 0 0 0 0 22 30 1 0 0 0 0 23 27 1 0 0 0 0 23 32 1 0 0 0 0 24 26 2 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 37 1 0 0 0 0 26 28 1 0 0 0 0 27 34 1 0 0 0 0 28 29 1 0 0 0 0 28 35 2 0 0 0 0 29 30 1 6 0 0 0 29 36 1 0 0 0 0 30 15 1 1 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.25
Volume:	536.934
LogP:	5.54
LogD:	3.831
LogS:	-2.991
# Rotatable Bonds:	9
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	4.255
Fsp3:	0.367
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.036
MDCK Permeability:	1.593582237546798e-05
Pgp-inhibitor:	0.37
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.745
30% Bioavailability (F30%):	0.084

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	97.77262115478516%
Volume Distribution (VD):	0.309
Pgp-substrate:	0.9012656211853027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.597
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.536
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.878
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.965
CYP2D6-substrate:	0.242
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	8.153
Half-life (T1/2):	0.431

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.614
Drug-inuced Liver Injury (DILI):	0.092
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.12
Skin Sensitization:	0.954
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.843
Respiratory Toxicity:	0.431

Download Data

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

Natural Product: NPC470183

Natural Product ID:	NPC470183
*Common Name:**	Notabilisin B
IUPAC Name:	(2S,3R)-2-(2,3-dihydroxyphenyl)-3,5,7-trihydroxy-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-3H-chromen-4-one
Synonyms:	Notabilisin B
Standard InCHIKey:	JAKJQYYMYOIRIK-RPGACVNKSA-N
Standard InCHI:	InChI=1S/C30H36O7/c1-18(2)8-5-9-19(3)10-6-11-20(4)14-15-30(22-12-7-13-23(32)27(22)34)29(36)28(35)26-24(33)16-21(31)17-25(26)37-30/h7-8,10,12-14,16-17,29,31-34,36H,5-6,9,11,15H2,1-4H3/b19-10+,20-14+/t29-,30-/m0/s1
SMILES:	C/C(=CC[C@]1(Oc2cc(O)cc(c2C(=O)[C@@H]1O)O)c1cccc(c1O)O)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1808153
PubChem CID:	56663045
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO27320	Morus notabilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21737271]
NPO27320	Morus notabilis	Species	Moraceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	147.96	%	PMID[477638]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	218.2	%	PMID[477638]

☑ 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 NPC470183 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	404
0.1-0.2	1478
0.2-0.3	3512
0.3-0.4	8806
0.4-0.5	9531
0.5-0.6	3654
0.6-0.7	4677
0.7-0.8	5751
0.8-0.85	2916
0.85-0.9	1616
0.9-0.95	319
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
0.9673	High Similarity	NPC22192
0.9671	High Similarity	NPC471500
0.9671	High Similarity	NPC13858
0.9671	High Similarity	NPC326037
0.9671	High Similarity	NPC320825
0.9613	High Similarity	NPC472964
0.9613	High Similarity	NPC211107
0.961	High Similarity	NPC282009
0.961	High Similarity	NPC287328
0.9608	High Similarity	NPC471479
0.9608	High Similarity	NPC67876
0.9608	High Similarity	NPC471515
0.9608	High Similarity	NPC52530
0.9603	High Similarity	NPC61506
0.9603	High Similarity	NPC36835
0.9603	High Similarity	NPC240476
0.9603	High Similarity	NPC246162
0.9603	High Similarity	NPC260491
0.9603	High Similarity	NPC9743
0.9554	High Similarity	NPC471213
0.9551	High Similarity	NPC472625
0.9548	High Similarity	NPC471499
0.9548	High Similarity	NPC472634
0.9548	High Similarity	NPC173137
0.9545	High Similarity	NPC55738
0.9542	High Similarity	NPC24640
0.9542	High Similarity	NPC250922
0.9539	High Similarity	NPC246328
0.9539	High Similarity	NPC325028
0.9539	High Similarity	NPC27532
0.9539	High Similarity	NPC256346
0.9539	High Similarity	NPC141212
0.9539	High Similarity	NPC18727
0.949	High Similarity	NPC224280
0.949	High Similarity	NPC62261
0.949	High Similarity	NPC475888
0.9484	High Similarity	NPC472630
0.9484	High Similarity	NPC470326
0.9484	High Similarity	NPC321399
0.9484	High Similarity	NPC472631
0.9484	High Similarity	NPC472902
0.9484	High Similarity	NPC263449
0.9481	High Similarity	NPC472598
0.9481	High Similarity	NPC27337
0.9481	High Similarity	NPC474055
0.9477	High Similarity	NPC321779
0.9477	High Similarity	NPC67396
0.9474	High Similarity	NPC219582
0.9474	High Similarity	NPC302950
0.9474	High Similarity	NPC236637
0.9474	High Similarity	NPC19721
0.9427	High Similarity	NPC474240
0.9423	High Similarity	NPC471210
0.9423	High Similarity	NPC308992
0.9423	High Similarity	NPC158188
0.9423	High Similarity	NPC289771
0.9423	High Similarity	NPC474038
0.9423	High Similarity	NPC472632
0.9423	High Similarity	NPC112418
0.9419	High Similarity	NPC210459
0.9419	High Similarity	NPC152904
0.9416	High Similarity	NPC209614
0.9416	High Similarity	NPC201837
0.9416	High Similarity	NPC195796
0.9416	High Similarity	NPC472626
0.9416	High Similarity	NPC474638
0.9416	High Similarity	NPC291878
0.9416	High Similarity	NPC470328
0.9416	High Similarity	NPC35038
0.9416	High Similarity	NPC278778
0.9412	High Similarity	NPC192083
0.9412	High Similarity	NPC74924
0.9412	High Similarity	NPC213896
0.9412	High Similarity	NPC298692
0.9367	High Similarity	NPC293319
0.9367	High Similarity	NPC36
0.9367	High Similarity	NPC7688
0.9367	High Similarity	NPC234052
0.9367	High Similarity	NPC7154
0.9367	High Similarity	NPC58223
0.9367	High Similarity	NPC72787
0.9367	High Similarity	NPC125039
0.9367	High Similarity	NPC36916
0.9363	High Similarity	NPC474033
0.9363	High Similarity	NPC201800
0.9363	High Similarity	NPC471745
0.9363	High Similarity	NPC474034
0.9363	High Similarity	NPC472635
0.9359	High Similarity	NPC174953
0.9359	High Similarity	NPC118256
0.9359	High Similarity	NPC475784
0.9359	High Similarity	NPC119209
0.9359	High Similarity	NPC471744
0.9359	High Similarity	NPC36217
0.9359	High Similarity	NPC192686
0.9359	High Similarity	NPC472624
0.9355	High Similarity	NPC475267
0.9355	High Similarity	NPC48208
0.9355	High Similarity	NPC474208
0.9355	High Similarity	NPC299520
0.9355	High Similarity	NPC291508
0.9355	High Similarity	NPC471209
0.9355	High Similarity	NPC474836
0.9355	High Similarity	NPC156057
0.9355	High Similarity	NPC129684
0.9355	High Similarity	NPC162869
0.9355	High Similarity	NPC472963
0.9351	High Similarity	NPC477503
0.9351	High Similarity	NPC226025
0.9351	High Similarity	NPC45849
0.9351	High Similarity	NPC470327
0.9351	High Similarity	NPC200761
0.9346	High Similarity	NPC260979
0.9346	High Similarity	NPC106976
0.9346	High Similarity	NPC138288
0.9346	High Similarity	NPC472912
0.9342	High Similarity	NPC338131
0.9338	High Similarity	NPC321011
0.9338	High Similarity	NPC294852
0.9338	High Similarity	NPC218569
0.9338	High Similarity	NPC188679
0.9308	High Similarity	NPC477517
0.9304	High Similarity	NPC124038
0.9304	High Similarity	NPC186686
0.9304	High Similarity	NPC41301
0.9299	High Similarity	NPC26326
0.9299	High Similarity	NPC142252
0.9299	High Similarity	NPC474239
0.9299	High Similarity	NPC471212
0.9299	High Similarity	NPC471211
0.9295	High Similarity	NPC53545
0.9295	High Similarity	NPC473990
0.9295	High Similarity	NPC329091
0.9295	High Similarity	NPC117418
0.929	High Similarity	NPC215917
0.929	High Similarity	NPC235165
0.929	High Similarity	NPC255106
0.929	High Similarity	NPC303255
0.929	High Similarity	NPC10754
0.929	High Similarity	NPC20530
0.929	High Similarity	NPC472907
0.9286	High Similarity	NPC293286
0.9286	High Similarity	NPC100134
0.9286	High Similarity	NPC78326
0.9286	High Similarity	NPC270620
0.9286	High Similarity	NPC209760
0.9286	High Similarity	NPC469550
0.9286	High Similarity	NPC179126
0.9286	High Similarity	NPC236223
0.9281	High Similarity	NPC252933
0.9281	High Similarity	NPC262039
0.9281	High Similarity	NPC254412
0.9281	High Similarity	NPC54394
0.9281	High Similarity	NPC200740
0.9281	High Similarity	NPC125062
0.9281	High Similarity	NPC471677
0.9281	High Similarity	NPC319910
0.9281	High Similarity	NPC278476
0.9281	High Similarity	NPC262038
0.9281	High Similarity	NPC471229
0.9276	High Similarity	NPC270465
0.9276	High Similarity	NPC1612
0.9276	High Similarity	NPC183959
0.9276	High Similarity	NPC87125
0.9276	High Similarity	NPC277032
0.9272	High Similarity	NPC122828
0.9272	High Similarity	NPC21835
0.9272	High Similarity	NPC211466
0.9272	High Similarity	NPC472918
0.9272	High Similarity	NPC44721
0.9272	High Similarity	NPC40086
0.9272	High Similarity	NPC3779
0.9272	High Similarity	NPC176869
0.9272	High Similarity	NPC476182
0.9255	High Similarity	NPC102277
0.9255	High Similarity	NPC279209
0.925	High Similarity	NPC158761
0.925	High Similarity	NPC218226
0.9241	High Similarity	NPC127782
0.9241	High Similarity	NPC300537
0.9241	High Similarity	NPC476247
0.9241	High Similarity	NPC474150
0.9241	High Similarity	NPC474162
0.9236	High Similarity	NPC328102
0.9236	High Similarity	NPC299436
0.9236	High Similarity	NPC474960
0.9231	High Similarity	NPC237418
0.9231	High Similarity	NPC222814
0.9231	High Similarity	NPC472910
0.9231	High Similarity	NPC470402
0.9231	High Similarity	NPC245758
0.9231	High Similarity	NPC469584
0.9231	High Similarity	NPC473272
0.9231	High Similarity	NPC472911
0.9231	High Similarity	NPC273843
0.9231	High Similarity	NPC210084
0.9231	High Similarity	NPC96167
0.9231	High Similarity	NPC284820
0.9231	High Similarity	NPC472914
0.9231	High Similarity	NPC99597

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 NPC470183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	891
0.2-0.3	1763
0.3-0.4	2564
0.4-0.5	1853
0.5-0.6	1006
0.6-0.7	508
0.7-0.8	153
0.8-0.85	30
0.85-0.9	17
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9474	High Similarity	NPD1934	Approved
0.9412	High Similarity	NPD2393	Clinical (unspecified phase)
0.9367	High Similarity	NPD6166	Phase 2
0.9367	High Similarity	NPD6168	Clinical (unspecified phase)
0.9367	High Similarity	NPD6167	Clinical (unspecified phase)
0.9079	High Similarity	NPD1512	Approved
0.9045	High Similarity	NPD3882	Suspended
0.9038	High Similarity	NPD2801	Approved
0.9024	High Similarity	NPD7251	Discontinued
0.9018	High Similarity	NPD7074	Phase 3
0.8963	High Similarity	NPD6797	Phase 2
0.8957	High Similarity	NPD7054	Approved
0.8947	High Similarity	NPD1511	Approved
0.8902	High Similarity	NPD7472	Approved
0.8868	High Similarity	NPD7075	Discontinued
0.8861	High Similarity	NPD3817	Phase 2
0.8855	High Similarity	NPD7808	Phase 3
0.8797	High Similarity	NPD7096	Clinical (unspecified phase)
0.878	High Similarity	NPD3818	Discontinued
0.8766	High Similarity	NPD4378	Clinical (unspecified phase)
0.8743	High Similarity	NPD4338	Clinical (unspecified phase)
0.8726	High Similarity	NPD4380	Phase 2
0.8688	High Similarity	NPD4868	Clinical (unspecified phase)
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8634	High Similarity	NPD4381	Clinical (unspecified phase)
0.8618	High Similarity	NPD1549	Phase 2
0.8614	High Similarity	NPD7804	Clinical (unspecified phase)
0.8528	High Similarity	NPD5494	Approved
0.8512	High Similarity	NPD7993	Clinical (unspecified phase)
0.8509	High Similarity	NPD8443	Clinical (unspecified phase)
0.85	High Similarity	NPD6801	Discontinued
0.8462	Intermediate Similarity	NPD6799	Approved
0.8447	Intermediate Similarity	NPD7819	Suspended
0.8375	Intermediate Similarity	NPD6599	Discontinued
0.8366	Intermediate Similarity	NPD2796	Approved
0.8301	Intermediate Similarity	NPD1510	Phase 2
0.8284	Intermediate Similarity	NPD5844	Phase 1
0.8282	Intermediate Similarity	NPD5402	Approved
0.8278	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD1613	Approved
0.8274	Intermediate Similarity	NPD7473	Discontinued
0.8253	Intermediate Similarity	NPD6959	Discontinued
0.8204	Intermediate Similarity	NPD6232	Discontinued
0.8187	Intermediate Similarity	NPD5403	Approved
0.8176	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1240	Approved
0.814	Intermediate Similarity	NPD6559	Discontinued
0.811	Intermediate Similarity	NPD1465	Phase 2
0.8098	Intermediate Similarity	NPD7411	Suspended
0.8063	Intermediate Similarity	NPD5401	Approved
0.8052	Intermediate Similarity	NPD1607	Approved
0.8047	Intermediate Similarity	NPD3926	Phase 2
0.8039	Intermediate Similarity	NPD943	Approved
0.8013	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3751	Discontinued
0.7988	Intermediate Similarity	NPD3787	Discontinued
0.7961	Intermediate Similarity	NPD3027	Phase 3
0.7947	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1247	Approved
0.7925	Intermediate Similarity	NPD4628	Phase 3
0.7917	Intermediate Similarity	NPD919	Approved
0.7911	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7768	Phase 2
0.7898	Intermediate Similarity	NPD6099	Approved
0.7898	Intermediate Similarity	NPD6100	Approved
0.7895	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6190	Approved
0.7857	Intermediate Similarity	NPD3749	Approved
0.7853	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD3750	Approved
0.7792	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD230	Phase 1
0.775	Intermediate Similarity	NPD2800	Approved
0.7733	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2534	Approved
0.773	Intermediate Similarity	NPD2532	Approved
0.773	Intermediate Similarity	NPD2533	Approved
0.7719	Intermediate Similarity	NPD7199	Phase 2
0.7709	Intermediate Similarity	NPD8434	Phase 2
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7673	Intermediate Similarity	NPD2935	Discontinued
0.764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7685	Pre-registration
0.7624	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8150	Discontinued
0.7602	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD7228	Approved
0.7593	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1653	Approved
0.7584	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4908	Phase 1
0.7542	Intermediate Similarity	NPD8313	Approved
0.7542	Intermediate Similarity	NPD8312	Approved
0.754	Intermediate Similarity	NPD6777	Approved
0.754	Intermediate Similarity	NPD6781	Approved
0.754	Intermediate Similarity	NPD6780	Approved
0.754	Intermediate Similarity	NPD6782	Approved
0.754	Intermediate Similarity	NPD6776	Approved
0.754	Intermediate Similarity	NPD6779	Approved
0.754	Intermediate Similarity	NPD6778	Approved
0.7532	Intermediate Similarity	NPD6355	Discontinued
0.7532	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD2344	Approved
0.7515	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD3748	Approved
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD4966	Approved
0.7484	Intermediate Similarity	NPD6651	Approved
0.7459	Intermediate Similarity	NPD4360	Phase 2
0.7459	Intermediate Similarity	NPD4363	Phase 3
0.7458	Intermediate Similarity	NPD7286	Phase 2
0.7455	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6798	Discontinued
0.744	Intermediate Similarity	NPD3226	Approved
0.7434	Intermediate Similarity	NPD1610	Phase 2
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD920	Approved
0.7421	Intermediate Similarity	NPD1933	Approved
0.7421	Intermediate Similarity	NPD7698	Approved
0.7421	Intermediate Similarity	NPD7696	Phase 3
0.7421	Intermediate Similarity	NPD7697	Approved
0.7407	Intermediate Similarity	NPD2346	Discontinued
0.7396	Intermediate Similarity	NPD7584	Approved
0.7391	Intermediate Similarity	NPD2799	Discontinued
0.7391	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2403	Approved
0.7382	Intermediate Similarity	NPD7870	Phase 2
0.7382	Intermediate Similarity	NPD7871	Phase 2
0.7374	Intermediate Similarity	NPD5953	Discontinued
0.7372	Intermediate Similarity	NPD9494	Approved
0.7358	Intermediate Similarity	NPD7701	Phase 2
0.7349	Intermediate Similarity	NPD7390	Discontinued
0.7342	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2309	Approved
0.7325	Intermediate Similarity	NPD6832	Phase 2
0.732	Intermediate Similarity	NPD8151	Discontinued
0.7317	Intermediate Similarity	NPD1243	Approved
0.731	Intermediate Similarity	NPD6844	Discontinued
0.7305	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7266	Discontinued
0.7296	Intermediate Similarity	NPD6233	Phase 2
0.7289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7874	Approved
0.7282	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4625	Phase 3
0.7278	Intermediate Similarity	NPD7095	Approved
0.7273	Intermediate Similarity	NPD5711	Approved
0.7273	Intermediate Similarity	NPD5710	Approved
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7261	Intermediate Similarity	NPD2861	Phase 2
0.7256	Intermediate Similarity	NPD2424	Discontinued
0.7251	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4060	Phase 1
0.7249	Intermediate Similarity	NPD7699	Phase 2
0.7249	Intermediate Similarity	NPD7700	Phase 2
0.7245	Intermediate Similarity	NPD7801	Approved
0.7245	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7783	Phase 2
0.7244	Intermediate Similarity	NPD1203	Approved
0.7235	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7232	Intermediate Similarity	NPD5242	Approved
0.7226	Intermediate Similarity	NPD4749	Approved
0.7225	Intermediate Similarity	NPD5353	Approved
0.7212	Intermediate Similarity	NPD1652	Phase 2
0.7205	Intermediate Similarity	NPD5124	Phase 1
0.7205	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2798	Approved
0.7191	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6823	Phase 2
0.7175	Intermediate Similarity	NPD7229	Phase 3
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.7168	Intermediate Similarity	NPD5761	Phase 2
0.7168	Intermediate Similarity	NPD5760	Phase 2
0.7161	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD2494	Approved
0.7135	Intermediate Similarity	NPD2493	Approved
0.7134	Intermediate Similarity	NPD2797	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