NPASS Compound

Structure

NPC94179 OpenBabel07101718242D 33 35 0 0 1 0 0 0 0 0999 V2000 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 2.5981 2.5000 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 4.3301 2.5000 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 6.0622 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 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 5.1962 4.0000 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 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 0.0000 1.0000 0.0000 C 0 0 1 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 6.0622 4.5000 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 4.3301 5.5000 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 0.0000 0.0000 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 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 14 1 0 0 0 0 5 8 1 0 0 0 0 5 15 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 32 1 0 0 0 0 16 4 1 1 0 0 0 16 33 1 0 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 23 1 0 0 0 0 22 30 1 6 0 0 0 23 24 1 0 0 0 0 23 31 1 1 0 0 0 24 32 1 0 0 0 0 24 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.2
Volume:	461.284
LogP:	2.01
LogD:	2.308
LogS:	-3.528
# Rotatable Bonds:	10
TPSA:	160.07
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.205
Synthetic Accessibility Score:	3.961
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.981
MDCK Permeability:	9.420901733392384e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.639
Human Intestinal Absorption (HIA):	0.949
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	97.06501007080078%
Volume Distribution (VD):	0.364
Pgp-substrate:	3.1935830116271973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.107
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.109
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.378
CYP2C9-substrate:	0.513
CYP2D6-inhibitor:	0.648
CYP2D6-substrate:	0.376
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	8.406
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.774
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.736
Skin Sensitization:	0.971
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.866
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC94179

Natural Product ID:	NPC94179
*Common Name:**	(3R)-1,7-Bis-(3,4-Dihydroxyphenyl)-3-Heptanol-3-O-Beta-D-Xylopyranoside
IUPAC Name:	(2S,3R,4S,5R)-2-[(3R)-1,7-bis(3,4-dihydroxyphenyl)heptan-3-yl]oxyoxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	PVCSOVFCVIEUFH-IGCYBFCNSA-N
Standard InCHI:	InChI=1S/C24H32O9/c25-17-9-6-14(11-19(17)27)3-1-2-4-16(8-5-15-7-10-18(26)20(28)12-15)33-24-23(31)22(30)21(29)13-32-24/h6-7,9-12,16,21-31H,1-5,8,13H2/t16-,21-,22+,23-,24+/m1/s1
SMILES:	O[C@@H]1CO[C@H]([C@@H]([C@H]1O)O)O[C@@H](CCc1ccc(c(c1)O)O)CCCCc1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774775
PubChem CID:	24011643
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO4971	Alnus firma	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504848]
NPO32876	alnus hirsuta f. sibirica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23465614]
NPO4971	Alnus firma	Species	Betulaceae	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
Others	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	97.0	%	PMID[520646]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	110.8	%	PMID[520646]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	93.2	%	PMID[520646]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	22.7	%	PMID[520645]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[520645]

☑ 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 NPC94179 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	355
0.1-0.2	1361
0.2-0.3	3466
0.3-0.4	9936
0.4-0.5	9527
0.5-0.6	7283
0.6-0.7	7540
0.7-0.8	2771
0.8-0.85	330
0.85-0.9	103
0.9-0.95	19
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC79715
0.9917	High Similarity	NPC264900
0.9917	High Similarity	NPC108659
0.9917	High Similarity	NPC231607
0.9754	High Similarity	NPC184092
0.952	High Similarity	NPC254275
0.9512	High Similarity	NPC148982
0.9417	High Similarity	NPC266045
0.9333	High Similarity	NPC469703
0.9333	High Similarity	NPC160854
0.9333	High Similarity	NPC469704
0.9333	High Similarity	NPC201402
0.9268	High Similarity	NPC90318
0.9256	High Similarity	NPC469686
0.9225	High Similarity	NPC177035
0.9225	High Similarity	NPC52277
0.9225	High Similarity	NPC199459
0.918	High Similarity	NPC471067
0.9147	High Similarity	NPC180171
0.9147	High Similarity	NPC158325
0.9147	High Similarity	NPC103398
0.9106	High Similarity	NPC178449
0.9106	High Similarity	NPC470907
0.9106	High Similarity	NPC232454
0.907	High Similarity	NPC287597
0.907	High Similarity	NPC34293
0.907	High Similarity	NPC886
0.9015	High Similarity	NPC106944
0.9008	High Similarity	NPC470413
0.9008	High Similarity	NPC138738
0.9008	High Similarity	NPC260425
0.9	High Similarity	NPC123988
0.8947	High Similarity	NPC472711
0.8939	High Similarity	NPC476383
0.8939	High Similarity	NPC81515
0.8939	High Similarity	NPC321184
0.8939	High Similarity	NPC197316
0.8939	High Similarity	NPC321638
0.8939	High Similarity	NPC89105
0.8939	High Similarity	NPC472350
0.8939	High Similarity	NPC328273
0.8939	High Similarity	NPC68092
0.8939	High Similarity	NPC205195
0.8939	High Similarity	NPC171134
0.8939	High Similarity	NPC64141
0.8923	High Similarity	NPC35731
0.8923	High Similarity	NPC476411
0.8864	High Similarity	NPC302583
0.8864	High Similarity	NPC310252
0.8864	High Similarity	NPC100558
0.8864	High Similarity	NPC78363
0.8864	High Similarity	NPC84789
0.8864	High Similarity	NPC304152
0.8837	High Similarity	NPC248307
0.8837	High Similarity	NPC476407
0.8837	High Similarity	NPC65942
0.8819	High Similarity	NPC469687
0.8815	High Similarity	NPC113680
0.8815	High Similarity	NPC185307
0.8815	High Similarity	NPC477898
0.8815	High Similarity	NPC470950
0.8815	High Similarity	NPC278961
0.8815	High Similarity	NPC46092
0.8806	High Similarity	NPC469661
0.8806	High Similarity	NPC476377
0.8806	High Similarity	NPC47471
0.8806	High Similarity	NPC134405
0.8806	High Similarity	NPC476385
0.879	High Similarity	NPC55608
0.878	High Similarity	NPC469702
0.878	High Similarity	NPC282409
0.8779	High Similarity	NPC187194
0.876	High Similarity	NPC148055
0.875	High Similarity	NPC129417
0.875	High Similarity	NPC253015
0.875	High Similarity	NPC283995
0.875	High Similarity	NPC471065
0.875	High Similarity	NPC157338
0.875	High Similarity	NPC84181
0.875	High Similarity	NPC470235
0.8741	High Similarity	NPC265648
0.8741	High Similarity	NPC189115
0.8741	High Similarity	NPC48309
0.8741	High Similarity	NPC472714
0.8741	High Similarity	NPC476356
0.8741	High Similarity	NPC469559
0.8741	High Similarity	NPC5262
0.8741	High Similarity	NPC222433
0.8731	High Similarity	NPC473799
0.8731	High Similarity	NPC475530
0.8712	High Similarity	NPC476870
0.871	High Similarity	NPC476448
0.871	High Similarity	NPC476445
0.871	High Similarity	NPC469548
0.8686	High Similarity	NPC22150
0.8686	High Similarity	NPC286245
0.8686	High Similarity	NPC38041
0.8686	High Similarity	NPC279298
0.8686	High Similarity	NPC475096
0.8686	High Similarity	NPC272619
0.8686	High Similarity	NPC18979
0.8682	High Similarity	NPC477294
0.8682	High Similarity	NPC307110
0.8682	High Similarity	NPC477293
0.8682	High Similarity	NPC229784
0.8676	High Similarity	NPC476380
0.8676	High Similarity	NPC264632
0.8676	High Similarity	NPC476378
0.8676	High Similarity	NPC298257
0.8676	High Similarity	NPC205864
0.8676	High Similarity	NPC40305
0.8676	High Similarity	NPC175214
0.8676	High Similarity	NPC247032
0.8676	High Similarity	NPC96795
0.8676	High Similarity	NPC476397
0.8676	High Similarity	NPC105005
0.8676	High Similarity	NPC76406
0.8676	High Similarity	NPC476381
0.8676	High Similarity	NPC112
0.8676	High Similarity	NPC119537
0.8676	High Similarity	NPC476384
0.8676	High Similarity	NPC269141
0.8676	High Similarity	NPC473044
0.8676	High Similarity	NPC476375
0.8657	High Similarity	NPC156376
0.8655	High Similarity	NPC187583
0.8655	High Similarity	NPC257430
0.8655	High Similarity	NPC179002
0.8647	High Similarity	NPC203230
0.8647	High Similarity	NPC242028
0.8636	High Similarity	NPC470881
0.8626	High Similarity	NPC473285
0.8623	High Similarity	NPC112861
0.8615	High Similarity	NPC17968
0.8615	High Similarity	NPC469705
0.8615	High Similarity	NPC470122
0.8613	High Similarity	NPC64195
0.8613	High Similarity	NPC472713
0.8613	High Similarity	NPC472712
0.8613	High Similarity	NPC168579
0.8613	High Similarity	NPC469313
0.8613	High Similarity	NPC118385
0.8613	High Similarity	NPC473045
0.8613	High Similarity	NPC473046
0.8613	High Similarity	NPC187774
0.8613	High Similarity	NPC25292
0.8613	High Similarity	NPC300894
0.8613	High Similarity	NPC141455
0.8613	High Similarity	NPC296954
0.8613	High Similarity	NPC196063
0.8613	High Similarity	NPC76176
0.8613	High Similarity	NPC138227
0.8605	High Similarity	NPC245826
0.8605	High Similarity	NPC232880
0.8605	High Similarity	NPC158673
0.8605	High Similarity	NPC474178
0.8605	High Similarity	NPC252307
0.8603	High Similarity	NPC140502
0.8582	High Similarity	NPC65530
0.8582	High Similarity	NPC59324
0.8582	High Similarity	NPC476376
0.8571	High Similarity	NPC226401
0.8571	High Similarity	NPC174096
0.8571	High Similarity	NPC79793
0.8571	High Similarity	NPC147634
0.8571	High Similarity	NPC120982
0.8571	High Similarity	NPC184938
0.8571	High Similarity	NPC101624
0.8561	High Similarity	NPC6836
0.8561	High Similarity	NPC224674
0.8561	High Similarity	NPC275284
0.8561	High Similarity	NPC39657
0.8561	High Similarity	NPC114505
0.8561	High Similarity	NPC227902
0.8561	High Similarity	NPC193473
0.8561	High Similarity	NPC213074
0.8561	High Similarity	NPC31325
0.8561	High Similarity	NPC15956
0.8551	High Similarity	NPC34927
0.8551	High Similarity	NPC34587
0.8551	High Similarity	NPC476382
0.8551	High Similarity	NPC252292
0.8551	High Similarity	NPC469586
0.8551	High Similarity	NPC100998
0.855	High Similarity	NPC219677
0.855	High Similarity	NPC9912
0.8548	High Similarity	NPC109371
0.8548	High Similarity	NPC477803
0.8548	High Similarity	NPC70084
0.8548	High Similarity	NPC470214
0.8548	High Similarity	NPC470215
0.854	High Similarity	NPC37793
0.8529	High Similarity	NPC186406
0.8529	High Similarity	NPC471908
0.8527	High Similarity	NPC288416
0.8527	High Similarity	NPC476873
0.8519	High Similarity	NPC98777
0.8519	High Similarity	NPC212770
0.8504	High Similarity	NPC473451
0.85	High Similarity	NPC280945

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 NPC94179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	774
0.2-0.3	1618
0.3-0.4	3005
0.4-0.5	1875
0.5-0.6	1099
0.6-0.7	439
0.7-0.8	48
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8939	High Similarity	NPD7266	Discontinued
0.812	Intermediate Similarity	NPD3027	Phase 3
0.8074	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD1613	Approved
0.8033	Intermediate Similarity	NPD3022	Approved
0.8033	Intermediate Similarity	NPD3021	Approved
0.7778	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6674	Discontinued
0.7704	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1653	Approved
0.7652	Intermediate Similarity	NPD1091	Approved
0.7639	Intermediate Similarity	NPD6190	Approved
0.7484	Intermediate Similarity	NPD7074	Phase 3
0.7483	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7228	Approved
0.7426	Intermediate Similarity	NPD3094	Phase 2
0.7424	Intermediate Similarity	NPD1357	Approved
0.7421	Intermediate Similarity	NPD7054	Approved
0.7388	Intermediate Similarity	NPD3705	Approved
0.7375	Intermediate Similarity	NPD7472	Approved
0.7368	Intermediate Similarity	NPD5125	Phase 3
0.7368	Intermediate Similarity	NPD5126	Approved
0.7358	Intermediate Similarity	NPD3818	Discontinued
0.7355	Intermediate Similarity	NPD6234	Discontinued
0.7344	Intermediate Similarity	NPD228	Approved
0.7333	Intermediate Similarity	NPD2859	Approved
0.7333	Intermediate Similarity	NPD2860	Approved
0.7324	Intermediate Similarity	NPD5314	Approved
0.7319	Intermediate Similarity	NPD2861	Phase 2
0.7305	Intermediate Similarity	NPD3059	Approved
0.7305	Intermediate Similarity	NPD3062	Approved
0.7305	Intermediate Similarity	NPD3061	Approved
0.7295	Intermediate Similarity	NPD3020	Approved
0.7284	Intermediate Similarity	NPD7251	Discontinued
0.7259	Intermediate Similarity	NPD3092	Approved
0.7255	Intermediate Similarity	NPD37	Approved
0.725	Intermediate Similarity	NPD2934	Approved
0.725	Intermediate Similarity	NPD2933	Approved
0.7239	Intermediate Similarity	NPD9381	Approved
0.7239	Intermediate Similarity	NPD9384	Approved
0.7231	Intermediate Similarity	NPD5283	Phase 1
0.723	Intermediate Similarity	NPD5058	Phase 3
0.7226	Intermediate Similarity	NPD4965	Approved
0.7226	Intermediate Similarity	NPD4966	Approved
0.7226	Intermediate Similarity	NPD4967	Phase 2
0.7222	Intermediate Similarity	NPD6797	Phase 2
0.7208	Intermediate Similarity	NPD8455	Phase 2
0.7183	Intermediate Similarity	NPD3620	Phase 2
0.7183	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7685	Pre-registration
0.7154	Intermediate Similarity	NPD7843	Approved
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7808	Phase 3
0.7121	Intermediate Similarity	NPD7157	Approved
0.7115	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1242	Phase 1
0.7097	Intermediate Similarity	NPD2977	Approved
0.7097	Intermediate Similarity	NPD2978	Approved
0.709	Intermediate Similarity	NPD3091	Approved
0.7034	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4538	Approved
0.7034	Intermediate Similarity	NPD4536	Approved
0.7032	Intermediate Similarity	NPD1934	Approved
0.7029	Intermediate Similarity	NPD9622	Approved
0.7027	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4908	Phase 1
0.702	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1610	Phase 2
0.7	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4108	Discontinued
0.6986	Remote Similarity	NPD5960	Phase 3
0.6986	Remote Similarity	NPD5588	Approved
0.6985	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8166	Discontinued
0.6978	Remote Similarity	NPD5311	Approved
0.6978	Remote Similarity	NPD5310	Approved
0.6977	Remote Similarity	NPD2684	Approved
0.697	Remote Similarity	NPD7240	Approved
0.6966	Remote Similarity	NPD823	Approved
0.6966	Remote Similarity	NPD817	Approved
0.695	Remote Similarity	NPD5736	Approved
0.6944	Remote Similarity	NPD4060	Phase 1
0.6937	Remote Similarity	NPD7199	Phase 2
0.6923	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7097	Phase 1
0.6914	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6166	Phase 2
0.6914	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2982	Phase 2
0.6906	Remote Similarity	NPD2983	Phase 2
0.6905	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD9377	Approved
0.6894	Remote Similarity	NPD9379	Approved
0.689	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9621	Approved
0.6879	Remote Similarity	NPD9620	Approved
0.6879	Remote Similarity	NPD9619	Approved
0.6875	Remote Similarity	NPD6407	Approved
0.6875	Remote Similarity	NPD6405	Approved
0.6867	Remote Similarity	NPD6559	Discontinued
0.6866	Remote Similarity	NPD6671	Approved
0.6861	Remote Similarity	NPD6516	Phase 2
0.6861	Remote Similarity	NPD3095	Discontinued
0.6861	Remote Similarity	NPD5846	Approved
0.6855	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7095	Approved
0.6838	Remote Similarity	NPD1548	Phase 1
0.6835	Remote Similarity	NPD2981	Phase 2
0.6831	Remote Similarity	NPD3018	Phase 2
0.6829	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1558	Phase 1
0.6828	Remote Similarity	NPD825	Approved
0.6828	Remote Similarity	NPD826	Approved
0.6815	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3053	Approved
0.6809	Remote Similarity	NPD3055	Approved
0.6806	Remote Similarity	NPD601	Approved
0.6806	Remote Similarity	NPD598	Approved
0.6806	Remote Similarity	NPD597	Approved
0.68	Remote Similarity	NPD5177	Phase 3
0.68	Remote Similarity	NPD3060	Approved
0.6795	Remote Similarity	NPD4380	Phase 2
0.6786	Remote Similarity	NPD4659	Approved
0.6781	Remote Similarity	NPD230	Phase 1
0.6781	Remote Similarity	NPD5735	Approved
0.6776	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD844	Approved
0.6772	Remote Similarity	NPD940	Approved
0.6772	Remote Similarity	NPD846	Approved
0.6767	Remote Similarity	NPD7635	Approved
0.6761	Remote Similarity	NPD6584	Phase 3
0.6759	Remote Similarity	NPD1136	Approved
0.6759	Remote Similarity	NPD6663	Approved
0.6759	Remote Similarity	NPD1132	Approved
0.6759	Remote Similarity	NPD1130	Approved
0.6759	Remote Similarity	NPD6233	Phase 2
0.6748	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD8651	Approved
0.6716	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD943	Approved
0.6711	Remote Similarity	NPD9570	Approved
0.671	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD3028	Approved
0.6692	Remote Similarity	NPD968	Approved
0.669	Remote Similarity	NPD6798	Discontinued
0.669	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4103	Phase 2
0.669	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4236	Phase 3
0.6689	Remote Similarity	NPD4237	Approved
0.6686	Remote Similarity	NPD8312	Approved
0.6686	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD1375	Discontinued
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4750	Phase 3
0.6645	Remote Similarity	NPD4535	Phase 3
0.6645	Remote Similarity	NPD4628	Phase 3
0.6642	Remote Similarity	NPD5536	Phase 2
0.6641	Remote Similarity	NPD290	Approved
0.6641	Remote Similarity	NPD2342	Discontinued
0.6624	Remote Similarity	NPD3455	Phase 2
0.6623	Remote Similarity	NPD1511	Approved
0.6622	Remote Similarity	NPD2568	Approved
0.6622	Remote Similarity	NPD6653	Approved
0.6621	Remote Similarity	NPD4625	Phase 3
0.6611	Remote Similarity	NPD7680	Approved
0.6596	Remote Similarity	NPD2231	Phase 2
0.6596	Remote Similarity	NPD2235	Phase 2
0.6596	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.659	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD288	Approved
0.6585	Remote Similarity	NPD3787	Discontinued
0.6581	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4162	Approved
0.6573	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD969	Suspended
0.6556	Remote Similarity	NPD5763	Approved
0.6556	Remote Similarity	NPD5762	Approved
0.6554	Remote Similarity	NPD4340	Discontinued
0.6554	Remote Similarity	NPD555	Phase 2
0.6552	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6582	Phase 2
0.6549	Remote Similarity	NPD6583	Phase 3
0.6549	Remote Similarity	NPD4749	Approved
0.6549	Remote Similarity	NPD3685	Discontinued

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