NPASS Compound

Structure

NPC184092 OpenBabel07101719142D 44 47 0 0 1 0 0 0 0 0999 V2000 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 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 4.3301 4.5000 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 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 -3.4641 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 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 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 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 -0.0000 3.0000 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 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 -2.5981 -1.5000 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 -0.8660 3.5000 0.0000 O 0 0 0 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 0.8660 4.5000 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 15 1 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 31 1 0 0 0 0 14 22 1 0 0 0 0 14 41 1 0 0 0 0 17 4 1 1 0 0 0 17 42 1 0 0 0 0 18 20 2 0 0 0 0 18 32 1 0 0 0 0 19 21 2 0 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 21 35 1 0 0 0 0 22 28 1 0 0 0 0 22 36 1 1 0 0 0 23 13 1 6 0 0 0 23 24 1 0 0 0 0 23 43 1 0 0 0 0 24 25 1 0 0 0 0 24 37 1 1 0 0 0 25 26 1 0 0 0 0 25 38 1 6 0 0 0 26 30 1 0 0 0 0 26 39 1 1 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 27 40 1 1 0 0 0 28 44 1 6 0 0 0 29 41 1 0 0 0 0 29 42 1 6 0 0 0 30 43 1 0 0 0 0 30 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	626.26
Volume:	600.455
LogP:	0.063
LogD:	0.354
LogS:	-2.908
# Rotatable Bonds:	13
TPSA:	239.22
# H-Bond Aceptor:	14
# H-Bond Donor:	10
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.1
Synthetic Accessibility Score:	4.757
Fsp3:	0.6
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.362
MDCK Permeability:	7.726619514869526e-06
Pgp-inhibitor:	0.022
Pgp-substrate:	0.906
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	95.13601684570312%
Volume Distribution (VD):	0.163
Pgp-substrate:	4.811973571777344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.194
CYP2D6-inhibitor:	0.144
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	1.341
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.317
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.342
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.969
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.19
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC184092

Natural Product ID:	NPC184092
*Common Name:**	(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R)-2-[(3R)-1,7-Bis(3,4-Dihydroxyphenyl)Heptan-3-Yl]Oxy-3,5-Dihydroxyoxan-4-Yl]Oxy-6-(Hydroxymethyl)Oxane-3,4,5-Triol
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R)-2-[(3R)-1,7-bis(3,4-dihydroxyphenyl)heptan-3-yl]oxy-3,5-dihydroxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	XQPKKOQWBSSHEF-JKJJEPENSA-N
Standard InCHI:	InChI=1S/C30H42O14/c31-13-23-24(37)25(38)26(39)30(43-23)44-28-22(36)14-41-29(27(28)40)42-17(8-5-16-7-10-19(33)21(35)12-16)4-2-1-3-15-6-9-18(32)20(34)11-15/h6-7,9-12,17,22-40H,1-5,8,13-14H2/t17-,22-,23-,24-,25+,26-,27-,28+,29+,30+/m1/s1
SMILES:	C(CC[C@H](CCc1ccc(c(c1)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)Cc1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774774
PubChem CID:	54585388
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]
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	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	22.7	%	PMID[506500]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	54900.0	nM	PMID[506500]

☑ 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 NPC184092 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	394
0.1-0.2	1410
0.2-0.3	3500
0.3-0.4	9342
0.4-0.5	9607
0.5-0.6	8595
0.6-0.7	7067
0.7-0.8	2406
0.8-0.85	262
0.85-0.9	86
0.9-0.95	26
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9836	High Similarity	NPC108659
0.9836	High Similarity	NPC231607
0.9836	High Similarity	NPC264900
0.9836	High Similarity	NPC79715
0.976	High Similarity	NPC254275
0.9754	High Similarity	NPC94179
0.944	High Similarity	NPC148982
0.9344	High Similarity	NPC266045
0.9262	High Similarity	NPC469704
0.9262	High Similarity	NPC469703
0.9262	High Similarity	NPC201402
0.9262	High Similarity	NPC160854
0.9242	High Similarity	NPC106944
0.9237	High Similarity	NPC260425
0.92	High Similarity	NPC90318
0.9187	High Similarity	NPC469686
0.9167	High Similarity	NPC64141
0.9167	High Similarity	NPC89105
0.9167	High Similarity	NPC472350
0.9167	High Similarity	NPC81515
0.9167	High Similarity	NPC205195
0.9167	High Similarity	NPC476383
0.9167	High Similarity	NPC68092
0.9167	High Similarity	NPC197316
0.916	High Similarity	NPC52277
0.916	High Similarity	NPC199459
0.916	High Similarity	NPC177035
0.9113	High Similarity	NPC471067
0.9091	High Similarity	NPC78363
0.904	High Similarity	NPC470907
0.904	High Similarity	NPC178449
0.904	High Similarity	NPC232454
0.9037	High Similarity	NPC278961
0.9037	High Similarity	NPC113680
0.9032	High Similarity	NPC55608
0.903	High Similarity	NPC47471
0.903	High Similarity	NPC476385
0.903	High Similarity	NPC134405
0.903	High Similarity	NPC476377
0.9008	High Similarity	NPC287597
0.9008	High Similarity	NPC886
0.9008	High Similarity	NPC35731
0.9008	High Similarity	NPC34293
0.8963	High Similarity	NPC222433
0.8963	High Similarity	NPC265648
0.8955	High Similarity	NPC475530
0.8955	High Similarity	NPC473799
0.8947	High Similarity	NPC138738
0.8947	High Similarity	NPC304152
0.8947	High Similarity	NPC470413
0.8939	High Similarity	NPC180171
0.8939	High Similarity	NPC158325
0.8939	High Similarity	NPC103398
0.8939	High Similarity	NPC123988
0.8897	High Similarity	NPC264632
0.8897	High Similarity	NPC298257
0.8897	High Similarity	NPC476384
0.8897	High Similarity	NPC76406
0.8897	High Similarity	NPC476375
0.8897	High Similarity	NPC96795
0.8897	High Similarity	NPC476378
0.8897	High Similarity	NPC105005
0.8897	High Similarity	NPC175214
0.8897	High Similarity	NPC205864
0.8897	High Similarity	NPC119537
0.8897	High Similarity	NPC112
0.8897	High Similarity	NPC476380
0.8897	High Similarity	NPC476381
0.8897	High Similarity	NPC269141
0.8897	High Similarity	NPC247032
0.8897	High Similarity	NPC476397
0.8889	High Similarity	NPC472711
0.8881	High Similarity	NPC321638
0.8881	High Similarity	NPC321184
0.8881	High Similarity	NPC328273
0.8881	High Similarity	NPC171134
0.8864	High Similarity	NPC476411
0.8832	High Similarity	NPC300894
0.8832	High Similarity	NPC296954
0.8832	High Similarity	NPC141455
0.8832	High Similarity	NPC138227
0.8832	High Similarity	NPC469313
0.8832	High Similarity	NPC64195
0.8832	High Similarity	NPC76176
0.8832	High Similarity	NPC196063
0.8832	High Similarity	NPC168579
0.8806	High Similarity	NPC84789
0.8806	High Similarity	NPC302583
0.8806	High Similarity	NPC310252
0.8806	High Similarity	NPC476376
0.8806	High Similarity	NPC100558
0.8797	High Similarity	NPC476870
0.8779	High Similarity	NPC248307
0.8779	High Similarity	NPC65942
0.8768	High Similarity	NPC286245
0.8768	High Similarity	NPC252292
0.8768	High Similarity	NPC34587
0.8768	High Similarity	NPC100998
0.8768	High Similarity	NPC34927
0.8768	High Similarity	NPC476382
0.8768	High Similarity	NPC272619
0.876	High Similarity	NPC469687
0.8759	High Similarity	NPC46092
0.8759	High Similarity	NPC185307
0.8759	High Similarity	NPC37793
0.8759	High Similarity	NPC470950
0.8759	High Similarity	NPC477898
0.875	High Similarity	NPC469661
0.8722	High Similarity	NPC187194
0.872	High Similarity	NPC469702
0.872	High Similarity	NPC282409
0.8714	High Similarity	NPC280945
0.8714	High Similarity	NPC116229
0.8712	High Similarity	NPC473285
0.8705	High Similarity	NPC125755
0.8705	High Similarity	NPC229505
0.8699	High Similarity	NPC148055
0.8696	High Similarity	NPC283995
0.8696	High Similarity	NPC253015
0.8696	High Similarity	NPC129417
0.8696	High Similarity	NPC471065
0.8696	High Similarity	NPC84181
0.8696	High Similarity	NPC470235
0.8689	High Similarity	NPC157338
0.8686	High Similarity	NPC472714
0.8686	High Similarity	NPC469559
0.8686	High Similarity	NPC476356
0.8686	High Similarity	NPC48309
0.8686	High Similarity	NPC5262
0.8686	High Similarity	NPC189115
0.8651	High Similarity	NPC469548
0.8651	High Similarity	NPC476448
0.8651	High Similarity	NPC476445
0.8643	High Similarity	NPC473480
0.8643	High Similarity	NPC232992
0.8643	High Similarity	NPC15538
0.8636	High Similarity	NPC9912
0.8636	High Similarity	NPC476407
0.8636	High Similarity	NPC235294
0.8636	High Similarity	NPC46137
0.8633	High Similarity	NPC279298
0.8633	High Similarity	NPC277867
0.8633	High Similarity	NPC161700
0.8633	High Similarity	NPC475096
0.8633	High Similarity	NPC22150
0.8633	High Similarity	NPC18979
0.8633	High Similarity	NPC38041
0.8626	High Similarity	NPC477294
0.8626	High Similarity	NPC307110
0.8626	High Similarity	NPC229784
0.8626	High Similarity	NPC477293
0.8623	High Similarity	NPC40305
0.8623	High Similarity	NPC473044
0.8603	High Similarity	NPC156376
0.8593	High Similarity	NPC203230
0.8593	High Similarity	NPC242028
0.8592	High Similarity	NPC475224
0.8582	High Similarity	NPC470881
0.8571	High Similarity	NPC112861
0.8561	High Similarity	NPC17968
0.8561	High Similarity	NPC473046
0.8561	High Similarity	NPC187774
0.8561	High Similarity	NPC476867
0.8561	High Similarity	NPC472713
0.8561	High Similarity	NPC473045
0.8561	High Similarity	NPC472712
0.8561	High Similarity	NPC471063
0.8561	High Similarity	NPC469705
0.8561	High Similarity	NPC470122
0.8561	High Similarity	NPC118385
0.8561	High Similarity	NPC25292
0.8551	High Similarity	NPC140502
0.855	High Similarity	NPC252307
0.855	High Similarity	NPC474178
0.855	High Similarity	NPC245826
0.855	High Similarity	NPC232880
0.8531	High Similarity	NPC473621
0.8529	High Similarity	NPC65530
0.8529	High Similarity	NPC59324
0.8521	High Similarity	NPC471062
0.8521	High Similarity	NPC476386
0.8521	High Similarity	NPC44452
0.8521	High Similarity	NPC473427
0.8521	High Similarity	NPC259347
0.8521	High Similarity	NPC94871
0.8521	High Similarity	NPC306890
0.8521	High Similarity	NPC476398
0.8521	High Similarity	NPC470933
0.8519	High Similarity	NPC184938
0.8519	High Similarity	NPC101624
0.8511	High Similarity	NPC275284
0.8511	High Similarity	NPC193473
0.8511	High Similarity	NPC213074
0.8511	High Similarity	NPC31325
0.8511	High Similarity	NPC227902
0.8511	High Similarity	NPC15956
0.8511	High Similarity	NPC114505
0.8511	High Similarity	NPC224674
0.8511	High Similarity	NPC39657
0.8507	High Similarity	NPC6836

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 NPC184092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	772
0.2-0.3	1646
0.3-0.4	3141
0.4-0.5	1850
0.5-0.6	1068
0.6-0.7	323
0.7-0.8	25
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD7266	Discontinued
0.8074	Intermediate Similarity	NPD3027	Phase 3
0.8029	Intermediate Similarity	NPD1613	Approved
0.8029	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3021	Approved
0.784	Intermediate Similarity	NPD3022	Approved
0.7737	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6674	Discontinued
0.7673	Intermediate Similarity	NPD7074	Phase 3
0.7664	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7228	Approved
0.7651	Intermediate Similarity	NPD1653	Approved
0.7612	Intermediate Similarity	NPD1091	Approved
0.761	Intermediate Similarity	NPD7054	Approved
0.7603	Intermediate Similarity	NPD6190	Approved
0.7562	Intermediate Similarity	NPD7472	Approved
0.7469	Intermediate Similarity	NPD7251	Discontinued
0.7448	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6797	Phase 2
0.7403	Intermediate Similarity	NPD8455	Phase 2
0.7353	Intermediate Similarity	NPD3705	Approved
0.7333	Intermediate Similarity	NPD5125	Phase 3
0.7333	Intermediate Similarity	NPD5126	Approved
0.7329	Intermediate Similarity	NPD3818	Discontinued
0.7325	Intermediate Similarity	NPD6234	Discontinued
0.7317	Intermediate Similarity	NPD7808	Phase 3
0.7292	Intermediate Similarity	NPD5314	Approved
0.7286	Intermediate Similarity	NPD2861	Phase 2
0.7273	Intermediate Similarity	NPD3061	Approved
0.7273	Intermediate Similarity	NPD3062	Approved
0.7273	Intermediate Similarity	NPD3059	Approved
0.7266	Intermediate Similarity	NPD3094	Phase 2
0.7261	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1357	Approved
0.7256	Intermediate Similarity	NPD7685	Pre-registration
0.7226	Intermediate Similarity	NPD37	Approved
0.7212	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD9381	Approved
0.7206	Intermediate Similarity	NPD9384	Approved
0.72	Intermediate Similarity	NPD5058	Phase 3
0.7197	Intermediate Similarity	NPD4966	Approved
0.7197	Intermediate Similarity	NPD4967	Phase 2
0.7197	Intermediate Similarity	NPD4965	Approved
0.7197	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD228	Approved
0.7154	Intermediate Similarity	NPD2860	Approved
0.7154	Intermediate Similarity	NPD2859	Approved
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7240	Approved
0.7123	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3020	Approved
0.7113	Intermediate Similarity	NPD4908	Phase 1
0.7105	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3092	Approved
0.7099	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6166	Phase 2
0.7073	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2933	Approved
0.7073	Intermediate Similarity	NPD2934	Approved
0.707	Intermediate Similarity	NPD2977	Approved
0.707	Intermediate Similarity	NPD2978	Approved
0.7068	Intermediate Similarity	NPD5283	Phase 1
0.7063	Intermediate Similarity	NPD1242	Phase 1
0.7034	Intermediate Similarity	NPD3620	Phase 2
0.7034	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4536	Approved
0.7007	Intermediate Similarity	NPD4538	Approved
0.7006	Intermediate Similarity	NPD1934	Approved
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9622	Approved
0.6992	Remote Similarity	NPD7843	Approved
0.6982	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1610	Phase 2
0.697	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7157	Approved
0.6962	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5588	Approved
0.6959	Remote Similarity	NPD5960	Phase 3
0.6957	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8166	Discontinued
0.6939	Remote Similarity	NPD817	Approved
0.6939	Remote Similarity	NPD823	Approved
0.6934	Remote Similarity	NPD3091	Approved
0.6914	Remote Similarity	NPD7199	Phase 2
0.6892	Remote Similarity	NPD7097	Phase 1
0.6886	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4380	Phase 2
0.6879	Remote Similarity	NPD2983	Phase 2
0.6879	Remote Similarity	NPD2982	Phase 2
0.6864	Remote Similarity	NPD8313	Approved
0.6864	Remote Similarity	NPD8312	Approved
0.6853	Remote Similarity	NPD9619	Approved
0.6853	Remote Similarity	NPD9621	Approved
0.6853	Remote Similarity	NPD9620	Approved
0.6849	Remote Similarity	NPD6407	Approved
0.6849	Remote Similarity	NPD6405	Approved
0.6846	Remote Similarity	NPD4108	Discontinued
0.6845	Remote Similarity	NPD6559	Discontinued
0.6836	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5311	Approved
0.6831	Remote Similarity	NPD5310	Approved
0.6818	Remote Similarity	NPD2684	Approved
0.6812	Remote Similarity	NPD1548	Phase 1
0.6809	Remote Similarity	NPD2981	Phase 2
0.6806	Remote Similarity	NPD3018	Phase 2
0.6806	Remote Similarity	NPD5736	Approved
0.6803	Remote Similarity	NPD4060	Phase 1
0.6803	Remote Similarity	NPD1558	Phase 1
0.6792	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD601	Approved
0.6781	Remote Similarity	NPD598	Approved
0.6781	Remote Similarity	NPD597	Approved
0.6778	Remote Similarity	NPD7680	Approved
0.6776	Remote Similarity	NPD3060	Approved
0.6761	Remote Similarity	NPD4659	Approved
0.6757	Remote Similarity	NPD230	Phase 1
0.6753	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD846	Approved
0.6744	Remote Similarity	NPD940	Approved
0.6741	Remote Similarity	NPD9377	Approved
0.6741	Remote Similarity	NPD9379	Approved
0.6738	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1136	Approved
0.6735	Remote Similarity	NPD1132	Approved
0.6735	Remote Similarity	NPD1130	Approved
0.6727	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6671	Approved
0.6714	Remote Similarity	NPD3095	Discontinued
0.6714	Remote Similarity	NPD5846	Approved
0.6714	Remote Similarity	NPD6516	Phase 2
0.6713	Remote Similarity	NPD8651	Approved
0.6712	Remote Similarity	NPD7095	Approved
0.6691	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD825	Approved
0.6689	Remote Similarity	NPD826	Approved
0.6689	Remote Similarity	NPD9570	Approved
0.6689	Remote Similarity	NPD943	Approved
0.6688	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3055	Approved
0.6667	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4236	Phase 3
0.6667	Remote Similarity	NPD5177	Phase 3
0.6667	Remote Similarity	NPD3787	Discontinued
0.6667	Remote Similarity	NPD3053	Approved
0.6667	Remote Similarity	NPD4237	Approved
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4103	Phase 2
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1465	Phase 2
0.6646	Remote Similarity	NPD2801	Approved
0.6645	Remote Similarity	NPD1375	Discontinued
0.6644	Remote Similarity	NPD5735	Approved
0.6642	Remote Similarity	NPD4750	Phase 3
0.6623	Remote Similarity	NPD4628	Phase 3
0.6622	Remote Similarity	NPD6663	Approved
0.6622	Remote Similarity	NPD6233	Phase 2
0.6621	Remote Similarity	NPD6584	Phase 3
0.6618	Remote Similarity	NPD7635	Approved
0.6614	Remote Similarity	NPD844	Approved
0.6603	Remote Similarity	NPD1511	Approved
0.66	Remote Similarity	NPD2568	Approved
0.6599	Remote Similarity	NPD4625	Phase 3
0.6591	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5844	Phase 1
0.6561	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6798	Discontinued
0.6552	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD968	Approved
0.6538	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3028	Approved
0.6536	Remote Similarity	NPD5763	Approved
0.6536	Remote Similarity	NPD5762	Approved
0.6533	Remote Similarity	NPD6355	Discontinued
0.6533	Remote Similarity	NPD4340	Discontinued
0.6532	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4749	Approved
0.6524	Remote Similarity	NPD7075	Discontinued
0.6519	Remote Similarity	NPD1512	Approved
0.6519	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4535	Phase 3
0.6513	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3751	Discontinued
0.6506	Remote Similarity	NPD8127	Discontinued
0.6503	Remote Similarity	NPD3817	Phase 2
0.6503	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5536	Phase 2
0.65	Remote Similarity	NPD3455	Phase 2

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