NPASS Compound

Structure

CID55158 OpenBabel06191715392D 39 43 0 0 1 0 0 0 0 0999 V2000 -3.4705 -5.9034 0.0000 C 0 0 0 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 0.9706 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9659 -2.3321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8795 -2.7388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2614 -3.9144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4422 -0.6214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6342 -2.3440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1569 -2.9199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0354 -1.5350 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0409 -1.4305 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9840 -3.7333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1750 -4.3211 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -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 -2.2434 -2.5131 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8330 -0.4523 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 -0.0000 1.0000 0.0000 C 0 0 1 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 -5.8975 -4.1401 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 -4.2795 -5.3157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -1.3773 -3.0131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6990 0.0477 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 33 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 13 1 0 0 0 0 8 19 2 0 0 0 0 9 28 1 0 0 0 0 10 37 1 0 0 0 0 11 36 1 0 0 0 0 14 10 1 1 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 11 1 1 0 0 0 15 25 1 0 0 0 0 16 17 2 0 0 0 0 16 29 1 0 0 0 0 17 33 1 0 0 0 0 18 26 2 0 0 0 0 18 34 1 0 0 0 0 19 26 1 0 0 0 0 19 35 1 0 0 0 0 20 9 1 6 0 0 0 20 21 1 0 0 0 0 20 38 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 1 0 0 0 22 23 1 0 0 0 0 22 31 1 6 0 0 0 23 27 1 0 0 0 0 23 32 1 1 0 0 0 24 12 1 6 0 0 0 24 36 1 0 0 0 0 25 13 1 6 0 0 0 25 37 1 0 0 0 0 26 39 1 0 0 0 0 27 38 1 0 0 0 0 27 39 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	550.21
Volume:	522.43
LogP:	0.809
LogD:	1.415
LogS:	-4.002
# Rotatable Bonds:	8
TPSA:	165.76
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	4.549
Fsp3:	0.556
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.172
MDCK Permeability:	3.2934825867414474e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.22
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.252

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.17
Plasma Protein Binding (PPB):	43.793270111083984%
Volume Distribution (VD):	0.305
Pgp-substrate:	21.769922256469727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.807
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.251
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.305
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.399

ADMET: Excretion

Clearance (CL):	3.982
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.634
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.266
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.207
Skin Sensitization:	0.929
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.3

Download Data

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

Natural Product: NPC55158

Natural Product ID:	NPC55158
*Common Name:**	(+)-Eucommin A
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6S,6aR)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	(+)-Eucommin A
Standard InCHIKey:	GLGVEKKQPFRBAS-UOVCOODASA-N
Standard InCHI:	InChI=1S/C27H34O12/c1-33-17-6-12(4-5-16(17)29)24-14-10-37-25(15(14)11-36-24)13-7-18(34-2)26(19(8-13)35-3)39-27-23(32)22(31)21(30)20(9-28)38-27/h4-8,14-15,20-25,27-32H,9-11H2,1-3H3/t14-,15-,20+,21+,22-,23+,24+,25+,27-/m0/s1
SMILES:	OC[C@H]1O[C@@H](Oc2c(OC)cc(cc2OC)[C@H]2OC[C@H]3[C@@H]2CO[C@@H]3c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076999
PubChem CID:	442836
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	aerial parts	Khon Kaen Province, Thailand	2006-Aug	PMID[19943620]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	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	7

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	<	0.1	uM	PMID[522912]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[522912]
NPT396	Cell Line	T47D	Homo sapiens	Activity	<	0.1	uM	PMID[522912]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	2.0	uM	PMID[522912]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[522912]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	>	90.0	%	PMID[522912]

☑ 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 NPC55158 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	453
0.1-0.2	1391
0.2-0.3	3756
0.3-0.4	9585
0.4-0.5	9299
0.5-0.6	5520
0.6-0.7	7888
0.7-0.8	3698
0.8-0.85	730
0.85-0.9	281
0.9-0.95	71
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC51328
1.0	High Similarity	NPC286235
0.9929	High Similarity	NPC130449
0.9929	High Similarity	NPC248132
0.9858	High Similarity	NPC39657
0.9716	High Similarity	NPC279298
0.9716	High Similarity	NPC22150
0.9716	High Similarity	NPC38041
0.9648	High Similarity	NPC112861
0.9645	High Similarity	NPC472712
0.9645	High Similarity	NPC472713
0.9645	High Similarity	NPC187774
0.9645	High Similarity	NPC118385
0.9645	High Similarity	NPC473046
0.9577	High Similarity	NPC18979
0.9574	High Similarity	NPC477898
0.9574	High Similarity	NPC470950
0.9574	High Similarity	NPC185307
0.9517	High Similarity	NPC472710
0.9517	High Similarity	NPC472709
0.9507	High Similarity	NPC283995
0.9507	High Similarity	NPC470235
0.9507	High Similarity	NPC25292
0.9507	High Similarity	NPC129417
0.9507	High Similarity	NPC84181
0.9507	High Similarity	NPC473045
0.9504	High Similarity	NPC472714
0.9504	High Similarity	NPC5262
0.9504	High Similarity	NPC189115
0.9504	High Similarity	NPC246947
0.9504	High Similarity	NPC476356
0.9504	High Similarity	NPC469559
0.9448	High Similarity	NPC95392
0.9448	High Similarity	NPC35877
0.9448	High Similarity	NPC55715
0.9441	High Similarity	NPC475096
0.9437	High Similarity	NPC473044
0.9437	High Similarity	NPC46092
0.9433	High Similarity	NPC472711
0.9433	High Similarity	NPC469661
0.9384	High Similarity	NPC475224
0.9384	High Similarity	NPC98624
0.9379	High Similarity	NPC166584
0.9379	High Similarity	NPC270751
0.9379	High Similarity	NPC301961
0.9375	High Similarity	NPC99515
0.9375	High Similarity	NPC190714
0.9371	High Similarity	NPC470097
0.9371	High Similarity	NPC471415
0.9371	High Similarity	NPC114119
0.9362	High Similarity	NPC177868
0.9362	High Similarity	NPC226547
0.931	High Similarity	NPC213074
0.931	High Similarity	NPC227902
0.931	High Similarity	NPC193473
0.931	High Similarity	NPC275284
0.931	High Similarity	NPC114505
0.931	High Similarity	NPC224674
0.931	High Similarity	NPC31325
0.931	High Similarity	NPC15956
0.9306	High Similarity	NPC469586
0.9301	High Similarity	NPC185071
0.9301	High Similarity	NPC12728
0.9301	High Similarity	NPC298317
0.9301	High Similarity	NPC255566
0.9291	High Similarity	NPC98777
0.9291	High Similarity	NPC156376
0.9291	High Similarity	NPC212770
0.9252	High Similarity	NPC238140
0.9247	High Similarity	NPC175976
0.9241	High Similarity	NPC276753
0.9241	High Similarity	NPC324492
0.9241	High Similarity	NPC212890
0.9241	High Similarity	NPC226540
0.9241	High Similarity	NPC205796
0.9241	High Similarity	NPC317053
0.9241	High Similarity	NPC125755
0.9231	High Similarity	NPC475084
0.9231	High Similarity	NPC302506
0.922	High Similarity	NPC185908
0.922	High Similarity	NPC283949
0.922	High Similarity	NPC470413
0.922	High Similarity	NPC65530
0.922	High Similarity	NPC59324
0.922	High Similarity	NPC138738
0.922	High Similarity	NPC474039
0.9178	High Similarity	NPC320671
0.9178	High Similarity	NPC328567
0.9178	High Similarity	NPC327412
0.9178	High Similarity	NPC320970
0.9172	High Similarity	NPC477702
0.9172	High Similarity	NPC43508
0.9172	High Similarity	NPC474749
0.9172	High Similarity	NPC161700
0.9172	High Similarity	NPC277867
0.9172	High Similarity	NPC178014
0.9172	High Similarity	NPC42716
0.9172	High Similarity	NPC11422
0.9172	High Similarity	NPC180953
0.9172	High Similarity	NPC307466
0.9172	High Similarity	NPC476301
0.9167	High Similarity	NPC81638
0.9161	High Similarity	NPC471908
0.9149	High Similarity	NPC52277
0.9149	High Similarity	NPC242028
0.9149	High Similarity	NPC172818
0.9149	High Similarity	NPC203230
0.9149	High Similarity	NPC25695
0.9149	High Similarity	NPC177035
0.9149	High Similarity	NPC199459
0.9133	High Similarity	NPC159922
0.9128	High Similarity	NPC302610
0.9116	High Similarity	NPC304048
0.9116	High Similarity	NPC226153
0.9116	High Similarity	NPC71726
0.911	High Similarity	NPC162193
0.9103	High Similarity	NPC79429
0.9103	High Similarity	NPC168579
0.9103	High Similarity	NPC471667
0.9103	High Similarity	NPC471063
0.9103	High Similarity	NPC76176
0.9103	High Similarity	NPC469313
0.9103	High Similarity	NPC179521
0.9103	High Similarity	NPC138227
0.9103	High Similarity	NPC217635
0.9091	High Similarity	NPC56091
0.9091	High Similarity	NPC184797
0.9091	High Similarity	NPC46591
0.9091	High Similarity	NPC266197
0.9091	High Similarity	NPC309124
0.9091	High Similarity	NPC106944
0.9091	High Similarity	NPC291101
0.9085	High Similarity	NPC195196
0.9078	High Similarity	NPC101624
0.9078	High Similarity	NPC184938
0.9078	High Similarity	NPC150534
0.9078	High Similarity	NPC236522
0.9078	High Similarity	NPC34103
0.9078	High Similarity	NPC142547
0.9078	High Similarity	NPC165155
0.9078	High Similarity	NPC99572
0.9078	High Similarity	NPC126409
0.9078	High Similarity	NPC141765
0.9078	High Similarity	NPC24490
0.9078	High Similarity	NPC135777
0.9054	High Similarity	NPC470098
0.9054	High Similarity	NPC470826
0.9054	High Similarity	NPC106138
0.9054	High Similarity	NPC473266
0.9048	High Similarity	NPC473480
0.9048	High Similarity	NPC15538
0.9038	High Similarity	NPC59516
0.9034	High Similarity	NPC278961
0.9034	High Similarity	NPC113680
0.9034	High Similarity	NPC252169
0.9034	High Similarity	NPC474808
0.9034	High Similarity	NPC37793
0.9021	High Similarity	NPC232164
0.9021	High Similarity	NPC236306
0.9021	High Similarity	NPC88640
0.9021	High Similarity	NPC193666
0.9021	High Similarity	NPC123526
0.9021	High Similarity	NPC292487
0.9021	High Similarity	NPC473739
0.9014	High Similarity	NPC164857
0.9013	High Similarity	NPC11411
0.9007	High Similarity	NPC187194
0.9007	High Similarity	NPC13745
0.9007	High Similarity	NPC251981
0.9007	High Similarity	NPC244983
0.9007	High Similarity	NPC107478
0.9007	High Similarity	NPC170694
0.9007	High Similarity	NPC287745
0.9007	High Similarity	NPC476411
0.9007	High Similarity	NPC326095
0.9007	High Similarity	NPC48863
0.9	High Similarity	NPC21902
0.8993	High Similarity	NPC225815
0.8993	High Similarity	NPC145979
0.8993	High Similarity	NPC185955
0.8993	High Similarity	NPC214326
0.8993	High Similarity	NPC469706
0.8993	High Similarity	NPC9933
0.8993	High Similarity	NPC260781
0.8993	High Similarity	NPC218041
0.8993	High Similarity	NPC182368
0.8993	High Similarity	NPC469707
0.8986	High Similarity	NPC280945
0.898	High Similarity	NPC260397
0.898	High Similarity	NPC241846
0.898	High Similarity	NPC93610
0.8966	High Similarity	NPC107161
0.8966	High Similarity	NPC287124
0.8966	High Similarity	NPC80326
0.8966	High Similarity	NPC253878
0.8958	High Similarity	NPC55793
0.8951	High Similarity	NPC304152
0.8944	High Similarity	NPC470236
0.894	High Similarity	NPC61604
0.894	High Similarity	NPC115466

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 NPC55158 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	771
0.2-0.3	1869
0.3-0.4	2879
0.4-0.5	1746
0.5-0.6	1027
0.6-0.7	436
0.7-0.8	66
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8652	High Similarity	NPD3027	Phase 3
0.8625	High Similarity	NPD7228	Approved
0.8601	High Similarity	NPD1612	Clinical (unspecified phase)
0.8601	High Similarity	NPD1613	Approved
0.8535	High Similarity	NPD6234	Discontinued
0.8408	Intermediate Similarity	NPD4965	Approved
0.8408	Intermediate Similarity	NPD4967	Phase 2
0.8408	Intermediate Similarity	NPD4966	Approved
0.8322	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1653	Approved
0.8252	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD37	Approved
0.8199	Intermediate Similarity	NPD7199	Phase 2
0.8182	Intermediate Similarity	NPD7074	Phase 3
0.8171	Intermediate Similarity	NPD3818	Discontinued
0.8146	Intermediate Similarity	NPD6674	Discontinued
0.8133	Intermediate Similarity	NPD7266	Discontinued
0.8121	Intermediate Similarity	NPD7054	Approved
0.8084	Intermediate Similarity	NPD7240	Approved
0.8072	Intermediate Similarity	NPD7472	Approved
0.7988	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD4908	Phase 1
0.787	Intermediate Similarity	NPD7251	Discontinued
0.7838	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD3705	Approved
0.7832	Intermediate Similarity	NPD1610	Phase 2
0.7832	Intermediate Similarity	NPD1091	Approved
0.7824	Intermediate Similarity	NPD7808	Phase 3
0.7811	Intermediate Similarity	NPD6797	Phase 2
0.7764	Intermediate Similarity	NPD1934	Approved
0.7755	Intermediate Similarity	NPD2861	Phase 2
0.7719	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6559	Discontinued
0.7643	Intermediate Similarity	NPD5058	Phase 3
0.7637	Intermediate Similarity	NPD7680	Approved
0.763	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1357	Approved
0.7622	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6166	Phase 2
0.7607	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3620	Phase 2
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4749	Approved
0.7483	Intermediate Similarity	NPD2982	Phase 2
0.7483	Intermediate Similarity	NPD2983	Phase 2
0.747	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5283	Phase 1
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7417	Intermediate Similarity	NPD4625	Phase 3
0.7415	Intermediate Similarity	NPD2981	Phase 2
0.741	Intermediate Similarity	NPD3882	Suspended
0.74	Intermediate Similarity	NPD3018	Phase 2
0.7394	Intermediate Similarity	NPD2801	Approved
0.7394	Intermediate Similarity	NPD2977	Approved
0.7394	Intermediate Similarity	NPD2978	Approved
0.7394	Intermediate Similarity	NPD8455	Phase 2
0.7362	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7157	Approved
0.7342	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5735	Approved
0.7308	Intermediate Similarity	NPD5588	Approved
0.7305	Intermediate Similarity	NPD228	Approved
0.7283	Intermediate Similarity	NPD5844	Phase 1
0.7278	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7254	Intermediate Similarity	NPD7843	Approved
0.7246	Intermediate Similarity	NPD3817	Phase 2
0.7244	Intermediate Similarity	NPD4536	Approved
0.7244	Intermediate Similarity	NPD4538	Approved
0.7244	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3382	Approved
0.7229	Intermediate Similarity	NPD3384	Approved
0.7229	Intermediate Similarity	NPD3383	Approved
0.7215	Intermediate Similarity	NPD1375	Discontinued
0.7211	Intermediate Similarity	NPD5125	Phase 3
0.7211	Intermediate Similarity	NPD5126	Approved
0.7207	Intermediate Similarity	NPD6842	Approved
0.7207	Intermediate Similarity	NPD6843	Phase 3
0.7207	Intermediate Similarity	NPD6841	Approved
0.72	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1465	Phase 2
0.7163	Intermediate Similarity	NPD3021	Approved
0.7163	Intermediate Similarity	NPD3022	Approved
0.7161	Intermediate Similarity	NPD1558	Phase 1
0.716	Intermediate Similarity	NPD1511	Approved
0.716	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7097	Phase 1
0.7133	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1652	Phase 2
0.7115	Intermediate Similarity	NPD5124	Phase 1
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7115	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4380	Phase 2
0.7108	Intermediate Similarity	NPD4675	Approved
0.7108	Intermediate Similarity	NPD4678	Approved
0.7107	Intermediate Similarity	NPD5762	Approved
0.7107	Intermediate Similarity	NPD5763	Approved
0.7105	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7092	Intermediate Similarity	NPD2684	Approved
0.7089	Intermediate Similarity	NPD4108	Discontinued
0.7089	Intermediate Similarity	NPD5960	Phase 3
0.7086	Intermediate Similarity	NPD8651	Approved
0.7081	Intermediate Similarity	NPD6331	Phase 2
0.7081	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4110	Phase 3
0.7078	Intermediate Similarity	NPD7095	Approved
0.7073	Intermediate Similarity	NPD1512	Approved
0.707	Intermediate Similarity	NPD6653	Approved
0.7069	Intermediate Similarity	NPD7473	Discontinued
0.7048	Intermediate Similarity	NPD4005	Discontinued
0.7044	Intermediate Similarity	NPD6100	Approved
0.7044	Intermediate Similarity	NPD6099	Approved
0.7041	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6190	Approved
0.7035	Intermediate Similarity	NPD8127	Discontinued
0.7022	Intermediate Similarity	NPD7549	Discontinued
0.7019	Intermediate Similarity	NPD5177	Phase 3
0.7019	Intermediate Similarity	NPD4236	Phase 3
0.7019	Intermediate Similarity	NPD4237	Approved
0.7017	Intermediate Similarity	NPD7906	Approved
0.7012	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7447	Phase 1
0.7011	Intermediate Similarity	NPD2489	Approved
0.7011	Intermediate Similarity	NPD27	Approved
0.7	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7124	Phase 2
0.6994	Remote Similarity	NPD6232	Discontinued
0.6986	Remote Similarity	NPD6671	Approved
0.6983	Remote Similarity	NPD8313	Approved
0.6983	Remote Similarity	NPD7312	Approved
0.6983	Remote Similarity	NPD7311	Approved
0.6983	Remote Similarity	NPD8312	Approved
0.6983	Remote Similarity	NPD7310	Approved
0.6983	Remote Similarity	NPD7313	Approved
0.6982	Remote Similarity	NPD5772	Approved
0.6982	Remote Similarity	NPD7819	Suspended
0.6982	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5773	Approved
0.6975	Remote Similarity	NPD7466	Approved
0.6975	Remote Similarity	NPD3892	Phase 2
0.6975	Remote Similarity	NPD4628	Phase 3
0.6975	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4663	Approved
0.6954	Remote Similarity	NPD2969	Approved
0.6954	Remote Similarity	NPD2970	Approved
0.6951	Remote Similarity	NPD7213	Phase 3
0.6951	Remote Similarity	NPD7212	Phase 2
0.6944	Remote Similarity	NPD8053	Approved
0.6944	Remote Similarity	NPD7309	Approved
0.6944	Remote Similarity	NPD8054	Approved
0.6943	Remote Similarity	NPD4140	Approved
0.6937	Remote Similarity	NPD2161	Phase 2
0.6933	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3751	Discontinued
0.6923	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3060	Approved
0.6908	Remote Similarity	NPD5327	Phase 3
0.6905	Remote Similarity	NPD7028	Phase 2
0.6897	Remote Similarity	NPD3051	Approved
0.6897	Remote Similarity	NPD6071	Discontinued
0.6897	Remote Similarity	NPD7229	Phase 3
0.6894	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3540	Phase 1
0.6894	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4577	Approved
0.6889	Remote Similarity	NPD4578	Approved
0.6887	Remote Similarity	NPD422	Phase 1
0.6883	Remote Similarity	NPD6584	Phase 3
0.6879	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6516	Phase 2
0.6867	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7526	Approved
0.6867	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5846	Approved
0.6867	Remote Similarity	NPD52	Approved
0.6855	Remote Similarity	NPD6353	Approved
0.6852	Remote Similarity	NPD1549	Phase 2
0.6848	Remote Similarity	NPD4357	Discontinued
0.6842	Remote Similarity	NPD2563	Approved
0.6842	Remote Similarity	NPD5402	Approved
0.6842	Remote Similarity	NPD2560	Approved
0.6835	Remote Similarity	NPD2238	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