NPASS Compound

Structure

CID326193 OpenBabel06191716182D 48 50 0 0 1 0 0 0 0 0999 V2000 0.8490 4.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6747 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6747 3.6589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4510 -3.5275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9216 -2.6785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7335 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7924 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4902 -1.8294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2826 2.8098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 3.4314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7139 3.6589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4706 -1.8294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2041 2.8098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4510 -1.8294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7335 3.6589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2629 2.8098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9804 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7727 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1845 2.8098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9412 -2.6785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2433 2.8098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9433 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0943 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9433 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0943 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9433 2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7924 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9804 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.7924 1.9608 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.0943 -0.9804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9433 3.4314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6414 0.4902 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 10 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 26 1 0 0 0 0 8 39 1 0 0 0 0 9 40 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 30 1 0 0 0 0 14 23 2 0 0 0 0 15 24 2 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 25 2 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 39 1 0 0 0 0 20 39 1 0 0 0 0 21 40 1 0 0 0 0 22 28 1 0 0 0 0 22 29 1 0 0 0 0 26 31 1 0 0 0 0 26 41 2 0 0 0 0 27 33 2 0 0 0 0 27 36 1 0 0 0 0 28 33 1 0 0 0 0 28 34 2 0 0 0 0 29 35 1 0 0 0 0 29 37 2 0 0 0 0 30 32 1 0 0 0 0 30 42 2 0 0 0 0 31 35 1 0 0 0 0 31 38 2 0 0 0 0 32 34 1 0 0 0 0 32 36 2 0 0 0 0 33 43 1 0 0 0 0 34 44 1 0 0 0 0 35 45 2 0 0 0 0 36 48 1 0 0 0 0 37 40 1 0 0 0 0 37 46 1 0 0 0 0 38 40 1 0 0 0 0 38 47 1 0 0 0 0 39 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	660.37
Volume:	713.411
LogP:	8.136
LogD:	2.591
LogS:	-3.192
# Rotatable Bonds:	14
TPSA:	135.04
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.116
Synthetic Accessibility Score:	5.151
Fsp3:	0.525
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.865
MDCK Permeability:	2.119248529197648e-05
Pgp-inhibitor:	0.784
Pgp-substrate:	0.917
Human Intestinal Absorption (HIA):	0.211
20% Bioavailability (F20%):	0.78
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	97.97966766357422%
Volume Distribution (VD):	1.563
Pgp-substrate:	1.119447112083435%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.548
CYP2C19-inhibitor:	0.481
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.807
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.818
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.891

ADMET: Excretion

Clearance (CL):	13.773
Half-life (T1/2):	0.019

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.594
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.423
Skin Sensitization:	0.06
Carcinogencity:	0.258
Eye Corrosion:	0.003
Eye Irritation:	0.119
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC326193

Natural Product ID:	NPC326193
*Common Name:**	Yungensin C
IUPAC Name:	n.a.
Synonyms:	Yungensin C
Standard InCHIKey:	UKQRDKMWMFEWPI-KOEQRZSOSA-N
Standard InCHI:	InChI=1S/C40H52O8/c1-10-13-30(42)32-34(44)28(33(43)27-18-20-39(8,48-36(27)32)19-12-15-24(4)5)22-29-35(45)31(26(7)41)38(47)40(9,37(29)46)21-17-25(6)16-11-14-23(2)3/h14-15,17-18,20,43-44,46-47H,10-13,16,19,21-22H2,1-9H3/b25-17+
SMILES:	CCCC(=O)c1c(O)c(CC2=C(O)C(C(=C(C2=O)C(=O)C)O)(C)C/C=C(/CCC=C(C)C)C)c(c2c1OC(C)(CCC=C(C)C)C=C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1631975
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000350] Butyrophenones

*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
NPO17538	Elaphoglossum yungense	Species	Dryopteridaceae	Eukaryota	rhizomes and roots	Yacuchina, Tucumn, Argentina	2008-DEC	PMID[21043474]
NPO17538	Elaphoglossum yungense	Species	Dryopteridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21043474]
NPO17538	Elaphoglossum yungense	Species	Dryopteridaceae	Eukaryota	n.a.	root	n.a.	PMID[21043474]
NPO17538	Elaphoglossum yungense	Species	Dryopteridaceae	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
MIC	2
Others	4

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[484926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	50.0	ug.mL-1	PMID[484926]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	GI	=	92.0	%	PMID[484926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	GI	=	87.0	%	PMID[484926]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	100.0	ug ml-1	PMID[484926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MBC	=	50.0	ug ml-1	PMID[484926]

☑ 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 NPC326193 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	387
0.1-0.2	1578
0.2-0.3	3950
0.3-0.4	9749
0.4-0.5	9463
0.5-0.6	4637
0.6-0.7	6644
0.7-0.8	4730
0.8-0.85	1054
0.85-0.9	456
0.9-0.95	38
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC321148
1.0	High Similarity	NPC323884
1.0	High Similarity	NPC321629
0.9926	High Similarity	NPC316560
0.9926	High Similarity	NPC316911
0.9706	High Similarity	NPC54820
0.9706	High Similarity	NPC268178
0.9706	High Similarity	NPC180501
0.9343	High Similarity	NPC101752
0.9291	High Similarity	NPC325346
0.9281	High Similarity	NPC272844
0.9281	High Similarity	NPC248995
0.9281	High Similarity	NPC254168
0.9214	High Similarity	NPC240305
0.9149	High Similarity	NPC221173
0.9149	High Similarity	NPC471587
0.9143	High Similarity	NPC477056
0.9143	High Similarity	NPC470669
0.9143	High Similarity	NPC477055
0.9143	High Similarity	NPC470668
0.9116	High Similarity	NPC470353
0.9091	High Similarity	NPC11700
0.9085	High Similarity	NPC205006
0.9085	High Similarity	NPC470555
0.9085	High Similarity	NPC156590
0.9085	High Similarity	NPC118840
0.9085	High Similarity	NPC64908
0.9085	High Similarity	NPC147688
0.9078	High Similarity	NPC220062
0.9078	High Similarity	NPC270913
0.9078	High Similarity	NPC53181
0.9078	High Similarity	NPC301217
0.9078	High Similarity	NPC23257
0.9078	High Similarity	NPC303633
0.9078	High Similarity	NPC217186
0.9078	High Similarity	NPC55018
0.9078	High Similarity	NPC96565
0.9078	High Similarity	NPC216978
0.9078	High Similarity	NPC472343
0.906	High Similarity	NPC470352
0.906	High Similarity	NPC470354
0.9028	High Similarity	NPC278175
0.9028	High Similarity	NPC71184
0.9028	High Similarity	NPC257236
0.9028	High Similarity	NPC472447
0.9028	High Similarity	NPC206212
0.9028	High Similarity	NPC472446
0.9021	High Similarity	NPC226636
0.9021	High Similarity	NPC78803
0.9021	High Similarity	NPC217083
0.9021	High Similarity	NPC62840
0.9021	High Similarity	NPC214236
0.9021	High Similarity	NPC59739
0.9021	High Similarity	NPC293852
0.9021	High Similarity	NPC299080
0.9021	High Similarity	NPC11561
0.9014	High Similarity	NPC241100
0.9014	High Similarity	NPC150522
0.9014	High Similarity	NPC475680
0.9014	High Similarity	NPC289660
0.9014	High Similarity	NPC164697
0.9014	High Similarity	NPC270883
0.9014	High Similarity	NPC261227
0.9014	High Similarity	NPC82920
0.9014	High Similarity	NPC235239
0.9014	High Similarity	NPC172986
0.9014	High Similarity	NPC159275
0.9014	High Similarity	NPC305355
0.9007	High Similarity	NPC131130
0.9007	High Similarity	NPC470083
0.9007	High Similarity	NPC219584
0.9007	High Similarity	NPC201395
0.9	High Similarity	NPC174999
0.898	High Similarity	NPC188403
0.8966	High Similarity	NPC329678
0.8958	High Similarity	NPC38219
0.8958	High Similarity	NPC473813
0.8958	High Similarity	NPC473812
0.8958	High Similarity	NPC219915
0.8951	High Similarity	NPC103362
0.8951	High Similarity	NPC110969
0.8951	High Similarity	NPC111201
0.8951	High Similarity	NPC282300
0.8944	High Similarity	NPC78913
0.8944	High Similarity	NPC241975
0.8944	High Similarity	NPC19476
0.8944	High Similarity	NPC18260
0.8936	High Similarity	NPC474624
0.8936	High Similarity	NPC138047
0.8936	High Similarity	NPC131782
0.8929	High Similarity	NPC151113
0.8921	High Similarity	NPC108113
0.8921	High Similarity	NPC93756
0.8921	High Similarity	NPC16197
0.8919	High Similarity	NPC81474
0.8904	High Similarity	NPC283234
0.8897	High Similarity	NPC234629
0.8897	High Similarity	NPC311741
0.8897	High Similarity	NPC469953
0.8897	High Similarity	NPC469935
0.8897	High Similarity	NPC178627
0.8889	High Similarity	NPC36181
0.8889	High Similarity	NPC144499
0.8889	High Similarity	NPC200694
0.8889	High Similarity	NPC204469
0.8881	High Similarity	NPC477272
0.8881	High Similarity	NPC69769
0.8873	High Similarity	NPC199458
0.8873	High Similarity	NPC474487
0.8873	High Similarity	NPC470671
0.8873	High Similarity	NPC474504
0.8873	High Similarity	NPC470672
0.8873	High Similarity	NPC183639
0.8865	High Similarity	NPC470982
0.8865	High Similarity	NPC470983
0.8865	High Similarity	NPC13408
0.8857	High Similarity	NPC125920
0.8849	High Similarity	NPC10971
0.8849	High Similarity	NPC15834
0.8849	High Similarity	NPC215875
0.8844	High Similarity	NPC469933
0.8844	High Similarity	NPC132592
0.8844	High Similarity	NPC160821
0.8836	High Similarity	NPC127059
0.8836	High Similarity	NPC181388
0.8836	High Similarity	NPC20488
0.8836	High Similarity	NPC312973
0.8836	High Similarity	NPC67805
0.8836	High Similarity	NPC142405
0.8836	High Similarity	NPC176229
0.8836	High Similarity	NPC88964
0.8836	High Similarity	NPC301276
0.8836	High Similarity	NPC285630
0.8836	High Similarity	NPC111786
0.8836	High Similarity	NPC246948
0.8836	High Similarity	NPC83357
0.8836	High Similarity	NPC82534
0.8836	High Similarity	NPC54577
0.8836	High Similarity	NPC220418
0.8836	High Similarity	NPC195621
0.8836	High Similarity	NPC470647
0.8836	High Similarity	NPC124729
0.8836	High Similarity	NPC267375
0.8836	High Similarity	NPC475052
0.8836	High Similarity	NPC214774
0.8836	High Similarity	NPC57470
0.8828	High Similarity	NPC188632
0.8828	High Similarity	NPC106985
0.8828	High Similarity	NPC190637
0.8828	High Similarity	NPC196459
0.8828	High Similarity	NPC316816
0.8828	High Similarity	NPC470296
0.8828	High Similarity	NPC18585
0.8828	High Similarity	NPC24821
0.8828	High Similarity	NPC293053
0.8828	High Similarity	NPC112791
0.8828	High Similarity	NPC5990
0.8828	High Similarity	NPC212932
0.8828	High Similarity	NPC166138
0.8828	High Similarity	NPC94794
0.8828	High Similarity	NPC87609
0.8828	High Similarity	NPC214166
0.8828	High Similarity	NPC9117
0.8828	High Similarity	NPC478086
0.8828	High Similarity	NPC185276
0.8824	High Similarity	NPC316625
0.8824	High Similarity	NPC329205
0.8819	High Similarity	NPC248372
0.8819	High Similarity	NPC110038
0.8819	High Similarity	NPC14871
0.8811	High Similarity	NPC139554
0.8811	High Similarity	NPC473076
0.8803	High Similarity	NPC255801
0.8803	High Similarity	NPC322301
0.8794	High Similarity	NPC60667
0.8794	High Similarity	NPC46869
0.8792	High Similarity	NPC476162
0.8784	High Similarity	NPC469932
0.8776	High Similarity	NPC24673
0.8776	High Similarity	NPC249942
0.8776	High Similarity	NPC201731
0.8776	High Similarity	NPC166757
0.8776	High Similarity	NPC110303
0.8776	High Similarity	NPC10990
0.8776	High Similarity	NPC297886
0.8776	High Similarity	NPC285748
0.8776	High Similarity	NPC97716
0.8776	High Similarity	NPC237635
0.8776	High Similarity	NPC473077
0.8776	High Similarity	NPC14001
0.8776	High Similarity	NPC296998
0.8776	High Similarity	NPC300988
0.8776	High Similarity	NPC180477
0.8776	High Similarity	NPC140120
0.8776	High Similarity	NPC104406
0.8776	High Similarity	NPC23728
0.8776	High Similarity	NPC79469
0.8767	High Similarity	NPC235217
0.8767	High Similarity	NPC470673
0.8767	High Similarity	NPC131579

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 NPC326193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	1004
0.2-0.3	1791
0.3-0.4	2755
0.4-0.5	1904
0.5-0.6	957
0.6-0.7	276
0.7-0.8	98
0.8-0.85	13
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9058	High Similarity	NPD6651	Approved
0.9028	High Similarity	NPD7410	Clinical (unspecified phase)
0.8944	High Similarity	NPD2800	Approved
0.8767	High Similarity	NPD4378	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1549	Phase 2
0.8312	Intermediate Similarity	NPD7819	Suspended
0.8301	Intermediate Similarity	NPD7411	Suspended
0.8276	Intermediate Similarity	NPD1510	Phase 2
0.8269	Intermediate Similarity	NPD7075	Discontinued
0.8252	Intermediate Similarity	NPD1240	Approved
0.8235	Intermediate Similarity	NPD4380	Phase 2
0.8219	Intermediate Similarity	NPD2796	Approved
0.8194	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1607	Approved
0.8129	Intermediate Similarity	NPD6801	Discontinued
0.8079	Intermediate Similarity	NPD1511	Approved
0.8077	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3750	Approved
0.7975	Intermediate Similarity	NPD7768	Phase 2
0.7974	Intermediate Similarity	NPD1512	Approved
0.7963	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2801	Approved
0.7925	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2532	Approved
0.7908	Intermediate Similarity	NPD2534	Approved
0.7908	Intermediate Similarity	NPD2533	Approved
0.7898	Intermediate Similarity	NPD1934	Approved
0.7885	Intermediate Similarity	NPD6599	Discontinued
0.7881	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6099	Approved
0.7852	Intermediate Similarity	NPD6100	Approved
0.7843	Intermediate Similarity	NPD6799	Approved
0.7815	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1243	Approved
0.7778	Intermediate Similarity	NPD6959	Discontinued
0.774	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD5124	Phase 1
0.7702	Intermediate Similarity	NPD3749	Approved
0.7688	Intermediate Similarity	NPD3817	Phase 2
0.7667	Intermediate Similarity	NPD3748	Approved
0.764	Intermediate Similarity	NPD3882	Suspended
0.7636	Intermediate Similarity	NPD6166	Phase 2
0.7636	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2313	Discontinued
0.7605	Intermediate Similarity	NPD7054	Approved
0.759	Intermediate Similarity	NPD7473	Discontinued
0.758	Intermediate Similarity	NPD920	Approved
0.758	Intermediate Similarity	NPD5403	Approved
0.7566	Intermediate Similarity	NPD2344	Approved
0.756	Intermediate Similarity	NPD7472	Approved
0.756	Intermediate Similarity	NPD7074	Phase 3
0.755	Intermediate Similarity	NPD2799	Discontinued
0.7548	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3818	Discontinued
0.7532	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.7529	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5953	Discontinued
0.7515	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD422	Phase 1
0.7471	Intermediate Similarity	NPD7251	Discontinued
0.7452	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5401	Approved
0.7431	Intermediate Similarity	NPD9717	Approved
0.7412	Intermediate Similarity	NPD6797	Phase 2
0.7397	Intermediate Similarity	NPD1203	Approved
0.7394	Intermediate Similarity	NPD5494	Approved
0.7383	Intermediate Similarity	NPD3268	Approved
0.7375	Intermediate Similarity	NPD3226	Approved
0.7372	Intermediate Similarity	NPD2309	Approved
0.7368	Intermediate Similarity	NPD6559	Discontinued
0.7365	Intermediate Similarity	NPD6832	Phase 2
0.732	Intermediate Similarity	NPD7033	Discontinued
0.732	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7305	Intermediate Similarity	NPD5710	Approved
0.7305	Intermediate Similarity	NPD5711	Approved
0.7279	Intermediate Similarity	NPD2797	Approved
0.7278	Intermediate Similarity	NPD7390	Discontinued
0.7267	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5402	Approved
0.7244	Intermediate Similarity	NPD2654	Approved
0.723	Intermediate Similarity	NPD2798	Approved
0.7229	Intermediate Similarity	NPD919	Approved
0.7226	Intermediate Similarity	NPD2346	Discontinued
0.7225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4308	Phase 3
0.7203	Intermediate Similarity	NPD1548	Phase 1
0.7192	Intermediate Similarity	NPD3972	Approved
0.7171	Intermediate Similarity	NPD943	Approved
0.7168	Intermediate Similarity	NPD6104	Discontinued
0.716	Intermediate Similarity	NPD3926	Phase 2
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7133	Intermediate Similarity	NPD4908	Phase 1
0.7123	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4360	Phase 2
0.7111	Intermediate Similarity	NPD4363	Phase 3
0.7095	Intermediate Similarity	NPD3225	Approved
0.7093	Intermediate Similarity	NPD5844	Phase 1
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.7073	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4361	Phase 2
0.7072	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8434	Phase 2
0.7055	Intermediate Similarity	NPD7458	Discontinued
0.7052	Intermediate Similarity	NPD1729	Discontinued
0.7048	Intermediate Similarity	NPD4288	Approved
0.7047	Intermediate Similarity	NPD3267	Approved
0.7047	Intermediate Similarity	NPD3266	Approved
0.7012	Intermediate Similarity	NPD6585	Discontinued
0.7011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1610	Phase 2
0.7	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1465	Phase 2
0.698	Remote Similarity	NPD8651	Approved
0.6972	Remote Similarity	NPD1241	Discontinued
0.6968	Remote Similarity	NPD7584	Approved
0.6966	Remote Similarity	NPD9545	Approved
0.6948	Remote Similarity	NPD4307	Phase 2
0.6944	Remote Similarity	NPD9493	Approved
0.6933	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD411	Approved
0.6919	Remote Similarity	NPD2403	Approved
0.6919	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD447	Suspended
0.6889	Remote Similarity	NPD4287	Approved
0.6886	Remote Similarity	NPD5761	Phase 2
0.6886	Remote Similarity	NPD5760	Phase 2
0.6875	Remote Similarity	NPD7003	Approved
0.6871	Remote Similarity	NPD5049	Phase 3
0.6867	Remote Similarity	NPD5889	Approved
0.6867	Remote Similarity	NPD5890	Approved
0.6846	Remote Similarity	NPD1608	Approved
0.6845	Remote Similarity	NPD2296	Approved
0.6839	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5404	Approved
0.6835	Remote Similarity	NPD5405	Approved
0.6835	Remote Similarity	NPD5406	Approved
0.6835	Remote Similarity	NPD5408	Approved
0.6818	Remote Similarity	NPD3764	Approved
0.6802	Remote Similarity	NPD7229	Phase 3
0.6798	Remote Similarity	NPD8313	Approved
0.6798	Remote Similarity	NPD8312	Approved
0.6797	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD230	Phase 1
0.6795	Remote Similarity	NPD1933	Approved
0.6792	Remote Similarity	NPD1471	Phase 3
0.6779	Remote Similarity	NPD1201	Approved
0.6776	Remote Similarity	NPD1019	Discontinued
0.6776	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD651	Clinical (unspecified phase)
0.675	Remote Similarity	NPD2424	Discontinued
0.6743	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD2354	Approved
0.6725	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1164	Approved
0.6711	Remote Similarity	NPD1470	Approved
0.671	Remote Similarity	NPD6798	Discontinued
0.6708	Remote Similarity	NPD1652	Phase 2
0.6688	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6002	Phase 3
0.6687	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6005	Phase 3
0.6687	Remote Similarity	NPD6004	Phase 3
0.6686	Remote Similarity	NPD8455	Phase 2
0.6686	Remote Similarity	NPD3446	Phase 1
0.6685	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD8032	Phase 2
0.6648	Remote Similarity	NPD3751	Discontinued
0.6647	Remote Similarity	NPD7199	Phase 2
0.6647	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6696	Suspended
0.6645	Remote Similarity	NPD7095	Approved
0.6644	Remote Similarity	NPD1778	Approved
0.6644	Remote Similarity	NPD17	Approved
0.6644	Remote Similarity	NPD6671	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