NPASS Compound

Structure

CID227160 OpenBabel06191716022D 27 31 0 0 1 0 0 0 0 0999 V2000 -4.3768 -3.4983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8453 -4.2672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3407 -0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2542 -1.1026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6362 -2.2781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8169 1.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9911 -0.7077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5317 -1.2836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4102 0.1013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5843 0.2058 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3588 -2.0971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5497 -2.6849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6181 -0.8769 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7922 1.1840 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2723 -2.5038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6543 -3.6794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2479 -1.3769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0738 1.6840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3633 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 25 1 0 0 0 0 10 24 1 0 0 0 0 11 26 1 0 0 0 0 11 27 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 10 1 1 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 19 27 1 0 0 0 0 20 12 1 1 0 0 0 20 24 1 0 0 0 0 21 13 1 6 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.14
Volume:	365.912
LogP:	3.429
LogD:	3.252
LogS:	-5.245
# Rotatable Bonds:	4
TPSA:	55.38
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.821
Synthetic Accessibility Score:	3.629
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.917
MDCK Permeability:	7.024791557341814e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	93.50000762939453%
Volume Distribution (VD):	0.869
Pgp-substrate:	2.7935104370117188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.782
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.585
CYP2C9-substrate:	0.685
CYP2D6-inhibitor:	0.845
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.799

ADMET: Excretion

Clearance (CL):	12.091
Half-life (T1/2):	0.214

ADMET: Toxicity

hERG Blockers:	0.695
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.477
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.854
Skin Sensitization:	0.882
Carcinogencity:	0.754
Eye Corrosion:	0.003
Eye Irritation:	0.108
Respiratory Toxicity:	0.428

Download Data

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

Natural Product: NPC227160

Natural Product ID:	NPC227160
*Common Name:**	Fargesin
IUPAC Name:	5-[(3S,3aR,6R,6aR)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-1,3-benzodioxole
Synonyms:
Standard InCHIKey:	AWOGQCSIVCQXBT-LATRNWQMSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-22-16-5-3-12(7-18(16)23-2)20-14-9-25-21(15(14)10-24-20)13-4-6-17-19(8-13)27-11-26-17/h3-8,14-15,20-21H,9-11H2,1-2H3/t14-,15-,20-,21+/m0/s1
SMILES:	COc1ccc(cc1OC)[C@H]1[C@H]2CO[C@H](c3ccc4c(c3)OCO4)[C@H]2CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2442732
PubChem CID:	10926754
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[17628872]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19370929]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22080044]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[7779269]
NPO1918	Magnolia kobus	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7142	Corydalis suaveolens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14951	Zanthoxylum acanthopodium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1918	Magnolia kobus	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14951	Zanthoxylum acanthopodium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7142	Corydalis suaveolens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1918	Magnolia kobus	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1918	Magnolia kobus	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14951	Zanthoxylum acanthopodium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19004	Dryobalanops camphora	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16988	Pseudodistoma novaezelandiae	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19078	Lophocolea bidentata	Species	Lophocoleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13228	Farfugium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7142	Corydalis suaveolens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18811	Magnolia biondii	Species	Magnoliaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Inhibition	=	29.8	%	PMID[528774]

☑ 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 NPC227160 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	482
0.1-0.2	1431
0.2-0.3	3899
0.3-0.4	10759
0.4-0.5	8339
0.5-0.6	7268
0.6-0.7	7888
0.7-0.8	2089
0.8-0.85	339
0.85-0.9	142
0.9-0.95	46
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC82111
0.9919	High Similarity	NPC233224
0.9919	High Similarity	NPC271208
0.9762	High Similarity	NPC33611
0.9762	High Similarity	NPC100223
0.9762	High Similarity	NPC171928
0.9762	High Similarity	NPC16830
0.9762	High Similarity	NPC158526
0.9762	High Similarity	NPC129687
0.9758	High Similarity	NPC57119
0.9758	High Similarity	NPC165128
0.9758	High Similarity	NPC226862
0.9758	High Similarity	NPC158471
0.9688	High Similarity	NPC474139
0.9688	High Similarity	NPC189474
0.9609	High Similarity	NPC47181
0.9609	High Similarity	NPC31530
0.9606	High Similarity	NPC7744
0.9535	High Similarity	NPC148893
0.9535	High Similarity	NPC49235
0.9535	High Similarity	NPC25333
0.9535	High Similarity	NPC18576
0.9531	High Similarity	NPC266848
0.9531	High Similarity	NPC136750
0.952	High Similarity	NPC158737
0.9466	High Similarity	NPC123526
0.9466	High Similarity	NPC88640
0.9466	High Similarity	NPC193666
0.9453	High Similarity	NPC261812
0.9453	High Similarity	NPC72046
0.9453	High Similarity	NPC65183
0.9435	High Similarity	NPC121783
0.9435	High Similarity	NPC34902
0.9435	High Similarity	NPC18449
0.9389	High Similarity	NPC101807
0.9389	High Similarity	NPC469981
0.9375	High Similarity	NPC192255
0.9323	High Similarity	NPC312199
0.9318	High Similarity	NPC113550
0.9308	High Similarity	NPC170779
0.9308	High Similarity	NPC90083
0.9302	High Similarity	NPC219671
0.9302	High Similarity	NPC147616
0.9302	High Similarity	NPC104077
0.9302	High Similarity	NPC259742
0.9248	High Similarity	NPC46591
0.9237	High Similarity	NPC142547
0.9237	High Similarity	NPC135777
0.9194	High Similarity	NPC126935
0.9194	High Similarity	NPC301641
0.9194	High Similarity	NPC80241
0.9194	High Similarity	NPC312713
0.9194	High Similarity	NPC65933
0.9194	High Similarity	NPC172676
0.9194	High Similarity	NPC57268
0.9194	High Similarity	NPC216929
0.9185	High Similarity	NPC298317
0.9185	High Similarity	NPC255566
0.9185	High Similarity	NPC265154
0.9179	High Similarity	NPC471908
0.9167	High Similarity	NPC121651
0.9147	High Similarity	NPC134764
0.9147	High Similarity	NPC171550
0.9141	High Similarity	NPC222127
0.9141	High Similarity	NPC82862
0.9111	High Similarity	NPC311057
0.9111	High Similarity	NPC474295
0.9104	High Similarity	NPC56091
0.9098	High Similarity	NPC185908
0.9091	High Similarity	NPC174191
0.907	High Similarity	NPC476748
0.9062	High Similarity	NPC8050
0.9062	High Similarity	NPC473093
0.9062	High Similarity	NPC473092
0.9044	High Similarity	NPC12728
0.9044	High Similarity	NPC185071
0.9032	High Similarity	NPC344161
0.903	High Similarity	NPC156376
0.9023	High Similarity	NPC11453
0.9008	High Similarity	NPC471505
0.8992	High Similarity	NPC54321
0.8992	High Similarity	NPC328682
0.8992	High Similarity	NPC281864
0.8984	High Similarity	NPC50683
0.8984	High Similarity	NPC206882
0.8984	High Similarity	NPC112571
0.8984	High Similarity	NPC40352
0.8984	High Similarity	NPC213711
0.8984	High Similarity	NPC285725
0.8978	High Similarity	NPC477701
0.8978	High Similarity	NPC141569
0.8978	High Similarity	NPC166884
0.8978	High Similarity	NPC179521
0.8971	High Similarity	NPC472562
0.8971	High Similarity	NPC246947
0.8971	High Similarity	NPC80326
0.8963	High Similarity	NPC216434
0.8963	High Similarity	NPC103448
0.8963	High Similarity	NPC177868
0.8955	High Similarity	NPC166184
0.8955	High Similarity	NPC283949
0.8947	High Similarity	NPC184938
0.8947	High Similarity	NPC101624
0.8947	High Similarity	NPC150534
0.8939	High Similarity	NPC196937
0.8939	High Similarity	NPC1474
0.8931	High Similarity	NPC40432
0.8931	High Similarity	NPC27843
0.8931	High Similarity	NPC115207
0.8931	High Similarity	NPC161557
0.8931	High Similarity	NPC7171
0.8931	High Similarity	NPC228346
0.8931	High Similarity	NPC158079
0.8913	High Similarity	NPC205316
0.8905	High Similarity	NPC477898
0.8897	High Similarity	NPC300798
0.8897	High Similarity	NPC58137
0.8881	High Similarity	NPC143895
0.8864	High Similarity	NPC181049
0.8864	High Similarity	NPC207400
0.8864	High Similarity	NPC106739
0.8849	High Similarity	NPC3982
0.8846	High Similarity	NPC470084
0.8841	High Similarity	NPC191158
0.8841	High Similarity	NPC84181
0.8841	High Similarity	NPC177644
0.8837	High Similarity	NPC186845
0.8837	High Similarity	NPC88297
0.8837	High Similarity	NPC9891
0.8832	High Similarity	NPC174522
0.8832	High Similarity	NPC287124
0.8832	High Similarity	NPC302506
0.8824	High Similarity	NPC226547
0.8824	High Similarity	NPC278076
0.8797	High Similarity	NPC169973
0.8777	High Similarity	NPC469586
0.8777	High Similarity	NPC22150
0.8777	High Similarity	NPC279298
0.8777	High Similarity	NPC38041
0.8777	High Similarity	NPC180953
0.8769	High Similarity	NPC98745
0.8769	High Similarity	NPC177167
0.8768	High Similarity	NPC474808
0.8759	High Similarity	NPC472711
0.8741	High Similarity	NPC32189
0.8731	High Similarity	NPC110958
0.8731	High Similarity	NPC19890
0.8722	High Similarity	NPC4940
0.8714	High Similarity	NPC112861
0.8714	High Similarity	NPC276753
0.8714	High Similarity	NPC205796
0.8712	High Similarity	NPC275950
0.8712	High Similarity	NPC64201
0.8712	High Similarity	NPC187998
0.8712	High Similarity	NPC145305
0.8712	High Similarity	NPC257582
0.8712	High Similarity	NPC242807
0.8712	High Similarity	NPC77040
0.8712	High Similarity	NPC42300
0.8712	High Similarity	NPC241522
0.8712	High Similarity	NPC174495
0.8712	High Similarity	NPC92164
0.8712	High Similarity	NPC153739
0.8705	High Similarity	NPC92693
0.8705	High Similarity	NPC218841
0.8702	High Similarity	NPC21867
0.8702	High Similarity	NPC129570
0.8702	High Similarity	NPC45774
0.8702	High Similarity	NPC282703
0.8702	High Similarity	NPC11258
0.8702	High Similarity	NPC184733
0.8702	High Similarity	NPC128208
0.8696	High Similarity	NPC176586
0.8696	High Similarity	NPC210354
0.8676	High Similarity	NPC196420
0.8676	High Similarity	NPC474039
0.8676	High Similarity	NPC14022
0.8667	High Similarity	NPC99572
0.8667	High Similarity	NPC236522
0.8667	High Similarity	NPC126409
0.8657	High Similarity	NPC205915
0.8647	High Similarity	NPC277804
0.8647	High Similarity	NPC476345
0.8643	High Similarity	NPC18979
0.8643	High Similarity	NPC477702
0.8636	High Similarity	NPC475875
0.8633	High Similarity	NPC185307
0.8633	High Similarity	NPC470950
0.8615	High Similarity	NPC17348
0.8613	High Similarity	NPC9068
0.8605	High Similarity	NPC249788
0.8603	High Similarity	NPC25695
0.8603	High Similarity	NPC172818
0.8603	High Similarity	NPC78047
0.8593	High Similarity	NPC185680
0.8593	High Similarity	NPC145722
0.8593	High Similarity	NPC67247
0.8593	High Similarity	NPC256776
0.8582	High Similarity	NPC93610
0.8582	High Similarity	NPC241846

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 NPC227160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	847
0.2-0.3	1753
0.3-0.4	2817
0.4-0.5	1804
0.5-0.6	1062
0.6-0.7	446
0.7-0.8	57
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD3705	Approved
0.8468	Intermediate Similarity	NPD5283	Phase 1
0.8088	Intermediate Similarity	NPD3027	Phase 3
0.8013	Intermediate Similarity	NPD4965	Approved
0.8013	Intermediate Similarity	NPD4967	Phase 2
0.8013	Intermediate Similarity	NPD4966	Approved
0.7939	Intermediate Similarity	NPD1357	Approved
0.7908	Intermediate Similarity	NPD6234	Discontinued
0.7877	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD37	Approved
0.7724	Intermediate Similarity	NPD6674	Discontinued
0.7704	Intermediate Similarity	NPD2981	Phase 2
0.7647	Intermediate Similarity	NPD2982	Phase 2
0.7647	Intermediate Similarity	NPD2983	Phase 2
0.7619	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1375	Discontinued
0.758	Intermediate Similarity	NPD7199	Phase 2
0.7562	Intermediate Similarity	NPD7228	Approved
0.7554	Intermediate Similarity	NPD2861	Phase 2
0.7554	Intermediate Similarity	NPD3018	Phase 2
0.7535	Intermediate Similarity	NPD1613	Approved
0.7535	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7266	Discontinued
0.745	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD5058	Phase 3
0.7394	Intermediate Similarity	NPD5109	Approved
0.7394	Intermediate Similarity	NPD5111	Phase 2
0.7394	Intermediate Similarity	NPD5110	Phase 2
0.7378	Intermediate Similarity	NPD7240	Approved
0.7376	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1091	Approved
0.7365	Intermediate Similarity	NPD4236	Phase 3
0.7365	Intermediate Similarity	NPD4237	Approved
0.7361	Intermediate Similarity	NPD3657	Discovery
0.7329	Intermediate Similarity	NPD4108	Discontinued
0.7328	Intermediate Similarity	NPD228	Approved
0.732	Intermediate Similarity	NPD4210	Discontinued
0.7315	Intermediate Similarity	NPD4110	Phase 3
0.7315	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2977	Approved
0.7308	Intermediate Similarity	NPD2978	Approved
0.7305	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3620	Phase 2
0.7292	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD5327	Phase 3
0.7254	Intermediate Similarity	NPD4908	Phase 1
0.7254	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7157	Approved
0.7231	Intermediate Similarity	NPD2684	Approved
0.7226	Intermediate Similarity	NPD5126	Approved
0.7226	Intermediate Similarity	NPD5125	Phase 3
0.7226	Intermediate Similarity	NPD7028	Phase 2
0.7219	Intermediate Similarity	NPD7124	Phase 2
0.7211	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6331	Phase 2
0.7197	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5494	Approved
0.7176	Intermediate Similarity	NPD3022	Approved
0.7176	Intermediate Similarity	NPD3021	Approved
0.7172	Intermediate Similarity	NPD4060	Phase 1
0.717	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2438	Suspended
0.7162	Intermediate Similarity	NPD2161	Phase 2
0.7153	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5585	Approved
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7843	Approved
0.7143	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD6896	Approved
0.7143	Intermediate Similarity	NPD6895	Approved
0.7134	Intermediate Similarity	NPD3382	Approved
0.7134	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD3384	Approved
0.7134	Intermediate Similarity	NPD3383	Approved
0.7133	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6355	Discontinued
0.7123	Intermediate Similarity	NPD5735	Approved
0.7122	Intermediate Similarity	NPD1610	Phase 2
0.7103	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD17	Approved
0.7097	Intermediate Similarity	NPD1653	Approved
0.7095	Intermediate Similarity	NPD5588	Approved
0.7086	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2979	Phase 3
0.7047	Intermediate Similarity	NPD3539	Phase 1
0.7045	Intermediate Similarity	NPD5451	Approved
0.7044	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5691	Approved
0.7027	Intermediate Similarity	NPD4536	Approved
0.7027	Intermediate Similarity	NPD6111	Discontinued
0.7027	Intermediate Similarity	NPD4538	Approved
0.7027	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1358	Approved
0.7021	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3060	Approved
0.7018	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD3540	Phase 1
0.7	Intermediate Similarity	NPD5763	Approved
0.6985	Remote Similarity	NPD6387	Discontinued
0.6972	Remote Similarity	NPD8651	Approved
0.6972	Remote Similarity	NPD2922	Phase 1
0.6968	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7095	Approved
0.6964	Remote Similarity	NPD7685	Pre-registration
0.6959	Remote Similarity	NPD2492	Phase 1
0.6957	Remote Similarity	NPD1182	Approved
0.695	Remote Similarity	NPD1840	Phase 2
0.695	Remote Similarity	NPD1608	Approved
0.6947	Remote Similarity	NPD3134	Approved
0.6946	Remote Similarity	NPD7074	Phase 3
0.694	Remote Similarity	NPD1137	Approved
0.694	Remote Similarity	NPD1139	Approved
0.6939	Remote Similarity	NPD1558	Phase 1
0.6939	Remote Similarity	NPD4140	Approved
0.6939	Remote Similarity	NPD2238	Phase 2
0.6923	Remote Similarity	NPD5976	Discontinued
0.6918	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1934	Approved
0.6918	Remote Similarity	NPD5718	Phase 2
0.6913	Remote Similarity	NPD7097	Phase 1
0.6908	Remote Similarity	NPD5177	Phase 3
0.6908	Remote Similarity	NPD4162	Approved
0.6906	Remote Similarity	NPD1651	Approved
0.6903	Remote Similarity	NPD4123	Phase 3
0.6901	Remote Similarity	NPD3685	Discontinued
0.6901	Remote Similarity	NPD4359	Approved
0.6889	Remote Similarity	NPD7680	Approved
0.6889	Remote Similarity	NPD1138	Approved
0.6886	Remote Similarity	NPD7054	Approved
0.6879	Remote Similarity	NPD1281	Approved
0.6875	Remote Similarity	NPD8455	Phase 2
0.6871	Remote Similarity	NPD6233	Phase 2
0.6867	Remote Similarity	NPD5960	Phase 3
0.6863	Remote Similarity	NPD4628	Phase 3
0.6861	Remote Similarity	NPD709	Approved
0.6859	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD52	Approved
0.6859	Remote Similarity	NPD7526	Approved
0.6857	Remote Similarity	NPD5846	Approved
0.6857	Remote Similarity	NPD6516	Phase 2
0.6855	Remote Similarity	NPD6385	Approved
0.6855	Remote Similarity	NPD6386	Approved
0.6852	Remote Similarity	NPD5604	Discontinued
0.6846	Remote Similarity	NPD6653	Approved
0.6846	Remote Similarity	NPD6353	Approved
0.6845	Remote Similarity	NPD7472	Approved
0.6842	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1548	Phase 1
0.6835	Remote Similarity	NPD4005	Discontinued
0.6832	Remote Similarity	NPD3817	Phase 2
0.6832	Remote Similarity	NPD2563	Approved
0.6832	Remote Similarity	NPD2560	Approved
0.6829	Remote Similarity	NPD8127	Discontinued
0.6818	Remote Similarity	NPD2677	Approved
0.6812	Remote Similarity	NPD3596	Phase 2
0.6807	Remote Similarity	NPD4481	Phase 3
0.6803	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6798	Discontinued
0.68	Remote Similarity	NPD7296	Approved
0.68	Remote Similarity	NPD7119	Phase 2
0.6798	Remote Similarity	NPD4420	Approved
0.6792	Remote Similarity	NPD4678	Approved
0.6792	Remote Similarity	NPD4675	Approved
0.679	Remote Similarity	NPD3882	Suspended
0.6783	Remote Similarity	NPD4749	Approved
0.6779	Remote Similarity	NPD1933	Approved
0.6776	Remote Similarity	NPD6002	Phase 3
0.6776	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6005	Phase 3
0.6776	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6004	Phase 3
0.6772	Remote Similarity	NPD3686	Approved
0.6772	Remote Similarity	NPD3687	Approved
0.677	Remote Similarity	NPD5772	Approved
0.677	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5773	Approved
0.6767	Remote Similarity	NPD290	Approved
0.6761	Remote Similarity	NPD1611	Approved
0.676	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4624	Approved
0.6759	Remote Similarity	NPD6584	Phase 3
0.6759	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4870	Approved
0.6753	Remote Similarity	NPD7466	Approved
0.6747	Remote Similarity	NPD5242	Approved
0.6744	Remote Similarity	NPD3020	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