NPASS Compound

Structure

CID311057 OpenBabel06191716122D 27 32 0 0 1 0 0 0 0 0999 V2000 4.8592 1.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7252 1.7188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7252 -0.2812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3887 -2.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4105 -0.6176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1301 0.7188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8592 0.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8887 -1.2757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9105 -1.4836 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5913 1.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5913 0.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9932 -0.2812 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8060 -2.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0796 0.1255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7195 -2.8849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5423 1.5278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5423 -0.0902 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 1.9400 -2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 11 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 11 2 0 0 0 0 5 17 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 22 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 9 25 1 0 0 0 0 10 24 1 0 0 0 0 10 26 1 0 0 0 0 12 27 1 0 0 0 0 13 7 1 1 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 8 1 1 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 11 1 6 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.11
Volume:	348.85
LogP:	3.532
LogD:	3.124
LogS:	-5.801
# Rotatable Bonds:	3
TPSA:	64.61
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.823
Synthetic Accessibility Score:	3.842
Fsp3:	0.4
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:	-5.001
MDCK Permeability:	6.431099609471858e-05
Pgp-inhibitor:	0.179
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.119
Plasma Protein Binding (PPB):	96.4640121459961%
Volume Distribution (VD):	0.698
Pgp-substrate:	1.7400529384613037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.778
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.956
CYP2C19-substrate:	0.248
CYP2C9-inhibitor:	0.6
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.986
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.962
CYP3A4-substrate:	0.301

ADMET: Excretion

Clearance (CL):	17.117
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.475
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.855
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.74
Skin Sensitization:	0.902
Carcinogencity:	0.894
Eye Corrosion:	0.004
Eye Irritation:	0.556
Respiratory Toxicity:	0.606

Download Data

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

Natural Product: NPC311057

Natural Product ID:	NPC311057
*Common Name:**	Sesamolin
IUPAC Name:	5-[[(3S,3aR,6R,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]oxy]-1,3-benzodioxole
Synonyms:	Sesamolin
Standard InCHIKey:	ZZMNWJVJUKMZJY-AFHBHXEDSA-N
Standard InCHI:	InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
SMILES:	c1cc2c(cc1[C@@H]1[C@H]3CO[C@@H]([C@H]3CO1)Oc1ccc3c(c1)OCO3)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2059646
PubChem CID:	101746
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)83306-8]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	seed	n.a.	PMID[11540412]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932128]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24024688]
NPO3302	Fusarium avenaceum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798960]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3905	Medinilla magnifica	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8339	Lithothamnion corallioides	Species	Hapalidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1585	Onobrychis bobrovii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3302	Fusarium avenaceum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7266	Goupia glabra	Species	Goupiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2501	Trifolium strepens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5937	Garrya laurifolia	Species	Garryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2703	Petteria ramentacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4858	Helipterum gnaphaloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5021	Podospora curvicolla	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO823	Senecio cathcartensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8703	Monopteryx uaucu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3905	Medinilla magnifica	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4221	Fusarium sacchari	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7963	Excoecaria acerifolia	Species	Euphorbiaceae	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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	Inhibition	<	30.0	%	PMID[460146]
NPT71	Cell Line	HEK293	Homo sapiens	Inhibition	=	11.6	%	PMID[460147]
NPT2	Others	Unspecified		IC50	=	200000.0	nM	PMID[460146]
NPT671	Individual Protein	Acidic alpha-glucosidase	Rattus norvegicus	Inhibition	<	30.0	%	PMID[460146]

☑ 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 NPC311057 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	584
0.1-0.2	1709
0.2-0.3	5072
0.3-0.4	12405
0.4-0.5	6147
0.5-0.6	6570
0.6-0.7	7821
0.7-0.8	2002
0.8-0.85	263
0.85-0.9	104
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9407	High Similarity	NPC189474
0.9348	High Similarity	NPC312199
0.9333	High Similarity	NPC31530
0.9328	High Similarity	NPC129687
0.9328	High Similarity	NPC33611
0.9328	High Similarity	NPC171928
0.9328	High Similarity	NPC158526
0.9328	High Similarity	NPC16830
0.9328	High Similarity	NPC100223
0.9281	High Similarity	NPC80326
0.9281	High Similarity	NPC472562
0.9265	High Similarity	NPC148893
0.9265	High Similarity	NPC49235
0.9265	High Similarity	NPC25333
0.9259	High Similarity	NPC266848
0.9259	High Similarity	NPC136750
0.922	High Similarity	NPC205316
0.9209	High Similarity	NPC58137
0.9209	High Similarity	NPC300798
0.9185	High Similarity	NPC72046
0.9185	High Similarity	NPC261812
0.9185	High Similarity	NPC65183
0.9143	High Similarity	NPC174522
0.913	High Similarity	NPC469981
0.9111	High Similarity	NPC192255
0.9111	High Similarity	NPC82111
0.9111	High Similarity	NPC227160
0.9065	High Similarity	NPC113550
0.9037	High Similarity	NPC233224
0.9037	High Similarity	NPC271208
0.9	High Similarity	NPC226547
0.9	High Similarity	NPC46591
0.9	High Similarity	NPC56091
0.8993	High Similarity	NPC185908
0.8993	High Similarity	NPC101807
0.8966	High Similarity	NPC240521
0.8951	High Similarity	NPC474749
0.8951	High Similarity	NPC42716
0.8951	High Similarity	NPC11422
0.8951	High Similarity	NPC178014
0.8944	High Similarity	NPC255566
0.8944	High Similarity	NPC298317
0.8921	High Similarity	NPC121651
0.8913	High Similarity	NPC47181
0.8905	High Similarity	NPC7744
0.8904	High Similarity	NPC238140
0.8889	High Similarity	NPC226862
0.8889	High Similarity	NPC82862
0.8889	High Similarity	NPC165128
0.8889	High Similarity	NPC222127
0.8889	High Similarity	NPC158471
0.8889	High Similarity	NPC57119
0.8873	High Similarity	NPC474295
0.8857	High Similarity	NPC283949
0.8849	High Similarity	NPC18576
0.8849	High Similarity	NPC474139
0.8819	High Similarity	NPC180953
0.8815	High Similarity	NPC473093
0.8815	High Similarity	NPC473092
0.8815	High Similarity	NPC158737
0.8815	High Similarity	NPC8050
0.8811	High Similarity	NPC185071
0.8811	High Similarity	NPC474808
0.8811	High Similarity	NPC12728
0.8786	High Similarity	NPC11453
0.8777	High Similarity	NPC170779
0.8777	High Similarity	NPC474478
0.8777	High Similarity	NPC90083
0.8767	High Similarity	NPC301961
0.8767	High Similarity	NPC166584
0.8767	High Similarity	NPC71726
0.8759	High Similarity	NPC226540
0.8759	High Similarity	NPC162193
0.875	High Similarity	NPC477701
0.875	High Similarity	NPC166884
0.875	High Similarity	NPC54321
0.875	High Similarity	NPC281864
0.875	High Similarity	NPC328682
0.875	High Similarity	NPC141569
0.8741	High Similarity	NPC112571
0.8741	High Similarity	NPC285725
0.8741	High Similarity	NPC50683
0.8732	High Similarity	NPC216434
0.8732	High Similarity	NPC103448
0.8732	High Similarity	NPC177868
0.8714	High Similarity	NPC150534
0.8707	High Similarity	NPC51328
0.8707	High Similarity	NPC286235
0.8707	High Similarity	NPC55158
0.8705	High Similarity	NPC1474
0.8705	High Similarity	NPC196937
0.8671	High Similarity	NPC471908
0.8662	High Similarity	NPC193666
0.8662	High Similarity	NPC123526
0.8662	High Similarity	NPC88640
0.8662	High Similarity	NPC9068
0.8652	High Similarity	NPC78047
0.8652	High Similarity	NPC25695
0.8652	High Similarity	NPC172818
0.8652	High Similarity	NPC143895
0.8639	High Similarity	NPC130449
0.8639	High Similarity	NPC248132
0.8623	High Similarity	NPC470624
0.8623	High Similarity	NPC134764
0.8623	High Similarity	NPC171550
0.8623	High Similarity	NPC237169
0.8621	High Similarity	NPC177644
0.8621	High Similarity	NPC191158
0.8611	High Similarity	NPC287124
0.8611	High Similarity	NPC246947
0.8603	High Similarity	NPC186845
0.8603	High Similarity	NPC88297
0.8603	High Similarity	NPC9891
0.8593	High Similarity	NPC34902
0.8593	High Similarity	NPC18449
0.8593	High Similarity	NPC121783
0.8582	High Similarity	NPC236522
0.8581	High Similarity	NPC35877
0.8581	High Similarity	NPC55715
0.8581	High Similarity	NPC95392
0.8571	High Similarity	NPC39657
0.8562	High Similarity	NPC307466
0.8562	High Similarity	NPC469586
0.8561	High Similarity	NPC473412
0.8561	High Similarity	NPC469698
0.8543	High Similarity	NPC159922
0.8531	High Similarity	NPC292487
0.8531	High Similarity	NPC156376
0.8521	High Similarity	NPC197166
0.8521	High Similarity	NPC32189
0.8514	High Similarity	NPC270751
0.85	High Similarity	NPC147616
0.85	High Similarity	NPC259742
0.85	High Similarity	NPC104077
0.85	High Similarity	NPC219671
0.8493	Intermediate Similarity	NPC179521
0.8493	Intermediate Similarity	NPC218841
0.8493	Intermediate Similarity	NPC92693
0.8483	Intermediate Similarity	NPC176586
0.8483	Intermediate Similarity	NPC210354
0.8472	Intermediate Similarity	NPC160283
0.8472	Intermediate Similarity	NPC27495
0.8472	Intermediate Similarity	NPC284464
0.8472	Intermediate Similarity	NPC254759
0.8462	Intermediate Similarity	NPC196420
0.8462	Intermediate Similarity	NPC474039
0.8451	Intermediate Similarity	NPC135777
0.8451	Intermediate Similarity	NPC142547
0.8451	Intermediate Similarity	NPC99572
0.8451	Intermediate Similarity	NPC126409
0.8446	Intermediate Similarity	NPC116019
0.8444	Intermediate Similarity	NPC261661
0.8435	Intermediate Similarity	NPC22150
0.8435	Intermediate Similarity	NPC38041
0.8435	Intermediate Similarity	NPC279298
0.8435	Intermediate Similarity	NPC477702
0.8425	Intermediate Similarity	NPC265154
0.8414	Intermediate Similarity	NPC469661
0.8403	Intermediate Similarity	NPC30951
0.8403	Intermediate Similarity	NPC292882
0.8403	Intermediate Similarity	NPC6369
0.8389	Intermediate Similarity	NPC175976
0.838	Intermediate Similarity	NPC145722
0.838	Intermediate Similarity	NPC185680
0.838	Intermediate Similarity	NPC256776
0.8378	Intermediate Similarity	NPC276753
0.8378	Intermediate Similarity	NPC33832
0.8378	Intermediate Similarity	NPC193779
0.8378	Intermediate Similarity	NPC212890
0.8378	Intermediate Similarity	NPC112861
0.8378	Intermediate Similarity	NPC205796
0.837	Intermediate Similarity	NPC216929
0.837	Intermediate Similarity	NPC65933
0.837	Intermediate Similarity	NPC126935
0.837	Intermediate Similarity	NPC312713
0.837	Intermediate Similarity	NPC301641
0.837	Intermediate Similarity	NPC172676
0.837	Intermediate Similarity	NPC80241
0.837	Intermediate Similarity	NPC57268
0.8367	Intermediate Similarity	NPC50696
0.8367	Intermediate Similarity	NPC473045
0.8367	Intermediate Similarity	NPC187774
0.8367	Intermediate Similarity	NPC472712
0.8367	Intermediate Similarity	NPC172171
0.8367	Intermediate Similarity	NPC25292
0.8367	Intermediate Similarity	NPC239254
0.8367	Intermediate Similarity	NPC473046
0.8367	Intermediate Similarity	NPC118385
0.8367	Intermediate Similarity	NPC472713
0.8366	Intermediate Similarity	NPC164152
0.8357	Intermediate Similarity	NPC63574
0.8356	Intermediate Similarity	NPC40237
0.8356	Intermediate Similarity	NPC151423
0.8356	Intermediate Similarity	NPC302506
0.8356	Intermediate Similarity	NPC189115
0.8356	Intermediate Similarity	NPC107161
0.8345	Intermediate Similarity	NPC31707
0.8345	Intermediate Similarity	NPC210674
0.8344	Intermediate Similarity	NPC474975
0.8333	Intermediate Similarity	NPC213711

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 NPC311057 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	443
0.1-0.2	867
0.2-0.3	2116
0.3-0.4	2871
0.4-0.5	1562
0.5-0.6	890
0.6-0.7	364
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8102	Intermediate Similarity	NPD3705	Approved
0.7902	Intermediate Similarity	NPD3027	Phase 3
0.7848	Intermediate Similarity	NPD4965	Approved
0.7848	Intermediate Similarity	NPD4966	Approved
0.7848	Intermediate Similarity	NPD4967	Phase 2
0.775	Intermediate Similarity	NPD6234	Discontinued
0.774	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1613	Approved
0.7704	Intermediate Similarity	NPD5283	Phase 1
0.7658	Intermediate Similarity	NPD37	Approved
0.7654	Intermediate Similarity	NPD7199	Phase 2
0.7628	Intermediate Similarity	NPD1653	Approved
0.7586	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD3383	Approved
0.7547	Intermediate Similarity	NPD3384	Approved
0.7547	Intermediate Similarity	NPD3382	Approved
0.7535	Intermediate Similarity	NPD2981	Phase 2
0.753	Intermediate Similarity	NPD7228	Approved
0.7517	Intermediate Similarity	NPD2861	Phase 2
0.7517	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5494	Approved
0.7483	Intermediate Similarity	NPD2982	Phase 2
0.7483	Intermediate Similarity	NPD2983	Phase 2
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6674	Discontinued
0.7425	Intermediate Similarity	NPD3818	Discontinued
0.7397	Intermediate Similarity	NPD3018	Phase 2
0.7358	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7240	Approved
0.7347	Intermediate Similarity	NPD4908	Phase 1
0.7343	Intermediate Similarity	NPD1610	Phase 2
0.7343	Intermediate Similarity	NPD1091	Approved
0.7278	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1357	Approved
0.7248	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1375	Discontinued
0.7143	Intermediate Similarity	NPD3454	Phase 3
0.7135	Intermediate Similarity	NPD7074	Phase 3
0.7134	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5058	Phase 3
0.7089	Intermediate Similarity	NPD7124	Phase 2
0.7076	Intermediate Similarity	NPD7054	Approved
0.7063	Intermediate Similarity	NPD1548	Phase 1
0.7048	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7472	Approved
0.7012	Intermediate Similarity	NPD1934	Approved
0.6987	Remote Similarity	NPD7266	Discontinued
0.6981	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5844	Phase 1
0.6975	Remote Similarity	NPD4210	Discontinued
0.697	Remote Similarity	NPD2801	Approved
0.6962	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4110	Phase 3
0.6957	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3817	Phase 2
0.6923	Remote Similarity	NPD3539	Phase 1
0.6914	Remote Similarity	NPD7808	Phase 3
0.6908	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6111	Discontinued
0.6897	Remote Similarity	NPD6797	Phase 2
0.6892	Remote Similarity	NPD4749	Approved
0.6892	Remote Similarity	NPD5327	Phase 3
0.689	Remote Similarity	NPD4678	Approved
0.689	Remote Similarity	NPD4675	Approved
0.6887	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3882	Suspended
0.6886	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7680	Approved
0.6879	Remote Similarity	NPD3540	Phase 1
0.6875	Remote Similarity	NPD5536	Phase 2
0.6867	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4108	Discontinued
0.6859	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5588	Approved
0.6859	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7251	Discontinued
0.6857	Remote Similarity	NPD6559	Discontinued
0.6855	Remote Similarity	NPD7466	Approved
0.6855	Remote Similarity	NPD6331	Phase 2
0.6855	Remote Similarity	NPD3892	Phase 2
0.6853	Remote Similarity	NPD7157	Approved
0.6842	Remote Similarity	NPD4625	Phase 3
0.6835	Remote Similarity	NPD2684	Approved
0.6824	Remote Similarity	NPD1247	Approved
0.6818	Remote Similarity	NPD7549	Discontinued
0.6818	Remote Similarity	NPD4060	Phase 1
0.6815	Remote Similarity	NPD2161	Phase 2
0.6798	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5111	Phase 2
0.6797	Remote Similarity	NPD5110	Phase 2
0.6797	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5109	Approved
0.6792	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4237	Approved
0.6792	Remote Similarity	NPD4236	Phase 3
0.6784	Remote Similarity	NPD3787	Discontinued
0.6781	Remote Similarity	NPD5585	Approved
0.6774	Remote Similarity	NPD3657	Discovery
0.6774	Remote Similarity	NPD5735	Approved
0.6774	Remote Similarity	NPD6355	Discontinued
0.6766	Remote Similarity	NPD2978	Approved
0.6766	Remote Similarity	NPD8455	Phase 2
0.6766	Remote Similarity	NPD2977	Approved
0.6761	Remote Similarity	NPD7843	Approved
0.6761	Remote Similarity	NPD5535	Approved
0.6757	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6233	Phase 2
0.675	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3926	Phase 2
0.6735	Remote Similarity	NPD17	Approved
0.6727	Remote Similarity	NPD4005	Discontinued
0.6712	Remote Similarity	NPD1182	Approved
0.6711	Remote Similarity	NPD1840	Phase 2
0.671	Remote Similarity	NPD3620	Phase 2
0.671	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2796	Approved
0.6706	Remote Similarity	NPD919	Approved
0.6705	Remote Similarity	NPD6166	Phase 2
0.6705	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD968	Approved
0.669	Remote Similarity	NPD228	Approved
0.6688	Remote Similarity	NPD4536	Approved
0.6688	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4538	Approved
0.6687	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD5677	Discontinued
0.6647	Remote Similarity	NPD5242	Approved
0.6646	Remote Similarity	NPD3748	Approved
0.6646	Remote Similarity	NPD5960	Phase 3
0.6646	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1611	Approved
0.663	Remote Similarity	NPD6841	Approved
0.663	Remote Similarity	NPD6843	Phase 3
0.663	Remote Similarity	NPD6842	Approved
0.6627	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5402	Approved
0.6626	Remote Similarity	NPD1511	Approved
0.6626	Remote Similarity	NPD4357	Discontinued
0.6623	Remote Similarity	NPD8651	Approved
0.6623	Remote Similarity	NPD7095	Approved
0.6622	Remote Similarity	NPD5846	Approved
0.6622	Remote Similarity	NPD5125	Phase 3
0.6622	Remote Similarity	NPD5126	Approved
0.6622	Remote Similarity	NPD6516	Phase 2
0.6621	Remote Similarity	NPD6671	Approved
0.6606	Remote Similarity	NPD5976	Discontinued
0.6604	Remote Similarity	NPD2438	Suspended
0.6603	Remote Similarity	NPD4140	Approved
0.6603	Remote Similarity	NPD1558	Phase 1
0.66	Remote Similarity	NPD1608	Approved
0.6591	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7229	Phase 3
0.6585	Remote Similarity	NPD4123	Phase 3
0.6585	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1652	Phase 2
0.6584	Remote Similarity	NPD4162	Approved
0.6582	Remote Similarity	NPD7119	Phase 2
0.6582	Remote Similarity	NPD6895	Approved
0.6582	Remote Similarity	NPD6896	Approved
0.6582	Remote Similarity	NPD7097	Phase 1
0.6577	Remote Similarity	NPD3496	Discontinued
0.6573	Remote Similarity	NPD7685	Pre-registration
0.6561	Remote Similarity	NPD5124	Phase 1
0.6561	Remote Similarity	NPD1933	Approved
0.6561	Remote Similarity	NPD5005	Approved
0.6561	Remote Similarity	NPD5006	Approved
0.6561	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4359	Approved
0.6556	Remote Similarity	NPD3685	Discontinued
0.6549	Remote Similarity	NPD3022	Approved
0.6549	Remote Similarity	NPD3021	Approved
0.6545	Remote Similarity	NPD1512	Approved
0.6545	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7526	Approved
0.6545	Remote Similarity	NPD52	Approved
0.6543	Remote Similarity	NPD4628	Phase 3
0.6538	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD3751	Discontinued
0.6533	Remote Similarity	NPD422	Phase 1
0.6532	Remote Similarity	NPD8127	Discontinued
0.6529	Remote Similarity	NPD2563	Approved
0.6529	Remote Similarity	NPD5353	Approved
0.6529	Remote Similarity	NPD2560	Approved
0.6524	Remote Similarity	NPD5297	Approved
0.6524	Remote Similarity	NPD6799	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