NPASS Compound

Structure

CID194938 OpenBabel06191715582D 40 44 0 0 1 0 0 0 0 0999 V2000 4.5983 1.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0934 -0.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9683 -3.0036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4260 0.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2920 -1.3647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2920 0.6353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1580 -0.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0366 0.1325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5600 -1.3647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 1.4067 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 4.3036 0.8126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1506 -2.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4260 -0.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1580 0.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.6636 0.0000 C 0 0 1 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 4.9619 -0.8647 0.0000 C 0 0 2 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 6.6939 -0.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -0.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1356 -1.4281 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 3.1801 -1.1333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2043 -2.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0241 0.6353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6939 0.1353 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 2.9095 -3.7067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8279 -1.3647 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6045 -1.9510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 2 0 0 0 0 3 14 2 0 0 0 0 4 6 1 0 0 0 0 4 15 2 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 21 1 0 0 0 0 10 18 1 0 0 0 0 11 30 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 28 1 0 0 0 0 16 31 1 0 0 0 0 17 10 1 1 0 0 0 17 22 1 0 0 0 0 18 38 1 1 0 0 0 19 23 1 0 0 0 0 19 37 1 1 0 0 0 20 11 1 6 0 0 0 20 24 1 0 0 0 0 20 39 1 0 0 0 0 21 32 2 0 0 0 0 21 37 1 0 0 0 0 22 13 1 1 0 0 0 22 27 1 0 0 0 0 23 14 1 1 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 33 1 1 0 0 0 25 26 1 0 0 0 0 25 34 1 6 0 0 0 26 29 1 0 0 0 0 26 35 1 1 0 0 0 27 40 1 6 0 0 0 28 36 2 0 0 0 0 28 40 1 0 0 0 0 29 38 1 6 0 0 0 29 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.21
Volume:	542.959
LogP:	0.275
LogD:	1.002
LogS:	-2.293
# Rotatable Bonds:	7
TPSA:	172.21
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.184
Synthetic Accessibility Score:	5.127
Fsp3:	0.517
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.334
MDCK Permeability:	3.59668156306725e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.886
20% Bioavailability (F20%):	0.464
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	73.95450592041016%
Volume Distribution (VD):	0.388
Pgp-substrate:	22.64476776123047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.174
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	2.297
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.283
Human Hepatotoxicity (H-HT):	0.938
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.104
Rat Oral Acute Toxicity:	0.658
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.068
Carcinogencity:	0.083
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.89

Download Data

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

Natural Product: NPC194938

Natural Product ID:	NPC194938
*Common Name:**	Ixerisoside A
IUPAC Name:	[(3aR,4R,6aR,8S,9aR,9bR)-3,6,9-trimethylidene-2-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate
Synonyms:
Standard InCHIKey:	GJWZSERDLUJEOD-CLPOWKOCSA-N
Standard InCHI:	InChI=1S/C29H34O11/c1-12-8-19(37-21(32)9-15-4-6-16(31)7-5-15)23-14(3)28(36)40-27(23)22-13(2)18(10-17(12)22)38-29-26(35)25(34)24(33)20(11-30)39-29/h4-7,17-20,22-27,29-31,33-35H,1-3,8-11H2/t17-,18-,19+,20+,22-,23+,24+,25-,26+,27+,29+/m0/s1
SMILES:	C=C1C[C@H]([C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(=C)[C@H](C[C@@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC(=O)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622764
PubChem CID:	10076444
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90113-8]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987049]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17567070]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	seed	n.a.	PMID[21280632]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21648406]
NPO32813	ixeris dentata	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[26341134]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13	Chamaecrista mimosoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13	Chamaecrista mimosoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5855	Scutellaria repens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9352	Senecio peltiferus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO372	Kallstroemia tribuloides	Species	Zygophyllaceae	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	4

Activity Type	# Activity
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	20.3	uM	PMID[529976]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	16.3	uM	PMID[529976]
NPT27	Others	Unspecified		Activity	=	105.5	%	PMID[529976]
NPT27	Others	Unspecified		Activity	=	109.2	%	PMID[529976]

☑ 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 NPC194938 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	329
0.1-0.2	1085
0.2-0.3	2665
0.3-0.4	5532
0.4-0.5	10696
0.5-0.6	10577
0.6-0.7	10085
0.7-0.8	1640
0.8-0.85	69
0.85-0.9	15
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC120728
0.9577	High Similarity	NPC35097
0.9571	High Similarity	NPC473147
0.9021	High Similarity	NPC202391
0.9021	High Similarity	NPC296659
0.8973	High Similarity	NPC96599
0.8912	High Similarity	NPC240592
0.8912	High Similarity	NPC117346
0.8819	High Similarity	NPC186296
0.8792	High Similarity	NPC478235
0.8759	High Similarity	NPC251062
0.8759	High Similarity	NPC184464
0.8725	High Similarity	NPC158546
0.8725	High Similarity	NPC289021
0.8681	High Similarity	NPC7518
0.8681	High Similarity	NPC154262
0.8681	High Similarity	NPC159387
0.8681	High Similarity	NPC137501
0.8618	High Similarity	NPC475484
0.8609	High Similarity	NPC257847
0.8609	High Similarity	NPC229354
0.86	High Similarity	NPC475379
0.8591	High Similarity	NPC161955
0.8591	High Similarity	NPC478236
0.8571	High Similarity	NPC475528
0.8571	High Similarity	NPC281798
0.8562	High Similarity	NPC475378
0.8562	High Similarity	NPC478250
0.8542	High Similarity	NPC31745
0.8542	High Similarity	NPC220936
0.8531	High Similarity	NPC471345
0.8521	High Similarity	NPC169398
0.8516	High Similarity	NPC130489
0.8516	High Similarity	NPC208676
0.8514	High Similarity	NPC474268
0.8514	High Similarity	NPC143246
0.8514	High Similarity	NPC475539
0.8514	High Similarity	NPC119773
0.8503	High Similarity	NPC473281
0.8503	High Similarity	NPC77922
0.8467	Intermediate Similarity	NPC478234
0.8446	Intermediate Similarity	NPC210330
0.844	Intermediate Similarity	NPC478255
0.8421	Intermediate Similarity	NPC194705
0.8417	Intermediate Similarity	NPC45224
0.8417	Intermediate Similarity	NPC471881
0.8417	Intermediate Similarity	NPC156692
0.8417	Intermediate Similarity	NPC173150
0.8417	Intermediate Similarity	NPC35288
0.8417	Intermediate Similarity	NPC471882
0.8389	Intermediate Similarity	NPC473867
0.8389	Intermediate Similarity	NPC212808
0.8387	Intermediate Similarity	NPC187205
0.8387	Intermediate Similarity	NPC49173
0.838	Intermediate Similarity	NPC471095
0.838	Intermediate Similarity	NPC471066
0.8378	Intermediate Similarity	NPC63304
0.8357	Intermediate Similarity	NPC225307
0.8355	Intermediate Similarity	NPC474620
0.8345	Intermediate Similarity	NPC61181
0.8345	Intermediate Similarity	NPC65262
0.8345	Intermediate Similarity	NPC469364
0.8345	Intermediate Similarity	NPC101686
0.8333	Intermediate Similarity	NPC179914
0.8322	Intermediate Similarity	NPC114116
0.8322	Intermediate Similarity	NPC164172
0.8321	Intermediate Similarity	NPC52097
0.8311	Intermediate Similarity	NPC293154
0.8311	Intermediate Similarity	NPC475213
0.8311	Intermediate Similarity	NPC152796
0.831	Intermediate Similarity	NPC254819
0.8299	Intermediate Similarity	NPC46644
0.8291	Intermediate Similarity	NPC145847
0.8288	Intermediate Similarity	NPC49597
0.8288	Intermediate Similarity	NPC220942
0.8286	Intermediate Similarity	NPC288416
0.8286	Intermediate Similarity	NPC103533
0.8276	Intermediate Similarity	NPC470572
0.8267	Intermediate Similarity	NPC320734
0.8248	Intermediate Similarity	NPC11724
0.8247	Intermediate Similarity	NPC245615
0.8247	Intermediate Similarity	NPC115466
0.8247	Intermediate Similarity	NPC299706
0.8247	Intermediate Similarity	NPC61604
0.8243	Intermediate Similarity	NPC296643
0.8239	Intermediate Similarity	NPC109990
0.8239	Intermediate Similarity	NPC469705
0.8239	Intermediate Similarity	NPC17968
0.8239	Intermediate Similarity	NPC470122
0.8219	Intermediate Similarity	NPC469696
0.8212	Intermediate Similarity	NPC473149
0.8207	Intermediate Similarity	NPC123988
0.8182	Intermediate Similarity	NPC219677
0.8182	Intermediate Similarity	NPC46137
0.8182	Intermediate Similarity	NPC235294
0.8175	Intermediate Similarity	NPC476872
0.817	Intermediate Similarity	NPC229882
0.817	Intermediate Similarity	NPC179128
0.817	Intermediate Similarity	NPC116292
0.817	Intermediate Similarity	NPC87630
0.817	Intermediate Similarity	NPC267469
0.817	Intermediate Similarity	NPC158635
0.8169	Intermediate Similarity	NPC469549
0.8165	Intermediate Similarity	NPC138993
0.8163	Intermediate Similarity	NPC62800
0.8163	Intermediate Similarity	NPC171134
0.8163	Intermediate Similarity	NPC321184
0.8163	Intermediate Similarity	NPC321638
0.8163	Intermediate Similarity	NPC328273
0.8163	Intermediate Similarity	NPC324262
0.8158	Intermediate Similarity	NPC189631
0.8156	Intermediate Similarity	NPC106677
0.8153	Intermediate Similarity	NPC104275
0.8153	Intermediate Similarity	NPC4747
0.8151	Intermediate Similarity	NPC472132
0.8146	Intermediate Similarity	NPC208293
0.8143	Intermediate Similarity	NPC126991
0.8143	Intermediate Similarity	NPC83218
0.8143	Intermediate Similarity	NPC123704
0.8141	Intermediate Similarity	NPC38699
0.8138	Intermediate Similarity	NPC471883
0.8125	Intermediate Similarity	NPC473924
0.8121	Intermediate Similarity	NPC148080
0.8121	Intermediate Similarity	NPC469623
0.8113	Intermediate Similarity	NPC293568
0.8113	Intermediate Similarity	NPC117943
0.8113	Intermediate Similarity	NPC477627
0.8102	Intermediate Similarity	NPC469702
0.8102	Intermediate Similarity	NPC282409
0.8099	Intermediate Similarity	NPC158673
0.8095	Intermediate Similarity	NPC100558
0.8095	Intermediate Similarity	NPC302583
0.8095	Intermediate Similarity	NPC310252
0.8095	Intermediate Similarity	NPC84789
0.8089	Intermediate Similarity	NPC478055
0.8089	Intermediate Similarity	NPC163635
0.8085	Intermediate Similarity	NPC471157
0.8085	Intermediate Similarity	NPC252114
0.8077	Intermediate Similarity	NPC478232
0.8069	Intermediate Similarity	NPC254398
0.8069	Intermediate Similarity	NPC28637
0.8067	Intermediate Similarity	NPC88754
0.8067	Intermediate Similarity	NPC204644
0.8067	Intermediate Similarity	NPC242756
0.8067	Intermediate Similarity	NPC263397
0.8067	Intermediate Similarity	NPC40305
0.8067	Intermediate Similarity	NPC302286
0.8067	Intermediate Similarity	NPC237872
0.8067	Intermediate Similarity	NPC116104
0.8065	Intermediate Similarity	NPC203664
0.8063	Intermediate Similarity	NPC476011
0.8058	Intermediate Similarity	NPC471067
0.8056	Intermediate Similarity	NPC138777
0.8056	Intermediate Similarity	NPC246869
0.8056	Intermediate Similarity	NPC476407
0.8056	Intermediate Similarity	NPC225384
0.8052	Intermediate Similarity	NPC162569
0.8052	Intermediate Similarity	NPC69367
0.8052	Intermediate Similarity	NPC12006
0.8052	Intermediate Similarity	NPC35160
0.805	Intermediate Similarity	NPC474936
0.8043	Intermediate Similarity	NPC476445
0.8043	Intermediate Similarity	NPC476448
0.8043	Intermediate Similarity	NPC469548
0.8042	Intermediate Similarity	NPC477294
0.8042	Intermediate Similarity	NPC229784
0.8042	Intermediate Similarity	NPC477293
0.8042	Intermediate Similarity	NPC214246
0.8039	Intermediate Similarity	NPC473138
0.8039	Intermediate Similarity	NPC28776
0.8038	Intermediate Similarity	NPC329997
0.8038	Intermediate Similarity	NPC226759
0.8037	Intermediate Similarity	NPC21956
0.8026	Intermediate Similarity	NPC3982
0.8025	Intermediate Similarity	NPC469459
0.8025	Intermediate Similarity	NPC172920
0.8025	Intermediate Similarity	NPC469396
0.8025	Intermediate Similarity	NPC156624
0.8025	Intermediate Similarity	NPC149002
0.8025	Intermediate Similarity	NPC469419
0.8025	Intermediate Similarity	NPC469458
0.8025	Intermediate Similarity	NPC88176
0.8014	Intermediate Similarity	NPC287597
0.8014	Intermediate Similarity	NPC34293
0.8014	Intermediate Similarity	NPC886
0.8	Intermediate Similarity	NPC232454
0.8	Intermediate Similarity	NPC470907
0.8	Intermediate Similarity	NPC178449
0.8	Intermediate Similarity	NPC140151
0.7987	Intermediate Similarity	NPC76211
0.7987	Intermediate Similarity	NPC469384
0.7987	Intermediate Similarity	NPC478242
0.7986	Intermediate Similarity	NPC469686
0.7975	Intermediate Similarity	NPC10945
0.7975	Intermediate Similarity	NPC228357
0.7974	Intermediate Similarity	NPC470330
0.7974	Intermediate Similarity	NPC18789
0.7973	Intermediate Similarity	NPC260425
0.7973	Intermediate Similarity	NPC308976
0.7972	Intermediate Similarity	NPC232880

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 NPC194938 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	695
0.2-0.3	1654
0.3-0.4	2739
0.4-0.5	2299
0.5-0.6	1160
0.6-0.7	310
0.7-0.8	28
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
0.7919	Intermediate Similarity	NPD7266	Discontinued
0.7784	Intermediate Similarity	NPD7685	Pre-registration
0.7651	Intermediate Similarity	NPD7228	Approved
0.7625	Intermediate Similarity	NPD8455	Phase 2
0.7602	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6234	Discontinued
0.7531	Intermediate Similarity	NPD4966	Approved
0.7531	Intermediate Similarity	NPD4967	Phase 2
0.7531	Intermediate Similarity	NPD4965	Approved
0.7517	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3764	Approved
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6190	Approved
0.7453	Intermediate Similarity	NPD37	Approved
0.7451	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6004	Phase 3
0.7451	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6005	Phase 3
0.7451	Intermediate Similarity	NPD6002	Phase 3
0.7419	Intermediate Similarity	NPD4628	Phase 3
0.7389	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6355	Discontinued
0.7349	Intermediate Similarity	NPD7199	Phase 2
0.7337	Intermediate Similarity	NPD3818	Discontinued
0.7333	Intermediate Similarity	NPD6663	Approved
0.7303	Intermediate Similarity	NPD6653	Approved
0.7283	Intermediate Similarity	NPD8312	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7267	Intermediate Similarity	NPD7240	Approved
0.7267	Intermediate Similarity	NPD6559	Discontinued
0.723	Intermediate Similarity	NPD5647	Approved
0.7203	Intermediate Similarity	NPD9545	Approved
0.7181	Intermediate Similarity	NPD5736	Approved
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD230	Phase 1
0.7123	Intermediate Similarity	NPD1091	Approved
0.7117	Intermediate Similarity	NPD4380	Phase 2
0.7108	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1653	Approved
0.7093	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7075	Discontinued
0.7052	Intermediate Similarity	NPD7074	Phase 3
0.7035	Intermediate Similarity	NPD7799	Discontinued
0.7032	Intermediate Similarity	NPD7097	Phase 1
0.7029	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7054	Approved
0.6981	Remote Similarity	NPD8166	Discontinued
0.6954	Remote Similarity	NPD7472	Approved
0.6951	Remote Similarity	NPD7458	Discontinued
0.695	Remote Similarity	NPD969	Suspended
0.6941	Remote Similarity	NPD8127	Discontinued
0.6933	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6362	Approved
0.6914	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5762	Approved
0.6899	Remote Similarity	NPD5763	Approved
0.6886	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD7251	Discontinued
0.6871	Remote Similarity	NPD5126	Approved
0.6871	Remote Similarity	NPD6273	Approved
0.6871	Remote Similarity	NPD5125	Phase 3
0.6865	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5958	Discontinued
0.6842	Remote Similarity	NPD2861	Phase 2
0.6836	Remote Similarity	NPD7808	Phase 3
0.6835	Remote Similarity	NPD6685	Approved
0.6821	Remote Similarity	NPD3094	Phase 2
0.6818	Remote Similarity	NPD6798	Discontinued
0.6818	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6797	Phase 2
0.6818	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7680	Approved
0.6807	Remote Similarity	NPD7028	Phase 2
0.6806	Remote Similarity	NPD2629	Approved
0.6772	Remote Similarity	NPD7033	Discontinued
0.6772	Remote Similarity	NPD2799	Discontinued
0.677	Remote Similarity	NPD4110	Phase 3
0.677	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3750	Approved
0.676	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5402	Approved
0.6739	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5765	Approved
0.6733	Remote Similarity	NPD1608	Approved
0.673	Remote Similarity	NPD7137	Phase 2
0.673	Remote Similarity	NPD2438	Suspended
0.673	Remote Similarity	NPD2935	Discontinued
0.6727	Remote Similarity	NPD5403	Approved
0.6726	Remote Similarity	NPD6801	Discontinued
0.6718	Remote Similarity	NPD7930	Approved
0.6713	Remote Similarity	NPD6912	Phase 3
0.6708	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2534	Approved
0.6707	Remote Similarity	NPD2532	Approved
0.6707	Remote Similarity	NPD2533	Approved
0.6703	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5058	Phase 3
0.6686	Remote Similarity	NPD7819	Suspended
0.6685	Remote Similarity	NPD8150	Discontinued
0.6685	Remote Similarity	NPD8434	Phase 2
0.6684	Remote Similarity	NPD8320	Phase 1
0.6684	Remote Similarity	NPD8319	Approved
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3705	Approved
0.6667	Remote Similarity	NPD3092	Approved
0.6667	Remote Similarity	NPD3400	Discontinued
0.6649	Remote Similarity	NPD7999	Approved
0.6647	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6799	Approved
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2424	Discontinued
0.6646	Remote Similarity	NPD1549	Phase 2
0.6645	Remote Similarity	NPD3027	Phase 3
0.6644	Remote Similarity	NPD3019	Approved
0.6644	Remote Similarity	NPD7157	Approved
0.6644	Remote Similarity	NPD2932	Approved
0.6643	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7435	Discontinued
0.663	Remote Similarity	NPD7296	Approved
0.6627	Remote Similarity	NPD1934	Approved
0.6624	Remote Similarity	NPD4140	Approved
0.6624	Remote Similarity	NPD4060	Phase 1
0.6623	Remote Similarity	NPD1481	Phase 2
0.6623	Remote Similarity	NPD9269	Phase 2
0.661	Remote Similarity	NPD5844	Phase 1
0.661	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7768	Phase 2
0.6608	Remote Similarity	NPD3882	Suspended
0.6607	Remote Similarity	NPD6599	Discontinued
0.6606	Remote Similarity	NPD5401	Approved
0.6605	Remote Similarity	NPD6674	Discontinued
0.6601	Remote Similarity	NPD2797	Approved
0.6599	Remote Similarity	NPD9493	Approved
0.6591	Remote Similarity	NPD7473	Discontinued
0.6588	Remote Similarity	NPD1465	Phase 2
0.6588	Remote Similarity	NPD5761	Phase 2
0.6588	Remote Similarity	NPD5760	Phase 2
0.6588	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7236	Approved
0.6584	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5735	Approved
0.6575	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2067	Discontinued
0.657	Remote Similarity	NPD3749	Approved
0.6568	Remote Similarity	NPD7411	Suspended
0.6562	Remote Similarity	NPD1510	Phase 2
0.6559	Remote Similarity	NPD6534	Approved
0.6559	Remote Similarity	NPD6535	Approved
0.6556	Remote Similarity	NPD1535	Discovery
0.6554	Remote Similarity	NPD3751	Discontinued
0.6552	Remote Similarity	NPD7843	Approved
0.6548	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3455	Phase 2
0.6543	Remote Similarity	NPD7700	Phase 2
0.6543	Remote Similarity	NPD7699	Phase 2
0.6543	Remote Similarity	NPD4534	Discontinued
0.6538	Remote Similarity	NPD7095	Approved
0.6536	Remote Similarity	NPD1876	Approved
0.6536	Remote Similarity	NPD1283	Approved
0.6534	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6166	Phase 2
0.6534	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD17	Approved
0.6522	Remote Similarity	NPD1551	Phase 2
0.6519	Remote Similarity	NPD2979	Phase 3
0.6519	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1613	Approved
0.6514	Remote Similarity	NPD6232	Discontinued
0.6514	Remote Similarity	NPD7315	Approved
0.6514	Remote Similarity	NPD3787	Discontinued
0.651	Remote Similarity	NPD1894	Discontinued
0.651	Remote Similarity	NPD3091	Approved
0.6503	Remote Similarity	NPD1652	Phase 2
0.65	Remote Similarity	NPD6647	Phase 2
0.6497	Remote Similarity	NPD3268	Approved
0.6494	Remote Similarity	NPD1164	Approved
0.6494	Remote Similarity	NPD5494	Approved
0.6492	Remote Similarity	NPD6823	Phase 2
0.6488	Remote Similarity	NPD7239	Suspended
0.6478	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD5124	Phase 1
0.6474	Remote Similarity	NPD6779	Approved
0.6474	Remote Similarity	NPD6782	Approved
0.6474	Remote Similarity	NPD6778	Approved
0.6474	Remote Similarity	NPD6777	Approved
0.6474	Remote Similarity	NPD6781	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