NPASS Compound

Structure

CID114120 OpenBabel06191715472D 55 62 0 0 1 0 0 0 0 0999 V2000 6.1667 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0934 0.6746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3233 1.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 -3.4087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 -1.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5031 3.0882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -1.4945 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 -3.5143 2.1444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2125 -4.3868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1667 1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6007 1.7377 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2614 -4.6958 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4962 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4817 -4.0267 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4947 1.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3052 0.1554 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2738 -3.0485 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6188 3.1389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9557 -5.0559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7917 2.3255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0535 -5.6740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4328 -4.3357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1638 2.2268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3917 -0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5002 1.5882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2188 0.5621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6773 -2.7395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2007 -0.8392 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 6.9099 2.1746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5086 2.9836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 45 1 0 0 0 0 2 46 1 0 0 0 0 3 4 2 0 0 0 0 3 14 1 0 0 0 0 4 20 1 0 0 0 0 5 14 2 0 0 0 0 5 23 1 0 0 0 0 6 15 2 0 0 0 0 6 21 1 0 0 0 0 7 16 2 0 0 0 0 7 22 1 0 0 0 0 8 17 1 0 0 0 0 8 47 1 0 0 0 0 9 18 1 0 0 0 0 9 48 1 0 0 0 0 10 19 1 0 0 0 0 10 49 1 0 0 0 0 11 36 1 0 0 0 0 11 50 1 0 0 0 0 12 36 1 0 0 0 0 12 51 1 0 0 0 0 13 52 1 0 0 0 0 13 53 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 30 1 0 0 0 0 17 25 1 0 0 0 0 17 30 2 0 0 0 0 18 26 1 0 0 0 0 18 37 1 1 0 0 0 19 27 1 0 0 0 0 19 38 1 6 0 0 0 20 23 2 0 0 0 0 20 52 1 0 0 0 0 21 22 2 0 0 0 0 21 45 1 0 0 0 0 22 46 1 0 0 0 0 23 53 1 0 0 0 0 24 25 2 0 0 0 0 25 32 1 0 0 0 0 26 28 1 0 0 0 0 26 39 1 6 0 0 0 27 29 1 0 0 0 0 27 40 1 6 0 0 0 28 33 1 0 0 0 0 28 41 1 1 0 0 0 29 34 1 0 0 0 0 29 42 1 1 0 0 0 30 54 1 0 0 0 0 31 35 1 0 0 0 0 31 36 1 6 0 0 0 31 55 1 0 0 0 0 32 43 2 0 0 0 0 32 47 1 0 0 0 0 33 48 1 0 0 0 0 33 50 1 6 0 0 0 34 49 1 0 0 0 0 34 55 1 6 0 0 0 35 51 1 0 0 0 0 35 54 1 1 0 0 0 36 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	776.22
Volume:	706.046
LogP:	0.786
LogD:	0.415
LogS:	-5.504
# Rotatable Bonds:	10
TPSA:	260.21
# H-Bond Aceptor:	19
# H-Bond Donor:	7
# Rings:	8
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.118
Synthetic Accessibility Score:	5.484
Fsp3:	0.528
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.164
MDCK Permeability:	2.4222590582212433e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.709
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.8

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	74.78562927246094%
Volume Distribution (VD):	0.519
Pgp-substrate:	4.601806640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.213
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.033

ADMET: Excretion

Clearance (CL):	0.977
Half-life (T1/2):	0.483

ADMET: Toxicity

hERG Blockers:	0.613
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.731
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.173
Carcinogencity:	0.872
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC114120

Natural Product ID:	NPC114120
*Common Name:**	Ciliatoside A
IUPAC Name:	9-(1,3-benzodioxol-5-yl)-4-[(2S,3R,4R)-4-hydroxy-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-4-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxolan-2-yl]oxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one
Synonyms:
Standard InCHIKey:	WTNBRCRYRLAZFO-DSUIHCPPSA-N
Standard InCHI:	InChI=1S/C36H40O19/c1-45-21-6-15-16(7-22(21)46-2)30(17-8-47-32(43)25(17)24(15)14-3-4-20-23(5-14)53-13-52-20)54-35-31(55-34-29(42)27(40)19(38)10-49-34)36(44,12-51-35)11-50-33-28(41)26(39)18(37)9-48-33/h3-7,18-19,26-29,31,33-35,37-42,44H,8-13H2,1-2H3/t18-,19+,26+,27+,28-,29-,31+,33+,34+,35+,36-/m1/s1
SMILES:	COc1cc2c(cc1OC)c(c1COC(=O)c1c2c1ccc2c(c1)OCO2)O[C@H]1[C@@H]([C@@](CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)(CO1)O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497767
PubChem CID:	10462924
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO16896	Justicia ciliata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425143]
NPO16896	Justicia ciliata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087610]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16896	Justicia ciliata	Species	Acanthaceae	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	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	46.7	%	PMID[491521]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	37.9	%	PMID[491521]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	22.0	%	PMID[491521]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	18.7	%	PMID[491521]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	11.9	%	PMID[491521]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	27100.0	nM	PMID[491521]

☑ 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 NPC114120 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	399
0.1-0.2	1569
0.2-0.3	3117
0.3-0.4	7047
0.4-0.5	9924
0.5-0.6	6806
0.6-0.7	7616
0.7-0.8	5672
0.8-0.85	490
0.85-0.9	37
0.9-0.95	13
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC167045
0.9882	High Similarity	NPC313063
0.9882	High Similarity	NPC286301
0.9821	High Similarity	NPC275690
0.9821	High Similarity	NPC161609
0.9762	High Similarity	NPC35266
0.9583	High Similarity	NPC184624
0.9524	High Similarity	NPC114550
0.9524	High Similarity	NPC312006
0.9524	High Similarity	NPC471922
0.9524	High Similarity	NPC471920
0.9524	High Similarity	NPC129930
0.9524	High Similarity	NPC292712
0.9524	High Similarity	NPC471921
0.9524	High Similarity	NPC473697
0.9524	High Similarity	NPC20114
0.9524	High Similarity	NPC474075
0.9345	High Similarity	NPC473531
0.9345	High Similarity	NPC475453
0.9286	High Similarity	NPC471923
0.9186	High Similarity	NPC193377
0.9123	High Similarity	NPC52598
0.8882	High Similarity	NPC198796
0.8882	High Similarity	NPC116838
0.8882	High Similarity	NPC22130
0.8869	High Similarity	NPC19600
0.8837	High Similarity	NPC306475
0.881	High Similarity	NPC239113
0.881	High Similarity	NPC115123
0.88	High Similarity	NPC316539
0.8779	High Similarity	NPC222531
0.8764	High Similarity	NPC53680
0.8764	High Similarity	NPC208797
0.8743	High Similarity	NPC476358
0.8736	High Similarity	NPC117911
0.8728	High Similarity	NPC474042
0.8728	High Similarity	NPC174734
0.8715	High Similarity	NPC476203
0.8713	High Similarity	NPC15212
0.8701	High Similarity	NPC67629
0.8701	High Similarity	NPC79736
0.8686	High Similarity	NPC179240
0.8655	High Similarity	NPC78944
0.8652	High Similarity	NPC267549
0.8636	High Similarity	NPC38438
0.8634	High Similarity	NPC264302
0.8619	High Similarity	NPC241847
0.8613	High Similarity	NPC17432
0.8605	High Similarity	NPC100465
0.8605	High Similarity	NPC152424
0.8605	High Similarity	NPC115624
0.8596	High Similarity	NPC196771
0.8596	High Similarity	NPC297574
0.8596	High Similarity	NPC474043
0.858	High Similarity	NPC54179
0.8571	High Similarity	NPC185498
0.8571	High Similarity	NPC79322
0.8547	High Similarity	NPC96593
0.8547	High Similarity	NPC47191
0.8538	High Similarity	NPC143328
0.8525	High Similarity	NPC205721
0.8516	High Similarity	NPC87583
0.8514	High Similarity	NPC83049
0.8514	High Similarity	NPC118162
0.8514	High Similarity	NPC320471
0.8508	High Similarity	NPC129533
0.8508	High Similarity	NPC123259
0.8506	High Similarity	NPC25889
0.85	High Similarity	NPC80956
0.8497	Intermediate Similarity	NPC288149
0.8495	Intermediate Similarity	NPC314687
0.8492	Intermediate Similarity	NPC66820
0.8492	Intermediate Similarity	NPC170018
0.8492	Intermediate Similarity	NPC92403
0.8492	Intermediate Similarity	NPC76112
0.8492	Intermediate Similarity	NPC472723
0.8492	Intermediate Similarity	NPC469397
0.8483	Intermediate Similarity	NPC199357
0.848	Intermediate Similarity	NPC473900
0.8475	Intermediate Similarity	NPC313304
0.8475	Intermediate Similarity	NPC135370
0.847	Intermediate Similarity	NPC105591
0.8466	Intermediate Similarity	NPC298847
0.8462	Intermediate Similarity	NPC474442
0.8453	Intermediate Similarity	NPC164047
0.8453	Intermediate Similarity	NPC475161
0.8453	Intermediate Similarity	NPC470453
0.8453	Intermediate Similarity	NPC477860
0.8453	Intermediate Similarity	NPC188217
0.8453	Intermediate Similarity	NPC470452
0.8453	Intermediate Similarity	NPC470448
0.8453	Intermediate Similarity	NPC469371
0.8452	Intermediate Similarity	NPC475722
0.8448	Intermediate Similarity	NPC22324
0.8448	Intermediate Similarity	NPC246024
0.8444	Intermediate Similarity	NPC241196
0.8436	Intermediate Similarity	NPC146803
0.8436	Intermediate Similarity	NPC63105
0.8424	Intermediate Similarity	NPC269046
0.8421	Intermediate Similarity	NPC186316
0.8421	Intermediate Similarity	NPC234730
0.8418	Intermediate Similarity	NPC658
0.8418	Intermediate Similarity	NPC473202
0.8418	Intermediate Similarity	NPC197708
0.8415	Intermediate Similarity	NPC475352
0.8415	Intermediate Similarity	NPC475220
0.8415	Intermediate Similarity	NPC473686
0.8415	Intermediate Similarity	NPC229817
0.8415	Intermediate Similarity	NPC221140
0.8407	Intermediate Similarity	NPC35924
0.8407	Intermediate Similarity	NPC199172
0.8407	Intermediate Similarity	NPC473883
0.84	Intermediate Similarity	NPC116759
0.84	Intermediate Similarity	NPC14294
0.84	Intermediate Similarity	NPC121290
0.8398	Intermediate Similarity	NPC245059
0.8398	Intermediate Similarity	NPC84494
0.8389	Intermediate Similarity	NPC312630
0.8389	Intermediate Similarity	NPC289876
0.8389	Intermediate Similarity	NPC324220
0.8382	Intermediate Similarity	NPC173726
0.8382	Intermediate Similarity	NPC478269
0.8382	Intermediate Similarity	NPC241600
0.838	Intermediate Similarity	NPC46640
0.838	Intermediate Similarity	NPC203751
0.838	Intermediate Similarity	NPC166674
0.838	Intermediate Similarity	NPC219600
0.838	Intermediate Similarity	NPC263119
0.838	Intermediate Similarity	NPC473550
0.838	Intermediate Similarity	NPC34436
0.8378	Intermediate Similarity	NPC93065
0.8378	Intermediate Similarity	NPC31208
0.8378	Intermediate Similarity	NPC472724
0.8378	Intermediate Similarity	NPC472721
0.8378	Intermediate Similarity	NPC472720
0.8378	Intermediate Similarity	NPC469652
0.8378	Intermediate Similarity	NPC314672
0.8378	Intermediate Similarity	NPC160543
0.8372	Intermediate Similarity	NPC109765
0.837	Intermediate Similarity	NPC237202
0.837	Intermediate Similarity	NPC65489
0.8361	Intermediate Similarity	NPC231254
0.836	Intermediate Similarity	NPC174140
0.8352	Intermediate Similarity	NPC85316
0.8352	Intermediate Similarity	NPC178281
0.8352	Intermediate Similarity	NPC99216
0.8352	Intermediate Similarity	NPC197357
0.8352	Intermediate Similarity	NPC8940
0.8343	Intermediate Similarity	NPC158635
0.8343	Intermediate Similarity	NPC229882
0.8333	Intermediate Similarity	NPC119910
0.8333	Intermediate Similarity	NPC469354
0.8333	Intermediate Similarity	NPC181464
0.8333	Intermediate Similarity	NPC48474
0.8333	Intermediate Similarity	NPC473630
0.8333	Intermediate Similarity	NPC470667
0.8333	Intermediate Similarity	NPC475244
0.8333	Intermediate Similarity	NPC186800
0.8324	Intermediate Similarity	NPC119094
0.8324	Intermediate Similarity	NPC223534
0.8324	Intermediate Similarity	NPC173872
0.8324	Intermediate Similarity	NPC142291
0.8324	Intermediate Similarity	NPC473618
0.8324	Intermediate Similarity	NPC207584
0.8324	Intermediate Similarity	NPC290289
0.8324	Intermediate Similarity	NPC102851
0.8324	Intermediate Similarity	NPC202495
0.8324	Intermediate Similarity	NPC158214
0.8324	Intermediate Similarity	NPC5786
0.8324	Intermediate Similarity	NPC7839
0.8324	Intermediate Similarity	NPC19947
0.8324	Intermediate Similarity	NPC240200
0.8315	Intermediate Similarity	NPC111490
0.8315	Intermediate Similarity	NPC261623
0.8315	Intermediate Similarity	NPC88557
0.8306	Intermediate Similarity	NPC473205
0.8306	Intermediate Similarity	NPC473717
0.8306	Intermediate Similarity	NPC473631
0.8306	Intermediate Similarity	NPC473776
0.8306	Intermediate Similarity	NPC293227
0.8306	Intermediate Similarity	NPC475662
0.8298	Intermediate Similarity	NPC316274
0.8298	Intermediate Similarity	NPC470193
0.8298	Intermediate Similarity	NPC470195
0.8298	Intermediate Similarity	NPC470197
0.8298	Intermediate Similarity	NPC282474
0.8298	Intermediate Similarity	NPC470198
0.8298	Intermediate Similarity	NPC470196
0.8298	Intermediate Similarity	NPC470200
0.8298	Intermediate Similarity	NPC470194
0.8297	Intermediate Similarity	NPC58538
0.8297	Intermediate Similarity	NPC277710
0.8297	Intermediate Similarity	NPC212290
0.8297	Intermediate Similarity	NPC153578
0.8297	Intermediate Similarity	NPC114257
0.8297	Intermediate Similarity	NPC472726
0.8297	Intermediate Similarity	NPC472725
0.8297	Intermediate Similarity	NPC299149
0.8287	Intermediate Similarity	NPC46958
0.8287	Intermediate Similarity	NPC102053

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 NPC114120 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	871
0.2-0.3	1714
0.3-0.4	2630
0.4-0.5	2097
0.5-0.6	1005
0.6-0.7	382
0.7-0.8	103
0.8-0.85	7
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7228	Approved
0.8492	Intermediate Similarity	NPD8312	Approved
0.8492	Intermediate Similarity	NPD8313	Approved
0.8483	Intermediate Similarity	NPD7240	Approved
0.8471	Intermediate Similarity	NPD8455	Phase 2
0.8315	Intermediate Similarity	NPD5844	Phase 1
0.8266	Intermediate Similarity	NPD4966	Approved
0.8266	Intermediate Similarity	NPD4967	Phase 2
0.8266	Intermediate Similarity	NPD4965	Approved
0.8171	Intermediate Similarity	NPD6234	Discontinued
0.8162	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD37	Approved
0.8079	Intermediate Similarity	NPD7199	Phase 2
0.8077	Intermediate Similarity	NPD6559	Discontinued
0.8075	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD7074	Phase 3
0.8066	Intermediate Similarity	NPD7472	Approved
0.8033	Intermediate Similarity	NPD7808	Phase 3
0.8031	Intermediate Similarity	NPD7680	Approved
0.8011	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6232	Discontinued
0.7929	Intermediate Similarity	NPD7783	Phase 2
0.7929	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7889	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD7251	Discontinued
0.7857	Intermediate Similarity	NPD3818	Discontinued
0.7853	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7828	Intermediate Similarity	NPD8151	Discontinued
0.7826	Intermediate Similarity	NPD6797	Phase 2
0.7826	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6674	Discontinued
0.7784	Intermediate Similarity	NPD7685	Pre-registration
0.7747	Intermediate Similarity	NPD6166	Phase 2
0.7747	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6959	Discontinued
0.764	Intermediate Similarity	NPD7819	Suspended
0.764	Intermediate Similarity	NPD1465	Phase 2
0.7624	Intermediate Similarity	NPD5494	Approved
0.76	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8127	Discontinued
0.7576	Intermediate Similarity	NPD7435	Discontinued
0.7514	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7487	Intermediate Similarity	NPD7698	Approved
0.7486	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD7871	Phase 2
0.745	Intermediate Similarity	NPD7870	Phase 2
0.7446	Intermediate Similarity	NPD3787	Discontinued
0.7444	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7874	Approved
0.7437	Intermediate Similarity	NPD6823	Phase 2
0.7426	Intermediate Similarity	NPD7701	Phase 2
0.7424	Intermediate Similarity	NPD6781	Approved
0.7424	Intermediate Similarity	NPD6777	Approved
0.7424	Intermediate Similarity	NPD6779	Approved
0.7424	Intermediate Similarity	NPD6776	Approved
0.7424	Intermediate Similarity	NPD6780	Approved
0.7424	Intermediate Similarity	NPD6778	Approved
0.7424	Intermediate Similarity	NPD6782	Approved
0.7416	Intermediate Similarity	NPD7458	Discontinued
0.7413	Intermediate Similarity	NPD7999	Approved
0.7403	Intermediate Similarity	NPD3817	Phase 2
0.7396	Intermediate Similarity	NPD8150	Discontinued
0.7389	Intermediate Similarity	NPD1934	Approved
0.7384	Intermediate Similarity	NPD7266	Discontinued
0.738	Intermediate Similarity	NPD3751	Discontinued
0.7363	Intermediate Similarity	NPD7768	Phase 2
0.7363	Intermediate Similarity	NPD8320	Phase 1
0.7363	Intermediate Similarity	NPD8319	Approved
0.7356	Intermediate Similarity	NPD4628	Phase 3
0.7348	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7699	Phase 2
0.7323	Intermediate Similarity	NPD7700	Phase 2
0.7322	Intermediate Similarity	NPD7075	Discontinued
0.7318	Intermediate Similarity	NPD3226	Approved
0.7308	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD8434	Phase 2
0.7292	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1653	Approved
0.7258	Intermediate Similarity	NPD7229	Phase 3
0.7257	Intermediate Similarity	NPD7003	Approved
0.7247	Intermediate Similarity	NPD6273	Approved
0.7238	Intermediate Similarity	NPD7411	Suspended
0.7233	Intermediate Similarity	NPD7801	Approved
0.7228	Intermediate Similarity	NPD3749	Approved
0.7212	Intermediate Similarity	NPD7930	Approved
0.7209	Intermediate Similarity	NPD7097	Phase 1
0.72	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2533	Approved
0.7191	Intermediate Similarity	NPD2532	Approved
0.7191	Intermediate Similarity	NPD2534	Approved
0.7182	Intermediate Similarity	NPD4380	Phase 2
0.7174	Intermediate Similarity	NPD3882	Suspended
0.7172	Intermediate Similarity	NPD6534	Approved
0.7172	Intermediate Similarity	NPD6535	Approved
0.717	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2801	Approved
0.715	Intermediate Similarity	NPD4420	Approved
0.712	Intermediate Similarity	NPD5402	Approved
0.7104	Intermediate Similarity	NPD6801	Discontinued
0.7095	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1933	Approved
0.7088	Intermediate Similarity	NPD7028	Phase 2
0.7062	Intermediate Similarity	NPD3750	Approved
0.7029	Intermediate Similarity	NPD2438	Suspended
0.7023	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3764	Approved
0.7018	Intermediate Similarity	NPD6798	Discontinued
0.7016	Intermediate Similarity	NPD7177	Discontinued
0.701	Intermediate Similarity	NPD5006	Approved
0.701	Intermediate Similarity	NPD5005	Approved
0.7006	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD919	Approved
0.6995	Remote Similarity	NPD6599	Discontinued
0.6994	Remote Similarity	NPD6355	Discontinued
0.6989	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3748	Approved
0.6966	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7039	Approved
0.6959	Remote Similarity	NPD7038	Approved
0.695	Remote Similarity	NPD6212	Phase 3
0.695	Remote Similarity	NPD6213	Phase 3
0.695	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3926	Phase 2
0.6946	Remote Similarity	NPD8285	Discontinued
0.6932	Remote Similarity	NPD5408	Approved
0.6932	Remote Similarity	NPD5405	Approved
0.6932	Remote Similarity	NPD2935	Discontinued
0.6932	Remote Similarity	NPD5404	Approved
0.6932	Remote Similarity	NPD5406	Approved
0.6927	Remote Similarity	NPD6190	Approved
0.6927	Remote Similarity	NPD7799	Discontinued
0.6923	Remote Similarity	NPD5403	Approved
0.6906	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5401	Approved
0.6897	Remote Similarity	NPD447	Suspended
0.6893	Remote Similarity	NPD5763	Approved
0.6893	Remote Similarity	NPD5762	Approved
0.6879	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD7583	Approved
0.6875	Remote Similarity	NPD2799	Discontinued
0.6872	Remote Similarity	NPD8166	Discontinued
0.6872	Remote Similarity	NPD4110	Phase 3
0.6872	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1283	Approved
0.686	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2424	Discontinued
0.6851	Remote Similarity	NPD1511	Approved
0.6851	Remote Similarity	NPD6799	Approved
0.6849	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD8059	Phase 3
0.6842	Remote Similarity	NPD7585	Approved
0.6842	Remote Similarity	NPD1247	Approved
0.6839	Remote Similarity	NPD4060	Phase 1
0.6839	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2979	Phase 3
0.6839	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1613	Approved
0.6821	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7985	Registered
0.6821	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7296	Approved
0.6813	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5711	Approved
0.6806	Remote Similarity	NPD5710	Approved
0.6798	Remote Similarity	NPD6005	Phase 3
0.6798	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6004	Phase 3
0.6798	Remote Similarity	NPD6002	Phase 3
0.6798	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5058	Phase 3
0.6791	Remote Similarity	NPD5760	Phase 2
0.6791	Remote Similarity	NPD5761	Phase 2
0.6786	Remote Similarity	NPD3705	Approved
0.678	Remote Similarity	NPD4308	Phase 3
0.6778	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1512	Approved
0.6774	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4625	Phase 3
0.6763	Remote Similarity	NPD7095	Approved
0.6758	Remote Similarity	NPD7390	Discontinued
0.6751	Remote Similarity	NPD7549	Discontinued
0.6739	Remote Similarity	NPD920	Approved
0.6724	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD2313	Discontinued
0.6718	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7584	Approved
0.6705	Remote Similarity	NPD6832	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data