NPASS Compound

Structure

CID35266 OpenBabel06191715362D 46 52 0 0 1 0 0 0 0 0999 V2000 -0.8090 6.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1309 0.6096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2418 2.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2226 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9260 4.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1928 3.2435 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3871 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9360 2.5743 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7281 1.5962 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0570 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5322 1.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7770 1.2872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0316 -0.7700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4007 4.2216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8870 2.8833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4712 0.9271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5104 1.6266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 -1.9456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 6.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 5.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1255 0.5051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0339 1.9563 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 5.3382 4.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3382 3.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 38 1 0 0 0 0 2 39 1 0 0 0 0 3 4 2 0 0 0 0 3 13 1 0 0 0 0 4 18 1 0 0 0 0 5 13 2 0 0 0 0 5 21 1 0 0 0 0 6 14 2 0 0 0 0 6 19 1 0 0 0 0 7 15 2 0 0 0 0 7 20 1 0 0 0 0 8 16 1 0 0 0 0 8 40 1 0 0 0 0 9 17 1 0 0 0 0 9 41 1 0 0 0 0 10 31 1 0 0 0 0 10 32 1 0 0 0 0 11 31 1 0 0 0 0 11 42 1 0 0 0 0 12 43 1 0 0 0 0 12 44 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 26 1 0 0 0 0 16 23 1 0 0 0 0 16 26 2 0 0 0 0 17 24 1 0 0 0 0 17 33 1 6 0 0 0 18 21 2 0 0 0 0 18 43 1 0 0 0 0 19 20 2 0 0 0 0 19 38 1 0 0 0 0 20 39 1 0 0 0 0 21 44 1 0 0 0 0 22 23 2 0 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 24 34 1 6 0 0 0 25 29 1 0 0 0 0 25 35 1 1 0 0 0 26 45 1 0 0 0 0 27 30 1 0 0 0 0 27 31 1 1 0 0 0 27 46 1 0 0 0 0 28 36 2 0 0 0 0 28 40 1 0 0 0 0 29 41 1 0 0 0 0 29 46 1 6 0 0 0 30 42 1 0 0 0 0 30 45 1 6 0 0 0 31 37 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	644.17
Volume:	592.962
LogP:	1.251
LogD:	1.154
LogS:	-4.854
# Rotatable Bonds:	8
TPSA:	201.29
# H-Bond Aceptor:	15
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	4.856
Fsp3:	0.452
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.106
MDCK Permeability:	1.6857857190188952e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	79.93333435058594%
Volume Distribution (VD):	0.552
Pgp-substrate:	2.9203076362609863%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.218
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.197
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.534
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	3.514
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.231
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.84
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.085
Carcinogencity:	0.912
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC35266

Natural Product ID:	NPC35266
*Common Name:**	4-O-Alpha-L-Arabinopyranosyl-(1'''->2'')-Beta-D-Apiofuranosyldiphyllin
IUPAC Name:	9-(1,3-benzodioxol-5-yl)-4-[(2S,3R,4R)-4-hydroxy-4-(hydroxymethyl)-3-[(2R,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxolan-2-yl]oxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one
Synonyms:
Standard InCHIKey:	HBUCXSOGVZJQHH-RMTLSDLPSA-N
Standard InCHI:	InChI=1S/C31H32O15/c1-38-19-6-14-15(7-20(19)39-2)26(16-8-40-28(36)23(16)22(14)13-3-4-18-21(5-13)44-12-43-18)45-30-27(31(37,10-32)11-42-30)46-29-25(35)24(34)17(33)9-41-29/h3-7,17,24-25,27,29-30,32-35,37H,8-12H2,1-2H3/t17-,24-,25+,27+,29-,30+,31-/m1/s1
SMILES:	OC[C@@]1(O)CO[C@H]([C@@H]1O[C@H]1OC[C@H]([C@H]([C@@H]1O)O)O)Oc1c2COC(=O)c2c(c2c1cc(OC)c(c2)OC)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508105
PubChem CID:	10484309
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
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908984]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3734816]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988600]
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]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	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
ED50	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	ED50	=	3.9	ug ml-1	PMID[482730]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	6.7	ug ml-1	PMID[482730]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.1	ug ml-1	PMID[482730]

☑ 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 NPC35266 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	379
0.1-0.2	1525
0.2-0.3	3071
0.3-0.4	7132
0.4-0.5	10216
0.5-0.6	5803
0.6-0.7	6773
0.7-0.8	7160
0.8-0.85	561
0.85-0.9	52
0.9-0.95	11
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9817	High Similarity	NPC184624
0.9762	High Similarity	NPC114120
0.9762	High Similarity	NPC167045
0.9756	High Similarity	NPC129930
0.9756	High Similarity	NPC471920
0.9756	High Similarity	NPC114550
0.9756	High Similarity	NPC292712
0.9756	High Similarity	NPC471921
0.9756	High Similarity	NPC312006
0.9756	High Similarity	NPC20114
0.9756	High Similarity	NPC474075
0.9756	High Similarity	NPC471922
0.9647	High Similarity	NPC286301
0.9647	High Similarity	NPC313063
0.9583	High Similarity	NPC161609
0.9583	High Similarity	NPC275690
0.9455	High Similarity	NPC475453
0.9455	High Similarity	NPC473531
0.9405	High Similarity	NPC193377
0.9394	High Similarity	NPC471923
0.9286	High Similarity	NPC473697
0.9112	High Similarity	NPC52598
0.9096	High Similarity	NPC116838
0.9096	High Similarity	NPC22130
0.9096	High Similarity	NPC198796
0.9085	High Similarity	NPC19600
0.9024	High Similarity	NPC239113
0.9024	High Similarity	NPC115123
0.8988	High Similarity	NPC222531
0.8941	High Similarity	NPC117911
0.8935	High Similarity	NPC174734
0.8935	High Similarity	NPC474042
0.8922	High Similarity	NPC15212
0.8895	High Similarity	NPC316539
0.8862	High Similarity	NPC78944
0.881	High Similarity	NPC100465
0.881	High Similarity	NPC152424
0.881	High Similarity	NPC115624
0.8802	High Similarity	NPC474043
0.8793	High Similarity	NPC67629
0.8793	High Similarity	NPC79736
0.8793	High Similarity	NPC196771
0.8788	High Similarity	NPC54179
0.8772	High Similarity	NPC79322
0.875	High Similarity	NPC53680
0.875	High Similarity	NPC96593
0.875	High Similarity	NPC208797
0.8743	High Similarity	NPC267549
0.8743	High Similarity	NPC143328
0.8713	High Similarity	NPC118162
0.8713	High Similarity	NPC320471
0.8713	High Similarity	NPC83049
0.8706	High Similarity	NPC17432
0.8698	High Similarity	NPC288149
0.8683	High Similarity	NPC473900
0.8678	High Similarity	NPC199357
0.8671	High Similarity	NPC135370
0.8667	High Similarity	NPC474442
0.8659	High Similarity	NPC475722
0.8647	High Similarity	NPC22324
0.8636	High Similarity	NPC47191
0.8629	High Similarity	NPC146803
0.8626	High Similarity	NPC476358
0.8623	High Similarity	NPC234730
0.8623	High Similarity	NPC186316
0.8621	High Similarity	NPC38438
0.8613	High Similarity	NPC473202
0.8611	High Similarity	NPC205721
0.8605	High Similarity	NPC306475
0.8596	High Similarity	NPC116759
0.8596	High Similarity	NPC14294
0.858	High Similarity	NPC469397
0.8571	High Similarity	NPC109765
0.8556	High Similarity	NPC105591
0.8555	High Similarity	NPC185498
0.8555	High Similarity	NPC298847
0.8547	High Similarity	NPC178281
0.8545	High Similarity	NPC229882
0.8545	High Similarity	NPC158635
0.8539	High Similarity	NPC188217
0.8537	High Similarity	NPC181464
0.8529	High Similarity	NPC119910
0.8521	High Similarity	NPC202495
0.8521	High Similarity	NPC19947
0.8521	High Similarity	NPC207584
0.8506	High Similarity	NPC88557
0.85	High Similarity	NPC241847
0.8492	Intermediate Similarity	NPC476203
0.8485	Intermediate Similarity	NPC127827
0.8485	Intermediate Similarity	NPC24193
0.8483	Intermediate Similarity	NPC212290
0.848	Intermediate Similarity	NPC191352
0.848	Intermediate Similarity	NPC258322
0.8475	Intermediate Similarity	NPC475054
0.8475	Intermediate Similarity	NPC312630
0.8475	Intermediate Similarity	NPC475233
0.8475	Intermediate Similarity	NPC297574
0.8475	Intermediate Similarity	NPC324220
0.8471	Intermediate Similarity	NPC241600
0.8471	Intermediate Similarity	NPC173726
0.8471	Intermediate Similarity	NPC478269
0.8471	Intermediate Similarity	NPC125713
0.8462	Intermediate Similarity	NPC32373
0.8462	Intermediate Similarity	NPC228357
0.8462	Intermediate Similarity	NPC237946
0.8457	Intermediate Similarity	NPC298778
0.8457	Intermediate Similarity	NPC313304
0.8457	Intermediate Similarity	NPC179240
0.8448	Intermediate Similarity	NPC311912
0.8443	Intermediate Similarity	NPC118332
0.8436	Intermediate Similarity	NPC475161
0.8436	Intermediate Similarity	NPC477860
0.843	Intermediate Similarity	NPC56735
0.843	Intermediate Similarity	NPC278329
0.843	Intermediate Similarity	NPC146837
0.843	Intermediate Similarity	NPC61594
0.8421	Intermediate Similarity	NPC150943
0.8421	Intermediate Similarity	NPC65784
0.8421	Intermediate Similarity	NPC91634
0.8421	Intermediate Similarity	NPC474770
0.8421	Intermediate Similarity	NPC268718
0.8418	Intermediate Similarity	NPC470667
0.8418	Intermediate Similarity	NPC469438
0.8418	Intermediate Similarity	NPC199533
0.8418	Intermediate Similarity	NPC63105
0.8418	Intermediate Similarity	NPC186800
0.8418	Intermediate Similarity	NPC68381
0.8418	Intermediate Similarity	NPC470454
0.8415	Intermediate Similarity	NPC264302
0.8412	Intermediate Similarity	NPC133984
0.8412	Intermediate Similarity	NPC226759
0.8409	Intermediate Similarity	NPC148185
0.84	Intermediate Similarity	NPC191653
0.8393	Intermediate Similarity	NPC299706
0.8393	Intermediate Similarity	NPC115466
0.8393	Intermediate Similarity	NPC61604
0.8393	Intermediate Similarity	NPC245615
0.8393	Intermediate Similarity	NPC137813
0.8389	Intermediate Similarity	NPC473883
0.8382	Intermediate Similarity	NPC25889
0.8382	Intermediate Similarity	NPC121290
0.8382	Intermediate Similarity	NPC147596
0.838	Intermediate Similarity	NPC80956
0.838	Intermediate Similarity	NPC114257
0.838	Intermediate Similarity	NPC245059
0.838	Intermediate Similarity	NPC277710
0.838	Intermediate Similarity	NPC299149
0.838	Intermediate Similarity	NPC153578
0.838	Intermediate Similarity	NPC84494
0.8373	Intermediate Similarity	NPC111785
0.8372	Intermediate Similarity	NPC319749
0.8372	Intermediate Similarity	NPC478267
0.8372	Intermediate Similarity	NPC216916
0.8371	Intermediate Similarity	NPC473713
0.8371	Intermediate Similarity	NPC472723
0.8362	Intermediate Similarity	NPC477881
0.8362	Intermediate Similarity	NPC166674
0.8362	Intermediate Similarity	NPC34436
0.8362	Intermediate Similarity	NPC98776
0.8362	Intermediate Similarity	NPC85368
0.8362	Intermediate Similarity	NPC263119
0.8362	Intermediate Similarity	NPC46640
0.8362	Intermediate Similarity	NPC219600
0.8362	Intermediate Similarity	NPC203751
0.8361	Intermediate Similarity	NPC314672
0.8353	Intermediate Similarity	NPC163635
0.8353	Intermediate Similarity	NPC261090
0.8353	Intermediate Similarity	NPC11411
0.8353	Intermediate Similarity	NPC478055
0.8352	Intermediate Similarity	NPC475360
0.8352	Intermediate Similarity	NPC477572
0.8352	Intermediate Similarity	NPC477571
0.8352	Intermediate Similarity	NPC477573
0.8343	Intermediate Similarity	NPC185103
0.8343	Intermediate Similarity	NPC472662
0.8343	Intermediate Similarity	NPC472663
0.8333	Intermediate Similarity	NPC36130
0.8333	Intermediate Similarity	NPC470452
0.8333	Intermediate Similarity	NPC302610
0.8333	Intermediate Similarity	NPC470453
0.8333	Intermediate Similarity	NPC99216
0.8333	Intermediate Similarity	NPC134905
0.8333	Intermediate Similarity	NPC470448
0.8333	Intermediate Similarity	NPC164047
0.8324	Intermediate Similarity	NPC477882
0.8324	Intermediate Similarity	NPC216752
0.8324	Intermediate Similarity	NPC241196
0.8324	Intermediate Similarity	NPC249070
0.8324	Intermediate Similarity	NPC33298
0.8324	Intermediate Similarity	NPC280778
0.8324	Intermediate Similarity	NPC477880
0.8324	Intermediate Similarity	NPC260300
0.8324	Intermediate Similarity	NPC101116
0.8324	Intermediate Similarity	NPC212099
0.8324	Intermediate Similarity	NPC285108
0.8315	Intermediate Similarity	NPC474345
0.8315	Intermediate Similarity	NPC469354
0.8315	Intermediate Similarity	NPC169645
0.8315	Intermediate Similarity	NPC84482
0.8315	Intermediate Similarity	NPC475244

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 NPC35266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	852
0.2-0.3	1648
0.3-0.4	2597
0.4-0.5	2100
0.5-0.6	1042
0.6-0.7	445
0.7-0.8	124
0.8-0.85	19
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8555	High Similarity	NPD7228	Approved
0.8506	High Similarity	NPD5844	Phase 1
0.8462	Intermediate Similarity	NPD4965	Approved
0.8462	Intermediate Similarity	NPD4967	Phase 2
0.8462	Intermediate Similarity	NPD4966	Approved
0.8363	Intermediate Similarity	NPD6234	Discontinued
0.8362	Intermediate Similarity	NPD7240	Approved
0.8284	Intermediate Similarity	NPD37	Approved
0.8268	Intermediate Similarity	NPD8313	Approved
0.8268	Intermediate Similarity	NPD8312	Approved
0.8266	Intermediate Similarity	NPD7199	Phase 2
0.8258	Intermediate Similarity	NPD6559	Discontinued
0.8235	Intermediate Similarity	NPD8455	Phase 2
0.8142	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD6232	Discontinued
0.8079	Intermediate Similarity	NPD7473	Discontinued
0.8077	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD7074	Phase 3
0.8035	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD6674	Discontinued
0.7989	Intermediate Similarity	NPD7054	Approved
0.7944	Intermediate Similarity	NPD7472	Approved
0.7917	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7680	Approved
0.7912	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7685	Pre-registration
0.7817	Intermediate Similarity	NPD7783	Phase 2
0.7817	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7251	Discontinued
0.7722	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6166	Phase 2
0.7714	Intermediate Similarity	NPD1465	Phase 2
0.7714	Intermediate Similarity	NPD7819	Suspended
0.7708	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6797	Phase 2
0.7697	Intermediate Similarity	NPD5494	Approved
0.7692	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6959	Discontinued
0.7654	Intermediate Similarity	NPD8127	Discontinued
0.7641	Intermediate Similarity	NPD7435	Discontinued
0.7626	Intermediate Similarity	NPD8151	Discontinued
0.7614	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3817	Phase 2
0.7557	Intermediate Similarity	NPD1934	Approved
0.7529	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD6823	Phase 2
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7486	Intermediate Similarity	NPD3226	Approved
0.7486	Intermediate Similarity	NPD7458	Discontinued
0.7486	Intermediate Similarity	NPD7075	Discontinued
0.7475	Intermediate Similarity	NPD7999	Approved
0.7456	Intermediate Similarity	NPD2346	Discontinued
0.7456	Intermediate Similarity	NPD7266	Discontinued
0.7447	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD3751	Discontinued
0.743	Intermediate Similarity	NPD7768	Phase 2
0.7429	Intermediate Similarity	NPD1653	Approved
0.7424	Intermediate Similarity	NPD7871	Phase 2
0.7424	Intermediate Similarity	NPD7870	Phase 2
0.7418	Intermediate Similarity	NPD7229	Phase 3
0.7414	Intermediate Similarity	NPD6273	Approved
0.7413	Intermediate Similarity	NPD7874	Approved
0.7413	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7411	Suspended
0.7389	Intermediate Similarity	NPD3749	Approved
0.7374	Intermediate Similarity	NPD7697	Approved
0.7374	Intermediate Similarity	NPD7698	Approved
0.7374	Intermediate Similarity	NPD7696	Phase 3
0.7374	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8150	Discontinued
0.7368	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2533	Approved
0.7356	Intermediate Similarity	NPD2532	Approved
0.7356	Intermediate Similarity	NPD2534	Approved
0.7345	Intermediate Similarity	NPD4380	Phase 2
0.7333	Intermediate Similarity	NPD3882	Suspended
0.7326	Intermediate Similarity	NPD7003	Approved
0.7318	Intermediate Similarity	NPD2801	Approved
0.7313	Intermediate Similarity	NPD7701	Phase 2
0.7296	Intermediate Similarity	NPD4420	Approved
0.7278	Intermediate Similarity	NPD5402	Approved
0.7278	Intermediate Similarity	NPD7097	Phase 1
0.7277	Intermediate Similarity	NPD8434	Phase 2
0.7268	Intermediate Similarity	NPD7930	Approved
0.7263	Intermediate Similarity	NPD6801	Discontinued
0.7262	Intermediate Similarity	NPD1933	Approved
0.7257	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8320	Phase 1
0.725	Intermediate Similarity	NPD8319	Approved
0.7247	Intermediate Similarity	NPD7028	Phase 2
0.7243	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6535	Approved
0.7231	Intermediate Similarity	NPD6534	Approved
0.7225	Intermediate Similarity	NPD3750	Approved
0.7208	Intermediate Similarity	NPD7699	Phase 2
0.7208	Intermediate Similarity	NPD7700	Phase 2
0.7206	Intermediate Similarity	NPD7801	Approved
0.7193	Intermediate Similarity	NPD2438	Suspended
0.7186	Intermediate Similarity	NPD6798	Discontinued
0.7186	Intermediate Similarity	NPD3764	Approved
0.7168	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7177	Discontinued
0.716	Intermediate Similarity	NPD6355	Discontinued
0.7158	Intermediate Similarity	NPD919	Approved
0.7151	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6599	Discontinued
0.715	Intermediate Similarity	NPD5006	Approved
0.715	Intermediate Similarity	NPD5005	Approved
0.7143	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3748	Approved
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7039	Approved
0.7105	Intermediate Similarity	NPD7038	Approved
0.7097	Intermediate Similarity	NPD3926	Phase 2
0.7093	Intermediate Similarity	NPD2935	Discontinued
0.7093	Intermediate Similarity	NPD5406	Approved
0.7093	Intermediate Similarity	NPD5405	Approved
0.7093	Intermediate Similarity	NPD5404	Approved
0.7093	Intermediate Similarity	NPD5408	Approved
0.7086	Intermediate Similarity	NPD6190	Approved
0.7079	Intermediate Similarity	NPD5403	Approved
0.7062	Intermediate Similarity	NPD5401	Approved
0.7062	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD447	Suspended
0.7052	Intermediate Similarity	NPD5763	Approved
0.7052	Intermediate Similarity	NPD5762	Approved
0.7041	Intermediate Similarity	NPD6233	Phase 2
0.7035	Intermediate Similarity	NPD2799	Discontinued
0.703	Intermediate Similarity	NPD1283	Approved
0.7029	Intermediate Similarity	NPD4110	Phase 3
0.7029	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2424	Discontinued
0.701	Intermediate Similarity	NPD7583	Approved
0.7006	Intermediate Similarity	NPD1511	Approved
0.7006	Intermediate Similarity	NPD6799	Approved
0.7005	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6212	Phase 3
0.7005	Intermediate Similarity	NPD6213	Phase 3
0.7	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD1613	Approved
0.6995	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1247	Approved
0.6984	Remote Similarity	NPD7799	Discontinued
0.6982	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7585	Approved
0.6966	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6002	Phase 3
0.6954	Remote Similarity	NPD6005	Phase 3
0.6954	Remote Similarity	NPD7296	Approved
0.6954	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6004	Phase 3
0.6954	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5710	Approved
0.6952	Remote Similarity	NPD5711	Approved
0.6951	Remote Similarity	NPD3705	Approved
0.6949	Remote Similarity	NPD5058	Phase 3
0.694	Remote Similarity	NPD5760	Phase 2
0.694	Remote Similarity	NPD5761	Phase 2
0.6936	Remote Similarity	NPD4308	Phase 3
0.6927	Remote Similarity	NPD1512	Approved
0.6923	Remote Similarity	NPD4625	Phase 3
0.6923	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD8285	Discontinued
0.6895	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD920	Approved
0.6882	Remote Similarity	NPD2313	Discontinued
0.6882	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7985	Registered
0.6864	Remote Similarity	NPD6832	Phase 2
0.686	Remote Similarity	NPD5124	Phase 1
0.686	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1281	Approved
0.6848	Remote Similarity	NPD1091	Approved
0.6845	Remote Similarity	NPD7584	Approved
0.6839	Remote Similarity	NPD7033	Discontinued

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