NPASS Compound

Structure

NPC469352 OpenBabel07101719252D 37 43 0 0 1 0 0 0 0 0999 V2000 3.0578 2.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7315 -1.9229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2474 0.8518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6965 0.0172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6240 -2.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5704 -2.0948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7790 1.2523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0904 -0.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6168 2.9584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1104 0.8550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6894 1.3420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7346 1.5471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9314 -1.3231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0242 -1.6179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5554 -1.0949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1894 -0.8486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7640 0.2524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3129 0.5602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3773 0.1748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2403 2.1766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6806 2.6071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2884 -0.4147 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9463 -0.3232 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3102 0.7293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2491 0.9116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0659 0.5602 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6894 1.3420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5998 -0.8001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1894 -1.8486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5783 0.4695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8460 3.1580 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3101 0.7144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7990 -0.1200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7104 -0.0708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2043 1.9106 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7255 1.6081 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 12 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 12 2 0 0 0 0 8 16 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 9 21 1 0 0 0 0 10 19 1 0 0 0 0 10 26 1 0 0 0 0 11 26 1 0 0 0 0 12 24 1 0 0 0 0 13 2 1 1 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 28 1 1 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 16 29 1 6 0 0 0 17 7 1 1 0 0 0 17 23 1 0 0 0 0 17 34 1 0 0 0 0 18 25 1 0 0 0 0 18 27 1 1 0 0 0 19 28 1 6 0 0 0 19 30 1 0 0 0 0 20 27 1 6 0 0 0 20 35 1 0 0 0 0 21 31 2 0 0 0 0 21 36 1 0 0 0 0 22 26 1 6 0 0 0 23 37 1 6 0 0 0 24 32 2 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 33 1 6 0 0 0 27 11 1 1 0 0 0 27 36 1 0 0 0 0 28 15 1 1 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	720.28
Volume:	672.844
LogP:	-0.035
LogD:	-0.366
LogS:	-2.86
# Rotatable Bonds:	13
TPSA:	283.98
# H-Bond Aceptor:	18
# H-Bond Donor:	10
# Rings:	4
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.06
Synthetic Accessibility Score:	5.626
Fsp3:	0.719
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.74
MDCK Permeability:	9.324579878011718e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.935
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206
Plasma Protein Binding (PPB):	57.46483612060547%
Volume Distribution (VD):	0.366
Pgp-substrate:	28.878292083740234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.3
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	1.129
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.408
Drug-inuced Liver Injury (DILI):	0.231
AMES Toxicity:	0.204
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.048
Carcinogencity:	0.267
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.818

Download Data

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

Natural Product: NPC469352

Natural Product ID:	NPC469352
*Common Name:**	Schirubridilactone F
IUPAC Name:	n.a.
Synonyms:	Schirubridilactone F
Standard InCHIKey:	DBZQQSSVNJNBJN-HAWFGQBZSA-N
Standard InCHI:	InChI=1S/C28H36O9/c1-12-7-17(34-24(12)32)23-13(2)14-5-6-15-22-16(29)8-18-25(3,4)35-20-9-21(31)36-27(18,20)11-26(22,33)10-19(30)28(14,15)37-23/h6-7,13-14,16-20,22-23,29-30,33H,5,8-11H2,1-4H3/t13-,14+,16+,17+,18-,19-,20+,22+,23-,26-,27+,28-/m0/s1
SMILES:	O=C1C[C@@H]2[C@@]3(O1)C[C@@]1(O)C[C@H](O)[C@]45C(=CC[C@@H]5[C@@H]([C@H](O4)[C@H]4C=C(C(=O)O4)C)C)[C@@H]1[C@@H](C[C@H]3C(O2)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076671
PubChem CID:	46880615
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001816] Furofurans

*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
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17489633]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[20146529]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	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
EC50	1
IC50	2
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[529936]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[529936]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	50.1	ug.mL-1	PMID[529936]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Selectivity Index	=	3.5	n.a.	PMID[529936]

☑ 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 NPC469352 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	259
0.1-0.2	1489
0.2-0.3	4806
0.3-0.4	8370
0.4-0.5	14431
0.5-0.6	8089
0.6-0.7	4571
0.7-0.8	664
0.8-0.85	11
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC475371
0.9316	High Similarity	NPC129992
0.913	High Similarity	NPC475323
0.8655	High Similarity	NPC312536
0.8644	High Similarity	NPC473656
0.8571	High Similarity	NPC475372
0.8374	Intermediate Similarity	NPC473802
0.8347	Intermediate Similarity	NPC469380
0.8306	Intermediate Similarity	NPC473919
0.8306	Intermediate Similarity	NPC473709
0.8254	Intermediate Similarity	NPC470850
0.824	Intermediate Similarity	NPC471939
0.8235	Intermediate Similarity	NPC473535
0.8203	Intermediate Similarity	NPC180902
0.8203	Intermediate Similarity	NPC475139
0.8189	Intermediate Similarity	NPC231529
0.8182	Intermediate Similarity	NPC475238
0.8175	Intermediate Similarity	NPC471940
0.8158	Intermediate Similarity	NPC86077
0.813	Intermediate Similarity	NPC143755
0.813	Intermediate Similarity	NPC472004
0.813	Intermediate Similarity	NPC4548
0.8115	Intermediate Similarity	NPC124676
0.8115	Intermediate Similarity	NPC146280
0.8099	Intermediate Similarity	NPC471127
0.8099	Intermediate Similarity	NPC234858
0.8099	Intermediate Similarity	NPC154363
0.8099	Intermediate Similarity	NPC470793
0.8095	Intermediate Similarity	NPC217901
0.8083	Intermediate Similarity	NPC470120
0.808	Intermediate Similarity	NPC469382
0.808	Intermediate Similarity	NPC472399
0.8077	Intermediate Similarity	NPC473548
0.8077	Intermediate Similarity	NPC223356
0.8077	Intermediate Similarity	NPC471136
0.8077	Intermediate Similarity	NPC100017
0.8077	Intermediate Similarity	NPC475500
0.8077	Intermediate Similarity	NPC182266
0.8077	Intermediate Similarity	NPC475154
0.8077	Intermediate Similarity	NPC471137
0.8049	Intermediate Similarity	NPC472667
0.8047	Intermediate Similarity	NPC162495
0.8047	Intermediate Similarity	NPC470851
0.8034	Intermediate Similarity	NPC26617
0.8033	Intermediate Similarity	NPC10721
0.8031	Intermediate Similarity	NPC475273
0.8031	Intermediate Similarity	NPC168849
0.8017	Intermediate Similarity	NPC90472
0.8017	Intermediate Similarity	NPC472400
0.8016	Intermediate Similarity	NPC86346
0.8016	Intermediate Similarity	NPC75856
0.8016	Intermediate Similarity	NPC469379
0.8	Intermediate Similarity	NPC470063
0.8	Intermediate Similarity	NPC162009
0.8	Intermediate Similarity	NPC257017
0.7984	Intermediate Similarity	NPC477189
0.7984	Intermediate Similarity	NPC473838
0.7984	Intermediate Similarity	NPC251564
0.7984	Intermediate Similarity	NPC145182
0.7984	Intermediate Similarity	NPC475314
0.7984	Intermediate Similarity	NPC475389
0.7984	Intermediate Similarity	NPC471126
0.7984	Intermediate Similarity	NPC475606
0.7984	Intermediate Similarity	NPC157252
0.7984	Intermediate Similarity	NPC471128
0.7984	Intermediate Similarity	NPC475885
0.7955	Intermediate Similarity	NPC68282
0.7939	Intermediate Similarity	NPC476823
0.7934	Intermediate Similarity	NPC477126
0.7934	Intermediate Similarity	NPC472757
0.7923	Intermediate Similarity	NPC34963
0.7923	Intermediate Similarity	NPC473485
0.7923	Intermediate Similarity	NPC474508
0.792	Intermediate Similarity	NPC52839
0.792	Intermediate Similarity	NPC472401
0.7907	Intermediate Similarity	NPC35109
0.7903	Intermediate Similarity	NPC236918
0.7903	Intermediate Similarity	NPC156745
0.7899	Intermediate Similarity	NPC273433
0.7899	Intermediate Similarity	NPC42662
0.7886	Intermediate Similarity	NPC284068
0.7881	Intermediate Similarity	NPC187435
0.7881	Intermediate Similarity	NPC67321
0.7874	Intermediate Similarity	NPC144625
0.7869	Intermediate Similarity	NPC123117
0.7863	Intermediate Similarity	NPC469673
0.7863	Intermediate Similarity	NPC58029
0.7857	Intermediate Similarity	NPC19464
0.7851	Intermediate Similarity	NPC23967
0.7846	Intermediate Similarity	NPC196921
0.7846	Intermediate Similarity	NPC279478
0.7846	Intermediate Similarity	NPC220757
0.7846	Intermediate Similarity	NPC241935
0.7845	Intermediate Similarity	NPC474709
0.784	Intermediate Similarity	NPC472759
0.784	Intermediate Similarity	NPC317635
0.784	Intermediate Similarity	NPC329080
0.784	Intermediate Similarity	NPC329008
0.7833	Intermediate Similarity	NPC474923
0.7833	Intermediate Similarity	NPC48305
0.7833	Intermediate Similarity	NPC475463
0.7833	Intermediate Similarity	NPC475563
0.7833	Intermediate Similarity	NPC475134
0.7829	Intermediate Similarity	NPC476091
0.7829	Intermediate Similarity	NPC236999
0.7829	Intermediate Similarity	NPC476078
0.7823	Intermediate Similarity	NPC472397
0.7823	Intermediate Similarity	NPC472758
0.7823	Intermediate Similarity	NPC171905
0.7823	Intermediate Similarity	NPC471125
0.7823	Intermediate Similarity	NPC161060
0.7815	Intermediate Similarity	NPC94377
0.7805	Intermediate Similarity	NPC106228
0.7805	Intermediate Similarity	NPC138372
0.7797	Intermediate Similarity	NPC243998
0.7797	Intermediate Similarity	NPC470980
0.7797	Intermediate Similarity	NPC223450
0.7795	Intermediate Similarity	NPC471392
0.7795	Intermediate Similarity	NPC473979
0.7778	Intermediate Similarity	NPC61442
0.7769	Intermediate Similarity	NPC475668
0.7769	Intermediate Similarity	NPC475480
0.7769	Intermediate Similarity	NPC473921
0.7769	Intermediate Similarity	NPC13071
0.776	Intermediate Similarity	NPC5989
0.776	Intermediate Similarity	NPC22628
0.776	Intermediate Similarity	NPC9674
0.776	Intermediate Similarity	NPC471108
0.776	Intermediate Similarity	NPC275696
0.776	Intermediate Similarity	NPC19028
0.776	Intermediate Similarity	NPC5991
0.776	Intermediate Similarity	NPC255081
0.7742	Intermediate Similarity	NPC296822
0.7742	Intermediate Similarity	NPC156252
0.7742	Intermediate Similarity	NPC36754
0.7734	Intermediate Similarity	NPC145238
0.7727	Intermediate Similarity	NPC88668
0.7724	Intermediate Similarity	NPC471380
0.7724	Intermediate Similarity	NPC178289
0.7724	Intermediate Similarity	NPC73314
0.7719	Intermediate Similarity	NPC472995
0.7717	Intermediate Similarity	NPC269642
0.7717	Intermediate Similarity	NPC470265
0.7717	Intermediate Similarity	NPC222688
0.7717	Intermediate Similarity	NPC23786
0.7712	Intermediate Similarity	NPC146731
0.7712	Intermediate Similarity	NPC100487
0.7712	Intermediate Similarity	NPC296950
0.7705	Intermediate Similarity	NPC473877
0.7705	Intermediate Similarity	NPC269530
0.7699	Intermediate Similarity	NPC477131
0.7698	Intermediate Similarity	NPC151616
0.7692	Intermediate Similarity	NPC472552
0.7692	Intermediate Similarity	NPC270109
0.7692	Intermediate Similarity	NPC476081
0.7692	Intermediate Similarity	NPC470972
0.7686	Intermediate Similarity	NPC179642
0.768	Intermediate Similarity	NPC159928
0.768	Intermediate Similarity	NPC288679
0.768	Intermediate Similarity	NPC106644
0.7674	Intermediate Similarity	NPC473635
0.7674	Intermediate Similarity	NPC15095
0.7674	Intermediate Similarity	NPC293112
0.7672	Intermediate Similarity	NPC272223
0.7667	Intermediate Similarity	NPC29827
0.7667	Intermediate Similarity	NPC306265
0.7664	Intermediate Similarity	NPC48414
0.7664	Intermediate Similarity	NPC5153
0.7661	Intermediate Similarity	NPC474333
0.7661	Intermediate Similarity	NPC471816
0.7656	Intermediate Similarity	NPC11895
0.7656	Intermediate Similarity	NPC67251
0.7656	Intermediate Similarity	NPC1538
0.7652	Intermediate Similarity	NPC199099
0.7652	Intermediate Similarity	NPC472998
0.7652	Intermediate Similarity	NPC472769
0.7647	Intermediate Similarity	NPC470979
0.7647	Intermediate Similarity	NPC475217
0.7647	Intermediate Similarity	NPC470975
0.7647	Intermediate Similarity	NPC103088
0.7647	Intermediate Similarity	NPC472655
0.7638	Intermediate Similarity	NPC310511
0.7638	Intermediate Similarity	NPC67569
0.7634	Intermediate Similarity	NPC104382
0.7634	Intermediate Similarity	NPC472770
0.763	Intermediate Similarity	NPC246209
0.7627	Intermediate Similarity	NPC69171
0.7627	Intermediate Similarity	NPC474165
0.7627	Intermediate Similarity	NPC159533
0.7627	Intermediate Similarity	NPC72842
0.7627	Intermediate Similarity	NPC99510
0.7619	Intermediate Similarity	NPC473636
0.7619	Intermediate Similarity	NPC476107
0.7619	Intermediate Similarity	NPC473839
0.7619	Intermediate Similarity	NPC230513
0.7619	Intermediate Similarity	NPC77689
0.7619	Intermediate Similarity	NPC470186
0.7619	Intermediate Similarity	NPC211093
0.7615	Intermediate Similarity	NPC146456
0.7615	Intermediate Similarity	NPC298841

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 NPC469352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	1944
0.2-0.3	3867
0.3-0.4	2130
0.4-0.5	630
0.5-0.6	271
0.6-0.7	74
0.7-0.8	2
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
0.8034	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6371	Approved
0.75	Intermediate Similarity	NPD7319	Approved
0.7344	Intermediate Similarity	NPD7516	Approved
0.7323	Intermediate Similarity	NPD7115	Discovery
0.7317	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5344	Discontinued
0.7288	Intermediate Similarity	NPD4225	Approved
0.7273	Intermediate Similarity	NPD7507	Approved
0.7266	Intermediate Similarity	NPD7328	Approved
0.7266	Intermediate Similarity	NPD7327	Approved
0.7258	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6686	Approved
0.7023	Intermediate Similarity	NPD6319	Approved
0.7016	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6053	Discontinued
0.6983	Remote Similarity	NPD46	Approved
0.6983	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD8335	Approved
0.697	Remote Similarity	NPD8379	Approved
0.697	Remote Similarity	NPD8378	Approved
0.697	Remote Similarity	NPD8033	Approved
0.697	Remote Similarity	NPD8296	Approved
0.697	Remote Similarity	NPD8380	Approved
0.6963	Remote Similarity	NPD7078	Approved
0.696	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6648	Approved
0.694	Remote Similarity	NPD7492	Approved
0.6897	Remote Similarity	NPD1695	Approved
0.6894	Remote Similarity	NPD8377	Approved
0.6894	Remote Similarity	NPD6054	Approved
0.6894	Remote Similarity	NPD8294	Approved
0.6891	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6616	Approved
0.686	Remote Similarity	NPD7638	Approved
0.6803	Remote Similarity	NPD7640	Approved
0.6803	Remote Similarity	NPD7639	Approved
0.6791	Remote Similarity	NPD6370	Approved
0.6788	Remote Similarity	NPD7736	Approved
0.6767	Remote Similarity	NPD6059	Approved
0.6744	Remote Similarity	NPD8297	Approved
0.6716	Remote Similarity	NPD8517	Approved
0.6716	Remote Similarity	NPD6016	Approved
0.6716	Remote Similarity	NPD8516	Approved
0.6716	Remote Similarity	NPD6015	Approved
0.6716	Remote Similarity	NPD8515	Approved
0.6716	Remote Similarity	NPD8513	Phase 3
0.6715	Remote Similarity	NPD8293	Discontinued
0.6692	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6641	Remote Similarity	NPD6373	Approved
0.6641	Remote Similarity	NPD6372	Approved
0.6593	Remote Similarity	NPD7503	Approved
0.6562	Remote Similarity	NPD6881	Approved
0.6562	Remote Similarity	NPD7320	Approved
0.6562	Remote Similarity	NPD6899	Approved
0.6555	Remote Similarity	NPD7838	Discovery
0.6535	Remote Similarity	NPD6402	Approved
0.6535	Remote Similarity	NPD5739	Approved
0.6535	Remote Similarity	NPD6675	Approved
0.6535	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD7983	Approved
0.6489	Remote Similarity	NPD6882	Approved
0.6484	Remote Similarity	NPD5697	Approved
0.648	Remote Similarity	NPD1700	Approved
0.6475	Remote Similarity	NPD8074	Phase 3
0.6471	Remote Similarity	NPD6921	Approved
0.6462	Remote Similarity	NPD4634	Approved
0.6462	Remote Similarity	NPD7290	Approved
0.6462	Remote Similarity	NPD6883	Approved
0.6462	Remote Similarity	NPD7102	Approved
0.6418	Remote Similarity	NPD6009	Approved
0.6417	Remote Similarity	NPD5785	Approved
0.6412	Remote Similarity	NPD6617	Approved
0.6412	Remote Similarity	NPD8130	Phase 1
0.6412	Remote Similarity	NPD6847	Approved
0.6412	Remote Similarity	NPD6869	Approved
0.6412	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5282	Discontinued
0.6385	Remote Similarity	NPD6012	Approved
0.6385	Remote Similarity	NPD6013	Approved
0.6385	Remote Similarity	NPD6014	Approved
0.6377	Remote Similarity	NPD8328	Phase 3
0.6377	Remote Similarity	NPD7604	Phase 2
0.6357	Remote Similarity	NPD6412	Phase 2
0.6357	Remote Similarity	NPD5701	Approved
0.635	Remote Similarity	NPD5983	Phase 2
0.632	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8133	Approved
0.6312	Remote Similarity	NPD6033	Approved
0.6311	Remote Similarity	NPD5778	Approved
0.6311	Remote Similarity	NPD6399	Phase 3
0.6311	Remote Similarity	NPD5779	Approved
0.6308	Remote Similarity	NPD6011	Approved
0.6299	Remote Similarity	NPD7632	Discontinued
0.6286	Remote Similarity	NPD6336	Discontinued
0.6271	Remote Similarity	NPD5363	Approved
0.626	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6083	Phase 2
0.624	Remote Similarity	NPD6084	Phase 2
0.6239	Remote Similarity	NPD5362	Discontinued
0.623	Remote Similarity	NPD7637	Suspended
0.621	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5211	Phase 2
0.6167	Remote Similarity	NPD4251	Approved
0.6167	Remote Similarity	NPD4250	Approved
0.6165	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD5286	Approved
0.6142	Remote Similarity	NPD4696	Approved
0.6142	Remote Similarity	NPD5285	Approved
0.6134	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD1694	Approved
0.6134	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7902	Approved
0.6111	Remote Similarity	NPD4755	Approved
0.6103	Remote Similarity	NPD6274	Approved
0.6087	Remote Similarity	NPD7101	Approved
0.6087	Remote Similarity	NPD7100	Approved
0.6083	Remote Similarity	NPD4249	Approved
0.6081	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.608	Remote Similarity	NPD5695	Phase 3
0.6077	Remote Similarity	NPD5141	Approved
0.6069	Remote Similarity	NPD7260	Phase 2
0.6068	Remote Similarity	NPD5369	Approved
0.6063	Remote Similarity	NPD5696	Approved
0.6048	Remote Similarity	NPD4202	Approved
0.6047	Remote Similarity	NPD5226	Approved
0.6047	Remote Similarity	NPD5224	Approved
0.6047	Remote Similarity	NPD5225	Approved
0.6047	Remote Similarity	NPD4633	Approved
0.6033	Remote Similarity	NPD7524	Approved
0.6028	Remote Similarity	NPD6067	Discontinued
0.6027	Remote Similarity	NPD8338	Approved
0.6027	Remote Similarity	NPD6845	Suspended
0.6017	Remote Similarity	NPD4270	Approved
0.6017	Remote Similarity	NPD4269	Approved
0.6016	Remote Similarity	NPD4700	Approved
0.6014	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD5956	Approved
0.6	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD7748	Approved
0.5969	Remote Similarity	NPD5223	Approved
0.5968	Remote Similarity	NPD8034	Phase 2
0.5968	Remote Similarity	NPD6079	Approved
0.5968	Remote Similarity	NPD8035	Phase 2
0.5968	Remote Similarity	NPD7515	Phase 2
0.5966	Remote Similarity	NPD7154	Phase 3
0.595	Remote Similarity	NPD5786	Approved
0.595	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.595	Remote Similarity	NPD3618	Phase 1
0.5944	Remote Similarity	NPD8273	Phase 1
0.5942	Remote Similarity	NPD6317	Approved
0.594	Remote Similarity	NPD4729	Approved
0.594	Remote Similarity	NPD4730	Approved
0.5935	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD6101	Approved
0.5935	Remote Similarity	NPD7625	Phase 1
0.5935	Remote Similarity	NPD5328	Approved
0.5915	Remote Similarity	NPD7642	Approved
0.5909	Remote Similarity	NPD4767	Approved
0.5909	Remote Similarity	NPD4768	Approved
0.5899	Remote Similarity	NPD6313	Approved
0.5899	Remote Similarity	NPD6314	Approved
0.5887	Remote Similarity	NPD8266	Approved
0.5887	Remote Similarity	NPD8268	Approved
0.5887	Remote Similarity	NPD6909	Approved
0.5887	Remote Similarity	NPD8267	Approved
0.5887	Remote Similarity	NPD6908	Approved
0.5887	Remote Similarity	NPD8269	Approved
0.5873	Remote Similarity	NPD7900	Approved
0.5873	Remote Similarity	NPD6001	Approved
0.5873	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6903	Approved
0.5852	Remote Similarity	NPD5247	Approved
0.5852	Remote Similarity	NPD5249	Phase 3
0.5852	Remote Similarity	NPD5250	Approved
0.5852	Remote Similarity	NPD5251	Approved
0.5852	Remote Similarity	NPD5248	Approved
0.5847	Remote Similarity	NPD4820	Approved
0.5847	Remote Similarity	NPD4821	Approved
0.5847	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD4252	Approved
0.5847	Remote Similarity	NPD4822	Approved
0.5847	Remote Similarity	NPD4819	Approved
0.584	Remote Similarity	NPD6411	Approved
0.584	Remote Similarity	NPD5693	Phase 1
0.584	Remote Similarity	NPD5284	Approved
0.584	Remote Similarity	NPD5281	Approved
0.5833	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5828	Remote Similarity	NPD6333	Approved
0.5828	Remote Similarity	NPD6334	Approved
0.5827	Remote Similarity	NPD4629	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