NPASS Compound

Structure

CID320734 OpenBabel06191716152D 48 51 0 0 1 0 0 0 0 0999 V2000 2.2617 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9345 2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7450 -0.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0238 -2.3328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3986 -1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2646 -1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3986 0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4345 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4345 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 0.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0540 0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3546 -1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 -1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2646 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -0.4173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 0.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0322 0.5862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3765 -1.7976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1306 0.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -2.9173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.4173 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 8 1 0 0 0 0 2 9 2 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 8 10 1 0 0 0 0 9 21 1 0 0 0 0 10 30 1 0 0 0 0 11 14 1 0 0 0 0 11 25 2 0 0 0 0 12 15 2 0 0 0 0 12 25 1 0 0 0 0 13 16 2 0 0 0 0 13 25 1 0 0 0 0 14 26 2 0 0 0 0 15 26 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 36 1 0 0 0 0 19 27 1 0 0 0 0 19 28 2 0 0 0 0 20 27 1 0 0 0 0 20 29 1 0 0 0 0 22 32 1 0 0 0 0 22 36 1 1 0 0 0 23 38 2 0 0 0 0 23 44 1 0 0 0 0 24 39 2 0 0 0 0 24 45 1 0 0 0 0 26 40 1 0 0 0 0 27 46 1 1 0 0 0 28 34 1 0 0 0 0 29 36 1 6 0 0 0 29 37 1 0 0 0 0 30 41 2 0 0 0 0 30 46 1 0 0 0 0 31 42 2 0 0 0 0 31 47 1 0 0 0 0 32 33 1 0 0 0 0 32 47 1 6 0 0 0 33 37 1 1 0 0 0 33 43 1 0 0 0 0 34 44 1 1 0 0 0 34 48 1 0 0 0 0 35 37 1 1 0 0 0 35 45 1 0 0 0 0 35 48 1 0 0 0 0 36 7 1 6 0 0 0 37 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	666.3
Volume:	681.974
LogP:	4.954
LogD:	3.019
LogS:	-4.64
# Rotatable Bonds:	15
TPSA:	154.89
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.104
Synthetic Accessibility Score:	5.915
Fsp3:	0.514
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:	-5.194
MDCK Permeability:	0.00011986343452008441
Pgp-inhibitor:	0.965
Pgp-substrate:	0.767
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.271
Plasma Protein Binding (PPB):	96.35295867919922%
Volume Distribution (VD):	1.518
Pgp-substrate:	4.5354509353637695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.271
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.568
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.73
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.157
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.884
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	4.105
Half-life (T1/2):	0.63

ADMET: Toxicity

hERG Blockers:	0.285
Human Hepatotoxicity (H-HT):	0.945
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.838
Rat Oral Acute Toxicity:	0.901
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.628
Carcinogencity:	0.297
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC320734

Natural Product ID:	NPC320734
*Common Name:**	Caseargrewiin B
IUPAC Name:	[(1S,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-diacetyloxy-10-hydroxy-9-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-7,8-dimethyl-7-[(2Z)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] butanoate
Synonyms:	Caseargrewiin B
Standard InCHIKey:	YJKQLKAAMAXUDU-LRBOKHHASA-N
Standard InCHI:	InChI=1S/C37H46O11/c1-8-10-30(41)46-27-19-28-34(44-23(5)38)48-35(45-24(6)39)37(28)29(20-27)36(7,18-17-21(3)9-2)22(4)32(33(37)43)47-31(42)16-13-25-11-14-26(40)15-12-25/h9,11-17,19,22,27,29,32-35,40,43H,2,8,10,18,20H2,1,3-7H3/b16-13+,21-17-/t22-,27+,29+,32-,33+,34+,35-,36-,37-/m1/s1
SMILES:	CCCC(=O)OC1CC2C(C(C(C(C23C(OC(C3=C1)OC(=O)C)OC(=O)C)O)OC(=O)C=CC4=CC=C(C=C4)O)C)(C)CC=C(C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502864
PubChem CID:	11787194
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	bark	n.a.	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	bark	in the campus of Khon Kaen University, Khon Kaen, Thailand	2001-SEP	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17567069]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26516994]

☑ 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	4
MIC	1

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.3	ug.mL-1	PMID[461179]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[461179]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	2.4	ug.mL-1	PMID[461179]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	ug.mL-1	PMID[461179]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.9	ug.mL-1	PMID[461179]

☑ 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 NPC320734 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	288
0.1-0.2	1062
0.2-0.3	2416
0.3-0.4	4499
0.4-0.5	8942
0.5-0.6	10041
0.6-0.7	11499
0.7-0.8	3616
0.8-0.85	281
0.85-0.9	42
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9362	High Similarity	NPC204644
0.9048	High Similarity	NPC179128
0.9048	High Similarity	NPC116292
0.9048	High Similarity	NPC162569
0.9048	High Similarity	NPC267469
0.9048	High Similarity	NPC35160
0.9048	High Similarity	NPC87630
0.8859	High Similarity	NPC77310
0.8844	High Similarity	NPC470330
0.8803	High Similarity	NPC471872
0.8803	High Similarity	NPC154485
0.8776	High Similarity	NPC208293
0.875	High Similarity	NPC470616
0.875	High Similarity	NPC470617
0.871	High Similarity	NPC477627
0.8696	High Similarity	NPC230331
0.8681	High Similarity	NPC116742
0.8681	High Similarity	NPC139243
0.8645	High Similarity	NPC269668
0.8618	High Similarity	NPC471874
0.8608	High Similarity	NPC469458
0.8608	High Similarity	NPC88176
0.8608	High Similarity	NPC149002
0.8608	High Similarity	NPC469419
0.8608	High Similarity	NPC469396
0.8608	High Similarity	NPC469459
0.8599	High Similarity	NPC100420
0.859	High Similarity	NPC117943
0.859	High Similarity	NPC293568
0.8582	High Similarity	NPC478255
0.8562	High Similarity	NPC27518
0.8562	High Similarity	NPC304110
0.8562	High Similarity	NPC475513
0.8562	High Similarity	NPC473755
0.8552	High Similarity	NPC171134
0.8552	High Similarity	NPC321638
0.8552	High Similarity	NPC321184
0.8552	High Similarity	NPC328273
0.8543	High Similarity	NPC12006
0.8514	High Similarity	NPC184464
0.8514	High Similarity	NPC96447
0.8514	High Similarity	NPC26045
0.8514	High Similarity	NPC251062
0.8514	High Similarity	NPC25491
0.8514	High Similarity	NPC296659
0.8514	High Similarity	NPC202391
0.8514	High Similarity	NPC141455
0.8514	High Similarity	NPC296954
0.8514	High Similarity	NPC196063
0.8514	High Similarity	NPC300894
0.8509	High Similarity	NPC477617
0.85	High Similarity	NPC225307
0.8497	Intermediate Similarity	NPC257847
0.8489	Intermediate Similarity	NPC471157
0.8478	Intermediate Similarity	NPC474532
0.8452	Intermediate Similarity	NPC228357
0.8451	Intermediate Similarity	NPC46137
0.8451	Intermediate Similarity	NPC235294
0.8446	Intermediate Similarity	NPC40305
0.8446	Intermediate Similarity	NPC186296
0.8446	Intermediate Similarity	NPC105005
0.8446	Intermediate Similarity	NPC235557
0.8435	Intermediate Similarity	NPC7518
0.8435	Intermediate Similarity	NPC47471
0.8435	Intermediate Similarity	NPC154262
0.8435	Intermediate Similarity	NPC159387
0.8435	Intermediate Similarity	NPC137501
0.8435	Intermediate Similarity	NPC476377
0.8431	Intermediate Similarity	NPC478268
0.8429	Intermediate Similarity	NPC173150
0.8429	Intermediate Similarity	NPC35288
0.8429	Intermediate Similarity	NPC103533
0.8429	Intermediate Similarity	NPC471882
0.8429	Intermediate Similarity	NPC45224
0.8429	Intermediate Similarity	NPC471881
0.8429	Intermediate Similarity	NPC288416
0.8429	Intermediate Similarity	NPC156692
0.8428	Intermediate Similarity	NPC265600
0.8425	Intermediate Similarity	NPC89105
0.8425	Intermediate Similarity	NPC81515
0.8425	Intermediate Similarity	NPC476383
0.8425	Intermediate Similarity	NPC472350
0.8425	Intermediate Similarity	NPC64141
0.8425	Intermediate Similarity	NPC68092
0.8425	Intermediate Similarity	NPC197316
0.8421	Intermediate Similarity	NPC35097
0.8417	Intermediate Similarity	NPC126991
0.8417	Intermediate Similarity	NPC83218
0.8411	Intermediate Similarity	NPC120728
0.8406	Intermediate Similarity	NPC470815
0.8403	Intermediate Similarity	NPC169398
0.8403	Intermediate Similarity	NPC471883
0.8403	Intermediate Similarity	NPC287597
0.8403	Intermediate Similarity	NPC34293
0.8403	Intermediate Similarity	NPC886
0.84	Intermediate Similarity	NPC229505
0.8395	Intermediate Similarity	NPC469773
0.8395	Intermediate Similarity	NPC469776
0.8395	Intermediate Similarity	NPC469772
0.8395	Intermediate Similarity	NPC100925
0.8395	Intermediate Similarity	NPC13989
0.8395	Intermediate Similarity	NPC148185
0.8395	Intermediate Similarity	NPC469777
0.8395	Intermediate Similarity	NPC295941
0.8395	Intermediate Similarity	NPC469778
0.8395	Intermediate Similarity	NPC32723
0.8395	Intermediate Similarity	NPC469775
0.8395	Intermediate Similarity	NPC135334
0.8395	Intermediate Similarity	NPC469774
0.8385	Intermediate Similarity	NPC471870
0.8378	Intermediate Similarity	NPC296643
0.8367	Intermediate Similarity	NPC271494
0.8367	Intermediate Similarity	NPC473799
0.8367	Intermediate Similarity	NPC473591
0.8367	Intermediate Similarity	NPC475530
0.8367	Intermediate Similarity	NPC155192
0.8357	Intermediate Similarity	NPC61181
0.8356	Intermediate Similarity	NPC216940
0.8356	Intermediate Similarity	NPC22676
0.8356	Intermediate Similarity	NPC475482
0.8356	Intermediate Similarity	NPC260425
0.8356	Intermediate Similarity	NPC198621
0.8354	Intermediate Similarity	NPC475613
0.8345	Intermediate Similarity	NPC263829
0.8344	Intermediate Similarity	NPC478269
0.8333	Intermediate Similarity	NPC28637
0.8333	Intermediate Similarity	NPC254398
0.8323	Intermediate Similarity	NPC286809
0.8322	Intermediate Similarity	NPC476381
0.8322	Intermediate Similarity	NPC269141
0.8322	Intermediate Similarity	NPC476378
0.8322	Intermediate Similarity	NPC96795
0.8322	Intermediate Similarity	NPC476384
0.8322	Intermediate Similarity	NPC246869
0.8322	Intermediate Similarity	NPC138777
0.8322	Intermediate Similarity	NPC298257
0.8322	Intermediate Similarity	NPC281798
0.8322	Intermediate Similarity	NPC119537
0.8322	Intermediate Similarity	NPC247032
0.8322	Intermediate Similarity	NPC476397
0.8322	Intermediate Similarity	NPC476375
0.8322	Intermediate Similarity	NPC225384
0.8322	Intermediate Similarity	NPC476380
0.8322	Intermediate Similarity	NPC264632
0.8322	Intermediate Similarity	NPC175214
0.8322	Intermediate Similarity	NPC205864
0.8322	Intermediate Similarity	NPC219677
0.8322	Intermediate Similarity	NPC112
0.8322	Intermediate Similarity	NPC76406
0.8311	Intermediate Similarity	NPC476385
0.8311	Intermediate Similarity	NPC134405
0.8301	Intermediate Similarity	NPC327962
0.8299	Intermediate Similarity	NPC205195
0.8299	Intermediate Similarity	NPC182249
0.8299	Intermediate Similarity	NPC220942
0.8298	Intermediate Similarity	NPC106677
0.8289	Intermediate Similarity	NPC469448
0.8288	Intermediate Similarity	NPC249817
0.8288	Intermediate Similarity	NPC470572
0.828	Intermediate Similarity	NPC471878
0.8278	Intermediate Similarity	NPC473147
0.8276	Intermediate Similarity	NPC473216
0.8276	Intermediate Similarity	NPC473399
0.8267	Intermediate Similarity	NPC64195
0.8267	Intermediate Similarity	NPC194938
0.8264	Intermediate Similarity	NPC473285
0.8264	Intermediate Similarity	NPC473924
0.8255	Intermediate Similarity	NPC222433
0.8255	Intermediate Similarity	NPC265648
0.825	Intermediate Similarity	NPC471861
0.825	Intermediate Similarity	NPC120012
0.8243	Intermediate Similarity	NPC164743
0.8243	Intermediate Similarity	NPC471875
0.8242	Intermediate Similarity	NPC469397
0.8239	Intermediate Similarity	NPC478267
0.8235	Intermediate Similarity	NPC96599
0.8232	Intermediate Similarity	NPC471871
0.8231	Intermediate Similarity	NPC78363
0.8231	Intermediate Similarity	NPC101686
0.8231	Intermediate Similarity	NPC476376
0.8231	Intermediate Similarity	NPC469364
0.8231	Intermediate Similarity	NPC65262
0.8228	Intermediate Similarity	NPC173726
0.8228	Intermediate Similarity	NPC241600
0.8227	Intermediate Similarity	NPC252114
0.8224	Intermediate Similarity	NPC472936
0.8224	Intermediate Similarity	NPC472938
0.8224	Intermediate Similarity	NPC472937
0.8219	Intermediate Similarity	NPC477874
0.8219	Intermediate Similarity	NPC173569
0.8217	Intermediate Similarity	NPC11411
0.8214	Intermediate Similarity	NPC265413
0.8214	Intermediate Similarity	NPC10154
0.8212	Intermediate Similarity	NPC287615
0.8212	Intermediate Similarity	NPC83743
0.8212	Intermediate Similarity	NPC53520
0.8212	Intermediate Similarity	NPC262182
0.8212	Intermediate Similarity	NPC216819
0.8201	Intermediate Similarity	NPC52097
0.82	Intermediate Similarity	NPC478250

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 NPC320734 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	698
0.2-0.3	1500
0.3-0.4	2678
0.4-0.5	2263
0.5-0.6	1261
0.6-0.7	458
0.7-0.8	57
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8425	Intermediate Similarity	NPD7266	Discontinued
0.8013	Intermediate Similarity	NPD8166	Discontinued
0.7911	Intermediate Similarity	NPD37	Approved
0.7888	Intermediate Similarity	NPD6234	Discontinued
0.7879	Intermediate Similarity	NPD7228	Approved
0.7875	Intermediate Similarity	NPD4967	Phase 2
0.7875	Intermediate Similarity	NPD4965	Approved
0.7875	Intermediate Similarity	NPD4966	Approved
0.7719	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD8127	Discontinued
0.7671	Intermediate Similarity	NPD5736	Approved
0.7548	Intermediate Similarity	NPD4628	Phase 3
0.7531	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD7240	Approved
0.7485	Intermediate Similarity	NPD7685	Pre-registration
0.7471	Intermediate Similarity	NPD8434	Phase 2
0.7467	Intermediate Similarity	NPD6663	Approved
0.7456	Intermediate Similarity	NPD7799	Discontinued
0.7438	Intermediate Similarity	NPD1653	Approved
0.7415	Intermediate Similarity	NPD3094	Phase 2
0.7412	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7372	Intermediate Similarity	NPD6674	Discontinued
0.7365	Intermediate Similarity	NPD7199	Phase 2
0.7361	Intermediate Similarity	NPD5125	Phase 3
0.7361	Intermediate Similarity	NPD5126	Approved
0.7353	Intermediate Similarity	NPD3818	Discontinued
0.7333	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3764	Approved
0.7273	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7097	Phase 1
0.726	Intermediate Similarity	NPD3092	Approved
0.7244	Intermediate Similarity	NPD5762	Approved
0.7244	Intermediate Similarity	NPD5763	Approved
0.7239	Intermediate Similarity	NPD7028	Phase 2
0.7209	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4140	Approved
0.719	Intermediate Similarity	NPD4060	Phase 1
0.719	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8150	Discontinued
0.7168	Intermediate Similarity	NPD7074	Phase 3
0.7159	Intermediate Similarity	NPD8407	Phase 2
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7123	Intermediate Similarity	NPD2932	Approved
0.7114	Intermediate Similarity	NPD8651	Approved
0.711	Intermediate Similarity	NPD7054	Approved
0.7105	Intermediate Similarity	NPD7095	Approved
0.7103	Intermediate Similarity	NPD3091	Approved
0.7099	Intermediate Similarity	NPD6273	Approved
0.7097	Intermediate Similarity	NPD7680	Approved
0.7086	Intermediate Similarity	NPD8368	Discontinued
0.7083	Intermediate Similarity	NPD7075	Discontinued
0.7078	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3620	Phase 2
0.7069	Intermediate Similarity	NPD7472	Approved
0.7065	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7808	Phase 3
0.7037	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5735	Approved
0.703	Intermediate Similarity	NPD4380	Phase 2
0.7027	Intermediate Similarity	NPD1091	Approved
0.7027	Intermediate Similarity	NPD3705	Approved
0.7024	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7236	Approved
0.7011	Intermediate Similarity	NPD5844	Phase 1
0.7007	Intermediate Similarity	NPD3019	Approved
0.7006	Intermediate Similarity	NPD7819	Suspended
0.7	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4110	Phase 3
0.6994	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7473	Discontinued
0.6993	Remote Similarity	NPD3027	Phase 3
0.6989	Remote Similarity	NPD7251	Discontinued
0.6987	Remote Similarity	NPD6653	Approved
0.6986	Remote Similarity	NPD7741	Discontinued
0.6968	Remote Similarity	NPD8320	Phase 1
0.6968	Remote Similarity	NPD8319	Approved
0.6966	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2629	Approved
0.6939	Remote Similarity	NPD1357	Approved
0.6932	Remote Similarity	NPD6797	Phase 2
0.6923	Remote Similarity	NPD230	Phase 1
0.6919	Remote Similarity	NPD6232	Discontinued
0.6918	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6005	Phase 3
0.6918	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6004	Phase 3
0.6918	Remote Similarity	NPD6002	Phase 3
0.6914	Remote Similarity	NPD5058	Phase 3
0.6909	Remote Similarity	NPD7239	Suspended
0.6908	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8032	Phase 2
0.6897	Remote Similarity	NPD4198	Discontinued
0.6897	Remote Similarity	NPD7157	Approved
0.6894	Remote Similarity	NPD3750	Approved
0.6894	Remote Similarity	NPD7003	Approved
0.6892	Remote Similarity	NPD3095	Discontinued
0.6892	Remote Similarity	NPD4626	Approved
0.6871	Remote Similarity	NPD9545	Approved
0.6863	Remote Similarity	NPD2861	Phase 2
0.6859	Remote Similarity	NPD1613	Approved
0.6859	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2438	Suspended
0.6855	Remote Similarity	NPD2935	Discontinued
0.6853	Remote Similarity	NPD969	Suspended
0.6852	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6801	Discontinued
0.6839	Remote Similarity	NPD6798	Discontinued
0.6832	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2533	Approved
0.6829	Remote Similarity	NPD2534	Approved
0.6829	Remote Similarity	NPD2532	Approved
0.6828	Remote Similarity	NPD7699	Phase 2
0.6828	Remote Similarity	NPD7700	Phase 2
0.6826	Remote Similarity	NPD6599	Discontinued
0.6825	Remote Similarity	NPD7435	Discontinued
0.6824	Remote Similarity	NPD7768	Phase 2
0.6824	Remote Similarity	NPD5691	Approved
0.6823	Remote Similarity	NPD8151	Discontinued
0.6821	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5124	Phase 1
0.6813	Remote Similarity	NPD8360	Approved
0.6813	Remote Similarity	NPD8361	Approved
0.6805	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6233	Phase 2
0.6792	Remote Similarity	NPD7033	Discontinued
0.677	Remote Similarity	NPD2424	Discontinued
0.6766	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3751	Discontinued
0.6757	Remote Similarity	NPD6535	Approved
0.6757	Remote Similarity	NPD6534	Approved
0.6754	Remote Similarity	NPD7999	Approved
0.675	Remote Similarity	NPD6099	Approved
0.675	Remote Similarity	NPD5406	Approved
0.675	Remote Similarity	NPD6100	Approved
0.675	Remote Similarity	NPD5405	Approved
0.675	Remote Similarity	NPD5408	Approved
0.675	Remote Similarity	NPD5404	Approved
0.6746	Remote Similarity	NPD1934	Approved
0.6742	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7930	Approved
0.6732	Remote Similarity	NPD2797	Approved
0.6731	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1652	Phase 2
0.6727	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8435	Approved
0.6713	Remote Similarity	NPD3021	Approved
0.6713	Remote Similarity	NPD3022	Approved
0.6711	Remote Similarity	NPD7503	Approved
0.6711	Remote Similarity	NPD5327	Phase 3
0.671	Remote Similarity	NPD4908	Phase 1
0.6706	Remote Similarity	NPD5761	Phase 2
0.6706	Remote Similarity	NPD5760	Phase 2
0.6704	Remote Similarity	NPD6764	Approved
0.6704	Remote Similarity	NPD6765	Approved
0.6701	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7874	Approved
0.669	Remote Similarity	NPD7843	Approved
0.6687	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD6781	Approved
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8404	Phase 2
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6778	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