NPASS Compound

Structure

NPC311166 OpenBabel07101718192D 37 39 0 0 1 0 0 0 0 0999 V2000 -3.8939 -3.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7611 -1.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7861 -2.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7055 0.4069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7014 0.5584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0195 2.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3486 -1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0495 -4.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7861 -1.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2051 -3.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3608 -4.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5164 -3.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3236 -1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0167 0.4069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8361 -1.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1724 -0.0806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3280 -2.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0167 -2.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2986 -1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8611 -0.0806 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0027 -0.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9732 2.2745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1724 -3.0056 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3280 -1.5431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0167 -1.5431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3280 -4.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3966 -0.8907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9697 -0.1019 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8611 -1.0556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1724 -1.0556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9564 -0.5716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6256 2.9991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3280 -5.4431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3503 -1.0934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2745 1.3472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1724 -3.9806 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 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 8 10 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 29 1 0 0 0 0 17 23 1 0 0 0 0 17 24 2 0 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 20 29 1 1 0 0 0 21 31 2 0 0 0 0 21 34 1 0 0 0 0 22 32 2 0 0 0 0 22 35 1 0 0 0 0 23 36 1 1 0 0 0 24 27 1 0 0 0 0 24 30 1 0 0 0 0 25 29 1 6 0 0 0 25 30 1 0 0 0 0 26 33 2 0 0 0 0 26 36 1 0 0 0 0 27 34 1 1 0 0 0 27 37 1 0 0 0 0 28 30 1 1 0 0 0 28 35 1 0 0 0 0 28 37 1 0 0 0 0 29 7 1 6 0 0 0 30 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.31
Volume:	547.479
LogP:	5.566
LogD:	4.256
LogS:	-5.887
# Rotatable Bonds:	13
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.113
Synthetic Accessibility Score:	5.509
Fsp3:	0.7
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:	-4.613
MDCK Permeability:	4.985224950360134e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.781
30% Bioavailability (F30%):	0.823

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.213
Plasma Protein Binding (PPB):	96.06820678710938%
Volume Distribution (VD):	2.305
Pgp-substrate:	2.754638910293579%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.521
CYP2C19-substrate:	0.23
CYP2C9-inhibitor:	0.66
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.126
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.884
CYP3A4-substrate:	0.453

ADMET: Excretion

Clearance (CL):	3.874
Half-life (T1/2):	0.083

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.942
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.984
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.725
Carcinogencity:	0.548
Eye Corrosion:	0.203
Eye Irritation:	0.147
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC311166

Natural Product ID:	NPC311166
*Common Name:**	Caseargrewins H
IUPAC Name:	[(1S,3R,5R,6aS,7R,8R,10aS)-1,3-diacetyloxy-7,8-dimethyl-7-[(2Z)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] hexanoate
Synonyms:	caseargrewins H
Standard InCHIKey:	BCVXZPHRQXQURQ-RYILYFAJSA-N
Standard InCHI:	InChI=1S/C30H44O7/c1-8-10-11-12-26(33)36-23-17-24-27(34-21(5)31)37-28(35-22(6)32)30(24)16-14-20(4)29(7,25(30)18-23)15-13-19(3)9-2/h9,13,17,20,23,25,27-28H,2,8,10-12,14-16,18H2,1,3-7H3/b19-13-/t20-,23+,25+,27+,28-,29-,30-/m1/s1
SMILES:	CCCCCC(=O)O[C@H]1C=C2[C@@H](OC(=O)C)O[C@H]([C@]32[C@@H](C1)[C@](C)(C/C=C(C=C)/C)[C@@H](CC3)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL231313
PubChem CID:	16756887
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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.88	ug.mL-1	PMID[521442]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	0.54	ug.mL-1	PMID[521442]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.21	ug.mL-1	PMID[521442]

☑ 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 NPC311166 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	209
0.1-0.2	1009
0.2-0.3	4049
0.3-0.4	9732
0.4-0.5	12575
0.5-0.6	7512
0.6-0.7	6503
0.7-0.8	985
0.8-0.85	44
0.85-0.9	49
0.9-0.95	28
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC88507
0.9255	High Similarity	NPC473204
0.9247	High Similarity	NPC472188
0.9175	High Similarity	NPC252296
0.9149	High Similarity	NPC471366
0.9149	High Similarity	NPC476800
0.9149	High Similarity	NPC318917
0.9149	High Similarity	NPC472186
0.9082	High Similarity	NPC184512
0.9053	High Similarity	NPC472187
0.9053	High Similarity	NPC473545
0.9043	High Similarity	NPC98112
0.9032	High Similarity	NPC471362
0.9032	High Similarity	NPC472189
0.9032	High Similarity	NPC471372
0.8969	High Similarity	NPC134270
0.8936	High Similarity	NPC171598
0.8878	High Similarity	NPC201880
0.8878	High Similarity	NPC264867
0.8878	High Similarity	NPC470321
0.8878	High Similarity	NPC473207
0.8878	High Similarity	NPC81567
0.8866	High Similarity	NPC471363
0.8866	High Similarity	NPC238397
0.8812	High Similarity	NPC119550
0.8776	High Similarity	NPC127933
0.8776	High Similarity	NPC7644
0.8776	High Similarity	NPC475889
0.8776	High Similarity	NPC7613
0.8737	High Similarity	NPC112654
0.8614	High Similarity	NPC311223
0.8586	High Similarity	NPC132395
0.8586	High Similarity	NPC471365
0.8586	High Similarity	NPC471364
0.8542	High Similarity	NPC94905
0.8542	High Similarity	NPC8954
0.8529	High Similarity	NPC316974
0.8515	High Similarity	NPC88013
0.8515	High Similarity	NPC125423
0.8511	High Similarity	NPC65513
0.8495	Intermediate Similarity	NPC293044
0.8431	Intermediate Similarity	NPC135015
0.8431	Intermediate Similarity	NPC48548
0.8431	Intermediate Similarity	NPC128795
0.8431	Intermediate Similarity	NPC217921
0.8416	Intermediate Similarity	NPC172867
0.8387	Intermediate Similarity	NPC477128
0.835	Intermediate Similarity	NPC40728
0.835	Intermediate Similarity	NPC112457
0.8333	Intermediate Similarity	NPC477130
0.8333	Intermediate Similarity	NPC477129
0.8333	Intermediate Similarity	NPC109376
0.8315	Intermediate Similarity	NPC473685
0.8298	Intermediate Similarity	NPC284561
0.8265	Intermediate Similarity	NPC204054
0.8265	Intermediate Similarity	NPC257726
0.8252	Intermediate Similarity	NPC470024
0.8252	Intermediate Similarity	NPC224660
0.8235	Intermediate Similarity	NPC218158
0.8229	Intermediate Similarity	NPC475657
0.8229	Intermediate Similarity	NPC471571
0.8211	Intermediate Similarity	NPC220454
0.8211	Intermediate Similarity	NPC469403
0.8211	Intermediate Similarity	NPC212679
0.8211	Intermediate Similarity	NPC469595
0.8191	Intermediate Similarity	NPC196407
0.8172	Intermediate Similarity	NPC244174
0.8172	Intermediate Similarity	NPC118266
0.8152	Intermediate Similarity	NPC471367
0.8148	Intermediate Similarity	NPC23046
0.8137	Intermediate Similarity	NPC222161
0.8125	Intermediate Similarity	NPC474631
0.8119	Intermediate Similarity	NPC31058
0.8119	Intermediate Similarity	NPC469606
0.8119	Intermediate Similarity	NPC273005
0.8105	Intermediate Similarity	NPC470819
0.81	Intermediate Similarity	NPC228251
0.81	Intermediate Similarity	NPC477971
0.81	Intermediate Similarity	NPC477972
0.81	Intermediate Similarity	NPC161527
0.81	Intermediate Similarity	NPC477968
0.81	Intermediate Similarity	NPC219285
0.81	Intermediate Similarity	NPC20113
0.8095	Intermediate Similarity	NPC316708
0.8065	Intermediate Similarity	NPC472442
0.8061	Intermediate Similarity	NPC473369
0.8043	Intermediate Similarity	NPC472440
0.8037	Intermediate Similarity	NPC474410
0.8037	Intermediate Similarity	NPC157441
0.8037	Intermediate Similarity	NPC293658
0.8021	Intermediate Similarity	NPC471371
0.8021	Intermediate Similarity	NPC471370
0.8021	Intermediate Similarity	NPC470817
0.8021	Intermediate Similarity	NPC469372
0.8019	Intermediate Similarity	NPC470026
0.8019	Intermediate Similarity	NPC17791
0.8	Intermediate Similarity	NPC69713
0.7979	Intermediate Similarity	NPC471368
0.7979	Intermediate Similarity	NPC471369
0.7959	Intermediate Similarity	NPC477722
0.7957	Intermediate Similarity	NPC71626
0.7944	Intermediate Similarity	NPC12046
0.7944	Intermediate Similarity	NPC470025
0.7944	Intermediate Similarity	NPC328074
0.7944	Intermediate Similarity	NPC317460
0.7944	Intermediate Similarity	NPC194951
0.7944	Intermediate Similarity	NPC321272
0.7941	Intermediate Similarity	NPC134077
0.7938	Intermediate Similarity	NPC165904
0.7938	Intermediate Similarity	NPC179517
0.7921	Intermediate Similarity	NPC470761
0.7921	Intermediate Similarity	NPC477720
0.7921	Intermediate Similarity	NPC473219
0.7917	Intermediate Similarity	NPC174765
0.7912	Intermediate Similarity	NPC195424
0.79	Intermediate Similarity	NPC96597
0.79	Intermediate Similarity	NPC239547
0.79	Intermediate Similarity	NPC91197
0.79	Intermediate Similarity	NPC125551
0.79	Intermediate Similarity	NPC309503
0.79	Intermediate Similarity	NPC155319
0.7895	Intermediate Similarity	NPC102640
0.7885	Intermediate Similarity	NPC469607
0.7885	Intermediate Similarity	NPC127790
0.7885	Intermediate Similarity	NPC127609
0.7879	Intermediate Similarity	NPC230347
0.7879	Intermediate Similarity	NPC275310
0.7879	Intermediate Similarity	NPC286612
0.7872	Intermediate Similarity	NPC119001
0.787	Intermediate Similarity	NPC470027
0.7864	Intermediate Similarity	NPC120009
0.7864	Intermediate Similarity	NPC254202
0.7857	Intermediate Similarity	NPC166346
0.7843	Intermediate Similarity	NPC473384
0.7843	Intermediate Similarity	NPC63249
0.7838	Intermediate Similarity	NPC474179
0.7838	Intermediate Similarity	NPC475834
0.7835	Intermediate Similarity	NPC328935
0.7835	Intermediate Similarity	NPC327183
0.7822	Intermediate Similarity	NPC473154
0.7812	Intermediate Similarity	NPC24816
0.7812	Intermediate Similarity	NPC473151
0.7812	Intermediate Similarity	NPC226863
0.7812	Intermediate Similarity	NPC263079
0.781	Intermediate Similarity	NPC293512
0.78	Intermediate Similarity	NPC73858
0.7789	Intermediate Similarity	NPC220478
0.7789	Intermediate Similarity	NPC102996
0.7788	Intermediate Similarity	NPC476763
0.7788	Intermediate Similarity	NPC476764
0.7788	Intermediate Similarity	NPC470297
0.7778	Intermediate Similarity	NPC250075
0.7778	Intermediate Similarity	NPC38830
0.7767	Intermediate Similarity	NPC235369
0.7767	Intermediate Similarity	NPC471993
0.7757	Intermediate Similarity	NPC235014
0.7757	Intermediate Similarity	NPC83005
0.7755	Intermediate Similarity	NPC477574
0.7755	Intermediate Similarity	NPC141831
0.7748	Intermediate Similarity	NPC473828
0.7748	Intermediate Similarity	NPC473617
0.7748	Intermediate Similarity	NPC475913
0.7745	Intermediate Similarity	NPC54705
0.7736	Intermediate Similarity	NPC219900
0.7736	Intermediate Similarity	NPC392
0.7736	Intermediate Similarity	NPC177524
0.7723	Intermediate Similarity	NPC110937
0.7723	Intermediate Similarity	NPC202705
0.7723	Intermediate Similarity	NPC76266
0.7719	Intermediate Similarity	NPC41129
0.7717	Intermediate Similarity	NPC469802
0.7714	Intermediate Similarity	NPC82251
0.7714	Intermediate Similarity	NPC476762
0.7714	Intermediate Similarity	NPC476761
0.7714	Intermediate Similarity	NPC469401
0.7714	Intermediate Similarity	NPC476760
0.7706	Intermediate Similarity	NPC469454
0.7706	Intermediate Similarity	NPC469496
0.7706	Intermediate Similarity	NPC469463
0.77	Intermediate Similarity	NPC295347
0.77	Intermediate Similarity	NPC477970
0.77	Intermediate Similarity	NPC135224
0.77	Intermediate Similarity	NPC100892
0.77	Intermediate Similarity	NPC477969
0.77	Intermediate Similarity	NPC281134
0.7699	Intermediate Similarity	NPC204731
0.7685	Intermediate Similarity	NPC304180
0.7685	Intermediate Similarity	NPC179798
0.7684	Intermediate Similarity	NPC300985
0.7684	Intermediate Similarity	NPC189311
0.7679	Intermediate Similarity	NPC122971
0.7677	Intermediate Similarity	NPC267266
0.7677	Intermediate Similarity	NPC469939
0.7677	Intermediate Similarity	NPC242069
0.7677	Intermediate Similarity	NPC99653
0.7677	Intermediate Similarity	NPC277721
0.767	Intermediate Similarity	NPC280991
0.766	Intermediate Similarity	NPC22611
0.766	Intermediate Similarity	NPC469
0.766	Intermediate Similarity	NPC193198

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 NPC311166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1191
0.2-0.3	3735
0.3-0.4	2621
0.4-0.5	896
0.5-0.6	325
0.6-0.7	191
0.7-0.8	16
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
0.7736	Intermediate Similarity	NPD6686	Approved
0.7368	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8039	Approved
0.732	Intermediate Similarity	NPD1694	Approved
0.7308	Intermediate Similarity	NPD7638	Approved
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD7639	Approved
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD6399	Phase 3
0.7157	Intermediate Similarity	NPD5778	Approved
0.7156	Intermediate Similarity	NPD6412	Phase 2
0.7094	Intermediate Similarity	NPD8515	Approved
0.7094	Intermediate Similarity	NPD8513	Phase 3
0.7094	Intermediate Similarity	NPD8516	Approved
0.7094	Intermediate Similarity	NPD8517	Approved
0.7094	Intermediate Similarity	NPD7503	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7071	Intermediate Similarity	NPD7521	Approved
0.7059	Intermediate Similarity	NPD7637	Suspended
0.703	Intermediate Similarity	NPD6051	Approved
0.6981	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6672	Approved
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD5737	Approved
0.6909	Remote Similarity	NPD6008	Approved
0.6893	Remote Similarity	NPD6411	Approved
0.6869	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7507	Approved
0.6796	Remote Similarity	NPD5207	Approved
0.6783	Remote Similarity	NPD8133	Approved
0.6762	Remote Similarity	NPD7900	Approved
0.6762	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5694	Approved
0.6731	Remote Similarity	NPD6050	Approved
0.6731	Remote Similarity	NPD5693	Phase 1
0.6726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6101	Approved
0.6696	Remote Similarity	NPD6053	Discontinued
0.6696	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7327	Approved
0.6695	Remote Similarity	NPD7328	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6639	Remote Similarity	NPD7516	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6635	Remote Similarity	NPD6698	Approved
0.6635	Remote Similarity	NPD7838	Discovery
0.6635	Remote Similarity	NPD5692	Phase 3
0.6635	Remote Similarity	NPD46	Approved
0.6629	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7736	Approved
0.6612	Remote Similarity	NPD6370	Approved
0.6606	Remote Similarity	NPD6648	Approved
0.6604	Remote Similarity	NPD7748	Approved
0.6583	Remote Similarity	NPD8294	Approved
0.6583	Remote Similarity	NPD8377	Approved
0.6579	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7902	Approved
0.6571	Remote Similarity	NPD5281	Approved
0.6571	Remote Similarity	NPD5284	Approved
0.6571	Remote Similarity	NPD7983	Approved
0.6569	Remote Similarity	NPD6098	Approved
0.6552	Remote Similarity	NPD6882	Approved
0.6542	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD1695	Approved
0.6538	Remote Similarity	NPD6673	Approved
0.6538	Remote Similarity	NPD6080	Approved
0.6535	Remote Similarity	NPD4786	Approved
0.6535	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3668	Phase 3
0.6532	Remote Similarity	NPD8293	Discontinued
0.6532	Remote Similarity	NPD8074	Phase 3
0.6529	Remote Similarity	NPD8378	Approved
0.6529	Remote Similarity	NPD8380	Approved
0.6529	Remote Similarity	NPD8335	Approved
0.6529	Remote Similarity	NPD8379	Approved
0.6529	Remote Similarity	NPD8296	Approved
0.6522	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4250	Approved
0.6505	Remote Similarity	NPD4251	Approved
0.6504	Remote Similarity	NPD7492	Approved
0.65	Remote Similarity	NPD3667	Approved
0.6481	Remote Similarity	NPD7839	Suspended
0.6471	Remote Similarity	NPD6009	Approved
0.6471	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7115	Discovery
0.6457	Remote Similarity	NPD7260	Phase 2
0.6452	Remote Similarity	NPD6616	Approved
0.6446	Remote Similarity	NPD6054	Approved
0.6436	Remote Similarity	NPD6695	Phase 3
0.6423	Remote Similarity	NPD8328	Phase 3
0.6423	Remote Similarity	NPD6067	Discontinued
0.6422	Remote Similarity	NPD6083	Phase 2
0.6422	Remote Similarity	NPD6084	Phase 2
0.6415	Remote Similarity	NPD7515	Phase 2
0.6408	Remote Similarity	NPD4249	Approved
0.64	Remote Similarity	NPD7078	Approved
0.6389	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5695	Phase 3
0.6381	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6899	Approved
0.6348	Remote Similarity	NPD6881	Approved
0.6346	Remote Similarity	NPD3573	Approved
0.6321	Remote Similarity	NPD5785	Approved
0.6316	Remote Similarity	NPD6402	Approved
0.6316	Remote Similarity	NPD7128	Approved
0.6316	Remote Similarity	NPD5739	Approved
0.6316	Remote Similarity	NPD6675	Approved
0.6311	Remote Similarity	NPD6059	Approved
0.6311	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5282	Discontinued
0.6286	Remote Similarity	NPD5208	Approved
0.6275	Remote Similarity	NPD5362	Discontinued
0.6275	Remote Similarity	NPD7154	Phase 3
0.6263	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD8034	Phase 2
0.6262	Remote Similarity	NPD8035	Phase 2
0.6261	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5697	Approved
0.626	Remote Similarity	NPD6016	Approved
0.626	Remote Similarity	NPD6015	Approved
0.625	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD5344	Discontinued
0.6239	Remote Similarity	NPD6371	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD5654	Approved
0.6239	Remote Similarity	NPD6883	Approved
0.6218	Remote Similarity	NPD4632	Approved
0.6216	Remote Similarity	NPD5696	Approved
0.6214	Remote Similarity	NPD3665	Phase 1
0.6214	Remote Similarity	NPD3133	Approved
0.6214	Remote Similarity	NPD3666	Approved
0.621	Remote Similarity	NPD5988	Approved
0.6207	Remote Similarity	NPD7320	Approved
0.6207	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6011	Approved
0.62	Remote Similarity	NPD6929	Approved
0.619	Remote Similarity	NPD7524	Approved
0.619	Remote Similarity	NPD8451	Approved
0.619	Remote Similarity	NPD7750	Discontinued
0.6186	Remote Similarity	NPD6617	Approved
0.6186	Remote Similarity	NPD6847	Approved
0.6186	Remote Similarity	NPD6650	Approved
0.6186	Remote Similarity	NPD8130	Phase 1
0.6186	Remote Similarity	NPD6869	Approved
0.6186	Remote Similarity	NPD6649	Approved
0.6182	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7829	Approved
0.616	Remote Similarity	NPD7122	Discontinued
0.616	Remote Similarity	NPD7830	Approved
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6154	Remote Similarity	NPD6373	Approved
0.6154	Remote Similarity	NPD6845	Suspended
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6372	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6147	Remote Similarity	NPD6001	Approved
0.6142	Remote Similarity	NPD8448	Approved
0.6139	Remote Similarity	NPD4821	Approved
0.6139	Remote Similarity	NPD6931	Approved
0.6139	Remote Similarity	NPD4820	Approved
0.6139	Remote Similarity	NPD4819	Approved
0.6139	Remote Similarity	NPD4822	Approved
0.6139	Remote Similarity	NPD7332	Phase 2
0.6139	Remote Similarity	NPD6930	Phase 2
0.6139	Remote Similarity	NPD7514	Phase 3
0.6134	Remote Similarity	NPD8297	Approved
0.6129	Remote Similarity	NPD8444	Approved
0.6126	Remote Similarity	NPD5959	Approved
0.6124	Remote Similarity	NPD6914	Discontinued
0.6122	Remote Similarity	NPD8264	Approved
0.6121	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD6079	Approved
0.61	Remote Similarity	NPD4268	Approved
0.61	Remote Similarity	NPD4271	Approved
0.61	Remote Similarity	NPD7145	Approved
0.6095	Remote Similarity	NPD4519	Discontinued
0.6095	Remote Similarity	NPD4623	Approved
0.6095	Remote Similarity	NPD3618	Phase 1
0.6083	Remote Similarity	NPD7094	Approved
0.6083	Remote Similarity	NPD6858	Approved
0.6078	Remote Similarity	NPD6902	Approved
0.6075	Remote Similarity	NPD5328	Approved
0.605	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6319	Approved
0.6032	Remote Similarity	NPD7604	Phase 2
0.602	Remote Similarity	NPD5733	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