NPASS Compound

Structure

NPC86257 OpenBabel07101718182D 42 47 0 0 1 0 0 0 0 0999 V2000 -7.1870 -1.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7216 -2.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 35 1 0 0 0 0 9 12 1 0 0 0 0 9 26 2 0 0 0 0 10 13 2 0 0 0 0 10 26 1 0 0 0 0 11 14 2 0 0 0 0 11 26 1 0 0 0 0 12 27 2 0 0 0 0 13 27 1 0 0 0 0 14 33 1 0 0 0 0 15 19 1 0 0 0 0 15 29 2 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 17 21 1 0 0 0 0 17 30 1 0 0 0 0 18 22 1 0 0 0 0 18 32 1 0 0 0 0 19 36 1 0 0 0 0 20 38 1 0 0 0 0 21 39 1 0 0 0 0 22 37 1 0 0 0 0 23 24 1 0 0 0 0 23 34 1 0 0 0 0 24 36 1 0 0 0 0 25 31 1 0 0 0 0 25 34 1 0 0 0 0 27 40 1 0 0 0 0 28 35 1 0 0 0 0 28 37 1 6 0 0 0 29 38 1 0 0 0 0 29 39 1 0 0 0 0 30 37 1 6 0 0 0 30 38 1 0 0 0 0 31 36 1 1 0 0 0 31 39 1 0 0 0 0 32 35 1 0 0 0 0 32 42 1 1 0 0 0 33 41 2 0 0 0 0 33 42 1 0 0 0 0 36 5 1 6 0 0 0 37 6 1 6 0 0 0 38 7 1 6 0 0 0 39 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.42
Volume:	642.313
LogP:	7.975
LogD:	5.89
LogS:	-6.811
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.223
Synthetic Accessibility Score:	4.873
Fsp3:	0.718
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.255
MDCK Permeability:	1.8948861907119863e-05
Pgp-inhibitor:	0.954
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.672
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	100.86975860595703%
Volume Distribution (VD):	1.614
Pgp-substrate:	2.1659505367279053%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.398
CYP2C19-inhibitor:	0.174
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.419
CYP2D6-substrate:	0.812
CYP3A4-inhibitor:	0.27
CYP3A4-substrate:	0.425

ADMET: Excretion

Clearance (CL):	4.819
Half-life (T1/2):	0.105

ADMET: Toxicity

hERG Blockers:	0.222
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.959
Carcinogencity:	0.007
Eye Corrosion:	0.045
Eye Irritation:	0.609
Respiratory Toxicity:	0.752

Download Data

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

Natural Product: NPC86257

Natural Product ID:	NPC86257
*Common Name:**	3-Alpha-Z-Coumaroyltaraxerol
IUPAC Name:	[(3R,4aR,6aR,6aS,8aR,12aR,14aR,14bR)-4,4,6a,6a,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-yl] (Z)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	FZPSABBXYRSWMG-SYLDJCCYSA-N
Standard InCHI:	InChI=1S/C39H56O3/c1-34(2)23-24-36(5)19-15-29-38(7)20-16-28-35(3,4)32(42-33(41)14-11-26-9-12-27(40)13-10-26)18-22-37(28,6)30(38)17-21-39(29,8)31(36)25-34/h9-15,28,30-32,40H,16-25H2,1-8H3/b14-11-/t28-,30+,31+,32+,36-,37-,38-,39+/m0/s1
SMILES:	CC1(C)CC[C@]2(C)CC=C3[C@]4(C)CC[C@H]5C(C)(C)[C@@H](CC[C@]5(C)[C@H]4CC[C@@]3(C)[C@@H]2C1)OC(=O)/C=Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452896
PubChem CID:	10076796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15165157]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	20.0	ug.mL-1	PMID[492831]

☑ 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 NPC86257 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	284
0.1-0.2	1387
0.2-0.3	2507
0.3-0.4	6171
0.4-0.5	9756
0.5-0.6	13164
0.6-0.7	8489
0.7-0.8	796
0.8-0.85	59
0.85-0.9	41
0.9-0.95	39
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9531	High Similarity	NPC477874
0.9531	High Similarity	NPC173569
0.9457	High Similarity	NPC249817
0.9453	High Similarity	NPC11266
0.9385	High Similarity	NPC475482
0.9385	High Similarity	NPC216940
0.9385	High Similarity	NPC22676
0.9385	High Similarity	NPC198621
0.9313	High Similarity	NPC182249
0.9274	High Similarity	NPC265413
0.9274	High Similarity	NPC10154
0.9242	High Similarity	NPC271494
0.9242	High Similarity	NPC155192
0.9242	High Similarity	NPC473591
0.9173	High Similarity	NPC27518
0.9173	High Similarity	NPC304110
0.9173	High Similarity	NPC172311
0.9167	High Similarity	NPC139243
0.9167	High Similarity	NPC248287
0.9167	High Similarity	NPC116742
0.9167	High Similarity	NPC234548
0.9098	High Similarity	NPC470616
0.9098	High Similarity	NPC470617
0.9077	High Similarity	NPC475627
0.9077	High Similarity	NPC475346
0.9077	High Similarity	NPC475457
0.9077	High Similarity	NPC18982
0.9037	High Similarity	NPC477873
0.9037	High Similarity	NPC469447
0.903	High Similarity	NPC473612
0.903	High Similarity	NPC472801
0.8971	High Similarity	NPC25491
0.8968	High Similarity	NPC474532
0.8963	High Similarity	NPC35212
0.896	High Similarity	NPC478058
0.8905	High Similarity	NPC307205
0.8905	High Similarity	NPC53520
0.8897	High Similarity	NPC252133
0.8897	High Similarity	NPC310621
0.8897	High Similarity	NPC235557
0.8832	High Similarity	NPC26045
0.8769	High Similarity	NPC288290
0.875	High Similarity	NPC137416
0.8714	High Similarity	NPC477483
0.8714	High Similarity	NPC325032
0.8705	High Similarity	NPC8102
0.8705	High Similarity	NPC66894
0.8657	High Similarity	NPC472804
0.8592	High Similarity	NPC327962
0.8582	High Similarity	NPC194970
0.8531	High Similarity	NPC118033
0.8529	High Similarity	NPC471152
0.8521	High Similarity	NPC279442
0.8472	Intermediate Similarity	NPC473773
0.8472	Intermediate Similarity	NPC475579
0.8462	Intermediate Similarity	NPC145527
0.8462	Intermediate Similarity	NPC470619
0.8462	Intermediate Similarity	NPC208785
0.8462	Intermediate Similarity	NPC470618
0.8443	Intermediate Similarity	NPC139946
0.8403	Intermediate Similarity	NPC475454
0.8403	Intermediate Similarity	NPC475311
0.8403	Intermediate Similarity	NPC473680
0.8403	Intermediate Similarity	NPC473579
0.8382	Intermediate Similarity	NPC43353
0.8369	Intermediate Similarity	NPC235195
0.8369	Intermediate Similarity	NPC19862
0.8369	Intermediate Similarity	NPC280717
0.8369	Intermediate Similarity	NPC271607
0.8357	Intermediate Similarity	NPC204644
0.8333	Intermediate Similarity	NPC76032
0.8333	Intermediate Similarity	NPC132723
0.8322	Intermediate Similarity	NPC96930
0.8322	Intermediate Similarity	NPC32017
0.8288	Intermediate Similarity	NPC205392
0.8288	Intermediate Similarity	NPC105942
0.8281	Intermediate Similarity	NPC135467
0.8281	Intermediate Similarity	NPC260832
0.8273	Intermediate Similarity	NPC471875
0.8264	Intermediate Similarity	NPC298647
0.8264	Intermediate Similarity	NPC292206
0.8264	Intermediate Similarity	NPC473719
0.8264	Intermediate Similarity	NPC273358
0.8258	Intermediate Similarity	NPC473220
0.8258	Intermediate Similarity	NPC470753
0.8209	Intermediate Similarity	NPC30174
0.8209	Intermediate Similarity	NPC131684
0.8203	Intermediate Similarity	NPC93071
0.8203	Intermediate Similarity	NPC126002
0.8189	Intermediate Similarity	NPC122117
0.8188	Intermediate Similarity	NPC476699
0.8182	Intermediate Similarity	NPC470765
0.8182	Intermediate Similarity	NPC320734
0.8176	Intermediate Similarity	NPC472807
0.8169	Intermediate Similarity	NPC96447
0.812	Intermediate Similarity	NPC171007
0.812	Intermediate Similarity	NPC190849
0.8116	Intermediate Similarity	NPC279463
0.8088	Intermediate Similarity	NPC18798
0.808	Intermediate Similarity	NPC228425
0.8065	Intermediate Similarity	NPC183700
0.8062	Intermediate Similarity	NPC42657
0.8047	Intermediate Similarity	NPC477136
0.8031	Intermediate Similarity	NPC147179
0.8029	Intermediate Similarity	NPC165612
0.8028	Intermediate Similarity	NPC20631
0.8028	Intermediate Similarity	NPC93640
0.8015	Intermediate Similarity	NPC249425
0.8	Intermediate Similarity	NPC176590
0.8	Intermediate Similarity	NPC472938
0.8	Intermediate Similarity	NPC472937
0.8	Intermediate Similarity	NPC472936
0.8	Intermediate Similarity	NPC477208
0.7984	Intermediate Similarity	NPC471954
0.7984	Intermediate Similarity	NPC75272
0.7972	Intermediate Similarity	NPC477209
0.7971	Intermediate Similarity	NPC476282
0.7969	Intermediate Similarity	NPC470820
0.7969	Intermediate Similarity	NPC308828
0.7969	Intermediate Similarity	NPC219112
0.7969	Intermediate Similarity	NPC477137
0.7969	Intermediate Similarity	NPC308311
0.7969	Intermediate Similarity	NPC38893
0.7969	Intermediate Similarity	NPC471668
0.7967	Intermediate Similarity	NPC260952
0.7959	Intermediate Similarity	NPC162569
0.7959	Intermediate Similarity	NPC35160
0.7958	Intermediate Similarity	NPC138149
0.7956	Intermediate Similarity	NPC153019
0.7955	Intermediate Similarity	NPC121168
0.7953	Intermediate Similarity	NPC268160
0.7953	Intermediate Similarity	NPC41851
0.7941	Intermediate Similarity	NPC117899
0.7939	Intermediate Similarity	NPC470848
0.7939	Intermediate Similarity	NPC470849
0.7917	Intermediate Similarity	NPC474599
0.7917	Intermediate Similarity	NPC477207
0.7917	Intermediate Similarity	NPC471876
0.791	Intermediate Similarity	NPC275576
0.7908	Intermediate Similarity	NPC266365
0.7905	Intermediate Similarity	NPC77310
0.7903	Intermediate Similarity	NPC470039
0.7903	Intermediate Similarity	NPC206341
0.7899	Intermediate Similarity	NPC321086
0.7899	Intermediate Similarity	NPC289624
0.7899	Intermediate Similarity	NPC27578
0.7895	Intermediate Similarity	NPC12824
0.7895	Intermediate Similarity	NPC472373
0.7891	Intermediate Similarity	NPC35797
0.7891	Intermediate Similarity	NPC477206
0.7891	Intermediate Similarity	NPC192948
0.7887	Intermediate Similarity	NPC106055
0.7887	Intermediate Similarity	NPC79372
0.7887	Intermediate Similarity	NPC164743
0.7887	Intermediate Similarity	NPC110699
0.7883	Intermediate Similarity	NPC472793
0.7879	Intermediate Similarity	NPC249340
0.7879	Intermediate Similarity	NPC162935
0.7872	Intermediate Similarity	NPC306365
0.7868	Intermediate Similarity	NPC47288
0.7868	Intermediate Similarity	NPC229894
0.7868	Intermediate Similarity	NPC193203
0.7862	Intermediate Similarity	NPC43716
0.7862	Intermediate Similarity	NPC101255
0.7862	Intermediate Similarity	NPC475719
0.7857	Intermediate Similarity	NPC35630
0.7852	Intermediate Similarity	NPC35341
0.7852	Intermediate Similarity	NPC71610
0.7852	Intermediate Similarity	NPC283508
0.7852	Intermediate Similarity	NPC169913
0.7852	Intermediate Similarity	NPC48671
0.7846	Intermediate Similarity	NPC471671
0.7846	Intermediate Similarity	NPC164649
0.7846	Intermediate Similarity	NPC203124
0.7846	Intermediate Similarity	NPC48342
0.7846	Intermediate Similarity	NPC309434
0.7846	Intermediate Similarity	NPC469609
0.7843	Intermediate Similarity	NPC269668
0.7842	Intermediate Similarity	NPC185777
0.7842	Intermediate Similarity	NPC49742
0.7842	Intermediate Similarity	NPC211352
0.7842	Intermediate Similarity	NPC203486
0.7838	Intermediate Similarity	NPC472939
0.7838	Intermediate Similarity	NPC87630
0.7838	Intermediate Similarity	NPC116292
0.7838	Intermediate Similarity	NPC267469
0.7838	Intermediate Similarity	NPC179128
0.7832	Intermediate Similarity	NPC470035
0.7829	Intermediate Similarity	NPC137496
0.7829	Intermediate Similarity	NPC154511
0.7829	Intermediate Similarity	NPC471936
0.7829	Intermediate Similarity	NPC469663
0.7829	Intermediate Similarity	NPC92
0.7829	Intermediate Similarity	NPC247858
0.7829	Intermediate Similarity	NPC474358
0.7829	Intermediate Similarity	NPC257540
0.7829	Intermediate Similarity	NPC474387
0.7826	Intermediate Similarity	NPC473047
0.7826	Intermediate Similarity	NPC243305
0.782	Intermediate Similarity	NPC71094

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 NPC86257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	889
0.2-0.3	1377
0.3-0.4	2690
0.4-0.5	2220
0.5-0.6	1324
0.6-0.7	377
0.7-0.8	18
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD8166	Discontinued
0.8333	Intermediate Similarity	NPD5736	Approved
0.8088	Intermediate Similarity	NPD6663	Approved
0.8028	Intermediate Similarity	NPD7003	Approved
0.7899	Intermediate Similarity	NPD4140	Approved
0.7846	Intermediate Similarity	NPD3091	Approved
0.7755	Intermediate Similarity	NPD6273	Approved
0.7727	Intermediate Similarity	NPD4626	Approved
0.7718	Intermediate Similarity	NPD7458	Discontinued
0.7652	Intermediate Similarity	NPD5691	Approved
0.7612	Intermediate Similarity	NPD3092	Approved
0.7594	Intermediate Similarity	NPD3019	Approved
0.7594	Intermediate Similarity	NPD2932	Approved
0.7518	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD5327	Phase 3
0.7483	Intermediate Similarity	NPD7097	Phase 1
0.7463	Intermediate Similarity	NPD3095	Discontinued
0.7452	Intermediate Similarity	NPD8127	Discontinued
0.7447	Intermediate Similarity	NPD8032	Phase 2
0.7398	Intermediate Similarity	NPD3020	Approved
0.7391	Intermediate Similarity	NPD3094	Phase 2
0.7343	Intermediate Similarity	NPD5735	Approved
0.7333	Intermediate Similarity	NPD4059	Approved
0.7329	Intermediate Similarity	NPD7266	Discontinued
0.7323	Intermediate Similarity	NPD3134	Approved
0.7305	Intermediate Similarity	NPD7095	Approved
0.7305	Intermediate Similarity	NPD7008	Discontinued
0.7297	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6353	Approved
0.7273	Intermediate Similarity	NPD3620	Phase 2
0.7273	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3764	Approved
0.7218	Intermediate Similarity	NPD4198	Discontinued
0.7214	Intermediate Similarity	NPD4624	Approved
0.7213	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7236	Approved
0.7194	Intermediate Similarity	NPD1283	Approved
0.7181	Intermediate Similarity	NPD4628	Phase 3
0.7154	Intermediate Similarity	NPD2860	Approved
0.7154	Intermediate Similarity	NPD2859	Approved
0.7153	Intermediate Similarity	NPD3496	Discontinued
0.7143	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD5404	Approved
0.7133	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5535	Approved
0.7121	Intermediate Similarity	NPD7635	Approved
0.7113	Intermediate Similarity	NPD4908	Phase 1
0.7105	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6355	Discontinued
0.7095	Intermediate Similarity	NPD5762	Approved
0.7095	Intermediate Similarity	NPD5763	Approved
0.7092	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7768	Phase 2
0.7075	Intermediate Similarity	NPD7742	Approved
0.7075	Intermediate Similarity	NPD7743	Approved
0.7073	Intermediate Similarity	NPD2934	Approved
0.7073	Intermediate Similarity	NPD2933	Approved
0.7068	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7741	Discontinued
0.7059	Intermediate Similarity	NPD9545	Approved
0.7055	Intermediate Similarity	NPD4097	Suspended
0.7055	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2861	Phase 2
0.7029	Intermediate Similarity	NPD3023	Approved
0.7029	Intermediate Similarity	NPD3026	Approved
0.7027	Intermediate Similarity	NPD2935	Discontinued
0.7023	Intermediate Similarity	NPD3022	Approved
0.7023	Intermediate Similarity	NPD3021	Approved
0.702	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8131	Suspended
0.7016	Intermediate Similarity	NPD1809	Phase 2
0.7015	Intermediate Similarity	NPD2629	Approved
0.7015	Intermediate Similarity	NPD5951	Approved
0.7014	Intermediate Similarity	NPD6798	Discontinued
0.7007	Intermediate Similarity	NPD5585	Approved
0.7007	Intermediate Similarity	NPD3025	Approved
0.7007	Intermediate Similarity	NPD3024	Approved
0.7	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1358	Approved
0.7	Intermediate Similarity	NPD2342	Discontinued
0.6993	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6858	Approved
0.6992	Remote Similarity	NPD7094	Approved
0.6986	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5124	Phase 1
0.6978	Remote Similarity	NPD1281	Approved
0.6978	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7239	Suspended
0.6963	Remote Similarity	NPD7157	Approved
0.696	Remote Similarity	NPD288	Approved
0.6959	Remote Similarity	NPD2799	Discontinued
0.6959	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1778	Approved
0.6954	Remote Similarity	NPD4110	Phase 3
0.6954	Remote Similarity	NPD3750	Approved
0.6954	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.695	Remote Similarity	NPD8651	Approved
0.694	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7037	Approved
0.6929	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2979	Phase 3
0.6918	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3268	Approved
0.6894	Remote Similarity	NPD4750	Phase 3
0.6884	Remote Similarity	NPD4093	Discontinued
0.688	Remote Similarity	NPD844	Approved
0.6875	Remote Similarity	NPD2606	Approved
0.6875	Remote Similarity	NPD2605	Approved
0.6864	Remote Similarity	NPD8313	Approved
0.6864	Remote Similarity	NPD8312	Approved
0.6857	Remote Similarity	NPD1610	Phase 2
0.6857	Remote Similarity	NPD422	Phase 1
0.6857	Remote Similarity	NPD1201	Approved
0.6855	Remote Similarity	NPD845	Approved
0.6855	Remote Similarity	NPD7819	Suspended
0.6853	Remote Similarity	NPD6584	Phase 3
0.6846	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6671	Approved
0.6835	Remote Similarity	NPD1751	Approved
0.6828	Remote Similarity	NPD5155	Approved
0.6828	Remote Similarity	NPD5156	Approved
0.6818	Remote Similarity	NPD7041	Phase 2
0.6818	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3972	Approved
0.68	Remote Similarity	NPD6100	Approved
0.68	Remote Similarity	NPD4477	Approved
0.68	Remote Similarity	NPD4476	Approved
0.68	Remote Similarity	NPD2438	Suspended
0.68	Remote Similarity	NPD6099	Approved
0.6797	Remote Similarity	NPD6190	Approved
0.6795	Remote Similarity	NPD5699	Approved
0.6788	Remote Similarity	NPD9493	Approved
0.6788	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3847	Discontinued
0.6784	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1470	Approved
0.6783	Remote Similarity	NPD1164	Approved
0.6781	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7119	Phase 2
0.6772	Remote Similarity	NPD7028	Phase 2
0.6769	Remote Similarity	NPD5909	Discontinued
0.6763	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD1651	Approved
0.6761	Remote Similarity	NPD6583	Phase 3
0.6761	Remote Similarity	NPD6582	Phase 2
0.6761	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4359	Approved
0.6761	Remote Similarity	NPD4749	Approved
0.6759	Remote Similarity	NPD3594	Approved
0.6759	Remote Similarity	NPD3595	Approved
0.6755	Remote Similarity	NPD2346	Discontinued
0.6753	Remote Similarity	NPD6666	Approved
0.6753	Remote Similarity	NPD6667	Approved
0.675	Remote Similarity	NPD8455	Phase 2
0.6744	Remote Similarity	NPD8150	Discontinued
0.6741	Remote Similarity	NPD7843	Approved
0.6738	Remote Similarity	NPD1611	Approved
0.6736	Remote Similarity	NPD2798	Approved
0.6735	Remote Similarity	NPD6233	Phase 2
0.6735	Remote Similarity	NPD7961	Discontinued
0.6731	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6677	Suspended
0.6728	Remote Similarity	NPD7833	Phase 2
0.6728	Remote Similarity	NPD7831	Phase 2
0.6728	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2286	Discontinued
0.6713	Remote Similarity	NPD6696	Suspended
0.6712	Remote Similarity	NPD4625	Phase 3
0.6711	Remote Similarity	NPD4534	Discontinued
0.671	Remote Similarity	NPD7390	Discontinued
0.6707	Remote Similarity	NPD7228	Approved
0.6692	Remote Similarity	NPD6647	Phase 2
0.6692	Remote Similarity	NPD2684	Approved
0.6691	Remote Similarity	NPD2228	Approved
0.6691	Remote Similarity	NPD5283	Phase 1
0.6691	Remote Similarity	NPD2234	Approved
0.6691	Remote Similarity	NPD1241	Discontinued
0.6691	Remote Similarity	NPD1894	Discontinued
0.6691	Remote Similarity	NPD2229	Approved
0.669	Remote Similarity	NPD2230	Approved
0.669	Remote Similarity	NPD3635	Approved
0.669	Remote Similarity	NPD4208	Discontinued
0.669	Remote Similarity	NPD2233	Approved
0.669	Remote Similarity	NPD3636	Approved
0.669	Remote Similarity	NPD3637	Approved
0.669	Remote Similarity	NPD1608	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