NPASS Compound

Structure

CID297057 OpenBabel06191716102D 32 37 0 0 1 0 0 0 0 0999 V2000 -3.2864 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1296 -2.5601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8161 -1.5864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3754 1.2337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3294 -2.2534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7768 0.5871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1577 -0.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5646 -1.4708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2317 -0.3119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4078 -1.5218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9729 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4432 -2.5601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9729 -1.0996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4432 -0.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9552 -2.5389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8676 0.4420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1296 0.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2864 -2.0733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1577 -1.5864 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8166 -0.5303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1296 -0.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2864 -1.0996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8161 -0.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5999 -1.0996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8161 0.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5999 -2.0733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6593 -1.0996 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7567 -0.6128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2317 -1.8873 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6593 0.8478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7567 -2.5601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 17 2 0 0 0 0 11 25 1 0 0 0 0 12 18 2 0 0 0 0 12 26 1 0 0 0 0 13 21 2 0 0 0 0 13 23 1 0 0 0 0 14 22 2 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 29 1 0 0 0 0 16 20 1 0 0 0 0 16 30 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 29 1 6 0 0 0 20 30 1 6 0 0 0 21 22 1 0 0 0 0 23 25 2 0 0 0 0 23 27 1 0 0 0 0 24 26 2 0 0 0 0 24 28 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 27 29 1 1 0 0 0 28 30 1 1 0 0 0 29 5 1 6 0 0 0 30 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.29
Volume:	477.859
LogP:	7.19
LogD:	4.967
LogS:	-6.752
# Rotatable Bonds:	3
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.528
Synthetic Accessibility Score:	4.557
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.254
MDCK Permeability:	1.4354486665979493e-05
Pgp-inhibitor:	0.458
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	101.15558624267578%
Volume Distribution (VD):	1.738
Pgp-substrate:	1.965981125831604%

ADMET: Metabolism

CYP1A2-inhibitor:	0.119
CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.323
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.241
CYP2C9-substrate:	0.77
CYP2D6-inhibitor:	0.751
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.574
CYP3A4-substrate:	0.799

ADMET: Excretion

Clearance (CL):	5.811
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.281
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.293
AMES Toxicity:	0.196
Rat Oral Acute Toxicity:	0.184
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.958
Carcinogencity:	0.037
Eye Corrosion:	0.004
Eye Irritation:	0.931
Respiratory Toxicity:	0.789

Download Data

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

Natural Product: NPC297057

Natural Product ID:	NPC297057
*Common Name:**	Laurebiphenyl
IUPAC Name:	2-[(1S,2R,5R)-1,2-dimethyl-2-bicyclo[3.1.0]hexanyl]-4-[5-[(1S,2R,5R)-1,2-dimethyl-2-bicyclo[3.1.0]hexanyl]-4-hydroxy-2-methylphenyl]-5-methylphenol
Synonyms:	Laurebiphenyl
Standard InCHIKey:	XNIZFYLMUVNEOT-MUVIMXQCSA-N
Standard InCHI:	InChI=1S/C30H38O2/c1-17-11-25(31)23(27(3)9-7-19-15-29(19,27)5)13-21(17)22-14-24(26(32)12-18(22)2)28(4)10-8-20-16-30(20,28)6/h11-14,19-20,31-32H,7-10,15-16H2,1-6H3/t19-,20-,27+,28+,29+,30+/m1/s1
SMILES:	Cc1cc(O)c(cc1c1cc(c(cc1C)O)[C@]1(C)CC[C@H]2[C@]1(C)C2)[C@]1(C)CC[C@H]2[C@]1(C)C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463338
PubChem CID:	11532074
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO19220	Laurencia nidifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)81142-5]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974618]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27536968]
NPO19220	Laurencia nidifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19220	Laurencia nidifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19220	Laurencia nidifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1.68	ug.mL-1	PMID[522394]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	1.22	ug.mL-1	PMID[522394]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	1.91	ug.mL-1	PMID[522394]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	1.77	ug.mL-1	PMID[522394]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1.61	ug.mL-1	PMID[522394]

☑ 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 NPC297057 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	453
0.1-0.2	1916
0.2-0.3	3800
0.3-0.4	12355
0.4-0.5	10957
0.5-0.6	10371
0.6-0.7	2541
0.7-0.8	291
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8729	High Similarity	NPC195922
0.8655	High Similarity	NPC469719
0.8632	High Similarity	NPC151537
0.8632	High Similarity	NPC176279
0.8632	High Similarity	NPC260323
0.8621	High Similarity	NPC58865
0.8609	High Similarity	NPC151477
0.8583	High Similarity	NPC154511
0.8583	High Similarity	NPC137496
0.8583	High Similarity	NPC257540
0.8583	High Similarity	NPC471668
0.8583	High Similarity	NPC474358
0.8583	High Similarity	NPC474387
0.8583	High Similarity	NPC247858
0.8559	High Similarity	NPC250323
0.8559	High Similarity	NPC46940
0.8534	High Similarity	NPC64586
0.85	High Similarity	NPC35797
0.85	High Similarity	NPC192948
0.8487	Intermediate Similarity	NPC715
0.8475	Intermediate Similarity	NPC95716
0.8475	Intermediate Similarity	NPC322753
0.8435	Intermediate Similarity	NPC117115
0.843	Intermediate Similarity	NPC308311
0.843	Intermediate Similarity	NPC38893
0.843	Intermediate Similarity	NPC477137
0.839	Intermediate Similarity	NPC141782
0.839	Intermediate Similarity	NPC13482
0.8374	Intermediate Similarity	NPC126002
0.8374	Intermediate Similarity	NPC93071
0.8362	Intermediate Similarity	NPC21594
0.8361	Intermediate Similarity	NPC304510
0.8361	Intermediate Similarity	NPC172219
0.8361	Intermediate Similarity	NPC477136
0.8306	Intermediate Similarity	NPC68339
0.8293	Intermediate Similarity	NPC471671
0.8279	Intermediate Similarity	NPC219112
0.8264	Intermediate Similarity	NPC268160
0.825	Intermediate Similarity	NPC228425
0.8235	Intermediate Similarity	NPC296683
0.8235	Intermediate Similarity	NPC132720
0.8226	Intermediate Similarity	NPC258366
0.8226	Intermediate Similarity	NPC473974
0.8226	Intermediate Similarity	NPC79933
0.8226	Intermediate Similarity	NPC151197
0.8226	Intermediate Similarity	NPC31296
0.8226	Intermediate Similarity	NPC469644
0.822	Intermediate Similarity	NPC11554
0.8197	Intermediate Similarity	NPC147179
0.819	Intermediate Similarity	NPC254965
0.819	Intermediate Similarity	NPC327811
0.819	Intermediate Similarity	NPC238696
0.816	Intermediate Similarity	NPC99734
0.8151	Intermediate Similarity	NPC314187
0.8145	Intermediate Similarity	NPC154030
0.8145	Intermediate Similarity	NPC164649
0.8145	Intermediate Similarity	NPC48342
0.813	Intermediate Similarity	NPC308828
0.813	Intermediate Similarity	NPC92
0.813	Intermediate Similarity	NPC469663
0.812	Intermediate Similarity	NPC219286
0.812	Intermediate Similarity	NPC99557
0.812	Intermediate Similarity	NPC138942
0.811	Intermediate Similarity	NPC176208
0.8103	Intermediate Similarity	NPC168829
0.8099	Intermediate Similarity	NPC471179
0.8099	Intermediate Similarity	NPC62867
0.8099	Intermediate Similarity	NPC177962
0.8095	Intermediate Similarity	NPC328504
0.8095	Intermediate Similarity	NPC241001
0.8095	Intermediate Similarity	NPC32322
0.8095	Intermediate Similarity	NPC259703
0.8087	Intermediate Similarity	NPC211885
0.8065	Intermediate Similarity	NPC16030
0.8065	Intermediate Similarity	NPC299180
0.8051	Intermediate Similarity	NPC310456
0.8034	Intermediate Similarity	NPC288411
0.8033	Intermediate Similarity	NPC322239
0.8033	Intermediate Similarity	NPC263753
0.8031	Intermediate Similarity	NPC249340
0.8031	Intermediate Similarity	NPC154696
0.8031	Intermediate Similarity	NPC162935
0.8017	Intermediate Similarity	NPC77772
0.8017	Intermediate Similarity	NPC470770
0.8017	Intermediate Similarity	NPC252105
0.8017	Intermediate Similarity	NPC469912
0.8017	Intermediate Similarity	NPC266937
0.8016	Intermediate Similarity	NPC135467
0.8016	Intermediate Similarity	NPC318552
0.8016	Intermediate Similarity	NPC190501
0.8016	Intermediate Similarity	NPC260832
0.8	Intermediate Similarity	NPC206
0.8	Intermediate Similarity	NPC469609
0.7984	Intermediate Similarity	NPC115808
0.7984	Intermediate Similarity	NPC141001
0.7983	Intermediate Similarity	NPC320439
0.7969	Intermediate Similarity	NPC71094
0.7969	Intermediate Similarity	NPC121168
0.7969	Intermediate Similarity	NPC11250
0.7967	Intermediate Similarity	NPC107240
0.7931	Intermediate Similarity	NPC225506
0.7923	Intermediate Similarity	NPC124030
0.792	Intermediate Similarity	NPC470760
0.7917	Intermediate Similarity	NPC306295
0.791	Intermediate Similarity	NPC85595
0.7907	Intermediate Similarity	NPC471187
0.7899	Intermediate Similarity	NPC54765
0.7899	Intermediate Similarity	NPC271274
0.7891	Intermediate Similarity	NPC77569
0.7891	Intermediate Similarity	NPC142198
0.7886	Intermediate Similarity	NPC317869
0.7886	Intermediate Similarity	NPC117846
0.7881	Intermediate Similarity	NPC272029
0.7874	Intermediate Similarity	NPC478121
0.7874	Intermediate Similarity	NPC475245
0.7846	Intermediate Similarity	NPC97578
0.7846	Intermediate Similarity	NPC181334
0.7845	Intermediate Similarity	NPC33675
0.7845	Intermediate Similarity	NPC252821
0.7845	Intermediate Similarity	NPC299762
0.7845	Intermediate Similarity	NPC92730
0.7845	Intermediate Similarity	NPC122005
0.7829	Intermediate Similarity	NPC321402
0.7823	Intermediate Similarity	NPC471534
0.7823	Intermediate Similarity	NPC249270
0.782	Intermediate Similarity	NPC288290
0.782	Intermediate Similarity	NPC276238
0.7815	Intermediate Similarity	NPC47284
0.7812	Intermediate Similarity	NPC129176
0.7805	Intermediate Similarity	NPC166995
0.7803	Intermediate Similarity	NPC108164
0.7803	Intermediate Similarity	NPC471077
0.7797	Intermediate Similarity	NPC269212
0.7795	Intermediate Similarity	NPC176893
0.7787	Intermediate Similarity	NPC224870
0.7786	Intermediate Similarity	NPC137750
0.7778	Intermediate Similarity	NPC72729
0.7769	Intermediate Similarity	NPC95344
0.7769	Intermediate Similarity	NPC53567
0.7769	Intermediate Similarity	NPC262365
0.776	Intermediate Similarity	NPC246760
0.776	Intermediate Similarity	NPC84999
0.7759	Intermediate Similarity	NPC79241
0.7759	Intermediate Similarity	NPC77492
0.7759	Intermediate Similarity	NPC225464
0.7759	Intermediate Similarity	NPC32674
0.7759	Intermediate Similarity	NPC156313
0.7759	Intermediate Similarity	NPC6597
0.7752	Intermediate Similarity	NPC39029
0.7752	Intermediate Similarity	NPC253627
0.775	Intermediate Similarity	NPC155072
0.775	Intermediate Similarity	NPC53740
0.7742	Intermediate Similarity	NPC321589
0.7742	Intermediate Similarity	NPC23804
0.7739	Intermediate Similarity	NPC144682
0.7739	Intermediate Similarity	NPC222146
0.7734	Intermediate Similarity	NPC103916
0.7727	Intermediate Similarity	NPC269598
0.7727	Intermediate Similarity	NPC9292
0.7727	Intermediate Similarity	NPC321822
0.7727	Intermediate Similarity	NPC145659
0.7727	Intermediate Similarity	NPC43000
0.7727	Intermediate Similarity	NPC325294
0.7727	Intermediate Similarity	NPC100414
0.7724	Intermediate Similarity	NPC224527
0.7724	Intermediate Similarity	NPC476632
0.7724	Intermediate Similarity	NPC225679
0.7724	Intermediate Similarity	NPC4493
0.7724	Intermediate Similarity	NPC165770
0.7717	Intermediate Similarity	NPC328694
0.7712	Intermediate Similarity	NPC477685
0.771	Intermediate Similarity	NPC224342
0.771	Intermediate Similarity	NPC15127
0.7698	Intermediate Similarity	NPC261973
0.7692	Intermediate Similarity	NPC120172
0.7692	Intermediate Similarity	NPC152946
0.7692	Intermediate Similarity	NPC471794
0.7692	Intermediate Similarity	NPC478058
0.7674	Intermediate Similarity	NPC474175
0.7672	Intermediate Similarity	NPC216520
0.7672	Intermediate Similarity	NPC82664
0.7672	Intermediate Similarity	NPC292730
0.7672	Intermediate Similarity	NPC132271
0.7672	Intermediate Similarity	NPC473388
0.7672	Intermediate Similarity	NPC312132
0.7672	Intermediate Similarity	NPC202986
0.7672	Intermediate Similarity	NPC259512
0.7669	Intermediate Similarity	NPC72667
0.7669	Intermediate Similarity	NPC78364
0.7669	Intermediate Similarity	NPC69424
0.7669	Intermediate Similarity	NPC19432
0.7669	Intermediate Similarity	NPC84672
0.7669	Intermediate Similarity	NPC176130
0.7661	Intermediate Similarity	NPC43525
0.7661	Intermediate Similarity	NPC302371
0.7656	Intermediate Similarity	NPC42657
0.7652	Intermediate Similarity	NPC76119
0.7652	Intermediate Similarity	NPC4286
0.7647	Intermediate Similarity	NPC233827
0.7647	Intermediate Similarity	NPC168393

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 NPC297057 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	990
0.2-0.3	1561
0.3-0.4	3254
0.4-0.5	1965
0.5-0.6	847
0.6-0.7	143
0.7-0.8	23
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
0.8403	Intermediate Similarity	NPD7635	Approved
0.816	Intermediate Similarity	NPD4059	Approved
0.8145	Intermediate Similarity	NPD3091	Approved
0.8016	Intermediate Similarity	NPD2932	Approved
0.8016	Intermediate Similarity	NPD3019	Approved
0.7983	Intermediate Similarity	NPD2342	Discontinued
0.7891	Intermediate Similarity	NPD3092	Approved
0.7845	Intermediate Similarity	NPD3020	Approved
0.7739	Intermediate Similarity	NPD1809	Phase 2
0.7734	Intermediate Similarity	NPD3095	Discontinued
0.7704	Intermediate Similarity	NPD6663	Approved
0.7672	Intermediate Similarity	NPD288	Approved
0.7669	Intermediate Similarity	NPD5736	Approved
0.7652	Intermediate Similarity	NPD3094	Phase 2
0.7586	Intermediate Similarity	NPD2859	Approved
0.7586	Intermediate Similarity	NPD844	Approved
0.7586	Intermediate Similarity	NPD2860	Approved
0.7561	Intermediate Similarity	NPD4750	Phase 3
0.7561	Intermediate Similarity	NPD3021	Approved
0.7561	Intermediate Similarity	NPD3022	Approved
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2934	Approved
0.75	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2933	Approved
0.7479	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4624	Approved
0.7462	Intermediate Similarity	NPD2286	Discontinued
0.7422	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD845	Approved
0.741	Intermediate Similarity	NPD6353	Approved
0.7405	Intermediate Similarity	NPD3026	Approved
0.7405	Intermediate Similarity	NPD3023	Approved
0.7385	Intermediate Similarity	NPD3024	Approved
0.7385	Intermediate Similarity	NPD3025	Approved
0.7338	Intermediate Similarity	NPD5735	Approved
0.7328	Intermediate Similarity	NPD1751	Approved
0.7313	Intermediate Similarity	NPD6696	Suspended
0.7302	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4097	Suspended
0.7266	Intermediate Similarity	NPD3620	Phase 2
0.7266	Intermediate Similarity	NPD497	Approved
0.7266	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD4093	Discontinued
0.7239	Intermediate Similarity	NPD5327	Phase 3
0.7197	Intermediate Similarity	NPD4589	Approved
0.7197	Intermediate Similarity	NPD4626	Approved
0.7188	Intermediate Similarity	NPD496	Approved
0.7188	Intermediate Similarity	NPD498	Approved
0.7188	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD495	Approved
0.7183	Intermediate Similarity	NPD7743	Approved
0.7183	Intermediate Similarity	NPD7742	Approved
0.7174	Intermediate Similarity	NPD4625	Phase 3
0.708	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2195	Approved
0.708	Intermediate Similarity	NPD2194	Approved
0.7073	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1283	Approved
0.705	Intermediate Similarity	NPD5156	Approved
0.705	Intermediate Similarity	NPD5155	Approved
0.7045	Intermediate Similarity	NPD7330	Discontinued
0.7045	Intermediate Similarity	NPD5304	Approved
0.7045	Intermediate Similarity	NPD5303	Approved
0.7029	Intermediate Similarity	NPD3636	Approved
0.7029	Intermediate Similarity	NPD3637	Approved
0.7029	Intermediate Similarity	NPD2861	Phase 2
0.7029	Intermediate Similarity	NPD3635	Approved
0.7023	Intermediate Similarity	NPD7340	Approved
0.7021	Intermediate Similarity	NPD4140	Approved
0.7021	Intermediate Similarity	NPD4060	Phase 1
0.7008	Intermediate Similarity	NPD1792	Phase 2
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6992	Remote Similarity	NPD1651	Approved
0.6978	Remote Similarity	NPD2606	Approved
0.6978	Remote Similarity	NPD2605	Approved
0.6923	Remote Similarity	NPD2228	Approved
0.6923	Remote Similarity	NPD2157	Approved
0.6923	Remote Similarity	NPD2229	Approved
0.6923	Remote Similarity	NPD2234	Approved
0.6911	Remote Similarity	NPD1242	Phase 1
0.6892	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3638	Discontinued
0.6866	Remote Similarity	NPD5691	Approved
0.6866	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3594	Approved
0.6857	Remote Similarity	NPD3595	Approved
0.6838	Remote Similarity	NPD1281	Approved
0.6838	Remote Similarity	NPD1201	Approved
0.6838	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD8032	Phase 2
0.6824	Remote Similarity	NPD7003	Approved
0.6818	Remote Similarity	NPD6671	Approved
0.6794	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1398	Phase 1
0.6791	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5406	Approved
0.6781	Remote Similarity	NPD5404	Approved
0.6781	Remote Similarity	NPD5408	Approved
0.6781	Remote Similarity	NPD5405	Approved
0.6772	Remote Similarity	NPD1444	Approved
0.6772	Remote Similarity	NPD1445	Approved
0.6765	Remote Similarity	NPD3143	Discontinued
0.6741	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1669	Approved
0.6739	Remote Similarity	NPD4749	Approved
0.6735	Remote Similarity	NPD5763	Approved
0.6735	Remote Similarity	NPD5762	Approved
0.6724	Remote Similarity	NPD111	Approved
0.6715	Remote Similarity	NPD1611	Approved
0.6712	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD709	Approved
0.6689	Remote Similarity	NPD7390	Discontinued
0.6667	Remote Similarity	NPD3070	Discontinued
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD8131	Suspended
0.6667	Remote Similarity	NPD7741	Discontinued
0.6667	Remote Similarity	NPD5283	Phase 1
0.6667	Remote Similarity	NPD6100	Approved
0.6645	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3645	Discontinued
0.6644	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1470	Approved
0.6642	Remote Similarity	NPD7636	Approved
0.664	Remote Similarity	NPD3028	Approved
0.6622	Remote Similarity	NPD4726	Approved
0.6622	Remote Similarity	NPD4721	Approved
0.6622	Remote Similarity	NPD4725	Approved
0.6621	Remote Similarity	NPD3657	Discovery
0.6579	Remote Similarity	NPD2421	Approved
0.6579	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7041	Phase 2
0.6579	Remote Similarity	NPD2420	Approved
0.6552	Remote Similarity	NPD2979	Phase 3
0.6547	Remote Similarity	NPD2232	Approved
0.6547	Remote Similarity	NPD2233	Approved
0.6547	Remote Similarity	NPD2230	Approved
0.6535	Remote Similarity	NPD9500	Approved
0.6533	Remote Similarity	NPD2211	Approved
0.6533	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2209	Approved
0.6528	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1164	Approved
0.6522	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6049	Phase 2
0.6504	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4908	Phase 1
0.65	Remote Similarity	NPD7831	Phase 2
0.65	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7833	Phase 2
0.6494	Remote Similarity	NPD6090	Discontinued
0.6494	Remote Similarity	NPD6273	Approved
0.6493	Remote Similarity	NPD1791	Approved
0.6493	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD5951	Approved
0.6493	Remote Similarity	NPD1793	Approved
0.649	Remote Similarity	NPD8166	Discontinued
0.6486	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1610	Phase 2
0.6467	Remote Similarity	NPD4257	Approved
0.6467	Remote Similarity	NPD7037	Approved
0.6467	Remote Similarity	NPD4256	Phase 2
0.6458	Remote Similarity	NPD7095	Approved
0.6454	Remote Similarity	NPD1876	Approved
0.6449	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6387	Discontinued
0.6444	Remote Similarity	NPD7157	Approved
0.6438	Remote Similarity	NPD6346	Approved
0.6434	Remote Similarity	NPD1712	Approved
0.6434	Remote Similarity	NPD4212	Discontinued
0.6434	Remote Similarity	NPD4208	Discontinued
0.6414	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD1983	Approved
0.6403	Remote Similarity	NPD1981	Approved
0.6403	Remote Similarity	NPD1980	Approved
0.6397	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6355	Discontinued
0.6391	Remote Similarity	NPD228	Approved
0.6389	Remote Similarity	NPD4207	Discontinued
0.6382	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD5585	Approved
0.6376	Remote Similarity	NPD4108	Discontinued
0.6375	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6405	Approved
0.637	Remote Similarity	NPD6407	Approved
0.6364	Remote Similarity	NPD6584	Phase 3
0.6351	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7644	Approved
0.6346	Remote Similarity	NPD5699	Approved
0.6338	Remote Similarity	NPD8651	Approved
0.6338	Remote Similarity	NPD5311	Approved
0.6338	Remote Similarity	NPD5310	Approved
0.6333	Remote Similarity	NPD2935	Discontinued
0.6333	Remote Similarity	NPD2438	Suspended
0.6333	Remote Similarity	NPD2531	Phase 2
0.6331	Remote Similarity	NPD2668	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