NPASS Compound

Structure

NPC475815 OpenBabel07101718302D 26 28 0 0 1 0 0 0 0 0999 V2000 1.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7944 3.5696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7944 3.5696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0532 2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6037 5.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1554 3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 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 1.7071 1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1213 3.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 3.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1554 3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 1 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 3.8284 3.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8284 3.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3461 1.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8966 4.3461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 1 1 1 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 2 1 1 0 0 0 14 22 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 15 1 6 0 0 0 21 22 1 0 0 0 0 22 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.2
Volume:	382.741
LogP:	4.625
LogD:	4.396
LogS:	-5.94
# Rotatable Bonds:	6
TPSA:	36.92
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	3.215
Fsp3:	0.455
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:	-4.741
MDCK Permeability:	5.587526175077073e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.677

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.119
Plasma Protein Binding (PPB):	84.29706573486328%
Volume Distribution (VD):	3.235
Pgp-substrate:	7.19579553604126%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.814
CYP2C19-substrate:	0.897
CYP2C9-inhibitor:	0.824
CYP2C9-substrate:	0.808
CYP2D6-inhibitor:	0.069
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	10.866
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.431
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.122
Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.06
Skin Sensitization:	0.532
Carcinogencity:	0.075
Eye Corrosion:	0.006
Eye Irritation:	0.055
Respiratory Toxicity:	0.093

Download Data

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

Natural Product: NPC475815

Natural Product ID:	NPC475815
*Common Name:**	Cinbalansan
IUPAC Name:	4-[(1R,2S,3R,4S)-2-(3,4-dimethoxyphenyl)-3,4-dimethylcyclobutyl]-1,2-dimethoxybenzene
Synonyms:	Cinbalansan
Standard InCHIKey:	IOTXFXWARGNLEJ-DQEHQXCCSA-N
Standard InCHI:	InChI=1S/C22H28O4/c1-13-14(2)22(16-8-10-18(24-4)20(12-16)26-6)21(13)15-7-9-17(23-3)19(11-15)25-5/h7-14,21-22H,1-6H3/t13-,14+,21-,22+
SMILES:	CC1C(C(C1C2=CC(=C(C=C2)OC)OC)C3=CC(=C(C=C3)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516595
PubChem CID:	44570800
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003419] Cyclobutane lignans

*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
NPO18777	Endiandra anthropophagorum	Species	Lauraceae	Eukaryota	n.a.	Australian	n.a.	PMID[17583952]
NPO18777	Endiandra anthropophagorum	Species	Lauraceae	Eukaryota	n.a.	Australian rainforest	n.a.	PMID[19138858]
NPO18777	Endiandra anthropophagorum	Species	Lauraceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	34.0	%	PMID[567428]

☑ 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 NPC475815 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	465
0.1-0.2	1879
0.2-0.3	5201
0.3-0.4	13918
0.4-0.5	3886
0.5-0.6	8468
0.6-0.7	6493
0.7-0.8	2074
0.8-0.85	245
0.85-0.9	51
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473264
0.9813	High Similarity	NPC165106
0.9633	High Similarity	NPC47194
0.9545	High Similarity	NPC81067
0.9545	High Similarity	NPC9341
0.9386	High Similarity	NPC160380
0.9386	High Similarity	NPC38996
0.9375	High Similarity	NPC474040
0.9224	High Similarity	NPC470887
0.9211	High Similarity	NPC242885
0.9211	High Similarity	NPC232316
0.9211	High Similarity	NPC95614
0.9211	High Similarity	NPC344161
0.9211	High Similarity	NPC56214
0.9211	High Similarity	NPC117780
0.9211	High Similarity	NPC227217
0.9211	High Similarity	NPC165133
0.9123	High Similarity	NPC281298
0.9123	High Similarity	NPC310338
0.9052	High Similarity	NPC172676
0.9052	High Similarity	NPC126935
0.9052	High Similarity	NPC80241
0.9052	High Similarity	NPC57268
0.9052	High Similarity	NPC301641
0.9052	High Similarity	NPC65933
0.9052	High Similarity	NPC312713
0.9052	High Similarity	NPC216929
0.9052	High Similarity	NPC477886
0.9035	High Similarity	NPC474214
0.9035	High Similarity	NPC470626
0.8974	High Similarity	NPC85488
0.8972	High Similarity	NPC292792
0.8957	High Similarity	NPC475961
0.8957	High Similarity	NPC474320
0.8957	High Similarity	NPC254625
0.8947	High Similarity	NPC293619
0.8898	High Similarity	NPC317769
0.8898	High Similarity	NPC280704
0.8898	High Similarity	NPC31344
0.8824	High Similarity	NPC34902
0.8824	High Similarity	NPC18449
0.8824	High Similarity	NPC121783
0.8814	High Similarity	NPC30462
0.8803	High Similarity	NPC207613
0.8793	High Similarity	NPC15805
0.8785	High Similarity	NPC12714
0.8785	High Similarity	NPC310905
0.876	High Similarity	NPC189248
0.876	High Similarity	NPC202904
0.875	High Similarity	NPC29008
0.875	High Similarity	NPC228771
0.875	High Similarity	NPC17348
0.875	High Similarity	NPC266705
0.875	High Similarity	NPC9067
0.875	High Similarity	NPC148627
0.8739	High Similarity	NPC249788
0.8729	High Similarity	NPC184651
0.8729	High Similarity	NPC470212
0.8729	High Similarity	NPC473853
0.8729	High Similarity	NPC324571
0.8729	High Similarity	NPC262156
0.8729	High Similarity	NPC113865
0.8729	High Similarity	NPC312675
0.8729	High Similarity	NPC54872
0.8729	High Similarity	NPC343720
0.8696	High Similarity	NPC123948
0.8678	High Similarity	NPC50683
0.8678	High Similarity	NPC112571
0.8678	High Similarity	NPC285725
0.8678	High Similarity	NPC274356
0.8678	High Similarity	NPC206882
0.8661	High Similarity	NPC137685
0.8644	High Similarity	NPC472596
0.8621	High Similarity	NPC280001
0.8621	High Similarity	NPC185738
0.8611	High Similarity	NPC300166
0.8607	High Similarity	NPC165045
0.8607	High Similarity	NPC127587
0.8607	High Similarity	NPC177167
0.8607	High Similarity	NPC98745
0.8607	High Similarity	NPC5428
0.8607	High Similarity	NPC223807
0.8607	High Similarity	NPC158737
0.8607	High Similarity	NPC118533
0.8583	High Similarity	NPC282496
0.8583	High Similarity	NPC471693
0.8583	High Similarity	NPC233526
0.8559	High Similarity	NPC258171
0.8547	High Similarity	NPC277460
0.8537	High Similarity	NPC307050
0.8537	High Similarity	NPC277458
0.8537	High Similarity	NPC282703
0.8537	High Similarity	NPC11258
0.8537	High Similarity	NPC45774
0.8537	High Similarity	NPC158471
0.8537	High Similarity	NPC128208
0.8537	High Similarity	NPC21867
0.8537	High Similarity	NPC165128
0.8537	High Similarity	NPC82862
0.8537	High Similarity	NPC129570
0.8537	High Similarity	NPC470084
0.8537	High Similarity	NPC184733
0.8537	High Similarity	NPC222127
0.8537	High Similarity	NPC57119
0.8537	High Similarity	NPC226862
0.8525	High Similarity	NPC88297
0.8525	High Similarity	NPC76451
0.8525	High Similarity	NPC213711
0.8525	High Similarity	NPC186845
0.8525	High Similarity	NPC9891
0.8525	High Similarity	NPC40352
0.85	High Similarity	NPC261661
0.85	High Similarity	NPC71090
0.8496	Intermediate Similarity	NPC475852
0.8482	Intermediate Similarity	NPC201959
0.8482	Intermediate Similarity	NPC75440
0.8475	Intermediate Similarity	NPC311595
0.8475	Intermediate Similarity	NPC24474
0.8468	Intermediate Similarity	NPC476748
0.8468	Intermediate Similarity	NPC475875
0.8462	Intermediate Similarity	NPC86947
0.8462	Intermediate Similarity	NPC164386
0.8455	Intermediate Similarity	NPC106511
0.8455	Intermediate Similarity	NPC8050
0.8455	Intermediate Similarity	NPC241224
0.8455	Intermediate Similarity	NPC473093
0.8455	Intermediate Similarity	NPC21563
0.8455	Intermediate Similarity	NPC473092
0.8443	Intermediate Similarity	NPC298757
0.8443	Intermediate Similarity	NPC193544
0.8443	Intermediate Similarity	NPC203133
0.8443	Intermediate Similarity	NPC17943
0.8443	Intermediate Similarity	NPC221077
0.8443	Intermediate Similarity	NPC53305
0.8443	Intermediate Similarity	NPC57490
0.8443	Intermediate Similarity	NPC208950
0.8443	Intermediate Similarity	NPC475169
0.8443	Intermediate Similarity	NPC233410
0.8443	Intermediate Similarity	NPC472093
0.8443	Intermediate Similarity	NPC105925
0.8443	Intermediate Similarity	NPC257589
0.8443	Intermediate Similarity	NPC251855
0.8443	Intermediate Similarity	NPC117214
0.8443	Intermediate Similarity	NPC116907
0.8435	Intermediate Similarity	NPC204120
0.843	Intermediate Similarity	NPC228922
0.843	Intermediate Similarity	NPC197757
0.843	Intermediate Similarity	NPC279379
0.8421	Intermediate Similarity	NPC173746
0.8421	Intermediate Similarity	NPC156840
0.8421	Intermediate Similarity	NPC8547
0.8421	Intermediate Similarity	NPC257124
0.8417	Intermediate Similarity	NPC127389
0.8417	Intermediate Similarity	NPC290451
0.8403	Intermediate Similarity	NPC474565
0.84	Intermediate Similarity	NPC173308
0.84	Intermediate Similarity	NPC224157
0.84	Intermediate Similarity	NPC145305
0.84	Intermediate Similarity	NPC257582
0.84	Intermediate Similarity	NPC233224
0.84	Intermediate Similarity	NPC275950
0.84	Intermediate Similarity	NPC241522
0.84	Intermediate Similarity	NPC174495
0.84	Intermediate Similarity	NPC153739
0.84	Intermediate Similarity	NPC42300
0.84	Intermediate Similarity	NPC242807
0.84	Intermediate Similarity	NPC92164
0.84	Intermediate Similarity	NPC271208
0.84	Intermediate Similarity	NPC187998
0.84	Intermediate Similarity	NPC181079
0.84	Intermediate Similarity	NPC192687
0.84	Intermediate Similarity	NPC77040
0.84	Intermediate Similarity	NPC64201
0.8393	Intermediate Similarity	NPC227894
0.8387	Intermediate Similarity	NPC207702
0.8387	Intermediate Similarity	NPC281864
0.8387	Intermediate Similarity	NPC149008
0.8387	Intermediate Similarity	NPC328682
0.8387	Intermediate Similarity	NPC54321
0.8387	Intermediate Similarity	NPC283114
0.8376	Intermediate Similarity	NPC268317
0.8374	Intermediate Similarity	NPC17837
0.8374	Intermediate Similarity	NPC92207
0.8374	Intermediate Similarity	NPC223953
0.8374	Intermediate Similarity	NPC127937
0.8374	Intermediate Similarity	NPC304630
0.8361	Intermediate Similarity	NPC109822
0.8361	Intermediate Similarity	NPC293701
0.8361	Intermediate Similarity	NPC48990
0.8361	Intermediate Similarity	NPC114901
0.8361	Intermediate Similarity	NPC94276
0.8348	Intermediate Similarity	NPC165646
0.8347	Intermediate Similarity	NPC41562
0.8333	Intermediate Similarity	NPC31279
0.8333	Intermediate Similarity	NPC14007
0.8333	Intermediate Similarity	NPC158079
0.8333	Intermediate Similarity	NPC470161
0.8333	Intermediate Similarity	NPC82111
0.8333	Intermediate Similarity	NPC40432
0.8333	Intermediate Similarity	NPC232275

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 NPC475815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	1022
0.2-0.3	1446
0.3-0.4	2775
0.4-0.5	1830
0.5-0.6	1022
0.6-0.7	539
0.7-0.8	123
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9813	High Similarity	NPD5283	Phase 1
0.8621	High Similarity	NPD5536	Phase 2
0.8421	Intermediate Similarity	NPD228	Approved
0.84	Intermediate Similarity	NPD5109	Approved
0.84	Intermediate Similarity	NPD5110	Phase 2
0.84	Intermediate Similarity	NPD5111	Phase 2
0.8246	Intermediate Similarity	NPD3021	Approved
0.8246	Intermediate Similarity	NPD3022	Approved
0.8197	Intermediate Similarity	NPD2981	Phase 2
0.8175	Intermediate Similarity	NPD3027	Phase 3
0.813	Intermediate Similarity	NPD2983	Phase 2
0.813	Intermediate Similarity	NPD2982	Phase 2
0.813	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD3705	Approved
0.8087	Intermediate Similarity	NPD5451	Approved
0.8077	Intermediate Similarity	NPD6896	Approved
0.8077	Intermediate Similarity	NPD6895	Approved
0.8016	Intermediate Similarity	NPD3018	Phase 2
0.8	Intermediate Similarity	NPD2684	Approved
0.7984	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD7157	Approved
0.7953	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD3657	Discovery
0.792	Intermediate Similarity	NPD2922	Phase 1
0.7881	Intermediate Similarity	NPD5535	Approved
0.7881	Intermediate Similarity	NPD7843	Approved
0.7879	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD1651	Approved
0.7846	Intermediate Similarity	NPD3620	Phase 2
0.7846	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5718	Phase 2
0.7768	Intermediate Similarity	NPD3020	Approved
0.7724	Intermediate Similarity	NPD1357	Approved
0.771	Intermediate Similarity	NPD4060	Phase 1
0.7704	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD5327	Phase 3
0.768	Intermediate Similarity	NPD1281	Approved
0.7661	Intermediate Similarity	NPD2667	Approved
0.7661	Intermediate Similarity	NPD2668	Approved
0.7615	Intermediate Similarity	NPD7095	Approved
0.7609	Intermediate Similarity	NPD7124	Phase 2
0.7607	Intermediate Similarity	NPD1358	Approved
0.7591	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD4110	Phase 3
0.7591	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD6331	Phase 2
0.7581	Intermediate Similarity	NPD5691	Approved
0.7581	Intermediate Similarity	NPD5585	Approved
0.7574	Intermediate Similarity	NPD2808	Discontinued
0.7559	Intermediate Similarity	NPD1669	Approved
0.7541	Intermediate Similarity	NPD6387	Discontinued
0.7538	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD3134	Approved
0.752	Intermediate Similarity	NPD6516	Phase 2
0.752	Intermediate Similarity	NPD5846	Approved
0.752	Intermediate Similarity	NPD4626	Approved
0.7519	Intermediate Similarity	NPD4624	Approved
0.75	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD2859	Approved
0.75	Intermediate Similarity	NPD2860	Approved
0.7481	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD3596	Phase 2
0.748	Intermediate Similarity	NPD2230	Approved
0.748	Intermediate Similarity	NPD2232	Approved
0.748	Intermediate Similarity	NPD2233	Approved
0.7462	Intermediate Similarity	NPD2861	Phase 2
0.7462	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD3847	Discontinued
0.7444	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1613	Approved
0.7444	Intermediate Similarity	NPD2979	Phase 3
0.7426	Intermediate Similarity	NPD2161	Phase 2
0.7426	Intermediate Similarity	NPD2438	Suspended
0.7426	Intermediate Similarity	NPD3539	Phase 1
0.7411	Intermediate Similarity	NPD2933	Approved
0.7411	Intermediate Similarity	NPD2934	Approved
0.741	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6111	Discontinued
0.7405	Intermediate Similarity	NPD4908	Phase 1
0.7398	Intermediate Similarity	NPD709	Approved
0.7398	Intermediate Similarity	NPD6671	Approved
0.7391	Intermediate Similarity	NPD3060	Approved
0.7391	Intermediate Similarity	NPD4162	Approved
0.7388	Intermediate Similarity	NPD6355	Discontinued
0.7385	Intermediate Similarity	NPD6584	Phase 3
0.7381	Intermediate Similarity	NPD17	Approved
0.7376	Intermediate Similarity	NPD4584	Approved
0.7372	Intermediate Similarity	NPD3540	Phase 1
0.7368	Intermediate Similarity	NPD2674	Phase 3
0.7368	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1876	Approved
0.7361	Intermediate Similarity	NPD6875	Approved
0.7361	Intermediate Similarity	NPD6876	Approved
0.736	Intermediate Similarity	NPD6581	Approved
0.736	Intermediate Similarity	NPD6580	Approved
0.7355	Intermediate Similarity	NPD1137	Approved
0.7355	Intermediate Similarity	NPD1139	Approved
0.7344	Intermediate Similarity	NPD3972	Approved
0.7333	Intermediate Similarity	NPD2653	Approved
0.7313	Intermediate Similarity	NPD1558	Phase 1
0.7305	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3444	Approved
0.7302	Intermediate Similarity	NPD3445	Approved
0.7302	Intermediate Similarity	NPD3443	Approved
0.7295	Intermediate Similarity	NPD1138	Approved
0.7293	Intermediate Similarity	NPD3144	Approved
0.7293	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3145	Approved
0.7287	Intermediate Similarity	NPD4359	Approved
0.7286	Intermediate Similarity	NPD5241	Discontinued
0.7266	Intermediate Similarity	NPD1610	Phase 2
0.7266	Intermediate Similarity	NPD5177	Phase 3
0.7266	Intermediate Similarity	NPD1611	Approved
0.7266	Intermediate Similarity	NPD4237	Approved
0.7266	Intermediate Similarity	NPD4236	Phase 3
0.7259	Intermediate Similarity	NPD5735	Approved
0.7258	Intermediate Similarity	NPD2557	Approved
0.7252	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7905	Discontinued
0.7246	Intermediate Similarity	NPD1375	Discontinued
0.7244	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3028	Approved
0.7231	Intermediate Similarity	NPD8651	Approved
0.7231	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD968	Approved
0.7226	Intermediate Similarity	NPD4108	Discontinued
0.7222	Intermediate Similarity	NPD1182	Approved
0.7209	Intermediate Similarity	NPD1608	Approved
0.7209	Intermediate Similarity	NPD1840	Phase 2
0.7206	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6873	Phase 2
0.7185	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD4140	Approved
0.7174	Intermediate Similarity	NPD2531	Phase 2
0.7167	Intermediate Similarity	NPD290	Approved
0.7164	Intermediate Similarity	NPD6798	Discontinued
0.7154	Intermediate Similarity	NPD6582	Phase 2
0.7154	Intermediate Similarity	NPD821	Approved
0.7154	Intermediate Similarity	NPD6583	Phase 3
0.7153	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6031	Approved
0.7153	Intermediate Similarity	NPD6030	Approved
0.7153	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7123	Intermediate Similarity	NPD7028	Phase 2
0.7113	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3531	Approved
0.7111	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3532	Approved
0.7111	Intermediate Similarity	NPD3530	Approved
0.7111	Intermediate Similarity	NPD8032	Phase 2
0.7111	Intermediate Similarity	NPD7265	Discontinued
0.7105	Intermediate Similarity	NPD9296	Approved
0.7105	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2883	Discontinued
0.7097	Intermediate Similarity	NPD1241	Discontinued
0.7083	Intermediate Similarity	NPD52	Approved
0.7083	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7526	Approved
0.708	Intermediate Similarity	NPD4097	Suspended
0.708	Intermediate Similarity	NPD6353	Approved
0.7077	Intermediate Similarity	NPD2231	Phase 2
0.7077	Intermediate Similarity	NPD2235	Phase 2
0.7075	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7110	Phase 1
0.7068	Intermediate Similarity	NPD9494	Approved
0.7059	Intermediate Similarity	NPD3110	Approved
0.7059	Intermediate Similarity	NPD3109	Approved
0.7059	Intermediate Similarity	NPD2238	Phase 2
0.7055	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4017	Approved
0.7055	Intermediate Similarity	NPD4005	Discontinued
0.7054	Intermediate Similarity	NPD3496	Discontinued
0.7045	Intermediate Similarity	NPD4098	Discontinued
0.7034	Intermediate Similarity	NPD291	Approved
0.7031	Intermediate Similarity	NPD3049	Approved
0.7029	Intermediate Similarity	NPD4536	Approved
0.7029	Intermediate Similarity	NPD4538	Approved
0.7029	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD37	Approved
0.7027	Intermediate Similarity	NPD7298	Approved
0.7023	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6542	Approved
0.7023	Intermediate Similarity	NPD6540	Phase 3
0.7023	Intermediate Similarity	NPD6539	Approved
0.7023	Intermediate Similarity	NPD4749	Approved
0.7023	Intermediate Similarity	NPD6543	Approved
0.7023	Intermediate Similarity	NPD3685	Discontinued
0.7021	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4123	Phase 3
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5763	Approved
0.6992	Remote Similarity	NPD2798	Approved
0.6986	Remote Similarity	NPD4210	Discontinued

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