NPASS Compound

Structure

NPC239293 OpenBabel07101719252D 44 49 0 0 1 0 0 0 0 0999 V2000 6.6968 -0.1136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0569 1.5806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7624 0.5102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.3660 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4096 1.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3878 0.8375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 1.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5981 -2.2321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1006 1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0981 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0981 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5981 -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 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -0.8660 -0.5000 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 5.7698 2.7396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0981 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 5 32 1 0 0 0 0 8 9 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 26 1 0 0 0 0 12 33 1 0 0 0 0 13 35 1 0 0 0 0 14 15 1 0 0 0 0 14 32 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 35 1 0 0 0 0 18 36 1 0 0 0 0 20 3 1 1 0 0 0 20 23 1 0 0 0 0 21 4 1 1 0 0 0 21 27 1 0 0 0 0 21 43 1 0 0 0 0 22 37 2 0 0 0 0 23 32 1 6 0 0 0 24 33 1 1 0 0 0 24 36 1 0 0 0 0 25 34 1 6 0 0 0 25 35 1 0 0 0 0 26 34 1 6 0 0 0 26 38 1 0 0 0 0 27 28 1 0 0 0 0 27 39 1 6 0 0 0 28 29 1 0 0 0 0 28 40 1 1 0 0 0 29 30 1 0 0 0 0 29 41 1 1 0 0 0 30 43 1 0 0 0 0 30 44 1 6 0 0 0 31 34 1 0 0 0 0 31 42 2 0 0 0 0 31 44 1 0 0 0 0 32 33 1 6 0 0 0 33 6 1 1 0 0 0 34 7 1 6 0 0 0 35 36 1 1 0 0 0 36 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.4
Volume:	642.286
LogP:	4.081
LogD:	3.618
LogS:	-4.857
# Rotatable Bonds:	7
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.249
Synthetic Accessibility Score:	6.188
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.311
MDCK Permeability:	2.1336960344342515e-05
Pgp-inhibitor:	0.967
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	87.6930923461914%
Volume Distribution (VD):	0.984
Pgp-substrate:	3.859661817550659%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.701
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.766
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	2.409
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.454
Human Hepatotoxicity (H-HT):	0.501
Drug-inuced Liver Injury (DILI):	0.34
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.486
Maximum Recommended Daily Dose:	0.437
Skin Sensitization:	0.917
Carcinogencity:	0.429
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC239293

Natural Product ID:	NPC239293
*Common Name:**	FHQVFDVMMIBVLK-CGXBOBFCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FHQVFDVMMIBVLK-CGXBOBFCSA-N
Standard InCHI:	InChI=1S/C36H56O8/c1-19(2)16-22(37)17-20(3)23-10-12-33(6)24-8-9-25-34(7,31(42)44-30-29(41)28(40)27(39)21(4)43-30)26(38)11-13-35(25)18-36(24,35)15-14-32(23,33)5/h16,20-21,23-30,38-41H,8-15,17-18H2,1-7H3/t20-,21+,23-,24+,25+,26+,27+,28-,29-,30+,32-,33+,34+,35-,36+/m1/s1
SMILES:	CC(=CC(=O)C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H]([C@@]2(C)C(=O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1951413
PubChem CID:	57332777
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22168134]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22206869]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		FC	=	1.1	n.a.	PMID[512781]
NPT2	Others	Unspecified		FC	=	1.0	n.a.	PMID[512781]

☑ 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 NPC239293 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	260
0.1-0.2	1678
0.2-0.3	5182
0.3-0.4	10222
0.4-0.5	10587
0.5-0.6	6216
0.6-0.7	4759
0.7-0.8	2716
0.8-0.85	953
0.85-0.9	122
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.945	High Similarity	NPC73986
0.9099	High Similarity	NPC260665
0.9091	High Similarity	NPC250481
0.9091	High Similarity	NPC285410
0.9091	High Similarity	NPC263827
0.9009	High Similarity	NPC471967
0.9009	High Similarity	NPC477253
0.9	High Similarity	NPC129340
0.8957	High Similarity	NPC470312
0.8919	High Similarity	NPC11035
0.8919	High Similarity	NPC272242
0.8919	High Similarity	NPC31839
0.8909	High Similarity	NPC265655
0.8898	High Similarity	NPC174367
0.8898	High Similarity	NPC47113
0.885	High Similarity	NPC477580
0.885	High Similarity	NPC116024
0.885	High Similarity	NPC74727
0.885	High Similarity	NPC473882
0.8839	High Similarity	NPC243572
0.8839	High Similarity	NPC470543
0.8839	High Similarity	NPC48249
0.8839	High Similarity	NPC80843
0.8839	High Similarity	NPC1046
0.8829	High Similarity	NPC154856
0.8829	High Similarity	NPC242611
0.8829	High Similarity	NPC52241
0.8829	High Similarity	NPC475317
0.8818	High Similarity	NPC195708
0.8818	High Similarity	NPC295389
0.8818	High Similarity	NPC88744
0.8807	High Similarity	NPC473199
0.8772	High Similarity	NPC244127
0.8761	High Similarity	NPC475208
0.8761	High Similarity	NPC238935
0.8761	High Similarity	NPC251309
0.8761	High Similarity	NPC146563
0.8761	High Similarity	NPC102619
0.875	High Similarity	NPC292196
0.8739	High Similarity	NPC57362
0.8739	High Similarity	NPC237503
0.8739	High Similarity	NPC246205
0.8739	High Similarity	NPC91583
0.8739	High Similarity	NPC137917
0.8739	High Similarity	NPC8431
0.8739	High Similarity	NPC51947
0.8739	High Similarity	NPC306746
0.8739	High Similarity	NPC240125
0.8739	High Similarity	NPC473844
0.8739	High Similarity	NPC218853
0.8739	High Similarity	NPC167383
0.8739	High Similarity	NPC204407
0.8727	High Similarity	NPC234160
0.8718	High Similarity	NPC202051
0.8707	High Similarity	NPC258592
0.8707	High Similarity	NPC178548
0.8704	High Similarity	NPC94919
0.8696	High Similarity	NPC477252
0.8696	High Similarity	NPC474483
0.8689	High Similarity	NPC231240
0.8684	High Similarity	NPC164389
0.8684	High Similarity	NPC475486
0.8684	High Similarity	NPC54395
0.8678	High Similarity	NPC476966
0.8673	High Similarity	NPC210420
0.8673	High Similarity	NPC233003
0.8673	High Similarity	NPC100383
0.8673	High Similarity	NPC474265
0.8673	High Similarity	NPC130427
0.8667	High Similarity	NPC471357
0.8667	High Similarity	NPC469757
0.8667	High Similarity	NPC117702
0.8667	High Similarity	NPC146456
0.8661	High Similarity	NPC199457
0.8661	High Similarity	NPC220984
0.8661	High Similarity	NPC59804
0.8661	High Similarity	NPC269095
0.8661	High Similarity	NPC476886
0.8661	High Similarity	NPC110139
0.8661	High Similarity	NPC101450
0.8661	High Similarity	NPC7870
0.8661	High Similarity	NPC274507
0.8661	High Similarity	NPC476887
0.8661	High Similarity	NPC476884
0.8661	High Similarity	NPC136877
0.8661	High Similarity	NPC56713
0.8661	High Similarity	NPC127056
0.8661	High Similarity	NPC476882
0.8661	High Similarity	NPC174679
0.8661	High Similarity	NPC29069
0.8661	High Similarity	NPC476880
0.8661	High Similarity	NPC476885
0.8661	High Similarity	NPC476883
0.8661	High Similarity	NPC78046
0.8661	High Similarity	NPC108709
0.8661	High Similarity	NPC270667
0.8661	High Similarity	NPC474589
0.8661	High Similarity	NPC164194
0.8661	High Similarity	NPC476881
0.8661	High Similarity	NPC279554
0.8661	High Similarity	NPC75747
0.8661	High Similarity	NPC90856
0.8661	High Similarity	NPC102914
0.8661	High Similarity	NPC475296
0.8661	High Similarity	NPC68419
0.8655	High Similarity	NPC177820
0.8655	High Similarity	NPC469842
0.8655	High Similarity	NPC469841
0.8655	High Similarity	NPC318135
0.8655	High Similarity	NPC30188
0.8649	High Similarity	NPC224414
0.8649	High Similarity	NPC28198
0.8649	High Similarity	NPC476123
0.8649	High Similarity	NPC38217
0.8649	High Similarity	NPC472988
0.8649	High Similarity	NPC284807
0.8649	High Similarity	NPC177246
0.8644	High Similarity	NPC471965
0.8636	High Similarity	NPC162033
0.8632	High Similarity	NPC471406
0.8632	High Similarity	NPC476150
0.8632	High Similarity	NPC476127
0.8621	High Similarity	NPC232237
0.8621	High Similarity	NPC473828
0.8621	High Similarity	NPC105800
0.8621	High Similarity	NPC473617
0.8618	High Similarity	NPC316915
0.8609	High Similarity	NPC51465
0.8609	High Similarity	NPC75287
0.8609	High Similarity	NPC137414
0.8609	High Similarity	NPC305267
0.8609	High Similarity	NPC476992
0.8609	High Similarity	NPC26626
0.8609	High Similarity	NPC291903
0.8609	High Similarity	NPC37134
0.8609	High Similarity	NPC469820
0.8609	High Similarity	NPC288205
0.8609	High Similarity	NPC469823
0.8607	High Similarity	NPC173347
0.8596	High Similarity	NPC62696
0.8596	High Similarity	NPC477944
0.8596	High Similarity	NPC293038
0.8595	High Similarity	NPC311534
0.8595	High Similarity	NPC245094
0.8584	High Similarity	NPC108748
0.8584	High Similarity	NPC269466
0.8584	High Similarity	NPC240734
0.8584	High Similarity	NPC274833
0.8584	High Similarity	NPC211798
0.8584	High Similarity	NPC204392
0.8584	High Similarity	NPC191763
0.8584	High Similarity	NPC235841
0.8584	High Similarity	NPC297208
0.8584	High Similarity	NPC179434
0.8584	High Similarity	NPC473481
0.8584	High Similarity	NPC91838
0.8584	High Similarity	NPC30397
0.8584	High Similarity	NPC1876
0.8584	High Similarity	NPC275668
0.8584	High Similarity	NPC164419
0.8583	High Similarity	NPC285091
0.8571	High Similarity	NPC154085
0.8571	High Similarity	NPC202666
0.8571	High Similarity	NPC262199
0.8571	High Similarity	NPC471964
0.8571	High Similarity	NPC125361
0.8571	High Similarity	NPC477070
0.8571	High Similarity	NPC127853
0.8571	High Similarity	NPC14617
0.8571	High Similarity	NPC471961
0.8571	High Similarity	NPC27363
0.8571	High Similarity	NPC51925
0.8571	High Similarity	NPC477069
0.8571	High Similarity	NPC118225
0.8571	High Similarity	NPC43976
0.8571	High Similarity	NPC296761
0.8559	High Similarity	NPC258815
0.8559	High Similarity	NPC241310
0.8559	High Similarity	NPC476675
0.8559	High Similarity	NPC194310
0.8559	High Similarity	NPC131841
0.8559	High Similarity	NPC473538
0.8559	High Similarity	NPC129434
0.8559	High Similarity	NPC169727
0.8559	High Similarity	NPC412
0.8559	High Similarity	NPC283849
0.8559	High Similarity	NPC47567
0.8559	High Similarity	NPC258789
0.8559	High Similarity	NPC475182
0.8547	High Similarity	NPC473401
0.8547	High Similarity	NPC207738
0.8547	High Similarity	NPC232258
0.8547	High Similarity	NPC319570
0.8545	High Similarity	NPC223741
0.8534	High Similarity	NPC191827
0.8534	High Similarity	NPC104137
0.8534	High Similarity	NPC473824
0.8534	High Similarity	NPC300419
0.8534	High Similarity	NPC69811
0.8534	High Similarity	NPC475514

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 NPC239293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1908
0.2-0.3	4010
0.3-0.4	1957
0.4-0.5	539
0.5-0.6	275
0.6-0.7	166
0.7-0.8	54
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD8328	Phase 3
0.8559	High Similarity	NPD6412	Phase 2
0.8525	High Similarity	NPD7319	Approved
0.8443	Intermediate Similarity	NPD7736	Approved
0.843	Intermediate Similarity	NPD7507	Approved
0.8246	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD8293	Discontinued
0.8167	Intermediate Similarity	NPD8294	Approved
0.8167	Intermediate Similarity	NPD8377	Approved
0.8158	Intermediate Similarity	NPD6686	Approved
0.8151	Intermediate Similarity	NPD7328	Approved
0.8151	Intermediate Similarity	NPD7327	Approved
0.812	Intermediate Similarity	NPD8133	Approved
0.8099	Intermediate Similarity	NPD8296	Approved
0.8099	Intermediate Similarity	NPD8335	Approved
0.8099	Intermediate Similarity	NPD8380	Approved
0.8099	Intermediate Similarity	NPD8378	Approved
0.8099	Intermediate Similarity	NPD8379	Approved
0.8099	Intermediate Similarity	NPD8033	Approved
0.8083	Intermediate Similarity	NPD7516	Approved
0.8067	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD6370	Approved
0.7903	Intermediate Similarity	NPD7492	Approved
0.7869	Intermediate Similarity	NPD6054	Approved
0.7869	Intermediate Similarity	NPD6319	Approved
0.7869	Intermediate Similarity	NPD6059	Approved
0.784	Intermediate Similarity	NPD6616	Approved
0.7778	Intermediate Similarity	NPD7078	Approved
0.7769	Intermediate Similarity	NPD7115	Discovery
0.7731	Intermediate Similarity	NPD6882	Approved
0.7731	Intermediate Similarity	NPD8297	Approved
0.7661	Intermediate Similarity	NPD7503	Approved
0.7661	Intermediate Similarity	NPD6016	Approved
0.7661	Intermediate Similarity	NPD6015	Approved
0.7623	Intermediate Similarity	NPD6009	Approved
0.7611	Intermediate Similarity	NPD7638	Approved
0.76	Intermediate Similarity	NPD5988	Approved
0.7568	Intermediate Similarity	NPD7748	Approved
0.7544	Intermediate Similarity	NPD7640	Approved
0.7544	Intermediate Similarity	NPD7639	Approved
0.7522	Intermediate Similarity	NPD7902	Approved
0.7521	Intermediate Similarity	NPD5739	Approved
0.7521	Intermediate Similarity	NPD7128	Approved
0.7521	Intermediate Similarity	NPD4632	Approved
0.7521	Intermediate Similarity	NPD6402	Approved
0.7521	Intermediate Similarity	NPD6675	Approved
0.7479	Intermediate Similarity	NPD6373	Approved
0.7479	Intermediate Similarity	NPD6372	Approved
0.7436	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD6067	Discontinued
0.7402	Intermediate Similarity	NPD7604	Phase 2
0.7395	Intermediate Similarity	NPD6899	Approved
0.7395	Intermediate Similarity	NPD6881	Approved
0.7395	Intermediate Similarity	NPD7320	Approved
0.7387	Intermediate Similarity	NPD7515	Phase 2
0.7387	Intermediate Similarity	NPD8035	Phase 2
0.7387	Intermediate Similarity	NPD8034	Phase 2
0.7355	Intermediate Similarity	NPD8130	Phase 1
0.7355	Intermediate Similarity	NPD6650	Approved
0.7355	Intermediate Similarity	NPD6649	Approved
0.7321	Intermediate Similarity	NPD6399	Phase 3
0.7311	Intermediate Similarity	NPD5701	Approved
0.7311	Intermediate Similarity	NPD5697	Approved
0.7308	Intermediate Similarity	NPD6033	Approved
0.7273	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD7290	Approved
0.7273	Intermediate Similarity	NPD7102	Approved
0.7273	Intermediate Similarity	NPD6883	Approved
0.7257	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7900	Approved
0.7244	Intermediate Similarity	NPD8515	Approved
0.7244	Intermediate Similarity	NPD8517	Approved
0.7244	Intermediate Similarity	NPD8516	Approved
0.7244	Intermediate Similarity	NPD8513	Phase 3
0.7227	Intermediate Similarity	NPD6008	Approved
0.7217	Intermediate Similarity	NPD6083	Phase 2
0.7217	Intermediate Similarity	NPD6084	Phase 2
0.7213	Intermediate Similarity	NPD6617	Approved
0.7213	Intermediate Similarity	NPD6869	Approved
0.7213	Intermediate Similarity	NPD6847	Approved
0.7207	Intermediate Similarity	NPD5328	Approved
0.719	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6013	Approved
0.719	Intermediate Similarity	NPD6014	Approved
0.719	Intermediate Similarity	NPD6012	Approved
0.7156	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD5983	Phase 2
0.7107	Intermediate Similarity	NPD6011	Approved
0.7107	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3618	Phase 1
0.708	Intermediate Similarity	NPD6079	Approved
0.7073	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4755	Approved
0.7043	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6336	Discontinued
0.7018	Intermediate Similarity	NPD4202	Approved
0.7009	Intermediate Similarity	NPD4225	Approved
0.6992	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7632	Discontinued
0.6964	Remote Similarity	NPD6672	Approved
0.6964	Remote Similarity	NPD5737	Approved
0.6949	Remote Similarity	NPD4700	Approved
0.6949	Remote Similarity	NPD4696	Approved
0.6949	Remote Similarity	NPD5285	Approved
0.6949	Remote Similarity	NPD5286	Approved
0.6937	Remote Similarity	NPD7521	Approved
0.6937	Remote Similarity	NPD7334	Approved
0.6937	Remote Similarity	NPD6684	Approved
0.6937	Remote Similarity	NPD6409	Approved
0.6937	Remote Similarity	NPD7146	Approved
0.6937	Remote Similarity	NPD5330	Approved
0.6917	Remote Similarity	NPD8337	Approved
0.6917	Remote Similarity	NPD8336	Approved
0.6909	Remote Similarity	NPD4786	Approved
0.6897	Remote Similarity	NPD5695	Phase 3
0.687	Remote Similarity	NPD8171	Discontinued
0.6864	Remote Similarity	NPD5696	Approved
0.6855	Remote Similarity	NPD6371	Approved
0.685	Remote Similarity	NPD6274	Approved
0.6842	Remote Similarity	NPD46	Approved
0.6842	Remote Similarity	NPD6698	Approved
0.6838	Remote Similarity	NPD5222	Approved
0.6838	Remote Similarity	NPD8338	Approved
0.6838	Remote Similarity	NPD4697	Phase 3
0.6838	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5221	Approved
0.6833	Remote Similarity	NPD5226	Approved
0.6833	Remote Similarity	NPD4633	Approved
0.6833	Remote Similarity	NPD5211	Phase 2
0.6833	Remote Similarity	NPD5224	Approved
0.6833	Remote Similarity	NPD5225	Approved
0.6822	Remote Similarity	NPD7100	Approved
0.6822	Remote Similarity	NPD7101	Approved
0.6815	Remote Similarity	NPD5956	Approved
0.6814	Remote Similarity	NPD6903	Approved
0.6803	Remote Similarity	NPD4768	Approved
0.6803	Remote Similarity	NPD4767	Approved
0.678	Remote Similarity	NPD5173	Approved
0.6777	Remote Similarity	NPD5174	Approved
0.6777	Remote Similarity	NPD5175	Approved
0.6757	Remote Similarity	NPD3666	Approved
0.6757	Remote Similarity	NPD3133	Approved
0.6757	Remote Similarity	NPD3665	Phase 1
0.6754	Remote Similarity	NPD4753	Phase 2
0.675	Remote Similarity	NPD5223	Approved
0.6748	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6335	Approved
0.6727	Remote Similarity	NPD3667	Approved
0.6721	Remote Similarity	NPD5141	Approved
0.6719	Remote Similarity	NPD6868	Approved
0.6719	Remote Similarity	NPD6940	Discontinued
0.6718	Remote Similarity	NPD6909	Approved
0.6718	Remote Similarity	NPD6908	Approved
0.6697	Remote Similarity	NPD7525	Registered
0.6694	Remote Similarity	NPD4730	Approved
0.6694	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6639	Remote Similarity	NPD4754	Approved
0.6638	Remote Similarity	NPD7637	Suspended
0.6638	Remote Similarity	NPD6411	Approved
0.6637	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6313	Approved
0.6615	Remote Similarity	NPD6314	Approved
0.6609	Remote Similarity	NPD6904	Approved
0.6609	Remote Similarity	NPD6673	Approved
0.6609	Remote Similarity	NPD6080	Approved
0.6593	Remote Similarity	NPD8074	Phase 3
0.6591	Remote Similarity	NPD6921	Approved
0.6587	Remote Similarity	NPD5247	Approved
0.6587	Remote Similarity	NPD5250	Approved
0.6587	Remote Similarity	NPD5251	Approved
0.6587	Remote Similarity	NPD5248	Approved
0.6587	Remote Similarity	NPD5249	Phase 3
0.6579	Remote Similarity	NPD3573	Approved
0.6575	Remote Similarity	NPD7625	Phase 1
0.6574	Remote Similarity	NPD6116	Phase 1
0.656	Remote Similarity	NPD5128	Approved
0.6496	Remote Similarity	NPD5281	Approved
0.6496	Remote Similarity	NPD5284	Approved
0.6496	Remote Similarity	NPD7983	Approved
0.6491	Remote Similarity	NPD5279	Phase 3
0.6484	Remote Similarity	NPD6053	Discontinued
0.6481	Remote Similarity	NPD6117	Approved
0.648	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5210	Approved
0.6471	Remote Similarity	NPD4629	Approved
0.6466	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6101	Approved
0.6466	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7799	Discontinued
0.6439	Remote Similarity	NPD4522	Approved
0.6429	Remote Similarity	NPD4221	Approved
0.6429	Remote Similarity	NPD4223	Phase 3

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