NPASS Compound

Structure

NPC239162 OpenBabel07101718322D 26 28 0 0 1 0 0 0 0 0999 V2000 5.5123 -1.4770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8052 -2.1841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1904 2.4110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7149 3.3204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8733 -0.7699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9074 -1.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1034 0.3714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7447 0.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5804 -1.4770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6107 0.8787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8787 0.5961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5073 -0.5073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7447 2.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2003 -0.3216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3860 0.3714 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6107 0.5961 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8787 0.8787 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1857 0.6930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5464 -1.2182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6107 1.5961 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8787 1.5961 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4768 0.0961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5214 1.4001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8052 -0.2523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2990 2.4110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 9 2 0 0 0 0 6 14 2 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 7 1 6 0 0 0 15 17 1 0 0 0 0 16 20 1 1 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 1 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 20 3 1 6 0 0 0 21 11 1 1 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.22
Volume:	382.145
LogP:	1.646
LogD:	1.504
LogS:	-2.198
# Rotatable Bonds:	3
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	5.686
Fsp3:	0.762
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.624
MDCK Permeability:	2.7850610422319733e-05
Pgp-inhibitor:	0.099
Pgp-substrate:	0.325
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.347
Plasma Protein Binding (PPB):	21.365013122558594%
Volume Distribution (VD):	0.956
Pgp-substrate:	57.358192443847656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.717
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.167
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.324
CYP3A4-inhibitor:	0.878
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	7.523
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.247
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.367
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.197
Carcinogencity:	0.938
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.626

Download Data

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

Natural Product: NPC239162

Natural Product ID:	NPC239162
*Common Name:**	Florxenilide C
IUPAC Name:	n.a.
Synonyms:	Florxenilide C
Standard InCHIKey:	CUFNSNQMTXWTPT-AFAVWLOWSA-N
Standard InCHI:	InChI=1S/C21H32O5/c1-19(2,24)9-5-6-14-12-26-18(23)17-15(14)7-10-20(3)13-21(17,25-4)11-8-16(20)22/h5-6,9,15-17,22,24H,7-8,10-13H2,1-4H3/b9-5+,14-6-/t15-,16+,17+,20+,21-/m1/s1
SMILES:	CC(C)(/C=C/C=C1/COC(=O)[C@@H]2[C@@H]1CC[C@@]1(C)C[C@@]2(CC[C@@H]1O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497098
PubChem CID:	15939639
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16643051]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9868153]
NPO5870	Xenia florida	Species	n.a.	n.a.	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
ED50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[541322]
NPT1183	Cell Line	WiDr	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[541322]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[541322]

☑ 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 NPC239162 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	218
0.1-0.2	1137
0.2-0.3	3708
0.3-0.4	6318
0.4-0.5	14353
0.5-0.6	8973
0.6-0.7	6563
0.7-0.8	1404
0.8-0.85	18
0.85-0.9	1
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC475091
0.9792	High Similarity	NPC478156
0.9381	High Similarity	NPC474718
0.9	High Similarity	NPC474709
0.8426	Intermediate Similarity	NPC90952
0.8288	Intermediate Similarity	NPC476959
0.8257	Intermediate Similarity	NPC277769
0.8257	Intermediate Similarity	NPC4573
0.8235	Intermediate Similarity	NPC254496
0.8224	Intermediate Similarity	NPC102843
0.8173	Intermediate Similarity	NPC111292
0.81	Intermediate Similarity	NPC475972
0.8095	Intermediate Similarity	NPC162973
0.8095	Intermediate Similarity	NPC164551
0.807	Intermediate Similarity	NPC476962
0.807	Intermediate Similarity	NPC475003
0.8058	Intermediate Similarity	NPC285513
0.8056	Intermediate Similarity	NPC476802
0.8056	Intermediate Similarity	NPC89171
0.8039	Intermediate Similarity	NPC134067
0.8039	Intermediate Similarity	NPC266899
0.8037	Intermediate Similarity	NPC284365
0.8037	Intermediate Similarity	NPC123726
0.8037	Intermediate Similarity	NPC252296
0.8037	Intermediate Similarity	NPC34768
0.8036	Intermediate Similarity	NPC476963
0.8019	Intermediate Similarity	NPC473283
0.8019	Intermediate Similarity	NPC329345
0.8019	Intermediate Similarity	NPC475526
0.8	Intermediate Similarity	NPC471412
0.8	Intermediate Similarity	NPC232202
0.8	Intermediate Similarity	NPC242666
0.7982	Intermediate Similarity	NPC236918
0.7982	Intermediate Similarity	NPC156745
0.7981	Intermediate Similarity	NPC316598
0.7965	Intermediate Similarity	NPC475809
0.7965	Intermediate Similarity	NPC134430
0.7963	Intermediate Similarity	NPC184512
0.7961	Intermediate Similarity	NPC202833
0.7961	Intermediate Similarity	NPC234993
0.7961	Intermediate Similarity	NPC242848
0.7961	Intermediate Similarity	NPC134072
0.7959	Intermediate Similarity	NPC476104
0.7946	Intermediate Similarity	NPC73314
0.7946	Intermediate Similarity	NPC181145
0.7944	Intermediate Similarity	NPC118911
0.7925	Intermediate Similarity	NPC476081
0.7913	Intermediate Similarity	NPC185876
0.7913	Intermediate Similarity	NPC19336
0.7913	Intermediate Similarity	NPC475885
0.7913	Intermediate Similarity	NPC472759
0.7913	Intermediate Similarity	NPC329080
0.7909	Intermediate Similarity	NPC478209
0.7905	Intermediate Similarity	NPC471413
0.79	Intermediate Similarity	NPC471342
0.79	Intermediate Similarity	NPC469866
0.7895	Intermediate Similarity	NPC472760
0.789	Intermediate Similarity	NPC322903
0.789	Intermediate Similarity	NPC94377
0.7885	Intermediate Similarity	NPC472851
0.7885	Intermediate Similarity	NPC287668
0.7879	Intermediate Similarity	NPC86005
0.787	Intermediate Similarity	NPC469607
0.7864	Intermediate Similarity	NPC37603
0.7864	Intermediate Similarity	NPC471786
0.7857	Intermediate Similarity	NPC471344
0.7857	Intermediate Similarity	NPC312017
0.7857	Intermediate Similarity	NPC469454
0.7857	Intermediate Similarity	NPC469496
0.7857	Intermediate Similarity	NPC9848
0.7857	Intermediate Similarity	NPC75167
0.7857	Intermediate Similarity	NPC469463
0.7857	Intermediate Similarity	NPC311592
0.785	Intermediate Similarity	NPC134270
0.785	Intermediate Similarity	NPC72151
0.785	Intermediate Similarity	NPC90177
0.7843	Intermediate Similarity	NPC476049
0.7843	Intermediate Similarity	NPC99653
0.783	Intermediate Similarity	NPC116139
0.783	Intermediate Similarity	NPC282524
0.7826	Intermediate Similarity	NPC211093
0.7826	Intermediate Similarity	NPC473636
0.7826	Intermediate Similarity	NPC77689
0.7826	Intermediate Similarity	NPC473839
0.7826	Intermediate Similarity	NPC180640
0.7826	Intermediate Similarity	NPC470186
0.7822	Intermediate Similarity	NPC209816
0.7818	Intermediate Similarity	NPC475065
0.7818	Intermediate Similarity	NPC273433
0.7818	Intermediate Similarity	NPC42662
0.781	Intermediate Similarity	NPC261377
0.781	Intermediate Similarity	NPC308567
0.781	Intermediate Similarity	NPC83895
0.781	Intermediate Similarity	NPC187761
0.781	Intermediate Similarity	NPC255592
0.7807	Intermediate Similarity	NPC473656
0.7807	Intermediate Similarity	NPC469684
0.7798	Intermediate Similarity	NPC112780
0.7798	Intermediate Similarity	NPC263729
0.7798	Intermediate Similarity	NPC179380
0.7798	Intermediate Similarity	NPC329048
0.7798	Intermediate Similarity	NPC330011
0.7798	Intermediate Similarity	NPC302788
0.7798	Intermediate Similarity	NPC67321
0.7798	Intermediate Similarity	NPC473284
0.7798	Intermediate Similarity	NPC187435
0.7788	Intermediate Similarity	NPC470953
0.7778	Intermediate Similarity	NPC116575
0.7778	Intermediate Similarity	NPC309190
0.7778	Intermediate Similarity	NPC470321
0.7778	Intermediate Similarity	NPC470297
0.7778	Intermediate Similarity	NPC264867
0.7778	Intermediate Similarity	NPC475753
0.7778	Intermediate Similarity	NPC473207
0.7778	Intermediate Similarity	NPC201880
0.7778	Intermediate Similarity	NPC81567
0.7768	Intermediate Similarity	NPC269530
0.7768	Intermediate Similarity	NPC476801
0.7768	Intermediate Similarity	NPC174836
0.7767	Intermediate Similarity	NPC105490
0.7759	Intermediate Similarity	NPC48692
0.7757	Intermediate Similarity	NPC109195
0.7757	Intermediate Similarity	NPC238397
0.7757	Intermediate Similarity	NPC469606
0.7757	Intermediate Similarity	NPC66110
0.7757	Intermediate Similarity	NPC155332
0.7757	Intermediate Similarity	NPC471363
0.7757	Intermediate Similarity	NPC32577
0.7757	Intermediate Similarity	NPC273005
0.7757	Intermediate Similarity	NPC475038
0.7757	Intermediate Similarity	NPC320447
0.7757	Intermediate Similarity	NPC114540
0.7757	Intermediate Similarity	NPC31058
0.7755	Intermediate Similarity	NPC102048
0.775	Intermediate Similarity	NPC236999
0.7748	Intermediate Similarity	NPC472215
0.7748	Intermediate Similarity	NPC472214
0.7748	Intermediate Similarity	NPC119550
0.7748	Intermediate Similarity	NPC472666
0.7748	Intermediate Similarity	NPC42776
0.7745	Intermediate Similarity	NPC249034
0.7745	Intermediate Similarity	NPC36491
0.7745	Intermediate Similarity	NPC477574
0.7745	Intermediate Similarity	NPC124374
0.7739	Intermediate Similarity	NPC284707
0.7736	Intermediate Similarity	NPC54705
0.7736	Intermediate Similarity	NPC477521
0.7736	Intermediate Similarity	NPC306856
0.7727	Intermediate Similarity	NPC476765
0.7727	Intermediate Similarity	NPC318363
0.7727	Intermediate Similarity	NPC208461
0.7727	Intermediate Similarity	NPC475418
0.7727	Intermediate Similarity	NPC289702
0.7727	Intermediate Similarity	NPC472217
0.7727	Intermediate Similarity	NPC472218
0.7727	Intermediate Similarity	NPC151393
0.7727	Intermediate Similarity	NPC472219
0.7727	Intermediate Similarity	NPC473482
0.7723	Intermediate Similarity	NPC256902
0.7723	Intermediate Similarity	NPC118193
0.7723	Intermediate Similarity	NPC16265
0.7719	Intermediate Similarity	NPC234858
0.7719	Intermediate Similarity	NPC471127
0.7719	Intermediate Similarity	NPC154363
0.7714	Intermediate Similarity	NPC40812
0.7706	Intermediate Similarity	NPC111952
0.7706	Intermediate Similarity	NPC478208
0.7706	Intermediate Similarity	NPC127609
0.7706	Intermediate Similarity	NPC1679
0.77	Intermediate Similarity	NPC477959
0.77	Intermediate Similarity	NPC231599
0.7699	Intermediate Similarity	NPC478212
0.7699	Intermediate Similarity	NPC71889
0.7699	Intermediate Similarity	NPC474271
0.7699	Intermediate Similarity	NPC471204
0.7699	Intermediate Similarity	NPC25909
0.7692	Intermediate Similarity	NPC272050
0.7692	Intermediate Similarity	NPC217329
0.7685	Intermediate Similarity	NPC95899
0.7685	Intermediate Similarity	NPC7644
0.7685	Intermediate Similarity	NPC127933
0.7685	Intermediate Similarity	NPC69171
0.7685	Intermediate Similarity	NPC159533
0.7685	Intermediate Similarity	NPC478057
0.7685	Intermediate Similarity	NPC475889
0.7685	Intermediate Similarity	NPC474165
0.7685	Intermediate Similarity	NPC471938
0.7685	Intermediate Similarity	NPC120321
0.7685	Intermediate Similarity	NPC475050
0.7685	Intermediate Similarity	NPC7613
0.7679	Intermediate Similarity	NPC317107
0.7679	Intermediate Similarity	NPC179798
0.7679	Intermediate Similarity	NPC304180
0.767	Intermediate Similarity	NPC139692
0.767	Intermediate Similarity	NPC199543
0.767	Intermediate Similarity	NPC7349
0.7667	Intermediate Similarity	NPC471940
0.7664	Intermediate Similarity	NPC62670
0.7664	Intermediate Similarity	NPC469657
0.7664	Intermediate Similarity	NPC11974

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 NPC239162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1374
0.2-0.3	3422
0.3-0.4	2509
0.4-0.5	1097
0.5-0.6	346
0.6-0.7	195
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.802	Intermediate Similarity	NPD5778	Approved
0.802	Intermediate Similarity	NPD5779	Approved
0.7745	Intermediate Similarity	NPD6411	Approved
0.7727	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD7983	Approved
0.757	Intermediate Similarity	NPD7639	Approved
0.757	Intermediate Similarity	NPD7640	Approved
0.7549	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6101	Approved
0.7477	Intermediate Similarity	NPD7638	Approved
0.7404	Intermediate Similarity	NPD7637	Suspended
0.7395	Intermediate Similarity	NPD8513	Phase 3
0.7395	Intermediate Similarity	NPD8516	Approved
0.7395	Intermediate Similarity	NPD8517	Approved
0.7395	Intermediate Similarity	NPD8515	Approved
0.7315	Intermediate Similarity	NPD4225	Approved
0.729	Intermediate Similarity	NPD7839	Suspended
0.7281	Intermediate Similarity	NPD6371	Approved
0.7257	Intermediate Similarity	NPD6686	Approved
0.7248	Intermediate Similarity	NPD6648	Approved
0.7203	Intermediate Similarity	NPD7115	Discovery
0.7196	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD46	Approved
0.7143	Intermediate Similarity	NPD6698	Approved
0.712	Intermediate Similarity	NPD7319	Approved
0.7097	Intermediate Similarity	NPD8074	Phase 3
0.7016	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6921	Approved
0.6964	Remote Similarity	NPD7632	Discontinued
0.6957	Remote Similarity	NPD6881	Approved
0.6957	Remote Similarity	NPD6899	Approved
0.693	Remote Similarity	NPD6402	Approved
0.693	Remote Similarity	NPD7128	Approved
0.693	Remote Similarity	NPD5739	Approved
0.693	Remote Similarity	NPD6675	Approved
0.6885	Remote Similarity	NPD6319	Approved
0.687	Remote Similarity	NPD5697	Approved
0.687	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6053	Discontinued
0.6838	Remote Similarity	NPD7290	Approved
0.6838	Remote Similarity	NPD7102	Approved
0.6838	Remote Similarity	NPD6883	Approved
0.6822	Remote Similarity	NPD7838	Discovery
0.6822	Remote Similarity	NPD5785	Approved
0.681	Remote Similarity	NPD7320	Approved
0.68	Remote Similarity	NPD7492	Approved
0.6789	Remote Similarity	NPD7748	Approved
0.6789	Remote Similarity	NPD5282	Discontinued
0.678	Remote Similarity	NPD6650	Approved
0.678	Remote Similarity	NPD6847	Approved
0.678	Remote Similarity	NPD6649	Approved
0.678	Remote Similarity	NPD6617	Approved
0.678	Remote Similarity	NPD6869	Approved
0.678	Remote Similarity	NPD8130	Phase 1
0.678	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7515	Phase 2
0.6757	Remote Similarity	NPD7902	Approved
0.6752	Remote Similarity	NPD6014	Approved
0.6752	Remote Similarity	NPD6372	Approved
0.6752	Remote Similarity	NPD6012	Approved
0.6752	Remote Similarity	NPD6013	Approved
0.6752	Remote Similarity	NPD6373	Approved
0.6748	Remote Similarity	NPD6054	Approved
0.6746	Remote Similarity	NPD8273	Phase 1
0.6746	Remote Similarity	NPD6616	Approved
0.6731	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5701	Approved
0.6724	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8297	Approved
0.6723	Remote Similarity	NPD6882	Approved
0.6721	Remote Similarity	NPD7328	Approved
0.6721	Remote Similarity	NPD7327	Approved
0.672	Remote Similarity	NPD8328	Phase 3
0.6699	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6399	Phase 3
0.6694	Remote Similarity	NPD7503	Approved
0.6693	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD8039	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6641	Remote Similarity	NPD7736	Approved
0.664	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6695	Phase 3
0.6635	Remote Similarity	NPD7154	Phase 3
0.6634	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6059	Approved
0.661	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5786	Approved
0.6562	Remote Similarity	NPD8293	Discontinued
0.656	Remote Similarity	NPD6016	Approved
0.656	Remote Similarity	NPD6015	Approved
0.6555	Remote Similarity	NPD4634	Approved
0.6552	Remote Similarity	NPD5141	Approved
0.6542	Remote Similarity	NPD4251	Approved
0.6542	Remote Similarity	NPD3573	Approved
0.6542	Remote Similarity	NPD4250	Approved
0.6538	Remote Similarity	NPD4269	Approved
0.6538	Remote Similarity	NPD4270	Approved
0.6538	Remote Similarity	NPD6435	Approved
0.6508	Remote Similarity	NPD5988	Approved
0.6505	Remote Similarity	NPD4819	Approved
0.6505	Remote Similarity	NPD4822	Approved
0.6505	Remote Similarity	NPD4820	Approved
0.6505	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4821	Approved
0.6504	Remote Similarity	NPD6009	Approved
0.65	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6008	Approved
0.6491	Remote Similarity	NPD4696	Approved
0.6491	Remote Similarity	NPD5285	Approved
0.6491	Remote Similarity	NPD5286	Approved
0.6486	Remote Similarity	NPD7900	Approved
0.6486	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8451	Approved
0.648	Remote Similarity	NPD8294	Approved
0.648	Remote Similarity	NPD8377	Approved
0.6476	Remote Similarity	NPD5362	Discontinued
0.646	Remote Similarity	NPD6084	Phase 2
0.646	Remote Similarity	NPD4755	Approved
0.646	Remote Similarity	NPD6083	Phase 2
0.6457	Remote Similarity	NPD7604	Phase 2
0.6455	Remote Similarity	NPD8035	Phase 2
0.6455	Remote Similarity	NPD8034	Phase 2
0.6455	Remote Similarity	NPD6079	Approved
0.6449	Remote Similarity	NPD4249	Approved
0.6442	Remote Similarity	NPD5369	Approved
0.6441	Remote Similarity	NPD6412	Phase 2
0.6434	Remote Similarity	NPD8448	Approved
0.6429	Remote Similarity	NPD8380	Approved
0.6429	Remote Similarity	NPD8335	Approved
0.6429	Remote Similarity	NPD5983	Phase 2
0.6429	Remote Similarity	NPD8378	Approved
0.6429	Remote Similarity	NPD8033	Approved
0.6429	Remote Similarity	NPD8379	Approved
0.6429	Remote Similarity	NPD8296	Approved
0.6422	Remote Similarity	NPD1695	Approved
0.6422	Remote Similarity	NPD5328	Approved
0.6406	Remote Similarity	NPD8341	Approved
0.6406	Remote Similarity	NPD8299	Approved
0.6406	Remote Similarity	NPD8340	Approved
0.6406	Remote Similarity	NPD8342	Approved
0.64	Remote Similarity	NPD7101	Approved
0.64	Remote Similarity	NPD7100	Approved
0.6389	Remote Similarity	NPD7750	Discontinued
0.6389	Remote Similarity	NPD7524	Approved
0.6381	Remote Similarity	NPD5209	Approved
0.6379	Remote Similarity	NPD5226	Approved
0.6379	Remote Similarity	NPD4633	Approved
0.6379	Remote Similarity	NPD5225	Approved
0.6379	Remote Similarity	NPD5224	Approved
0.637	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7260	Phase 2
0.6357	Remote Similarity	NPD6336	Discontinued
0.6356	Remote Similarity	NPD5048	Discontinued
0.6355	Remote Similarity	NPD5363	Approved
0.6355	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4700	Approved
0.6346	Remote Similarity	NPD7514	Phase 3
0.6346	Remote Similarity	NPD5368	Approved
0.6346	Remote Similarity	NPD6930	Phase 2
0.6346	Remote Similarity	NPD6931	Approved
0.6346	Remote Similarity	NPD4252	Approved
0.6346	Remote Similarity	NPD7332	Phase 2
0.6337	Remote Similarity	NPD8264	Approved
0.6328	Remote Similarity	NPD7829	Approved
0.6328	Remote Similarity	NPD7830	Approved
0.6325	Remote Similarity	NPD5175	Approved
0.6325	Remote Similarity	NPD5174	Approved
0.632	Remote Similarity	NPD6335	Approved
0.6311	Remote Similarity	NPD4268	Approved
0.6311	Remote Similarity	NPD4271	Approved
0.6306	Remote Similarity	NPD5281	Approved
0.6306	Remote Similarity	NPD5284	Approved
0.6299	Remote Similarity	NPD8444	Approved
0.6296	Remote Similarity	NPD3618	Phase 1
0.6293	Remote Similarity	NPD5223	Approved
0.629	Remote Similarity	NPD6274	Approved
0.6288	Remote Similarity	NPD8390	Approved
0.6288	Remote Similarity	NPD8392	Approved
0.6288	Remote Similarity	NPD8391	Approved
0.6283	Remote Similarity	NPD5695	Phase 3
0.6262	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD6929	Approved
0.624	Remote Similarity	NPD6317	Approved
0.6228	Remote Similarity	NPD5221	Approved
0.6228	Remote Similarity	NPD5222	Approved
0.6228	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD3667	Approved
0.621	Remote Similarity	NPD6010	Discontinued
0.6204	Remote Similarity	NPD6082	Clinical (unspecified phase)

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