NPASS Compound

Structure

NPC475091 OpenBabel07101719142D 29 31 0 0 1 0 0 0 0 0999 V2000 2.6107 -1.4039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6145 -3.1500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3557 -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 3.4768 -0.9039 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 3.3216 -2.4429 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 4.3428 -1.4039 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 4.0287 -3.1500 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 3.4768 0.0961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 6 10 2 0 0 0 0 7 16 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 13 16 1 0 0 0 0 13 28 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 24 2 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 17 8 1 6 0 0 0 17 19 1 0 0 0 0 18 22 1 1 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 19 23 1 1 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 26 1 0 0 0 0 22 4 1 1 0 0 0 23 12 1 1 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.24
Volume:	422.89
LogP:	2.225
LogD:	1.963
LogS:	-3.411
# Rotatable Bonds:	5
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.721
Synthetic Accessibility Score:	5.652
Fsp3:	0.739
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.708
MDCK Permeability:	1.8923039533547126e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.406
Plasma Protein Binding (PPB):	27.005725860595703%
Volume Distribution (VD):	0.842
Pgp-substrate:	48.01479721069336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.198
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.774
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.13
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.326
CYP3A4-inhibitor:	0.905
CYP3A4-substrate:	0.381

ADMET: Excretion

Clearance (CL):	4.814
Half-life (T1/2):	0.206

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.763
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.439
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.403
Carcinogencity:	0.895
Eye Corrosion:	0.013
Eye Irritation:	0.031
Respiratory Toxicity:	0.193

Download Data

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

Natural Product: NPC475091

Natural Product ID:	NPC475091
*Common Name:**	Florxenilide C Monoacetate
IUPAC Name:	n.a.
Synonyms:	Florxenilide C Monoacetate
Standard InCHIKey:	QZALMEQXFZQNTK-JIRVKYQSSA-N
Standard InCHI:	InChI=1S/C23H34O6/c1-15(24)29-18-9-12-23(27-5)14-22(18,4)11-8-17-16(7-6-10-21(2,3)26)13-28-20(25)19(17)23/h6-7,10,17-19,26H,8-9,11-14H2,1-5H3/b10-6+,16-7-/t17-,18+,19+,22+,23-/m1/s1
SMILES:	CC(=O)OC1CCC2(CC1(CCC3C2C(=O)OCC3=CC=CC(C)(C)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497099
PubChem CID:	44583844
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
NPT1183	Cell Line	WiDr	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[455229]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[455229]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[455229]

☑ 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 NPC475091 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	217
0.1-0.2	1185
0.2-0.3	3839
0.3-0.4	6487
0.4-0.5	15030
0.5-0.6	8733
0.6-0.7	6169
0.7-0.8	1027
0.8-0.85	5
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC239162
0.9583	High Similarity	NPC478156
0.9175	High Similarity	NPC474718
0.88	High Similarity	NPC474709
0.8241	Intermediate Similarity	NPC90952
0.8173	Intermediate Similarity	NPC329345
0.8173	Intermediate Similarity	NPC473283
0.8173	Intermediate Similarity	NPC475526
0.8108	Intermediate Similarity	NPC476959
0.8077	Intermediate Similarity	NPC162973
0.8073	Intermediate Similarity	NPC277769
0.8073	Intermediate Similarity	NPC4573
0.8039	Intermediate Similarity	NPC254496
0.8037	Intermediate Similarity	NPC102843
0.7981	Intermediate Similarity	NPC111292
0.7938	Intermediate Similarity	NPC476104
0.7928	Intermediate Similarity	NPC73314
0.7925	Intermediate Similarity	NPC470297
0.7905	Intermediate Similarity	NPC164551
0.7905	Intermediate Similarity	NPC320447
0.79	Intermediate Similarity	NPC475972
0.7895	Intermediate Similarity	NPC476962
0.7895	Intermediate Similarity	NPC475003
0.7885	Intermediate Similarity	NPC471413
0.7879	Intermediate Similarity	NPC471342
0.7879	Intermediate Similarity	NPC469866
0.787	Intermediate Similarity	NPC94377
0.787	Intermediate Similarity	NPC89171
0.787	Intermediate Similarity	NPC476802
0.7864	Intermediate Similarity	NPC285513
0.7857	Intermediate Similarity	NPC476963
0.785	Intermediate Similarity	NPC34768
0.785	Intermediate Similarity	NPC284365
0.785	Intermediate Similarity	NPC252296
0.785	Intermediate Similarity	NPC123726
0.7843	Intermediate Similarity	NPC134067
0.7843	Intermediate Similarity	NPC266899
0.7843	Intermediate Similarity	NPC217329
0.7835	Intermediate Similarity	NPC471344
0.783	Intermediate Similarity	NPC72151
0.781	Intermediate Similarity	NPC116139
0.781	Intermediate Similarity	NPC471412
0.781	Intermediate Similarity	NPC242666
0.7807	Intermediate Similarity	NPC236918
0.7807	Intermediate Similarity	NPC470186
0.7807	Intermediate Similarity	NPC156745
0.78	Intermediate Similarity	NPC232202
0.7788	Intermediate Similarity	NPC134430
0.7788	Intermediate Similarity	NPC475809
0.7788	Intermediate Similarity	NPC316598
0.7778	Intermediate Similarity	NPC184512
0.7778	Intermediate Similarity	NPC302788
0.7768	Intermediate Similarity	NPC181145
0.7767	Intermediate Similarity	NPC134072
0.7767	Intermediate Similarity	NPC242848
0.7767	Intermediate Similarity	NPC202833
0.7767	Intermediate Similarity	NPC234993
0.7757	Intermediate Similarity	NPC118911
0.7748	Intermediate Similarity	NPC269530
0.7739	Intermediate Similarity	NPC329080
0.7739	Intermediate Similarity	NPC185876
0.7739	Intermediate Similarity	NPC475885
0.7739	Intermediate Similarity	NPC472759
0.7739	Intermediate Similarity	NPC19336
0.7736	Intermediate Similarity	NPC66110
0.7736	Intermediate Similarity	NPC476081
0.7727	Intermediate Similarity	NPC281624
0.7727	Intermediate Similarity	NPC478209
0.7727	Intermediate Similarity	NPC472666
0.7723	Intermediate Similarity	NPC473944
0.7719	Intermediate Similarity	NPC472760
0.7714	Intermediate Similarity	NPC54705
0.7706	Intermediate Similarity	NPC318363
0.7706	Intermediate Similarity	NPC475418
0.7706	Intermediate Similarity	NPC322903
0.7706	Intermediate Similarity	NPC473482
0.7692	Intermediate Similarity	NPC2049
0.7692	Intermediate Similarity	NPC472851
0.7692	Intermediate Similarity	NPC287668
0.7685	Intermediate Similarity	NPC1679
0.7685	Intermediate Similarity	NPC469607
0.7679	Intermediate Similarity	NPC469496
0.7679	Intermediate Similarity	NPC312017
0.7679	Intermediate Similarity	NPC75167
0.7679	Intermediate Similarity	NPC311592
0.7679	Intermediate Similarity	NPC469454
0.7679	Intermediate Similarity	NPC469463
0.7679	Intermediate Similarity	NPC9848
0.7679	Intermediate Similarity	NPC471204
0.7677	Intermediate Similarity	NPC231599
0.7677	Intermediate Similarity	NPC86005
0.767	Intermediate Similarity	NPC471786
0.767	Intermediate Similarity	NPC37603
0.7664	Intermediate Similarity	NPC90177
0.7664	Intermediate Similarity	NPC134270
0.7658	Intermediate Similarity	NPC179798
0.7658	Intermediate Similarity	NPC304180
0.7653	Intermediate Similarity	NPC474369
0.7652	Intermediate Similarity	NPC473636
0.7652	Intermediate Similarity	NPC77689
0.7652	Intermediate Similarity	NPC473839
0.7652	Intermediate Similarity	NPC180640
0.7652	Intermediate Similarity	NPC211093
0.7647	Intermediate Similarity	NPC99653
0.7647	Intermediate Similarity	NPC476049
0.7647	Intermediate Similarity	NPC7349
0.7642	Intermediate Similarity	NPC62670
0.7642	Intermediate Similarity	NPC474899
0.7642	Intermediate Similarity	NPC474912
0.7642	Intermediate Similarity	NPC476478
0.7642	Intermediate Similarity	NPC282524
0.7636	Intermediate Similarity	NPC273433
0.7636	Intermediate Similarity	NPC475065
0.7636	Intermediate Similarity	NPC42662
0.7632	Intermediate Similarity	NPC473656
0.7632	Intermediate Similarity	NPC469684
0.7624	Intermediate Similarity	NPC209816
0.7619	Intermediate Similarity	NPC255592
0.7619	Intermediate Similarity	NPC187761
0.7619	Intermediate Similarity	NPC83895
0.7619	Intermediate Similarity	NPC244411
0.7619	Intermediate Similarity	NPC261377
0.7619	Intermediate Similarity	NPC308567
0.7615	Intermediate Similarity	NPC476958
0.7615	Intermediate Similarity	NPC179380
0.7615	Intermediate Similarity	NPC329048
0.7615	Intermediate Similarity	NPC112780
0.7615	Intermediate Similarity	NPC330011
0.7615	Intermediate Similarity	NPC67321
0.7615	Intermediate Similarity	NPC263729
0.7615	Intermediate Similarity	NPC475570
0.7615	Intermediate Similarity	NPC473284
0.7615	Intermediate Similarity	NPC187435
0.7611	Intermediate Similarity	NPC470953
0.76	Intermediate Similarity	NPC24816
0.7596	Intermediate Similarity	NPC29952
0.7593	Intermediate Similarity	NPC474898
0.7593	Intermediate Similarity	NPC470321
0.7593	Intermediate Similarity	NPC473207
0.7593	Intermediate Similarity	NPC81567
0.7593	Intermediate Similarity	NPC146731
0.7593	Intermediate Similarity	NPC264867
0.7593	Intermediate Similarity	NPC309190
0.7593	Intermediate Similarity	NPC201880
0.7589	Intermediate Similarity	NPC174836
0.7589	Intermediate Similarity	NPC476801
0.7586	Intermediate Similarity	NPC48692
0.7583	Intermediate Similarity	NPC236999
0.7576	Intermediate Similarity	NPC198314
0.7576	Intermediate Similarity	NPC116575
0.7576	Intermediate Similarity	NPC476982
0.7576	Intermediate Similarity	NPC475753
0.7573	Intermediate Similarity	NPC38830
0.7573	Intermediate Similarity	NPC474841
0.7573	Intermediate Similarity	NPC105490
0.7573	Intermediate Similarity	NPC471446
0.7573	Intermediate Similarity	NPC473434
0.757	Intermediate Similarity	NPC475038
0.757	Intermediate Similarity	NPC469606
0.757	Intermediate Similarity	NPC273005
0.757	Intermediate Similarity	NPC109195
0.757	Intermediate Similarity	NPC114540
0.757	Intermediate Similarity	NPC471363
0.757	Intermediate Similarity	NPC238397
0.757	Intermediate Similarity	NPC155332
0.757	Intermediate Similarity	NPC32577
0.757	Intermediate Similarity	NPC31058
0.757	Intermediate Similarity	NPC183571
0.7568	Intermediate Similarity	NPC119550
0.7568	Intermediate Similarity	NPC472214
0.7568	Intermediate Similarity	NPC42776
0.7568	Intermediate Similarity	NPC472215
0.7565	Intermediate Similarity	NPC475372
0.7565	Intermediate Similarity	NPC284707
0.7563	Intermediate Similarity	NPC181999
0.7551	Intermediate Similarity	NPC102048
0.7549	Intermediate Similarity	NPC36491
0.7549	Intermediate Similarity	NPC124374
0.7549	Intermediate Similarity	NPC249034
0.7549	Intermediate Similarity	NPC477574
0.7547	Intermediate Similarity	NPC477521
0.7547	Intermediate Similarity	NPC306856
0.7547	Intermediate Similarity	NPC473204
0.7547	Intermediate Similarity	NPC16601
0.7545	Intermediate Similarity	NPC289702
0.7545	Intermediate Similarity	NPC472219
0.7545	Intermediate Similarity	NPC476765
0.7545	Intermediate Similarity	NPC473483
0.7545	Intermediate Similarity	NPC151393
0.7545	Intermediate Similarity	NPC208461
0.7545	Intermediate Similarity	NPC472218
0.7545	Intermediate Similarity	NPC472217
0.7544	Intermediate Similarity	NPC477509
0.7544	Intermediate Similarity	NPC471127
0.7544	Intermediate Similarity	NPC154363
0.7544	Intermediate Similarity	NPC234858
0.7526	Intermediate Similarity	NPC476984
0.7526	Intermediate Similarity	NPC475395
0.7525	Intermediate Similarity	NPC16265
0.7525	Intermediate Similarity	NPC256902

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 NPC475091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1386
0.2-0.3	3519
0.3-0.4	2461
0.4-0.5	1076
0.5-0.6	339
0.6-0.7	166
0.7-0.8	8
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
0.7822	Intermediate Similarity	NPD5778	Approved
0.7822	Intermediate Similarity	NPD5779	Approved
0.7549	Intermediate Similarity	NPD6411	Approved
0.7545	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7640	Approved
0.7383	Intermediate Similarity	NPD6648	Approved
0.7383	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD7983	Approved
0.7353	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6101	Approved
0.729	Intermediate Similarity	NPD7638	Approved
0.7227	Intermediate Similarity	NPD8516	Approved
0.7227	Intermediate Similarity	NPD8515	Approved
0.7227	Intermediate Similarity	NPD8517	Approved
0.7227	Intermediate Similarity	NPD8513	Phase 3
0.7212	Intermediate Similarity	NPD7637	Suspended
0.713	Intermediate Similarity	NPD4225	Approved
0.7105	Intermediate Similarity	NPD6371	Approved
0.7103	Intermediate Similarity	NPD7839	Suspended
0.708	Intermediate Similarity	NPD6686	Approved
0.7034	Intermediate Similarity	NPD7115	Discovery
0.7018	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5344	Discontinued
0.696	Remote Similarity	NPD7319	Approved
0.6957	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD46	Approved
0.6952	Remote Similarity	NPD6698	Approved
0.6935	Remote Similarity	NPD8074	Phase 3
0.6855	Remote Similarity	NPD7507	Approved
0.6842	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD8039	Approved
0.6803	Remote Similarity	NPD6921	Approved
0.6796	Remote Similarity	NPD1694	Approved
0.6786	Remote Similarity	NPD7632	Discontinued
0.6783	Remote Similarity	NPD6881	Approved
0.6783	Remote Similarity	NPD6899	Approved
0.6759	Remote Similarity	NPD5282	Discontinued
0.6759	Remote Similarity	NPD7748	Approved
0.6754	Remote Similarity	NPD7128	Approved
0.6754	Remote Similarity	NPD5739	Approved
0.6754	Remote Similarity	NPD6675	Approved
0.6754	Remote Similarity	NPD6402	Approved
0.6727	Remote Similarity	NPD7902	Approved
0.6721	Remote Similarity	NPD6319	Approved
0.6696	Remote Similarity	NPD5697	Approved
0.6695	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD7102	Approved
0.664	Remote Similarity	NPD7492	Approved
0.6638	Remote Similarity	NPD7320	Approved
0.6636	Remote Similarity	NPD7838	Discovery
0.6636	Remote Similarity	NPD5785	Approved
0.661	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6869	Approved
0.661	Remote Similarity	NPD6649	Approved
0.661	Remote Similarity	NPD6617	Approved
0.661	Remote Similarity	NPD6650	Approved
0.661	Remote Similarity	NPD8130	Phase 1
0.661	Remote Similarity	NPD6847	Approved
0.6609	Remote Similarity	NPD6008	Approved
0.6606	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7900	Approved
0.6587	Remote Similarity	NPD6616	Approved
0.6587	Remote Similarity	NPD8273	Phase 1
0.6585	Remote Similarity	NPD6054	Approved
0.6581	Remote Similarity	NPD6372	Approved
0.6581	Remote Similarity	NPD6014	Approved
0.6581	Remote Similarity	NPD6373	Approved
0.6581	Remote Similarity	NPD6013	Approved
0.6581	Remote Similarity	NPD6012	Approved
0.6574	Remote Similarity	NPD7515	Phase 2
0.656	Remote Similarity	NPD8328	Phase 3
0.6557	Remote Similarity	NPD7327	Approved
0.6557	Remote Similarity	NPD7328	Approved
0.6555	Remote Similarity	NPD8297	Approved
0.6555	Remote Similarity	NPD6882	Approved
0.6552	Remote Similarity	NPD5701	Approved
0.6542	Remote Similarity	NPD1695	Approved
0.6538	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7078	Approved
0.6532	Remote Similarity	NPD7503	Approved
0.6505	Remote Similarity	NPD5209	Approved
0.6504	Remote Similarity	NPD7516	Approved
0.65	Remote Similarity	NPD8133	Approved
0.65	Remote Similarity	NPD4632	Approved
0.6496	Remote Similarity	NPD6011	Approved
0.6491	Remote Similarity	NPD5211	Phase 2
0.6484	Remote Similarity	NPD7736	Approved
0.648	Remote Similarity	NPD6370	Approved
0.6475	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6059	Approved
0.6442	Remote Similarity	NPD6695	Phase 3
0.6442	Remote Similarity	NPD7154	Phase 3
0.6441	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8035	Phase 2
0.6422	Remote Similarity	NPD8034	Phase 2
0.6415	Remote Similarity	NPD5786	Approved
0.6406	Remote Similarity	NPD8293	Discontinued
0.64	Remote Similarity	NPD6016	Approved
0.64	Remote Similarity	NPD6015	Approved
0.6387	Remote Similarity	NPD4634	Approved
0.6379	Remote Similarity	NPD5141	Approved
0.6355	Remote Similarity	NPD4251	Approved
0.6355	Remote Similarity	NPD4250	Approved
0.6349	Remote Similarity	NPD5988	Approved
0.6346	Remote Similarity	NPD6435	Approved
0.6346	Remote Similarity	NPD4269	Approved
0.6346	Remote Similarity	NPD4270	Approved
0.6341	Remote Similarity	NPD6009	Approved
0.6336	Remote Similarity	NPD7260	Phase 2
0.6333	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD8451	Approved
0.632	Remote Similarity	NPD8377	Approved
0.632	Remote Similarity	NPD8294	Approved
0.6316	Remote Similarity	NPD4696	Approved
0.6316	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD5286	Approved
0.6311	Remote Similarity	NPD4819	Approved
0.6311	Remote Similarity	NPD4820	Approved
0.6311	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4822	Approved
0.6311	Remote Similarity	NPD4821	Approved
0.6299	Remote Similarity	NPD7604	Phase 2
0.6286	Remote Similarity	NPD5362	Discontinued
0.6283	Remote Similarity	NPD4755	Approved
0.6283	Remote Similarity	NPD6084	Phase 2
0.6283	Remote Similarity	NPD6083	Phase 2
0.6279	Remote Similarity	NPD8448	Approved
0.6273	Remote Similarity	NPD5281	Approved
0.6273	Remote Similarity	NPD6079	Approved
0.6273	Remote Similarity	NPD5284	Approved
0.6271	Remote Similarity	NPD6412	Phase 2
0.627	Remote Similarity	NPD8379	Approved
0.627	Remote Similarity	NPD8033	Approved
0.627	Remote Similarity	NPD8296	Approved
0.627	Remote Similarity	NPD8380	Approved
0.627	Remote Similarity	NPD8378	Approved
0.627	Remote Similarity	NPD5983	Phase 2
0.627	Remote Similarity	NPD8335	Approved
0.6262	Remote Similarity	NPD7146	Approved
0.6262	Remote Similarity	NPD5330	Approved
0.6262	Remote Similarity	NPD7521	Approved
0.6262	Remote Similarity	NPD4249	Approved
0.6262	Remote Similarity	NPD6684	Approved
0.6262	Remote Similarity	NPD7334	Approved
0.6262	Remote Similarity	NPD6409	Approved
0.6262	Remote Similarity	NPD6422	Discontinued
0.625	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD8299	Approved
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD8342	Approved
0.625	Remote Similarity	NPD8341	Approved
0.625	Remote Similarity	NPD8340	Approved
0.624	Remote Similarity	NPD7100	Approved
0.624	Remote Similarity	NPD7101	Approved
0.6239	Remote Similarity	NPD6051	Approved
0.6239	Remote Similarity	NPD5328	Approved
0.6222	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4633	Approved
0.6207	Remote Similarity	NPD5225	Approved
0.6207	Remote Similarity	NPD5226	Approved
0.6207	Remote Similarity	NPD5224	Approved
0.6204	Remote Similarity	NPD7524	Approved
0.6204	Remote Similarity	NPD7750	Discontinued
0.6202	Remote Similarity	NPD6336	Discontinued
0.6186	Remote Similarity	NPD5048	Discontinued
0.6174	Remote Similarity	NPD4700	Approved
0.6172	Remote Similarity	NPD7830	Approved
0.6172	Remote Similarity	NPD7829	Approved
0.6168	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5363	Approved
0.6168	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD5368	Approved
0.6154	Remote Similarity	NPD7332	Phase 2
0.6154	Remote Similarity	NPD6931	Approved
0.6154	Remote Similarity	NPD4252	Approved
0.6154	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD6930	Phase 2
0.6154	Remote Similarity	NPD7514	Phase 3
0.6154	Remote Similarity	NPD5175	Approved
0.6147	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6903	Approved
0.6147	Remote Similarity	NPD6672	Approved
0.6147	Remote Similarity	NPD5737	Approved
0.6142	Remote Similarity	NPD8444	Approved
0.6139	Remote Similarity	NPD8264	Approved
0.6136	Remote Similarity	NPD8392	Approved
0.6136	Remote Similarity	NPD8391	Approved
0.6136	Remote Similarity	NPD8390	Approved
0.6129	Remote Similarity	NPD6274	Approved
0.6126	Remote Similarity	NPD5693	Phase 1

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