NPASS Compound

Structure

NPC256567 OpenBabel07101718192D 25 28 0 0 1 0 0 0 0 0999 V2000 2.1700 1.2098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3440 -1.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1830 0.9779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3948 0.0358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4051 -0.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7909 0.3725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6863 1.0397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6142 -1.0280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3040 -1.8343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2568 0.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2085 1.5395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2077 -0.6734 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5935 0.3546 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0103 -0.6913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4801 1.4775 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9601 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2967 0.9131 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8116 -1.0101 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1974 0.0179 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 -1.8365 -2.6729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5459 2.4384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8139 -1.1838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5245 -0.7768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1230 1.5065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 18 1 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 6 0 0 0 12 18 1 6 0 0 0 12 19 1 0 0 0 0 13 19 1 6 0 0 0 13 20 1 0 0 0 0 14 20 1 6 0 0 0 14 23 1 0 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 16 20 1 1 0 0 0 16 24 1 0 0 0 0 17 20 1 6 0 0 0 17 25 1 0 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	361.565
LogP:	0.4
LogD:	0.304
LogS:	-2.98
# Rotatable Bonds:	1
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	6.399
Fsp3:	0.9
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:	-5.186
MDCK Permeability:	3.8028618291718885e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.72
30% Bioavailability (F30%):	0.522

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.283
Plasma Protein Binding (PPB):	41.72657775878906%
Volume Distribution (VD):	0.647
Pgp-substrate:	59.90147399902344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.724
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	2.968
Half-life (T1/2):	0.54

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.419
Drug-inuced Liver Injury (DILI):	0.082
AMES Toxicity:	0.382
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.593
Carcinogencity:	0.053
Eye Corrosion:	0.12
Eye Irritation:	0.323
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC256567

Natural Product ID:	NPC256567
*Common Name:**	GLUUDKFJKAARFN-CNDURKJHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GLUUDKFJKAARFN-CNDURKJHSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-10-15-11(22)7-13-19(3)6-4-5-18(2,9-21)12(19)8-14(23)20(13,16(10)24)17(15)25/h11-17,21-25H,1,4-9H2,2-3H3/t11-,12+,13-,14+,15+,16+,17+,18+,19+,20-/m0/s1
SMILES:	OC[C@@]1(C)CCC[C@@]2([C@@H]1C[C@@H](O)[C@]13[C@H]2C[C@@H]([C@H]([C@H]1O)C(=C)[C@H]3O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3233967
PubChem CID:	90670209
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO15942	Isodon wikstroemioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697496]
NPO15942	Isodon wikstroemioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[489414]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[489414]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[489414]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[489414]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[489414]

☑ 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 NPC256567 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	197
0.1-0.2	2055
0.2-0.3	6924
0.3-0.4	15570
0.4-0.5	7331
0.5-0.6	5131
0.6-0.7	4250
0.7-0.8	1058
0.8-0.85	112
0.85-0.9	43
0.9-0.95	21
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC157655
0.9487	High Similarity	NPC47149
0.9375	High Similarity	NPC232023
0.9359	High Similarity	NPC5604
0.9359	High Similarity	NPC24504
0.9359	High Similarity	NPC476316
0.9241	High Similarity	NPC78545
0.9241	High Similarity	NPC71535
0.9231	High Similarity	NPC475
0.9231	High Similarity	NPC472499
0.9231	High Similarity	NPC472502
0.9231	High Similarity	NPC472500
0.9103	High Similarity	NPC138502
0.9103	High Similarity	NPC260301
0.9103	High Similarity	NPC307336
0.907	High Similarity	NPC26046
0.9036	High Similarity	NPC121981
0.9024	High Similarity	NPC255882
0.8987	High Similarity	NPC477817
0.8987	High Similarity	NPC477819
0.8987	High Similarity	NPC472501
0.8974	High Similarity	NPC38141
0.8837	High Similarity	NPC194485
0.8837	High Similarity	NPC123252
0.8837	High Similarity	NPC53890
0.8837	High Similarity	NPC219937
0.8824	High Similarity	NPC160304
0.881	High Similarity	NPC201273
0.8765	High Similarity	NPC475679
0.875	High Similarity	NPC301707
0.875	High Similarity	NPC3359
0.875	High Similarity	NPC31828
0.8718	High Similarity	NPC308440
0.8718	High Similarity	NPC472503
0.8675	High Similarity	NPC110778
0.8675	High Similarity	NPC211135
0.8675	High Similarity	NPC85095
0.8675	High Similarity	NPC216420
0.8642	High Similarity	NPC80297
0.8642	High Similarity	NPC116119
0.8642	High Similarity	NPC472742
0.8642	High Similarity	NPC475727
0.8608	High Similarity	NPC185536
0.859	High Similarity	NPC472506
0.8588	High Similarity	NPC6605
0.8588	High Similarity	NPC139724
0.8588	High Similarity	NPC24277
0.8571	High Similarity	NPC127606
0.8571	High Similarity	NPC124172
0.8571	High Similarity	NPC475798
0.8539	High Similarity	NPC280804
0.8523	High Similarity	NPC130840
0.8481	Intermediate Similarity	NPC476736
0.8462	Intermediate Similarity	NPC164045
0.8452	Intermediate Similarity	NPC193870
0.8452	Intermediate Similarity	NPC477818
0.8452	Intermediate Similarity	NPC141941
0.8452	Intermediate Similarity	NPC470929
0.8444	Intermediate Similarity	NPC241047
0.8444	Intermediate Similarity	NPC30477
0.8409	Intermediate Similarity	NPC473956
0.8409	Intermediate Similarity	NPC475751
0.8395	Intermediate Similarity	NPC257191
0.8395	Intermediate Similarity	NPC202540
0.8395	Intermediate Similarity	NPC212241
0.8395	Intermediate Similarity	NPC119355
0.8395	Intermediate Similarity	NPC331618
0.8395	Intermediate Similarity	NPC248830
0.8391	Intermediate Similarity	NPC475664
0.8375	Intermediate Similarity	NPC3403
0.8372	Intermediate Similarity	NPC152808
0.8372	Intermediate Similarity	NPC6391
0.8372	Intermediate Similarity	NPC293287
0.8353	Intermediate Similarity	NPC86238
0.8353	Intermediate Similarity	NPC209802
0.8352	Intermediate Similarity	NPC292718
0.8352	Intermediate Similarity	NPC111834
0.8352	Intermediate Similarity	NPC306797
0.8352	Intermediate Similarity	NPC169270
0.8333	Intermediate Similarity	NPC470614
0.8333	Intermediate Similarity	NPC1272
0.8333	Intermediate Similarity	NPC45296
0.8315	Intermediate Similarity	NPC41554
0.8315	Intermediate Similarity	NPC97404
0.8295	Intermediate Similarity	NPC109744
0.8295	Intermediate Similarity	NPC105495
0.8295	Intermediate Similarity	NPC470361
0.8293	Intermediate Similarity	NPC42853
0.8293	Intermediate Similarity	NPC472342
0.828	Intermediate Similarity	NPC471247
0.8276	Intermediate Similarity	NPC474657
0.8276	Intermediate Similarity	NPC186145
0.8272	Intermediate Similarity	NPC14112
0.8272	Intermediate Similarity	NPC93662
0.8272	Intermediate Similarity	NPC78067
0.8272	Intermediate Similarity	NPC278091
0.8272	Intermediate Similarity	NPC86305
0.825	Intermediate Similarity	NPC304499
0.8242	Intermediate Similarity	NPC473348
0.8235	Intermediate Similarity	NPC113978
0.8228	Intermediate Similarity	NPC111234
0.8214	Intermediate Similarity	NPC470383
0.8202	Intermediate Similarity	NPC80561
0.8202	Intermediate Similarity	NPC291484
0.8202	Intermediate Similarity	NPC11216
0.8202	Intermediate Similarity	NPC100313
0.8202	Intermediate Similarity	NPC204188
0.8202	Intermediate Similarity	NPC329596
0.8202	Intermediate Similarity	NPC3345
0.8193	Intermediate Similarity	NPC49627
0.8193	Intermediate Similarity	NPC49599
0.8182	Intermediate Similarity	NPC470542
0.8182	Intermediate Similarity	NPC67872
0.8161	Intermediate Similarity	NPC299068
0.8161	Intermediate Similarity	NPC261266
0.8148	Intermediate Similarity	NPC240235
0.8148	Intermediate Similarity	NPC103822
0.8148	Intermediate Similarity	NPC231256
0.8148	Intermediate Similarity	NPC178383
0.8148	Intermediate Similarity	NPC212879
0.8148	Intermediate Similarity	NPC70982
0.8148	Intermediate Similarity	NPC230704
0.8148	Intermediate Similarity	NPC104387
0.814	Intermediate Similarity	NPC242016
0.814	Intermediate Similarity	NPC299963
0.8118	Intermediate Similarity	NPC101462
0.8105	Intermediate Similarity	NPC31085
0.8101	Intermediate Similarity	NPC63588
0.8101	Intermediate Similarity	NPC251201
0.8101	Intermediate Similarity	NPC232925
0.8101	Intermediate Similarity	NPC283316
0.8095	Intermediate Similarity	NPC26117
0.8095	Intermediate Similarity	NPC322313
0.8095	Intermediate Similarity	NPC102253
0.8095	Intermediate Similarity	NPC236237
0.809	Intermediate Similarity	NPC74258
0.8072	Intermediate Similarity	NPC167037
0.8072	Intermediate Similarity	NPC6978
0.8072	Intermediate Similarity	NPC138621
0.8072	Intermediate Similarity	NPC244385
0.8068	Intermediate Similarity	NPC470620
0.8068	Intermediate Similarity	NPC477600
0.8065	Intermediate Similarity	NPC477226
0.8065	Intermediate Similarity	NPC274793
0.8049	Intermediate Similarity	NPC63958
0.8049	Intermediate Similarity	NPC91573
0.8046	Intermediate Similarity	NPC470360
0.8041	Intermediate Similarity	NPC37600
0.8025	Intermediate Similarity	NPC49168
0.8025	Intermediate Similarity	NPC25511
0.8025	Intermediate Similarity	NPC254509
0.8025	Intermediate Similarity	NPC145552
0.8025	Intermediate Similarity	NPC62657
0.8025	Intermediate Similarity	NPC192638
0.8025	Intermediate Similarity	NPC5046
0.8025	Intermediate Similarity	NPC196358
0.8022	Intermediate Similarity	NPC296620
0.8021	Intermediate Similarity	NPC471467
0.8	Intermediate Similarity	NPC121218
0.8	Intermediate Similarity	NPC23852
0.8	Intermediate Similarity	NPC470168
0.8	Intermediate Similarity	NPC209620
0.8	Intermediate Similarity	NPC253886
0.8	Intermediate Similarity	NPC144486
0.8	Intermediate Similarity	NPC476646
0.8	Intermediate Similarity	NPC10274
0.7978	Intermediate Similarity	NPC474668
0.7978	Intermediate Similarity	NPC473436
0.7978	Intermediate Similarity	NPC2158
0.7978	Intermediate Similarity	NPC471952
0.7976	Intermediate Similarity	NPC472463
0.7976	Intermediate Similarity	NPC1319
0.7976	Intermediate Similarity	NPC273410
0.7976	Intermediate Similarity	NPC80530
0.7975	Intermediate Similarity	NPC234511
0.7975	Intermediate Similarity	NPC477820
0.7957	Intermediate Similarity	NPC288970
0.7955	Intermediate Similarity	NPC71520
0.7955	Intermediate Similarity	NPC145245
0.7955	Intermediate Similarity	NPC269058
0.7952	Intermediate Similarity	NPC185915
0.7952	Intermediate Similarity	NPC105208
0.7952	Intermediate Similarity	NPC192046
0.7952	Intermediate Similarity	NPC128951
0.7952	Intermediate Similarity	NPC477227
0.7952	Intermediate Similarity	NPC302578
0.7931	Intermediate Similarity	NPC185568
0.7931	Intermediate Similarity	NPC205845
0.7927	Intermediate Similarity	NPC144075
0.7927	Intermediate Similarity	NPC200243
0.7927	Intermediate Similarity	NPC317242
0.7917	Intermediate Similarity	NPC177701
0.7912	Intermediate Similarity	NPC275671
0.7912	Intermediate Similarity	NPC219516
0.7907	Intermediate Similarity	NPC50964
0.7907	Intermediate Similarity	NPC472504
0.7907	Intermediate Similarity	NPC218616
0.7907	Intermediate Similarity	NPC296701
0.7907	Intermediate Similarity	NPC248886
0.7901	Intermediate Similarity	NPC470610

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 NPC256567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	2358
0.2-0.3	4288
0.3-0.4	1642
0.4-0.5	303
0.5-0.6	181
0.6-0.7	180
0.7-0.8	26
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8095	Intermediate Similarity	NPD7525	Registered
0.7765	Intermediate Similarity	NPD6929	Approved
0.7727	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6931	Approved
0.7674	Intermediate Similarity	NPD6930	Phase 2
0.7667	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6695	Phase 3
0.7529	Intermediate Similarity	NPD6925	Approved
0.7529	Intermediate Similarity	NPD5776	Phase 2
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD7339	Approved
0.7442	Intermediate Similarity	NPD7145	Approved
0.7356	Intermediate Similarity	NPD7645	Phase 2
0.7317	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7524	Approved
0.7283	Intermediate Similarity	NPD7750	Discontinued
0.7273	Intermediate Similarity	NPD7514	Phase 3
0.7253	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6893	Approved
0.7191	Intermediate Similarity	NPD6902	Approved
0.7172	Intermediate Similarity	NPD7639	Approved
0.7172	Intermediate Similarity	NPD7640	Approved
0.7126	Intermediate Similarity	NPD6932	Approved
0.7079	Intermediate Similarity	NPD7332	Phase 2
0.7079	Intermediate Similarity	NPD4748	Discontinued
0.7071	Intermediate Similarity	NPD7638	Approved
0.7033	Intermediate Similarity	NPD4788	Approved
0.703	Intermediate Similarity	NPD5211	Phase 2
0.7024	Intermediate Similarity	NPD4787	Phase 1
0.7	Intermediate Similarity	NPD6898	Phase 1
0.6979	Remote Similarity	NPD7087	Discontinued
0.6979	Remote Similarity	NPD8035	Phase 2
0.6979	Remote Similarity	NPD8034	Phase 2
0.6977	Remote Similarity	NPD4784	Approved
0.6977	Remote Similarity	NPD6924	Approved
0.6977	Remote Similarity	NPD6926	Approved
0.6977	Remote Similarity	NPD4785	Approved
0.697	Remote Similarity	NPD4755	Approved
0.6966	Remote Similarity	NPD6683	Phase 2
0.6957	Remote Similarity	NPD4786	Approved
0.6941	Remote Similarity	NPD4243	Approved
0.6907	Remote Similarity	NPD4202	Approved
0.6893	Remote Similarity	NPD5141	Approved
0.6889	Remote Similarity	NPD6928	Phase 2
0.6854	Remote Similarity	NPD6115	Approved
0.6854	Remote Similarity	NPD6697	Approved
0.6854	Remote Similarity	NPD6118	Approved
0.6854	Remote Similarity	NPD6114	Approved
0.6832	Remote Similarity	NPD4696	Approved
0.6832	Remote Similarity	NPD5285	Approved
0.6832	Remote Similarity	NPD5286	Approved
0.6832	Remote Similarity	NPD4700	Approved
0.6818	Remote Similarity	NPD6933	Approved
0.6771	Remote Similarity	NPD5328	Approved
0.6757	Remote Similarity	NPD7327	Approved
0.6757	Remote Similarity	NPD7328	Approved
0.6744	Remote Similarity	NPD7151	Approved
0.6744	Remote Similarity	NPD7152	Approved
0.6744	Remote Similarity	NPD7150	Approved
0.6742	Remote Similarity	NPD6116	Phase 1
0.6739	Remote Similarity	NPD3667	Approved
0.6726	Remote Similarity	NPD8033	Approved
0.6706	Remote Similarity	NPD6923	Approved
0.6706	Remote Similarity	NPD6922	Approved
0.6703	Remote Similarity	NPD7509	Discontinued
0.6699	Remote Similarity	NPD7632	Discontinued
0.6699	Remote Similarity	NPD5225	Approved
0.6699	Remote Similarity	NPD5226	Approved
0.6699	Remote Similarity	NPD5224	Approved
0.6699	Remote Similarity	NPD4633	Approved
0.6696	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6635	Remote Similarity	NPD5175	Approved
0.6635	Remote Similarity	NPD5174	Approved
0.6633	Remote Similarity	NPD6079	Approved
0.6633	Remote Similarity	NPD7637	Suspended
0.6632	Remote Similarity	NPD3618	Phase 1
0.6629	Remote Similarity	NPD6117	Approved
0.6628	Remote Similarity	NPD7144	Approved
0.6628	Remote Similarity	NPD7143	Approved
0.6602	Remote Similarity	NPD5223	Approved
0.6598	Remote Similarity	NPD4753	Phase 2
0.6596	Remote Similarity	NPD3665	Phase 1
0.6596	Remote Similarity	NPD3666	Approved
0.6596	Remote Similarity	NPD3133	Approved
0.6579	Remote Similarity	NPD8296	Approved
0.6579	Remote Similarity	NPD8380	Approved
0.6579	Remote Similarity	NPD8335	Approved
0.6579	Remote Similarity	NPD8378	Approved
0.6579	Remote Similarity	NPD8379	Approved
0.6574	Remote Similarity	NPD4634	Approved
0.6566	Remote Similarity	NPD6399	Phase 3
0.6552	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8133	Approved
0.6542	Remote Similarity	NPD6899	Approved
0.6542	Remote Similarity	NPD7320	Approved
0.6542	Remote Similarity	NPD6881	Approved
0.6531	Remote Similarity	NPD7136	Phase 2
0.6517	Remote Similarity	NPD4190	Phase 3
0.6517	Remote Similarity	NPD5275	Approved
0.6517	Remote Similarity	NPD8264	Approved
0.6517	Remote Similarity	NPD3703	Phase 2
0.6509	Remote Similarity	NPD4767	Approved
0.6509	Remote Similarity	NPD4768	Approved
0.6491	Remote Similarity	NPD8294	Approved
0.6491	Remote Similarity	NPD8377	Approved
0.6484	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6373	Approved
0.6481	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD4754	Approved
0.6465	Remote Similarity	NPD7515	Phase 2
0.6449	Remote Similarity	NPD5697	Approved
0.6449	Remote Similarity	NPD5701	Approved
0.6442	Remote Similarity	NPD4159	Approved
0.6437	Remote Similarity	NPD4245	Approved
0.6437	Remote Similarity	NPD4244	Approved
0.6422	Remote Similarity	NPD6883	Approved
0.6422	Remote Similarity	NPD7102	Approved
0.6422	Remote Similarity	NPD7290	Approved
0.6413	Remote Similarity	NPD4195	Approved
0.6404	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8171	Discontinued
0.6389	Remote Similarity	NPD5128	Approved
0.6389	Remote Similarity	NPD4730	Approved
0.6389	Remote Similarity	NPD4729	Approved
0.6373	Remote Similarity	NPD5222	Approved
0.6373	Remote Similarity	NPD5221	Approved
0.6373	Remote Similarity	NPD4697	Phase 3
0.6373	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6869	Approved
0.6364	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD6649	Approved
0.6364	Remote Similarity	NPD6847	Approved
0.6364	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD6617	Approved
0.633	Remote Similarity	NPD6012	Approved
0.633	Remote Similarity	NPD6013	Approved
0.633	Remote Similarity	NPD6014	Approved
0.6322	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD3698	Phase 2
0.6311	Remote Similarity	NPD5173	Approved
0.6311	Remote Similarity	NPD6083	Phase 2
0.6311	Remote Similarity	NPD6084	Phase 2
0.6306	Remote Similarity	NPD8297	Approved
0.6306	Remote Similarity	NPD6882	Approved
0.6296	Remote Similarity	NPD6412	Phase 2
0.6275	Remote Similarity	NPD4629	Approved
0.6275	Remote Similarity	NPD5210	Approved
0.6273	Remote Similarity	NPD5250	Approved
0.6273	Remote Similarity	NPD5247	Approved
0.6273	Remote Similarity	NPD5251	Approved
0.6273	Remote Similarity	NPD5248	Approved
0.6273	Remote Similarity	NPD5249	Phase 3
0.6263	Remote Similarity	NPD6051	Approved
0.625	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD3668	Phase 3
0.6239	Remote Similarity	NPD6011	Approved
0.6218	Remote Similarity	NPD7507	Approved
0.6216	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5217	Approved
0.6216	Remote Similarity	NPD5216	Approved
0.6216	Remote Similarity	NPD5215	Approved
0.6211	Remote Similarity	NPD4221	Approved
0.6211	Remote Similarity	NPD4223	Phase 3
0.6207	Remote Similarity	NPD6054	Approved
0.6207	Remote Similarity	NPD6059	Approved
0.6204	Remote Similarity	NPD6008	Approved
0.6198	Remote Similarity	NPD7319	Approved
0.6186	Remote Similarity	NPD5329	Approved
0.6176	Remote Similarity	NPD7748	Approved
0.617	Remote Similarity	NPD4822	Approved
0.617	Remote Similarity	NPD4819	Approved
0.617	Remote Similarity	NPD4820	Approved
0.617	Remote Similarity	NPD4821	Approved
0.6154	Remote Similarity	NPD7503	Approved
0.6154	Remote Similarity	NPD7902	Approved
0.6129	Remote Similarity	NPD4271	Approved
0.6129	Remote Similarity	NPD4268	Approved
0.6126	Remote Similarity	NPD5135	Approved
0.6126	Remote Similarity	NPD5169	Approved
0.6126	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6370	Approved
0.6091	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6009	Approved
0.6087	Remote Similarity	NPD7115	Discovery
0.6082	Remote Similarity	NPD4197	Approved
0.6071	Remote Similarity	NPD5127	Approved
0.6068	Remote Similarity	NPD6319	Approved
0.6067	Remote Similarity	NPD4789	Approved
0.604	Remote Similarity	NPD6700	Approved
0.604	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5361	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