NPASS Compound

Structure

NPC472704 OpenBabel07101718272D 27 28 0 0 1 0 0 0 0 0999 V2000 -0.7957 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1554 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0622 -3.5000 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 2.5981 -0.5000 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 1.7321 -0.0000 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3479 -1.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 5 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 27 1 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 20 3 1 6 0 0 0 20 26 1 0 0 0 0 21 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.19
Volume:	391.582
LogP:	2.838
LogD:	1.767
LogS:	-4.431
# Rotatable Bonds:	8
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	3.595
Fsp3:	0.571
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:	-5.307
MDCK Permeability:	4.154865746386349e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.049
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	78.15095520019531%
Volume Distribution (VD):	0.168
Pgp-substrate:	14.052854537963867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.473
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.671
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	9.166
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.496
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.041
Carcinogencity:	0.01
Eye Corrosion:	0.006
Eye Irritation:	0.07
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC472704

Natural Product ID:	NPC472704
*Common Name:**	WOXSROLDXSRULX-NHCUHLMSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WOXSROLDXSRULX-NHCUHLMSSA-N
Standard InCHI:	InChI=1S/C21H28O6/c1-19(2)11-16(22)12-21(19,4)15-7-5-14(6-8-15)18(25)27-10-9-20(3,26)13-17(23)24/h5-8,26H,9-13H2,1-4H3,(H,23,24)/t20-,21-/m1/s1
SMILES:	CC1(CC(=O)CC1(C)C2=CC=C(C=C2)C(=O)OCCC(C)(CC(=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581620
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32768	basidiomycete deconica sp. 471	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25871540]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[489841]

☑ 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 NPC472704 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	231
0.1-0.2	954
0.2-0.3	2165
0.3-0.4	5660
0.4-0.5	10936
0.5-0.6	12483
0.6-0.7	9009
0.7-0.8	1137
0.8-0.85	110
0.85-0.9	8
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC472703
0.9583	High Similarity	NPC472706
0.9032	High Similarity	NPC472707
0.8507	High Similarity	NPC475413
0.8507	High Similarity	NPC474303
0.8507	High Similarity	NPC242355
0.8507	High Similarity	NPC473497
0.8462	Intermediate Similarity	NPC233860
0.8462	Intermediate Similarity	NPC239358
0.8462	Intermediate Similarity	NPC233692
0.8455	Intermediate Similarity	NPC472708
0.845	Intermediate Similarity	NPC82712
0.845	Intermediate Similarity	NPC272946
0.8397	Intermediate Similarity	NPC472248
0.8382	Intermediate Similarity	NPC45307
0.8376	Intermediate Similarity	NPC249811
0.8333	Intermediate Similarity	NPC28836
0.8333	Intermediate Similarity	NPC477359
0.8333	Intermediate Similarity	NPC311492
0.8333	Intermediate Similarity	NPC477368
0.8333	Intermediate Similarity	NPC153617
0.8305	Intermediate Similarity	NPC469636
0.8284	Intermediate Similarity	NPC86772
0.8271	Intermediate Similarity	NPC79699
0.8271	Intermediate Similarity	NPC477367
0.8271	Intermediate Similarity	NPC200154
0.8271	Intermediate Similarity	NPC232888
0.8258	Intermediate Similarity	NPC477364
0.8244	Intermediate Similarity	NPC72915
0.8222	Intermediate Similarity	NPC272523
0.8222	Intermediate Similarity	NPC325805
0.8209	Intermediate Similarity	NPC202729
0.8203	Intermediate Similarity	NPC295664
0.8201	Intermediate Similarity	NPC170668
0.8195	Intermediate Similarity	NPC472250
0.819	Intermediate Similarity	NPC301943
0.819	Intermediate Similarity	NPC474365
0.8189	Intermediate Similarity	NPC223351
0.8168	Intermediate Similarity	NPC475508
0.8168	Intermediate Similarity	NPC42234
0.816	Intermediate Similarity	NPC204784
0.8148	Intermediate Similarity	NPC27721
0.8143	Intermediate Similarity	NPC205389
0.8134	Intermediate Similarity	NPC265459
0.8134	Intermediate Similarity	NPC270364
0.8134	Intermediate Similarity	NPC475262
0.8134	Intermediate Similarity	NPC290833
0.813	Intermediate Similarity	NPC149691
0.8116	Intermediate Similarity	NPC153214
0.8115	Intermediate Similarity	NPC307651
0.8115	Intermediate Similarity	NPC474363
0.8102	Intermediate Similarity	NPC77493
0.8102	Intermediate Similarity	NPC187566
0.8088	Intermediate Similarity	NPC170718
0.8088	Intermediate Similarity	NPC473301
0.8074	Intermediate Similarity	NPC472551
0.8074	Intermediate Similarity	NPC472545
0.8074	Intermediate Similarity	NPC52523
0.8074	Intermediate Similarity	NPC285221
0.8074	Intermediate Similarity	NPC194769
0.8074	Intermediate Similarity	NPC217673
0.8071	Intermediate Similarity	NPC469513
0.8062	Intermediate Similarity	NPC246166
0.806	Intermediate Similarity	NPC48929
0.806	Intermediate Similarity	NPC329913
0.806	Intermediate Similarity	NPC126516
0.806	Intermediate Similarity	NPC203486
0.8045	Intermediate Similarity	NPC477360
0.8043	Intermediate Similarity	NPC183540
0.8033	Intermediate Similarity	NPC128368
0.8031	Intermediate Similarity	NPC50872
0.803	Intermediate Similarity	NPC147561
0.803	Intermediate Similarity	NPC471832
0.8028	Intermediate Similarity	NPC232583
0.8028	Intermediate Similarity	NPC25484
0.8028	Intermediate Similarity	NPC477099
0.8028	Intermediate Similarity	NPC477101
0.8028	Intermediate Similarity	NPC477097
0.8017	Intermediate Similarity	NPC70624
0.8015	Intermediate Similarity	NPC115797
0.8015	Intermediate Similarity	NPC51448
0.8015	Intermediate Similarity	NPC39549
0.8	Intermediate Similarity	NPC127857
0.8	Intermediate Similarity	NPC472247
0.8	Intermediate Similarity	NPC470765
0.7986	Intermediate Similarity	NPC95449
0.7986	Intermediate Similarity	NPC82467
0.7986	Intermediate Similarity	NPC477094
0.7986	Intermediate Similarity	NPC477096
0.7984	Intermediate Similarity	NPC228739
0.7984	Intermediate Similarity	NPC85511
0.7967	Intermediate Similarity	NPC153053
0.7956	Intermediate Similarity	NPC9905
0.7956	Intermediate Similarity	NPC276652
0.7953	Intermediate Similarity	NPC473243
0.7951	Intermediate Similarity	NPC321852
0.7949	Intermediate Similarity	NPC25458
0.7939	Intermediate Similarity	NPC204579
0.7939	Intermediate Similarity	NPC110211
0.7939	Intermediate Similarity	NPC473220
0.7939	Intermediate Similarity	NPC470753
0.7931	Intermediate Similarity	NPC203925
0.7931	Intermediate Similarity	NPC325497
0.7926	Intermediate Similarity	NPC134937
0.7926	Intermediate Similarity	NPC324898
0.7926	Intermediate Similarity	NPC298547
0.7914	Intermediate Similarity	NPC51181
0.791	Intermediate Similarity	NPC125153
0.7903	Intermediate Similarity	NPC306740
0.7902	Intermediate Similarity	NPC125033
0.7899	Intermediate Similarity	NPC475660
0.7899	Intermediate Similarity	NPC251294
0.7899	Intermediate Similarity	NPC275592
0.7899	Intermediate Similarity	NPC472547
0.7899	Intermediate Similarity	NPC162613
0.7899	Intermediate Similarity	NPC97667
0.7899	Intermediate Similarity	NPC171207
0.7899	Intermediate Similarity	NPC87934
0.7899	Intermediate Similarity	NPC100913
0.7899	Intermediate Similarity	NPC90614
0.7895	Intermediate Similarity	NPC194979
0.7887	Intermediate Similarity	NPC132652
0.7886	Intermediate Similarity	NPC474176
0.7872	Intermediate Similarity	NPC25043
0.7872	Intermediate Similarity	NPC134131
0.7869	Intermediate Similarity	NPC476003
0.7869	Intermediate Similarity	NPC210089
0.7869	Intermediate Similarity	NPC260818
0.7868	Intermediate Similarity	NPC279637
0.7868	Intermediate Similarity	NPC149401
0.7863	Intermediate Similarity	NPC275576
0.7863	Intermediate Similarity	NPC477366
0.7863	Intermediate Similarity	NPC9180
0.7863	Intermediate Similarity	NPC476033
0.7863	Intermediate Similarity	NPC121272
0.7863	Intermediate Similarity	NPC100402
0.7863	Intermediate Similarity	NPC476599
0.7862	Intermediate Similarity	NPC477098
0.7862	Intermediate Similarity	NPC477100
0.7857	Intermediate Similarity	NPC45794
0.7851	Intermediate Similarity	NPC17417
0.7851	Intermediate Similarity	NPC10251
0.7851	Intermediate Similarity	NPC265407
0.7851	Intermediate Similarity	NPC83628
0.7847	Intermediate Similarity	NPC471103
0.7847	Intermediate Similarity	NPC51602
0.7846	Intermediate Similarity	NPC477362
0.7845	Intermediate Similarity	NPC78701
0.7845	Intermediate Similarity	NPC35448
0.7842	Intermediate Similarity	NPC97947
0.7842	Intermediate Similarity	NPC118080
0.7842	Intermediate Similarity	NPC224491
0.7842	Intermediate Similarity	NPC291599
0.7842	Intermediate Similarity	NPC473654
0.7842	Intermediate Similarity	NPC41481
0.7842	Intermediate Similarity	NPC87448
0.7842	Intermediate Similarity	NPC27377
0.7842	Intermediate Similarity	NPC472576
0.7842	Intermediate Similarity	NPC266374
0.7842	Intermediate Similarity	NPC16912
0.784	Intermediate Similarity	NPC471616
0.7832	Intermediate Similarity	NPC250046
0.7832	Intermediate Similarity	NPC60509
0.7832	Intermediate Similarity	NPC81698
0.7829	Intermediate Similarity	NPC269923
0.7829	Intermediate Similarity	NPC167323
0.7817	Intermediate Similarity	NPC477095
0.7817	Intermediate Similarity	NPC475552
0.7817	Intermediate Similarity	NPC478263
0.781	Intermediate Similarity	NPC477358
0.7805	Intermediate Similarity	NPC82899
0.7805	Intermediate Similarity	NPC270699
0.7803	Intermediate Similarity	NPC169913
0.7803	Intermediate Similarity	NPC477357
0.7803	Intermediate Similarity	NPC477365
0.7797	Intermediate Similarity	NPC188895
0.7797	Intermediate Similarity	NPC304873
0.7794	Intermediate Similarity	NPC474608
0.7787	Intermediate Similarity	NPC251854
0.7787	Intermediate Similarity	NPC196246
0.7787	Intermediate Similarity	NPC214067
0.7787	Intermediate Similarity	NPC93084
0.7786	Intermediate Similarity	NPC472546
0.7786	Intermediate Similarity	NPC192658
0.7778	Intermediate Similarity	NPC198455
0.7778	Intermediate Similarity	NPC217621
0.7778	Intermediate Similarity	NPC165260
0.7778	Intermediate Similarity	NPC161239
0.7778	Intermediate Similarity	NPC238370
0.7778	Intermediate Similarity	NPC146351
0.7778	Intermediate Similarity	NPC7095
0.7778	Intermediate Similarity	NPC112216
0.7778	Intermediate Similarity	NPC91730
0.777	Intermediate Similarity	NPC477904
0.777	Intermediate Similarity	NPC183270
0.7769	Intermediate Similarity	NPC56493
0.7769	Intermediate Similarity	NPC20485
0.7762	Intermediate Similarity	NPC217918
0.776	Intermediate Similarity	NPC221275
0.776	Intermediate Similarity	NPC476357

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 NPC472704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	736
0.2-0.3	1405
0.3-0.4	2588
0.4-0.5	2470
0.5-0.6	1279
0.6-0.7	422
0.7-0.8	44
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
0.803	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD7236	Approved
0.7851	Intermediate Similarity	NPD2182	Approved
0.7829	Intermediate Similarity	NPD6287	Discontinued
0.7724	Intermediate Similarity	NPD7239	Suspended
0.7674	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7008	Discontinued
0.7619	Intermediate Similarity	NPD5951	Approved
0.7619	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4628	Phase 3
0.7561	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD4198	Discontinued
0.7521	Intermediate Similarity	NPD164	Approved
0.7519	Intermediate Similarity	NPD9545	Approved
0.7481	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD1238	Approved
0.7479	Intermediate Similarity	NPD2066	Phase 3
0.7436	Intermediate Similarity	NPD1693	Approved
0.7407	Intermediate Similarity	NPD6085	Phase 2
0.7407	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7799	Discontinued
0.7383	Intermediate Similarity	NPD6599	Discontinued
0.7381	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9493	Approved
0.7319	Intermediate Similarity	NPD3764	Approved
0.7295	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1929	Approved
0.7295	Intermediate Similarity	NPD6647	Phase 2
0.7295	Intermediate Similarity	NPD1930	Approved
0.7273	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2652	Approved
0.7266	Intermediate Similarity	NPD2650	Approved
0.7266	Intermediate Similarity	NPD7961	Discontinued
0.7265	Intermediate Similarity	NPD1088	Approved
0.7255	Intermediate Similarity	NPD7058	Phase 2
0.7255	Intermediate Similarity	NPD7057	Phase 3
0.7239	Intermediate Similarity	NPD3972	Approved
0.7214	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1932	Approved
0.7209	Intermediate Similarity	NPD2629	Approved
0.7177	Intermediate Similarity	NPD5048	Discontinued
0.7165	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2532	Approved
0.7162	Intermediate Similarity	NPD2534	Approved
0.7162	Intermediate Similarity	NPD2533	Approved
0.7153	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD1778	Approved
0.7133	Intermediate Similarity	NPD2799	Discontinued
0.7132	Intermediate Similarity	NPD6010	Discontinued
0.7121	Intermediate Similarity	NPD7741	Discontinued
0.712	Intermediate Similarity	NPD6685	Approved
0.7114	Intermediate Similarity	NPD6273	Approved
0.7111	Intermediate Similarity	NPD9717	Approved
0.7097	Intermediate Similarity	NPD1237	Approved
0.7094	Intermediate Similarity	NPD1090	Approved
0.7094	Intermediate Similarity	NPD1089	Approved
0.7094	Intermediate Similarity	NPD9256	Approved
0.7094	Intermediate Similarity	NPD1086	Approved
0.7094	Intermediate Similarity	NPD9258	Approved
0.7087	Intermediate Similarity	NPD2067	Discontinued
0.7083	Intermediate Similarity	NPD1989	Approved
0.7083	Intermediate Similarity	NPD1551	Phase 2
0.7071	Intermediate Similarity	NPD2313	Discontinued
0.7059	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6858	Approved
0.7054	Intermediate Similarity	NPD7094	Approved
0.705	Intermediate Similarity	NPD6832	Phase 2
0.7047	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7610	Discontinued
0.7029	Intermediate Similarity	NPD2798	Approved
0.7014	Intermediate Similarity	NPD7033	Discontinued
0.7014	Intermediate Similarity	NPD4308	Phase 3
0.7013	Intermediate Similarity	NPD7819	Suspended
0.7009	Intermediate Similarity	NPD800	Approved
0.7008	Intermediate Similarity	NPD2329	Discontinued
0.7007	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1607	Approved
0.6993	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7009	Phase 2
0.698	Remote Similarity	NPD6799	Approved
0.6974	Remote Similarity	NPD3226	Approved
0.6974	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7458	Discontinued
0.6966	Remote Similarity	NPD2935	Discontinued
0.696	Remote Similarity	NPD5909	Discontinued
0.6953	Remote Similarity	NPD1317	Discontinued
0.695	Remote Similarity	NPD411	Approved
0.6944	Remote Similarity	NPD2567	Approved
0.6944	Remote Similarity	NPD2569	Approved
0.6923	Remote Similarity	NPD230	Phase 1
0.6918	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6005	Phase 3
0.6918	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6004	Phase 3
0.6918	Remote Similarity	NPD6002	Phase 3
0.6918	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1202	Approved
0.6906	Remote Similarity	NPD5647	Approved
0.6903	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7713	Phase 3
0.6897	Remote Similarity	NPD1510	Phase 2
0.6897	Remote Similarity	NPD7305	Phase 1
0.6897	Remote Similarity	NPD9259	Approved
0.6897	Remote Similarity	NPD9257	Approved
0.6892	Remote Similarity	NPD7003	Approved
0.6884	Remote Similarity	NPD1876	Approved
0.6883	Remote Similarity	NPD7411	Suspended
0.688	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5765	Approved
0.6871	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6637	Approved
0.6861	Remote Similarity	NPD1608	Approved
0.6853	Remote Similarity	NPD4307	Phase 2
0.6853	Remote Similarity	NPD1240	Approved
0.6849	Remote Similarity	NPD2796	Approved
0.6838	Remote Similarity	NPD1087	Approved
0.6835	Remote Similarity	NPD1203	Approved
0.6831	Remote Similarity	NPD3268	Approved
0.6829	Remote Similarity	NPD9495	Approved
0.6815	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD9264	Approved
0.6797	Remote Similarity	NPD9267	Approved
0.6797	Remote Similarity	NPD9263	Approved
0.6788	Remote Similarity	NPD8368	Discontinued
0.6786	Remote Similarity	NPD1019	Discontinued
0.6783	Remote Similarity	NPD6663	Approved
0.6779	Remote Similarity	NPD3750	Approved
0.6779	Remote Similarity	NPD8166	Discontinued
0.6772	Remote Similarity	NPD7075	Discontinued
0.6766	Remote Similarity	NPD8407	Phase 2
0.6765	Remote Similarity	NPD5306	Approved
0.6765	Remote Similarity	NPD5305	Approved
0.6765	Remote Similarity	NPD5126	Approved
0.6765	Remote Similarity	NPD5125	Phase 3
0.6757	Remote Similarity	NPD1549	Phase 2
0.675	Remote Similarity	NPD1239	Approved
0.6744	Remote Similarity	NPD74	Approved
0.6744	Remote Similarity	NPD9266	Approved
0.6738	Remote Similarity	NPD5736	Approved
0.6735	Remote Similarity	NPD5405	Approved
0.6735	Remote Similarity	NPD5406	Approved
0.6735	Remote Similarity	NPD5408	Approved
0.6735	Remote Similarity	NPD5404	Approved
0.6718	Remote Similarity	NPD6912	Phase 3
0.6718	Remote Similarity	NPD9508	Approved
0.6715	Remote Similarity	NPD4106	Approved
0.6715	Remote Similarity	NPD4136	Approved
0.6715	Remote Similarity	NPD4135	Approved
0.6714	Remote Similarity	NPD2797	Approved
0.6713	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2800	Approved
0.6711	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7768	Phase 2
0.6692	Remote Similarity	NPD4233	Approved
0.6692	Remote Similarity	NPD4766	Approved
0.6692	Remote Similarity	NPD4234	Approved
0.6691	Remote Similarity	NPD182	Clinical (unspecified phase)
0.669	Remote Similarity	NPD447	Suspended
0.669	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6355	Discontinued
0.6689	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2344	Approved
0.6688	Remote Similarity	NPD5761	Phase 2
0.6688	Remote Similarity	NPD5760	Phase 2
0.6686	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD4807	Approved
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4806	Approved
0.6667	Remote Similarity	NPD7714	Approved
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD5277	Phase 2
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD3672	Approved
0.6667	Remote Similarity	NPD7715	Approved
0.6645	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2199	Approved
0.6643	Remote Similarity	NPD2198	Approved
0.6643	Remote Similarity	NPD1283	Approved
0.6642	Remote Similarity	NPD3019	Approved
0.6642	Remote Similarity	NPD2932	Approved
0.6642	Remote Similarity	NPD17	Approved
0.6638	Remote Similarity	NPD9491	Approved
0.6626	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6801	Discontinued
0.6623	Remote Similarity	NPD5403	Approved
0.6623	Remote Similarity	NPD920	Approved
0.6622	Remote Similarity	NPD6100	Approved

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