NPASS Compound

Structure

NPC471818 OpenBabel07101718192D 28 29 0 0 1 0 0 0 0 0999 V2000 3.7910 -5.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2795 -4.4768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9820 -3.8639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9486 -3.8639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7543 -0.6184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7910 -4.9601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3025 -1.5768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0772 -1.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0109 -1.1434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5448 0.2447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3025 -2.5434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4653 -1.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6835 0.6835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2795 -3.5101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3936 -0.7101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9538 -4.4768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6944 -1.8270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9538 -3.5101 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.6282 -2.5434 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4389 -0.8613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4653 -3.0268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6282 -1.5768 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4424 -3.0268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1167 -4.9601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4442 -2.7607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7226 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 2.1167 -3.0268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 14 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 6 16 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 27 1 0 0 0 0 14 23 2 0 0 0 0 14 28 1 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 24 2 0 0 0 0 17 22 1 0 0 0 0 17 25 2 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 6 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 22 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	411.514
LogP:	3.12
LogD:	2.699
LogS:	-3.787
# Rotatable Bonds:	9
TPSA:	93.81
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	4.363
Fsp3:	0.682
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:	-4.924
MDCK Permeability:	2.7869024052051827e-05
Pgp-inhibitor:	0.896
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.29

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	89.03156280517578%
Volume Distribution (VD):	0.877
Pgp-substrate:	8.56581974029541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.306
CYP2C9-inhibitor:	0.479
CYP2C9-substrate:	0.679
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.283
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	12.959
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.25
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.745
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.072
Carcinogencity:	0.929
Eye Corrosion:	0.024
Eye Irritation:	0.065
Respiratory Toxicity:	0.431

Download Data

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

Natural Product: NPC471818

Natural Product ID:	NPC471818
*Common Name:**	Lagopsin G
IUPAC Name:	[2-oxo-1-[(1S,6S)-2,2,6-trimethyl-6-[3-(5-oxo-2H-furan-4-yl)propanoyl]cyclohexyl]butyl] acetate
Synonyms:
Standard InCHIKey:	QSCKCWXZUDXSMG-FGTDEGFTSA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-6-16(24)18(28-14(2)23)19-21(3,4)11-7-12-22(19,5)17(25)9-8-15-10-13-27-20(15)26/h10,18-19H,6-9,11-13H2,1-5H3/t18?,19-,22+/m0/s1
SMILES:	CCC(=O)C([C@H]1C(C)(C)CCC[C@]1(C)C(=O)CCC1=CCOC1=O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234605
PubChem CID:	86302557
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24707938]
NPO17287	Lagopsis supina	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34900.0	nM	PMID[490267]

☑ 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 NPC471818 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	216
0.1-0.2	1309
0.2-0.3	5492
0.3-0.4	12236
0.4-0.5	10971
0.5-0.6	7014
0.6-0.7	4636
0.7-0.8	781
0.8-0.85	35
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC149869
0.8791	High Similarity	NPC148463
0.8791	High Similarity	NPC476596
0.8681	High Similarity	NPC476597
0.8681	High Similarity	NPC476598
0.8621	High Similarity	NPC474359
0.8523	High Similarity	NPC189311
0.8444	Intermediate Similarity	NPC226863
0.8427	Intermediate Similarity	NPC220478
0.8409	Intermediate Similarity	NPC475100
0.8391	Intermediate Similarity	NPC173609
0.8391	Intermediate Similarity	NPC200513
0.8353	Intermediate Similarity	NPC471220
0.8353	Intermediate Similarity	NPC128276
0.8298	Intermediate Similarity	NPC470978
0.8298	Intermediate Similarity	NPC470974
0.8295	Intermediate Similarity	NPC222358
0.8295	Intermediate Similarity	NPC193198
0.8276	Intermediate Similarity	NPC471325
0.8235	Intermediate Similarity	NPC57744
0.8222	Intermediate Similarity	NPC38576
0.8222	Intermediate Similarity	NPC279859
0.8191	Intermediate Similarity	NPC84893
0.8152	Intermediate Similarity	NPC5509
0.8118	Intermediate Similarity	NPC27205
0.8111	Intermediate Similarity	NPC65661
0.8105	Intermediate Similarity	NPC474490
0.8085	Intermediate Similarity	NPC475657
0.8065	Intermediate Similarity	NPC476437
0.8065	Intermediate Similarity	NPC476369
0.8065	Intermediate Similarity	NPC51486
0.8061	Intermediate Similarity	NPC472643
0.8046	Intermediate Similarity	NPC469620
0.8046	Intermediate Similarity	NPC178277
0.8046	Intermediate Similarity	NPC469690
0.8046	Intermediate Similarity	NPC471299
0.8041	Intermediate Similarity	NPC54843
0.8021	Intermediate Similarity	NPC184065
0.8	Intermediate Similarity	NPC30486
0.8	Intermediate Similarity	NPC476415
0.7981	Intermediate Similarity	NPC264634
0.7978	Intermediate Similarity	NPC221231
0.7978	Intermediate Similarity	NPC471326
0.7957	Intermediate Similarity	NPC174342
0.7957	Intermediate Similarity	NPC284561
0.7938	Intermediate Similarity	NPC474343
0.7917	Intermediate Similarity	NPC295347
0.7912	Intermediate Similarity	NPC86316
0.7912	Intermediate Similarity	NPC106416
0.7912	Intermediate Similarity	NPC110405
0.7895	Intermediate Similarity	NPC139692
0.7889	Intermediate Similarity	NPC474703
0.7889	Intermediate Similarity	NPC22611
0.7882	Intermediate Similarity	NPC15499
0.7882	Intermediate Similarity	NPC117746
0.7882	Intermediate Similarity	NPC294434
0.7882	Intermediate Similarity	NPC259599
0.7879	Intermediate Similarity	NPC473384
0.7872	Intermediate Similarity	NPC212679
0.7872	Intermediate Similarity	NPC220454
0.7872	Intermediate Similarity	NPC152467
0.7872	Intermediate Similarity	NPC469595
0.7872	Intermediate Similarity	NPC8062
0.7865	Intermediate Similarity	NPC42470
0.7857	Intermediate Similarity	NPC222011
0.7849	Intermediate Similarity	NPC471047
0.7849	Intermediate Similarity	NPC215831
0.7849	Intermediate Similarity	NPC475906
0.7849	Intermediate Similarity	NPC469653
0.7849	Intermediate Similarity	NPC469631
0.7849	Intermediate Similarity	NPC469628
0.7826	Intermediate Similarity	NPC472863
0.7822	Intermediate Similarity	NPC189616
0.7816	Intermediate Similarity	NPC187568
0.7816	Intermediate Similarity	NPC41780
0.7812	Intermediate Similarity	NPC470697
0.7812	Intermediate Similarity	NPC477130
0.7812	Intermediate Similarity	NPC477129
0.781	Intermediate Similarity	NPC147180
0.7791	Intermediate Similarity	NPC244166
0.7789	Intermediate Similarity	NPC472814
0.7789	Intermediate Similarity	NPC177037
0.7789	Intermediate Similarity	NPC219874
0.7789	Intermediate Similarity	NPC473944
0.7778	Intermediate Similarity	NPC178676
0.7778	Intermediate Similarity	NPC471218
0.7778	Intermediate Similarity	NPC472644
0.7778	Intermediate Similarity	NPC94200
0.7778	Intermediate Similarity	NPC471413
0.7766	Intermediate Similarity	NPC288699
0.7766	Intermediate Similarity	NPC73995
0.7766	Intermediate Similarity	NPC280833
0.7755	Intermediate Similarity	NPC84335
0.7755	Intermediate Similarity	NPC476768
0.7755	Intermediate Similarity	NPC208094
0.7755	Intermediate Similarity	NPC69385
0.7755	Intermediate Similarity	NPC38530
0.7745	Intermediate Similarity	NPC472645
0.7742	Intermediate Similarity	NPC312561
0.7732	Intermediate Similarity	NPC209355
0.7732	Intermediate Similarity	NPC33473
0.7732	Intermediate Similarity	NPC473369
0.7717	Intermediate Similarity	NPC177932
0.7717	Intermediate Similarity	NPC30984
0.7708	Intermediate Similarity	NPC476416
0.7708	Intermediate Similarity	NPC115021
0.7701	Intermediate Similarity	NPC123360
0.7701	Intermediate Similarity	NPC473223
0.77	Intermediate Similarity	NPC310981
0.77	Intermediate Similarity	NPC471412
0.7692	Intermediate Similarity	NPC118423
0.7692	Intermediate Similarity	NPC474193
0.7692	Intermediate Similarity	NPC12283
0.7692	Intermediate Similarity	NPC475947
0.7684	Intermediate Similarity	NPC469718
0.7684	Intermediate Similarity	NPC101651
0.7684	Intermediate Similarity	NPC232426
0.7684	Intermediate Similarity	NPC159748
0.7684	Intermediate Similarity	NPC281942
0.7684	Intermediate Similarity	NPC329857
0.7677	Intermediate Similarity	NPC252295
0.7677	Intermediate Similarity	NPC176845
0.7674	Intermediate Similarity	NPC476355
0.7674	Intermediate Similarity	NPC20025
0.7674	Intermediate Similarity	NPC140287
0.7674	Intermediate Similarity	NPC474758
0.767	Intermediate Similarity	NPC475294
0.767	Intermediate Similarity	NPC133422
0.7667	Intermediate Similarity	NPC282293
0.7667	Intermediate Similarity	NPC40228
0.7667	Intermediate Similarity	NPC275507
0.7667	Intermediate Similarity	NPC14203
0.7667	Intermediate Similarity	NPC229584
0.7667	Intermediate Similarity	NPC475665
0.766	Intermediate Similarity	NPC472302
0.766	Intermediate Similarity	NPC477128
0.766	Intermediate Similarity	NPC475902
0.7653	Intermediate Similarity	NPC234993
0.7653	Intermediate Similarity	NPC134072
0.7653	Intermediate Similarity	NPC242848
0.7653	Intermediate Similarity	NPC29952
0.7647	Intermediate Similarity	NPC257618
0.764	Intermediate Similarity	NPC28319
0.764	Intermediate Similarity	NPC150646
0.7634	Intermediate Similarity	NPC261253
0.7634	Intermediate Similarity	NPC474045
0.7634	Intermediate Similarity	NPC202394
0.7634	Intermediate Similarity	NPC168248
0.7634	Intermediate Similarity	NPC261721
0.7624	Intermediate Similarity	NPC162973
0.7614	Intermediate Similarity	NPC316500
0.7609	Intermediate Similarity	NPC31086
0.7609	Intermediate Similarity	NPC238197
0.7604	Intermediate Similarity	NPC477783
0.7604	Intermediate Similarity	NPC141831
0.7604	Intermediate Similarity	NPC284185
0.7604	Intermediate Similarity	NPC65513
0.7604	Intermediate Similarity	NPC221282
0.76	Intermediate Similarity	NPC287833
0.76	Intermediate Similarity	NPC54705
0.76	Intermediate Similarity	NPC476274
0.76	Intermediate Similarity	NPC174314
0.76	Intermediate Similarity	NPC117685
0.7586	Intermediate Similarity	NPC65650
0.7582	Intermediate Similarity	NPC186276
0.7582	Intermediate Similarity	NPC268122
0.7582	Intermediate Similarity	NPC35556
0.7579	Intermediate Similarity	NPC177141
0.7579	Intermediate Similarity	NPC474844
0.7579	Intermediate Similarity	NPC168131
0.7579	Intermediate Similarity	NPC469546
0.7579	Intermediate Similarity	NPC251528
0.7576	Intermediate Similarity	NPC253826
0.7576	Intermediate Similarity	NPC475709
0.7576	Intermediate Similarity	NPC226986
0.7576	Intermediate Similarity	NPC53844
0.7576	Intermediate Similarity	NPC2049
0.7576	Intermediate Similarity	NPC110937
0.7576	Intermediate Similarity	NPC216904
0.757	Intermediate Similarity	NPC472929
0.7556	Intermediate Similarity	NPC195424
0.7556	Intermediate Similarity	NPC304795
0.7553	Intermediate Similarity	NPC478144
0.7553	Intermediate Similarity	NPC476409
0.7553	Intermediate Similarity	NPC477228
0.7551	Intermediate Similarity	NPC474947
0.7551	Intermediate Similarity	NPC183012
0.7549	Intermediate Similarity	NPC254202
0.7529	Intermediate Similarity	NPC469660
0.7528	Intermediate Similarity	NPC184737
0.7527	Intermediate Similarity	NPC474013
0.7527	Intermediate Similarity	NPC161957
0.7526	Intermediate Similarity	NPC202824
0.7526	Intermediate Similarity	NPC165383
0.7526	Intermediate Similarity	NPC475302
0.7526	Intermediate Similarity	NPC477361
0.7526	Intermediate Similarity	NPC471571
0.7525	Intermediate Similarity	NPC168319
0.7525	Intermediate Similarity	NPC475099
0.7525	Intermediate Similarity	NPC476478

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 NPC471818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1693
0.2-0.3	3929
0.3-0.4	2224
0.4-0.5	709
0.5-0.6	242
0.6-0.7	148
0.7-0.8	17
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
0.8391	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6672	Approved
0.7849	Intermediate Similarity	NPD5737	Approved
0.7717	Intermediate Similarity	NPD1694	Approved
0.7604	Intermediate Similarity	NPD5693	Phase 1
0.75	Intermediate Similarity	NPD5696	Approved
0.7447	Intermediate Similarity	NPD7334	Approved
0.7447	Intermediate Similarity	NPD7146	Approved
0.7447	Intermediate Similarity	NPD6684	Approved
0.7447	Intermediate Similarity	NPD6409	Approved
0.7447	Intermediate Similarity	NPD5330	Approved
0.7447	Intermediate Similarity	NPD7521	Approved
0.7396	Intermediate Similarity	NPD6904	Approved
0.7396	Intermediate Similarity	NPD6673	Approved
0.7396	Intermediate Similarity	NPD6080	Approved
0.732	Intermediate Similarity	NPD5785	Approved
0.7292	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6903	Approved
0.7245	Intermediate Similarity	NPD6050	Approved
0.7228	Intermediate Similarity	NPD6083	Phase 2
0.7228	Intermediate Similarity	NPD6084	Phase 2
0.7204	Intermediate Similarity	NPD5209	Approved
0.72	Intermediate Similarity	NPD5695	Phase 3
0.7191	Intermediate Similarity	NPD8039	Approved
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7103	Intermediate Similarity	NPD6881	Approved
0.7103	Intermediate Similarity	NPD6686	Approved
0.7103	Intermediate Similarity	NPD6899	Approved
0.71	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7900	Approved
0.7083	Intermediate Similarity	NPD6098	Approved
0.7075	Intermediate Similarity	NPD7128	Approved
0.7075	Intermediate Similarity	NPD6675	Approved
0.7075	Intermediate Similarity	NPD6402	Approved
0.7075	Intermediate Similarity	NPD5739	Approved
0.7071	Intermediate Similarity	NPD5694	Approved
0.7064	Intermediate Similarity	NPD6650	Approved
0.7064	Intermediate Similarity	NPD6649	Approved
0.7037	Intermediate Similarity	NPD6373	Approved
0.7037	Intermediate Similarity	NPD6372	Approved
0.703	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6614	Approved
0.7009	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD6399	Phase 3
0.699	Remote Similarity	NPD4225	Approved
0.699	Remote Similarity	NPD7638	Approved
0.6972	Remote Similarity	NPD7102	Approved
0.6972	Remote Similarity	NPD7290	Approved
0.6972	Remote Similarity	NPD6883	Approved
0.6944	Remote Similarity	NPD7320	Approved
0.6944	Remote Similarity	NPD6011	Approved
0.6931	Remote Similarity	NPD7748	Approved
0.6923	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.6909	Remote Similarity	NPD6617	Approved
0.6909	Remote Similarity	NPD6847	Approved
0.6909	Remote Similarity	NPD8130	Phase 1
0.6909	Remote Similarity	NPD6869	Approved
0.6893	Remote Similarity	NPD7902	Approved
0.6881	Remote Similarity	NPD6014	Approved
0.6881	Remote Similarity	NPD6012	Approved
0.6881	Remote Similarity	NPD6013	Approved
0.6863	Remote Similarity	NPD5210	Approved
0.6863	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4629	Approved
0.6852	Remote Similarity	NPD5701	Approved
0.6847	Remote Similarity	NPD6882	Approved
0.6847	Remote Similarity	NPD8297	Approved
0.6837	Remote Similarity	NPD3573	Approved
0.6809	Remote Similarity	NPD4695	Discontinued
0.6804	Remote Similarity	NPD5363	Approved
0.6796	Remote Similarity	NPD7732	Phase 3
0.6774	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7115	Discovery
0.6735	Remote Similarity	NPD5279	Phase 3
0.6733	Remote Similarity	NPD7515	Phase 2
0.67	Remote Similarity	NPD6051	Approved
0.6699	Remote Similarity	NPD5654	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6635	Remote Similarity	NPD5221	Approved
0.6635	Remote Similarity	NPD5222	Approved
0.6635	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4697	Phase 3
0.6634	Remote Similarity	NPD5207	Approved
0.6634	Remote Similarity	NPD6698	Approved
0.6634	Remote Similarity	NPD46	Approved
0.6633	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6008	Approved
0.66	Remote Similarity	NPD5208	Approved
0.6585	Remote Similarity	NPD7260	Phase 2
0.6571	Remote Similarity	NPD5959	Approved
0.6571	Remote Similarity	NPD5173	Approved
0.6569	Remote Similarity	NPD6079	Approved
0.6566	Remote Similarity	NPD3618	Phase 1
0.6566	Remote Similarity	NPD5786	Approved
0.6552	Remote Similarity	NPD6335	Approved
0.6552	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4753	Phase 2
0.6535	Remote Similarity	NPD5328	Approved
0.6531	Remote Similarity	NPD3665	Phase 1
0.6531	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3133	Approved
0.6531	Remote Similarity	NPD3666	Approved
0.6522	Remote Similarity	NPD6274	Approved
0.6518	Remote Similarity	NPD6371	Approved
0.6496	Remote Similarity	NPD7101	Approved
0.6496	Remote Similarity	NPD7100	Approved
0.6495	Remote Similarity	NPD4269	Approved
0.6495	Remote Similarity	NPD4270	Approved
0.6495	Remote Similarity	NPD6435	Approved
0.6489	Remote Similarity	NPD4756	Discovery
0.6481	Remote Similarity	NPD5211	Phase 2
0.6476	Remote Similarity	NPD7614	Phase 1
0.6466	Remote Similarity	NPD6317	Approved
0.6465	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5329	Approved
0.6449	Remote Similarity	NPD5286	Approved
0.6449	Remote Similarity	NPD4696	Approved
0.6449	Remote Similarity	NPD5285	Approved
0.6442	Remote Similarity	NPD5282	Discontinued
0.6442	Remote Similarity	NPD6001	Approved
0.6429	Remote Similarity	NPD5362	Discontinued
0.6429	Remote Similarity	NPD7154	Phase 3
0.6415	Remote Similarity	NPD4755	Approved
0.641	Remote Similarity	NPD6313	Approved
0.641	Remote Similarity	NPD6314	Approved
0.6408	Remote Similarity	NPD5284	Approved
0.6408	Remote Similarity	NPD6411	Approved
0.6408	Remote Similarity	NPD5281	Approved
0.64	Remote Similarity	NPD5690	Phase 2
0.6392	Remote Similarity	NPD5369	Approved
0.6389	Remote Similarity	NPD5223	Approved
0.6374	Remote Similarity	NPD4691	Approved
0.6373	Remote Similarity	NPD1695	Approved
0.6372	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD2067	Discontinued
0.6364	Remote Similarity	NPD5141	Approved
0.6364	Remote Similarity	NPD3668	Phase 3
0.6364	Remote Similarity	NPD4197	Approved
0.6364	Remote Similarity	NPD4786	Approved
0.6348	Remote Similarity	NPD4632	Approved
0.6346	Remote Similarity	NPD5779	Approved
0.6346	Remote Similarity	NPD5778	Approved
0.633	Remote Similarity	NPD7632	Discontinued
0.633	Remote Similarity	NPD5226	Approved
0.633	Remote Similarity	NPD5224	Approved
0.633	Remote Similarity	NPD4633	Approved
0.633	Remote Similarity	NPD5225	Approved
0.6327	Remote Similarity	NPD3667	Approved
0.6325	Remote Similarity	NPD6009	Approved
0.6303	Remote Similarity	NPD6319	Approved
0.63	Remote Similarity	NPD1696	Phase 3
0.6296	Remote Similarity	NPD4700	Approved
0.6292	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5368	Approved
0.6289	Remote Similarity	NPD4252	Approved
0.6283	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7604	Phase 2
0.6273	Remote Similarity	NPD6052	Approved
0.6273	Remote Similarity	NPD5175	Approved
0.6273	Remote Similarity	NPD5174	Approved
0.627	Remote Similarity	NPD6845	Suspended
0.6264	Remote Similarity	NPD4137	Phase 3
0.6263	Remote Similarity	NPD6110	Phase 1
0.6261	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD8034	Phase 2
0.625	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD3617	Approved
0.625	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4694	Approved
0.6238	Remote Similarity	NPD4623	Approved
0.6238	Remote Similarity	NPD5280	Approved
0.6238	Remote Similarity	NPD4519	Discontinued
0.6238	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7492	Approved
0.6214	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6101	Approved
0.6196	Remote Similarity	NPD4747	Approved
0.6195	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5091	Approved
0.6179	Remote Similarity	NPD7507	Approved
0.6179	Remote Similarity	NPD6336	Discontinued
0.6179	Remote Similarity	NPD6616	Approved
0.617	Remote Similarity	NPD5733	Approved
0.617	Remote Similarity	NPD4058	Approved
0.6167	Remote Similarity	NPD6054	Approved
0.6162	Remote Similarity	NPD4221	Approved
0.6162	Remote Similarity	NPD4223	Phase 3
0.6148	Remote Similarity	NPD8328	Phase 3
0.6129	Remote Similarity	NPD7078	Approved
0.6129	Remote Similarity	NPD5276	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