NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	272.862
LogP:	0.973
LogD:	1.222
LogS:	-2.816
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	4.796
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.717
MDCK Permeability:	1.861289820226375e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.761
20% Bioavailability (F20%):	0.849
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	81.8891830444336%
Volume Distribution (VD):	0.779
Pgp-substrate:	13.025312423706055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.303
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.178
CYP2C19-substrate:	0.373
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.207
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	5.556
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.28
Rat Oral Acute Toxicity:	0.751
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.442
Carcinogencity:	0.144
Eye Corrosion:	0.053
Eye Irritation:	0.042
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC59097

Natural Product ID:	NPC59097
*Common Name:**	Allo-Schkuhriolide
IUPAC Name:	(3aR,4R,6E,10E,11aR)-4-hydroxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carbaldehyde
Synonyms:	Allo-Schkuhriolide
Standard InCHIKey:	DABORJCHZSJBJP-JMCBBATMSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-9-4-3-5-11(8-16)7-12(17)14-10(2)15(18)19-13(14)6-9/h5-6,8,12-14,17H,2-4,7H2,1H3/b9-6+,11-5+/t12-,13-,14-/m1/s1
SMILES:	O=C/C/1=C/CC/C(=C/[C@@H]2[C@@H]([C@@H](C1)O)C(=C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472440
PubChem CID:	10015562
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO2847	Schkuhria schkuhrioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748370]
NPO2847	Schkuhria schkuhrioides	Species	Asteraceae	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
ED50	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.00057	ug ml-1	PMID[458296]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.82	ug ml-1	PMID[458296]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.9	ug ml-1	PMID[458296]

☑ 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 NPC59097 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	170
0.1-0.2	1186
0.2-0.3	5364
0.3-0.4	13812
0.4-0.5	11750
0.5-0.6	6687
0.6-0.7	2854
0.7-0.8	713
0.8-0.85	67
0.85-0.9	50
0.9-0.95	42
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9494	High Similarity	NPC169575
0.9494	High Similarity	NPC40746
0.9487	High Similarity	NPC24417
0.9481	High Similarity	NPC167881
0.9481	High Similarity	NPC98557
0.9383	High Similarity	NPC150755
0.9367	High Similarity	NPC229825
0.9359	High Similarity	NPC281132
0.9259	High Similarity	NPC470755
0.925	High Similarity	NPC131669
0.925	High Similarity	NPC473390
0.9146	High Similarity	NPC305475
0.9146	High Similarity	NPC475461
0.9136	High Similarity	NPC476804
0.9136	High Similarity	NPC96259
0.9136	High Similarity	NPC114979
0.9136	High Similarity	NPC158756
0.9136	High Similarity	NPC141193
0.9136	High Similarity	NPC191476
0.9103	High Similarity	NPC471465
0.9103	High Similarity	NPC196653
0.9024	High Similarity	NPC255307
0.9	High Similarity	NPC52861
0.8987	High Similarity	NPC270126
0.8974	High Similarity	NPC171204
0.8974	High Similarity	NPC476028
0.8974	High Similarity	NPC141789
0.8929	High Similarity	NPC475819
0.8929	High Similarity	NPC476805
0.8916	High Similarity	NPC469910
0.8861	High Similarity	NPC108816
0.8861	High Similarity	NPC93763
0.8846	High Similarity	NPC68819
0.878	High Similarity	NPC116543
0.875	High Similarity	NPC477922
0.8734	High Similarity	NPC116177
0.8734	High Similarity	NPC320630
0.8734	High Similarity	NPC7563
0.8721	High Similarity	NPC475855
0.8721	High Similarity	NPC473619
0.8706	High Similarity	NPC473715
0.8706	High Similarity	NPC476803
0.8701	High Similarity	NPC269206
0.8701	High Similarity	NPC295633
0.8701	High Similarity	NPC58956
0.8652	High Similarity	NPC477921
0.8621	High Similarity	NPC473321
0.859	High Similarity	NPC476355
0.8571	High Similarity	NPC165162
0.8523	High Similarity	NPC475838
0.8523	High Similarity	NPC288240
0.8523	High Similarity	NPC162205
0.8523	High Similarity	NPC228451
0.8523	High Similarity	NPC295204
0.8523	High Similarity	NPC273579
0.8523	High Similarity	NPC125674
0.8506	High Similarity	NPC469368
0.8506	High Similarity	NPC144133
0.8506	High Similarity	NPC179394
0.8506	High Similarity	NPC474232
0.85	High Similarity	NPC97516
0.8434	Intermediate Similarity	NPC89555
0.8427	Intermediate Similarity	NPC474247
0.8395	Intermediate Similarity	NPC267231
0.8375	Intermediate Similarity	NPC235906
0.8375	Intermediate Similarity	NPC123360
0.8354	Intermediate Similarity	NPC140287
0.8354	Intermediate Similarity	NPC114727
0.8354	Intermediate Similarity	NPC476590
0.8333	Intermediate Similarity	NPC163003
0.8333	Intermediate Similarity	NPC471142
0.8315	Intermediate Similarity	NPC475302
0.8295	Intermediate Similarity	NPC129419
0.8293	Intermediate Similarity	NPC470239
0.8293	Intermediate Similarity	NPC89128
0.8293	Intermediate Similarity	NPC470244
0.825	Intermediate Similarity	NPC155587
0.8242	Intermediate Similarity	NPC279621
0.8242	Intermediate Similarity	NPC230800
0.8222	Intermediate Similarity	NPC303942
0.8222	Intermediate Similarity	NPC57405
0.8182	Intermediate Similarity	NPC474032
0.8182	Intermediate Similarity	NPC268298
0.814	Intermediate Similarity	NPC21469
0.8132	Intermediate Similarity	NPC471141
0.8125	Intermediate Similarity	NPC48641
0.8101	Intermediate Similarity	NPC129665
0.8095	Intermediate Similarity	NPC301477
0.8095	Intermediate Similarity	NPC25684
0.8095	Intermediate Similarity	NPC141810
0.8095	Intermediate Similarity	NPC281949
0.8072	Intermediate Similarity	NPC178277
0.8068	Intermediate Similarity	NPC477302
0.8068	Intermediate Similarity	NPC136879
0.8065	Intermediate Similarity	NPC473326
0.8065	Intermediate Similarity	NPC471144
0.8049	Intermediate Similarity	NPC474760
0.8049	Intermediate Similarity	NPC187568
0.8049	Intermediate Similarity	NPC41780
0.8046	Intermediate Similarity	NPC469483
0.8046	Intermediate Similarity	NPC50637
0.8043	Intermediate Similarity	NPC473859
0.8043	Intermediate Similarity	NPC306041
0.7979	Intermediate Similarity	NPC288876
0.7978	Intermediate Similarity	NPC206001
0.7978	Intermediate Similarity	NPC166919
0.7978	Intermediate Similarity	NPC295312
0.7978	Intermediate Similarity	NPC218927
0.7975	Intermediate Similarity	NPC67183
0.7955	Intermediate Similarity	NPC266957
0.7955	Intermediate Similarity	NPC160138
0.7952	Intermediate Similarity	NPC472960
0.7935	Intermediate Similarity	NPC475659
0.7935	Intermediate Similarity	NPC304886
0.7931	Intermediate Similarity	NPC261380
0.7912	Intermediate Similarity	NPC469692
0.7912	Intermediate Similarity	NPC469645
0.7912	Intermediate Similarity	NPC475912
0.7907	Intermediate Similarity	NPC1761
0.7907	Intermediate Similarity	NPC250315
0.7907	Intermediate Similarity	NPC474703
0.7907	Intermediate Similarity	NPC52609
0.7882	Intermediate Similarity	NPC470241
0.7882	Intermediate Similarity	NPC325031
0.7882	Intermediate Similarity	NPC471325
0.7865	Intermediate Similarity	NPC202672
0.7857	Intermediate Similarity	NPC475210
0.7857	Intermediate Similarity	NPC617
0.7857	Intermediate Similarity	NPC19841
0.7848	Intermediate Similarity	NPC476591
0.7848	Intermediate Similarity	NPC88877
0.7841	Intermediate Similarity	NPC261721
0.7841	Intermediate Similarity	NPC107787
0.7831	Intermediate Similarity	NPC57744
0.7831	Intermediate Similarity	NPC476794
0.7831	Intermediate Similarity	NPC470240
0.7831	Intermediate Similarity	NPC65603
0.7826	Intermediate Similarity	NPC121825
0.7826	Intermediate Similarity	NPC477131
0.7826	Intermediate Similarity	NPC474338
0.7821	Intermediate Similarity	NPC194871
0.7816	Intermediate Similarity	NPC82297
0.7816	Intermediate Similarity	NPC165287
0.7816	Intermediate Similarity	NPC115786
0.7805	Intermediate Similarity	NPC226669
0.7805	Intermediate Similarity	NPC329852
0.7805	Intermediate Similarity	NPC138408
0.7805	Intermediate Similarity	NPC193351
0.7802	Intermediate Similarity	NPC300312
0.7802	Intermediate Similarity	NPC131209
0.7802	Intermediate Similarity	NPC261607
0.7802	Intermediate Similarity	NPC111114
0.7802	Intermediate Similarity	NPC184463
0.7802	Intermediate Similarity	NPC30515
0.7791	Intermediate Similarity	NPC474252
0.7791	Intermediate Similarity	NPC173609
0.7791	Intermediate Similarity	NPC85772
0.7789	Intermediate Similarity	NPC475949
0.7753	Intermediate Similarity	NPC237540
0.7753	Intermediate Similarity	NPC178215
0.7742	Intermediate Similarity	NPC90121
0.7742	Intermediate Similarity	NPC270013
0.7742	Intermediate Similarity	NPC14961
0.7742	Intermediate Similarity	NPC36954
0.7742	Intermediate Similarity	NPC275960
0.7742	Intermediate Similarity	NPC52044
0.7742	Intermediate Similarity	NPC48803
0.7742	Intermediate Similarity	NPC193645
0.7738	Intermediate Similarity	NPC128276
0.7727	Intermediate Similarity	NPC473669
0.7727	Intermediate Similarity	NPC473651
0.7727	Intermediate Similarity	NPC103284
0.7727	Intermediate Similarity	NPC1083
0.7727	Intermediate Similarity	NPC78089
0.7727	Intermediate Similarity	NPC283085
0.7727	Intermediate Similarity	NPC66346
0.7727	Intermediate Similarity	NPC286338
0.7727	Intermediate Similarity	NPC473478
0.7727	Intermediate Similarity	NPC231009
0.7727	Intermediate Similarity	NPC107986
0.7727	Intermediate Similarity	NPC215364
0.7727	Intermediate Similarity	NPC132496
0.7727	Intermediate Similarity	NPC110710
0.7727	Intermediate Similarity	NPC223871
0.7727	Intermediate Similarity	NPC82795
0.7722	Intermediate Similarity	NPC470256
0.7717	Intermediate Similarity	NPC81419
0.7717	Intermediate Similarity	NPC212486
0.7717	Intermediate Similarity	NPC476300
0.7717	Intermediate Similarity	NPC179746
0.7717	Intermediate Similarity	NPC165383
0.7708	Intermediate Similarity	NPC474339
0.7708	Intermediate Similarity	NPC164598
0.7701	Intermediate Similarity	NPC475947
0.7692	Intermediate Similarity	NPC71533
0.7692	Intermediate Similarity	NPC106510
0.7692	Intermediate Similarity	NPC51004
0.7692	Intermediate Similarity	NPC473448
0.7692	Intermediate Similarity	NPC312042
0.7684	Intermediate Similarity	NPC141191

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 NPC59097 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1766
0.2-0.3	3850
0.3-0.4	2359
0.4-0.5	671
0.5-0.6	285
0.6-0.7	44
0.7-0.8	17
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
0.7742	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.7312	Intermediate Similarity	NPD5785	Approved
0.7303	Intermediate Similarity	NPD7154	Phase 3
0.7159	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5363	Approved
0.7021	Intermediate Similarity	NPD1695	Approved
0.699	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4225	Approved
0.6957	Remote Similarity	NPD1694	Approved
0.6957	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7838	Discovery
0.6932	Remote Similarity	NPD4271	Approved
0.6932	Remote Similarity	NPD4268	Approved
0.6923	Remote Similarity	NPD5362	Discontinued
0.6882	Remote Similarity	NPD4249	Approved
0.6813	Remote Similarity	NPD4269	Approved
0.6813	Remote Similarity	NPD6435	Approved
0.6813	Remote Similarity	NPD4270	Approved
0.6813	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4251	Approved
0.6809	Remote Similarity	NPD4250	Approved
0.6792	Remote Similarity	NPD6371	Approved
0.6778	Remote Similarity	NPD4819	Approved
0.6778	Remote Similarity	NPD4821	Approved
0.6778	Remote Similarity	NPD4820	Approved
0.6778	Remote Similarity	NPD4822	Approved
0.6778	Remote Similarity	NPD4252	Approved
0.6703	Remote Similarity	NPD5369	Approved
0.6702	Remote Similarity	NPD5786	Approved
0.6701	Remote Similarity	NPD7983	Approved
0.6634	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5209	Approved
0.6604	Remote Similarity	NPD6686	Approved
0.6593	Remote Similarity	NPD5368	Approved
0.6556	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5778	Approved
0.6465	Remote Similarity	NPD5779	Approved
0.6444	Remote Similarity	NPD4756	Discovery
0.6422	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5282	Discontinued
0.6383	Remote Similarity	NPD5331	Approved
0.6383	Remote Similarity	NPD5332	Approved
0.6364	Remote Similarity	NPD6053	Discontinued
0.6344	Remote Similarity	NPD4790	Discontinued
0.6327	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5370	Suspended
0.6327	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD7638	Approved
0.63	Remote Similarity	NPD6399	Phase 3
0.6283	Remote Similarity	NPD7115	Discovery
0.6275	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7639	Approved
0.6222	Remote Similarity	NPD8039	Approved
0.62	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD5344	Discontinued
0.6058	Remote Similarity	NPD6083	Phase 2
0.6058	Remote Similarity	NPD6084	Phase 2
0.6058	Remote Similarity	NPD7902	Approved
0.6055	Remote Similarity	NPD5697	Approved
0.604	Remote Similarity	NPD7637	Suspended
0.6024	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.602	Remote Similarity	NPD6422	Discontinued
0.6019	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD3197	Phase 1
0.5982	Remote Similarity	NPD6650	Approved
0.5982	Remote Similarity	NPD6649	Approved
0.5977	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7642	Approved
0.5963	Remote Similarity	NPD7128	Approved
0.5963	Remote Similarity	NPD6675	Approved
0.5963	Remote Similarity	NPD5739	Approved
0.5963	Remote Similarity	NPD6402	Approved
0.5948	Remote Similarity	NPD7641	Discontinued
0.5946	Remote Similarity	NPD6012	Approved
0.5946	Remote Similarity	NPD6373	Approved
0.5946	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6014	Approved
0.5946	Remote Similarity	NPD6013	Approved
0.5946	Remote Similarity	NPD6372	Approved
0.5943	Remote Similarity	NPD6648	Approved
0.5932	Remote Similarity	NPD8513	Phase 3
0.5932	Remote Similarity	NPD8515	Approved
0.5932	Remote Similarity	NPD8516	Approved
0.5932	Remote Similarity	NPD8517	Approved
0.5926	Remote Similarity	NPD6647	Phase 2
0.5922	Remote Similarity	NPD7748	Approved
0.5909	Remote Similarity	NPD5701	Approved
0.5893	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7102	Approved
0.5893	Remote Similarity	NPD7290	Approved
0.5893	Remote Similarity	NPD6883	Approved
0.5882	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7515	Phase 2
0.5876	Remote Similarity	NPD6110	Phase 1
0.5868	Remote Similarity	NPD7507	Approved
0.5862	Remote Similarity	NPD3704	Approved
0.5862	Remote Similarity	NPD7331	Phase 2
0.5859	Remote Similarity	NPD5330	Approved
0.5859	Remote Similarity	NPD7146	Approved
0.5859	Remote Similarity	NPD7521	Approved
0.5859	Remote Similarity	NPD3618	Phase 1
0.5859	Remote Similarity	NPD6409	Approved
0.5859	Remote Similarity	NPD6684	Approved
0.5859	Remote Similarity	NPD7334	Approved
0.5856	Remote Similarity	NPD7320	Approved
0.5856	Remote Similarity	NPD6011	Approved
0.5841	Remote Similarity	NPD6847	Approved
0.5841	Remote Similarity	NPD6617	Approved
0.5841	Remote Similarity	NPD6869	Approved
0.5841	Remote Similarity	NPD8130	Phase 1
0.5816	Remote Similarity	NPD3666	Approved
0.5816	Remote Similarity	NPD3133	Approved
0.5816	Remote Similarity	NPD3665	Phase 1
0.581	Remote Similarity	NPD4697	Phase 3
0.5789	Remote Similarity	NPD6882	Approved
0.5789	Remote Similarity	NPD8297	Approved
0.5773	Remote Similarity	NPD3667	Approved
0.5769	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7900	Approved
0.5765	Remote Similarity	NPD368	Approved
0.5752	Remote Similarity	NPD2067	Discontinued
0.575	Remote Similarity	NPD3172	Approved
0.5743	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6672	Approved
0.5743	Remote Similarity	NPD5737	Approved
0.5743	Remote Similarity	NPD6903	Approved
0.5729	Remote Similarity	NPD4695	Discontinued
0.5728	Remote Similarity	NPD5281	Approved
0.5728	Remote Similarity	NPD5284	Approved
0.5728	Remote Similarity	NPD5693	Phase 1
0.5726	Remote Similarity	NPD7319	Approved
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5702	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD2204	Approved
0.5702	Remote Similarity	NPD7830	Approved
0.5702	Remote Similarity	NPD7829	Approved
0.57	Remote Similarity	NPD5279	Phase 3
0.5696	Remote Similarity	NPD6927	Phase 3
0.5691	Remote Similarity	NPD8074	Phase 3
0.5688	Remote Similarity	NPD5211	Phase 2
0.5688	Remote Similarity	NPD7632	Discontinued
0.5686	Remote Similarity	NPD4753	Phase 2
0.5679	Remote Similarity	NPD3196	Approved
0.5679	Remote Similarity	NPD3195	Phase 2
0.5679	Remote Similarity	NPD4266	Approved
0.5679	Remote Similarity	NPD3194	Approved
0.5676	Remote Similarity	NPD6008	Approved
0.566	Remote Similarity	NPD4228	Discovery
0.566	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4786	Approved
0.5648	Remote Similarity	NPD5285	Approved
0.5648	Remote Similarity	NPD4696	Approved
0.5648	Remote Similarity	NPD5286	Approved
0.5641	Remote Similarity	NPD6274	Approved
0.5625	Remote Similarity	NPD6412	Phase 2
0.5625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6421	Discontinued
0.561	Remote Similarity	NPD342	Phase 1
0.561	Remote Similarity	NPD8451	Approved
0.5607	Remote Similarity	NPD4755	Approved
0.56	Remote Similarity	NPD1696	Phase 3

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