NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	362.14
Volume:	363.144
LogP:	0.901
LogD:	0.906
LogS:	-3.068
# Rotatable Bonds:	5
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	5.145
Fsp3:	0.421
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:	-5.235
MDCK Permeability:	4.578112930175848e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.883
20% Bioavailability (F20%):	0.207
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	72.10012817382812%
Volume Distribution (VD):	0.519
Pgp-substrate:	33.60506057739258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.109
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.122
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	4.073
Half-life (T1/2):	0.776

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.305
Drug-inuced Liver Injury (DILI):	0.378
AMES Toxicity:	0.215
Rat Oral Acute Toxicity:	0.536
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.586
Carcinogencity:	0.24
Eye Corrosion:	0.076
Eye Irritation:	0.294
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC477921

Natural Product ID:	NPC477921
*Common Name:**	[(3aS,4S,5R,6E,10E,11aR)-6-formyl-5-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
IUPAC Name:	[(3aS,4S,5R,6E,10E,11aR)-6-formyl-5-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
Synonyms:
Standard InCHIKey:	HQPSNGXRJBMMAL-ILVUNATCSA-N
Standard InCHI:	InChI=1S/C19H22O7/c1-10(2)18(23)26-17-15-11(3)19(24)25-14(15)7-12(8-20)5-4-6-13(9-21)16(17)22/h6-7,9,14-17,20,22H,1,3-5,8H2,2H3/b12-7+,13-6-/t14-,15+,16-,17+/m1/s1
SMILES:	CC(=C)C(=O)O[C@H]1[C@@H]2[C@@H](/C=C(\CC/C=C(\[C@H]1O)/C=O)/CO)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118708059
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
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19928884]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial part	n.a.	n.a.	PMID[24997688]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2
Others	2

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	9.01	%	PMID[24997688]
NPT2	Others	Unspecified	IC50	>	10	ug/ml	PMID[24997688]
NPT2	Others	Unspecified	Inhibition	=	20.76	%	PMID[24997688]

☑ 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 NPC477921 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	210
0.1-0.2	1399
0.2-0.3	5023
0.3-0.4	8879
0.4-0.5	15108
0.5-0.6	7441
0.6-0.7	3505
0.7-0.8	924
0.8-0.85	140
0.85-0.9	53
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC477922
0.9551	High Similarity	NPC473321
0.9451	High Similarity	NPC471142
0.9438	High Similarity	NPC473619
0.9231	High Similarity	NPC162205
0.9231	High Similarity	NPC295204
0.9231	High Similarity	NPC288240
0.9231	High Similarity	NPC273579
0.9213	High Similarity	NPC473715
0.9149	High Similarity	NPC471144
0.9053	High Similarity	NPC288876
0.9011	High Similarity	NPC474232
0.8989	High Similarity	NPC469910
0.8936	High Similarity	NPC473859
0.8901	High Similarity	NPC474032
0.8876	High Similarity	NPC470755
0.8876	High Similarity	NPC21469
0.8854	High Similarity	NPC475949
0.883	High Similarity	NPC475659
0.8817	High Similarity	NPC475912
0.8791	High Similarity	NPC475819
0.8791	High Similarity	NPC476803
0.8764	High Similarity	NPC158756
0.8723	High Similarity	NPC57405
0.8723	High Similarity	NPC303942
0.8673	High Similarity	NPC149371
0.8652	High Similarity	NPC59097
0.8652	High Similarity	NPC169575
0.8652	High Similarity	NPC40746
0.8632	High Similarity	NPC14961
0.8632	High Similarity	NPC36954
0.8632	High Similarity	NPC270013
0.8602	High Similarity	NPC475855
0.8587	High Similarity	NPC476805
0.8571	High Similarity	NPC47880
0.8557	High Similarity	NPC473326
0.8542	High Similarity	NPC279621
0.8542	High Similarity	NPC230800
0.8526	High Similarity	NPC81386
0.8526	High Similarity	NPC474035
0.8515	High Similarity	NPC477513
0.8511	High Similarity	NPC30515
0.8511	High Similarity	NPC184463
0.85	High Similarity	NPC100487
0.8444	Intermediate Similarity	NPC131669
0.8444	Intermediate Similarity	NPC473390
0.8444	Intermediate Similarity	NPC116543
0.8427	Intermediate Similarity	NPC24417
0.8421	Intermediate Similarity	NPC179746
0.8421	Intermediate Similarity	NPC81419
0.8421	Intermediate Similarity	NPC125674
0.8421	Intermediate Similarity	NPC476300
0.8421	Intermediate Similarity	NPC212486
0.8421	Intermediate Similarity	NPC228451
0.8421	Intermediate Similarity	NPC475838
0.8404	Intermediate Similarity	NPC474761
0.8404	Intermediate Similarity	NPC51004
0.8404	Intermediate Similarity	NPC144133
0.8404	Intermediate Similarity	NPC179394
0.8404	Intermediate Similarity	NPC476004
0.84	Intermediate Similarity	NPC475871
0.84	Intermediate Similarity	NPC475945
0.8387	Intermediate Similarity	NPC202672
0.8384	Intermediate Similarity	NPC474339
0.8384	Intermediate Similarity	NPC164598
0.837	Intermediate Similarity	NPC305475
0.837	Intermediate Similarity	NPC150755
0.837	Intermediate Similarity	NPC475461
0.8367	Intermediate Similarity	NPC474213
0.8352	Intermediate Similarity	NPC476804
0.8351	Intermediate Similarity	NPC17585
0.8351	Intermediate Similarity	NPC476315
0.8351	Intermediate Similarity	NPC306041
0.8333	Intermediate Similarity	NPC471147
0.8333	Intermediate Similarity	NPC229825
0.8333	Intermediate Similarity	NPC474247
0.8317	Intermediate Similarity	NPC203659
0.8316	Intermediate Similarity	NPC208886
0.8316	Intermediate Similarity	NPC12172
0.8315	Intermediate Similarity	NPC281132
0.83	Intermediate Similarity	NPC471148
0.83	Intermediate Similarity	NPC474747
0.8298	Intermediate Similarity	NPC295312
0.8298	Intermediate Similarity	NPC307411
0.8265	Intermediate Similarity	NPC40812
0.8261	Intermediate Similarity	NPC255307
0.8247	Intermediate Similarity	NPC471141
0.8229	Intermediate Similarity	NPC469645
0.8229	Intermediate Similarity	NPC469692
0.8218	Intermediate Similarity	NPC472755
0.8218	Intermediate Similarity	NPC110989
0.8211	Intermediate Similarity	NPC71533
0.8211	Intermediate Similarity	NPC106510
0.8202	Intermediate Similarity	NPC98557
0.8202	Intermediate Similarity	NPC167881
0.82	Intermediate Similarity	NPC110443
0.82	Intermediate Similarity	NPC133907
0.82	Intermediate Similarity	NPC46998
0.82	Intermediate Similarity	NPC128733
0.82	Intermediate Similarity	NPC474742
0.82	Intermediate Similarity	NPC201718
0.82	Intermediate Similarity	NPC185141
0.8182	Intermediate Similarity	NPC187761
0.8182	Intermediate Similarity	NPC83895
0.8182	Intermediate Similarity	NPC187268
0.8172	Intermediate Similarity	NPC112685
0.8152	Intermediate Similarity	NPC141193
0.8152	Intermediate Similarity	NPC191476
0.8152	Intermediate Similarity	NPC114979
0.8152	Intermediate Similarity	NPC96259
0.8144	Intermediate Similarity	NPC140543
0.8144	Intermediate Similarity	NPC473316
0.8144	Intermediate Similarity	NPC473330
0.8144	Intermediate Similarity	NPC121825
0.8137	Intermediate Similarity	NPC474741
0.8119	Intermediate Similarity	NPC225353
0.8105	Intermediate Similarity	NPC151770
0.8105	Intermediate Similarity	NPC477011
0.8105	Intermediate Similarity	NPC166919
0.81	Intermediate Similarity	NPC477512
0.809	Intermediate Similarity	NPC108816
0.809	Intermediate Similarity	NPC196653
0.809	Intermediate Similarity	NPC93763
0.809	Intermediate Similarity	NPC471465
0.8058	Intermediate Similarity	NPC243998
0.8041	Intermediate Similarity	NPC475302
0.8022	Intermediate Similarity	NPC52861
0.8021	Intermediate Similarity	NPC473455
0.802	Intermediate Similarity	NPC472753
0.802	Intermediate Similarity	NPC476270
0.802	Intermediate Similarity	NPC264477
0.802	Intermediate Similarity	NPC477511
0.8	Intermediate Similarity	NPC153805
0.8	Intermediate Similarity	NPC20339
0.8	Intermediate Similarity	NPC208233
0.8	Intermediate Similarity	NPC89001
0.8	Intermediate Similarity	NPC233551
0.8	Intermediate Similarity	NPC261377
0.8	Intermediate Similarity	NPC280621
0.8	Intermediate Similarity	NPC270126
0.8	Intermediate Similarity	NPC48338
0.8	Intermediate Similarity	NPC38154
0.8	Intermediate Similarity	NPC255592
0.8	Intermediate Similarity	NPC308567
0.8	Intermediate Similarity	NPC40376
0.8	Intermediate Similarity	NPC21208
0.798	Intermediate Similarity	NPC39859
0.798	Intermediate Similarity	NPC35498
0.798	Intermediate Similarity	NPC76862
0.798	Intermediate Similarity	NPC158416
0.798	Intermediate Similarity	NPC470883
0.7979	Intermediate Similarity	NPC62118
0.7979	Intermediate Similarity	NPC107717
0.7979	Intermediate Similarity	NPC469483
0.7979	Intermediate Similarity	NPC171174
0.7979	Intermediate Similarity	NPC232555
0.7979	Intermediate Similarity	NPC240695
0.7979	Intermediate Similarity	NPC114694
0.7979	Intermediate Similarity	NPC475581
0.7979	Intermediate Similarity	NPC231096
0.7979	Intermediate Similarity	NPC142117
0.7978	Intermediate Similarity	NPC141789
0.7978	Intermediate Similarity	NPC171204
0.7978	Intermediate Similarity	NPC320630
0.7978	Intermediate Similarity	NPC116177
0.7978	Intermediate Similarity	NPC476028
0.7978	Intermediate Similarity	NPC7563
0.7961	Intermediate Similarity	NPC220964
0.7961	Intermediate Similarity	NPC475676
0.7959	Intermediate Similarity	NPC476267
0.7941	Intermediate Similarity	NPC324017
0.7941	Intermediate Similarity	NPC320019
0.7941	Intermediate Similarity	NPC86077
0.7941	Intermediate Similarity	NPC472754
0.7917	Intermediate Similarity	NPC477016
0.7917	Intermediate Similarity	NPC130359
0.7917	Intermediate Similarity	NPC14901
0.7917	Intermediate Similarity	NPC477017
0.7917	Intermediate Similarity	NPC280612
0.7917	Intermediate Similarity	NPC87306
0.79	Intermediate Similarity	NPC471462
0.7895	Intermediate Similarity	NPC266957
0.7895	Intermediate Similarity	NPC231889
0.7895	Intermediate Similarity	NPC178215
0.7895	Intermediate Similarity	NPC186148
0.7895	Intermediate Similarity	NPC160138
0.7885	Intermediate Similarity	NPC223450
0.7879	Intermediate Similarity	NPC304886
0.7872	Intermediate Similarity	NPC50362
0.7872	Intermediate Similarity	NPC231009
0.7872	Intermediate Similarity	NPC1083
0.7872	Intermediate Similarity	NPC471567
0.7872	Intermediate Similarity	NPC82795
0.7872	Intermediate Similarity	NPC319795
0.7872	Intermediate Similarity	NPC473478
0.7872	Intermediate Similarity	NPC107986
0.7872	Intermediate Similarity	NPC103284
0.7872	Intermediate Similarity	NPC477018
0.7872	Intermediate Similarity	NPC283085
0.7872	Intermediate Similarity	NPC223871

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 NPC477921 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	2031
0.2-0.3	3732
0.3-0.4	2103
0.4-0.5	755
0.5-0.6	254
0.6-0.7	66
0.7-0.8	11
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
0.7938	Intermediate Similarity	NPD7983	Approved
0.7872	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD46	Approved
0.7835	Intermediate Similarity	NPD6698	Approved
0.7642	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6371	Approved
0.7525	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4225	Approved
0.73	Intermediate Similarity	NPD7838	Discovery
0.7129	Intermediate Similarity	NPD5785	Approved
0.699	Remote Similarity	NPD5778	Approved
0.699	Remote Similarity	NPD5779	Approved
0.6981	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5363	Approved
0.6949	Remote Similarity	NPD8513	Phase 3
0.6949	Remote Similarity	NPD8515	Approved
0.6949	Remote Similarity	NPD8517	Approved
0.6949	Remote Similarity	NPD8516	Approved
0.6937	Remote Similarity	NPD6686	Approved
0.6903	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4249	Approved
0.69	Remote Similarity	NPD5786	Approved
0.6833	Remote Similarity	NPD7642	Approved
0.6832	Remote Similarity	NPD4251	Approved
0.6832	Remote Similarity	NPD4250	Approved
0.6792	Remote Similarity	NPD7839	Suspended
0.6768	Remote Similarity	NPD7154	Phase 3
0.6699	Remote Similarity	NPD1695	Approved
0.6697	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4252	Approved
0.661	Remote Similarity	NPD7115	Discovery
0.6604	Remote Similarity	NPD5282	Discontinued
0.66	Remote Similarity	NPD6110	Phase 1
0.656	Remote Similarity	NPD7319	Approved
0.6557	Remote Similarity	NPD7830	Approved
0.6557	Remote Similarity	NPD7829	Approved
0.6555	Remote Similarity	NPD7641	Discontinued
0.6552	Remote Similarity	NPD6053	Discontinued
0.65	Remote Similarity	NPD6435	Approved
0.6452	Remote Similarity	NPD8451	Approved
0.6452	Remote Similarity	NPD7507	Approved
0.6436	Remote Similarity	NPD5362	Discontinued
0.6429	Remote Similarity	NPD4268	Approved
0.6429	Remote Similarity	NPD4271	Approved
0.64	Remote Similarity	NPD8448	Approved
0.64	Remote Similarity	NPD5369	Approved
0.6381	Remote Similarity	NPD6101	Approved
0.6381	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8340	Approved
0.6371	Remote Similarity	NPD8299	Approved
0.6371	Remote Similarity	NPD8342	Approved
0.6371	Remote Similarity	NPD8341	Approved
0.6337	Remote Similarity	NPD5209	Approved
0.6336	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD2204	Approved
0.6311	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6319	Approved
0.6306	Remote Similarity	NPD7639	Approved
0.6306	Remote Similarity	NPD6648	Approved
0.6306	Remote Similarity	NPD7640	Approved
0.63	Remote Similarity	NPD4819	Approved
0.63	Remote Similarity	NPD4822	Approved
0.63	Remote Similarity	NPD5368	Approved
0.63	Remote Similarity	NPD4820	Approved
0.63	Remote Similarity	NPD4821	Approved
0.6293	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6411	Approved
0.6262	Remote Similarity	NPD7637	Suspended
0.626	Remote Similarity	NPD8444	Approved
0.625	Remote Similarity	NPD8390	Approved
0.625	Remote Similarity	NPD8392	Approved
0.625	Remote Similarity	NPD8391	Approved
0.6237	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5370	Suspended
0.6216	Remote Similarity	NPD7638	Approved
0.6207	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1694	Approved
0.6111	Remote Similarity	NPD7492	Approved
0.6111	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6421	Discontinued
0.6102	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD4632	Approved
0.6066	Remote Similarity	NPD7500	Approved
0.6063	Remote Similarity	NPD6616	Approved
0.6063	Remote Similarity	NPD8273	Phase 1
0.6058	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6054	Approved
0.6032	Remote Similarity	NPD8328	Phase 3
0.6016	Remote Similarity	NPD7078	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD4756	Discovery
0.5983	Remote Similarity	NPD6412	Phase 2
0.5969	Remote Similarity	NPD7736	Approved
0.5962	Remote Similarity	NPD5331	Approved
0.5962	Remote Similarity	NPD5332	Approved
0.5954	Remote Similarity	NPD7260	Phase 2
0.5952	Remote Similarity	NPD6370	Approved
0.5952	Remote Similarity	NPD5988	Approved
0.5922	Remote Similarity	NPD4790	Discontinued
0.592	Remote Similarity	NPD6059	Approved
0.5897	Remote Similarity	NPD6008	Approved
0.5891	Remote Similarity	NPD8293	Discontinued
0.5868	Remote Similarity	NPD8297	Approved
0.5865	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD5697	Approved
0.5847	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4634	Approved
0.5827	Remote Similarity	NPD8080	Discontinued
0.5806	Remote Similarity	NPD6009	Approved
0.5806	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6899	Approved
0.5798	Remote Similarity	NPD6881	Approved
0.5794	Remote Similarity	NPD6422	Discontinued
0.5789	Remote Similarity	NPD6845	Suspended
0.5785	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6649	Approved
0.5785	Remote Similarity	NPD6650	Approved
0.5778	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD7632	Discontinued
0.5766	Remote Similarity	NPD6399	Phase 3
0.5763	Remote Similarity	NPD5739	Approved
0.5763	Remote Similarity	NPD7128	Approved
0.5763	Remote Similarity	NPD6402	Approved
0.5763	Remote Similarity	NPD5048	Discontinued
0.5763	Remote Similarity	NPD6675	Approved
0.5752	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6014	Approved
0.575	Remote Similarity	NPD6372	Approved
0.575	Remote Similarity	NPD6373	Approved
0.575	Remote Similarity	NPD6013	Approved
0.575	Remote Similarity	NPD6012	Approved
0.5748	Remote Similarity	NPD8268	Approved
0.5748	Remote Similarity	NPD8266	Approved
0.5748	Remote Similarity	NPD8269	Approved
0.5748	Remote Similarity	NPD8267	Approved
0.5748	Remote Similarity	NPD5983	Phase 2
0.5745	Remote Similarity	NPD3197	Phase 1
0.5714	Remote Similarity	NPD5701	Approved
0.5702	Remote Similarity	NPD6883	Approved
0.5702	Remote Similarity	NPD7290	Approved
0.5702	Remote Similarity	NPD7102	Approved
0.5667	Remote Similarity	NPD7320	Approved
0.5667	Remote Similarity	NPD6011	Approved
0.5659	Remote Similarity	NPD7604	Phase 2
0.5656	Remote Similarity	NPD6869	Approved
0.5656	Remote Similarity	NPD8130	Phase 1
0.5656	Remote Similarity	NPD6847	Approved
0.5656	Remote Similarity	NPD6617	Approved
0.5644	Remote Similarity	NPD8039	Approved
0.5641	Remote Similarity	NPD5211	Phase 2
0.5635	Remote Similarity	NPD7327	Approved
0.5635	Remote Similarity	NPD7328	Approved
0.5625	Remote Similarity	NPD8033	Approved
0.5625	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7503	Approved
0.5625	Remote Similarity	NPD7331	Phase 2
0.5625	Remote Similarity	NPD6921	Approved
0.5614	Remote Similarity	NPD4697	Phase 3
0.561	Remote Similarity	NPD6882	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