NPASS Compound

Structure

NPC471795 OpenBabel07101718312D 22 24 0 0 1 0 0 0 0 0999 V2000 5.5049 -3.1199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6775 1.3216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5359 1.8345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9920 -2.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5050 -3.1349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2379 0.2014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5469 0.9242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1336 -2.7893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2602 -2.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9771 -1.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6656 -0.3951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1037 -0.7895 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5509 0.8346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9921 -2.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2453 -1.3024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0900 0.4226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 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 1 5 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 6 0 0 0 14 19 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 14 1 6 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 18 4 1 1 0 0 0 19 12 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.2
Volume:	329.972
LogP:	4.106
LogD:	3.586
LogS:	-4.46
# Rotatable Bonds:	2
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.802
Synthetic Accessibility Score:	4.746
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.849
MDCK Permeability:	1.7517691958346404e-05
Pgp-inhibitor:	0.103
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	96.33281707763672%
Volume Distribution (VD):	1.159
Pgp-substrate:	5.412916660308838%

ADMET: Metabolism

CYP1A2-inhibitor:	0.093
CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.156
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.257
CYP2C9-substrate:	0.808
CYP2D6-inhibitor:	0.189
CYP2D6-substrate:	0.542
CYP3A4-inhibitor:	0.661
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	7.218
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.097
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.359
Skin Sensitization:	0.118
Carcinogencity:	0.72
Eye Corrosion:	0.014
Eye Irritation:	0.436
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC471795

Natural Product ID:	NPC471795
*Common Name:**	Ebractenoid A
IUPAC Name:	(3aR,6aR,8R,10aS)-8-ethenyl-10a-(hydroxymethyl)-4,4,8-trimethyl-5,6,6a,7,9,10-hexahydro-3aH-benzo[6,7]cyclohepta[4,6-c]furan-2-one
Synonyms:
Standard InCHIKey:	NIKHROFAFUSZHD-HQJJXPTPSA-N
Standard InCHI:	InChI=1S/C19H28O3/c1-5-18(4)8-9-19(12-20)13(11-18)6-7-17(2,3)16-14(19)10-15(21)22-16/h5,10,13,16,20H,1,6-9,11-12H2,2-4H3/t13-,16+,18-,19+/m1/s1
SMILES:	C=C[C@]1(C)CC[C@@]2([C@@H](C1)CCC([C@@H]1C2=CC(=O)O1)(C)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234212
PubChem CID:	90670335
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	7500.0	nM	PMID[521238]

☑ 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 NPC471795 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	171
0.1-0.2	1119
0.2-0.3	4524
0.3-0.4	13756
0.4-0.5	9971
0.5-0.6	7511
0.6-0.7	4884
0.7-0.8	728
0.8-0.85	30
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC471796
0.8795	High Similarity	NPC311070
0.8605	High Similarity	NPC312561
0.8571	High Similarity	NPC472377
0.8571	High Similarity	NPC23748
0.8571	High Similarity	NPC42476
0.8523	High Similarity	NPC182136
0.8523	High Similarity	NPC310479
0.8523	High Similarity	NPC78973
0.8488	Intermediate Similarity	NPC471219
0.8488	Intermediate Similarity	NPC131813
0.8415	Intermediate Similarity	NPC184737
0.8409	Intermediate Similarity	NPC470734
0.8372	Intermediate Similarity	NPC42586
0.8372	Intermediate Similarity	NPC473251
0.8353	Intermediate Similarity	NPC49208
0.8353	Intermediate Similarity	NPC474809
0.8352	Intermediate Similarity	NPC276110
0.8333	Intermediate Similarity	NPC152778
0.8333	Intermediate Similarity	NPC162615
0.8333	Intermediate Similarity	NPC53555
0.8333	Intermediate Similarity	NPC205034
0.8315	Intermediate Similarity	NPC281942
0.8315	Intermediate Similarity	NPC232426
0.8315	Intermediate Similarity	NPC280149
0.8315	Intermediate Similarity	NPC221111
0.8313	Intermediate Similarity	NPC242767
0.8295	Intermediate Similarity	NPC472378
0.8295	Intermediate Similarity	NPC472810
0.8295	Intermediate Similarity	NPC472809
0.8242	Intermediate Similarity	NPC470255
0.8242	Intermediate Similarity	NPC104925
0.8242	Intermediate Similarity	NPC105490
0.8242	Intermediate Similarity	NPC469697
0.8242	Intermediate Similarity	NPC298973
0.8235	Intermediate Similarity	NPC471218
0.8222	Intermediate Similarity	NPC141831
0.8222	Intermediate Similarity	NPC472811
0.8202	Intermediate Similarity	NPC474396
0.8202	Intermediate Similarity	NPC5509
0.8202	Intermediate Similarity	NPC50488
0.8161	Intermediate Similarity	NPC30984
0.8161	Intermediate Similarity	NPC86316
0.8161	Intermediate Similarity	NPC106416
0.814	Intermediate Similarity	NPC193198
0.8132	Intermediate Similarity	NPC7349
0.8132	Intermediate Similarity	NPC472812
0.8132	Intermediate Similarity	NPC115021
0.8118	Intermediate Similarity	NPC475944
0.809	Intermediate Similarity	NPC474629
0.8072	Intermediate Similarity	NPC262747
0.8068	Intermediate Similarity	NPC329692
0.8065	Intermediate Similarity	NPC473153
0.8065	Intermediate Similarity	NPC16967
0.8065	Intermediate Similarity	NPC162346
0.8046	Intermediate Similarity	NPC96055
0.8043	Intermediate Similarity	NPC191521
0.8022	Intermediate Similarity	NPC329842
0.8022	Intermediate Similarity	NPC177037
0.8022	Intermediate Similarity	NPC472814
0.8022	Intermediate Similarity	NPC72845
0.8022	Intermediate Similarity	NPC303697
0.8	Intermediate Similarity	NPC38855
0.8	Intermediate Similarity	NPC473647
0.8	Intermediate Similarity	NPC474592
0.8	Intermediate Similarity	NPC174342
0.8	Intermediate Similarity	NPC233332
0.7979	Intermediate Similarity	NPC208094
0.7978	Intermediate Similarity	NPC473891
0.7976	Intermediate Similarity	NPC209135
0.7976	Intermediate Similarity	NPC474816
0.7957	Intermediate Similarity	NPC295347
0.7957	Intermediate Similarity	NPC472441
0.7957	Intermediate Similarity	NPC209355
0.7955	Intermediate Similarity	NPC474013
0.7955	Intermediate Similarity	NPC65661
0.7935	Intermediate Similarity	NPC139692
0.7931	Intermediate Similarity	NPC12283
0.7931	Intermediate Similarity	NPC477124
0.7931	Intermediate Similarity	NPC474193
0.7912	Intermediate Similarity	NPC51486
0.7907	Intermediate Similarity	NPC159148
0.7895	Intermediate Similarity	NPC278673
0.7895	Intermediate Similarity	NPC474440
0.7895	Intermediate Similarity	NPC316598
0.7889	Intermediate Similarity	NPC93411
0.7882	Intermediate Similarity	NPC100906
0.7872	Intermediate Similarity	NPC165632
0.7857	Intermediate Similarity	NPC189206
0.7857	Intermediate Similarity	NPC283619
0.7849	Intermediate Similarity	NPC53685
0.7849	Intermediate Similarity	NPC201725
0.7849	Intermediate Similarity	NPC57117
0.7849	Intermediate Similarity	NPC469491
0.7841	Intermediate Similarity	NPC470800
0.7841	Intermediate Similarity	NPC82297
0.7841	Intermediate Similarity	NPC471301
0.7841	Intermediate Similarity	NPC46320
0.7841	Intermediate Similarity	NPC474693
0.7841	Intermediate Similarity	NPC471302
0.7835	Intermediate Similarity	NPC476081
0.7826	Intermediate Similarity	NPC477122
0.7826	Intermediate Similarity	NPC233345
0.7826	Intermediate Similarity	NPC234335
0.7826	Intermediate Similarity	NPC186363
0.7816	Intermediate Similarity	NPC256112
0.7816	Intermediate Similarity	NPC471298
0.7812	Intermediate Similarity	NPC474012
0.7812	Intermediate Similarity	NPC324841
0.7812	Intermediate Similarity	NPC227865
0.7812	Intermediate Similarity	NPC476299
0.7802	Intermediate Similarity	NPC82876
0.7802	Intermediate Similarity	NPC177141
0.7802	Intermediate Similarity	NPC261320
0.7802	Intermediate Similarity	NPC168131
0.7791	Intermediate Similarity	NPC281880
0.7791	Intermediate Similarity	NPC268827
0.7789	Intermediate Similarity	NPC231751
0.7789	Intermediate Similarity	NPC98112
0.7789	Intermediate Similarity	NPC51499
0.7789	Intermediate Similarity	NPC53844
0.7789	Intermediate Similarity	NPC477718
0.7789	Intermediate Similarity	NPC202705
0.7789	Intermediate Similarity	NPC477719
0.7778	Intermediate Similarity	NPC476600
0.7778	Intermediate Similarity	NPC166857
0.7778	Intermediate Similarity	NPC45957
0.7778	Intermediate Similarity	NPC471657
0.7766	Intermediate Similarity	NPC183012
0.7765	Intermediate Similarity	NPC172066
0.7755	Intermediate Similarity	NPC297617
0.7753	Intermediate Similarity	NPC475860
0.7753	Intermediate Similarity	NPC474694
0.7753	Intermediate Similarity	NPC472442
0.7753	Intermediate Similarity	NPC35933
0.7753	Intermediate Similarity	NPC473659
0.7753	Intermediate Similarity	NPC329630
0.7753	Intermediate Similarity	NPC189311
0.7753	Intermediate Similarity	NPC109528
0.7742	Intermediate Similarity	NPC166346
0.7742	Intermediate Similarity	NPC156553
0.7738	Intermediate Similarity	NPC476317
0.7732	Intermediate Similarity	NPC472554
0.7732	Intermediate Similarity	NPC11974
0.7727	Intermediate Similarity	NPC471297
0.7727	Intermediate Similarity	NPC321385
0.7727	Intermediate Similarity	NPC476927
0.7727	Intermediate Similarity	NPC79945
0.7727	Intermediate Similarity	NPC472440
0.7727	Intermediate Similarity	NPC57370
0.7723	Intermediate Similarity	NPC228477
0.7723	Intermediate Similarity	NPC137911
0.7717	Intermediate Similarity	NPC209816
0.7717	Intermediate Similarity	NPC273199
0.7717	Intermediate Similarity	NPC477782
0.7717	Intermediate Similarity	NPC220216
0.7708	Intermediate Similarity	NPC473154
0.7708	Intermediate Similarity	NPC325229
0.7708	Intermediate Similarity	NPC222303
0.7708	Intermediate Similarity	NPC275086
0.7708	Intermediate Similarity	NPC98868
0.7701	Intermediate Similarity	NPC325031
0.7701	Intermediate Similarity	NPC112868
0.7701	Intermediate Similarity	NPC170303
0.7701	Intermediate Similarity	NPC142163
0.7692	Intermediate Similarity	NPC477128
0.7692	Intermediate Similarity	NPC226863
0.7684	Intermediate Similarity	NPC242848
0.7684	Intermediate Similarity	NPC154526
0.7684	Intermediate Similarity	NPC134072
0.7684	Intermediate Similarity	NPC234993
0.7684	Intermediate Similarity	NPC472363
0.7684	Intermediate Similarity	NPC472362
0.7677	Intermediate Similarity	NPC272632
0.7674	Intermediate Similarity	NPC80471
0.7674	Intermediate Similarity	NPC5908
0.7674	Intermediate Similarity	NPC110373
0.7674	Intermediate Similarity	NPC17550
0.7674	Intermediate Similarity	NPC233295
0.766	Intermediate Similarity	NPC477130
0.766	Intermediate Similarity	NPC477129
0.766	Intermediate Similarity	NPC324078
0.7654	Intermediate Similarity	NPC101622
0.7653	Intermediate Similarity	NPC32577
0.7653	Intermediate Similarity	NPC472552
0.7653	Intermediate Similarity	NPC31058
0.7653	Intermediate Similarity	NPC114540
0.7653	Intermediate Similarity	NPC469606
0.7653	Intermediate Similarity	NPC109195
0.7653	Intermediate Similarity	NPC155332
0.7653	Intermediate Similarity	NPC273005
0.7653	Intermediate Similarity	NPC475038
0.7653	Intermediate Similarity	NPC11956
0.7647	Intermediate Similarity	NPC476439
0.764	Intermediate Similarity	NPC302360
0.764	Intermediate Similarity	NPC32223
0.764	Intermediate Similarity	NPC306951
0.764	Intermediate Similarity	NPC102048
0.764	Intermediate Similarity	NPC318515
0.7634	Intermediate Similarity	NPC249034

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 NPC471795 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1429
0.2-0.3	3891
0.3-0.4	2519
0.4-0.5	736
0.5-0.6	283
0.6-0.7	136
0.7-0.8	4
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
0.7614	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7638	Approved
0.7526	Intermediate Similarity	NPD4225	Approved
0.7449	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD7639	Approved
0.7444	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1694	Approved
0.7115	Intermediate Similarity	NPD6686	Approved
0.7053	Intermediate Similarity	NPD6051	Approved
0.703	Intermediate Similarity	NPD5344	Discontinued
0.701	Intermediate Similarity	NPD6399	Phase 3
0.6979	Remote Similarity	NPD7838	Discovery
0.6979	Remote Similarity	NPD5785	Approved
0.6951	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7334	Approved
0.6915	Remote Similarity	NPD6409	Approved
0.6915	Remote Similarity	NPD6684	Approved
0.6915	Remote Similarity	NPD7146	Approved
0.6915	Remote Similarity	NPD7521	Approved
0.6915	Remote Similarity	NPD5330	Approved
0.6907	Remote Similarity	NPD7637	Suspended
0.6882	Remote Similarity	NPD3665	Phase 1
0.6882	Remote Similarity	NPD3666	Approved
0.6882	Remote Similarity	NPD3133	Approved
0.6848	Remote Similarity	NPD3667	Approved
0.6818	Remote Similarity	NPD6942	Approved
0.6818	Remote Similarity	NPD7339	Approved
0.6813	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD46	Approved
0.6804	Remote Similarity	NPD6698	Approved
0.6796	Remote Similarity	NPD7632	Discontinued
0.6771	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6903	Approved
0.6768	Remote Similarity	NPD7748	Approved
0.6765	Remote Similarity	NPD6648	Approved
0.6757	Remote Similarity	NPD7115	Discovery
0.6737	Remote Similarity	NPD3618	Phase 1
0.6735	Remote Similarity	NPD7515	Phase 2
0.6733	Remote Similarity	NPD7902	Approved
0.6733	Remote Similarity	NPD6084	Phase 2
0.6733	Remote Similarity	NPD6083	Phase 2
0.6729	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6926	Approved
0.6705	Remote Similarity	NPD6924	Approved
0.6703	Remote Similarity	NPD4195	Approved
0.6702	Remote Similarity	NPD4786	Approved
0.6702	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5695	Phase 3
0.6698	Remote Similarity	NPD5697	Approved
0.6697	Remote Similarity	NPD6053	Discontinued
0.6696	Remote Similarity	NPD7327	Approved
0.6696	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6637	Remote Similarity	NPD7516	Approved
0.6636	Remote Similarity	NPD6881	Approved
0.6636	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD6899	Approved
0.663	Remote Similarity	NPD4819	Approved
0.663	Remote Similarity	NPD4822	Approved
0.663	Remote Similarity	NPD4821	Approved
0.663	Remote Similarity	NPD7525	Registered
0.663	Remote Similarity	NPD4820	Approved
0.6629	Remote Similarity	NPD8039	Approved
0.6629	Remote Similarity	NPD8264	Approved
0.6627	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6675	Approved
0.6604	Remote Similarity	NPD7128	Approved
0.6604	Remote Similarity	NPD6402	Approved
0.6604	Remote Similarity	NPD5739	Approved
0.6598	Remote Similarity	NPD5737	Approved
0.6598	Remote Similarity	NPD6672	Approved
0.6596	Remote Similarity	NPD7154	Phase 3
0.6596	Remote Similarity	NPD5362	Discontinued
0.6596	Remote Similarity	NPD6695	Phase 3
0.6593	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4271	Approved
0.6593	Remote Similarity	NPD4268	Approved
0.6579	Remote Similarity	NPD8294	Approved
0.6579	Remote Similarity	NPD8377	Approved
0.6574	Remote Similarity	NPD6012	Approved
0.6574	Remote Similarity	NPD6014	Approved
0.6574	Remote Similarity	NPD6013	Approved
0.6566	Remote Similarity	NPD6411	Approved
0.6566	Remote Similarity	NPD5693	Phase 1
0.6566	Remote Similarity	NPD5284	Approved
0.6566	Remote Similarity	NPD5281	Approved
0.6566	Remote Similarity	NPD6079	Approved
0.6562	Remote Similarity	NPD5279	Phase 3
0.6562	Remote Similarity	NPD4519	Discontinued
0.6562	Remote Similarity	NPD4623	Approved
0.6556	Remote Similarity	NPD6933	Approved
0.6552	Remote Similarity	NPD7143	Approved
0.6552	Remote Similarity	NPD7144	Approved
0.6542	Remote Similarity	NPD5701	Approved
0.6531	Remote Similarity	NPD5328	Approved
0.6522	Remote Similarity	NPD8378	Approved
0.6522	Remote Similarity	NPD8380	Approved
0.6522	Remote Similarity	NPD8335	Approved
0.6522	Remote Similarity	NPD7503	Approved
0.6522	Remote Similarity	NPD7645	Phase 2
0.6522	Remote Similarity	NPD6929	Approved
0.6522	Remote Similarity	NPD8296	Approved
0.6522	Remote Similarity	NPD8379	Approved
0.6514	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6883	Approved
0.6514	Remote Similarity	NPD7102	Approved
0.6514	Remote Similarity	NPD7290	Approved
0.6505	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5696	Approved
0.65	Remote Similarity	NPD5779	Approved
0.65	Remote Similarity	NPD4202	Approved
0.65	Remote Similarity	NPD5778	Approved
0.6495	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7320	Approved
0.6477	Remote Similarity	NPD7150	Approved
0.6477	Remote Similarity	NPD7151	Approved
0.6477	Remote Similarity	NPD7152	Approved
0.6471	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5363	Approved
0.6455	Remote Similarity	NPD6650	Approved
0.6455	Remote Similarity	NPD8130	Phase 1
0.6455	Remote Similarity	NPD6869	Approved
0.6455	Remote Similarity	NPD6617	Approved
0.6455	Remote Similarity	NPD6847	Approved
0.6455	Remote Similarity	NPD6649	Approved
0.6452	Remote Similarity	NPD7514	Phase 3
0.6452	Remote Similarity	NPD6931	Approved
0.6452	Remote Similarity	NPD7509	Discontinued
0.6452	Remote Similarity	NPD6930	Phase 2
0.6452	Remote Similarity	NPD7332	Phase 2
0.6437	Remote Similarity	NPD6923	Approved
0.6437	Remote Similarity	NPD6922	Approved
0.6436	Remote Similarity	NPD7900	Approved
0.6436	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6372	Approved
0.6422	Remote Similarity	NPD6373	Approved
0.6421	Remote Similarity	NPD5332	Approved
0.6421	Remote Similarity	NPD5331	Approved
0.6413	Remote Similarity	NPD7145	Approved
0.6396	Remote Similarity	NPD6882	Approved
0.6396	Remote Similarity	NPD8297	Approved
0.6392	Remote Similarity	NPD4249	Approved
0.6389	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4194	Approved
0.6386	Remote Similarity	NPD4193	Approved
0.6386	Remote Similarity	NPD4191	Approved
0.6386	Remote Similarity	NPD368	Approved
0.6386	Remote Similarity	NPD4192	Approved
0.6383	Remote Similarity	NPD4790	Discontinued
0.6383	Remote Similarity	NPD6902	Approved
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD1695	Approved
0.6364	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4785	Approved
0.6333	Remote Similarity	NPD4784	Approved
0.6327	Remote Similarity	NPD7524	Approved
0.6327	Remote Similarity	NPD3573	Approved
0.6327	Remote Similarity	NPD4251	Approved
0.6327	Remote Similarity	NPD4250	Approved
0.6327	Remote Similarity	NPD7750	Discontinued
0.6321	Remote Similarity	NPD5211	Phase 2
0.6316	Remote Similarity	NPD6435	Approved
0.6316	Remote Similarity	NPD4270	Approved
0.6316	Remote Similarity	NPD4221	Approved
0.6316	Remote Similarity	NPD4269	Approved
0.6316	Remote Similarity	NPD4223	Phase 3
0.6311	Remote Similarity	NPD5221	Approved
0.6311	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5222	Approved
0.6306	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6932	Approved
0.6304	Remote Similarity	NPD6925	Approved
0.6304	Remote Similarity	NPD5776	Phase 2
0.6303	Remote Similarity	NPD7507	Approved
0.63	Remote Similarity	NPD5207	Approved
0.6289	Remote Similarity	NPD1696	Phase 3
0.6289	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4696	Approved
0.6286	Remote Similarity	NPD5285	Approved
0.6286	Remote Similarity	NPD5286	Approved
0.6277	Remote Similarity	NPD4695	Discontinued
0.6275	Remote Similarity	NPD5282	Discontinued
0.6263	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD5173	Approved
0.6239	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6412	Phase 2
0.6238	Remote Similarity	NPD8035	Phase 2
0.6238	Remote Similarity	NPD5694	Approved
0.6238	Remote Similarity	NPD8034	Phase 2
0.6226	Remote Similarity	NPD5223	Approved
0.6224	Remote Similarity	NPD5690	Phase 2
0.6224	Remote Similarity	NPD5786	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