NPASS Compound

Structure

NPC475842 OpenBabel07101718322D 29 31 0 0 1 0 0 0 0 0999 V2000 -3.8756 1.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7839 -3.9794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0937 -1.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4899 -2.1724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3603 -2.2672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4167 1.6271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3425 1.3524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6411 -0.8440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4174 1.1893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3607 -1.4478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3425 -1.3524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4174 -1.1893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7125 -2.4117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1560 0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6667 -3.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8756 -1.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1560 -0.8827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2435 -1.1265 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8135 0.4697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4773 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4167 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1686 -1.2897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8135 -0.4697 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3863 -4.2619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8864 -0.8135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8864 0.8135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8298 -2.7330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8473 -0.4069 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 14 2 0 0 0 0 2 15 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 6 26 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 19 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 27 1 0 0 0 0 14 20 1 0 0 0 0 15 24 2 0 0 0 0 15 27 1 0 0 0 0 17 16 1 6 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 0 0 0 0 19 23 1 6 0 0 0 19 29 1 0 0 0 0 20 21 1 1 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 22 28 1 0 0 0 0 23 5 1 6 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.24
Volume:	422.89
LogP:	3.874
LogD:	3.256
LogS:	-4.381
# Rotatable Bonds:	8
TPSA:	77.66
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	4.946
Fsp3:	0.739
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.733
MDCK Permeability:	2.4095877961372025e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	85.17215728759766%
Volume Distribution (VD):	1.107
Pgp-substrate:	11.291985511779785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.247
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.231
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.657

ADMET: Excretion

Clearance (CL):	5.423
Half-life (T1/2):	0.254

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.491
Drug-inuced Liver Injury (DILI):	0.41
AMES Toxicity:	0.218
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.658
Carcinogencity:	0.678
Eye Corrosion:	0.007
Eye Irritation:	0.027
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC475842

Natural Product ID:	NPC475842
*Common Name:**	Xenitacin
IUPAC Name:	methyl (1S,5R,6S,9S)-6-[(E)-1-acetyloxy-4-(3,3-dimethyloxiran-2-yl)but-2-en-2-yl]-9-methyl-4-methylidene-10-oxabicyclo[7.1.0]decane-5-carboxylate
Synonyms:	Xenitacin
Standard InCHIKey:	IUVFOVFYOYFLRB-CUAQSNGHSA-N
Standard InCHI:	InChI=1S/C23H34O6/c1-14-7-9-19-23(5,29-19)12-11-17(20(14)21(25)26-6)16(13-27-15(2)24)8-10-18-22(3,4)28-18/h8,17-20H,1,7,9-13H2,2-6H3/b16-8-/t17-,18?,19+,20+,23+/m1/s1
SMILES:	COC(=O)[C@H]1C(=C)CC[C@H]2[C@](CC[C@@H]1/C(=CCC1OC1(C)C)/COC(=O)C)(O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517188
PubChem CID:	10341296
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic acids 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
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[12502332]
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562830]
NPO14298	Xenia umbellata	Species	Xeniidae	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	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.26	ug ml-1	PMID[527143]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.12	ug ml-1	PMID[527143]
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.09	ug ml-1	PMID[527143]

☑ 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 NPC475842 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	244
0.1-0.2	1797
0.2-0.3	6444
0.3-0.4	16867
0.4-0.5	9866
0.5-0.6	5870
0.6-0.7	1447
0.7-0.8	153
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9367	High Similarity	NPC475936
0.9036	High Similarity	NPC474765
0.9024	High Similarity	NPC474547
0.878	High Similarity	NPC53867
0.8625	High Similarity	NPC474341
0.8481	Intermediate Similarity	NPC475861
0.8452	Intermediate Similarity	NPC474776
0.8333	Intermediate Similarity	NPC170377
0.8333	Intermediate Similarity	NPC477084
0.8256	Intermediate Similarity	NPC474045
0.8256	Intermediate Similarity	NPC261253
0.8182	Intermediate Similarity	NPC115179
0.8182	Intermediate Similarity	NPC106040
0.8161	Intermediate Similarity	NPC475703
0.8161	Intermediate Similarity	NPC231889
0.814	Intermediate Similarity	NPC474369
0.8132	Intermediate Similarity	NPC107476
0.8118	Intermediate Similarity	NPC272814
0.8118	Intermediate Similarity	NPC475989
0.8095	Intermediate Similarity	NPC475481
0.8095	Intermediate Similarity	NPC79277
0.8095	Intermediate Similarity	NPC141810
0.809	Intermediate Similarity	NPC475748
0.8077	Intermediate Similarity	NPC269841
0.8046	Intermediate Similarity	NPC469676
0.8046	Intermediate Similarity	NPC116575
0.8046	Intermediate Similarity	NPC50637
0.8	Intermediate Similarity	NPC135703
0.8	Intermediate Similarity	NPC35556
0.7978	Intermediate Similarity	NPC166919
0.7976	Intermediate Similarity	NPC474739
0.7976	Intermediate Similarity	NPC474510
0.7975	Intermediate Similarity	NPC475310
0.7927	Intermediate Similarity	NPC271070
0.7889	Intermediate Similarity	NPC62815
0.7857	Intermediate Similarity	NPC617
0.7841	Intermediate Similarity	NPC122502
0.7831	Intermediate Similarity	NPC84360
0.7826	Intermediate Similarity	NPC471147
0.7802	Intermediate Similarity	NPC475972
0.7802	Intermediate Similarity	NPC20713
0.7789	Intermediate Similarity	NPC475053
0.7778	Intermediate Similarity	NPC475971
0.7778	Intermediate Similarity	NPC151770
0.7778	Intermediate Similarity	NPC212598
0.7742	Intermediate Similarity	NPC272050
0.7727	Intermediate Similarity	NPC137033
0.7727	Intermediate Similarity	NPC99395
0.7727	Intermediate Similarity	NPC197903
0.7717	Intermediate Similarity	NPC476049
0.7711	Intermediate Similarity	NPC301525
0.7701	Intermediate Similarity	NPC11620
0.7692	Intermediate Similarity	NPC474761
0.7692	Intermediate Similarity	NPC329857
0.7692	Intermediate Similarity	NPC476004
0.7692	Intermediate Similarity	NPC469718
0.7692	Intermediate Similarity	NPC312042
0.7692	Intermediate Similarity	NPC51004
0.7684	Intermediate Similarity	NPC208233
0.7683	Intermediate Similarity	NPC140287
0.7674	Intermediate Similarity	NPC471325
0.7667	Intermediate Similarity	NPC474471
0.7667	Intermediate Similarity	NPC233997
0.7667	Intermediate Similarity	NPC281516
0.7667	Intermediate Similarity	NPC227379
0.766	Intermediate Similarity	NPC476315
0.764	Intermediate Similarity	NPC137253
0.764	Intermediate Similarity	NPC284902
0.7634	Intermediate Similarity	NPC81386
0.7634	Intermediate Similarity	NPC476267
0.7634	Intermediate Similarity	NPC140543
0.7634	Intermediate Similarity	NPC473316
0.7634	Intermediate Similarity	NPC473330
0.7634	Intermediate Similarity	NPC474035
0.7619	Intermediate Similarity	NPC470240
0.7619	Intermediate Similarity	NPC107668
0.7619	Intermediate Similarity	NPC476794
0.7614	Intermediate Similarity	NPC470238
0.7614	Intermediate Similarity	NPC72464
0.7614	Intermediate Similarity	NPC138647
0.7609	Intermediate Similarity	NPC30515
0.7609	Intermediate Similarity	NPC221282
0.759	Intermediate Similarity	NPC244166
0.759	Intermediate Similarity	NPC324762
0.759	Intermediate Similarity	NPC474419
0.7582	Intermediate Similarity	NPC307411
0.7579	Intermediate Similarity	NPC471140
0.7556	Intermediate Similarity	NPC248602
0.7553	Intermediate Similarity	NPC14961
0.7553	Intermediate Similarity	NPC270013
0.7553	Intermediate Similarity	NPC474947
0.7529	Intermediate Similarity	NPC474005
0.7529	Intermediate Similarity	NPC128276
0.7528	Intermediate Similarity	NPC50362
0.7528	Intermediate Similarity	NPC38468
0.7528	Intermediate Similarity	NPC215364
0.7528	Intermediate Similarity	NPC319795
0.7528	Intermediate Similarity	NPC235792
0.7527	Intermediate Similarity	NPC212486
0.7527	Intermediate Similarity	NPC125674
0.7527	Intermediate Similarity	NPC228451
0.7527	Intermediate Similarity	NPC476300
0.7527	Intermediate Similarity	NPC475838
0.7526	Intermediate Similarity	NPC477511
0.7526	Intermediate Similarity	NPC264477
0.75	Intermediate Similarity	NPC474703
0.75	Intermediate Similarity	NPC257358
0.75	Intermediate Similarity	NPC250315
0.75	Intermediate Similarity	NPC474472
0.75	Intermediate Similarity	NPC222358
0.75	Intermediate Similarity	NPC475622
0.75	Intermediate Similarity	NPC108045
0.75	Intermediate Similarity	NPC318468
0.75	Intermediate Similarity	NPC235906
0.7474	Intermediate Similarity	NPC35498
0.7473	Intermediate Similarity	NPC153805
0.7473	Intermediate Similarity	NPC202672
0.7473	Intermediate Similarity	NPC475902
0.7471	Intermediate Similarity	NPC301477
0.7471	Intermediate Similarity	NPC25684
0.7471	Intermediate Similarity	NPC325031
0.7471	Intermediate Similarity	NPC281949
0.7471	Intermediate Similarity	NPC207188
0.747	Intermediate Similarity	NPC476355
0.747	Intermediate Similarity	NPC474551
0.747	Intermediate Similarity	NPC474758
0.7447	Intermediate Similarity	NPC474247
0.7444	Intermediate Similarity	NPC234038
0.7444	Intermediate Similarity	NPC220478
0.7444	Intermediate Similarity	NPC471480
0.7444	Intermediate Similarity	NPC164393
0.7442	Intermediate Similarity	NPC469620
0.7442	Intermediate Similarity	NPC178277
0.7442	Intermediate Similarity	NPC471740
0.7442	Intermediate Similarity	NPC469690
0.7439	Intermediate Similarity	NPC129665
0.7439	Intermediate Similarity	NPC163003
0.7419	Intermediate Similarity	NPC184463
0.7416	Intermediate Similarity	NPC196487
0.7416	Intermediate Similarity	NPC9868
0.7416	Intermediate Similarity	NPC82297
0.7416	Intermediate Similarity	NPC14575
0.7412	Intermediate Similarity	NPC65603
0.7412	Intermediate Similarity	NPC57744
0.7412	Intermediate Similarity	NPC97516
0.7407	Intermediate Similarity	NPC101622
0.7391	Intermediate Similarity	NPC295312
0.7391	Intermediate Similarity	NPC83423
0.7391	Intermediate Similarity	NPC473564
0.7391	Intermediate Similarity	NPC4986
0.7386	Intermediate Similarity	NPC173609
0.7386	Intermediate Similarity	NPC89555
0.7381	Intermediate Similarity	NPC93213
0.7368	Intermediate Similarity	NPC36954
0.7368	Intermediate Similarity	NPC475659
0.7363	Intermediate Similarity	NPC74139
0.7363	Intermediate Similarity	NPC160138
0.7363	Intermediate Similarity	NPC475087
0.7356	Intermediate Similarity	NPC474981
0.7356	Intermediate Similarity	NPC103634
0.7356	Intermediate Similarity	NPC475946
0.7349	Intermediate Similarity	NPC238425
0.7349	Intermediate Similarity	NPC472018
0.7349	Intermediate Similarity	NPC474543
0.7349	Intermediate Similarity	NPC477085
0.734	Intermediate Similarity	NPC475912
0.734	Intermediate Similarity	NPC179746
0.734	Intermediate Similarity	NPC81419
0.7333	Intermediate Similarity	NPC47958
0.7333	Intermediate Similarity	NPC149725
0.7333	Intermediate Similarity	NPC304509
0.7333	Intermediate Similarity	NPC96621
0.7333	Intermediate Similarity	NPC78089
0.7326	Intermediate Similarity	NPC23187
0.732	Intermediate Similarity	NPC474213
0.732	Intermediate Similarity	NPC279561
0.7317	Intermediate Similarity	NPC469660
0.7317	Intermediate Similarity	NPC472955
0.7317	Intermediate Similarity	NPC4299
0.7312	Intermediate Similarity	NPC51653
0.7312	Intermediate Similarity	NPC316228
0.7312	Intermediate Similarity	NPC473448
0.7312	Intermediate Similarity	NPC251385
0.7312	Intermediate Similarity	NPC49342
0.7303	Intermediate Similarity	NPC170286
0.7303	Intermediate Similarity	NPC231601
0.7303	Intermediate Similarity	NPC193198
0.73	Intermediate Similarity	NPC477510
0.73	Intermediate Similarity	NPC471143
0.7294	Intermediate Similarity	NPC110461
0.7294	Intermediate Similarity	NPC61863
0.7294	Intermediate Similarity	NPC123360
0.7294	Intermediate Similarity	NPC474447
0.7294	Intermediate Similarity	NPC474527
0.7294	Intermediate Similarity	NPC12740
0.7294	Intermediate Similarity	NPC471726
0.7292	Intermediate Similarity	NPC279621
0.7292	Intermediate Similarity	NPC476275
0.7292	Intermediate Similarity	NPC473859
0.7292	Intermediate Similarity	NPC230800

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 NPC475842 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	2402
0.2-0.3	3825
0.3-0.4	1908
0.4-0.5	603
0.5-0.6	130
0.6-0.7	23
0.7-0.8	3
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
0.7528	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.7391	Intermediate Similarity	NPD1695	Approved
0.7342	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5778	Approved
0.6979	Remote Similarity	NPD5779	Approved
0.6977	Remote Similarity	NPD8039	Approved
0.6947	Remote Similarity	NPD7838	Discovery
0.6923	Remote Similarity	NPD5362	Discontinued
0.6923	Remote Similarity	NPD7154	Phase 3
0.69	Remote Similarity	NPD6648	Approved
0.6875	Remote Similarity	NPD7983	Approved
0.6832	Remote Similarity	NPD5344	Discontinued
0.6703	Remote Similarity	NPD5369	Approved
0.6702	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6371	Approved
0.663	Remote Similarity	NPD5209	Approved
0.663	Remote Similarity	NPD6435	Approved
0.663	Remote Similarity	NPD4269	Approved
0.663	Remote Similarity	NPD4270	Approved
0.6598	Remote Similarity	NPD5785	Approved
0.6596	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1694	Approved
0.6593	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4819	Approved
0.6593	Remote Similarity	NPD4821	Approved
0.6593	Remote Similarity	NPD4822	Approved
0.6593	Remote Similarity	NPD4820	Approved
0.6556	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6411	Approved
0.6514	Remote Similarity	NPD6053	Discontinued
0.6509	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7638	Approved
0.6458	Remote Similarity	NPD4251	Approved
0.6458	Remote Similarity	NPD4250	Approved
0.6436	Remote Similarity	NPD7839	Suspended
0.6421	Remote Similarity	NPD5363	Approved
0.6415	Remote Similarity	NPD6008	Approved
0.6413	Remote Similarity	NPD5368	Approved
0.6413	Remote Similarity	NPD4252	Approved
0.6408	Remote Similarity	NPD7640	Approved
0.6408	Remote Similarity	NPD7639	Approved
0.6389	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5331	Approved
0.6383	Remote Similarity	NPD5332	Approved
0.6374	Remote Similarity	NPD4268	Approved
0.6374	Remote Similarity	NPD4271	Approved
0.6354	Remote Similarity	NPD7334	Approved
0.6354	Remote Similarity	NPD6409	Approved
0.6354	Remote Similarity	NPD5330	Approved
0.6354	Remote Similarity	NPD6422	Discontinued
0.6354	Remote Similarity	NPD7146	Approved
0.6354	Remote Similarity	NPD6684	Approved
0.6354	Remote Similarity	NPD7521	Approved
0.6354	Remote Similarity	NPD4249	Approved
0.6344	Remote Similarity	NPD4790	Discontinued
0.633	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6051	Approved
0.6311	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6399	Phase 3
0.6296	Remote Similarity	NPD6686	Approved
0.6273	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5737	Approved
0.6224	Remote Similarity	NPD6903	Approved
0.6224	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6672	Approved
0.62	Remote Similarity	NPD5693	Phase 1
0.614	Remote Similarity	NPD7115	Discovery
0.6104	Remote Similarity	NPD6927	Phase 3
0.6078	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7900	Approved
0.6078	Remote Similarity	NPD7748	Approved
0.6078	Remote Similarity	NPD5282	Discontinued
0.6047	Remote Similarity	NPD7331	Phase 2
0.604	Remote Similarity	NPD7637	Suspended
0.602	Remote Similarity	NPD6098	Approved
0.6019	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4225	Approved
0.5977	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.596	Remote Similarity	NPD3573	Approved
0.5941	Remote Similarity	NPD3168	Discontinued
0.5932	Remote Similarity	NPD8513	Phase 3
0.5932	Remote Similarity	NPD8516	Approved
0.5932	Remote Similarity	NPD8515	Approved
0.5932	Remote Similarity	NPD8517	Approved
0.593	Remote Similarity	NPD7341	Phase 2
0.5905	Remote Similarity	NPD7902	Approved
0.5905	Remote Similarity	NPD6083	Phase 2
0.5905	Remote Similarity	NPD6084	Phase 2
0.5897	Remote Similarity	NPD28	Approved
0.5897	Remote Similarity	NPD29	Approved
0.5882	Remote Similarity	NPD6050	Approved
0.5882	Remote Similarity	NPD7515	Phase 2
0.5868	Remote Similarity	NPD8273	Phase 1
0.5865	Remote Similarity	NPD5695	Phase 3
0.5842	Remote Similarity	NPD5370	Suspended
0.5833	Remote Similarity	NPD7632	Discontinued
0.5818	Remote Similarity	NPD6675	Approved
0.5818	Remote Similarity	NPD7128	Approved
0.5818	Remote Similarity	NPD5739	Approved
0.5818	Remote Similarity	NPD6402	Approved
0.5816	Remote Similarity	NPD3668	Phase 3
0.5816	Remote Similarity	NPD4786	Approved
0.5816	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD3197	Phase 1
0.5784	Remote Similarity	NPD5692	Phase 3
0.5773	Remote Similarity	NPD3667	Approved
0.5769	Remote Similarity	NPD6001	Approved
0.5745	Remote Similarity	NPD4756	Discovery
0.5743	Remote Similarity	NPD5208	Approved
0.5738	Remote Similarity	NPD7507	Approved
0.5728	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5694	Approved
0.5714	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD6110	Phase 1
0.5714	Remote Similarity	NPD6899	Approved
0.5714	Remote Similarity	NPD6695	Phase 3
0.5714	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7642	Approved
0.5702	Remote Similarity	NPD7830	Approved
0.5702	Remote Similarity	NPD7829	Approved
0.5701	Remote Similarity	NPD5696	Approved
0.5691	Remote Similarity	NPD8074	Phase 3
0.5688	Remote Similarity	NPD3653	Clinical (unspecified phase)
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
0.5664	Remote Similarity	NPD6372	Approved
0.5664	Remote Similarity	NPD6373	Approved
0.566	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD7909	Approved
0.5631	Remote Similarity	NPD5207	Approved
0.5625	Remote Similarity	NPD5697	Approved
0.5625	Remote Similarity	NPD5701	Approved
0.5614	Remote Similarity	NPD7102	Approved
0.5614	Remote Similarity	NPD7290	Approved
0.5614	Remote Similarity	NPD6883	Approved
0.5612	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.561	Remote Similarity	NPD8451	Approved
0.561	Remote Similarity	NPD6637	Approved
0.56	Remote Similarity	NPD7319	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