NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	266.942
LogP:	1.078
LogD:	0.941
LogS:	-3.111
# Rotatable Bonds:	2
TPSA:	55.9
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.432
Synthetic Accessibility Score:	4.981
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.709
MDCK Permeability:	1.4320091395347845e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	61.039405822753906%
Volume Distribution (VD):	1.204
Pgp-substrate:	48.76415252685547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.297
CYP1A2-substrate:	0.203
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.506
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	6.406
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.174
Human Hepatotoxicity (H-HT):	0.96
Drug-inuced Liver Injury (DILI):	0.767
AMES Toxicity:	0.164
Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.923
Carcinogencity:	0.595
Eye Corrosion:	0.954
Eye Irritation:	0.953
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC62815

Natural Product ID:	NPC62815
*Common Name:**	8-Epixanthatin-1Beta,5Beta-Epoxide
IUPAC Name:	(1aR,2S,3aR,6aR,7aR)-2-methyl-6-methylidene-1a-[(E)-3-oxobut-1-enyl]-2,3,3a,6a,7,7a-hexahydrooxireno[6,7]cyclohepta[1,2-b]furan-5-one
Synonyms:
Standard InCHIKey:	NGAVJIMZMAIVPV-ODTBHIJQSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-8-6-12-11(10(3)14(17)18-12)7-13-15(8,19-13)5-4-9(2)16/h4-5,8,11-13H,3,6-7H2,1-2H3/b5-4+/t8-,11+,12+,13+,15-/m0/s1
SMILES:	C[C@H]1C[C@@H]2[C@H](C[C@@H]3[C@@]1(/C=C/C(=O)C)O3)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380789
PubChem CID:	14633043
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:0000502] Xanthanolides

*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
NPO32861	xanthium brasilicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO8815	Artemisia myriantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32842729]
NPO8815	Artemisia myriantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8815	Artemisia myriantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8815	Artemisia myriantha	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
IC50	6

Activity Type	# Activity
Cell Line	3
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[456533]
NPT1229	Cell Line	Huh-7	Homo sapiens	IC50	=	8200.0	nM	PMID[456533]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[456533]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	13212.96	nM	PMID[456532]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[456532]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	13220.0	nM	PMID[456532]

☑ 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 NPC62815 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	237
0.1-0.2	1484
0.2-0.3	5633
0.3-0.4	11900
0.4-0.5	13330
0.5-0.6	6435
0.6-0.7	2757
0.7-0.8	804
0.8-0.85	93
0.85-0.9	23
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8977	High Similarity	NPC166919
0.8966	High Similarity	NPC475703
0.8966	High Similarity	NPC231889
0.8941	High Similarity	NPC272814
0.8889	High Similarity	NPC135776
0.8876	High Similarity	NPC312042
0.8778	High Similarity	NPC20713
0.875	High Similarity	NPC474741
0.8736	High Similarity	NPC474547
0.8721	High Similarity	NPC39588
0.8696	High Similarity	NPC474947
0.8667	High Similarity	NPC329857
0.8667	High Similarity	NPC469718
0.8667	High Similarity	NPC475748
0.8636	High Similarity	NPC50637
0.8636	High Similarity	NPC470242
0.8587	High Similarity	NPC476267
0.8587	High Similarity	NPC140543
0.8587	High Similarity	NPC473316
0.8587	High Similarity	NPC473330
0.8556	High Similarity	NPC151770
0.8556	High Similarity	NPC4986
0.8556	High Similarity	NPC32922
0.8523	High Similarity	NPC161957
0.8495	Intermediate Similarity	NPC304886
0.8488	Intermediate Similarity	NPC141810
0.8462	Intermediate Similarity	NPC49342
0.8462	Intermediate Similarity	NPC251385
0.8454	Intermediate Similarity	NPC475945
0.8454	Intermediate Similarity	NPC475871
0.8438	Intermediate Similarity	NPC474742
0.8427	Intermediate Similarity	NPC64153
0.8427	Intermediate Similarity	NPC284902
0.8421	Intermediate Similarity	NPC208233
0.8404	Intermediate Similarity	NPC476275
0.8387	Intermediate Similarity	NPC477131
0.8387	Intermediate Similarity	NPC474035
0.8387	Intermediate Similarity	NPC81386
0.837	Intermediate Similarity	NPC284185
0.837	Intermediate Similarity	NPC74103
0.837	Intermediate Similarity	NPC150978
0.837	Intermediate Similarity	NPC70595
0.837	Intermediate Similarity	NPC123177
0.8351	Intermediate Similarity	NPC474747
0.8333	Intermediate Similarity	NPC270270
0.8333	Intermediate Similarity	NPC118601
0.8315	Intermediate Similarity	NPC319795
0.8315	Intermediate Similarity	NPC215364
0.8315	Intermediate Similarity	NPC38468
0.8315	Intermediate Similarity	NPC50362
0.8298	Intermediate Similarity	NPC14961
0.8298	Intermediate Similarity	NPC270013
0.8295	Intermediate Similarity	NPC170377
0.8295	Intermediate Similarity	NPC318468
0.8283	Intermediate Similarity	NPC223450
0.8283	Intermediate Similarity	NPC243998
0.828	Intermediate Similarity	NPC228451
0.828	Intermediate Similarity	NPC212486
0.828	Intermediate Similarity	NPC125674
0.828	Intermediate Similarity	NPC475838
0.8276	Intermediate Similarity	NPC301477
0.8276	Intermediate Similarity	NPC25684
0.8276	Intermediate Similarity	NPC281949
0.8261	Intermediate Similarity	NPC144133
0.8261	Intermediate Similarity	NPC179394
0.8261	Intermediate Similarity	NPC51004
0.8261	Intermediate Similarity	NPC253144
0.8256	Intermediate Similarity	NPC617
0.8242	Intermediate Similarity	NPC224652
0.8242	Intermediate Similarity	NPC202672
0.8242	Intermediate Similarity	NPC178875
0.8235	Intermediate Similarity	NPC65603
0.8229	Intermediate Similarity	NPC473326
0.8222	Intermediate Similarity	NPC474045
0.8222	Intermediate Similarity	NPC107787
0.8222	Intermediate Similarity	NPC469676
0.8222	Intermediate Similarity	NPC261253
0.8211	Intermediate Similarity	NPC35498
0.8211	Intermediate Similarity	NPC476315
0.8202	Intermediate Similarity	NPC472957
0.8202	Intermediate Similarity	NPC138647
0.8202	Intermediate Similarity	NPC472958
0.8202	Intermediate Similarity	NPC470238
0.8191	Intermediate Similarity	NPC470013
0.8191	Intermediate Similarity	NPC470010
0.8191	Intermediate Similarity	NPC471147
0.8191	Intermediate Similarity	NPC323008
0.8191	Intermediate Similarity	NPC474247
0.8191	Intermediate Similarity	NPC303942
0.8191	Intermediate Similarity	NPC262133
0.8191	Intermediate Similarity	NPC57405
0.8182	Intermediate Similarity	NPC203659
0.8172	Intermediate Similarity	NPC261607
0.8172	Intermediate Similarity	NPC221282
0.8172	Intermediate Similarity	NPC133698
0.8172	Intermediate Similarity	NPC111114
0.8172	Intermediate Similarity	NPC300312
0.8172	Intermediate Similarity	NPC131209
0.8172	Intermediate Similarity	NPC30515
0.8161	Intermediate Similarity	NPC474510
0.8161	Intermediate Similarity	NPC74673
0.8161	Intermediate Similarity	NPC69271
0.8152	Intermediate Similarity	NPC295312
0.8152	Intermediate Similarity	NPC307411
0.8152	Intermediate Similarity	NPC78008
0.8144	Intermediate Similarity	NPC288876
0.8132	Intermediate Similarity	NPC160138
0.8111	Intermediate Similarity	NPC21471
0.8111	Intermediate Similarity	NPC78089
0.8111	Intermediate Similarity	NPC33570
0.8111	Intermediate Similarity	NPC235792
0.8105	Intermediate Similarity	NPC275960
0.8105	Intermediate Similarity	NPC475659
0.8105	Intermediate Similarity	NPC48803
0.8105	Intermediate Similarity	NPC90121
0.8105	Intermediate Similarity	NPC193645
0.809	Intermediate Similarity	NPC250315
0.809	Intermediate Similarity	NPC53867
0.809	Intermediate Similarity	NPC474472
0.809	Intermediate Similarity	NPC257358
0.8085	Intermediate Similarity	NPC475912
0.8085	Intermediate Similarity	NPC81419
0.8085	Intermediate Similarity	NPC476300
0.8085	Intermediate Similarity	NPC179746
0.8081	Intermediate Similarity	NPC110989
0.8081	Intermediate Similarity	NPC475873
0.8068	Intermediate Similarity	NPC35089
0.8068	Intermediate Similarity	NPC47635
0.8068	Intermediate Similarity	NPC10276
0.8065	Intermediate Similarity	NPC475855
0.8061	Intermediate Similarity	NPC476270
0.8061	Intermediate Similarity	NPC264477
0.8061	Intermediate Similarity	NPC477511
0.8046	Intermediate Similarity	NPC63649
0.8046	Intermediate Similarity	NPC264227
0.8046	Intermediate Similarity	NPC472965
0.8043	Intermediate Similarity	NPC91248
0.8043	Intermediate Similarity	NPC475902
0.8041	Intermediate Similarity	NPC221615
0.8041	Intermediate Similarity	NPC141191
0.8041	Intermediate Similarity	NPC279561
0.8041	Intermediate Similarity	NPC54843
0.8023	Intermediate Similarity	NPC476794
0.8023	Intermediate Similarity	NPC470240
0.8022	Intermediate Similarity	NPC122502
0.8021	Intermediate Similarity	NPC473859
0.8021	Intermediate Similarity	NPC279621
0.8021	Intermediate Similarity	NPC230800
0.8021	Intermediate Similarity	NPC17585
0.8	Intermediate Similarity	NPC115786
0.8	Intermediate Similarity	NPC226669
0.8	Intermediate Similarity	NPC193351
0.8	Intermediate Similarity	NPC167219
0.8	Intermediate Similarity	NPC471143
0.8	Intermediate Similarity	NPC138408
0.8	Intermediate Similarity	NPC477510
0.8	Intermediate Similarity	NPC198853
0.798	Intermediate Similarity	NPC149371
0.798	Intermediate Similarity	NPC225353
0.7979	Intermediate Similarity	NPC184463
0.7979	Intermediate Similarity	NPC12172
0.7979	Intermediate Similarity	NPC208886
0.7978	Intermediate Similarity	NPC246076
0.7978	Intermediate Similarity	NPC173609
0.7959	Intermediate Similarity	NPC477512
0.7957	Intermediate Similarity	NPC268298
0.7957	Intermediate Similarity	NPC472872
0.7955	Intermediate Similarity	NPC276356
0.7955	Intermediate Similarity	NPC223904
0.7955	Intermediate Similarity	NPC302426
0.7938	Intermediate Similarity	NPC213947
0.7938	Intermediate Similarity	NPC170143
0.7938	Intermediate Similarity	NPC108475
0.7938	Intermediate Similarity	NPC169205
0.7935	Intermediate Similarity	NPC5130
0.7931	Intermediate Similarity	NPC128276
0.7931	Intermediate Similarity	NPC472960
0.7921	Intermediate Similarity	NPC54737
0.7917	Intermediate Similarity	NPC52044
0.7917	Intermediate Similarity	NPC36954
0.7917	Intermediate Similarity	NPC476053
0.7917	Intermediate Similarity	NPC471141
0.7917	Intermediate Similarity	NPC67584
0.7917	Intermediate Similarity	NPC107476
0.7912	Intermediate Similarity	NPC197903
0.7912	Intermediate Similarity	NPC165162
0.7912	Intermediate Similarity	NPC99395
0.7907	Intermediate Similarity	NPC235906
0.7895	Intermediate Similarity	NPC153590
0.7889	Intermediate Similarity	NPC170286
0.7889	Intermediate Similarity	NPC54468
0.7889	Intermediate Similarity	NPC475842
0.7882	Intermediate Similarity	NPC476355
0.7879	Intermediate Similarity	NPC47880
0.7879	Intermediate Similarity	NPC171759
0.7879	Intermediate Similarity	NPC201718
0.7879	Intermediate Similarity	NPC474339
0.7879	Intermediate Similarity	NPC164598
0.7872	Intermediate Similarity	NPC71533
0.7872	Intermediate Similarity	NPC301969

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 NPC62815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	1984
0.2-0.3	3923
0.3-0.4	2061
0.4-0.5	675
0.5-0.6	248
0.6-0.7	39
0.7-0.8	5
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8556	High Similarity	NPD1695	Approved
0.8315	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD1694	Approved
0.75	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6371	Approved
0.732	Intermediate Similarity	NPD46	Approved
0.732	Intermediate Similarity	NPD6698	Approved
0.7238	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7021	Intermediate Similarity	NPD5209	Approved
0.7021	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5785	Approved
0.6941	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5282	Discontinued
0.6847	Remote Similarity	NPD6053	Discontinued
0.6804	Remote Similarity	NPD5363	Approved
0.6762	Remote Similarity	NPD6648	Approved
0.6735	Remote Similarity	NPD5786	Approved
0.6733	Remote Similarity	NPD7983	Approved
0.6698	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6566	Remote Similarity	NPD4249	Approved
0.6562	Remote Similarity	NPD5369	Approved
0.6545	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4251	Approved
0.65	Remote Similarity	NPD4250	Approved
0.6495	Remote Similarity	NPD4270	Approved
0.6495	Remote Similarity	NPD4269	Approved
0.6486	Remote Similarity	NPD6686	Approved
0.6466	Remote Similarity	NPD7115	Discovery
0.646	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5368	Approved
0.6429	Remote Similarity	NPD5362	Discontinued
0.6429	Remote Similarity	NPD7154	Phase 3
0.6372	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4225	Approved
0.6355	Remote Similarity	NPD7638	Approved
0.6337	Remote Similarity	NPD3573	Approved
0.63	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7639	Approved
0.6296	Remote Similarity	NPD7640	Approved
0.6289	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4819	Approved
0.6289	Remote Similarity	NPD4821	Approved
0.6289	Remote Similarity	NPD4252	Approved
0.6289	Remote Similarity	NPD4822	Approved
0.6289	Remote Similarity	NPD4820	Approved
0.6283	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7642	Approved
0.6277	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD8513	Phase 3
0.625	Remote Similarity	NPD8516	Approved
0.625	Remote Similarity	NPD8515	Approved
0.625	Remote Similarity	NPD8517	Approved
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6684	Approved
0.6238	Remote Similarity	NPD7334	Approved
0.6238	Remote Similarity	NPD7521	Approved
0.6238	Remote Similarity	NPD7146	Approved
0.6238	Remote Similarity	NPD6409	Approved
0.6238	Remote Similarity	NPD5330	Approved
0.6226	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6101	Approved
0.6207	Remote Similarity	NPD4632	Approved
0.6195	Remote Similarity	NPD6881	Approved
0.6195	Remote Similarity	NPD6899	Approved
0.6195	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD7260	Phase 2
0.619	Remote Similarity	NPD6399	Phase 3
0.6174	Remote Similarity	NPD6650	Approved
0.6174	Remote Similarity	NPD6649	Approved
0.6168	Remote Similarity	NPD7839	Suspended
0.6154	Remote Similarity	NPD5207	Approved
0.614	Remote Similarity	NPD6014	Approved
0.614	Remote Similarity	NPD6013	Approved
0.614	Remote Similarity	NPD6012	Approved
0.6132	Remote Similarity	NPD7900	Approved
0.6132	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6672	Approved
0.6117	Remote Similarity	NPD6903	Approved
0.6117	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5737	Approved
0.6095	Remote Similarity	NPD6411	Approved
0.6087	Remote Similarity	NPD7102	Approved
0.6087	Remote Similarity	NPD6883	Approved
0.6087	Remote Similarity	NPD7290	Approved
0.6082	Remote Similarity	NPD4271	Approved
0.6082	Remote Similarity	NPD4268	Approved
0.605	Remote Similarity	NPD6009	Approved
0.6034	Remote Similarity	NPD6847	Approved
0.6034	Remote Similarity	NPD6617	Approved
0.6034	Remote Similarity	NPD8130	Phase 1
0.6034	Remote Similarity	NPD6869	Approved
0.6033	Remote Similarity	NPD6319	Approved
0.6018	Remote Similarity	NPD5739	Approved
0.6018	Remote Similarity	NPD6675	Approved
0.6018	Remote Similarity	NPD7128	Approved
0.6018	Remote Similarity	NPD6402	Approved
0.6016	Remote Similarity	NPD7604	Phase 2
0.6016	Remote Similarity	NPD7830	Approved
0.6016	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD6373	Approved
0.5984	Remote Similarity	NPD5983	Phase 2
0.5983	Remote Similarity	NPD6882	Approved
0.5983	Remote Similarity	NPD8297	Approved
0.5981	Remote Similarity	NPD6001	Approved
0.5968	Remote Similarity	NPD7492	Approved
0.5965	Remote Similarity	NPD5701	Approved
0.5963	Remote Similarity	NPD7902	Approved
0.5954	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5284	Approved
0.5943	Remote Similarity	NPD5694	Approved
0.5943	Remote Similarity	NPD5281	Approved
0.5941	Remote Similarity	NPD5331	Approved
0.5941	Remote Similarity	NPD5332	Approved
0.5934	Remote Similarity	NPD7331	Phase 2
0.5926	Remote Similarity	NPD5695	Phase 3
0.592	Remote Similarity	NPD7507	Approved
0.592	Remote Similarity	NPD6616	Approved
0.592	Remote Similarity	NPD8273	Phase 1
0.5913	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7320	Approved
0.5909	Remote Similarity	NPD5696	Approved
0.5905	Remote Similarity	NPD6673	Approved
0.5905	Remote Similarity	NPD6080	Approved
0.5905	Remote Similarity	NPD6904	Approved
0.5902	Remote Similarity	NPD6054	Approved
0.59	Remote Similarity	NPD4790	Discontinued
0.5897	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5211	Phase 2
0.5891	Remote Similarity	NPD6845	Suspended
0.5873	Remote Similarity	NPD7078	Approved
0.5868	Remote Similarity	NPD7641	Discontinued
0.5856	Remote Similarity	NPD5285	Approved
0.5856	Remote Similarity	NPD5286	Approved
0.5856	Remote Similarity	NPD4696	Approved
0.5854	Remote Similarity	NPD6016	Approved
0.5854	Remote Similarity	NPD6015	Approved
0.5854	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5692	Phase 3
0.5842	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7748	Approved
0.5827	Remote Similarity	NPD7736	Approved
0.5824	Remote Similarity	NPD7341	Phase 2
0.5818	Remote Similarity	NPD6084	Phase 2
0.5818	Remote Similarity	NPD6083	Phase 2
0.5816	Remote Similarity	NPD4756	Discovery
0.5812	Remote Similarity	NPD2067	Discontinued
0.581	Remote Similarity	NPD5208	Approved
0.5806	Remote Similarity	NPD6370	Approved
0.5806	Remote Similarity	NPD5988	Approved
0.5804	Remote Similarity	NPD5223	Approved
0.5794	Remote Similarity	NPD6050	Approved
0.5794	Remote Similarity	NPD6336	Discontinued
0.5794	Remote Similarity	NPD7637	Suspended
0.5794	Remote Similarity	NPD6079	Approved
0.5789	Remote Similarity	NPD5141	Approved
0.5785	Remote Similarity	NPD6317	Approved
0.5784	Remote Similarity	NPD6110	Phase 1
0.5781	Remote Similarity	NPD7319	Approved
0.5769	Remote Similarity	NPD6422	Discontinued
0.5763	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5370	Suspended
0.5755	Remote Similarity	NPD6051	Approved
0.5752	Remote Similarity	NPD5226	Approved
0.5752	Remote Similarity	NPD4633	Approved
0.5752	Remote Similarity	NPD5224	Approved
0.5752	Remote Similarity	NPD5225	Approved
0.5752	Remote Similarity	NPD7632	Discontinued
0.5738	Remote Similarity	NPD6313	Approved
0.5738	Remote Similarity	NPD6335	Approved
0.5738	Remote Similarity	NPD6314	Approved
0.5727	Remote Similarity	NPD5221	Approved
0.5727	Remote Similarity	NPD5222	Approved
0.5727	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6274	Approved
0.5702	Remote Similarity	NPD5175	Approved
0.5702	Remote Similarity	NPD5174	Approved
0.5699	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7100	Approved
0.5691	Remote Similarity	NPD7101	Approved
0.569	Remote Similarity	NPD6412	Phase 2
0.5678	Remote Similarity	NPD4634	Approved
0.5676	Remote Similarity	NPD5173	Approved
0.5676	Remote Similarity	NPD4755	Approved
0.5673	Remote Similarity	NPD1696	Phase 3
0.5669	Remote Similarity	NPD8451	Approved
0.5656	Remote Similarity	NPD7500	Approved
0.5648	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD7515	Phase 2
0.5645	Remote Similarity	NPD6059	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