NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	2.2
LogD:	2.608
LogS:	-2.968
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	4.659
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.735
MDCK Permeability:	1.4805303180764895e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.142

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.767
Plasma Protein Binding (PPB):	70.31818389892578%
Volume Distribution (VD):	0.861
Pgp-substrate:	28.28299331665039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.163
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.146
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.692
CYP3A4-substrate:	0.361

ADMET: Excretion

Clearance (CL):	7.195
Half-life (T1/2):	0.263

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.27
Carcinogencity:	0.712
Eye Corrosion:	0.046
Eye Irritation:	0.159
Respiratory Toxicity:	0.552

Download Data

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

Natural Product: NPC253604

Natural Product ID:	NPC253604
*Common Name:**	4Beta,8Beta-Dihydroxy-5Alpha(H)-Eudesm-7(11)-En-8,12-Olide
IUPAC Name:	(4aR,5S,8aR,9aS)-5,9a-dihydroxy-3,5,8a-trimethyl-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
Synonyms:
Standard InCHIKey:	VMMYFJSUBISYEJ-RZFFKMDDSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-9-10-7-11-13(2,5-4-6-14(11,3)17)8-15(10,18)19-12(9)16/h11,17-18H,4-8H2,1-3H3/t11-,13-,14+,15+/m1/s1
SMILES:	CC1=C2C[C@@H]3[C@](C)(CCC[C@]3(C)O)C[C@]2(O)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036052
PubChem CID:	57409865
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:0001772] Eudesmanolides, secoeudesmanolides, 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
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053511]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22372956]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588583]
NPO26787	Chloranthus anhuiensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29775304]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724564]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26787	Chloranthus anhuiensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	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	>	10000.0	nM	PMID[485312]

☑ 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 NPC253604 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	194
0.1-0.2	1466
0.2-0.3	5152
0.3-0.4	11322
0.4-0.5	12233
0.5-0.6	7594
0.6-0.7	4128
0.7-0.8	549
0.8-0.85	38
0.85-0.9	16
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9294	High Similarity	NPC78594
0.9167	High Similarity	NPC242448
0.9146	High Similarity	NPC32223
0.8977	High Similarity	NPC471915
0.8966	High Similarity	NPC472641
0.8966	High Similarity	NPC472640
0.8953	High Similarity	NPC472642
0.8889	High Similarity	NPC10636
0.8587	High Similarity	NPC16601
0.8556	High Similarity	NPC111273
0.8539	High Similarity	NPC110022
0.8462	Intermediate Similarity	NPC165632
0.8404	Intermediate Similarity	NPC471914
0.8387	Intermediate Similarity	NPC324841
0.8333	Intermediate Similarity	NPC7349
0.8316	Intermediate Similarity	NPC471938
0.8242	Intermediate Similarity	NPC105490
0.8229	Intermediate Similarity	NPC471937
0.8222	Intermediate Similarity	NPC329842
0.8222	Intermediate Similarity	NPC472811
0.8222	Intermediate Similarity	NPC289479
0.8191	Intermediate Similarity	NPC476767
0.8152	Intermediate Similarity	NPC472441
0.8132	Intermediate Similarity	NPC472812
0.8132	Intermediate Similarity	NPC472303
0.8068	Intermediate Similarity	NPC131813
0.8068	Intermediate Similarity	NPC471219
0.8065	Intermediate Similarity	NPC234993
0.8065	Intermediate Similarity	NPC134072
0.8043	Intermediate Similarity	NPC57117
0.8021	Intermediate Similarity	NPC58329
0.8021	Intermediate Similarity	NPC475038
0.8021	Intermediate Similarity	NPC472815
0.8021	Intermediate Similarity	NPC109195
0.8	Intermediate Similarity	NPC471413
0.798	Intermediate Similarity	NPC181994
0.7957	Intermediate Similarity	NPC329435
0.7957	Intermediate Similarity	NPC276110
0.7938	Intermediate Similarity	NPC120009
0.7938	Intermediate Similarity	NPC474822
0.7938	Intermediate Similarity	NPC471208
0.7938	Intermediate Similarity	NPC45897
0.7931	Intermediate Similarity	NPC476927
0.7917	Intermediate Similarity	NPC471412
0.7912	Intermediate Similarity	NPC78973
0.7895	Intermediate Similarity	NPC325229
0.7895	Intermediate Similarity	NPC275086
0.7889	Intermediate Similarity	NPC472809
0.7889	Intermediate Similarity	NPC472810
0.7879	Intermediate Similarity	NPC471205
0.7879	Intermediate Similarity	NPC122816
0.7872	Intermediate Similarity	NPC29952
0.7857	Intermediate Similarity	NPC189206
0.7849	Intermediate Similarity	NPC470255
0.7841	Intermediate Similarity	NPC474693
0.7835	Intermediate Similarity	NPC121423
0.7835	Intermediate Similarity	NPC162973
0.7835	Intermediate Similarity	NPC476769
0.7826	Intermediate Similarity	NPC473675
0.7812	Intermediate Similarity	NPC251680
0.7812	Intermediate Similarity	NPC38855
0.7802	Intermediate Similarity	NPC170633
0.78	Intermediate Similarity	NPC325054
0.78	Intermediate Similarity	NPC38948
0.7789	Intermediate Similarity	NPC51499
0.7789	Intermediate Similarity	NPC205143
0.7778	Intermediate Similarity	NPC473891
0.7778	Intermediate Similarity	NPC51719
0.7755	Intermediate Similarity	NPC281378
0.7753	Intermediate Similarity	NPC475860
0.7753	Intermediate Similarity	NPC474694
0.7753	Intermediate Similarity	NPC473659
0.7742	Intermediate Similarity	NPC205034
0.7742	Intermediate Similarity	NPC139692
0.7742	Intermediate Similarity	NPC53555
0.7742	Intermediate Similarity	NPC162615
0.7742	Intermediate Similarity	NPC152778
0.7732	Intermediate Similarity	NPC295110
0.7732	Intermediate Similarity	NPC222875
0.7732	Intermediate Similarity	NPC25177
0.7732	Intermediate Similarity	NPC268829
0.7732	Intermediate Similarity	NPC247701
0.7732	Intermediate Similarity	NPC11974
0.7727	Intermediate Similarity	NPC311070
0.7723	Intermediate Similarity	NPC31522
0.7723	Intermediate Similarity	NPC206618
0.7717	Intermediate Similarity	NPC221111
0.7717	Intermediate Similarity	NPC182136
0.7717	Intermediate Similarity	NPC280149
0.7717	Intermediate Similarity	NPC477782
0.7717	Intermediate Similarity	NPC310479
0.7708	Intermediate Similarity	NPC278673
0.7708	Intermediate Similarity	NPC474440
0.7708	Intermediate Similarity	NPC218107
0.7701	Intermediate Similarity	NPC170303
0.77	Intermediate Similarity	NPC475074
0.7692	Intermediate Similarity	NPC106332
0.7684	Intermediate Similarity	NPC209297
0.7684	Intermediate Similarity	NPC242848
0.7684	Intermediate Similarity	NPC475380
0.7684	Intermediate Similarity	NPC319861
0.7684	Intermediate Similarity	NPC473153
0.7677	Intermediate Similarity	NPC472819
0.7677	Intermediate Similarity	NPC161775
0.7667	Intermediate Similarity	NPC474062
0.766	Intermediate Similarity	NPC474555
0.766	Intermediate Similarity	NPC140277
0.766	Intermediate Similarity	NPC474554
0.7653	Intermediate Similarity	NPC295791
0.7653	Intermediate Similarity	NPC165250
0.7653	Intermediate Similarity	NPC472552
0.7653	Intermediate Similarity	NPC476081
0.7647	Intermediate Similarity	NPC132542
0.764	Intermediate Similarity	NPC290052
0.764	Intermediate Similarity	NPC471302
0.764	Intermediate Similarity	NPC102048
0.7634	Intermediate Similarity	NPC72845
0.7634	Intermediate Similarity	NPC477783
0.7634	Intermediate Similarity	NPC41239
0.7629	Intermediate Similarity	NPC472826
0.7629	Intermediate Similarity	NPC477716
0.7629	Intermediate Similarity	NPC477721
0.7624	Intermediate Similarity	NPC476765
0.7624	Intermediate Similarity	NPC300614
0.7624	Intermediate Similarity	NPC90946
0.7614	Intermediate Similarity	NPC2524
0.7609	Intermediate Similarity	NPC470734
0.7609	Intermediate Similarity	NPC474396
0.7609	Intermediate Similarity	NPC50488
0.7604	Intermediate Similarity	NPC199099
0.7604	Intermediate Similarity	NPC100912
0.7604	Intermediate Similarity	NPC475446
0.7604	Intermediate Similarity	NPC477719
0.7604	Intermediate Similarity	NPC477718
0.7604	Intermediate Similarity	NPC287668
0.7604	Intermediate Similarity	NPC311241
0.76	Intermediate Similarity	NPC218158
0.76	Intermediate Similarity	NPC472818
0.7586	Intermediate Similarity	NPC469802
0.7582	Intermediate Similarity	NPC166857
0.7576	Intermediate Similarity	NPC196471
0.7576	Intermediate Similarity	NPC10232
0.7576	Intermediate Similarity	NPC165608
0.7576	Intermediate Similarity	NPC159533
0.7576	Intermediate Similarity	NPC97487
0.7576	Intermediate Similarity	NPC120321
0.7576	Intermediate Similarity	NPC23584
0.7576	Intermediate Similarity	NPC160583
0.7576	Intermediate Similarity	NPC472821
0.7576	Intermediate Similarity	NPC187302
0.7576	Intermediate Similarity	NPC189588
0.7556	Intermediate Similarity	NPC146850
0.7556	Intermediate Similarity	NPC30984
0.7556	Intermediate Similarity	NPC473251
0.7556	Intermediate Similarity	NPC42586
0.7556	Intermediate Similarity	NPC474013
0.7556	Intermediate Similarity	NPC65661
0.7556	Intermediate Similarity	NPC287015
0.7553	Intermediate Similarity	NPC472871
0.7551	Intermediate Similarity	NPC472554
0.7551	Intermediate Similarity	NPC477717
0.7551	Intermediate Similarity	NPC198992
0.7549	Intermediate Similarity	NPC475030
0.7549	Intermediate Similarity	NPC322912
0.7528	Intermediate Similarity	NPC321385
0.7526	Intermediate Similarity	NPC473154
0.7526	Intermediate Similarity	NPC107806
0.7526	Intermediate Similarity	NPC72647
0.7525	Intermediate Similarity	NPC67321
0.7525	Intermediate Similarity	NPC302788
0.7525	Intermediate Similarity	NPC216636
0.7525	Intermediate Similarity	NPC187435
0.7525	Intermediate Similarity	NPC472820
0.7525	Intermediate Similarity	NPC319438
0.75	Intermediate Similarity	NPC194132
0.75	Intermediate Similarity	NPC291665
0.75	Intermediate Similarity	NPC93411
0.75	Intermediate Similarity	NPC16967
0.75	Intermediate Similarity	NPC17578
0.75	Intermediate Similarity	NPC240673
0.75	Intermediate Similarity	NPC202833
0.7476	Intermediate Similarity	NPC476766
0.7476	Intermediate Similarity	NPC472666
0.7476	Intermediate Similarity	NPC177047
0.7475	Intermediate Similarity	NPC11956
0.7474	Intermediate Similarity	NPC279410
0.7474	Intermediate Similarity	NPC161998
0.7474	Intermediate Similarity	NPC469697
0.7474	Intermediate Similarity	NPC191521
0.7474	Intermediate Similarity	NPC119562
0.7473	Intermediate Similarity	NPC329692
0.7471	Intermediate Similarity	NPC5908
0.7471	Intermediate Similarity	NPC110373
0.7471	Intermediate Similarity	NPC80471
0.7451	Intermediate Similarity	NPC50124
0.7451	Intermediate Similarity	NPC306265
0.7449	Intermediate Similarity	NPC161527
0.7449	Intermediate Similarity	NPC477972
0.7449	Intermediate Similarity	NPC20113
0.7449	Intermediate Similarity	NPC470761

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 NPC253604 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1819
0.2-0.3	4001
0.3-0.4	2224
0.4-0.5	555
0.5-0.6	280
0.6-0.7	88
0.7-0.8	9
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
0.7812	Intermediate Similarity	NPD7640	Approved
0.7812	Intermediate Similarity	NPD7639	Approved
0.7708	Intermediate Similarity	NPD7638	Approved
0.7653	Intermediate Similarity	NPD7632	Discontinued
0.7379	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4225	Approved
0.7308	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6686	Approved
0.7019	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.6937	Remote Similarity	NPD7516	Approved
0.6875	Remote Similarity	NPD8377	Approved
0.6875	Remote Similarity	NPD8294	Approved
0.6814	Remote Similarity	NPD8380	Approved
0.6814	Remote Similarity	NPD8378	Approved
0.6814	Remote Similarity	NPD8296	Approved
0.6814	Remote Similarity	NPD8335	Approved
0.6814	Remote Similarity	NPD8033	Approved
0.6814	Remote Similarity	NPD8379	Approved
0.6724	Remote Similarity	NPD7507	Approved
0.6702	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5344	Discontinued
0.6632	Remote Similarity	NPD1694	Approved
0.6602	Remote Similarity	NPD6648	Approved
0.66	Remote Similarity	NPD7748	Approved
0.6566	Remote Similarity	NPD5693	Phase 1
0.6555	Remote Similarity	NPD7319	Approved
0.6522	Remote Similarity	NPD7503	Approved
0.6495	Remote Similarity	NPD3573	Approved
0.646	Remote Similarity	NPD7115	Discovery
0.6408	Remote Similarity	NPD7902	Approved
0.64	Remote Similarity	NPD7637	Suspended
0.64	Remote Similarity	NPD7515	Phase 2
0.6392	Remote Similarity	NPD4623	Approved
0.6392	Remote Similarity	NPD4519	Discontinued
0.6392	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6051	Approved
0.6346	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6009	Approved
0.6296	Remote Similarity	NPD5739	Approved
0.6296	Remote Similarity	NPD6675	Approved
0.6296	Remote Similarity	NPD6008	Approved
0.6296	Remote Similarity	NPD7128	Approved
0.6296	Remote Similarity	NPD6402	Approved
0.6273	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD6695	Phase 3
0.625	Remote Similarity	NPD6882	Approved
0.6239	Remote Similarity	NPD5701	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6237	Remote Similarity	NPD3617	Approved
0.6224	Remote Similarity	NPD3618	Phase 1
0.6214	Remote Similarity	NPD5695	Phase 3
0.6214	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6080	Approved
0.62	Remote Similarity	NPD6673	Approved
0.62	Remote Similarity	NPD6904	Approved
0.6195	Remote Similarity	NPD4632	Approved
0.6195	Remote Similarity	NPD8133	Approved
0.619	Remote Similarity	NPD5696	Approved
0.6186	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6011	Approved
0.6182	Remote Similarity	NPD6899	Approved
0.6182	Remote Similarity	NPD6881	Approved
0.6182	Remote Similarity	NPD7320	Approved
0.6176	Remote Similarity	NPD6399	Phase 3
0.617	Remote Similarity	NPD4195	Approved
0.6146	Remote Similarity	NPD4223	Phase 3
0.6146	Remote Similarity	NPD4221	Approved
0.6126	Remote Similarity	NPD6373	Approved
0.6126	Remote Similarity	NPD6014	Approved
0.6126	Remote Similarity	NPD6372	Approved
0.6126	Remote Similarity	NPD6012	Approved
0.6126	Remote Similarity	NPD6013	Approved
0.6117	Remote Similarity	NPD7900	Approved
0.6117	Remote Similarity	NPD6001	Approved
0.6117	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4695	Discontinued
0.6105	Remote Similarity	NPD7525	Registered
0.61	Remote Similarity	NPD5737	Approved
0.61	Remote Similarity	NPD6672	Approved
0.61	Remote Similarity	NPD5208	Approved
0.6091	Remote Similarity	NPD6412	Phase 2
0.6083	Remote Similarity	NPD7492	Approved
0.6078	Remote Similarity	NPD5284	Approved
0.6078	Remote Similarity	NPD8034	Phase 2
0.6078	Remote Similarity	NPD5281	Approved
0.6078	Remote Similarity	NPD8035	Phase 2
0.6071	Remote Similarity	NPD7290	Approved
0.6071	Remote Similarity	NPD7102	Approved
0.6071	Remote Similarity	NPD6883	Approved
0.6061	Remote Similarity	NPD7146	Approved
0.6061	Remote Similarity	NPD5330	Approved
0.6061	Remote Similarity	NPD7521	Approved
0.6061	Remote Similarity	NPD6409	Approved
0.6061	Remote Similarity	NPD6684	Approved
0.6061	Remote Similarity	NPD7334	Approved
0.604	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5328	Approved
0.6036	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6616	Approved
0.602	Remote Similarity	NPD4197	Approved
0.6019	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD5779	Approved
0.6019	Remote Similarity	NPD5211	Phase 2
0.6019	Remote Similarity	NPD5778	Approved
0.6018	Remote Similarity	NPD6650	Approved
0.6018	Remote Similarity	NPD6847	Approved
0.6018	Remote Similarity	NPD6649	Approved
0.6018	Remote Similarity	NPD8130	Phase 1
0.6018	Remote Similarity	NPD6869	Approved
0.6018	Remote Similarity	NPD6617	Approved
0.6018	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6054	Approved
0.6017	Remote Similarity	NPD6319	Approved
0.6017	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD7524	Approved
0.5984	Remote Similarity	NPD8293	Discontinued
0.5984	Remote Similarity	NPD7078	Approved
0.598	Remote Similarity	NPD7838	Discovery
0.598	Remote Similarity	NPD6698	Approved
0.598	Remote Similarity	NPD46	Approved
0.598	Remote Similarity	NPD5692	Phase 3
0.5966	Remote Similarity	NPD6015	Approved
0.5966	Remote Similarity	NPD5983	Phase 2
0.5966	Remote Similarity	NPD6016	Approved
0.5965	Remote Similarity	NPD6053	Discontinued
0.5965	Remote Similarity	NPD8297	Approved
0.596	Remote Similarity	NPD1696	Phase 3
0.596	Remote Similarity	NPD5329	Approved
0.596	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD4755	Approved
0.5941	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6903	Approved
0.5938	Remote Similarity	NPD6931	Approved
0.5938	Remote Similarity	NPD6930	Phase 2
0.5935	Remote Similarity	NPD7736	Approved
0.5929	Remote Similarity	NPD6371	Approved
0.5922	Remote Similarity	NPD6079	Approved
0.5922	Remote Similarity	NPD6050	Approved
0.5922	Remote Similarity	NPD5694	Approved
0.5917	Remote Similarity	NPD5988	Approved
0.5917	Remote Similarity	NPD6370	Approved
0.5909	Remote Similarity	NPD5141	Approved
0.59	Remote Similarity	NPD4690	Approved
0.59	Remote Similarity	NPD6098	Approved
0.59	Remote Similarity	NPD4689	Approved
0.59	Remote Similarity	NPD4693	Phase 3
0.59	Remote Similarity	NPD4138	Approved
0.59	Remote Similarity	NPD5205	Approved
0.59	Remote Similarity	NPD4688	Approved
0.5897	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6114	Approved
0.5895	Remote Similarity	NPD6118	Approved
0.5895	Remote Similarity	NPD6697	Approved
0.5895	Remote Similarity	NPD6115	Approved
0.5882	Remote Similarity	NPD4753	Phase 2
0.5868	Remote Similarity	NPD7604	Phase 2
0.5868	Remote Similarity	NPD8328	Phase 3
0.5859	Remote Similarity	NPD3665	Phase 1
0.5859	Remote Similarity	NPD3133	Approved
0.5859	Remote Similarity	NPD3666	Approved
0.5849	Remote Similarity	NPD5222	Approved
0.5849	Remote Similarity	NPD4697	Phase 3
0.5849	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5221	Approved
0.5833	Remote Similarity	NPD7645	Phase 2
0.5833	Remote Similarity	NPD5285	Approved
0.5833	Remote Similarity	NPD6929	Approved
0.5833	Remote Similarity	NPD5286	Approved
0.5833	Remote Similarity	NPD4696	Approved
0.5833	Remote Similarity	NPD4700	Approved
0.5825	Remote Similarity	NPD5207	Approved
0.5825	Remote Similarity	NPD5785	Approved
0.5816	Remote Similarity	NPD3667	Approved
0.5812	Remote Similarity	NPD6274	Approved
0.5795	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5173	Approved
0.578	Remote Similarity	NPD4159	Approved
0.578	Remote Similarity	NPD5223	Approved
0.5773	Remote Similarity	NPD7332	Phase 2
0.5773	Remote Similarity	NPD7514	Phase 3
0.5772	Remote Similarity	NPD6336	Discontinued
0.5769	Remote Similarity	NPD7087	Discontinued
0.5763	Remote Similarity	NPD6317	Approved
0.5761	Remote Similarity	NPD4243	Approved
0.5758	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD3669	Approved
0.5755	Remote Similarity	NPD5654	Approved
0.5755	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4694	Approved
0.5743	Remote Similarity	NPD5280	Approved
0.5743	Remote Similarity	NPD5690	Phase 2
0.5739	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6067	Discontinued

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