NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	534.21
Volume:	507.72
LogP:	2.063
LogD:	1.179
LogS:	-4.032
# Rotatable Bonds:	4
TPSA:	165.26
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.384
Synthetic Accessibility Score:	6.144
Fsp3:	0.741
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.509
MDCK Permeability:	1.131066801463021e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.845
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.407
Plasma Protein Binding (PPB):	54.194271087646484%
Volume Distribution (VD):	0.728
Pgp-substrate:	36.26000213623047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.749
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.372
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.243
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	10.081
Half-life (T1/2):	0.837

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.571
AMES Toxicity:	0.221
Rat Oral Acute Toxicity:	0.855
Maximum Recommended Daily Dose:	0.826
Skin Sensitization:	0.187
Carcinogencity:	0.147
Eye Corrosion:	0.004
Eye Irritation:	0.051
Respiratory Toxicity:	0.883

Download Data

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

Natural Product: NPC476851

Natural Product ID:	NPC476851
*Common Name:**	methyl 2-[(1R,2R,4S,7R,8S,10S,11R,12R,13R,16R)-10-hydroxy-7-(2-hydroxy-5-oxo-2H-furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.02,4.02,8.012,16]octadecan-13-yl]acetate
IUPAC Name:	methyl 2-[(1R,2R,4S,7R,8S,10S,11R,12R,13R,16R)-10-hydroxy-7-(2-hydroxy-5-oxo-2H-furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.02,4.02,8.012,16]octadecan-13-yl]acetate
Synonyms:
Standard InCHIKey:	XVYDOXSQOXSOED-PDJNUNDDSA-N
Standard InCHI:	InChI=1S/C27H34O11/c1-23(2)13-8-14(29)26(5)18(25(13,4)15(37-23)9-16(30)34-6)12(28)10-24(3)19(11-7-17(31)35-21(11)32)36-22(33)20-27(24,26)38-20/h7,12-13,15,18-21,28,32H,8-10H2,1-6H3/t12-,13-,15+,18+,19-,20+,21?,24-,25+,26+,27+/m0/s1
SMILES:	C[C@@]12C[C@@H]([C@@H]3[C@@]4([C@@H](CC(=O)[C@]3([C@@]15[C@H](O5)C(=O)O[C@H]2C6=CC(=O)OC6O)C)C(O[C@@H]4CC(=O)OC)(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90670768
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO33678	Clausena emarginata	Species	Rutaceae	Eukaryota	stems	Xishuangbanna, Yunnan Province, China	2010-AUG	PMID[24593150]

☑ 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	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT1820	Cell Line	NCI-H1650	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT2	Others	Unspecified		IC50	>	10000	nM	PMID[24593150]

☑ 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 NPC476851 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	290
0.1-0.2	1646
0.2-0.3	4803
0.3-0.4	7873
0.4-0.5	11528
0.5-0.6	8214
0.6-0.7	5607
0.7-0.8	2480
0.8-0.85	229
0.85-0.9	20
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9916	High Similarity	NPC476852
0.9748	High Similarity	NPC476859
0.9667	High Similarity	NPC476854
0.9587	High Similarity	NPC476855
0.9426	High Similarity	NPC476863
0.9426	High Similarity	NPC476862
0.871	High Similarity	NPC470922
0.871	High Similarity	NPC476729
0.8651	High Similarity	NPC473620
0.8629	High Similarity	NPC67251
0.8629	High Similarity	NPC265557
0.8629	High Similarity	NPC18945
0.8629	High Similarity	NPC105926
0.8629	High Similarity	NPC91693
0.8618	High Similarity	NPC470779
0.8615	High Similarity	NPC251998
0.8605	High Similarity	NPC471234
0.8571	High Similarity	NPC42399
0.8571	High Similarity	NPC298841
0.855	High Similarity	NPC295885
0.855	High Similarity	NPC140045
0.8548	High Similarity	NPC312833
0.8538	High Similarity	NPC262813
0.8527	High Similarity	NPC168879
0.8512	High Similarity	NPC213084
0.8512	High Similarity	NPC190185
0.8473	Intermediate Similarity	NPC190065
0.8473	Intermediate Similarity	NPC471089
0.8473	Intermediate Similarity	NPC141215
0.8468	Intermediate Similarity	NPC102822
0.8468	Intermediate Similarity	NPC477046
0.8455	Intermediate Similarity	NPC268958
0.845	Intermediate Similarity	NPC102316
0.843	Intermediate Similarity	NPC299849
0.8425	Intermediate Similarity	NPC476008
0.8425	Intermediate Similarity	NPC470780
0.8413	Intermediate Similarity	NPC24651
0.8409	Intermediate Similarity	NPC596
0.8387	Intermediate Similarity	NPC112038
0.8387	Intermediate Similarity	NPC107338
0.8387	Intermediate Similarity	NPC109607
0.8385	Intermediate Similarity	NPC88668
0.8374	Intermediate Similarity	NPC297179
0.8374	Intermediate Similarity	NPC240509
0.8359	Intermediate Similarity	NPC311534
0.8347	Intermediate Similarity	NPC94509
0.8346	Intermediate Similarity	NPC477745
0.8346	Intermediate Similarity	NPC225049
0.8308	Intermediate Similarity	NPC478154
0.8306	Intermediate Similarity	NPC476529
0.8306	Intermediate Similarity	NPC475775
0.8295	Intermediate Similarity	NPC175186
0.8295	Intermediate Similarity	NPC473593
0.8295	Intermediate Similarity	NPC104382
0.8295	Intermediate Similarity	NPC472770
0.8293	Intermediate Similarity	NPC474483
0.8293	Intermediate Similarity	NPC13713
0.8293	Intermediate Similarity	NPC146432
0.8293	Intermediate Similarity	NPC470778
0.8281	Intermediate Similarity	NPC117702
0.8281	Intermediate Similarity	NPC287423
0.8281	Intermediate Similarity	NPC469757
0.8281	Intermediate Similarity	NPC471357
0.8281	Intermediate Similarity	NPC146456
0.8264	Intermediate Similarity	NPC317687
0.8258	Intermediate Similarity	NPC171619
0.825	Intermediate Similarity	NPC472666
0.8244	Intermediate Similarity	NPC478151
0.824	Intermediate Similarity	NPC48692
0.8231	Intermediate Similarity	NPC471170
0.8231	Intermediate Similarity	NPC478155
0.8231	Intermediate Similarity	NPC476074
0.8231	Intermediate Similarity	NPC329993
0.8231	Intermediate Similarity	NPC475377
0.8231	Intermediate Similarity	NPC134914
0.8231	Intermediate Similarity	NPC478065
0.8231	Intermediate Similarity	NPC301639
0.8231	Intermediate Similarity	NPC475167
0.8231	Intermediate Similarity	NPC264566
0.8231	Intermediate Similarity	NPC173435
0.8231	Intermediate Similarity	NPC262796
0.8231	Intermediate Similarity	NPC172374
0.8231	Intermediate Similarity	NPC45346
0.8231	Intermediate Similarity	NPC478064
0.8231	Intermediate Similarity	NPC25998
0.8226	Intermediate Similarity	NPC17772
0.8226	Intermediate Similarity	NPC251310
0.8226	Intermediate Similarity	NPC188667
0.8226	Intermediate Similarity	NPC470776
0.8226	Intermediate Similarity	NPC204552
0.8211	Intermediate Similarity	NPC270478
0.8211	Intermediate Similarity	NPC235539
0.8211	Intermediate Similarity	NPC474046
0.8211	Intermediate Similarity	NPC471816
0.8211	Intermediate Similarity	NPC134869
0.8211	Intermediate Similarity	NPC89929
0.8211	Intermediate Similarity	NPC470628
0.8211	Intermediate Similarity	NPC152199
0.8211	Intermediate Similarity	NPC259306
0.8209	Intermediate Similarity	NPC477233
0.8209	Intermediate Similarity	NPC477232
0.8203	Intermediate Similarity	NPC285091
0.8203	Intermediate Similarity	NPC222307
0.8197	Intermediate Similarity	NPC159333
0.8197	Intermediate Similarity	NPC264153
0.8195	Intermediate Similarity	NPC243014
0.8189	Intermediate Similarity	NPC27363
0.8189	Intermediate Similarity	NPC120724
0.8189	Intermediate Similarity	NPC472768
0.8182	Intermediate Similarity	NPC317107
0.8175	Intermediate Similarity	NPC471999
0.8175	Intermediate Similarity	NPC472000
0.8168	Intermediate Similarity	NPC180902
0.8168	Intermediate Similarity	NPC472769
0.8168	Intermediate Similarity	NPC478152
0.8168	Intermediate Similarity	NPC478150
0.8168	Intermediate Similarity	NPC478153
0.8168	Intermediate Similarity	NPC231240
0.8168	Intermediate Similarity	NPC475139
0.8154	Intermediate Similarity	NPC10823
0.8154	Intermediate Similarity	NPC6108
0.8154	Intermediate Similarity	NPC251866
0.8154	Intermediate Similarity	NPC471352
0.8154	Intermediate Similarity	NPC219085
0.8154	Intermediate Similarity	NPC471359
0.8154	Intermediate Similarity	NPC17896
0.8154	Intermediate Similarity	NPC469751
0.8154	Intermediate Similarity	NPC471358
0.8154	Intermediate Similarity	NPC284406
0.8154	Intermediate Similarity	NPC469754
0.8154	Intermediate Similarity	NPC471361
0.8154	Intermediate Similarity	NPC197707
0.8154	Intermediate Similarity	NPC477196
0.8154	Intermediate Similarity	NPC469753
0.8154	Intermediate Similarity	NPC180079
0.8154	Intermediate Similarity	NPC86159
0.8154	Intermediate Similarity	NPC70542
0.8154	Intermediate Similarity	NPC89514
0.8154	Intermediate Similarity	NPC9499
0.8154	Intermediate Similarity	NPC471360
0.8154	Intermediate Similarity	NPC469752
0.8154	Intermediate Similarity	NPC469755
0.8145	Intermediate Similarity	NPC473968
0.8145	Intermediate Similarity	NPC470854
0.8145	Intermediate Similarity	NPC469684
0.8145	Intermediate Similarity	NPC470775
0.8145	Intermediate Similarity	NPC97908
0.8145	Intermediate Similarity	NPC176513
0.8145	Intermediate Similarity	NPC473590
0.8145	Intermediate Similarity	NPC287343
0.8145	Intermediate Similarity	NPC122033
0.8145	Intermediate Similarity	NPC474654
0.813	Intermediate Similarity	NPC181145
0.813	Intermediate Similarity	NPC474906
0.813	Intermediate Similarity	NPC18547
0.813	Intermediate Similarity	NPC473798
0.813	Intermediate Similarity	NPC469877
0.813	Intermediate Similarity	NPC470919
0.8125	Intermediate Similarity	NPC8369
0.8116	Intermediate Similarity	NPC48813
0.8116	Intermediate Similarity	NPC194854
0.8115	Intermediate Similarity	NPC269530
0.811	Intermediate Similarity	NPC473231
0.811	Intermediate Similarity	NPC471965
0.8106	Intermediate Similarity	NPC316915
0.8099	Intermediate Similarity	NPC476766
0.8095	Intermediate Similarity	NPC476150
0.8095	Intermediate Similarity	NPC109973
0.8095	Intermediate Similarity	NPC476127
0.8095	Intermediate Similarity	NPC472004
0.8092	Intermediate Similarity	NPC477197
0.8083	Intermediate Similarity	NPC476765
0.8083	Intermediate Similarity	NPC322903
0.808	Intermediate Similarity	NPC234522
0.8077	Intermediate Similarity	NPC477078
0.8077	Intermediate Similarity	NPC475636
0.8077	Intermediate Similarity	NPC477191
0.8077	Intermediate Similarity	NPC329923
0.8077	Intermediate Similarity	NPC470475
0.8077	Intermediate Similarity	NPC477194
0.8077	Intermediate Similarity	NPC477192
0.8077	Intermediate Similarity	NPC295220
0.8077	Intermediate Similarity	NPC477075
0.8077	Intermediate Similarity	NPC475281
0.8077	Intermediate Similarity	NPC470476
0.8077	Intermediate Similarity	NPC477193
0.8077	Intermediate Similarity	NPC188291
0.8077	Intermediate Similarity	NPC270109
0.8065	Intermediate Similarity	NPC96312
0.8065	Intermediate Similarity	NPC476710
0.8065	Intermediate Similarity	NPC474734
0.8065	Intermediate Similarity	NPC476711
0.8065	Intermediate Similarity	NPC40632
0.8065	Intermediate Similarity	NPC328374
0.8065	Intermediate Similarity	NPC173686
0.8065	Intermediate Similarity	NPC16081
0.8065	Intermediate Similarity	NPC251236
0.8062	Intermediate Similarity	NPC217901
0.8062	Intermediate Similarity	NPC250556
0.8062	Intermediate Similarity	NPC87662

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 NPC476851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	1855
0.2-0.3	3842
0.3-0.4	2081
0.4-0.5	626
0.5-0.6	290
0.6-0.7	141
0.7-0.8	70
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8154	Intermediate Similarity	NPD7319	Approved
0.8062	Intermediate Similarity	NPD7507	Approved
0.8047	Intermediate Similarity	NPD8328	Phase 3
0.8	Intermediate Similarity	NPD8293	Discontinued
0.7969	Intermediate Similarity	NPD6370	Approved
0.7939	Intermediate Similarity	NPD7736	Approved
0.7934	Intermediate Similarity	NPD6686	Approved
0.7846	Intermediate Similarity	NPD7492	Approved
0.7812	Intermediate Similarity	NPD6054	Approved
0.7812	Intermediate Similarity	NPD6059	Approved
0.7787	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD6616	Approved
0.7727	Intermediate Similarity	NPD7078	Approved
0.7661	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD7327	Approved
0.7656	Intermediate Similarity	NPD7328	Approved
0.7615	Intermediate Similarity	NPD6015	Approved
0.7615	Intermediate Similarity	NPD6016	Approved
0.7597	Intermediate Similarity	NPD7516	Approved
0.7581	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7115	Discovery
0.7557	Intermediate Similarity	NPD5988	Approved
0.7538	Intermediate Similarity	NPD6319	Approved
0.7481	Intermediate Similarity	NPD8517	Approved
0.7481	Intermediate Similarity	NPD8515	Approved
0.7481	Intermediate Similarity	NPD8513	Phase 3
0.7481	Intermediate Similarity	NPD8516	Approved
0.744	Intermediate Similarity	NPD6372	Approved
0.744	Intermediate Similarity	NPD6373	Approved
0.7419	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8377	Approved
0.7405	Intermediate Similarity	NPD8294	Approved
0.7402	Intermediate Similarity	NPD8297	Approved
0.7402	Intermediate Similarity	NPD6882	Approved
0.736	Intermediate Similarity	NPD7320	Approved
0.7348	Intermediate Similarity	NPD8378	Approved
0.7348	Intermediate Similarity	NPD8033	Approved
0.7348	Intermediate Similarity	NPD8380	Approved
0.7348	Intermediate Similarity	NPD8335	Approved
0.7348	Intermediate Similarity	NPD8379	Approved
0.7348	Intermediate Similarity	NPD8296	Approved
0.7339	Intermediate Similarity	NPD6402	Approved
0.7339	Intermediate Similarity	NPD5739	Approved
0.7339	Intermediate Similarity	NPD6675	Approved
0.7339	Intermediate Similarity	NPD7128	Approved
0.7323	Intermediate Similarity	NPD6650	Approved
0.7323	Intermediate Similarity	NPD6649	Approved
0.7308	Intermediate Similarity	NPD6009	Approved
0.7279	Intermediate Similarity	NPD6033	Approved
0.7273	Intermediate Similarity	NPD4225	Approved
0.7222	Intermediate Similarity	NPD6881	Approved
0.7222	Intermediate Similarity	NPD6899	Approved
0.7218	Intermediate Similarity	NPD6921	Approved
0.7213	Intermediate Similarity	NPD7639	Approved
0.7213	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD6008	Approved
0.7165	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7131	Intermediate Similarity	NPD7638	Approved
0.7111	Intermediate Similarity	NPD7604	Phase 2
0.7109	Intermediate Similarity	NPD7290	Approved
0.7109	Intermediate Similarity	NPD6883	Approved
0.7109	Intermediate Similarity	NPD7102	Approved
0.7077	Intermediate Similarity	NPD8133	Approved
0.7077	Intermediate Similarity	NPD4632	Approved
0.7054	Intermediate Similarity	NPD6847	Approved
0.7054	Intermediate Similarity	NPD6869	Approved
0.7054	Intermediate Similarity	NPD6617	Approved
0.7054	Intermediate Similarity	NPD8130	Phase 1
0.7031	Intermediate Similarity	NPD6014	Approved
0.7031	Intermediate Similarity	NPD6013	Approved
0.7031	Intermediate Similarity	NPD6012	Approved
0.6963	Remote Similarity	NPD7503	Approved
0.6963	Remote Similarity	NPD5983	Phase 2
0.6957	Remote Similarity	NPD8074	Phase 3
0.6953	Remote Similarity	NPD6011	Approved
0.6923	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6336	Discontinued
0.6879	Remote Similarity	NPD7260	Phase 2
0.6875	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5696	Approved
0.6846	Remote Similarity	NPD4634	Approved
0.6846	Remote Similarity	NPD6371	Approved
0.6833	Remote Similarity	NPD46	Approved
0.6833	Remote Similarity	NPD6698	Approved
0.6831	Remote Similarity	NPD6845	Suspended
0.6825	Remote Similarity	NPD5211	Phase 2
0.6774	Remote Similarity	NPD4755	Approved
0.6774	Remote Similarity	NPD6084	Phase 2
0.6774	Remote Similarity	NPD6083	Phase 2
0.6759	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5344	Discontinued
0.6739	Remote Similarity	NPD6067	Discontinued
0.6719	Remote Similarity	NPD5141	Approved
0.6716	Remote Similarity	NPD6274	Approved
0.6693	Remote Similarity	NPD7632	Discontinued
0.6691	Remote Similarity	NPD7100	Approved
0.6691	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.664	Remote Similarity	NPD7902	Approved
0.6618	Remote Similarity	NPD6335	Approved
0.6617	Remote Similarity	NPD6053	Discontinued
0.6613	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6909	Approved
0.6594	Remote Similarity	NPD6908	Approved
0.6594	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5956	Approved
0.6566	Remote Similarity	NPD7799	Discontinued
0.6562	Remote Similarity	NPD5224	Approved
0.6562	Remote Similarity	NPD4633	Approved
0.6562	Remote Similarity	NPD5225	Approved
0.6562	Remote Similarity	NPD5226	Approved
0.656	Remote Similarity	NPD4697	Phase 3
0.6544	Remote Similarity	NPD6317	Approved
0.6538	Remote Similarity	NPD4768	Approved
0.6538	Remote Similarity	NPD4767	Approved
0.6535	Remote Similarity	NPD6648	Approved
0.6532	Remote Similarity	NPD7748	Approved
0.6512	Remote Similarity	NPD5174	Approved
0.6512	Remote Similarity	NPD5175	Approved
0.6504	Remote Similarity	NPD7515	Phase 2
0.65	Remote Similarity	NPD7642	Approved
0.6496	Remote Similarity	NPD6314	Approved
0.6496	Remote Similarity	NPD6313	Approved
0.6484	Remote Similarity	NPD5223	Approved
0.6484	Remote Similarity	NPD1700	Approved
0.648	Remote Similarity	NPD5695	Phase 3
0.648	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5328	Approved
0.6471	Remote Similarity	NPD6868	Approved
0.6463	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5778	Approved
0.6452	Remote Similarity	NPD5779	Approved
0.6452	Remote Similarity	NPD6399	Phase 3
0.6439	Remote Similarity	NPD4729	Approved
0.6439	Remote Similarity	NPD4730	Approved
0.6429	Remote Similarity	NPD5222	Approved
0.6429	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5221	Approved
0.6429	Remote Similarity	NPD8080	Discontinued
0.64	Remote Similarity	NPD7900	Approved
0.64	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5737	Approved
0.6393	Remote Similarity	NPD6672	Approved
0.6385	Remote Similarity	NPD4754	Approved
0.6383	Remote Similarity	NPD7829	Approved
0.6383	Remote Similarity	NPD7830	Approved
0.6378	Remote Similarity	NPD5173	Approved
0.6376	Remote Similarity	NPD6334	Approved
0.6376	Remote Similarity	NPD6333	Approved
0.6371	Remote Similarity	NPD6411	Approved
0.6371	Remote Similarity	NPD7983	Approved
0.6371	Remote Similarity	NPD5693	Phase 1
0.6371	Remote Similarity	NPD6079	Approved
0.637	Remote Similarity	NPD8338	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6349	Remote Similarity	NPD4629	Approved
0.6349	Remote Similarity	NPD5210	Approved
0.6345	Remote Similarity	NPD6914	Discontinued
0.6343	Remote Similarity	NPD5249	Phase 3
0.6343	Remote Similarity	NPD5248	Approved
0.6343	Remote Similarity	NPD5247	Approved
0.6343	Remote Similarity	NPD5251	Approved
0.6343	Remote Similarity	NPD5250	Approved
0.6336	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD8337	Approved
0.6319	Remote Similarity	NPD8336	Approved
0.6316	Remote Similarity	NPD5128	Approved
0.6311	Remote Similarity	NPD3573	Approved
0.6303	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD8415	Approved
0.6281	Remote Similarity	NPD1694	Approved
0.6241	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD8444	Approved
0.621	Remote Similarity	NPD6904	Approved
0.621	Remote Similarity	NPD6673	Approved
0.621	Remote Similarity	NPD6080	Approved
0.621	Remote Similarity	NPD6101	Approved
0.621	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.621	Remote Similarity	NPD4753	Phase 2
0.6207	Remote Similarity	NPD8407	Phase 2
0.6198	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4202	Approved
0.6181	Remote Similarity	NPD8451	Approved
0.6176	Remote Similarity	NPD5217	Approved
0.6176	Remote Similarity	NPD5215	Approved
0.6176	Remote Similarity	NPD5216	Approved
0.6172	Remote Similarity	NPD7839	Suspended
0.616	Remote Similarity	NPD5785	Approved
0.616	Remote Similarity	NPD7838	Discovery
0.6154	Remote Similarity	NPD7625	Phase 1

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