NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	492.14
Volume:	482.877
LogP:	4.229
LogD:	2.735
LogS:	-3.826
# Rotatable Bonds:	4
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.187
Synthetic Accessibility Score:	4.015
Fsp3:	0.222
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:	-6.076
MDCK Permeability:	7.73506508267019e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.95
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	98.34074401855469%
Volume Distribution (VD):	0.48
Pgp-substrate:	2.6822497844696045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.683
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.705
CYP2C9-substrate:	0.724
CYP2D6-inhibitor:	0.769
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.038

ADMET: Excretion

Clearance (CL):	4.809
Half-life (T1/2):	0.638

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.021
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.717
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.923
Carcinogencity:	0.688
Eye Corrosion:	0.003
Eye Irritation:	0.909
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC187934

Natural Product ID:	NPC187934
*Common Name:**	10-Epi-Uveoside
IUPAC Name:	[(2R,3S,4S,5S,6R)-6-[(9S)-4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl]-3,4,5-trihydroxyoxan-2-yl] benzoate
Synonyms:	10-Epi-Uveoside
Standard InCHIKey:	HJWBFDYPJOWKRB-UQLHSBTDSA-N
Standard InCHI:	InChI=1S/C27H24O9/c1-12-10-15-18(14-8-5-9-16(28)19(14)21(30)20(15)17(29)11-12)25-23(32)22(31)24(33)27(35-25)36-26(34)13-6-3-2-4-7-13/h2-11,18,22-25,27-29,31-33H,1H3/t18-,22-,23-,24-,25+,27+/m0/s1
SMILES:	CC1=CC2=C(C(=C1)O)C(=O)C3=C([C@@H]2[C@@H]4[C@H]([C@@H]([C@@H]([C@H](O4)OC(=O)C5=CC=CC=C5)O)O)O)C=CC=C3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49799757
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO25595	Picramnia antidesma	Species	Picramniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25595	Picramnia antidesma	Species	Picramniaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2400	nM	PMID[19299148]

☑ 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 NPC187934 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	353
0.1-0.2	1369
0.2-0.3	2869
0.3-0.4	6218
0.4-0.5	10097
0.5-0.6	7166
0.6-0.7	6457
0.7-0.8	7368
0.8-0.85	635
0.85-0.9	127
0.9-0.95	29
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC97637
0.9673	High Similarity	NPC283480
0.9673	High Similarity	NPC148323
0.9608	High Similarity	NPC192219
0.9608	High Similarity	NPC174599
0.9608	High Similarity	NPC82190
0.9548	High Similarity	NPC53139
0.9542	High Similarity	NPC209393
0.9542	High Similarity	NPC205172
0.9484	High Similarity	NPC208651
0.9484	High Similarity	NPC206641
0.9477	High Similarity	NPC474533
0.9477	High Similarity	NPC474534
0.9371	High Similarity	NPC478022
0.9371	High Similarity	NPC478020
0.9355	High Similarity	NPC3449
0.929	High Similarity	NPC474622
0.929	High Similarity	NPC474621
0.9207	High Similarity	NPC470667
0.9146	High Similarity	NPC85368
0.9146	High Similarity	NPC203751
0.9141	High Similarity	NPC478021
0.913	High Similarity	NPC178281
0.9091	High Similarity	NPC186800
0.9085	High Similarity	NPC294501
0.9085	High Similarity	NPC183441
0.9036	High Similarity	NPC92403
0.9036	High Similarity	NPC66820
0.9036	High Similarity	NPC289876
0.9036	High Similarity	NPC170018
0.9036	High Similarity	NPC102053
0.9036	High Similarity	NPC76112
0.902	High Similarity	NPC170055
0.9006	High Similarity	NPC212099
0.9006	High Similarity	NPC146837
0.9006	High Similarity	NPC278329
0.9006	High Similarity	NPC101116
0.8954	High Similarity	NPC84568
0.8954	High Similarity	NPC48130
0.8954	High Similarity	NPC300684
0.8954	High Similarity	NPC218866
0.8935	High Similarity	NPC473631
0.8935	High Similarity	NPC293227
0.8935	High Similarity	NPC475662
0.8935	High Similarity	NPC473717
0.8929	High Similarity	NPC277710
0.8929	High Similarity	NPC58538
0.8929	High Similarity	NPC114257
0.8929	High Similarity	NPC153578
0.8929	High Similarity	NPC299149
0.8922	High Similarity	NPC176246
0.8909	High Similarity	NPC298778
0.8896	High Similarity	NPC478026
0.8889	High Similarity	NPC216752
0.8889	High Similarity	NPC105591
0.8876	High Similarity	NPC477860
0.8876	High Similarity	NPC197357
0.8876	High Similarity	NPC85316
0.8876	High Similarity	NPC475161
0.8862	High Similarity	NPC68381
0.8862	High Similarity	NPC474345
0.8848	High Similarity	NPC175477
0.8839	High Similarity	NPC285122
0.8837	High Similarity	NPC205721
0.883	High Similarity	NPC221140
0.883	High Similarity	NPC229817
0.883	High Similarity	NPC475352
0.883	High Similarity	NPC475220
0.883	High Similarity	NPC473686
0.881	High Similarity	NPC475246
0.8802	High Similarity	NPC65118
0.8802	High Similarity	NPC199357
0.8802	High Similarity	NPC472054
0.8788	High Similarity	NPC63470
0.8772	High Similarity	NPC224557
0.8772	High Similarity	NPC292706
0.875	High Similarity	NPC472835
0.875	High Similarity	NPC266469
0.875	High Similarity	NPC3718
0.8743	High Similarity	NPC76128
0.8743	High Similarity	NPC271385
0.8743	High Similarity	NPC111536
0.8743	High Similarity	NPC30432
0.8743	High Similarity	NPC5029
0.8727	High Similarity	NPC469419
0.8721	High Similarity	NPC87583
0.8706	High Similarity	NPC72783
0.8704	High Similarity	NPC314795
0.8698	High Similarity	NPC46958
0.8696	High Similarity	NPC478027
0.8683	High Similarity	NPC52598
0.8671	High Similarity	NPC247219
0.8667	High Similarity	NPC99216
0.8667	High Similarity	NPC470735
0.8667	High Similarity	NPC329647
0.8662	High Similarity	NPC119767
0.8655	High Similarity	NPC315221
0.865	High Similarity	NPC208676
0.865	High Similarity	NPC328093
0.865	High Similarity	NPC130489
0.8642	High Similarity	NPC257309
0.8639	High Similarity	NPC70862
0.8639	High Similarity	NPC63105
0.8625	High Similarity	NPC257847
0.8623	High Similarity	NPC222455
0.8623	High Similarity	NPC259905
0.8623	High Similarity	NPC246274
0.8614	High Similarity	NPC178851
0.8613	High Similarity	NPC241847
0.8605	High Similarity	NPC313452
0.8599	High Similarity	NPC147250
0.8598	High Similarity	NPC477627
0.8588	High Similarity	NPC42286
0.8588	High Similarity	NPC475233
0.858	High Similarity	NPC213052
0.8571	High Similarity	NPC182921
0.8571	High Similarity	NPC470580
0.8571	High Similarity	NPC218870
0.8571	High Similarity	NPC76047
0.8571	High Similarity	NPC474824
0.8571	High Similarity	NPC470408
0.8538	High Similarity	NPC47191
0.8529	High Similarity	NPC307754
0.8529	High Similarity	NPC199533
0.8529	High Similarity	NPC19056
0.8529	High Similarity	NPC470454
0.8529	High Similarity	NPC470583
0.8529	High Similarity	NPC223735
0.8528	High Similarity	NPC29552
0.8523	High Similarity	NPC264302
0.8521	High Similarity	NPC13989
0.8521	High Similarity	NPC315619
0.8521	High Similarity	NPC270027
0.8519	High Similarity	NPC66029
0.85	High Similarity	NPC205766
0.8494	Intermediate Similarity	NPC17432
0.8491	Intermediate Similarity	NPC94781
0.8488	Intermediate Similarity	NPC84494
0.8488	Intermediate Similarity	NPC212290
0.8488	Intermediate Similarity	NPC245059
0.8471	Intermediate Similarity	NPC98776
0.8471	Intermediate Similarity	NPC103910
0.8466	Intermediate Similarity	NPC471787
0.8466	Intermediate Similarity	NPC474861
0.8466	Intermediate Similarity	NPC314672
0.8462	Intermediate Similarity	NPC470272
0.8457	Intermediate Similarity	NPC230439
0.8457	Intermediate Similarity	NPC185103
0.8457	Intermediate Similarity	NPC472128
0.8457	Intermediate Similarity	NPC92153
0.8457	Intermediate Similarity	NPC279281
0.8457	Intermediate Similarity	NPC472127
0.8457	Intermediate Similarity	NPC299761
0.8452	Intermediate Similarity	NPC470271
0.8452	Intermediate Similarity	NPC298847
0.8452	Intermediate Similarity	NPC311389
0.8448	Intermediate Similarity	NPC231254
0.8439	Intermediate Similarity	NPC164047
0.8439	Intermediate Similarity	NPC470452
0.8439	Intermediate Similarity	NPC470448
0.8439	Intermediate Similarity	NPC470453
0.8438	Intermediate Similarity	NPC280753
0.8438	Intermediate Similarity	NPC44378
0.8434	Intermediate Similarity	NPC14030
0.8434	Intermediate Similarity	NPC291957
0.8434	Intermediate Similarity	NPC472876
0.843	Intermediate Similarity	NPC469418
0.843	Intermediate Similarity	NPC115447
0.843	Intermediate Similarity	NPC470581
0.843	Intermediate Similarity	NPC266513
0.843	Intermediate Similarity	NPC470582
0.8428	Intermediate Similarity	NPC471734
0.8421	Intermediate Similarity	NPC146803
0.8415	Intermediate Similarity	NPC317580
0.8415	Intermediate Similarity	NPC177742
0.8412	Intermediate Similarity	NPC47140
0.8412	Intermediate Similarity	NPC478002
0.8412	Intermediate Similarity	NPC67134
0.8408	Intermediate Similarity	NPC100242
0.8405	Intermediate Similarity	NPC474501
0.8393	Intermediate Similarity	NPC469458
0.8393	Intermediate Similarity	NPC88176
0.8393	Intermediate Similarity	NPC175793
0.8393	Intermediate Similarity	NPC469396
0.8393	Intermediate Similarity	NPC477835
0.8393	Intermediate Similarity	NPC149002
0.8391	Intermediate Similarity	NPC478001
0.8385	Intermediate Similarity	NPC315520
0.8385	Intermediate Similarity	NPC477914
0.8385	Intermediate Similarity	NPC475407
0.8383	Intermediate Similarity	NPC470898
0.8382	Intermediate Similarity	NPC187441
0.8382	Intermediate Similarity	NPC283980
0.8373	Intermediate Similarity	NPC195685
0.8373	Intermediate Similarity	NPC210961
0.8373	Intermediate Similarity	NPC477629
0.8373	Intermediate Similarity	NPC97812
0.8373	Intermediate Similarity	NPC472994
0.8373	Intermediate Similarity	NPC477628
0.8373	Intermediate Similarity	NPC270675

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 NPC187934 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	854
0.2-0.3	1569
0.3-0.4	2605
0.4-0.5	2153
0.5-0.6	1138
0.6-0.7	371
0.7-0.8	129
0.8-0.85	25
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9036	High Similarity	NPD8313	Approved
0.9036	High Similarity	NPD8312	Approved
0.8779	High Similarity	NPD7879	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD8150	Discontinued
0.8362	Intermediate Similarity	NPD6534	Approved
0.8362	Intermediate Similarity	NPD6535	Approved
0.8352	Intermediate Similarity	NPD8319	Approved
0.8352	Intermediate Similarity	NPD8320	Phase 1
0.8343	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD6213	Phase 3
0.8305	Intermediate Similarity	NPD6212	Phase 3
0.8305	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.8297	Intermediate Similarity	NPD7435	Discontinued
0.8256	Intermediate Similarity	NPD6559	Discontinued
0.8232	Intermediate Similarity	NPD6776	Approved
0.8232	Intermediate Similarity	NPD6782	Approved
0.8232	Intermediate Similarity	NPD6780	Approved
0.8232	Intermediate Similarity	NPD6781	Approved
0.8232	Intermediate Similarity	NPD6777	Approved
0.8232	Intermediate Similarity	NPD6779	Approved
0.8232	Intermediate Similarity	NPD6778	Approved
0.8222	Intermediate Similarity	NPD7700	Phase 2
0.8222	Intermediate Similarity	NPD7699	Phase 2
0.8193	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6959	Discontinued
0.8098	Intermediate Similarity	NPD7458	Discontinued
0.8081	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD8151	Discontinued
0.807	Intermediate Similarity	NPD7473	Discontinued
0.8054	Intermediate Similarity	NPD7870	Phase 2
0.8054	Intermediate Similarity	NPD7871	Phase 2
0.8049	Intermediate Similarity	NPD4380	Phase 2
0.8035	Intermediate Similarity	NPD7074	Phase 3
0.8032	Intermediate Similarity	NPD7874	Approved
0.8032	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD7696	Phase 3
0.8	Intermediate Similarity	NPD7697	Approved
0.8	Intermediate Similarity	NPD7698	Approved
0.7988	Intermediate Similarity	NPD3226	Approved
0.7977	Intermediate Similarity	NPD7054	Approved
0.7977	Intermediate Similarity	NPD5844	Phase 1
0.7946	Intermediate Similarity	NPD6823	Phase 2
0.7931	Intermediate Similarity	NPD7472	Approved
0.7926	Intermediate Similarity	NPD7701	Phase 2
0.7911	Intermediate Similarity	NPD5408	Approved
0.7911	Intermediate Similarity	NPD5404	Approved
0.7911	Intermediate Similarity	NPD5405	Approved
0.7911	Intermediate Similarity	NPD5406	Approved
0.7904	Intermediate Similarity	NPD7819	Suspended
0.7904	Intermediate Similarity	NPD8455	Phase 2
0.7901	Intermediate Similarity	NPD7390	Discontinued
0.7895	Intermediate Similarity	NPD7801	Approved
0.7886	Intermediate Similarity	NPD6797	Phase 2
0.7879	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7075	Discontinued
0.7841	Intermediate Similarity	NPD7251	Discontinued
0.7816	Intermediate Similarity	NPD3818	Discontinued
0.7803	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6166	Phase 2
0.7803	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7783	Phase 2
0.7801	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7808	Phase 3
0.7784	Intermediate Similarity	NPD7411	Suspended
0.7751	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2346	Discontinued
0.7744	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7228	Approved
0.7706	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7266	Discontinued
0.7636	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6801	Discontinued
0.7607	Intermediate Similarity	NPD4628	Phase 3
0.7607	Intermediate Similarity	NPD7003	Approved
0.7584	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5402	Approved
0.7542	Intermediate Similarity	NPD7685	Pre-registration
0.753	Intermediate Similarity	NPD2532	Approved
0.753	Intermediate Similarity	NPD2533	Approved
0.753	Intermediate Similarity	NPD2534	Approved
0.7529	Intermediate Similarity	NPD1934	Approved
0.7529	Intermediate Similarity	NPD37	Approved
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.7514	Intermediate Similarity	NPD7799	Discontinued
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7486	Intermediate Similarity	NPD3787	Discontinued
0.7484	Intermediate Similarity	NPD1470	Approved
0.7469	Intermediate Similarity	NPD2935	Discontinued
0.7451	Intermediate Similarity	NPD1201	Approved
0.744	Intermediate Similarity	NPD5403	Approved
0.7429	Intermediate Similarity	NPD7199	Phase 2
0.7425	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7177	Discontinued
0.7412	Intermediate Similarity	NPD6599	Discontinued
0.7394	Intermediate Similarity	NPD8166	Discontinued
0.7378	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5494	Approved
0.7365	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3764	Approved
0.7356	Intermediate Similarity	NPD3749	Approved
0.7349	Intermediate Similarity	NPD6190	Approved
0.7348	Intermediate Similarity	NPD7240	Approved
0.7341	Intermediate Similarity	NPD3817	Phase 2
0.7337	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5401	Approved
0.7321	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6273	Approved
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7268	Intermediate Similarity	NPD8059	Phase 3
0.7268	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6799	Approved
0.7247	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8434	Phase 2
0.7236	Intermediate Similarity	NPD7930	Approved
0.7229	Intermediate Similarity	NPD6674	Discontinued
0.7215	Intermediate Similarity	NPD2798	Approved
0.7212	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2799	Discontinued
0.7195	Intermediate Similarity	NPD1510	Phase 2
0.7188	Intermediate Similarity	NPD7008	Discontinued
0.7186	Intermediate Similarity	NPD3750	Approved
0.7184	Intermediate Similarity	NPD2801	Approved
0.7184	Intermediate Similarity	NPD1465	Phase 2
0.7178	Intermediate Similarity	NPD1607	Approved
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7135	Intermediate Similarity	NPD8285	Discontinued
0.7102	Intermediate Similarity	NPD3882	Suspended
0.7101	Intermediate Similarity	NPD3300	Phase 2
0.7097	Intermediate Similarity	NPD5126	Approved
0.7097	Intermediate Similarity	NPD5125	Phase 3
0.7095	Intermediate Similarity	NPD5711	Approved
0.7095	Intermediate Similarity	NPD5710	Approved
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1511	Approved
0.7056	Intermediate Similarity	NPD7584	Approved
0.7055	Intermediate Similarity	NPD1240	Approved
0.7048	Intermediate Similarity	NPD2438	Suspended
0.7048	Intermediate Similarity	NPD2796	Approved
0.7039	Intermediate Similarity	NPD8127	Discontinued
0.7031	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1933	Approved
0.7012	Intermediate Similarity	NPD230	Phase 1
0.701	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7999	Approved
0.7	Intermediate Similarity	NPD7236	Approved
0.6995	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7239	Suspended
0.699	Remote Similarity	NPD7680	Approved
0.6988	Remote Similarity	NPD7033	Discontinued
0.6984	Remote Similarity	NPD8361	Approved
0.6984	Remote Similarity	NPD8360	Approved
0.6977	Remote Similarity	NPD1512	Approved
0.6973	Remote Similarity	NPD8368	Discontinued
0.6968	Remote Similarity	NPD9545	Approved
0.6959	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4060	Phase 1
0.6951	Remote Similarity	NPD943	Approved
0.6951	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD9493	Approved
0.6946	Remote Similarity	NPD6099	Approved
0.6946	Remote Similarity	NPD6100	Approved
0.6928	Remote Similarity	NPD7097	Phase 1
0.6914	Remote Similarity	NPD6832	Phase 2
0.6905	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1653	Approved
0.6895	Remote Similarity	NPD8435	Approved
0.6886	Remote Similarity	NPD3748	Approved
0.6875	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1283	Approved
0.6862	Remote Similarity	NPD8407	Phase 2
0.6856	Remote Similarity	NPD8485	Approved
0.6855	Remote Similarity	NPD1608	Approved
0.685	Remote Similarity	NPD7585	Approved
0.6848	Remote Similarity	NPD2979	Phase 3
0.6832	Remote Similarity	NPD1164	Approved
0.6832	Remote Similarity	NPD1203	Approved
0.6829	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3268	Approved
0.6829	Remote Similarity	NPD6798	Discontinued
0.6828	Remote Similarity	NPD5953	Discontinued
0.6824	Remote Similarity	NPD5698	Clinical (unspecified phase)

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