NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	772.29
Volume:	734.2
LogP:	3.11
LogD:	1.784
LogS:	-5.074
# Rotatable Bonds:	14
TPSA:	198.63
# H-Bond Aceptor:	16
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.26
Synthetic Accessibility Score:	6.298
Fsp3:	0.744
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:	-5.366
MDCK Permeability:	0.00010705896420404315
Pgp-inhibitor:	0.999
Pgp-substrate:	0.059
Human Intestinal Absorption (HIA):	0.164
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.656

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.701
Plasma Protein Binding (PPB):	74.60919952392578%
Volume Distribution (VD):	1.568
Pgp-substrate:	17.14982795715332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.897
CYP2C19-inhibitor:	0.161
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.114
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	2.239
Half-life (T1/2):	0.625

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.818
Drug-inuced Liver Injury (DILI):	0.798
AMES Toxicity:	0.955
Rat Oral Acute Toxicity:	0.998
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.457
Carcinogencity:	0.956
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC477824

Natural Product ID:	NPC477824
*Common Name:**	[(1R,5S,8R,9R,10R,11S,12S,13S,14S,15S,20R)-12,13-diacetyloxy-8-[(R)-acetyloxy(furan-3-yl)methyl]-9-(2-methoxy-2-oxoethyl)-3,8,14-trimethyl-17-oxo-2,4,18,22-tetraoxaheptacyclo[12.6.1.13,10.01,12.05,10.05,20.015,20]docosan-11-yl] 2-methylpropanoate
IUPAC Name:	[(1R,5S,8R,9R,10R,11S,12S,13S,14S,15S,20R)-12,13-diacetyloxy-8-[(R)-acetyloxy(furan-3-yl)methyl]-9-(2-methoxy-2-oxoethyl)-3,8,14-trimethyl-17-oxo-2,4,18,22-tetraoxaheptacyclo[12.6.1.13,10.01,12.05,10.05,20.015,20]docosan-11-yl] 2-methylpropanoate
Synonyms:
Standard InCHIKey:	PLNWCPKDDIKITN-GDTNESJVSA-N
Standard InCHI:	InChI=1S/C39H48O16/c1-19(2)29(45)51-31-38-25(15-26(43)46-9)32(6,28(49-20(3)40)23-10-13-47-16-23)11-12-36(38)35-18-48-27(44)14-24(35)33(7)17-37(35,54-34(8,53-36)55-38)39(31,52-22(5)42)30(33)50-21(4)41/h10,13,16,19,24-25,28,30-31H,11-12,14-15,17-18H2,1-9H3/t24-,25+,28-,30-,31-,32+,33-,34?,35-,36-,37+,38+,39-/m0/s1
SMILES:	CC(C)C(=O)O[C@H]1[C@]23[C@@H]([C@](CC[C@]24[C@]56COC(=O)C[C@H]5[C@@]7(C[C@@]6([C@@]1([C@H]7OC(=O)C)OC(=O)C)OC(O4)(O3)C)C)(C)[C@H](C8=COC=C8)OC(=O)C)CC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16104849
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO7664	Pseudocedrela kotschyi	Species	Meliaceae	Eukaryota	roots	n.a.	n.a.	PMID[17253841]
NPO7664	Pseudocedrela kotschyi	Species	Meliaceae	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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	90	ug/ml	PMID[17253841]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	5	ug/ml	PMID[17253841]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	30	ug/ml	PMID[17253841]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	11.6	ug/ml	PMID[17253841]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	30	ug/ml	PMID[17253841]

☑ 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 NPC477824 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	523
0.1-0.2	1875
0.2-0.3	3844
0.3-0.4	7515
0.4-0.5	11090
0.5-0.6	11498
0.6-0.7	5513
0.7-0.8	706
0.8-0.85	109
0.85-0.9	21
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9755	High Similarity	NPC470181
0.9059	High Similarity	NPC470938
0.9036	High Similarity	NPC327922
0.8909	High Similarity	NPC472139
0.8889	High Similarity	NPC476262
0.8824	High Similarity	NPC94763
0.8765	High Similarity	NPC476201
0.8713	High Similarity	NPC236004
0.8683	High Similarity	NPC165218
0.8683	High Similarity	NPC472669
0.8642	High Similarity	NPC476122
0.8623	High Similarity	NPC472668
0.8623	High Similarity	NPC471167
0.8623	High Similarity	NPC471166
0.858	High Similarity	NPC472141
0.858	High Similarity	NPC93172
0.858	High Similarity	NPC97574
0.8571	High Similarity	NPC471168
0.8555	High Similarity	NPC469633
0.8537	High Similarity	NPC84063
0.8529	High Similarity	NPC476224
0.8521	High Similarity	NPC470182
0.8512	High Similarity	NPC200782
0.8506	High Similarity	NPC478177
0.8497	Intermediate Similarity	NPC469576
0.8494	Intermediate Similarity	NPC471169
0.8494	Intermediate Similarity	NPC175964
0.8475	Intermediate Similarity	NPC242068
0.8475	Intermediate Similarity	NPC247563
0.8475	Intermediate Similarity	NPC105395
0.8471	Intermediate Similarity	NPC478178
0.8462	Intermediate Similarity	NPC469846
0.8443	Intermediate Similarity	NPC195131
0.8443	Intermediate Similarity	NPC167142
0.8439	Intermediate Similarity	NPC469848
0.8434	Intermediate Similarity	NPC471175
0.843	Intermediate Similarity	NPC82602
0.8424	Intermediate Similarity	NPC322546
0.8424	Intermediate Similarity	NPC308205
0.8421	Intermediate Similarity	NPC100333
0.8421	Intermediate Similarity	NPC472764
0.8402	Intermediate Similarity	NPC82851
0.8393	Intermediate Similarity	NPC475226
0.8393	Intermediate Similarity	NPC474932
0.8391	Intermediate Similarity	NPC471437
0.8383	Intermediate Similarity	NPC204663
0.8382	Intermediate Similarity	NPC159232
0.8382	Intermediate Similarity	NPC285227
0.8373	Intermediate Similarity	NPC282445
0.8372	Intermediate Similarity	NPC472765
0.8372	Intermediate Similarity	NPC472766
0.8372	Intermediate Similarity	NPC472673
0.8364	Intermediate Similarity	NPC18135
0.8353	Intermediate Similarity	NPC476197
0.8353	Intermediate Similarity	NPC419
0.8324	Intermediate Similarity	NPC472650
0.8324	Intermediate Similarity	NPC472659
0.8313	Intermediate Similarity	NPC182427
0.8313	Intermediate Similarity	NPC29695
0.8303	Intermediate Similarity	NPC196864
0.8303	Intermediate Similarity	NPC477404
0.8294	Intermediate Similarity	NPC211777
0.8294	Intermediate Similarity	NPC117986
0.8294	Intermediate Similarity	NPC207978
0.8294	Intermediate Similarity	NPC6326
0.8284	Intermediate Similarity	NPC473473
0.8284	Intermediate Similarity	NPC307383
0.8284	Intermediate Similarity	NPC475295
0.8276	Intermediate Similarity	NPC169299
0.8276	Intermediate Similarity	NPC160818
0.8266	Intermediate Similarity	NPC242334
0.8256	Intermediate Similarity	NPC214600
0.8246	Intermediate Similarity	NPC198047
0.8242	Intermediate Similarity	NPC470791
0.8242	Intermediate Similarity	NPC470790
0.8235	Intermediate Similarity	NPC472653
0.8232	Intermediate Similarity	NPC470941
0.8225	Intermediate Similarity	NPC470119
0.8225	Intermediate Similarity	NPC214495
0.8225	Intermediate Similarity	NPC299038
0.8225	Intermediate Similarity	NPC472283
0.8225	Intermediate Similarity	NPC469847
0.8225	Intermediate Similarity	NPC286722
0.8225	Intermediate Similarity	NPC249021
0.8214	Intermediate Similarity	NPC469850
0.8208	Intermediate Similarity	NPC478179
0.8204	Intermediate Similarity	NPC469503
0.8198	Intermediate Similarity	NPC271657
0.8198	Intermediate Similarity	NPC259943
0.8198	Intermediate Similarity	NPC469849
0.8193	Intermediate Similarity	NPC159927
0.8193	Intermediate Similarity	NPC469335
0.8193	Intermediate Similarity	NPC156189
0.8187	Intermediate Similarity	NPC290400
0.8187	Intermediate Similarity	NPC472771
0.8187	Intermediate Similarity	NPC472767
0.8187	Intermediate Similarity	NPC470792
0.8187	Intermediate Similarity	NPC18347
0.8187	Intermediate Similarity	NPC470939
0.8187	Intermediate Similarity	NPC149896
0.8187	Intermediate Similarity	NPC96443
0.8187	Intermediate Similarity	NPC5741
0.8182	Intermediate Similarity	NPC471632
0.8176	Intermediate Similarity	NPC475967
0.8166	Intermediate Similarity	NPC126723
0.8166	Intermediate Similarity	NPC107646
0.8166	Intermediate Similarity	NPC209364
0.8161	Intermediate Similarity	NPC271235
0.8161	Intermediate Similarity	NPC160651
0.815	Intermediate Similarity	NPC472670
0.815	Intermediate Similarity	NPC470875
0.815	Intermediate Similarity	NPC149945
0.815	Intermediate Similarity	NPC307781
0.8144	Intermediate Similarity	NPC471000
0.814	Intermediate Similarity	NPC302369
0.814	Intermediate Similarity	NPC469338
0.814	Intermediate Similarity	NPC472773
0.814	Intermediate Similarity	NPC477405
0.814	Intermediate Similarity	NPC39986
0.814	Intermediate Similarity	NPC292389
0.814	Intermediate Similarity	NPC134254
0.8136	Intermediate Similarity	NPC262386
0.8133	Intermediate Similarity	NPC471001
0.8129	Intermediate Similarity	NPC475381
0.8129	Intermediate Similarity	NPC191828
0.8129	Intermediate Similarity	NPC305016
0.8121	Intermediate Similarity	NPC221809
0.8121	Intermediate Similarity	NPC255414
0.8118	Intermediate Similarity	NPC475066
0.8103	Intermediate Similarity	NPC472774
0.8103	Intermediate Similarity	NPC472775
0.8103	Intermediate Similarity	NPC173516
0.8095	Intermediate Similarity	NPC472672
0.8092	Intermediate Similarity	NPC276551
0.8092	Intermediate Similarity	NPC470940
0.8092	Intermediate Similarity	NPC61967
0.8081	Intermediate Similarity	NPC197596
0.807	Intermediate Similarity	NPC472671
0.807	Intermediate Similarity	NPC262872
0.8068	Intermediate Similarity	NPC475641
0.8068	Intermediate Similarity	NPC475237
0.8057	Intermediate Similarity	NPC471397
0.8057	Intermediate Similarity	NPC472652
0.8047	Intermediate Similarity	NPC302054
0.8047	Intermediate Similarity	NPC253201
0.8047	Intermediate Similarity	NPC30222
0.8036	Intermediate Similarity	NPC116717
0.8035	Intermediate Similarity	NPC234660
0.8035	Intermediate Similarity	NPC51568
0.8024	Intermediate Similarity	NPC69647
0.8024	Intermediate Similarity	NPC125182
0.8024	Intermediate Similarity	NPC472654
0.8023	Intermediate Similarity	NPC335761
0.8023	Intermediate Similarity	NPC470789
0.8012	Intermediate Similarity	NPC472778
0.8012	Intermediate Similarity	NPC472777
0.8012	Intermediate Similarity	NPC472776
0.8012	Intermediate Similarity	NPC470118
0.8012	Intermediate Similarity	NPC45101
0.8012	Intermediate Similarity	NPC36655
0.8012	Intermediate Similarity	NPC261597
0.8012	Intermediate Similarity	NPC472772
0.8	Intermediate Similarity	NPC469336
0.8	Intermediate Similarity	NPC35000
0.8	Intermediate Similarity	NPC44675
0.8	Intermediate Similarity	NPC476850
0.8	Intermediate Similarity	NPC214541
0.8	Intermediate Similarity	NPC472282
0.8	Intermediate Similarity	NPC264943
0.8	Intermediate Similarity	NPC476861
0.8	Intermediate Similarity	NPC472651
0.7989	Intermediate Similarity	NPC476858
0.7989	Intermediate Similarity	NPC62692
0.7989	Intermediate Similarity	NPC27541
0.7989	Intermediate Similarity	NPC476856
0.7989	Intermediate Similarity	NPC126984
0.7989	Intermediate Similarity	NPC476857
0.7989	Intermediate Similarity	NPC276735
0.7988	Intermediate Similarity	NPC223415
0.7988	Intermediate Similarity	NPC268905
0.7977	Intermediate Similarity	NPC188649
0.7977	Intermediate Similarity	NPC69028
0.7977	Intermediate Similarity	NPC329938
0.7977	Intermediate Similarity	NPC5079
0.7976	Intermediate Similarity	NPC476936
0.7965	Intermediate Similarity	NPC237155
0.7953	Intermediate Similarity	NPC60973
0.7952	Intermediate Similarity	NPC470999
0.7941	Intermediate Similarity	NPC237259
0.7941	Intermediate Similarity	NPC178932
0.7941	Intermediate Similarity	NPC98206
0.7941	Intermediate Similarity	NPC57998
0.7941	Intermediate Similarity	NPC34421
0.7931	Intermediate Similarity	NPC663
0.7931	Intermediate Similarity	NPC88841
0.7931	Intermediate Similarity	NPC288602
0.7931	Intermediate Similarity	NPC224394
0.7929	Intermediate Similarity	NPC291150
0.7919	Intermediate Similarity	NPC25255
0.7917	Intermediate Similarity	NPC195325

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 NPC477824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	1191
0.2-0.3	2558
0.3-0.4	2861
0.4-0.5	1509
0.5-0.6	504
0.6-0.7	114
0.7-0.8	5
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
0.8214	Intermediate Similarity	NPD5760	Phase 2
0.8214	Intermediate Similarity	NPD5761	Phase 2
0.7622	Intermediate Similarity	NPD8434	Phase 2
0.7416	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5494	Approved
0.7166	Intermediate Similarity	NPD7685	Pre-registration
0.7166	Intermediate Similarity	NPD6765	Approved
0.7166	Intermediate Similarity	NPD6764	Approved
0.7135	Intermediate Similarity	NPD7799	Discontinued
0.7016	Intermediate Similarity	NPD6784	Approved
0.7016	Intermediate Similarity	NPD6785	Approved
0.6923	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7497	Discontinued
0.6911	Remote Similarity	NPD8313	Approved
0.6911	Remote Similarity	NPD8312	Approved
0.6906	Remote Similarity	NPD7819	Suspended
0.6895	Remote Similarity	NPD6559	Discontinued
0.6865	Remote Similarity	NPD8127	Discontinued
0.6842	Remote Similarity	NPD8404	Phase 2
0.6774	Remote Similarity	NPD7199	Phase 2
0.6737	Remote Similarity	NPD5844	Phase 1
0.6737	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6273	Approved
0.6703	Remote Similarity	NPD7075	Discontinued
0.6703	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7472	Approved
0.6702	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7074	Phase 3
0.6684	Remote Similarity	NPD7228	Approved
0.6684	Remote Similarity	NPD7808	Phase 3
0.6684	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4965	Approved
0.6649	Remote Similarity	NPD7054	Approved
0.6649	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4966	Approved
0.6649	Remote Similarity	NPD4967	Phase 2
0.6648	Remote Similarity	NPD6599	Discontinued
0.6632	Remote Similarity	NPD7240	Approved
0.6632	Remote Similarity	NPD7251	Discontinued
0.6615	Remote Similarity	NPD8407	Phase 2
0.661	Remote Similarity	NPD4628	Phase 3
0.6598	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.658	Remote Similarity	NPD6797	Phase 2
0.6578	Remote Similarity	NPD919	Approved
0.6578	Remote Similarity	NPD6234	Discontinued
0.6576	Remote Similarity	NPD37	Approved
0.6566	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7028	Phase 2
0.6556	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7319	Approved
0.6546	Remote Similarity	NPD8368	Discontinued
0.6545	Remote Similarity	NPD7473	Discontinued
0.6541	Remote Similarity	NPD8455	Phase 2
0.6536	Remote Similarity	NPD7236	Approved
0.6524	Remote Similarity	NPD3749	Approved
0.6522	Remote Similarity	NPD7411	Suspended
0.651	Remote Similarity	NPD3751	Discontinued
0.6508	Remote Similarity	NPD1247	Approved
0.6505	Remote Similarity	NPD7435	Discontinued
0.6505	Remote Similarity	NPD5402	Approved
0.6505	Remote Similarity	NPD3817	Phase 2
0.6505	Remote Similarity	NPD7696	Phase 3
0.6505	Remote Similarity	NPD7697	Approved
0.6505	Remote Similarity	NPD7698	Approved
0.6503	Remote Similarity	NPD7458	Discontinued
0.6495	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6801	Discontinued
0.6477	Remote Similarity	NPD2796	Approved
0.6474	Remote Similarity	NPD6232	Discontinued
0.6474	Remote Similarity	NPD3787	Discontinued
0.6467	Remote Similarity	NPD4380	Phase 2
0.6465	Remote Similarity	NPD8150	Discontinued
0.6452	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7239	Suspended
0.6445	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD7783	Phase 2
0.6444	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1933	Approved
0.6429	Remote Similarity	NPD8151	Discontinued
0.6425	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6959	Discontinued
0.6409	Remote Similarity	NPD6799	Approved
0.6409	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6166	Phase 2
0.6406	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD1934	Approved
0.6398	Remote Similarity	NPD7874	Approved
0.6394	Remote Similarity	NPD7870	Phase 2
0.6394	Remote Similarity	NPD7871	Phase 2
0.6383	Remote Similarity	NPD7768	Phase 2
0.6381	Remote Similarity	NPD7701	Phase 2
0.6374	Remote Similarity	NPD2534	Approved
0.6374	Remote Similarity	NPD2532	Approved
0.6374	Remote Similarity	NPD2533	Approved
0.6369	Remote Similarity	NPD7507	Approved
0.6364	Remote Similarity	NPD1465	Phase 2
0.6359	Remote Similarity	NPD6776	Approved
0.6359	Remote Similarity	NPD6782	Approved
0.6359	Remote Similarity	NPD6777	Approved
0.6359	Remote Similarity	NPD6779	Approved
0.6359	Remote Similarity	NPD6778	Approved
0.6359	Remote Similarity	NPD6781	Approved
0.6359	Remote Similarity	NPD6780	Approved
0.6354	Remote Similarity	NPD3926	Phase 2
0.6348	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6004	Phase 3
0.6348	Remote Similarity	NPD6005	Phase 3
0.6348	Remote Similarity	NPD6002	Phase 3
0.6347	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6832	Phase 2
0.633	Remote Similarity	NPD7907	Approved
0.6328	Remote Similarity	NPD3748	Approved
0.6324	Remote Similarity	NPD3226	Approved
0.6322	Remote Similarity	NPD8032	Phase 2
0.6316	Remote Similarity	NPD8319	Approved
0.6316	Remote Similarity	NPD8320	Phase 1
0.6311	Remote Similarity	NPD8285	Discontinued
0.6308	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5403	Approved
0.6296	Remote Similarity	NPD3882	Suspended
0.6291	Remote Similarity	NPD7801	Approved
0.6284	Remote Similarity	NPD5401	Approved
0.628	Remote Similarity	NPD4107	Approved
0.6279	Remote Similarity	NPD7930	Approved
0.6278	Remote Similarity	NPD1243	Approved
0.6277	Remote Similarity	NPD2801	Approved
0.6271	Remote Similarity	NPD7097	Phase 1
0.6262	Remote Similarity	NPD7700	Phase 2
0.6262	Remote Similarity	NPD7699	Phase 2
0.6257	Remote Similarity	NPD5762	Approved
0.6257	Remote Similarity	NPD2346	Discontinued
0.6257	Remote Similarity	NPD5763	Approved
0.6257	Remote Similarity	NPD1471	Phase 3
0.6257	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD8361	Approved
0.6238	Remote Similarity	NPD8360	Approved
0.6238	Remote Similarity	NPD8435	Approved
0.6237	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD1549	Phase 2
0.622	Remote Similarity	NPD6823	Phase 2
0.6201	Remote Similarity	NPD6099	Approved
0.6201	Remote Similarity	NPD1551	Phase 2
0.6201	Remote Similarity	NPD6100	Approved
0.6196	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7680	Approved
0.6188	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD4482	Phase 3
0.6167	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD4665	Approved
0.6164	Remote Similarity	NPD4111	Phase 1
0.6158	Remote Similarity	NPD5353	Approved
0.6158	Remote Similarity	NPD5735	Approved
0.6154	Remote Similarity	NPD3750	Approved
0.6145	Remote Similarity	NPD7033	Discontinued
0.6145	Remote Similarity	NPD2799	Discontinued
0.614	Remote Similarity	NPD7078	Approved
0.6134	Remote Similarity	NPD7229	Phase 3
0.6134	Remote Similarity	NPD7315	Approved
0.6133	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7999	Approved
0.6127	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7058	Phase 2
0.6126	Remote Similarity	NPD7057	Phase 3
0.6117	Remote Similarity	NPD6535	Approved
0.6117	Remote Similarity	NPD6534	Approved
0.6111	Remote Similarity	NPD2935	Discontinued
0.6109	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4420	Approved
0.6105	Remote Similarity	NPD7736	Approved
0.6102	Remote Similarity	NPD4140	Approved
0.6102	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD2800	Approved
0.608	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6355	Discontinued
0.6067	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5005	Approved
0.6066	Remote Similarity	NPD5006	Approved
0.6066	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD4110	Phase 3
0.6051	Remote Similarity	NPD5710	Approved
0.6051	Remote Similarity	NPD5711	Approved
0.6048	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5327	Phase 3

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