NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	526.22
Volume:	519.458
LogP:	2.765
LogD:	1.18
LogS:	-3.584
# Rotatable Bonds:	6
TPSA:	129.34
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.356
Synthetic Accessibility Score:	6.17
Fsp3:	0.655
Lipinski Rule-of-5:	Accepted
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:	-5.372
MDCK Permeability:	8.321283530676737e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.469
20% Bioavailability (F20%):	0.621
30% Bioavailability (F30%):	0.485

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.854
Plasma Protein Binding (PPB):	73.61463165283203%
Volume Distribution (VD):	0.656
Pgp-substrate:	20.47498893737793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.39
CYP2C19-inhibitor:	0.181
CYP2C19-substrate:	0.197
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.505

ADMET: Excretion

Clearance (CL):	5.596
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.381
Drug-inuced Liver Injury (DILI):	0.773
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.992
Maximum Recommended Daily Dose:	0.793
Skin Sensitization:	0.098
Carcinogencity:	0.142
Eye Corrosion:	0.006
Eye Irritation:	0.019
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC478178

Natural Product ID:	NPC478178
*Common Name:**	methyl 2-[(1R,2S,5R,6R,12R,14S,15R,17S,18S)-14-acetyloxy-6-(furan-3-yl)-17-hydroxy-1,5,15-trimethyl-8,13-dioxo-7-oxapentacyclo[13.2.1.02,11.05,10.012,17]octadec-10-en-18-yl]acetate
IUPAC Name:	methyl 2-[(1R,2S,5R,6R,12R,14S,15R,17S,18S)-14-acetyloxy-6-(furan-3-yl)-17-hydroxy-1,5,15-trimethyl-8,13-dioxo-7-oxapentacyclo[13.2.1.02,11.05,10.012,17]octadec-10-en-18-yl]acetate
Synonyms:
Standard InCHIKey:	PYPSEKRVSQOCAG-AXCPAWLWSA-N
Standard InCHI:	InChI=1S/C29H34O9/c1-14(30)37-25-23(33)22-21-16(28(4)18(11-19(31)35-5)27(25,3)13-29(22,28)34)6-8-26(2)17(21)10-20(32)38-24(26)15-7-9-36-12-15/h7,9,12,16,18,22,24-25,34H,6,8,10-11,13H2,1-5H3/t16-,18-,22-,24-,25+,26+,27+,28+,29-/m0/s1
SMILES:	CC(=O)O[C@@H]1C(=O)[C@@H]2C3=C4CC(=O)O[C@H]([C@@]4(CC[C@@H]3[C@]5([C@@]2(C[C@@]1([C@@H]5CC(=O)OC)C)O)C)C)C6=COC=C6
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122181596
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids 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
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112995]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20146503]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	Thai	n.a.	PMID[21733687]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22724531]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26114936]
NPO6445	Xylocarpus moluccensis	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	113500	nM	PMID[26114936]

☑ 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 NPC478178 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	360
0.1-0.2	1477
0.2-0.3	3130
0.3-0.4	5654
0.4-0.5	10971
0.5-0.6	10546
0.6-0.7	9168
0.7-0.8	958
0.8-0.85	292
0.85-0.9	122
0.9-0.95	16
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9682	High Similarity	NPC478179
0.9615	High Similarity	NPC165218
0.9503	High Similarity	NPC236004
0.9387	High Similarity	NPC478177
0.9383	High Similarity	NPC94763
0.9255	High Similarity	NPC327922
0.925	High Similarity	NPC214600
0.9146	High Similarity	NPC469576
0.9141	High Similarity	NPC159232
0.913	High Similarity	NPC149945
0.9125	High Similarity	NPC663
0.9125	High Similarity	NPC224394
0.9091	High Similarity	NPC469633
0.9062	High Similarity	NPC472767
0.9062	High Similarity	NPC6326
0.9062	High Similarity	NPC197596
0.9057	High Similarity	NPC477403
0.9057	High Similarity	NPC474932
0.9042	High Similarity	NPC470938
0.903	High Similarity	NPC471437
0.9006	High Similarity	NPC234660
0.9006	High Similarity	NPC51568
0.8994	High Similarity	NPC249021
0.8987	High Similarity	NPC214541
0.8987	High Similarity	NPC44675
0.8957	High Similarity	NPC476861
0.8957	High Similarity	NPC476850
0.8951	High Similarity	NPC476856
0.8951	High Similarity	NPC476857
0.8951	High Similarity	NPC476858
0.8944	High Similarity	NPC5079
0.8938	High Similarity	NPC473473
0.8938	High Similarity	NPC475295
0.8931	High Similarity	NPC204663
0.8924	High Similarity	NPC57998
0.8909	High Similarity	NPC285227
0.8889	High Similarity	NPC292389
0.8889	High Similarity	NPC469338
0.8882	High Similarity	NPC242068
0.8882	High Similarity	NPC477402
0.8882	High Similarity	NPC472653
0.8882	High Similarity	NPC247563
0.8882	High Similarity	NPC25255
0.8875	High Similarity	NPC286722
0.8875	High Similarity	NPC36655
0.8875	High Similarity	NPC195131
0.8875	High Similarity	NPC261597
0.8868	High Similarity	NPC264943
0.8868	High Similarity	NPC469336
0.8861	High Similarity	NPC469503
0.8841	High Similarity	NPC476224
0.8841	High Similarity	NPC476853
0.8841	High Similarity	NPC472764
0.8834	High Similarity	NPC470940
0.8834	High Similarity	NPC469849
0.8834	High Similarity	NPC476860
0.8834	High Similarity	NPC123088
0.8834	High Similarity	NPC276551
0.8827	High Similarity	NPC96443
0.8827	High Similarity	NPC82851
0.8827	High Similarity	NPC193798
0.8827	High Similarity	NPC69028
0.8827	High Similarity	NPC290400
0.8812	High Similarity	NPC209364
0.8805	High Similarity	NPC178932
0.8805	High Similarity	NPC282445
0.879	High Similarity	NPC472654
0.8788	High Similarity	NPC472765
0.8788	High Similarity	NPC472766
0.878	High Similarity	NPC470875
0.878	High Similarity	NPC23387
0.8773	High Similarity	NPC134254
0.8773	High Similarity	NPC39986
0.8773	High Similarity	NPC302369
0.8773	High Similarity	NPC419
0.8773	High Similarity	NPC477405
0.8772	High Similarity	NPC105395
0.8765	High Similarity	NPC335761
0.8758	High Similarity	NPC187149
0.8758	High Similarity	NPC45101
0.8758	High Similarity	NPC472772
0.8758	High Similarity	NPC472283
0.8758	High Similarity	NPC470118
0.8743	High Similarity	NPC469848
0.8742	High Similarity	NPC246164
0.8734	High Similarity	NPC159927
0.8734	High Similarity	NPC476122
0.8734	High Similarity	NPC469335
0.8734	High Similarity	NPC156189
0.8727	High Similarity	NPC472774
0.8727	High Similarity	NPC472651
0.8727	High Similarity	NPC472775
0.8727	High Similarity	NPC173516
0.8718	High Similarity	NPC346
0.8712	High Similarity	NPC329938
0.8712	High Similarity	NPC472668
0.8712	High Similarity	NPC149896
0.8712	High Similarity	NPC117986
0.8704	High Similarity	NPC475967
0.8698	High Similarity	NPC470181
0.8696	High Similarity	NPC126723
0.8696	High Similarity	NPC107646
0.8696	High Similarity	NPC469485
0.869	High Similarity	NPC471632
0.8688	High Similarity	NPC30222
0.8683	High Similarity	NPC169299
0.8683	High Similarity	NPC160818
0.8679	High Similarity	NPC272590
0.8675	High Similarity	NPC271235
0.8675	High Similarity	NPC242334
0.8675	High Similarity	NPC471397
0.8675	High Similarity	NPC472652
0.8671	High Similarity	NPC195325
0.8662	High Similarity	NPC471174
0.8662	High Similarity	NPC250228
0.8662	High Similarity	NPC470941
0.8659	High Similarity	NPC472669
0.8659	High Similarity	NPC471168
0.865	High Similarity	NPC470789
0.865	High Similarity	NPC475381
0.865	High Similarity	NPC191828
0.8642	High Similarity	NPC173544
0.8634	High Similarity	NPC35000
0.8634	High Similarity	NPC469850
0.8623	High Similarity	NPC470995
0.8623	High Similarity	NPC472659
0.8616	High Similarity	NPC477404
0.8616	High Similarity	NPC196864
0.8614	High Similarity	NPC472282
0.8606	High Similarity	NPC271657
0.8599	High Similarity	NPC262198
0.8598	High Similarity	NPC472771
0.8598	High Similarity	NPC263432
0.8598	High Similarity	NPC200782
0.8598	High Similarity	NPC470939
0.8598	High Similarity	NPC18347
0.8598	High Similarity	NPC471166
0.8598	High Similarity	NPC471167
0.859	High Similarity	NPC251865
0.8589	High Similarity	NPC237155
0.8589	High Similarity	NPC475226
0.8581	High Similarity	NPC121158
0.858	High Similarity	NPC60973
0.8563	High Similarity	NPC160651
0.8554	High Similarity	NPC472141
0.8553	High Similarity	NPC470791
0.8553	High Similarity	NPC470790
0.8545	High Similarity	NPC472139
0.8545	High Similarity	NPC472773
0.8545	High Similarity	NPC469846
0.8544	High Similarity	NPC221809
0.8544	High Similarity	NPC216755
0.8537	High Similarity	NPC305016
0.8529	High Similarity	NPC167340
0.8528	High Similarity	NPC197137
0.8528	High Similarity	NPC299038
0.8528	High Similarity	NPC472778
0.8528	High Similarity	NPC472776
0.8528	High Similarity	NPC472777
0.8526	High Similarity	NPC223415
0.8519	High Similarity	NPC141538
0.8519	High Similarity	NPC476262
0.8519	High Similarity	NPC296807
0.8519	High Similarity	NPC92979
0.8519	High Similarity	NPC155939
0.8512	High Similarity	NPC82602
0.8509	High Similarity	NPC476939
0.8509	High Similarity	NPC44577
0.8509	High Similarity	NPC476201
0.8509	High Similarity	NPC75906
0.8509	High Similarity	NPC476940
0.8503	High Similarity	NPC473753
0.8503	High Similarity	NPC473766
0.85	High Similarity	NPC470997
0.8494	Intermediate Similarity	NPC470182
0.8494	Intermediate Similarity	NPC261184
0.8485	Intermediate Similarity	NPC5741
0.8485	Intermediate Similarity	NPC211777
0.8476	Intermediate Similarity	NPC307383
0.8476	Intermediate Similarity	NPC472779
0.8471	Intermediate Similarity	NPC476944
0.8471	Intermediate Similarity	NPC477824
0.8466	Intermediate Similarity	NPC263265
0.8447	Intermediate Similarity	NPC18135
0.8447	Intermediate Similarity	NPC116717
0.8443	Intermediate Similarity	NPC475779
0.8438	Intermediate Similarity	NPC329180
0.8438	Intermediate Similarity	NPC471001
0.8434	Intermediate Similarity	NPC198047
0.8428	Intermediate Similarity	NPC255414
0.8421	Intermediate Similarity	NPC262386
0.8415	Intermediate Similarity	NPC167142
0.8408	Intermediate Similarity	NPC470741
0.8408	Intermediate Similarity	NPC243577
0.8405	Intermediate Similarity	NPC281258
0.8405	Intermediate Similarity	NPC471175
0.8395	Intermediate Similarity	NPC33938
0.8393	Intermediate Similarity	NPC100333
0.8385	Intermediate Similarity	NPC46551
0.8383	Intermediate Similarity	NPC259943

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 NPC478178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	1010
0.2-0.3	2237
0.3-0.4	2712
0.4-0.5	1829
0.5-0.6	768
0.6-0.7	272
0.7-0.8	15
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8868	High Similarity	NPD5760	Phase 2
0.8868	High Similarity	NPD5761	Phase 2
0.8204	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD6764	Approved
0.8103	Intermediate Similarity	NPD6765	Approved
0.8079	Intermediate Similarity	NPD8434	Phase 2
0.7921	Intermediate Similarity	NPD6785	Approved
0.7921	Intermediate Similarity	NPD6784	Approved
0.747	Intermediate Similarity	NPD7236	Approved
0.7374	Intermediate Similarity	NPD7799	Discontinued
0.7353	Intermediate Similarity	NPD7239	Suspended
0.7341	Intermediate Similarity	NPD7819	Suspended
0.7341	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7075	Discontinued
0.7243	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6599	Discontinued
0.7135	Intermediate Similarity	NPD6273	Approved
0.7093	Intermediate Similarity	NPD920	Approved
0.7053	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD8404	Phase 2
0.7041	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6559	Discontinued
0.7022	Intermediate Similarity	NPD3749	Approved
0.6989	Remote Similarity	NPD6801	Discontinued
0.6983	Remote Similarity	NPD919	Approved
0.6977	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7058	Phase 2
0.6966	Remote Similarity	NPD7057	Phase 3
0.6964	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1471	Phase 3
0.6944	Remote Similarity	NPD5494	Approved
0.6941	Remote Similarity	NPD4628	Phase 3
0.6932	Remote Similarity	NPD7411	Suspended
0.6919	Remote Similarity	NPD6799	Approved
0.6914	Remote Similarity	NPD3226	Approved
0.691	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5402	Approved
0.691	Remote Similarity	NPD3817	Phase 2
0.6906	Remote Similarity	NPD1247	Approved
0.6906	Remote Similarity	NPD8127	Discontinued
0.6879	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2534	Approved
0.6879	Remote Similarity	NPD2533	Approved
0.6879	Remote Similarity	NPD2532	Approved
0.6869	Remote Similarity	NPD7497	Discontinued
0.6864	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5763	Approved
0.6864	Remote Similarity	NPD5762	Approved
0.6864	Remote Similarity	NPD6004	Phase 3
0.6864	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6002	Phase 3
0.6864	Remote Similarity	NPD2346	Discontinued
0.6864	Remote Similarity	NPD6005	Phase 3
0.686	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8150	Discontinued
0.6831	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2800	Approved
0.6784	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3882	Suspended
0.6774	Remote Similarity	NPD5844	Phase 1
0.6774	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.676	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7473	Discontinued
0.6755	Remote Similarity	NPD7685	Pre-registration
0.6746	Remote Similarity	NPD2799	Discontinued
0.6737	Remote Similarity	NPD8407	Phase 2
0.6725	Remote Similarity	NPD1549	Phase 2
0.6721	Remote Similarity	NPD6959	Discontinued
0.672	Remote Similarity	NPD3751	Discontinued
0.672	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6100	Approved
0.6706	Remote Similarity	NPD6099	Approved
0.6706	Remote Similarity	NPD2796	Approved
0.6705	Remote Similarity	NPD5403	Approved
0.6703	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7435	Discontinued
0.6686	Remote Similarity	NPD5401	Approved
0.6686	Remote Similarity	NPD1243	Approved
0.6685	Remote Similarity	NPD4380	Phase 2
0.6685	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8312	Approved
0.6684	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD8368	Discontinued
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7033	Discontinued
0.6647	Remote Similarity	NPD3750	Approved
0.6631	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD3818	Discontinued
0.663	Remote Similarity	NPD7199	Phase 2
0.6629	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6166	Phase 2
0.6613	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD1934	Approved
0.6608	Remote Similarity	NPD1551	Phase 2
0.6608	Remote Similarity	NPD2935	Discontinued
0.6607	Remote Similarity	NPD4140	Approved
0.6595	Remote Similarity	NPD6232	Discontinued
0.6595	Remote Similarity	NPD3787	Discontinued
0.6593	Remote Similarity	NPD7768	Phase 2
0.6592	Remote Similarity	NPD7028	Phase 2
0.6591	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2313	Discontinued
0.6579	Remote Similarity	NPD7251	Discontinued
0.657	Remote Similarity	NPD2344	Approved
0.6566	Remote Similarity	NPD6832	Phase 2
0.6559	Remote Similarity	NPD3926	Phase 2
0.655	Remote Similarity	NPD4107	Approved
0.655	Remote Similarity	NPD3748	Approved
0.6548	Remote Similarity	NPD6663	Approved
0.6548	Remote Similarity	NPD8032	Phase 2
0.6545	Remote Similarity	NPD7808	Phase 3
0.6545	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7458	Discontinued
0.6529	Remote Similarity	NPD6353	Approved
0.6526	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6797	Phase 2
0.6513	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5711	Approved
0.6505	Remote Similarity	NPD7229	Phase 3
0.6505	Remote Similarity	NPD5710	Approved
0.6505	Remote Similarity	NPD7874	Approved
0.6505	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4965	Approved
0.6503	Remote Similarity	NPD4966	Approved
0.6503	Remote Similarity	NPD4967	Phase 2
0.6493	Remote Similarity	NPD4111	Phase 1
0.6493	Remote Similarity	NPD4665	Approved
0.6488	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2801	Approved
0.6474	Remote Similarity	NPD7074	Phase 3
0.6471	Remote Similarity	NPD5735	Approved
0.6468	Remote Similarity	NPD6777	Approved
0.6468	Remote Similarity	NPD6780	Approved
0.6468	Remote Similarity	NPD6781	Approved
0.6468	Remote Similarity	NPD6778	Approved
0.6468	Remote Similarity	NPD6779	Approved
0.6468	Remote Similarity	NPD6782	Approved
0.6468	Remote Similarity	NPD6776	Approved
0.6463	Remote Similarity	NPD7078	Approved
0.6453	Remote Similarity	NPD7696	Phase 3
0.6453	Remote Similarity	NPD1510	Phase 2
0.6453	Remote Similarity	NPD7697	Approved
0.6453	Remote Similarity	NPD7698	Approved
0.6446	Remote Similarity	NPD5647	Approved
0.6436	Remote Similarity	NPD4482	Phase 3
0.6433	Remote Similarity	NPD6651	Approved
0.6432	Remote Similarity	NPD6234	Discontinued
0.6429	Remote Similarity	NPD37	Approved
0.6429	Remote Similarity	NPD8435	Approved
0.6422	Remote Similarity	NPD7870	Phase 2
0.6422	Remote Similarity	NPD7871	Phase 2
0.6421	Remote Similarity	NPD7054	Approved
0.642	Remote Similarity	NPD2309	Approved
0.6417	Remote Similarity	NPD7315	Approved
0.6412	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3057	Approved
0.6402	Remote Similarity	NPD1608	Approved
0.6391	Remote Similarity	NPD3268	Approved
0.6391	Remote Similarity	NPD3764	Approved
0.6387	Remote Similarity	NPD7472	Approved
0.6386	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1512	Approved
0.6368	Remote Similarity	NPD7228	Approved
0.6364	Remote Similarity	NPD7003	Approved
0.6364	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4308	Phase 3
0.6354	Remote Similarity	NPD5953	Discontinued
0.6353	Remote Similarity	NPD7961	Discontinued
0.6353	Remote Similarity	NPD6233	Phase 2
0.6349	Remote Similarity	NPD2403	Approved
0.6345	Remote Similarity	NPD8360	Approved
0.6345	Remote Similarity	NPD8361	Approved
0.6341	Remote Similarity	NPD8320	Phase 1
0.6341	Remote Similarity	NPD7492	Approved
0.6341	Remote Similarity	NPD8319	Approved
0.6337	Remote Similarity	NPD6653	Approved
0.6337	Remote Similarity	NPD1607	Approved
0.6335	Remote Similarity	NPD7286	Phase 2
0.6333	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD7095	Approved
0.633	Remote Similarity	NPD6808	Phase 2
0.6329	Remote Similarity	NPD7701	Phase 2
0.6328	Remote Similarity	NPD6190	Approved
0.6328	Remote Similarity	NPD3887	Approved
0.6324	Remote Similarity	NPD2972	Approved
0.6324	Remote Similarity	NPD3533	Approved
0.6316	Remote Similarity	NPD7801	Approved
0.6316	Remote Similarity	NPD1240	Approved
0.6313	Remote Similarity	NPD8491	Approved
0.631	Remote Similarity	NPD5736	Approved
0.6306	Remote Similarity	NPD6650	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data