NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	291.1
Volume:	257.745
LogP:	-3.057
LogD:	-1.02
LogS:	-0.989
# Rotatable Bonds:	4
TPSA:	159.54
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	4.489
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.354
MDCK Permeability:	0.000589305127505213
Pgp-inhibitor:	0.0
Pgp-substrate:	0.394
Human Intestinal Absorption (HIA):	0.883
20% Bioavailability (F20%):	0.92
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.467
Plasma Protein Binding (PPB):	12.458614349365234%
Volume Distribution (VD):	0.266
Pgp-substrate:	84.94389343261719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	1.691
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.302
Drug-inuced Liver Injury (DILI):	0.497
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.421
Carcinogencity:	0.072
Eye Corrosion:	0.004
Eye Irritation:	0.047
Respiratory Toxicity:	0.138

Download Data

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

Natural Product: NPC160066

Natural Product ID:	NPC160066
*Common Name:**	Neodysiherbaine A
IUPAC Name:	(2R,3aR,6R,7R,7aR)-2-[(2S)-2-amino-2-carboxyethyl]-6,7-dihydroxy-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyran-2-carboxylic acid
Synonyms:
Standard InCHIKey:	NRTJEXLNSCGBJU-FQYLSUDWSA-N
Standard InCHI:	InChI=1S/C11H17NO8/c12-4(9(15)16)1-11(10(17)18)2-6-8(20-11)7(14)5(13)3-19-6/h4-8,13-14H,1-3,12H2,(H,15,16)(H,17,18)/t4-,5+,6+,7+,8-,11+/m0/s1
SMILES:	OC(=O)[C@H](C[C@@]1(C[C@@H]2[C@H](O1)[C@H](O)[C@@H](CO2)O)C(=O)O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL221868
PubChem CID:	11460505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0002404] Alpha amino acids [CHEMONTID:0004146] L-alpha-amino acids

*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
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10075800]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10650102]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	Mandapam Coast, Tamilnadu, India	n.a.	PMID[22704923]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9463111]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13321	Viguiera cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16684	Alibertia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	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
ED50	1
Ki	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	16.0	pmol	PMID[448469]
NPT2	Others	Unspecified		Ki	=	151.0	nM	PMID[448469]
NPT2	Others	Unspecified		Ki	=	52.0	nM	PMID[448469]

☑ 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 NPC160066 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	175
0.1-0.2	2204
0.2-0.3	14438
0.3-0.4	15416
0.4-0.5	8974
0.5-0.6	1448
0.6-0.7	41
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7292	Intermediate Similarity	NPC320936
0.71	Intermediate Similarity	NPC292345
0.68	Remote Similarity	NPC83839
0.6696	Remote Similarity	NPC137453
0.6636	Remote Similarity	NPC227622
0.6517	Remote Similarity	NPC106216
0.6517	Remote Similarity	NPC88898
0.6514	Remote Similarity	NPC474952
0.6505	Remote Similarity	NPC470282
0.6396	Remote Similarity	NPC188453
0.6396	Remote Similarity	NPC42320
0.6393	Remote Similarity	NPC477238
0.6381	Remote Similarity	NPC477729
0.6373	Remote Similarity	NPC192025
0.6373	Remote Similarity	NPC125253
0.6373	Remote Similarity	NPC253975
0.6327	Remote Similarity	NPC474003
0.6316	Remote Similarity	NPC471844
0.6263	Remote Similarity	NPC470014
0.6262	Remote Similarity	NPC208537
0.6262	Remote Similarity	NPC270005
0.623	Remote Similarity	NPC477237
0.619	Remote Similarity	NPC52533
0.6176	Remote Similarity	NPC956
0.6168	Remote Similarity	NPC65359
0.6162	Remote Similarity	NPC83108
0.6162	Remote Similarity	NPC214030
0.6154	Remote Similarity	NPC51267
0.6147	Remote Similarity	NPC470283
0.6139	Remote Similarity	NPC219340
0.6134	Remote Similarity	NPC76660
0.6134	Remote Similarity	NPC276995
0.6132	Remote Similarity	NPC203170
0.6068	Remote Similarity	NPC70235
0.6064	Remote Similarity	NPC469925
0.6063	Remote Similarity	NPC474371
0.6058	Remote Similarity	NPC227051
0.6058	Remote Similarity	NPC115995
0.6058	Remote Similarity	NPC277918
0.6055	Remote Similarity	NPC469998
0.6038	Remote Similarity	NPC314364
0.6034	Remote Similarity	NPC236644
0.602	Remote Similarity	NPC125164
0.6019	Remote Similarity	NPC47135
0.6019	Remote Similarity	NPC476019
0.6019	Remote Similarity	NPC165119
0.6	Remote Similarity	NPC233108
0.6	Remote Similarity	NPC68974
0.6	Remote Similarity	NPC190294
0.5984	Remote Similarity	NPC39041
0.5984	Remote Similarity	NPC241294
0.5984	Remote Similarity	NPC471845
0.5984	Remote Similarity	NPC471846
0.5984	Remote Similarity	NPC202722
0.5982	Remote Similarity	NPC323421
0.5982	Remote Similarity	NPC74466
0.5982	Remote Similarity	NPC328562
0.5979	Remote Similarity	NPC96322
0.5978	Remote Similarity	NPC235788
0.5968	Remote Similarity	NPC313802
0.5968	Remote Similarity	NPC314268
0.5968	Remote Similarity	NPC477515
0.5968	Remote Similarity	NPC67917
0.5963	Remote Similarity	NPC469627
0.5962	Remote Similarity	NPC145748
0.5962	Remote Similarity	NPC155670
0.5962	Remote Similarity	NPC95478
0.5957	Remote Similarity	NPC322801
0.5957	Remote Similarity	NPC222327
0.5957	Remote Similarity	NPC291650
0.5957	Remote Similarity	NPC188231
0.5957	Remote Similarity	NPC129100
0.5943	Remote Similarity	NPC470657
0.5943	Remote Similarity	NPC477728
0.5941	Remote Similarity	NPC475616
0.5941	Remote Similarity	NPC473984
0.5938	Remote Similarity	NPC28526
0.5935	Remote Similarity	NPC209734
0.5918	Remote Similarity	NPC51249
0.5918	Remote Similarity	NPC474100
0.5918	Remote Similarity	NPC475232
0.5918	Remote Similarity	NPC473699
0.5918	Remote Similarity	NPC475260
0.5918	Remote Similarity	NPC473775
0.59	Remote Similarity	NPC313762
0.5895	Remote Similarity	NPC286842
0.5895	Remote Similarity	NPC53879
0.5895	Remote Similarity	NPC57788
0.5893	Remote Similarity	NPC31645
0.5888	Remote Similarity	NPC31349
0.5882	Remote Similarity	NPC88943
0.5862	Remote Similarity	NPC215988
0.5856	Remote Similarity	NPC309127
0.5856	Remote Similarity	NPC247877
0.5849	Remote Similarity	NPC476715
0.5847	Remote Similarity	NPC469787
0.5847	Remote Similarity	NPC317534
0.5847	Remote Similarity	NPC469788
0.5847	Remote Similarity	NPC290247
0.5841	Remote Similarity	NPC278028
0.5841	Remote Similarity	NPC470632
0.5841	Remote Similarity	NPC328180
0.5833	Remote Similarity	NPC470284
0.5833	Remote Similarity	NPC82315
0.5818	Remote Similarity	NPC329952
0.5816	Remote Similarity	NPC474468
0.5804	Remote Similarity	NPC322188
0.58	Remote Similarity	NPC244539
0.5798	Remote Similarity	NPC15413
0.5794	Remote Similarity	NPC306838
0.5794	Remote Similarity	NPC476717
0.5789	Remote Similarity	NPC274695
0.5789	Remote Similarity	NPC253995
0.5785	Remote Similarity	NPC246399
0.5785	Remote Similarity	NPC34977
0.5781	Remote Similarity	NPC315783
0.578	Remote Similarity	NPC173926
0.5776	Remote Similarity	NPC324017
0.5776	Remote Similarity	NPC292803
0.5776	Remote Similarity	NPC320019
0.5773	Remote Similarity	NPC473710
0.5773	Remote Similarity	NPC475694
0.5761	Remote Similarity	NPC302188
0.576	Remote Similarity	NPC235625
0.5755	Remote Similarity	NPC475963
0.5755	Remote Similarity	NPC151176
0.5755	Remote Similarity	NPC3464
0.5752	Remote Similarity	NPC470883
0.5752	Remote Similarity	NPC39859
0.5752	Remote Similarity	NPC476009
0.5752	Remote Similarity	NPC158416
0.5752	Remote Similarity	NPC76862
0.575	Remote Similarity	NPC217041
0.5748	Remote Similarity	NPC23963
0.5741	Remote Similarity	NPC51662
0.5738	Remote Similarity	NPC469466
0.5729	Remote Similarity	NPC471418
0.5728	Remote Similarity	NPC318258
0.5728	Remote Similarity	NPC83248
0.5728	Remote Similarity	NPC100204
0.5727	Remote Similarity	NPC477433
0.5727	Remote Similarity	NPC477442
0.5727	Remote Similarity	NPC477444
0.5714	Remote Similarity	NPC137554
0.5714	Remote Similarity	NPC299603
0.5714	Remote Similarity	NPC285014
0.5714	Remote Similarity	NPC255535
0.5714	Remote Similarity	NPC477730
0.5714	Remote Similarity	NPC28959
0.5702	Remote Similarity	NPC182185
0.5701	Remote Similarity	NPC469363
0.57	Remote Similarity	NPC215030
0.5699	Remote Similarity	NPC17455
0.569	Remote Similarity	NPC259654
0.569	Remote Similarity	NPC15993
0.569	Remote Similarity	NPC476270
0.569	Remote Similarity	NPC298266
0.5688	Remote Similarity	NPC322966
0.5688	Remote Similarity	NPC470009
0.5684	Remote Similarity	NPC469926
0.5682	Remote Similarity	NPC121601
0.5682	Remote Similarity	NPC471471
0.5682	Remote Similarity	NPC164476
0.568	Remote Similarity	NPC6531
0.5678	Remote Similarity	NPC114365
0.5678	Remote Similarity	NPC88890
0.5678	Remote Similarity	NPC169089
0.5678	Remote Similarity	NPC18433
0.5678	Remote Similarity	NPC472748
0.5678	Remote Similarity	NPC177518
0.5678	Remote Similarity	NPC132304
0.5678	Remote Similarity	NPC123070
0.5678	Remote Similarity	NPC18044
0.5678	Remote Similarity	NPC154962
0.5676	Remote Similarity	NPC316244
0.5673	Remote Similarity	NPC314466
0.567	Remote Similarity	NPC268922
0.5669	Remote Similarity	NPC305261
0.5664	Remote Similarity	NPC470191
0.5662	Remote Similarity	NPC472430
0.5659	Remote Similarity	NPC325750
0.5657	Remote Similarity	NPC184550
0.5657	Remote Similarity	NPC185419
0.5648	Remote Similarity	NPC313552
0.5644	Remote Similarity	NPC228411
0.5644	Remote Similarity	NPC217725
0.5636	Remote Similarity	NPC477440
0.5636	Remote Similarity	NPC474951
0.5636	Remote Similarity	NPC92974
0.5636	Remote Similarity	NPC477443
0.563	Remote Similarity	NPC472751
0.563	Remote Similarity	NPC472749
0.563	Remote Similarity	NPC475918
0.563	Remote Similarity	NPC228311
0.563	Remote Similarity	NPC120420
0.563	Remote Similarity	NPC41674
0.563	Remote Similarity	NPC469441
0.5619	Remote Similarity	NPC36927
0.5619	Remote Similarity	NPC271772
0.5615	Remote Similarity	NPC313333

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 NPC160066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	111
0.1-0.2	2100
0.2-0.3	4180
0.3-0.4	1921
0.4-0.5	641
0.5-0.6	167
0.6-0.7	29
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7273	Intermediate Similarity	NPD8087	Discontinued
0.71	Intermediate Similarity	NPD618	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD881	Approved
0.6847	Remote Similarity	NPD8307	Discontinued
0.68	Remote Similarity	NPD619	Phase 3
0.6726	Remote Similarity	NPD6941	Approved
0.6723	Remote Similarity	NPD8347	Approved
0.6723	Remote Similarity	NPD8346	Approved
0.6723	Remote Similarity	NPD8345	Approved
0.6696	Remote Similarity	NPD8140	Approved
0.6636	Remote Similarity	NPD8086	Approved
0.6636	Remote Similarity	NPD8139	Approved
0.6636	Remote Similarity	NPD8085	Approved
0.6636	Remote Similarity	NPD8082	Approved
0.6636	Remote Similarity	NPD8083	Approved
0.6636	Remote Similarity	NPD8084	Approved
0.6636	Remote Similarity	NPD8138	Approved
0.6577	Remote Similarity	NPD8275	Approved
0.6577	Remote Similarity	NPD8276	Approved
0.6518	Remote Similarity	NPD8081	Approved
0.6509	Remote Similarity	NPD1446	Phase 3
0.6509	Remote Similarity	NPD1447	Phase 3
0.646	Remote Similarity	NPD8393	Approved
0.6449	Remote Similarity	NPD8394	Approved
0.6337	Remote Similarity	NPD883	Phase 2
0.6337	Remote Similarity	NPD882	Phase 2
0.6304	Remote Similarity	NPD9421	Phase 1
0.6226	Remote Similarity	NPD3716	Discontinued
0.6216	Remote Similarity	NPD2255	Approved
0.6195	Remote Similarity	NPD8301	Approved
0.6195	Remote Similarity	NPD8300	Approved
0.6182	Remote Similarity	NPD6428	Approved
0.6154	Remote Similarity	NPD8306	Approved
0.6154	Remote Similarity	NPD8305	Approved
0.6129	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.608	Remote Similarity	NPD8080	Discontinued
0.6058	Remote Similarity	NPD5193	Discontinued
0.6053	Remote Similarity	NPD7139	Approved
0.6053	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7140	Approved
0.6019	Remote Similarity	NPD7345	Approved
0.6	Remote Similarity	NPD8266	Approved
0.6	Remote Similarity	NPD8267	Approved
0.6	Remote Similarity	NPD8268	Approved
0.6	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD8269	Approved
0.596	Remote Similarity	NPD376	Approved
0.596	Remote Similarity	NPD11	Approved
0.5957	Remote Similarity	NPD9030	Approved
0.5957	Remote Similarity	NPD9031	Approved
0.5957	Remote Similarity	NPD9033	Approved
0.5957	Remote Similarity	NPD9032	Approved
0.5941	Remote Similarity	NPD617	Approved
0.5935	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD2690	Discontinued
0.587	Remote Similarity	NPD9676	Phase 3
0.5856	Remote Similarity	NPD573	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6940	Discontinued
0.5833	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD9385	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD7829	Approved
0.5781	Remote Similarity	NPD7830	Approved
0.5761	Remote Similarity	NPD9656	Approved
0.5758	Remote Similarity	NPD67	Phase 2
0.5758	Remote Similarity	NPD9034	Approved
0.5701	Remote Similarity	NPD394	Phase 3
0.57	Remote Similarity	NPD632	Discontinued
0.5686	Remote Similarity	NPD3160	Suspended
0.5678	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD7916	Approved
0.5645	Remote Similarity	NPD7915	Approved
0.5635	Remote Similarity	NPD7641	Discontinued
0.5615	Remote Similarity	NPD8341	Approved
0.5615	Remote Similarity	NPD8299	Approved
0.5615	Remote Similarity	NPD8340	Approved
0.5615	Remote Similarity	NPD8342	Approved
0.5604	Remote Similarity	NPD9023	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD8959	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