NPASS Compound

Structure

CID326661 OpenBabel06191716192D 21 21 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 10 1 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 1 1 1 0 0 0 10 20 1 0 0 0 0 11 2 1 6 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 16 1 1 0 0 0 13 15 1 0 0 0 0 13 17 1 6 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 1 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.17
Volume:	306.908
LogP:	1.844
LogD:	0.004
LogS:	-1.344
# Rotatable Bonds:	8
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.464
Synthetic Accessibility Score:	4.237
Fsp3:	0.8
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:	-5.65
MDCK Permeability:	0.00015917127893771976
Pgp-inhibitor:	0.001
Pgp-substrate:	0.128
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.312
Plasma Protein Binding (PPB):	39.19602966308594%
Volume Distribution (VD):	0.501
Pgp-substrate:	31.45288848876953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	3.801
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.082
AMES Toxicity:	0.423
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.837
Carcinogencity:	0.215
Eye Corrosion:	0.023
Eye Irritation:	0.657
Respiratory Toxicity:	0.077

Download Data

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

Natural Product: NPC326661

Natural Product ID:	NPC326661
*Common Name:**	(E,8R)-8-[(2R,3R,5R,6S)-3,5-Dihydroxy-6-Methyloxan-2-Yl]Oxynon-2-Enoic Acid
IUPAC Name:	(E,8R)-8-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxynon-2-enoic acid
Synonyms:
Standard InCHIKey:	MWGRRKDIJLJLMO-OSYKULTDSA-N
Standard InCHI:	InChI=1S/C15H26O6/c1-10(7-5-3-4-6-8-14(18)19)20-15-13(17)9-12(16)11(2)21-15/h6,8,10-13,15-17H,3-5,7,9H2,1-2H3,(H,18,19)/b8-6+/t10-,11+,12-,13-,15-/m1/s1
SMILES:	CC1C(CC(C(O1)OC(C)CCCCC=CC(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1221889
PubChem CID:	16066476
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000215] Sugar 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
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15690045]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16529801]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17558398]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18650807]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18791072]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19346493]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19549143]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22235948]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22239548]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[222395484]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23163760]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23475189]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23894595]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24411940]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24453122]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	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
EC50	2
Potency	5

Activity Type	# Activity
Individual Protein	3
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	56234.1	nM	PMID[532205]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[532205]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[532205]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	EC50	=	370.0	nM	PMID[532204]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	EC50	=	1100.0	nM	PMID[532204]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	14715.7	nM	PMID[532205]
NPT2	Others	Unspecified		Potency	n.a.	6309.6	nM	PMID[532205]

☑ 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 NPC326661 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	148
0.1-0.2	2136
0.2-0.3	6728
0.3-0.4	16450
0.4-0.5	10304
0.5-0.6	5572
0.6-0.7	1163
0.7-0.8	161
0.8-0.85	21
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9079	High Similarity	NPC469469
0.8974	High Similarity	NPC473308
0.8846	High Similarity	NPC473315
0.8846	High Similarity	NPC142111
0.875	High Similarity	NPC208473
0.8734	High Similarity	NPC475035
0.8718	High Similarity	NPC251026
0.85	High Similarity	NPC266718
0.8415	Intermediate Similarity	NPC475037
0.8313	Intermediate Similarity	NPC470137
0.8205	Intermediate Similarity	NPC248775
0.8193	Intermediate Similarity	NPC118077
0.8193	Intermediate Similarity	NPC475186
0.8171	Intermediate Similarity	NPC470124
0.8171	Intermediate Similarity	NPC475034
0.8169	Intermediate Similarity	NPC294813
0.8169	Intermediate Similarity	NPC13143
0.8158	Intermediate Similarity	NPC472174
0.8118	Intermediate Similarity	NPC473311
0.8101	Intermediate Similarity	NPC470148
0.8101	Intermediate Similarity	NPC470149
0.8101	Intermediate Similarity	NPC180725
0.8077	Intermediate Similarity	NPC474026
0.8077	Intermediate Similarity	NPC110813
0.8026	Intermediate Similarity	NPC132938
0.8023	Intermediate Similarity	NPC469410
0.8	Intermediate Similarity	NPC470147
0.8	Intermediate Similarity	NPC133226
0.8	Intermediate Similarity	NPC127295
0.8	Intermediate Similarity	NPC163362
0.7975	Intermediate Similarity	NPC133377
0.7949	Intermediate Similarity	NPC229655
0.7931	Intermediate Similarity	NPC472196
0.7931	Intermediate Similarity	NPC472195
0.7931	Intermediate Similarity	NPC238090
0.7922	Intermediate Similarity	NPC472173
0.7901	Intermediate Similarity	NPC280367
0.7901	Intermediate Similarity	NPC236649
0.7901	Intermediate Similarity	NPC21693
0.7848	Intermediate Similarity	NPC475711
0.7841	Intermediate Similarity	NPC159698
0.7816	Intermediate Similarity	NPC477749
0.7808	Intermediate Similarity	NPC19769
0.7791	Intermediate Similarity	NPC285588
0.7791	Intermediate Similarity	NPC477748
0.7711	Intermediate Similarity	NPC473500
0.7711	Intermediate Similarity	NPC38295
0.7711	Intermediate Similarity	NPC156089
0.7711	Intermediate Similarity	NPC470313
0.7703	Intermediate Similarity	NPC201356
0.7701	Intermediate Similarity	NPC202886
0.7701	Intermediate Similarity	NPC118078
0.7654	Intermediate Similarity	NPC179933
0.7654	Intermediate Similarity	NPC1180
0.7614	Intermediate Similarity	NPC110072
0.7568	Intermediate Similarity	NPC96414
0.7564	Intermediate Similarity	NPC55652
0.7564	Intermediate Similarity	NPC185186
0.7564	Intermediate Similarity	NPC327383
0.7532	Intermediate Similarity	NPC476037
0.7532	Intermediate Similarity	NPC474078
0.7532	Intermediate Similarity	NPC476012
0.7529	Intermediate Similarity	NPC471494
0.75	Intermediate Similarity	NPC6414
0.75	Intermediate Similarity	NPC303451
0.7471	Intermediate Similarity	NPC137368
0.7467	Intermediate Similarity	NPC276299
0.7444	Intermediate Similarity	NPC294293
0.7442	Intermediate Similarity	NPC311163
0.7439	Intermediate Similarity	NPC321728
0.7436	Intermediate Similarity	NPC475762
0.7432	Intermediate Similarity	NPC31496
0.7416	Intermediate Similarity	NPC472199
0.7416	Intermediate Similarity	NPC472197
0.7407	Intermediate Similarity	NPC233071
0.7397	Intermediate Similarity	NPC26810
0.7375	Intermediate Similarity	NPC285840
0.7375	Intermediate Similarity	NPC327041
0.7368	Intermediate Similarity	NPC25298
0.7342	Intermediate Similarity	NPC329914
0.7342	Intermediate Similarity	NPC329890
0.734	Intermediate Similarity	NPC475655
0.734	Intermediate Similarity	NPC2313
0.734	Intermediate Similarity	NPC57586
0.734	Intermediate Similarity	NPC475157
0.734	Intermediate Similarity	NPC154132
0.734	Intermediate Similarity	NPC471637
0.7333	Intermediate Similarity	NPC61201
0.7326	Intermediate Similarity	NPC477746
0.7326	Intermediate Similarity	NPC477747
0.7317	Intermediate Similarity	NPC477314
0.7303	Intermediate Similarity	NPC327253
0.7297	Intermediate Similarity	NPC277570
0.7284	Intermediate Similarity	NPC188860
0.7283	Intermediate Similarity	NPC306041
0.7273	Intermediate Similarity	NPC63873
0.7263	Intermediate Similarity	NPC201191
0.726	Intermediate Similarity	NPC155457
0.7253	Intermediate Similarity	NPC2003
0.7253	Intermediate Similarity	NPC25701
0.7253	Intermediate Similarity	NPC472198
0.7253	Intermediate Similarity	NPC256368
0.725	Intermediate Similarity	NPC474545
0.7216	Intermediate Similarity	NPC315070
0.7209	Intermediate Similarity	NPC288471
0.7204	Intermediate Similarity	NPC474194
0.7204	Intermediate Similarity	NPC476613
0.7204	Intermediate Similarity	NPC476612
0.7188	Intermediate Similarity	NPC197736
0.7179	Intermediate Similarity	NPC475982
0.7179	Intermediate Similarity	NPC130618
0.7176	Intermediate Similarity	NPC310450
0.7176	Intermediate Similarity	NPC11383
0.7176	Intermediate Similarity	NPC475046
0.7176	Intermediate Similarity	NPC474959
0.7174	Intermediate Similarity	NPC469543
0.7174	Intermediate Similarity	NPC170204
0.7159	Intermediate Similarity	NPC316138
0.7159	Intermediate Similarity	NPC313658
0.7158	Intermediate Similarity	NPC198992
0.7143	Intermediate Similarity	NPC320089
0.7143	Intermediate Similarity	NPC320552
0.7128	Intermediate Similarity	NPC169468
0.7128	Intermediate Similarity	NPC61630
0.7128	Intermediate Similarity	NPC81483
0.7128	Intermediate Similarity	NPC307517
0.7111	Intermediate Similarity	NPC3952
0.7111	Intermediate Similarity	NPC471569
0.7097	Intermediate Similarity	NPC241911
0.7093	Intermediate Similarity	NPC263087
0.7093	Intermediate Similarity	NPC31019
0.7093	Intermediate Similarity	NPC284472
0.7093	Intermediate Similarity	NPC44261
0.7093	Intermediate Similarity	NPC106912
0.7093	Intermediate Similarity	NPC229799
0.7093	Intermediate Similarity	NPC27314
0.7093	Intermediate Similarity	NPC286770
0.7093	Intermediate Similarity	NPC2379
0.7083	Intermediate Similarity	NPC195510
0.7083	Intermediate Similarity	NPC13171
0.7079	Intermediate Similarity	NPC471755
0.7079	Intermediate Similarity	NPC471756
0.7073	Intermediate Similarity	NPC49392
0.7073	Intermediate Similarity	NPC190400
0.7059	Intermediate Similarity	NPC297440
0.7053	Intermediate Similarity	NPC306344
0.7053	Intermediate Similarity	NPC22149
0.7053	Intermediate Similarity	NPC255677
0.7051	Intermediate Similarity	NPC475760
0.7045	Intermediate Similarity	NPC47937
0.7033	Intermediate Similarity	NPC9447
0.7024	Intermediate Similarity	NPC139712
0.7021	Intermediate Similarity	NPC472290
0.7013	Intermediate Similarity	NPC146811
0.7011	Intermediate Similarity	NPC220167
0.7011	Intermediate Similarity	NPC136699
0.7	Intermediate Similarity	NPC133450
0.7	Intermediate Similarity	NPC478110
0.6986	Remote Similarity	NPC320032
0.6979	Remote Similarity	NPC298255
0.6979	Remote Similarity	NPC476611
0.6979	Remote Similarity	NPC28304
0.6974	Remote Similarity	NPC148233
0.6974	Remote Similarity	NPC475221
0.6974	Remote Similarity	NPC25747
0.697	Remote Similarity	NPC254538
0.697	Remote Similarity	NPC474285
0.6957	Remote Similarity	NPC473723
0.6957	Remote Similarity	NPC473561
0.6957	Remote Similarity	NPC475173
0.6957	Remote Similarity	NPC473663
0.6957	Remote Similarity	NPC473520
0.6951	Remote Similarity	NPC473948
0.6947	Remote Similarity	NPC203627
0.6947	Remote Similarity	NPC40182
0.6947	Remote Similarity	NPC198422
0.6947	Remote Similarity	NPC472015
0.6944	Remote Similarity	NPC472808
0.6944	Remote Similarity	NPC324224
0.6941	Remote Similarity	NPC100697
0.6933	Remote Similarity	NPC113293
0.6932	Remote Similarity	NPC471567
0.6932	Remote Similarity	NPC120398
0.6932	Remote Similarity	NPC322529
0.6932	Remote Similarity	NPC73166
0.6932	Remote Similarity	NPC182383
0.6923	Remote Similarity	NPC209047
0.6923	Remote Similarity	NPC43074
0.6923	Remote Similarity	NPC74672
0.6923	Remote Similarity	NPC122627
0.6923	Remote Similarity	NPC139782
0.6923	Remote Similarity	NPC117596
0.6923	Remote Similarity	NPC473904
0.6923	Remote Similarity	NPC177668
0.6923	Remote Similarity	NPC242503
0.6915	Remote Similarity	NPC54731
0.6915	Remote Similarity	NPC288350
0.6915	Remote Similarity	NPC173329
0.6914	Remote Similarity	NPC470435
0.6914	Remote Similarity	NPC477311

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 NPC326661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	2484
0.2-0.3	4130
0.3-0.4	1748
0.4-0.5	492
0.5-0.6	130
0.6-0.7	28
0.7-0.8	0
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
0.6947	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7838	Discovery
0.6739	Remote Similarity	NPD6698	Approved
0.6739	Remote Similarity	NPD46	Approved
0.6733	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD1407	Approved
0.6479	Remote Similarity	NPD904	Phase 3
0.6479	Remote Similarity	NPD905	Approved
0.6465	Remote Similarity	NPD5344	Discontinued
0.6444	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7983	Approved
0.6301	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD888	Phase 3
0.6301	Remote Similarity	NPD891	Phase 3
0.6301	Remote Similarity	NPD894	Approved
0.6301	Remote Similarity	NPD892	Phase 3
0.6301	Remote Similarity	NPD895	Approved
0.6301	Remote Similarity	NPD887	Approved
0.6301	Remote Similarity	NPD889	Approved
0.6301	Remote Similarity	NPD893	Approved
0.6296	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD2269	Approved
0.6161	Remote Similarity	NPD7503	Approved
0.6129	Remote Similarity	NPD4249	Approved
0.6104	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD6109	Phase 1
0.6098	Remote Similarity	NPD897	Approved
0.6098	Remote Similarity	NPD896	Approved
0.6098	Remote Similarity	NPD898	Approved
0.6075	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4251	Approved
0.6064	Remote Similarity	NPD4250	Approved
0.6053	Remote Similarity	NPD7830	Approved
0.6053	Remote Similarity	NPD2267	Suspended
0.6053	Remote Similarity	NPD7829	Approved
0.604	Remote Similarity	NPD6648	Approved
0.6036	Remote Similarity	NPD7327	Approved
0.6036	Remote Similarity	NPD7641	Discontinued
0.6036	Remote Similarity	NPD7328	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD8997	Approved
0.6	Remote Similarity	NPD8998	Phase 2
0.6	Remote Similarity	NPD8993	Phase 1
0.6	Remote Similarity	NPD9000	Phase 3
0.6	Remote Similarity	NPD8999	Phase 3
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7516	Approved
0.5978	Remote Similarity	NPD6110	Phase 1
0.5929	Remote Similarity	NPD8377	Approved
0.5929	Remote Similarity	NPD8294	Approved
0.5926	Remote Similarity	NPD3197	Phase 1
0.5913	Remote Similarity	NPD7642	Approved
0.59	Remote Similarity	NPD7839	Suspended
0.5897	Remote Similarity	NPD69	Approved
0.5897	Remote Similarity	NPD9119	Approved
0.5877	Remote Similarity	NPD8296	Approved
0.5877	Remote Similarity	NPD8335	Approved
0.5877	Remote Similarity	NPD8517	Approved
0.5877	Remote Similarity	NPD8513	Phase 3
0.5877	Remote Similarity	NPD8378	Approved
0.5877	Remote Similarity	NPD8380	Approved
0.5877	Remote Similarity	NPD8379	Approved
0.5877	Remote Similarity	NPD8516	Approved
0.5877	Remote Similarity	NPD8033	Approved
0.5877	Remote Similarity	NPD8515	Approved
0.5833	Remote Similarity	NPD8966	Approved
0.5833	Remote Similarity	NPD8965	Approved
0.5784	Remote Similarity	NPD4225	Approved
0.5778	Remote Similarity	NPD4268	Approved
0.5778	Remote Similarity	NPD4271	Approved
0.5769	Remote Similarity	NPD9118	Approved
0.575	Remote Similarity	NPD6123	Approved
0.5739	Remote Similarity	NPD8444	Approved
0.5726	Remote Similarity	NPD8341	Approved
0.5726	Remote Similarity	NPD8299	Approved
0.5726	Remote Similarity	NPD8340	Approved
0.5726	Remote Similarity	NPD8342	Approved
0.5688	Remote Similarity	NPD6371	Approved
0.5678	Remote Similarity	NPD7507	Approved
0.5667	Remote Similarity	NPD4756	Discovery
0.5663	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD7637	Suspended
0.5652	Remote Similarity	NPD4819	Approved
0.5652	Remote Similarity	NPD4822	Approved
0.5652	Remote Similarity	NPD4821	Approved
0.5652	Remote Similarity	NPD4820	Approved
0.5638	Remote Similarity	NPD7154	Phase 3
0.561	Remote Similarity	NPD847	Phase 1
0.561	Remote Similarity	NPD8961	Approved
0.56	Remote Similarity	NPD5778	Approved
0.56	Remote Similarity	NPD5779	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