NPASS Compound

Structure

NPC474321 OpenBabel07101718182D 26 25 0 0 1 0 0 0 0 0999 V2000 -13.8564 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 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 -11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -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 1.7321 -1.0000 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 -10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 0.0000 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 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 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 13 16 1 0 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 26 1 0 0 0 0 19 23 2 0 0 0 0 20 24 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.26
Volume:	405.177
LogP:	4.269
LogD:	3.313
LogS:	-4.16
# Rotatable Bonds:	18
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	3.063
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751
MDCK Permeability:	3.606254904298112e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.692
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.749
Plasma Protein Binding (PPB):	95.65635681152344%
Volume Distribution (VD):	0.539
Pgp-substrate:	2.2974464893341064%

ADMET: Metabolism

CYP1A2-inhibitor:	0.166
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.201
CYP2C19-substrate:	0.327
CYP2C9-inhibitor:	0.256
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.696
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	8.39
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.287
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.786
Rat Oral Acute Toxicity:	0.291
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.969
Carcinogencity:	0.507
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.833

Download Data

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

Natural Product: NPC474321

Natural Product ID:	NPC474321
*Common Name:**	2,3-Dihydroxypropyl (9E,11E)-13-Oxooctadeca-9,11-Dienoate
IUPAC Name:	2,3-dihydroxypropyl (9E,11E)-13-oxooctadeca-9,11-dienoate
Synonyms:
Standard InCHIKey:	BABFYBAGZXSUDH-KDFHGORWSA-N
Standard InCHI:	InChI=1S/C21H36O5/c1-2-3-11-14-19(23)15-12-9-7-5-4-6-8-10-13-16-21(25)26-18-20(24)17-22/h7,9,12,15,20,22,24H,2-6,8,10-11,13-14,16-18H2,1H3/b9-7+,15-12+
SMILES:	CCCCCC(=O)/C=C/C=C/CCCCCCCC(=O)OCC(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465241
PubChem CID:	10237201
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic 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
NPO33018	clitocybe clavipes	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444711]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6555	Individual Protein	Aldehyde dehydrogenase 1, mitochondrial	Saccharomyces cerevisiae	Inhibition	<	50.0	%	PMID[541482]

☑ 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 NPC474321 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	185
0.1-0.2	1513
0.2-0.3	6619
0.3-0.4	16208
0.4-0.5	10420
0.5-0.6	5869
0.6-0.7	1504
0.7-0.8	336
0.8-0.85	15
0.85-0.9	19
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9275	High Similarity	NPC476660
0.913	High Similarity	NPC473772
0.9118	High Similarity	NPC330426
0.9118	High Similarity	NPC22101
0.9118	High Similarity	NPC104537
0.9118	High Similarity	NPC148192
0.9118	High Similarity	NPC127091
0.9118	High Similarity	NPC271921
0.8986	High Similarity	NPC473559
0.8986	High Similarity	NPC324981
0.8986	High Similarity	NPC141481
0.8986	High Similarity	NPC48218
0.8841	High Similarity	NPC475443
0.8841	High Similarity	NPC473829
0.8824	High Similarity	NPC296436
0.8824	High Similarity	NPC476654
0.8824	High Similarity	NPC476655
0.8824	High Similarity	NPC176215
0.8824	High Similarity	NPC476657
0.8732	High Similarity	NPC42526
0.8696	High Similarity	NPC83965
0.8696	High Similarity	NPC476656
0.8696	High Similarity	NPC476659
0.8592	High Similarity	NPC143396
0.8406	Intermediate Similarity	NPC476658
0.8382	Intermediate Similarity	NPC40082
0.8261	Intermediate Similarity	NPC54925
0.8235	Intermediate Similarity	NPC174447
0.8235	Intermediate Similarity	NPC251042
0.8235	Intermediate Similarity	NPC81896
0.8235	Intermediate Similarity	NPC229252
0.8235	Intermediate Similarity	NPC122521
0.8235	Intermediate Similarity	NPC321919
0.8235	Intermediate Similarity	NPC143857
0.8133	Intermediate Similarity	NPC227396
0.8116	Intermediate Similarity	NPC201939
0.8116	Intermediate Similarity	NPC321838
0.8088	Intermediate Similarity	NPC106851
0.8088	Intermediate Similarity	NPC274927
0.8056	Intermediate Similarity	NPC26500
0.8056	Intermediate Similarity	NPC99619
0.8028	Intermediate Similarity	NPC326268
0.8028	Intermediate Similarity	NPC245947
0.8028	Intermediate Similarity	NPC136164
0.8028	Intermediate Similarity	NPC255863
0.8028	Intermediate Similarity	NPC318420
0.8026	Intermediate Similarity	NPC260396
0.7971	Intermediate Similarity	NPC243532
0.7945	Intermediate Similarity	NPC209327
0.7945	Intermediate Similarity	NPC273508
0.7901	Intermediate Similarity	NPC144415
0.7901	Intermediate Similarity	NPC253801
0.7887	Intermediate Similarity	NPC68343
0.7887	Intermediate Similarity	NPC328089
0.7848	Intermediate Similarity	NPC1180
0.7848	Intermediate Similarity	NPC469747
0.7848	Intermediate Similarity	NPC263574
0.7831	Intermediate Similarity	NPC477015
0.7805	Intermediate Similarity	NPC163093
0.7778	Intermediate Similarity	NPC473529
0.7778	Intermediate Similarity	NPC180363
0.7778	Intermediate Similarity	NPC473712
0.7778	Intermediate Similarity	NPC131002
0.7778	Intermediate Similarity	NPC473780
0.7778	Intermediate Similarity	NPC65930
0.7778	Intermediate Similarity	NPC11332
0.7778	Intermediate Similarity	NPC73310
0.7778	Intermediate Similarity	NPC475159
0.7778	Intermediate Similarity	NPC145914
0.7778	Intermediate Similarity	NPC329829
0.7778	Intermediate Similarity	NPC94875
0.7763	Intermediate Similarity	NPC329914
0.7763	Intermediate Similarity	NPC325627
0.7763	Intermediate Similarity	NPC329890
0.7722	Intermediate Similarity	NPC11796
0.7722	Intermediate Similarity	NPC218817
0.7722	Intermediate Similarity	NPC182292
0.7714	Intermediate Similarity	NPC235242
0.7711	Intermediate Similarity	NPC477014
0.7711	Intermediate Similarity	NPC477013
0.7711	Intermediate Similarity	NPC120398
0.7711	Intermediate Similarity	NPC471567
0.7711	Intermediate Similarity	NPC322529
0.7692	Intermediate Similarity	NPC49392
0.7692	Intermediate Similarity	NPC190400
0.7662	Intermediate Similarity	NPC160540
0.7654	Intermediate Similarity	NPC21693
0.7654	Intermediate Similarity	NPC236649
0.7647	Intermediate Similarity	NPC18951
0.7647	Intermediate Similarity	NPC477201
0.7647	Intermediate Similarity	NPC325977
0.7632	Intermediate Similarity	NPC320119
0.7619	Intermediate Similarity	NPC134885
0.7619	Intermediate Similarity	NPC309211
0.7619	Intermediate Similarity	NPC134807
0.7619	Intermediate Similarity	NPC219498
0.7619	Intermediate Similarity	NPC473687
0.7619	Intermediate Similarity	NPC308412
0.7619	Intermediate Similarity	NPC69082
0.7619	Intermediate Similarity	NPC279267
0.7619	Intermediate Similarity	NPC477010
0.7619	Intermediate Similarity	NPC210218
0.7619	Intermediate Similarity	NPC204686
0.7606	Intermediate Similarity	NPC320305
0.7606	Intermediate Similarity	NPC328776
0.76	Intermediate Similarity	NPC475982
0.76	Intermediate Similarity	NPC236208
0.759	Intermediate Similarity	NPC156804
0.7568	Intermediate Similarity	NPC25298
0.7558	Intermediate Similarity	NPC477017
0.7558	Intermediate Similarity	NPC477016
0.7558	Intermediate Similarity	NPC280612
0.7536	Intermediate Similarity	NPC323436
0.7532	Intermediate Similarity	NPC470435
0.7532	Intermediate Similarity	NPC326024
0.7531	Intermediate Similarity	NPC47653
0.7529	Intermediate Similarity	NPC477012
0.7529	Intermediate Similarity	NPC178215
0.75	Intermediate Similarity	NPC39167
0.75	Intermediate Similarity	NPC329838
0.75	Intermediate Similarity	NPC475268
0.75	Intermediate Similarity	NPC223677
0.75	Intermediate Similarity	NPC477018
0.75	Intermediate Similarity	NPC473156
0.75	Intermediate Similarity	NPC28779
0.75	Intermediate Similarity	NPC248775
0.75	Intermediate Similarity	NPC192006
0.75	Intermediate Similarity	NPC231009
0.75	Intermediate Similarity	NPC473669
0.75	Intermediate Similarity	NPC329615
0.75	Intermediate Similarity	NPC100921
0.75	Intermediate Similarity	NPC319036
0.75	Intermediate Similarity	NPC228473
0.75	Intermediate Similarity	NPC202055
0.75	Intermediate Similarity	NPC476037
0.75	Intermediate Similarity	NPC473671
0.75	Intermediate Similarity	NPC82795
0.75	Intermediate Similarity	NPC9678
0.75	Intermediate Similarity	NPC476012
0.75	Intermediate Similarity	NPC10316
0.75	Intermediate Similarity	NPC39279
0.75	Intermediate Similarity	NPC103284
0.75	Intermediate Similarity	NPC235809
0.75	Intermediate Similarity	NPC110710
0.75	Intermediate Similarity	NPC223871
0.75	Intermediate Similarity	NPC77871
0.75	Intermediate Similarity	NPC473478
0.75	Intermediate Similarity	NPC25764
0.75	Intermediate Similarity	NPC132496
0.75	Intermediate Similarity	NPC182383
0.75	Intermediate Similarity	NPC66346
0.75	Intermediate Similarity	NPC200845
0.75	Intermediate Similarity	NPC286338
0.75	Intermediate Similarity	NPC283085
0.75	Intermediate Similarity	NPC1083
0.75	Intermediate Similarity	NPC470400
0.75	Intermediate Similarity	NPC292809
0.75	Intermediate Similarity	NPC473651
0.75	Intermediate Similarity	NPC128061
0.75	Intermediate Similarity	NPC477455
0.75	Intermediate Similarity	NPC107986
0.7471	Intermediate Similarity	NPC158388
0.7471	Intermediate Similarity	NPC478003
0.7471	Intermediate Similarity	NPC478004
0.7471	Intermediate Similarity	NPC473311
0.747	Intermediate Similarity	NPC470313
0.747	Intermediate Similarity	NPC473500
0.747	Intermediate Similarity	NPC38295
0.747	Intermediate Similarity	NPC156089
0.7468	Intermediate Similarity	NPC188860
0.7465	Intermediate Similarity	NPC328311
0.7465	Intermediate Similarity	NPC327112
0.7442	Intermediate Similarity	NPC320458
0.7442	Intermediate Similarity	NPC280621
0.7442	Intermediate Similarity	NPC233551
0.7442	Intermediate Similarity	NPC48338
0.7442	Intermediate Similarity	NPC20339
0.7442	Intermediate Similarity	NPC89001
0.7442	Intermediate Similarity	NPC473905
0.7442	Intermediate Similarity	NPC21208
0.7442	Intermediate Similarity	NPC40376
0.7436	Intermediate Similarity	NPC107654
0.7432	Intermediate Similarity	NPC146811
0.7412	Intermediate Similarity	NPC25703
0.7412	Intermediate Similarity	NPC232555
0.7412	Intermediate Similarity	NPC241360
0.7412	Intermediate Similarity	NPC112685
0.7412	Intermediate Similarity	NPC107717
0.7412	Intermediate Similarity	NPC240695
0.7412	Intermediate Similarity	NPC142117
0.7412	Intermediate Similarity	NPC475581
0.7412	Intermediate Similarity	NPC231096
0.7412	Intermediate Similarity	NPC62118
0.7412	Intermediate Similarity	NPC164393
0.7412	Intermediate Similarity	NPC132940
0.7412	Intermediate Similarity	NPC282815
0.7412	Intermediate Similarity	NPC171174
0.7412	Intermediate Similarity	NPC114694
0.7412	Intermediate Similarity	NPC134865
0.7412	Intermediate Similarity	NPC293136

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 NPC474321 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	2237
0.2-0.3	3873
0.3-0.4	1994
0.4-0.5	619
0.5-0.6	216
0.6-0.7	46
0.7-0.8	10
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8143	Intermediate Similarity	NPD3197	Phase 1
0.7465	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3194	Approved
0.7353	Intermediate Similarity	NPD3196	Approved
0.7353	Intermediate Similarity	NPD3728	Approved
0.7353	Intermediate Similarity	NPD3195	Phase 2
0.7353	Intermediate Similarity	NPD4266	Approved
0.7353	Intermediate Similarity	NPD3730	Approved
0.7206	Intermediate Similarity	NPD3172	Approved
0.7191	Intermediate Similarity	NPD7983	Approved
0.7183	Intermediate Similarity	NPD6109	Phase 1
0.716	Intermediate Similarity	NPD4756	Discovery
0.7143	Intermediate Similarity	NPD6435	Approved
0.7105	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6698	Approved
0.7079	Intermediate Similarity	NPD46	Approved
0.7079	Intermediate Similarity	NPD7838	Discovery
0.6912	Remote Similarity	NPD28	Approved
0.6912	Remote Similarity	NPD29	Approved
0.6905	Remote Similarity	NPD5368	Approved
0.6897	Remote Similarity	NPD5363	Approved
0.686	Remote Similarity	NPD7154	Phase 3
0.6824	Remote Similarity	NPD5369	Approved
0.6778	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6101	Approved
0.6706	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6411	Approved
0.6618	Remote Similarity	NPD3173	Approved
0.6579	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5778	Approved
0.6559	Remote Similarity	NPD5779	Approved
0.6552	Remote Similarity	NPD4269	Approved
0.6552	Remote Similarity	NPD4270	Approved
0.6538	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3704	Approved
0.6512	Remote Similarity	NPD4252	Approved
0.6477	Remote Similarity	NPD5362	Discontinued
0.6471	Remote Similarity	NPD4271	Approved
0.6471	Remote Similarity	NPD4268	Approved
0.6471	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD622	Approved
0.6471	Remote Similarity	NPD5343	Approved
0.6444	Remote Similarity	NPD5786	Approved
0.6421	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5209	Approved
0.6354	Remote Similarity	NPD7839	Suspended
0.6329	Remote Similarity	NPD7331	Phase 2
0.6322	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4820	Approved
0.6322	Remote Similarity	NPD4819	Approved
0.6322	Remote Similarity	NPD4821	Approved
0.6322	Remote Similarity	NPD4822	Approved
0.631	Remote Similarity	NPD8039	Approved
0.6296	Remote Similarity	NPD7641	Discontinued
0.6279	Remote Similarity	NPD3732	Approved
0.625	Remote Similarity	NPD6371	Approved
0.6214	Remote Similarity	NPD6686	Approved
0.6196	Remote Similarity	NPD4251	Approved
0.6196	Remote Similarity	NPD4250	Approved
0.6176	Remote Similarity	NPD3174	Discontinued
0.6176	Remote Similarity	NPD4222	Approved
0.6176	Remote Similarity	NPD39	Approved
0.6146	Remote Similarity	NPD7748	Approved
0.6139	Remote Similarity	NPD6647	Phase 2
0.6132	Remote Similarity	NPD8297	Approved
0.6122	Remote Similarity	NPD6084	Phase 2
0.6122	Remote Similarity	NPD6083	Phase 2
0.6117	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7515	Phase 2
0.6087	Remote Similarity	NPD4249	Approved
0.6064	Remote Similarity	NPD5370	Suspended
0.6061	Remote Similarity	NPD4225	Approved
0.6058	Remote Similarity	NPD6881	Approved
0.6058	Remote Similarity	NPD6899	Approved
0.6055	Remote Similarity	NPD7115	Discovery
0.6047	Remote Similarity	NPD818	Approved
0.6047	Remote Similarity	NPD819	Approved
0.6038	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD2699	Approved
0.6029	Remote Similarity	NPD6097	Approved
0.6029	Remote Similarity	NPD6096	Approved
0.5978	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5697	Approved
0.5962	Remote Similarity	NPD6412	Phase 2
0.596	Remote Similarity	NPD7902	Approved
0.5946	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7102	Approved
0.5943	Remote Similarity	NPD7290	Approved
0.5943	Remote Similarity	NPD6883	Approved
0.5941	Remote Similarity	NPD5344	Discontinued
0.5938	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7637	Suspended
0.5934	Remote Similarity	NPD5332	Approved
0.5934	Remote Similarity	NPD6110	Phase 1
0.5934	Remote Similarity	NPD5331	Approved
0.5918	Remote Similarity	NPD5695	Phase 3
0.5914	Remote Similarity	NPD6684	Approved
0.5914	Remote Similarity	NPD5330	Approved
0.5914	Remote Similarity	NPD7521	Approved
0.5914	Remote Similarity	NPD5279	Phase 3
0.5914	Remote Similarity	NPD7146	Approved
0.5914	Remote Similarity	NPD6409	Approved
0.5914	Remote Similarity	NPD6422	Discontinued
0.5914	Remote Similarity	NPD7334	Approved
0.5889	Remote Similarity	NPD4790	Discontinued
0.5888	Remote Similarity	NPD6617	Approved
0.5888	Remote Similarity	NPD8130	Phase 1
0.5888	Remote Similarity	NPD6847	Approved
0.5888	Remote Similarity	NPD6649	Approved
0.5888	Remote Similarity	NPD6869	Approved
0.5888	Remote Similarity	NPD6650	Approved
0.5882	Remote Similarity	NPD5326	Phase 3
0.5877	Remote Similarity	NPD7830	Approved
0.5877	Remote Similarity	NPD7829	Approved
0.5876	Remote Similarity	NPD6399	Phase 3
0.5867	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7128	Approved
0.5865	Remote Similarity	NPD6402	Approved
0.5865	Remote Similarity	NPD6675	Approved
0.5865	Remote Similarity	NPD5739	Approved
0.5849	Remote Similarity	NPD6014	Approved
0.5849	Remote Similarity	NPD6013	Approved
0.5849	Remote Similarity	NPD6012	Approved
0.5842	Remote Similarity	NPD6648	Approved
0.5833	Remote Similarity	NPD6882	Approved
0.5824	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5282	Discontinued
0.5806	Remote Similarity	NPD1694	Approved
0.5806	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7341	Phase 2
0.5789	Remote Similarity	NPD5737	Approved
0.5789	Remote Similarity	NPD6903	Approved
0.5789	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6672	Approved
0.578	Remote Similarity	NPD4632	Approved
0.5773	Remote Similarity	NPD5284	Approved
0.5773	Remote Similarity	NPD5281	Approved
0.5773	Remote Similarity	NPD6079	Approved
0.5755	Remote Similarity	NPD7320	Approved
0.5755	Remote Similarity	NPD6011	Approved
0.5752	Remote Similarity	NPD6319	Approved
0.5743	Remote Similarity	NPD5696	Approved
0.5741	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD8444	Approved
0.5701	Remote Similarity	NPD6372	Approved
0.5701	Remote Similarity	NPD6373	Approved
0.5699	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD3665	Phase 1
0.5699	Remote Similarity	NPD3666	Approved
0.5699	Remote Similarity	NPD3133	Approved
0.5686	Remote Similarity	NPD7798	Approved
0.5679	Remote Similarity	NPD7909	Approved
0.566	Remote Similarity	NPD5701	Approved
0.5657	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD7900	Approved
0.5648	Remote Similarity	NPD6421	Discontinued
0.5641	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6050	Approved
0.5612	Remote Similarity	NPD5694	Approved
0.5604	Remote Similarity	NPD4695	Discontinued
0.5603	Remote Similarity	NPD7642	Approved
0.56	Remote Similarity	NPD5210	Approved
0.56	Remote Similarity	NPD4629	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