NPASS Compound

Structure

NPC51358 OpenBabel07101719252D 28 29 0 0 1 0 0 0 0 0999 V2000 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0878 -1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 15 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 11 1 0 0 0 0 9 14 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 1 1 1 0 0 0 14 18 1 0 0 0 0 15 20 2 0 0 0 0 15 28 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 24 2 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 25 2 0 0 0 0 21 27 1 0 0 0 0 22 3 1 6 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.28
Volume:	536.287
LogP:	2.214
LogD:	1.226
LogS:	-4.006
# Rotatable Bonds:	5
TPSA:	122.65
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	5.202
Fsp3:	0.733
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:	-5.472
MDCK Permeability:	2.9122211344656534e-05
Pgp-inhibitor:	0.465
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.754

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.874
Plasma Protein Binding (PPB):	73.4397964477539%
Volume Distribution (VD):	0.363
Pgp-substrate:	15.7164888381958%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.54
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.422
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.443

ADMET: Excretion

Clearance (CL):	13.75
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.571
Maximum Recommended Daily Dose:	0.239
Skin Sensitization:	0.056
Carcinogencity:	0.713
Eye Corrosion:	0.04
Eye Irritation:	0.073
Respiratory Toxicity:	0.887

Download Data

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

Natural Product: NPC51358

Natural Product ID:	NPC51358
*Common Name:**	Sequoiatone E
IUPAC Name:	methyl (6E,7R)-7-hydroxy-6-[(3S)-9-hydroxy-3-methyl-2-oxononylidene]-1,7-dimethylcyclopenta[c]pyran-5-carboxylate
Synonyms:	Sequoiatone E
Standard InCHIKey:	BJRVUWKADRHSIV-TVXHFNGESA-N
Standard InCHI:	InChI=1S/C22H30O6/c1-14(9-7-5-6-8-11-23)18(24)13-17-19(21(25)27-4)16-10-12-28-15(2)20(16)22(17,3)26/h10,12-14,23,26H,5-9,11H2,1-4H3/b17-13+/t14-,22+/m0/s1
SMILES:	OCCCCCC[C@@H](C(=O)/C=C/1C(=C2C(=C(C)OC=C2)[C@]1(C)O)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495444
PubChem CID:	10872842
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678666]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027772]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15184162]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22103394]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24738739]
NPO23190	Aspergillus parasiticus	Species	Aspergillaceae	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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LD50	=	640.0	uM	PMID[571150]

☑ 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 NPC51358 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	177
0.1-0.2	996
0.2-0.3	4182
0.3-0.4	9099
0.4-0.5	17057
0.5-0.6	7257
0.6-0.7	3369
0.7-0.8	552
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC26078
0.9762	High Similarity	NPC307092
0.9643	High Similarity	NPC473658
0.8118	Intermediate Similarity	NPC316324
0.7912	Intermediate Similarity	NPC315395
0.7912	Intermediate Similarity	NPC234038
0.7912	Intermediate Similarity	NPC316426
0.7907	Intermediate Similarity	NPC315394
0.7849	Intermediate Similarity	NPC212598
0.7826	Intermediate Similarity	NPC72513
0.7816	Intermediate Similarity	NPC315765
0.7778	Intermediate Similarity	NPC16488
0.7767	Intermediate Similarity	NPC228477
0.7767	Intermediate Similarity	NPC137911
0.7717	Intermediate Similarity	NPC475461
0.7717	Intermediate Similarity	NPC305475
0.7717	Intermediate Similarity	NPC116575
0.77	Intermediate Similarity	NPC189609
0.77	Intermediate Similarity	NPC197835
0.77	Intermediate Similarity	NPC291500
0.77	Intermediate Similarity	NPC303653
0.77	Intermediate Similarity	NPC140591
0.7692	Intermediate Similarity	NPC96259
0.7692	Intermediate Similarity	NPC196487
0.7692	Intermediate Similarity	NPC141193
0.7692	Intermediate Similarity	NPC14575
0.766	Intermediate Similarity	NPC268298
0.7653	Intermediate Similarity	NPC208094
0.7629	Intermediate Similarity	NPC91408
0.7629	Intermediate Similarity	NPC304886
0.7614	Intermediate Similarity	NPC267231
0.7614	Intermediate Similarity	NPC93763
0.7614	Intermediate Similarity	NPC108816
0.7614	Intermediate Similarity	NPC192006
0.7609	Intermediate Similarity	NPC261380
0.7609	Intermediate Similarity	NPC165162
0.7609	Intermediate Similarity	NPC255307
0.7604	Intermediate Similarity	NPC476049
0.76	Intermediate Similarity	NPC469657
0.76	Intermediate Similarity	NPC244456
0.76	Intermediate Similarity	NPC469851
0.7582	Intermediate Similarity	NPC169575
0.7582	Intermediate Similarity	NPC40746
0.7579	Intermediate Similarity	NPC129419
0.7579	Intermediate Similarity	NPC475855
0.7579	Intermediate Similarity	NPC166554
0.7579	Intermediate Similarity	NPC179394
0.7579	Intermediate Similarity	NPC265856
0.7579	Intermediate Similarity	NPC144133
0.7573	Intermediate Similarity	NPC469853
0.7558	Intermediate Similarity	NPC227396
0.7556	Intermediate Similarity	NPC325031
0.7556	Intermediate Similarity	NPC112868
0.7549	Intermediate Similarity	NPC309190
0.7526	Intermediate Similarity	NPC53685
0.75	Intermediate Similarity	NPC320630
0.75	Intermediate Similarity	NPC116177
0.75	Intermediate Similarity	NPC300312
0.75	Intermediate Similarity	NPC261607
0.75	Intermediate Similarity	NPC166110
0.75	Intermediate Similarity	NPC476804
0.75	Intermediate Similarity	NPC114979
0.75	Intermediate Similarity	NPC7563
0.75	Intermediate Similarity	NPC191476
0.75	Intermediate Similarity	NPC111114
0.7476	Intermediate Similarity	NPC469852
0.7474	Intermediate Similarity	NPC115179
0.7474	Intermediate Similarity	NPC106040
0.7473	Intermediate Similarity	NPC474252
0.7473	Intermediate Similarity	NPC85772
0.7449	Intermediate Similarity	NPC295347
0.7449	Intermediate Similarity	NPC272050
0.7449	Intermediate Similarity	NPC209355
0.7447	Intermediate Similarity	NPC476079
0.7447	Intermediate Similarity	NPC113370
0.7447	Intermediate Similarity	NPC237540
0.7447	Intermediate Similarity	NPC160138
0.7447	Intermediate Similarity	NPC103743
0.7429	Intermediate Similarity	NPC47951
0.7423	Intermediate Similarity	NPC475838
0.7423	Intermediate Similarity	NPC228451
0.7423	Intermediate Similarity	NPC248193
0.7423	Intermediate Similarity	NPC125674
0.7419	Intermediate Similarity	NPC125290
0.7419	Intermediate Similarity	NPC471223
0.7419	Intermediate Similarity	NPC307112
0.7419	Intermediate Similarity	NPC67081
0.7419	Intermediate Similarity	NPC474369
0.7419	Intermediate Similarity	NPC470755
0.7412	Intermediate Similarity	NPC315285
0.7412	Intermediate Similarity	NPC316029
0.7412	Intermediate Similarity	NPC315597
0.74	Intermediate Similarity	NPC141191
0.7396	Intermediate Similarity	NPC145666
0.7396	Intermediate Similarity	NPC3436
0.7396	Intermediate Similarity	NPC77337
0.7396	Intermediate Similarity	NPC473448
0.7391	Intermediate Similarity	NPC250315
0.7391	Intermediate Similarity	NPC473390
0.7391	Intermediate Similarity	NPC131669
0.7383	Intermediate Similarity	NPC123855
0.7383	Intermediate Similarity	NPC76550
0.7383	Intermediate Similarity	NPC66108
0.7383	Intermediate Similarity	NPC138757
0.7368	Intermediate Similarity	NPC260343
0.7368	Intermediate Similarity	NPC476805
0.7368	Intermediate Similarity	NPC60765
0.7368	Intermediate Similarity	NPC475819
0.7363	Intermediate Similarity	NPC52861
0.7363	Intermediate Similarity	NPC42470
0.7363	Intermediate Similarity	NPC24417
0.7356	Intermediate Similarity	NPC470686
0.7353	Intermediate Similarity	NPC235369
0.7347	Intermediate Similarity	NPC167219
0.7347	Intermediate Similarity	NPC65829
0.7347	Intermediate Similarity	NPC198853
0.7347	Intermediate Similarity	NPC323008
0.7347	Intermediate Similarity	NPC477131
0.7347	Intermediate Similarity	NPC470010
0.7347	Intermediate Similarity	NPC470013
0.7347	Intermediate Similarity	NPC262133
0.7347	Intermediate Similarity	NPC474247
0.734	Intermediate Similarity	NPC122502
0.734	Intermediate Similarity	NPC198314
0.734	Intermediate Similarity	NPC261721
0.734	Intermediate Similarity	NPC150755
0.734	Intermediate Similarity	NPC164393
0.7333	Intermediate Similarity	NPC264227
0.7333	Intermediate Similarity	NPC63649
0.7333	Intermediate Similarity	NPC220155
0.7333	Intermediate Similarity	NPC472965
0.732	Intermediate Similarity	NPC32944
0.732	Intermediate Similarity	NPC193396
0.732	Intermediate Similarity	NPC470520
0.7315	Intermediate Similarity	NPC46269
0.7315	Intermediate Similarity	NPC106395
0.7312	Intermediate Similarity	NPC158756
0.7312	Intermediate Similarity	NPC470918
0.7312	Intermediate Similarity	NPC31086
0.7312	Intermediate Similarity	NPC70424
0.7312	Intermediate Similarity	NPC243618
0.7312	Intermediate Similarity	NPC82297
0.7308	Intermediate Similarity	NPC189863
0.7308	Intermediate Similarity	NPC478208
0.7303	Intermediate Similarity	NPC86917
0.73	Intermediate Similarity	NPC69385
0.73	Intermediate Similarity	NPC169205
0.73	Intermediate Similarity	NPC53844
0.73	Intermediate Similarity	NPC20066
0.7294	Intermediate Similarity	NPC236208
0.7292	Intermediate Similarity	NPC36668
0.7292	Intermediate Similarity	NPC142159
0.7292	Intermediate Similarity	NPC225283
0.7292	Intermediate Similarity	NPC218927
0.7292	Intermediate Similarity	NPC212664
0.7292	Intermediate Similarity	NPC118011
0.7292	Intermediate Similarity	NPC295312
0.7292	Intermediate Similarity	NPC95364
0.7292	Intermediate Similarity	NPC206001
0.7283	Intermediate Similarity	NPC229825
0.7283	Intermediate Similarity	NPC89555
0.7283	Intermediate Similarity	NPC7414
0.7282	Intermediate Similarity	NPC271059
0.7282	Intermediate Similarity	NPC25666
0.7273	Intermediate Similarity	NPC20546
0.7263	Intermediate Similarity	NPC142583
0.7263	Intermediate Similarity	NPC472007
0.7263	Intermediate Similarity	NPC312561
0.7255	Intermediate Similarity	NPC206079
0.7253	Intermediate Similarity	NPC160582
0.7248	Intermediate Similarity	NPC133677
0.7248	Intermediate Similarity	NPC138303
0.7248	Intermediate Similarity	NPC67290
0.7245	Intermediate Similarity	NPC288240
0.7245	Intermediate Similarity	NPC273579
0.7245	Intermediate Similarity	NPC282644
0.7245	Intermediate Similarity	NPC162205
0.7245	Intermediate Similarity	NPC295204
0.7245	Intermediate Similarity	NPC1108
0.7245	Intermediate Similarity	NPC29798
0.7245	Intermediate Similarity	NPC469692
0.7245	Intermediate Similarity	NPC59646
0.7245	Intermediate Similarity	NPC469645
0.7245	Intermediate Similarity	NPC475912
0.7241	Intermediate Similarity	NPC238948
0.7241	Intermediate Similarity	NPC12815
0.7241	Intermediate Similarity	NPC215745
0.7234	Intermediate Similarity	NPC471185
0.7234	Intermediate Similarity	NPC78089
0.7234	Intermediate Similarity	NPC28887
0.7228	Intermediate Similarity	NPC166770
0.7228	Intermediate Similarity	NPC316598
0.7228	Intermediate Similarity	NPC35717
0.7228	Intermediate Similarity	NPC203627
0.7228	Intermediate Similarity	NPC64742
0.7228	Intermediate Similarity	NPC222011
0.7228	Intermediate Similarity	NPC300584
0.7222	Intermediate Similarity	NPC196653
0.7222	Intermediate Similarity	NPC128276
0.7222	Intermediate Similarity	NPC471465

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 NPC51358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1379
0.2-0.3	3484
0.3-0.4	2661
0.4-0.5	1047
0.5-0.6	349
0.6-0.7	68
0.7-0.8	6
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
0.7778	Intermediate Similarity	NPD7154	Phase 3
0.7582	Intermediate Similarity	NPD5362	Discontinued
0.7579	Intermediate Similarity	NPD5785	Approved
0.7419	Intermediate Similarity	NPD5363	Approved
0.7303	Intermediate Similarity	NPD4756	Discovery
0.7283	Intermediate Similarity	NPD4270	Approved
0.7283	Intermediate Similarity	NPD4269	Approved
0.7174	Intermediate Similarity	NPD5369	Approved
0.7158	Intermediate Similarity	NPD5786	Approved
0.71	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4252	Approved
0.7065	Intermediate Similarity	NPD4822	Approved
0.7065	Intermediate Similarity	NPD4819	Approved
0.7065	Intermediate Similarity	NPD4820	Approved
0.7065	Intermediate Similarity	NPD4821	Approved
0.7059	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6698	Approved
0.7041	Intermediate Similarity	NPD46	Approved
0.7037	Intermediate Similarity	NPD6371	Approved
0.7033	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5281	Approved
0.697	Remote Similarity	NPD5284	Approved
0.6909	Remote Similarity	NPD6053	Discontinued
0.6882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4271	Approved
0.6848	Remote Similarity	NPD4268	Approved
0.6842	Remote Similarity	NPD5331	Approved
0.6842	Remote Similarity	NPD5332	Approved
0.6832	Remote Similarity	NPD5282	Discontinued
0.6809	Remote Similarity	NPD4790	Discontinued
0.6804	Remote Similarity	NPD4249	Approved
0.68	Remote Similarity	NPD7983	Approved
0.6737	Remote Similarity	NPD5209	Approved
0.6737	Remote Similarity	NPD6435	Approved
0.6735	Remote Similarity	NPD4250	Approved
0.6735	Remote Similarity	NPD4251	Approved
0.6733	Remote Similarity	NPD5778	Approved
0.6733	Remote Similarity	NPD5779	Approved
0.6703	Remote Similarity	NPD8039	Approved
0.6702	Remote Similarity	NPD5368	Approved
0.6701	Remote Similarity	NPD1694	Approved
0.67	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD7115	Discovery
0.6606	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1695	Approved
0.6562	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3704	Approved
0.6538	Remote Similarity	NPD7839	Suspended
0.6531	Remote Similarity	NPD1696	Phase 3
0.6518	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6084	Phase 2
0.6476	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7637	Suspended
0.6442	Remote Similarity	NPD5695	Phase 3
0.6436	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6101	Approved
0.6436	Remote Similarity	NPD5370	Suspended
0.6429	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5696	Approved
0.6415	Remote Similarity	NPD4225	Approved
0.6408	Remote Similarity	NPD6399	Phase 3
0.6392	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5207	Approved
0.6364	Remote Similarity	NPD7331	Phase 2
0.6355	Remote Similarity	NPD7639	Approved
0.6355	Remote Similarity	NPD7640	Approved
0.6337	Remote Similarity	NPD4518	Approved
0.633	Remote Similarity	NPD6647	Phase 2
0.6311	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD5694	Approved
0.6311	Remote Similarity	NPD5693	Phase 1
0.6306	Remote Similarity	NPD5697	Approved
0.6303	Remote Similarity	NPD8513	Phase 3
0.63	Remote Similarity	NPD4519	Discontinued
0.63	Remote Similarity	NPD5279	Phase 3
0.63	Remote Similarity	NPD4623	Approved
0.6286	Remote Similarity	NPD4629	Approved
0.6286	Remote Similarity	NPD5210	Approved
0.6283	Remote Similarity	NPD2067	Discontinued
0.6275	Remote Similarity	NPD4753	Phase 2
0.6275	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5909	Discontinued
0.6262	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7341	Phase 2
0.625	Remote Similarity	NPD6899	Approved
0.6239	Remote Similarity	NPD5211	Phase 2
0.6228	Remote Similarity	NPD6650	Approved
0.6228	Remote Similarity	NPD6649	Approved
0.6228	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6675	Approved
0.6216	Remote Similarity	NPD7128	Approved
0.6216	Remote Similarity	NPD5739	Approved
0.6216	Remote Similarity	NPD6402	Approved
0.6214	Remote Similarity	NPD5692	Phase 3
0.6207	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6648	Approved
0.62	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6372	Approved
0.6195	Remote Similarity	NPD6014	Approved
0.6195	Remote Similarity	NPD6013	Approved
0.6195	Remote Similarity	NPD6373	Approved
0.6195	Remote Similarity	NPD6012	Approved
0.6186	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD8516	Approved
0.6167	Remote Similarity	NPD8517	Approved
0.6167	Remote Similarity	NPD8515	Approved
0.6163	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6110	Phase 1
0.6161	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD6050	Approved
0.6147	Remote Similarity	NPD5344	Discontinued
0.6146	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6883	Approved
0.614	Remote Similarity	NPD7290	Approved
0.614	Remote Similarity	NPD7102	Approved
0.6139	Remote Similarity	NPD4694	Approved
0.6139	Remote Similarity	NPD5280	Approved
0.6126	Remote Similarity	NPD5141	Approved
0.6111	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6686	Approved
0.6106	Remote Similarity	NPD7320	Approved
0.61	Remote Similarity	NPD3666	Approved
0.61	Remote Similarity	NPD3665	Phase 1
0.61	Remote Similarity	NPD3133	Approved
0.6095	Remote Similarity	NPD4202	Approved
0.6087	Remote Similarity	NPD8130	Phase 1
0.6087	Remote Similarity	NPD6617	Approved
0.6087	Remote Similarity	NPD6847	Approved
0.6087	Remote Similarity	NPD6869	Approved
0.6061	Remote Similarity	NPD4223	Phase 3
0.6061	Remote Similarity	NPD4221	Approved
0.6055	Remote Similarity	NPD5286	Approved
0.6055	Remote Similarity	NPD5285	Approved
0.6055	Remote Similarity	NPD4696	Approved
0.6034	Remote Similarity	NPD8297	Approved
0.6034	Remote Similarity	NPD6882	Approved
0.6033	Remote Similarity	NPD7503	Approved
0.602	Remote Similarity	NPD4695	Discontinued
0.602	Remote Similarity	NPD7332	Phase 2
0.6019	Remote Similarity	NPD7902	Approved
0.6019	Remote Similarity	NPD5737	Approved
0.6019	Remote Similarity	NPD4755	Approved
0.6019	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4632	Approved
0.5981	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5654	Approved
0.598	Remote Similarity	NPD7334	Approved
0.598	Remote Similarity	NPD6409	Approved
0.598	Remote Similarity	NPD5330	Approved
0.598	Remote Similarity	NPD5690	Phase 2
0.598	Remote Similarity	NPD6684	Approved
0.598	Remote Similarity	NPD7521	Approved
0.598	Remote Similarity	NPD7146	Approved
0.598	Remote Similarity	NPD3618	Phase 1
0.5966	Remote Similarity	NPD7500	Approved
0.5962	Remote Similarity	NPD6673	Approved
0.5962	Remote Similarity	NPD6080	Approved
0.5962	Remote Similarity	NPD6904	Approved
0.595	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4633	Approved
0.5946	Remote Similarity	NPD5224	Approved
0.5946	Remote Similarity	NPD5225	Approved
0.5946	Remote Similarity	NPD5226	Approved
0.5946	Remote Similarity	NPD7632	Discontinued
0.5941	Remote Similarity	NPD4786	Approved
0.5941	Remote Similarity	NPD4197	Approved
0.5941	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6008	Approved
0.592	Remote Similarity	NPD8074	Phase 3
0.5913	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4194	Approved
0.5909	Remote Similarity	NPD4193	Approved
0.5909	Remote Similarity	NPD4192	Approved
0.5909	Remote Similarity	NPD4191	Approved
0.5909	Remote Similarity	NPD4700	Approved
0.5905	Remote Similarity	NPD4096	Approved
0.59	Remote Similarity	NPD3667	Approved
0.5893	Remote Similarity	NPD5174	Approved
0.5893	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5175	Approved
0.5888	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7748	Approved
0.5882	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5329	Approved
0.5872	Remote Similarity	NPD5959	Approved
0.5865	Remote Similarity	NPD5208	Approved
0.5865	Remote Similarity	NPD6903	Approved
0.5865	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7514	Phase 3
0.5859	Remote Similarity	NPD7260	Phase 2

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