NPASS Compound

Structure

NPC474725 OpenBabel07101718202D 31 33 0 0 1 0 0 0 0 0999 V2000 2.8640 -0.5050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2136 1.1393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9430 -4.6871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8482 -2.9920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8482 -1.0508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5457 0.4041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0418 -3.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7753 -2.9527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6147 0.6198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1982 -3.3232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1671 -2.9920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0811 -0.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5641 0.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0811 -3.7264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0076 -2.5067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0076 -1.5361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3265 -2.5067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9653 -0.1015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0488 -2.0214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0418 -0.4545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1982 -0.7196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1671 -1.0508 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7753 -1.0901 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3948 -0.8867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3265 -1.5361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0194 -2.0214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4450 0.4283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0730 0.7474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3442 -1.0885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5918 -0.5654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 6 31 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 15 16 1 0 0 0 0 16 5 1 6 0 0 0 16 22 1 0 0 0 0 17 25 1 6 0 0 0 18 9 1 1 0 0 0 18 22 1 0 0 0 0 18 26 1 0 0 0 0 19 23 1 0 0 0 0 19 27 1 6 0 0 0 20 23 1 0 0 0 0 20 28 1 1 0 0 0 21 29 2 0 0 0 0 22 25 1 6 0 0 0 23 31 1 6 0 0 0 24 25 1 0 0 0 0 24 26 2 0 0 0 0 24 30 1 0 0 0 0 25 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	433.28
Volume:	459.689
LogP:	3.433
LogD:	3.78
LogS:	-4.11
# Rotatable Bonds:	3
TPSA:	95.86
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	5.935
Fsp3:	0.76
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:	-4.856
MDCK Permeability:	1.9991248336737044e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.882
20% Bioavailability (F20%):	0.873
30% Bioavailability (F30%):	0.573

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.852
Plasma Protein Binding (PPB):	86.72530364990234%
Volume Distribution (VD):	1.017
Pgp-substrate:	8.264862060546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.182
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.479
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	13.313
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.152
Rat Oral Acute Toxicity:	0.883
Maximum Recommended Daily Dose:	0.479
Skin Sensitization:	0.393
Carcinogencity:	0.519
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC474725

Natural Product ID:	NPC474725
*Common Name:**	Aspochalasin K
IUPAC Name:	n.a.
Synonyms:	aspochalasin K
Standard InCHIKey:	VDFBOYQHOXIVOC-LJICDNDHSA-N
Standard InCHI:	InChI=1S/C25H39NO5/c1-13(2)9-18-22-16(5)15(4)11-17-10-14(3)7-8-19(27)23(31-6)20(28)12-21(29)25(17,22)24(30)26-18/h10-11,13,16-20,22-23,27-28H,7-9,12H2,1-6H3,(H,26,30)/b14-10+/t16-,17+,18+,19+,20+,22+,23+,25-/m1/s1
SMILES:	CO[C@H]1[C@@H](O)CC/C(=C/[C@@H]2[C@]3(C(=O)C[C@@H]1O)C(=N[C@H]([C@@H]3[C@@H](C(=C2)C)C)CC(C)C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480485
PubChem CID:	44575563
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001821] Cytochalasans [CHEMONTID:0003768] Aspochalasins

*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
NPO28935	Ericameria laricifolia	Species	Asteraceae	Eukaryota	n.a.	Sonoran Desert	n.a.	PMID[15043404]
NPO28935	Ericameria laricifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	14300.0	nM	PMID[533632]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	13100.0	nM	PMID[533632]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	19900.0	nM	PMID[533632]

☑ 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 NPC474725 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	87
0.1-0.2	572
0.2-0.3	3641
0.3-0.4	19606
0.4-0.5	10519
0.5-0.6	7744
0.6-0.7	498
0.7-0.8	23
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC475800
0.8426	Intermediate Similarity	NPC307903
0.8426	Intermediate Similarity	NPC140251
0.8224	Intermediate Similarity	NPC474563
0.7692	Intermediate Similarity	NPC476190
0.7652	Intermediate Similarity	NPC476269
0.7478	Intermediate Similarity	NPC476290
0.7455	Intermediate Similarity	NPC473224
0.7364	Intermediate Similarity	NPC234542
0.7328	Intermediate Similarity	NPC46764
0.7281	Intermediate Similarity	NPC473252
0.7273	Intermediate Similarity	NPC27105
0.7273	Intermediate Similarity	NPC323532
0.7207	Intermediate Similarity	NPC471331
0.7207	Intermediate Similarity	NPC472687
0.7207	Intermediate Similarity	NPC203388
0.7207	Intermediate Similarity	NPC99657
0.7207	Intermediate Similarity	NPC471330
0.7203	Intermediate Similarity	NPC7797
0.7193	Intermediate Similarity	NPC14537
0.7188	Intermediate Similarity	NPC139585
0.7182	Intermediate Similarity	NPC472734
0.7182	Intermediate Similarity	NPC472733
0.717	Intermediate Similarity	NPC34754
0.7143	Intermediate Similarity	NPC204556
0.713	Intermediate Similarity	NPC471333
0.713	Intermediate Similarity	NPC471332
0.7117	Intermediate Similarity	NPC472732
0.7117	Intermediate Similarity	NPC472731
0.7107	Intermediate Similarity	NPC201968
0.7105	Intermediate Similarity	NPC98765
0.7083	Intermediate Similarity	NPC476814
0.7083	Intermediate Similarity	NPC476813
0.7083	Intermediate Similarity	NPC50694
0.7054	Intermediate Similarity	NPC177680
0.7054	Intermediate Similarity	NPC153776
0.7054	Intermediate Similarity	NPC472730
0.7054	Intermediate Similarity	NPC472729
0.7043	Intermediate Similarity	NPC119329
0.7037	Intermediate Similarity	NPC803
0.7034	Intermediate Similarity	NPC113012
0.7034	Intermediate Similarity	NPC122926
0.7009	Intermediate Similarity	NPC70235
0.7	Intermediate Similarity	NPC469819
0.7	Intermediate Similarity	NPC106479
0.7	Intermediate Similarity	NPC114162
0.6991	Remote Similarity	NPC472728
0.6991	Remote Similarity	NPC472727
0.6972	Remote Similarity	NPC314500
0.697	Remote Similarity	NPC145899
0.6967	Remote Similarity	NPC216335
0.6964	Remote Similarity	NPC4834
0.6957	Remote Similarity	NPC117185
0.6957	Remote Similarity	NPC215988
0.6949	Remote Similarity	NPC470257
0.6947	Remote Similarity	NPC76999
0.6894	Remote Similarity	NPC75318
0.6889	Remote Similarity	NPC172365
0.6889	Remote Similarity	NPC82931
0.6889	Remote Similarity	NPC210729
0.6875	Remote Similarity	NPC8803
0.687	Remote Similarity	NPC469598
0.6866	Remote Similarity	NPC200788
0.6866	Remote Similarity	NPC243680
0.6829	Remote Similarity	NPC147707
0.681	Remote Similarity	NPC475321
0.6803	Remote Similarity	NPC470540
0.6794	Remote Similarity	NPC475472
0.6794	Remote Similarity	NPC116057
0.6783	Remote Similarity	NPC476134
0.6783	Remote Similarity	NPC101067
0.6783	Remote Similarity	NPC77703
0.678	Remote Similarity	NPC43285
0.678	Remote Similarity	NPC58370
0.6774	Remote Similarity	NPC471118
0.6774	Remote Similarity	NPC9714
0.6774	Remote Similarity	NPC471121
0.6772	Remote Similarity	NPC280498
0.6769	Remote Similarity	NPC471471
0.6769	Remote Similarity	NPC164476
0.6769	Remote Similarity	NPC121601
0.6762	Remote Similarity	NPC212083
0.6759	Remote Similarity	NPC90652
0.6752	Remote Similarity	NPC471293
0.6752	Remote Similarity	NPC472616
0.6752	Remote Similarity	NPC259476
0.6752	Remote Similarity	NPC470104
0.6752	Remote Similarity	NPC255309
0.6742	Remote Similarity	NPC119794
0.6742	Remote Similarity	NPC73829
0.6739	Remote Similarity	NPC475892
0.6726	Remote Similarity	NPC135576
0.6726	Remote Similarity	NPC93271
0.6726	Remote Similarity	NPC49371
0.6726	Remote Similarity	NPC123141
0.6723	Remote Similarity	NPC475150
0.672	Remote Similarity	NPC35037
0.6718	Remote Similarity	NPC201359
0.6697	Remote Similarity	NPC476706
0.6697	Remote Similarity	NPC470417
0.6697	Remote Similarity	NPC476707
0.6696	Remote Similarity	NPC167974
0.6696	Remote Similarity	NPC473172
0.6696	Remote Similarity	NPC174051
0.6696	Remote Similarity	NPC67831
0.6695	Remote Similarity	NPC96377
0.6694	Remote Similarity	NPC12270
0.6694	Remote Similarity	NPC471117
0.6694	Remote Similarity	NPC471120
0.6694	Remote Similarity	NPC471243
0.6692	Remote Similarity	NPC477352
0.6692	Remote Similarity	NPC329919
0.6692	Remote Similarity	NPC477793
0.6691	Remote Similarity	NPC208725
0.6691	Remote Similarity	NPC180770
0.6691	Remote Similarity	NPC302276
0.6667	Remote Similarity	NPC191892
0.6667	Remote Similarity	NPC472413
0.6667	Remote Similarity	NPC69171
0.6667	Remote Similarity	NPC239895
0.6667	Remote Similarity	NPC262870
0.6667	Remote Similarity	NPC473898
0.6667	Remote Similarity	NPC474165
0.6667	Remote Similarity	NPC475584
0.6667	Remote Similarity	NPC475152
0.6667	Remote Similarity	NPC473578
0.6667	Remote Similarity	NPC124246
0.6667	Remote Similarity	NPC475394
0.6642	Remote Similarity	NPC280941
0.6642	Remote Similarity	NPC235772
0.6639	Remote Similarity	NPC169375
0.6637	Remote Similarity	NPC473170
0.6637	Remote Similarity	NPC248574
0.6637	Remote Similarity	NPC108141
0.6612	Remote Similarity	NPC92829
0.661	Remote Similarity	NPC475036
0.661	Remote Similarity	NPC475239
0.6609	Remote Similarity	NPC469565
0.6606	Remote Similarity	NPC298904
0.6602	Remote Similarity	NPC325946
0.6594	Remote Similarity	NPC162910
0.6589	Remote Similarity	NPC469494
0.6585	Remote Similarity	NPC194273
0.6583	Remote Similarity	NPC476276
0.6583	Remote Similarity	NPC473288
0.6581	Remote Similarity	NPC473928
0.6581	Remote Similarity	NPC476235
0.6581	Remote Similarity	NPC183571
0.6581	Remote Similarity	NPC283567
0.6581	Remote Similarity	NPC473163
0.6581	Remote Similarity	NPC476126
0.6579	Remote Similarity	NPC472675
0.6579	Remote Similarity	NPC21681
0.6579	Remote Similarity	NPC473164
0.6577	Remote Similarity	NPC289213
0.6571	Remote Similarity	NPC472948
0.6569	Remote Similarity	NPC265908
0.6569	Remote Similarity	NPC114236
0.6567	Remote Similarity	NPC183722
0.656	Remote Similarity	NPC188010
0.6557	Remote Similarity	NPC474229
0.6555	Remote Similarity	NPC271269
0.6555	Remote Similarity	NPC472615
0.6555	Remote Similarity	NPC210178
0.6555	Remote Similarity	NPC470587
0.6555	Remote Similarity	NPC102352
0.6552	Remote Similarity	NPC218383
0.6552	Remote Similarity	NPC110149
0.6552	Remote Similarity	NPC83709
0.6552	Remote Similarity	NPC474720
0.6549	Remote Similarity	NPC477241
0.6549	Remote Similarity	NPC103527
0.6549	Remote Similarity	NPC196227
0.6549	Remote Similarity	NPC473314
0.6545	Remote Similarity	NPC474854
0.6545	Remote Similarity	NPC476708
0.6545	Remote Similarity	NPC44181
0.6545	Remote Similarity	NPC53911
0.6542	Remote Similarity	NPC476082
0.6542	Remote Similarity	NPC278648
0.6532	Remote Similarity	NPC243354
0.6532	Remote Similarity	NPC247069
0.6532	Remote Similarity	NPC117712
0.6529	Remote Similarity	NPC87335
0.6529	Remote Similarity	NPC310546
0.6525	Remote Similarity	NPC471005
0.6525	Remote Similarity	NPC474583
0.6522	Remote Similarity	NPC53844
0.6522	Remote Similarity	NPC273269
0.6522	Remote Similarity	NPC272451
0.6522	Remote Similarity	NPC140300
0.6518	Remote Similarity	NPC116726
0.6518	Remote Similarity	NPC230623
0.6518	Remote Similarity	NPC475441
0.6518	Remote Similarity	NPC476705
0.6518	Remote Similarity	NPC19114
0.6514	Remote Similarity	NPC475753
0.6514	Remote Similarity	NPC473168
0.6514	Remote Similarity	NPC262026
0.6504	Remote Similarity	NPC469865

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 NPC474725 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	87
0.1-0.2	593
0.2-0.3	3495
0.3-0.4	3619
0.4-0.5	1001
0.5-0.6	334
0.6-0.7	21
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
0.7244	Intermediate Similarity	NPD6914	Discontinued
0.675	Remote Similarity	NPD6420	Discontinued
0.6694	Remote Similarity	NPD1719	Phase 1
0.6612	Remote Similarity	NPD6421	Discontinued
0.6496	Remote Similarity	NPD6333	Approved
0.6496	Remote Similarity	NPD6334	Approved
0.6372	Remote Similarity	NPD6411	Approved
0.6364	Remote Similarity	NPD6412	Phase 2
0.6341	Remote Similarity	NPD4634	Approved
0.6339	Remote Similarity	NPD5328	Approved
0.633	Remote Similarity	NPD4786	Approved
0.6316	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5779	Approved
0.6316	Remote Similarity	NPD5778	Approved
0.6299	Remote Similarity	NPD7500	Approved
0.6299	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7641	Discontinued
0.6241	Remote Similarity	NPD8074	Phase 3
0.6231	Remote Similarity	NPD6921	Approved
0.6231	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6079	Approved
0.6216	Remote Similarity	NPD3618	Phase 1
0.6195	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6101	Approved
0.6194	Remote Similarity	NPD8336	Approved
0.6194	Remote Similarity	NPD8337	Approved
0.6183	Remote Similarity	NPD8080	Discontinued
0.6182	Remote Similarity	NPD3133	Approved
0.6182	Remote Similarity	NPD3666	Approved
0.6182	Remote Similarity	NPD3665	Phase 1
0.6174	Remote Similarity	NPD6399	Phase 3
0.616	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6319	Approved
0.6154	Remote Similarity	NPD4697	Phase 3
0.6154	Remote Similarity	NPD6059	Approved
0.6154	Remote Similarity	NPD6054	Approved
0.6136	Remote Similarity	NPD8328	Phase 3
0.6121	Remote Similarity	NPD5282	Discontinued
0.6107	Remote Similarity	NPD6909	Approved
0.6107	Remote Similarity	NPD6908	Approved
0.6102	Remote Similarity	NPD4755	Approved
0.609	Remote Similarity	NPD8341	Approved
0.609	Remote Similarity	NPD8299	Approved
0.609	Remote Similarity	NPD8342	Approved
0.609	Remote Similarity	NPD8340	Approved
0.6087	Remote Similarity	NPD7983	Approved
0.6063	Remote Similarity	NPD4632	Approved
0.6061	Remote Similarity	NPD6370	Approved
0.6058	Remote Similarity	NPD7260	Phase 2
0.6053	Remote Similarity	NPD4753	Phase 2
0.6048	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6686	Approved
0.6047	Remote Similarity	NPD7115	Discovery
0.6045	Remote Similarity	NPD8451	Approved
0.6017	Remote Similarity	NPD5222	Approved
0.6017	Remote Similarity	NPD4228	Discovery
0.6017	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5221	Approved
0.6017	Remote Similarity	NPD7839	Suspended
0.6016	Remote Similarity	NPD7333	Discontinued
0.6016	Remote Similarity	NPD6640	Phase 3
0.6016	Remote Similarity	NPD6675	Approved
0.6016	Remote Similarity	NPD7128	Approved
0.6016	Remote Similarity	NPD6402	Approved
0.6016	Remote Similarity	NPD5739	Approved
0.6015	Remote Similarity	NPD7604	Phase 2
0.6015	Remote Similarity	NPD7642	Approved
0.6	Remote Similarity	NPD6404	Discontinued
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD8418	Phase 2
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5985	Remote Similarity	NPD8390	Approved
0.5985	Remote Similarity	NPD8392	Approved
0.5985	Remote Similarity	NPD8391	Approved
0.5985	Remote Similarity	NPD6015	Approved
0.5985	Remote Similarity	NPD6016	Approved
0.5985	Remote Similarity	NPD8444	Approved
0.5984	Remote Similarity	NPD8297	Approved
0.597	Remote Similarity	NPD7492	Approved
0.5966	Remote Similarity	NPD5173	Approved
0.5966	Remote Similarity	NPD6084	Phase 2
0.5966	Remote Similarity	NPD6083	Phase 2
0.5954	Remote Similarity	NPD7517	Approved
0.5954	Remote Similarity	NPD7518	Approved
0.5954	Remote Similarity	NPD7519	Approved
0.5952	Remote Similarity	NPD6371	Approved
0.5948	Remote Similarity	NPD7515	Phase 2
0.594	Remote Similarity	NPD5988	Approved
0.594	Remote Similarity	NPD7623	Phase 3
0.594	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4629	Approved
0.5932	Remote Similarity	NPD5210	Approved
0.5929	Remote Similarity	NPD8415	Approved
0.5929	Remote Similarity	NPD5786	Approved
0.5929	Remote Similarity	NPD5279	Phase 3
0.5929	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD8273	Phase 1
0.5926	Remote Similarity	NPD6616	Approved
0.5923	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.592	Remote Similarity	NPD6881	Approved
0.592	Remote Similarity	NPD7320	Approved
0.592	Remote Similarity	NPD6899	Approved
0.5917	Remote Similarity	NPD4225	Approved
0.5909	Remote Similarity	NPD857	Phase 3
0.5909	Remote Similarity	NPD5369	Approved
0.5906	Remote Similarity	NPD2204	Approved
0.5906	Remote Similarity	NPD6650	Approved
0.5906	Remote Similarity	NPD6649	Approved
0.5902	Remote Similarity	NPD5211	Phase 2
0.5902	Remote Similarity	NPD4633	Approved
0.5902	Remote Similarity	NPD5224	Approved
0.5902	Remote Similarity	NPD5225	Approved
0.5902	Remote Similarity	NPD5226	Approved
0.5899	Remote Similarity	NPD6845	Suspended
0.5893	Remote Similarity	NPD3668	Phase 3
0.5887	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5357	Phase 1
0.5882	Remote Similarity	NPD7078	Approved
0.5882	Remote Similarity	NPD8293	Discontinued
0.5873	Remote Similarity	NPD6413	Approved
0.5873	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD8269	Approved
0.5865	Remote Similarity	NPD8267	Approved
0.5865	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD8266	Approved
0.5865	Remote Similarity	NPD8268	Approved
0.5856	Remote Similarity	NPD6435	Approved
0.5856	Remote Similarity	NPD7345	Approved
0.5854	Remote Similarity	NPD5174	Approved
0.5854	Remote Similarity	NPD5175	Approved
0.5847	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD7748	Approved
0.584	Remote Similarity	NPD5701	Approved
0.584	Remote Similarity	NPD5697	Approved
0.5839	Remote Similarity	NPD7736	Approved
0.5833	Remote Similarity	NPD7902	Approved
0.5827	Remote Similarity	NPD7102	Approved
0.5827	Remote Similarity	NPD6883	Approved
0.5827	Remote Similarity	NPD7290	Approved
0.582	Remote Similarity	NPD5223	Approved
0.5818	Remote Similarity	NPD5368	Approved
0.5806	Remote Similarity	NPD5141	Approved
0.5804	Remote Similarity	NPD6110	Phase 1
0.5802	Remote Similarity	NPD6009	Approved
0.5798	Remote Similarity	NPD5695	Phase 3
0.5797	Remote Similarity	NPD7319	Approved
0.5789	Remote Similarity	NPD7147	Phase 3
0.5789	Remote Similarity	NPD7146	Approved
0.5789	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5330	Approved
0.5789	Remote Similarity	NPD6684	Approved
0.5789	Remote Similarity	NPD7521	Approved
0.5789	Remote Similarity	NPD7334	Approved
0.5789	Remote Similarity	NPD6409	Approved
0.5785	Remote Similarity	NPD5696	Approved
0.5781	Remote Similarity	NPD6847	Approved
0.5781	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD8130	Phase 1
0.5781	Remote Similarity	NPD6617	Approved
0.5781	Remote Similarity	NPD6869	Approved
0.578	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.578	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD7829	Approved
0.5778	Remote Similarity	NPD7830	Approved
0.5772	Remote Similarity	NPD8086	Approved
0.5772	Remote Similarity	NPD8082	Approved
0.5772	Remote Similarity	NPD8139	Approved
0.5772	Remote Similarity	NPD8083	Approved
0.5772	Remote Similarity	NPD8085	Approved
0.5772	Remote Similarity	NPD8138	Approved
0.5772	Remote Similarity	NPD8084	Approved
0.5766	Remote Similarity	NPD7746	Phase 1
0.5766	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7747	Phase 1
0.5763	Remote Similarity	NPD4202	Approved
0.576	Remote Similarity	NPD4768	Approved
0.576	Remote Similarity	NPD4767	Approved
0.576	Remote Similarity	NPD4211	Phase 1
0.5748	Remote Similarity	NPD6012	Approved
0.5748	Remote Similarity	NPD6013	Approved
0.5748	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD6014	Approved
0.5739	Remote Similarity	NPD7524	Approved
0.5736	Remote Similarity	NPD6882	Approved
0.5726	Remote Similarity	NPD8275	Approved
0.5726	Remote Similarity	NPD4754	Approved
0.5726	Remote Similarity	NPD5785	Approved
0.5726	Remote Similarity	NPD8276	Approved
0.5726	Remote Similarity	NPD6698	Approved
0.5726	Remote Similarity	NPD46	Approved
0.5725	Remote Similarity	NPD6033	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