NPASS Compound

Structure

NPC471569 OpenBabel07101718192D 38 40 0 0 1 0 0 0 0 0999 V2000 2.9731 -10.8194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5664 -9.9058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1542 -9.0968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7475 -8.1833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3352 -7.3742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9285 -6.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5163 -5.6517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1096 -4.7381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6973 -3.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2906 -3.0156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2961 -2.9110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8893 -1.9975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4771 -1.1885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6582 0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2569 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4215 2.9611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0203 3.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 -0.2749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2514 1.4476 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4161 2.8566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4325 3.1702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8228 1.9431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0038 3.6656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4380 3.2747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0148 3.8747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8392 2.2567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0759 -0.1704 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 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 14 16 2 0 0 0 0 14 24 1 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 29 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 29 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 21 30 1 0 0 0 0 22 27 1 0 0 0 0 22 35 1 0 0 0 0 23 28 1 0 0 0 0 23 35 1 0 0 0 0 24 31 2 0 0 0 0 25 13 1 1 0 0 0 25 37 1 0 0 0 0 26 36 1 6 0 0 0 27 32 2 0 0 0 0 27 33 1 0 0 0 0 28 34 2 0 0 0 0 28 36 1 0 0 0 0 29 38 1 0 0 0 0 30 19 1 1 0 0 0 30 37 1 0 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.32
Volume:	558.906
LogP:	5.515
LogD:	2.735
LogS:	-5.276
# Rotatable Bonds:	18
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.184
Synthetic Accessibility Score:	4.896
Fsp3:	0.767
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.12
MDCK Permeability:	5.407119169831276e-05
Pgp-inhibitor:	0.101
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187
Plasma Protein Binding (PPB):	98.48070526123047%
Volume Distribution (VD):	1.627
Pgp-substrate:	0.9467933177947998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.512
CYP2C19-substrate:	0.381
CYP2C9-inhibitor:	0.587
CYP2C9-substrate:	0.163
CYP2D6-inhibitor:	0.067
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.518
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	5.908
Half-life (T1/2):	0.784

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.759
Drug-inuced Liver Injury (DILI):	0.726
AMES Toxicity:	0.696
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.976
Carcinogencity:	0.801
Eye Corrosion:	0.753
Eye Irritation:	0.647
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC471569

Natural Product ID:	NPC471569
*Common Name:**	((2R,4R,6R)-11-Oxo-2-Tridecyl-1,7-Dioxa-Dispiro[5.1.5.2]Pentadeca-9,12-Dien-4-Yloxycarbonylmethoxy)-Acetic Acid
IUPAC Name:	2-[2-oxo-2-[[(2R,4R,6R)-11-oxo-4-tridecyl-5,7-dioxadispiro[5.1.5^{8}.2^{6}]pentadeca-9,12-dien-2-yl]oxy]ethoxy]acetic acid
Synonyms:
Standard InCHIKey:	WAGIIXLZRNZTQB-VOKYQHOCSA-N
Standard InCHI:	InChI=1S/C30H46O8/c1-2-3-4-5-6-7-8-9-10-11-12-13-25-20-26(36-28(34)23-35-22-27(32)33)21-30(37-25)19-18-29(38-30)16-14-24(31)15-17-29/h14-17,25-26H,2-13,18-23H2,1H3,(H,32,33)/t25-,26-,30-/m1/s1
SMILES:	CCCCCCCCCCCCC[C@@H]1C[C@@H](OC(=O)COCC(=O)O)C[C@@]2(O1)CCC1(O2)C=CC(=O)C=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL258232
PubChem CID:	24853602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	3.4	uM	PMID[567755]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	1.9	uM	PMID[567755]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	1.3	uM	PMID[567755]

☑ 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 NPC471569 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	169
0.1-0.2	1318
0.2-0.3	5560
0.3-0.4	12917
0.4-0.5	11506
0.5-0.6	7730
0.6-0.7	3244
0.7-0.8	244
0.8-0.85	1
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8929	High Similarity	NPC473339
0.8929	High Similarity	NPC471552
0.8721	High Similarity	NPC27314
0.8721	High Similarity	NPC106912
0.8721	High Similarity	NPC2379
0.8721	High Similarity	NPC31019
0.8721	High Similarity	NPC263087
0.8191	Intermediate Similarity	NPC256368
0.814	Intermediate Similarity	NPC326753
0.8125	Intermediate Similarity	NPC266842
0.7912	Intermediate Similarity	NPC473353
0.7872	Intermediate Similarity	NPC177668
0.7872	Intermediate Similarity	NPC202886
0.7865	Intermediate Similarity	NPC469469
0.7835	Intermediate Similarity	NPC173329
0.7835	Intermediate Similarity	NPC288350
0.7822	Intermediate Similarity	NPC472748
0.7789	Intermediate Similarity	NPC477749
0.7766	Intermediate Similarity	NPC133450
0.7766	Intermediate Similarity	NPC477748
0.7745	Intermediate Similarity	NPC472749
0.7745	Intermediate Similarity	NPC472751
0.7723	Intermediate Similarity	NPC472750
0.7723	Intermediate Similarity	NPC472747
0.7717	Intermediate Similarity	NPC471494
0.7708	Intermediate Similarity	NPC472195
0.7708	Intermediate Similarity	NPC238090
0.7708	Intermediate Similarity	NPC472196
0.7677	Intermediate Similarity	NPC203627
0.7634	Intermediate Similarity	NPC311163
0.7634	Intermediate Similarity	NPC208473
0.7629	Intermediate Similarity	NPC159698
0.7609	Intermediate Similarity	NPC475035
0.7609	Intermediate Similarity	NPC266718
0.7573	Intermediate Similarity	NPC239961
0.7553	Intermediate Similarity	NPC475037
0.7526	Intermediate Similarity	NPC471483
0.7525	Intermediate Similarity	NPC471637
0.7525	Intermediate Similarity	NPC475157
0.7525	Intermediate Similarity	NPC57586
0.7525	Intermediate Similarity	NPC154132
0.7525	Intermediate Similarity	NPC475655
0.7525	Intermediate Similarity	NPC2313
0.7524	Intermediate Similarity	NPC133625
0.75	Intermediate Similarity	NPC118078
0.7477	Intermediate Similarity	NPC471570
0.7475	Intermediate Similarity	NPC255410
0.7451	Intermediate Similarity	NPC201191
0.7451	Intermediate Similarity	NPC150463
0.7444	Intermediate Similarity	NPC180725
0.7419	Intermediate Similarity	NPC473308
0.7416	Intermediate Similarity	NPC474026
0.7407	Intermediate Similarity	NPC287075
0.74	Intermediate Similarity	NPC120299
0.7391	Intermediate Similarity	NPC251026
0.7379	Intermediate Similarity	NPC473070
0.7379	Intermediate Similarity	NPC197736
0.7374	Intermediate Similarity	NPC300710
0.7368	Intermediate Similarity	NPC313658
0.7368	Intermediate Similarity	NPC316138
0.7363	Intermediate Similarity	NPC470147
0.7363	Intermediate Similarity	NPC133226
0.7353	Intermediate Similarity	NPC198992
0.7353	Intermediate Similarity	NPC280991
0.7347	Intermediate Similarity	NPC320089
0.734	Intermediate Similarity	NPC475034
0.7333	Intermediate Similarity	NPC248775
0.7327	Intermediate Similarity	NPC475653
0.7327	Intermediate Similarity	NPC65700
0.732	Intermediate Similarity	NPC473311
0.732	Intermediate Similarity	NPC3952
0.7312	Intermediate Similarity	NPC142111
0.7312	Intermediate Similarity	NPC473315
0.7308	Intermediate Similarity	NPC473068
0.73	Intermediate Similarity	NPC143446
0.729	Intermediate Similarity	NPC89408
0.7282	Intermediate Similarity	NPC472754
0.7282	Intermediate Similarity	NPC149371
0.7273	Intermediate Similarity	NPC471496
0.7264	Intermediate Similarity	NPC473069
0.7255	Intermediate Similarity	NPC79631
0.7253	Intermediate Similarity	NPC470148
0.7253	Intermediate Similarity	NPC470149
0.7253	Intermediate Similarity	NPC139712
0.7241	Intermediate Similarity	NPC475762
0.7238	Intermediate Similarity	NPC29389
0.7238	Intermediate Similarity	NPC93026
0.7238	Intermediate Similarity	NPC315070
0.7238	Intermediate Similarity	NPC265502
0.7238	Intermediate Similarity	NPC469960
0.7238	Intermediate Similarity	NPC82251
0.7228	Intermediate Similarity	NPC309503
0.7228	Intermediate Similarity	NPC96597
0.7228	Intermediate Similarity	NPC155319
0.7228	Intermediate Similarity	NPC239547
0.7228	Intermediate Similarity	NPC475332
0.7228	Intermediate Similarity	NPC476613
0.7228	Intermediate Similarity	NPC40812
0.7228	Intermediate Similarity	NPC125551
0.7228	Intermediate Similarity	NPC471490
0.7228	Intermediate Similarity	NPC476612
0.7228	Intermediate Similarity	NPC91197
0.7222	Intermediate Similarity	NPC297945
0.7222	Intermediate Similarity	NPC126897
0.7212	Intermediate Similarity	NPC472755
0.7212	Intermediate Similarity	NPC474575
0.72	Intermediate Similarity	NPC471492
0.7196	Intermediate Similarity	NPC315836
0.7196	Intermediate Similarity	NPC313668
0.7188	Intermediate Similarity	NPC118077
0.7188	Intermediate Similarity	NPC475186
0.7184	Intermediate Similarity	NPC47880
0.7184	Intermediate Similarity	NPC476611
0.7184	Intermediate Similarity	NPC15993
0.7184	Intermediate Similarity	NPC472753
0.7184	Intermediate Similarity	NPC164598
0.7184	Intermediate Similarity	NPC474339
0.7174	Intermediate Similarity	NPC127295
0.7174	Intermediate Similarity	NPC163362
0.7172	Intermediate Similarity	NPC475098
0.7172	Intermediate Similarity	NPC476300
0.7172	Intermediate Similarity	NPC189651
0.717	Intermediate Similarity	NPC472263
0.717	Intermediate Similarity	NPC469959
0.717	Intermediate Similarity	NPC108682
0.717	Intermediate Similarity	NPC469957
0.7168	Intermediate Similarity	NPC107338
0.7168	Intermediate Similarity	NPC109607
0.7158	Intermediate Similarity	NPC471156
0.7158	Intermediate Similarity	NPC470124
0.7157	Intermediate Similarity	NPC83895
0.7157	Intermediate Similarity	NPC472015
0.7157	Intermediate Similarity	NPC255592
0.7157	Intermediate Similarity	NPC187761
0.7157	Intermediate Similarity	NPC261377
0.7157	Intermediate Similarity	NPC308567
0.7156	Intermediate Similarity	NPC313921
0.7156	Intermediate Similarity	NPC470025
0.7156	Intermediate Similarity	NPC317460
0.7156	Intermediate Similarity	NPC321272
0.7156	Intermediate Similarity	NPC98038
0.7156	Intermediate Similarity	NPC328074
0.7143	Intermediate Similarity	NPC327253
0.7143	Intermediate Similarity	NPC194941
0.7143	Intermediate Similarity	NPC474286
0.7143	Intermediate Similarity	NPC472756
0.7143	Intermediate Similarity	NPC475130
0.713	Intermediate Similarity	NPC316708
0.7129	Intermediate Similarity	NPC306041
0.7129	Intermediate Similarity	NPC54731
0.7128	Intermediate Similarity	NPC170286
0.7115	Intermediate Similarity	NPC473596
0.7115	Intermediate Similarity	NPC214277
0.7115	Intermediate Similarity	NPC324017
0.7115	Intermediate Similarity	NPC320019
0.7113	Intermediate Similarity	NPC248312
0.7111	Intermediate Similarity	NPC326661
0.7103	Intermediate Similarity	NPC219900
0.7103	Intermediate Similarity	NPC177524
0.7103	Intermediate Similarity	NPC392
0.71	Intermediate Similarity	NPC294293
0.71	Intermediate Similarity	NPC469491
0.7097	Intermediate Similarity	NPC8538
0.7097	Intermediate Similarity	NPC184208
0.7091	Intermediate Similarity	NPC470027
0.7091	Intermediate Similarity	NPC101965
0.7091	Intermediate Similarity	NPC101400
0.7087	Intermediate Similarity	NPC98813
0.7087	Intermediate Similarity	NPC13743
0.7087	Intermediate Similarity	NPC130792
0.7083	Intermediate Similarity	NPC477015
0.708	Intermediate Similarity	NPC475775
0.708	Intermediate Similarity	NPC476529
0.7075	Intermediate Similarity	NPC9303
0.7075	Intermediate Similarity	NPC16313
0.7071	Intermediate Similarity	NPC469410
0.7069	Intermediate Similarity	NPC470922
0.7065	Intermediate Similarity	NPC179933
0.7064	Intermediate Similarity	NPC17791
0.7064	Intermediate Similarity	NPC470026
0.7059	Intermediate Similarity	NPC2666
0.7059	Intermediate Similarity	NPC278506
0.7059	Intermediate Similarity	NPC218064
0.7054	Intermediate Similarity	NPC23046
0.7053	Intermediate Similarity	NPC160517
0.7053	Intermediate Similarity	NPC186155
0.7053	Intermediate Similarity	NPC288471
0.7053	Intermediate Similarity	NPC78673
0.7048	Intermediate Similarity	NPC475945
0.7048	Intermediate Similarity	NPC475871
0.7048	Intermediate Similarity	NPC4620
0.7048	Intermediate Similarity	NPC309398
0.7041	Intermediate Similarity	NPC477016
0.7041	Intermediate Similarity	NPC477017
0.7041	Intermediate Similarity	NPC285588
0.7033	Intermediate Similarity	NPC477203
0.7033	Intermediate Similarity	NPC475711
0.703	Intermediate Similarity	NPC473334
0.703	Intermediate Similarity	NPC36954
0.703	Intermediate Similarity	NPC471141

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 NPC471569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1718
0.2-0.3	4241
0.3-0.4	2130
0.4-0.5	591
0.5-0.6	273
0.6-0.7	53
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.75	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7143	Intermediate Similarity	NPD46	Approved
0.7143	Intermediate Similarity	NPD6698	Approved
0.7103	Intermediate Similarity	NPD6686	Approved
0.6852	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7503	Approved
0.6698	Remote Similarity	NPD5344	Discontinued
0.6604	Remote Similarity	NPD6648	Approved
0.6552	Remote Similarity	NPD7327	Approved
0.6552	Remote Similarity	NPD7328	Approved
0.6531	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8516	Approved
0.6525	Remote Similarity	NPD8517	Approved
0.6525	Remote Similarity	NPD8515	Approved
0.6525	Remote Similarity	NPD8513	Phase 3
0.6496	Remote Similarity	NPD7516	Approved
0.6457	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8377	Approved
0.6441	Remote Similarity	NPD8294	Approved
0.6417	Remote Similarity	NPD7642	Approved
0.6387	Remote Similarity	NPD8380	Approved
0.6387	Remote Similarity	NPD8296	Approved
0.6387	Remote Similarity	NPD8379	Approved
0.6387	Remote Similarity	NPD8335	Approved
0.6387	Remote Similarity	NPD8378	Approved
0.6387	Remote Similarity	NPD8033	Approved
0.6364	Remote Similarity	NPD7492	Approved
0.6311	Remote Similarity	NPD6616	Approved
0.6303	Remote Similarity	NPD6054	Approved
0.6281	Remote Similarity	NPD7830	Approved
0.6281	Remote Similarity	NPD7829	Approved
0.6261	Remote Similarity	NPD6882	Approved
0.626	Remote Similarity	NPD7078	Approved
0.626	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD6412	Phase 2
0.6228	Remote Similarity	NPD6371	Approved
0.621	Remote Similarity	NPD7736	Approved
0.6204	Remote Similarity	NPD4225	Approved
0.6198	Remote Similarity	NPD6370	Approved
0.6186	Remote Similarity	NPD6009	Approved
0.618	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7507	Approved
0.6167	Remote Similarity	NPD6319	Approved
0.6148	Remote Similarity	NPD8328	Phase 3
0.6139	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD1694	Approved
0.6132	Remote Similarity	NPD5282	Discontinued
0.6121	Remote Similarity	NPD8297	Approved
0.6116	Remote Similarity	NPD6015	Approved
0.6116	Remote Similarity	NPD6016	Approved
0.61	Remote Similarity	NPD6110	Phase 1
0.6066	Remote Similarity	NPD5988	Approved
0.6066	Remote Similarity	NPD8080	Discontinued
0.6053	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6059	Approved
0.6032	Remote Similarity	NPD7319	Approved
0.6019	Remote Similarity	NPD4250	Approved
0.6019	Remote Similarity	NPD4251	Approved
0.6019	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD7641	Discontinued
0.5984	Remote Similarity	NPD8444	Approved
0.5948	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7260	Phase 2
0.5932	Remote Similarity	NPD4632	Approved
0.5922	Remote Similarity	NPD4249	Approved
0.592	Remote Similarity	NPD8451	Approved
0.5917	Remote Similarity	NPD7115	Discovery
0.5913	Remote Similarity	NPD6881	Approved
0.5913	Remote Similarity	NPD6899	Approved
0.5909	Remote Similarity	NPD7638	Approved
0.5897	Remote Similarity	NPD6649	Approved
0.5897	Remote Similarity	NPD6650	Approved
0.5877	Remote Similarity	NPD4211	Phase 1
0.5873	Remote Similarity	NPD8448	Approved
0.5872	Remote Similarity	NPD7839	Suspended
0.5862	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7639	Approved
0.5856	Remote Similarity	NPD7640	Approved
0.5854	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5785	Approved
0.5849	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6053	Discontinued
0.5841	Remote Similarity	NPD1407	Approved
0.5826	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD5697	Approved
0.5818	Remote Similarity	NPD6084	Phase 2
0.5818	Remote Similarity	NPD6083	Phase 2
0.5816	Remote Similarity	NPD4756	Discovery
0.5812	Remote Similarity	NPD7102	Approved
0.5812	Remote Similarity	NPD7290	Approved
0.5812	Remote Similarity	NPD6883	Approved
0.58	Remote Similarity	NPD4820	Approved
0.58	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4819	Approved
0.58	Remote Similarity	NPD4821	Approved
0.58	Remote Similarity	NPD4822	Approved
0.5798	Remote Similarity	NPD8133	Approved
0.5785	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7500	Approved
0.578	Remote Similarity	NPD5695	Phase 3
0.578	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6845	Suspended
0.5763	Remote Similarity	NPD6869	Approved
0.5763	Remote Similarity	NPD6847	Approved
0.5763	Remote Similarity	NPD6617	Approved
0.5763	Remote Similarity	NPD8130	Phase 1
0.576	Remote Similarity	NPD7604	Phase 2
0.5755	Remote Similarity	NPD1695	Approved
0.5741	Remote Similarity	NPD5779	Approved
0.5741	Remote Similarity	NPD5778	Approved
0.5739	Remote Similarity	NPD6675	Approved
0.5739	Remote Similarity	NPD5739	Approved
0.5739	Remote Similarity	NPD7128	Approved
0.5739	Remote Similarity	NPD6402	Approved
0.5736	Remote Similarity	NPD5956	Approved
0.5736	Remote Similarity	NPD8391	Approved
0.5736	Remote Similarity	NPD8390	Approved
0.5736	Remote Similarity	NPD8392	Approved
0.5726	Remote Similarity	NPD5983	Phase 2
0.5726	Remote Similarity	NPD6014	Approved
0.5726	Remote Similarity	NPD6372	Approved
0.5726	Remote Similarity	NPD6013	Approved
0.5726	Remote Similarity	NPD6012	Approved
0.5726	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD8340	Approved
0.5714	Remote Similarity	NPD8341	Approved
0.5714	Remote Similarity	NPD8299	Approved
0.5714	Remote Similarity	NPD8342	Approved
0.5686	Remote Similarity	NPD6435	Approved
0.5686	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD5209	Approved
0.5682	Remote Similarity	NPD6109	Phase 1
0.5682	Remote Similarity	NPD8415	Approved
0.5673	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5363	Approved
0.5669	Remote Similarity	NPD6336	Discontinued
0.566	Remote Similarity	NPD5737	Approved
0.566	Remote Similarity	NPD6672	Approved
0.5656	Remote Similarity	NPD7505	Discontinued
0.5648	Remote Similarity	NPD5693	Phase 1
0.5648	Remote Similarity	NPD7637	Suspended
0.5645	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6011	Approved
0.5641	Remote Similarity	NPD7320	Approved
0.5639	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD7154	Phase 3
0.563	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5696	Approved
0.5612	Remote Similarity	NPD8039	Approved
0.5607	Remote Similarity	NPD6051	Approved
0.56	Remote Similarity	NPD4271	Approved
0.56	Remote Similarity	NPD6921	Approved
0.56	Remote Similarity	NPD4268	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