NPASS Compound

Structure

NPC106051 OpenBabel07101719132D 30 32 0 0 1 0 0 0 0 0999 V2000 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 22 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 9 20 1 0 0 0 0 10 18 2 0 0 0 0 11 23 1 0 0 0 0 12 17 2 0 0 0 0 13 19 2 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 14 26 1 0 0 0 0 15 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 20 8 1 6 0 0 0 20 29 1 0 0 0 0 21 11 1 1 0 0 0 21 24 1 0 0 0 0 22 27 2 0 0 0 0 23 28 2 0 0 0 0 24 10 1 1 0 0 0 24 30 1 0 0 0 0 25 12 1 1 0 0 0 25 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.24
Volume:	443.419
LogP:	2.971
LogD:	2.8
LogS:	-3.967
# Rotatable Bonds:	6
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.659
Synthetic Accessibility Score:	5.34
Fsp3:	0.6
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:	-4.509
MDCK Permeability:	1.7017846403177828e-05
Pgp-inhibitor:	0.869
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.96
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.265
Plasma Protein Binding (PPB):	87.31438446044922%
Volume Distribution (VD):	1.628
Pgp-substrate:	3.899367094039917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.367
CYP2C19-inhibitor:	0.267
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.621
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.696
CYP3A4-substrate:	0.477

ADMET: Excretion

Clearance (CL):	11.554
Half-life (T1/2):	0.687

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.909
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.316
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.872
Carcinogencity:	0.914
Eye Corrosion:	0.004
Eye Irritation:	0.044
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC106051

Natural Product ID:	NPC106051
*Common Name:**	Phorbaketal E
IUPAC Name:	(2S,4'aR,6S,8'aR)-2-[(E)-2,6-dimethyl-5-oxohept-1-enyl]-4'-(hydroxymethyl)-4,7'-dimethylspiro[2,3-dihydropyran-6,2'-5,8a-dihydro-4aH-chromene]-6'-one
Synonyms:	Phorbaketal E
Standard InCHIKey:	ADVQUGFWSPNWGG-MMHRJDEDSA-N
Standard InCHI:	InChI=1S/C25H34O5/c1-15(2)22(27)7-6-16(3)8-20-9-17(4)12-25(29-20)13-19(14-26)21-11-23(28)18(5)10-24(21)30-25/h8,10,12-13,15,20-21,24,26H,6-7,9,11,14H2,1-5H3/b16-8+/t20-,21-,24-,25+/m1/s1
SMILES:	CC(C)C(=O)CC/C(=C/[C@@H]1CC(=C[C@]2(C=C(CO)[C@H]3CC(=O)C(=C[C@H]3O2)C)O1)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2338628
PubChem CID:	71579367
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
NPO32454	monanchora sp.	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640525]
NPO32454	monanchora sp.	Species	Crambeidae	Eukaryota	n.a.	Korean	n.a.	PMID[23360104]
NPO32454	monanchora sp.	Species	Crambeidae	Eukaryota	n.a.	at 1520 m depth off the shore of Gageo Island, southwestern Korea	2009-JUL	PMID[25455409]

☑ 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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	25300.0	nM	PMID[455872]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	=	18000.0	nM	PMID[455872]
NPT376	Cell Line	A498	Homo sapiens	IC50	=	12500.0	nM	PMID[455872]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16700.0	nM	PMID[455872]

☑ 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 NPC106051 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	196
0.1-0.2	1207
0.2-0.3	5043
0.3-0.4	10794
0.4-0.5	14452
0.5-0.6	7501
0.6-0.7	3222
0.7-0.8	272
0.8-0.85	3
0.85-0.9	1
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC241054
0.9759	High Similarity	NPC472011
0.9643	High Similarity	NPC471054
0.9419	High Similarity	NPC472010
0.8977	High Similarity	NPC471059
0.8913	High Similarity	NPC472012
0.8295	Intermediate Similarity	NPC471060
0.8222	Intermediate Similarity	NPC471058
0.8222	Intermediate Similarity	NPC471057
0.7912	Intermediate Similarity	NPC471056
0.7912	Intermediate Similarity	NPC471055
0.7609	Intermediate Similarity	NPC186332
0.7609	Intermediate Similarity	NPC47220
0.7586	Intermediate Similarity	NPC471061
0.7579	Intermediate Similarity	NPC141831
0.7527	Intermediate Similarity	NPC316138
0.7527	Intermediate Similarity	NPC313658
0.75	Intermediate Similarity	NPC242233
0.75	Intermediate Similarity	NPC93763
0.75	Intermediate Similarity	NPC108816
0.75	Intermediate Similarity	NPC326753
0.75	Intermediate Similarity	NPC472637
0.7474	Intermediate Similarity	NPC232426
0.7474	Intermediate Similarity	NPC253186
0.7474	Intermediate Similarity	NPC281942
0.7474	Intermediate Similarity	NPC265856
0.7473	Intermediate Similarity	NPC40746
0.7473	Intermediate Similarity	NPC16488
0.7473	Intermediate Similarity	NPC44261
0.7473	Intermediate Similarity	NPC169575
0.7444	Intermediate Similarity	NPC112868
0.7426	Intermediate Similarity	NPC235369
0.7426	Intermediate Similarity	NPC201191
0.7426	Intermediate Similarity	NPC134077
0.7423	Intermediate Similarity	NPC298973
0.7423	Intermediate Similarity	NPC104925
0.7423	Intermediate Similarity	NPC476415
0.7423	Intermediate Similarity	NPC256368
0.7419	Intermediate Similarity	NPC315395
0.7419	Intermediate Similarity	NPC305475
0.7419	Intermediate Similarity	NPC475461
0.7419	Intermediate Similarity	NPC316426
0.7396	Intermediate Similarity	NPC477749
0.7391	Intermediate Similarity	NPC476804
0.7391	Intermediate Similarity	NPC96259
0.7391	Intermediate Similarity	NPC141193
0.7386	Intermediate Similarity	NPC116177
0.7386	Intermediate Similarity	NPC320630
0.7386	Intermediate Similarity	NPC7563
0.7374	Intermediate Similarity	NPC266842
0.7374	Intermediate Similarity	NPC76266
0.7368	Intermediate Similarity	NPC218927
0.7368	Intermediate Similarity	NPC268298
0.7368	Intermediate Similarity	NPC206001
0.7356	Intermediate Similarity	NPC315552
0.734	Intermediate Similarity	NPC300779
0.7333	Intermediate Similarity	NPC137911
0.7333	Intermediate Similarity	NPC228477
0.7327	Intermediate Similarity	NPC469657
0.7327	Intermediate Similarity	NPC244456
0.7327	Intermediate Similarity	NPC63249
0.732	Intermediate Similarity	NPC472196
0.732	Intermediate Similarity	NPC238090
0.732	Intermediate Similarity	NPC472195
0.732	Intermediate Similarity	NPC476416
0.7312	Intermediate Similarity	NPC28887
0.7312	Intermediate Similarity	NPC163606
0.7312	Intermediate Similarity	NPC470755
0.7312	Intermediate Similarity	NPC476426
0.7312	Intermediate Similarity	NPC255307
0.7312	Intermediate Similarity	NPC165162
0.7308	Intermediate Similarity	NPC91034
0.73	Intermediate Similarity	NPC473154
0.73	Intermediate Similarity	NPC203627
0.73	Intermediate Similarity	NPC478056
0.7294	Intermediate Similarity	NPC4299
0.7292	Intermediate Similarity	NPC3952
0.7292	Intermediate Similarity	NPC129419
0.7283	Intermediate Similarity	NPC116543
0.7283	Intermediate Similarity	NPC106912
0.7283	Intermediate Similarity	NPC473390
0.7283	Intermediate Similarity	NPC2379
0.7283	Intermediate Similarity	NPC263087
0.7283	Intermediate Similarity	NPC31019
0.7283	Intermediate Similarity	NPC131669
0.7283	Intermediate Similarity	NPC27314
0.7282	Intermediate Similarity	NPC118911
0.7264	Intermediate Similarity	NPC37116
0.7263	Intermediate Similarity	NPC476805
0.7263	Intermediate Similarity	NPC477302
0.7263	Intermediate Similarity	NPC136879
0.7255	Intermediate Similarity	NPC475320
0.7255	Intermediate Similarity	NPC136289
0.7253	Intermediate Similarity	NPC24417
0.7245	Intermediate Similarity	NPC469697
0.7245	Intermediate Similarity	NPC71589
0.7245	Intermediate Similarity	NPC159698
0.7241	Intermediate Similarity	NPC476590
0.7241	Intermediate Similarity	NPC114727
0.7234	Intermediate Similarity	NPC220478
0.7234	Intermediate Similarity	NPC311163
0.7228	Intermediate Similarity	NPC472644
0.7228	Intermediate Similarity	NPC476274
0.7222	Intermediate Similarity	NPC157441
0.7222	Intermediate Similarity	NPC139712
0.7216	Intermediate Similarity	NPC470379
0.7216	Intermediate Similarity	NPC470373
0.7207	Intermediate Similarity	NPC474179
0.7207	Intermediate Similarity	NPC475834
0.7204	Intermediate Similarity	NPC31086
0.7204	Intermediate Similarity	NPC243618
0.7204	Intermediate Similarity	NPC474865
0.7204	Intermediate Similarity	NPC70424
0.7204	Intermediate Similarity	NPC114979
0.7204	Intermediate Similarity	NPC126518
0.7204	Intermediate Similarity	NPC191476
0.7204	Intermediate Similarity	NPC158756
0.72	Intermediate Similarity	NPC170131
0.72	Intermediate Similarity	NPC20066
0.72	Intermediate Similarity	NPC474343
0.7191	Intermediate Similarity	NPC315394
0.7188	Intermediate Similarity	NPC295312
0.7188	Intermediate Similarity	NPC5509
0.7188	Intermediate Similarity	NPC212598
0.7188	Intermediate Similarity	NPC307092
0.7188	Intermediate Similarity	NPC477748
0.7188	Intermediate Similarity	NPC133450
0.7184	Intermediate Similarity	NPC151516
0.7176	Intermediate Similarity	NPC151481
0.7176	Intermediate Similarity	NPC101622
0.7174	Intermediate Similarity	NPC123908
0.7174	Intermediate Similarity	NPC471298
0.7174	Intermediate Similarity	NPC229825
0.7174	Intermediate Similarity	NPC10080
0.7172	Intermediate Similarity	NPC227494
0.7158	Intermediate Similarity	NPC113370
0.7158	Intermediate Similarity	NPC476079
0.7158	Intermediate Similarity	NPC103743
0.7158	Intermediate Similarity	NPC312561
0.7157	Intermediate Similarity	NPC469851
0.7157	Intermediate Similarity	NPC476223
0.7157	Intermediate Similarity	NPC224720
0.7157	Intermediate Similarity	NPC81530
0.7157	Intermediate Similarity	NPC476240
0.7157	Intermediate Similarity	NPC472643
0.7143	Intermediate Similarity	NPC162205
0.7143	Intermediate Similarity	NPC109406
0.7143	Intermediate Similarity	NPC273579
0.7143	Intermediate Similarity	NPC189651
0.7143	Intermediate Similarity	NPC288240
0.7143	Intermediate Similarity	NPC295204
0.7143	Intermediate Similarity	NPC475098
0.7143	Intermediate Similarity	NPC166346
0.7143	Intermediate Similarity	NPC159092
0.713	Intermediate Similarity	NPC194951
0.713	Intermediate Similarity	NPC236217
0.713	Intermediate Similarity	NPC12046
0.7129	Intermediate Similarity	NPC198422
0.7129	Intermediate Similarity	NPC40182
0.7129	Intermediate Similarity	NPC23364
0.7129	Intermediate Similarity	NPC316598
0.7128	Intermediate Similarity	NPC474860
0.7128	Intermediate Similarity	NPC261380
0.7128	Intermediate Similarity	NPC21469
0.7128	Intermediate Similarity	NPC471494
0.7128	Intermediate Similarity	NPC471300
0.7126	Intermediate Similarity	NPC316851
0.7117	Intermediate Similarity	NPC475913
0.7113	Intermediate Similarity	NPC166554
0.7113	Intermediate Similarity	NPC144133
0.7113	Intermediate Similarity	NPC202886
0.7113	Intermediate Similarity	NPC473455
0.7113	Intermediate Similarity	NPC475855
0.7113	Intermediate Similarity	NPC471399
0.7113	Intermediate Similarity	NPC177668
0.7113	Intermediate Similarity	NPC179394
0.7111	Intermediate Similarity	NPC475994
0.7111	Intermediate Similarity	NPC267231
0.7111	Intermediate Similarity	NPC231739
0.7111	Intermediate Similarity	NPC196653
0.7111	Intermediate Similarity	NPC471465
0.7111	Intermediate Similarity	NPC478122
0.71	Intermediate Similarity	NPC162346
0.71	Intermediate Similarity	NPC112654
0.7097	Intermediate Similarity	NPC475083
0.7097	Intermediate Similarity	NPC297398
0.7097	Intermediate Similarity	NPC52609
0.7097	Intermediate Similarity	NPC59097
0.7097	Intermediate Similarity	NPC471297
0.7097	Intermediate Similarity	NPC286770
0.7097	Intermediate Similarity	NPC284472
0.7097	Intermediate Similarity	NPC1761
0.7097	Intermediate Similarity	NPC229799
0.7087	Intermediate Similarity	NPC273005
0.7087	Intermediate Similarity	NPC469606
0.7087	Intermediate Similarity	NPC31058
0.7087	Intermediate Similarity	NPC137430
0.7083	Intermediate Similarity	NPC473658
0.7083	Intermediate Similarity	NPC476803
0.7083	Intermediate Similarity	NPC475819

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 NPC106051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1649
0.2-0.3	3892
0.3-0.4	2391
0.4-0.5	681
0.5-0.6	305
0.6-0.7	48
0.7-0.8	2
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
0.7475	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD46	Approved
0.6939	Remote Similarity	NPD5785	Approved
0.6939	Remote Similarity	NPD6698	Approved
0.6818	Remote Similarity	NPD6053	Discontinued
0.6771	Remote Similarity	NPD5363	Approved
0.6759	Remote Similarity	NPD6686	Approved
0.6737	Remote Similarity	NPD6110	Phase 1
0.6731	Remote Similarity	NPD7640	Approved
0.6731	Remote Similarity	NPD7639	Approved
0.6727	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD8513	Phase 3
0.6635	Remote Similarity	NPD4225	Approved
0.6635	Remote Similarity	NPD7638	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6634	Remote Similarity	NPD5778	Approved
0.6634	Remote Similarity	NPD5779	Approved
0.66	Remote Similarity	NPD7838	Discovery
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD1694	Approved
0.6596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7154	Phase 3
0.6538	Remote Similarity	NPD7902	Approved
0.6531	Remote Similarity	NPD5786	Approved
0.6518	Remote Similarity	NPD6882	Approved
0.6514	Remote Similarity	NPD6412	Phase 2
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6101	Approved
0.6496	Remote Similarity	NPD8517	Approved
0.6496	Remote Similarity	NPD8516	Approved
0.6496	Remote Similarity	NPD8515	Approved
0.6458	Remote Similarity	NPD4269	Approved
0.6458	Remote Similarity	NPD4270	Approved
0.6442	Remote Similarity	NPD7839	Suspended
0.6437	Remote Similarity	NPD7331	Phase 2
0.6429	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4822	Approved
0.6421	Remote Similarity	NPD4820	Approved
0.6421	Remote Similarity	NPD4821	Approved
0.6421	Remote Similarity	NPD4819	Approved
0.6408	Remote Similarity	NPD7748	Approved
0.6392	Remote Similarity	NPD5362	Discontinued
0.6383	Remote Similarity	NPD4271	Approved
0.6383	Remote Similarity	NPD4268	Approved
0.6373	Remote Similarity	NPD6411	Approved
0.6373	Remote Similarity	NPD7983	Approved
0.6373	Remote Similarity	NPD7515	Phase 2
0.6373	Remote Similarity	NPD6079	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6353	Remote Similarity	NPD368	Approved
0.6339	Remote Similarity	NPD6371	Approved
0.6337	Remote Similarity	NPD5328	Approved
0.6327	Remote Similarity	NPD3665	Phase 1
0.6327	Remote Similarity	NPD3133	Approved
0.6327	Remote Similarity	NPD3666	Approved
0.6327	Remote Similarity	NPD4786	Approved
0.6306	Remote Similarity	NPD6899	Approved
0.6306	Remote Similarity	NPD6881	Approved
0.6296	Remote Similarity	NPD5211	Phase 2
0.6289	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3667	Approved
0.6289	Remote Similarity	NPD6435	Approved
0.6283	Remote Similarity	NPD6649	Approved
0.6283	Remote Similarity	NPD6650	Approved
0.6277	Remote Similarity	NPD4756	Discovery
0.6273	Remote Similarity	NPD5739	Approved
0.6273	Remote Similarity	NPD7128	Approved
0.6273	Remote Similarity	NPD6402	Approved
0.6273	Remote Similarity	NPD6675	Approved
0.6263	Remote Similarity	NPD1696	Phase 3
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD4695	Discontinued
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6372	Approved
0.623	Remote Similarity	NPD8074	Phase 3
0.6226	Remote Similarity	NPD6083	Phase 2
0.6226	Remote Similarity	NPD6084	Phase 2
0.6224	Remote Similarity	NPD5332	Approved
0.6224	Remote Similarity	NPD5331	Approved
0.6216	Remote Similarity	NPD5697	Approved
0.6211	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5344	Discontinued
0.62	Remote Similarity	NPD6409	Approved
0.62	Remote Similarity	NPD7334	Approved
0.62	Remote Similarity	NPD7146	Approved
0.62	Remote Similarity	NPD7521	Approved
0.62	Remote Similarity	NPD5330	Approved
0.62	Remote Similarity	NPD6684	Approved
0.6195	Remote Similarity	NPD7290	Approved
0.6195	Remote Similarity	NPD6883	Approved
0.6195	Remote Similarity	NPD7102	Approved
0.6186	Remote Similarity	NPD4790	Discontinued
0.6186	Remote Similarity	NPD5369	Approved
0.6182	Remote Similarity	NPD5141	Approved
0.6161	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD7500	Approved
0.6147	Remote Similarity	NPD7632	Discontinued
0.614	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6617	Approved
0.614	Remote Similarity	NPD6869	Approved
0.6139	Remote Similarity	NPD4250	Approved
0.6139	Remote Similarity	NPD4251	Approved
0.6136	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7341	Phase 2
0.6134	Remote Similarity	NPD6054	Approved
0.6132	Remote Similarity	NPD5222	Approved
0.6132	Remote Similarity	NPD4697	Phase 3
0.6132	Remote Similarity	NPD5221	Approved
0.6132	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5209	Approved
0.6111	Remote Similarity	NPD5286	Approved
0.6111	Remote Similarity	NPD4696	Approved
0.6111	Remote Similarity	NPD5285	Approved
0.6106	Remote Similarity	NPD6014	Approved
0.6106	Remote Similarity	NPD6012	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6087	Remote Similarity	NPD8297	Approved
0.6083	Remote Similarity	NPD7503	Approved
0.6082	Remote Similarity	NPD5368	Approved
0.6078	Remote Similarity	NPD6672	Approved
0.6078	Remote Similarity	NPD5737	Approved
0.6078	Remote Similarity	NPD6903	Approved
0.6078	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4755	Approved
0.6075	Remote Similarity	NPD5173	Approved
0.6071	Remote Similarity	NPD5701	Approved
0.6071	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD8039	Approved
0.6058	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7637	Suspended
0.6055	Remote Similarity	NPD5223	Approved
0.604	Remote Similarity	NPD4519	Discontinued
0.604	Remote Similarity	NPD4623	Approved
0.604	Remote Similarity	NPD4249	Approved
0.604	Remote Similarity	NPD5279	Phase 3
0.6038	Remote Similarity	NPD5695	Phase 3
0.6038	Remote Similarity	NPD5210	Approved
0.6038	Remote Similarity	NPD4629	Approved
0.6033	Remote Similarity	NPD6370	Approved
0.6024	Remote Similarity	NPD342	Phase 1
0.6019	Remote Similarity	NPD5696	Approved
0.6019	Remote Similarity	NPD5370	Suspended
0.6019	Remote Similarity	NPD4753	Phase 2
0.6017	Remote Similarity	NPD6009	Approved
0.6016	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD4202	Approved
0.5984	Remote Similarity	NPD7830	Approved
0.5984	Remote Similarity	NPD7642	Approved
0.5984	Remote Similarity	NPD8328	Phase 3
0.5984	Remote Similarity	NPD7829	Approved
0.5966	Remote Similarity	NPD7641	Discontinued
0.5963	Remote Similarity	NPD4700	Approved
0.5963	Remote Similarity	NPD6648	Approved
0.595	Remote Similarity	NPD6016	Approved
0.595	Remote Similarity	NPD6015	Approved
0.5946	Remote Similarity	NPD5174	Approved
0.5946	Remote Similarity	NPD5175	Approved
0.5946	Remote Similarity	NPD6647	Phase 2
0.5943	Remote Similarity	NPD5282	Discontinued
0.5941	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7492	Approved
0.5909	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7260	Phase 2
0.5905	Remote Similarity	NPD5284	Approved
0.5905	Remote Similarity	NPD5281	Approved
0.5905	Remote Similarity	NPD5693	Phase 1
0.5902	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD7623	Phase 3
0.5902	Remote Similarity	NPD5988	Approved
0.5895	Remote Similarity	NPD8264	Approved
0.5889	Remote Similarity	NPD3704	Approved
0.5887	Remote Similarity	NPD6616	Approved
0.5882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6422	Discontinued
0.5873	Remote Similarity	NPD7319	Approved
0.5868	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6051	Approved
0.5862	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD3668	Phase 3
0.5841	Remote Similarity	NPD6008	Approved
0.584	Remote Similarity	NPD7078	Approved
0.5833	Remote Similarity	NPD6335	Approved
0.5833	Remote Similarity	NPD7327	Approved
0.5833	Remote Similarity	NPD7328	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