NPASS Compound

Structure

NPC241054 OpenBabel07101718202D 29 31 0 0 1 0 0 0 0 0999 V2000 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 6.5000 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 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 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 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 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 2.5981 5.5000 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 -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 -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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 17 2 0 0 0 0 10 18 1 0 0 0 0 10 21 1 0 0 0 0 11 19 2 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 20 1 0 0 0 0 15 26 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 21 9 1 6 0 0 0 21 28 1 0 0 0 0 22 12 1 1 0 0 0 22 24 1 0 0 0 0 23 27 2 0 0 0 0 24 11 1 1 0 0 0 24 29 1 0 0 0 0 25 13 1 1 0 0 0 25 28 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.25
Volume:	434.629
LogP:	5.116
LogD:	3.746
LogS:	-4.07
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	5.34
Fsp3:	0.56
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.556
MDCK Permeability:	1.9338731362950057e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.087
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	94.78339385986328%
Volume Distribution (VD):	1.989
Pgp-substrate:	4.936259746551514%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.299
CYP2C19-inhibitor:	0.647
CYP2C19-substrate:	0.763
CYP2C9-inhibitor:	0.745
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.733
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	13.448
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.642
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.957
Carcinogencity:	0.509
Eye Corrosion:	0.005
Eye Irritation:	0.341
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC241054

Natural Product ID:	NPC241054
*Common Name:**	Phorbaketal A
IUPAC Name:	(2S,4'aR,6S,8'aR)-2-[(1E)-2,6-dimethylhepta-1,5-dienyl]-4'-(hydroxymethyl)-4,7'-dimethylspiro[2,3-dihydropyran-6,2'-5,8a-dihydro-4aH-chromene]-6'-one
Synonyms:
Standard InCHIKey:	PRJFAAVCONGPLR-YAMNEPGGSA-N
Standard InCHI:	InChI=1S/C25H34O4/c1-16(2)7-6-8-17(3)9-21-10-18(4)13-25(28-21)14-20(15-26)22-12-23(27)19(5)11-24(22)29-25/h7,9,11,13-14,21-22,24,26H,6,8,10,12,15H2,1-5H3/b17-9+/t21-,22-,24-,25+/m1/s1
SMILES:	OCC1=C[C@@]2(O[C@H](/C=C(/CCC=C(C)C)C)CC(=C2)C)O[C@H]2[C@@H]1CC(=O)C(=C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3322970
PubChem CID:	44605826
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
NPO32877	phorbas	Genus	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25124114]

☑ 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	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT376	Cell Line	A498	Homo sapiens	IC50	=	4400.0	nM	PMID[517726]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	=	3000.0	nM	PMID[517726]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13500.0	nM	PMID[517726]

☑ 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 NPC241054 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	1246
0.2-0.3	5198
0.3-0.4	11724
0.4-0.5	13838
0.5-0.6	7409
0.6-0.7	2836
0.7-0.8	240
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC472011
0.9878	High Similarity	NPC106051
0.9759	High Similarity	NPC471054
0.9529	High Similarity	NPC472010
0.908	High Similarity	NPC471059
0.8804	High Similarity	NPC472012
0.8391	Intermediate Similarity	NPC471060
0.8315	Intermediate Similarity	NPC471057
0.8315	Intermediate Similarity	NPC471058
0.8	Intermediate Similarity	NPC471056
0.8	Intermediate Similarity	NPC471055
0.7674	Intermediate Similarity	NPC471061
0.7586	Intermediate Similarity	NPC93763
0.7586	Intermediate Similarity	NPC108816
0.7556	Intermediate Similarity	NPC169575
0.7556	Intermediate Similarity	NPC40746
0.75	Intermediate Similarity	NPC47220
0.75	Intermediate Similarity	NPC186332
0.7474	Intermediate Similarity	NPC141831
0.7471	Intermediate Similarity	NPC320630
0.7471	Intermediate Similarity	NPC116177
0.7471	Intermediate Similarity	NPC7563
0.7442	Intermediate Similarity	NPC315552
0.7419	Intermediate Similarity	NPC313658
0.7419	Intermediate Similarity	NPC316138
0.74	Intermediate Similarity	NPC472637
0.7391	Intermediate Similarity	NPC470755
0.7391	Intermediate Similarity	NPC242233
0.7386	Intermediate Similarity	NPC326753
0.7368	Intermediate Similarity	NPC281942
0.7368	Intermediate Similarity	NPC253186
0.7368	Intermediate Similarity	NPC265856
0.7368	Intermediate Similarity	NPC232426
0.7363	Intermediate Similarity	NPC116543
0.7363	Intermediate Similarity	NPC16488
0.7363	Intermediate Similarity	NPC473390
0.7363	Intermediate Similarity	NPC44261
0.7363	Intermediate Similarity	NPC131669
0.7333	Intermediate Similarity	NPC24417
0.7333	Intermediate Similarity	NPC112868
0.7327	Intermediate Similarity	NPC235369
0.7327	Intermediate Similarity	NPC201191
0.7327	Intermediate Similarity	NPC134077
0.7326	Intermediate Similarity	NPC114727
0.7326	Intermediate Similarity	NPC476590
0.732	Intermediate Similarity	NPC476415
0.732	Intermediate Similarity	NPC256368
0.732	Intermediate Similarity	NPC298973
0.732	Intermediate Similarity	NPC104925
0.7312	Intermediate Similarity	NPC475461
0.7312	Intermediate Similarity	NPC305475
0.7312	Intermediate Similarity	NPC316426
0.7312	Intermediate Similarity	NPC315395
0.7292	Intermediate Similarity	NPC477749
0.7283	Intermediate Similarity	NPC158756
0.7283	Intermediate Similarity	NPC96259
0.7283	Intermediate Similarity	NPC141193
0.7283	Intermediate Similarity	NPC476804
0.7273	Intermediate Similarity	NPC266842
0.7273	Intermediate Similarity	NPC76266
0.7263	Intermediate Similarity	NPC206001
0.7263	Intermediate Similarity	NPC268298
0.7263	Intermediate Similarity	NPC218927
0.7253	Intermediate Similarity	NPC229825
0.7238	Intermediate Similarity	NPC137911
0.7238	Intermediate Similarity	NPC228477
0.7234	Intermediate Similarity	NPC300779
0.7228	Intermediate Similarity	NPC469657
0.7228	Intermediate Similarity	NPC244456
0.7228	Intermediate Similarity	NPC63249
0.7216	Intermediate Similarity	NPC472196
0.7216	Intermediate Similarity	NPC288240
0.7216	Intermediate Similarity	NPC273579
0.7216	Intermediate Similarity	NPC162205
0.7216	Intermediate Similarity	NPC472195
0.7216	Intermediate Similarity	NPC238090
0.7216	Intermediate Similarity	NPC295204
0.7216	Intermediate Similarity	NPC476416
0.7212	Intermediate Similarity	NPC91034
0.7209	Intermediate Similarity	NPC316851
0.7204	Intermediate Similarity	NPC476426
0.7204	Intermediate Similarity	NPC163606
0.7204	Intermediate Similarity	NPC255307
0.7204	Intermediate Similarity	NPC28887
0.7204	Intermediate Similarity	NPC21469
0.7204	Intermediate Similarity	NPC165162
0.72	Intermediate Similarity	NPC198422
0.72	Intermediate Similarity	NPC40182
0.72	Intermediate Similarity	NPC473154
0.72	Intermediate Similarity	NPC203627
0.72	Intermediate Similarity	NPC478056
0.7191	Intermediate Similarity	NPC267231
0.7191	Intermediate Similarity	NPC196653
0.7191	Intermediate Similarity	NPC471465
0.7188	Intermediate Similarity	NPC129419
0.7188	Intermediate Similarity	NPC3952
0.7188	Intermediate Similarity	NPC473455
0.7184	Intermediate Similarity	NPC118911
0.7176	Intermediate Similarity	NPC4299
0.7174	Intermediate Similarity	NPC59097
0.7174	Intermediate Similarity	NPC284472
0.7174	Intermediate Similarity	NPC2379
0.7174	Intermediate Similarity	NPC106912
0.7174	Intermediate Similarity	NPC263087
0.7174	Intermediate Similarity	NPC286770
0.7174	Intermediate Similarity	NPC31019
0.7174	Intermediate Similarity	NPC229799
0.7174	Intermediate Similarity	NPC27314
0.717	Intermediate Similarity	NPC37116
0.7159	Intermediate Similarity	NPC68819
0.7158	Intermediate Similarity	NPC475819
0.7158	Intermediate Similarity	NPC136879
0.7158	Intermediate Similarity	NPC476805
0.7158	Intermediate Similarity	NPC477302
0.7157	Intermediate Similarity	NPC136289
0.7157	Intermediate Similarity	NPC475320
0.7143	Intermediate Similarity	NPC469697
0.7143	Intermediate Similarity	NPC159698
0.7143	Intermediate Similarity	NPC71589
0.7143	Intermediate Similarity	NPC2003
0.7143	Intermediate Similarity	NPC25701
0.713	Intermediate Similarity	NPC157441
0.7129	Intermediate Similarity	NPC476274
0.7129	Intermediate Similarity	NPC472644
0.7128	Intermediate Similarity	NPC311163
0.7128	Intermediate Similarity	NPC469910
0.7128	Intermediate Similarity	NPC220478
0.7126	Intermediate Similarity	NPC140287
0.7126	Intermediate Similarity	NPC215050
0.7126	Intermediate Similarity	NPC476355
0.7117	Intermediate Similarity	NPC474179
0.7117	Intermediate Similarity	NPC475834
0.7113	Intermediate Similarity	NPC473321
0.7113	Intermediate Similarity	NPC470373
0.7113	Intermediate Similarity	NPC470379
0.7111	Intermediate Similarity	NPC321728
0.7111	Intermediate Similarity	NPC139712
0.7111	Intermediate Similarity	NPC270126
0.7111	Intermediate Similarity	NPC98557
0.7111	Intermediate Similarity	NPC167881
0.71	Intermediate Similarity	NPC474343
0.71	Intermediate Similarity	NPC170131
0.71	Intermediate Similarity	NPC20066
0.7097	Intermediate Similarity	NPC114979
0.7097	Intermediate Similarity	NPC31086
0.7097	Intermediate Similarity	NPC243618
0.7097	Intermediate Similarity	NPC70424
0.7097	Intermediate Similarity	NPC126518
0.7097	Intermediate Similarity	NPC474865
0.7097	Intermediate Similarity	NPC191476
0.7093	Intermediate Similarity	NPC477087
0.7093	Intermediate Similarity	NPC477086
0.7087	Intermediate Similarity	NPC284929
0.7087	Intermediate Similarity	NPC151516
0.7087	Intermediate Similarity	NPC267869
0.7087	Intermediate Similarity	NPC118761
0.7087	Intermediate Similarity	NPC197541
0.7087	Intermediate Similarity	NPC234304
0.7083	Intermediate Similarity	NPC295312
0.7083	Intermediate Similarity	NPC5509
0.7083	Intermediate Similarity	NPC477748
0.7083	Intermediate Similarity	NPC212598
0.7083	Intermediate Similarity	NPC307092
0.7083	Intermediate Similarity	NPC133450
0.7083	Intermediate Similarity	NPC87306
0.7079	Intermediate Similarity	NPC97516
0.7079	Intermediate Similarity	NPC315394
0.7071	Intermediate Similarity	NPC170204
0.7071	Intermediate Similarity	NPC469543
0.7071	Intermediate Similarity	NPC227494
0.7065	Intermediate Similarity	NPC10080
0.7065	Intermediate Similarity	NPC11383
0.7065	Intermediate Similarity	NPC474959
0.7065	Intermediate Similarity	NPC471298
0.7065	Intermediate Similarity	NPC310450
0.7065	Intermediate Similarity	NPC123908
0.7065	Intermediate Similarity	NPC475046
0.7059	Intermediate Similarity	NPC28304
0.7059	Intermediate Similarity	NPC224720
0.7059	Intermediate Similarity	NPC151481
0.7059	Intermediate Similarity	NPC472643
0.7059	Intermediate Similarity	NPC298255
0.7059	Intermediate Similarity	NPC101622
0.7059	Intermediate Similarity	NPC81530
0.7059	Intermediate Similarity	NPC476240
0.7059	Intermediate Similarity	NPC469851
0.7059	Intermediate Similarity	NPC476223
0.7053	Intermediate Similarity	NPC103743
0.7053	Intermediate Similarity	NPC113370
0.7053	Intermediate Similarity	NPC312561
0.7053	Intermediate Similarity	NPC476079
0.7053	Intermediate Similarity	NPC45409
0.7041	Intermediate Similarity	NPC475098
0.7041	Intermediate Similarity	NPC320552
0.7041	Intermediate Similarity	NPC109406
0.7041	Intermediate Similarity	NPC11456
0.7041	Intermediate Similarity	NPC189651
0.7041	Intermediate Similarity	NPC61201
0.7041	Intermediate Similarity	NPC159092
0.7041	Intermediate Similarity	NPC166346

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 NPC241054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1693
0.2-0.3	3897
0.3-0.4	2430
0.4-0.5	631
0.5-0.6	282
0.6-0.7	35
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
0.7374	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6698	Approved
0.6837	Remote Similarity	NPD46	Approved
0.6837	Remote Similarity	NPD5785	Approved
0.6809	Remote Similarity	NPD6110	Phase 1
0.6727	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5363	Approved
0.6637	Remote Similarity	NPD7115	Discovery
0.6636	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7640	Approved
0.6635	Remote Similarity	NPD7639	Approved
0.6569	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8513	Phase 3
0.6538	Remote Similarity	NPD4225	Approved
0.6538	Remote Similarity	NPD7638	Approved
0.6535	Remote Similarity	NPD6399	Phase 3
0.6535	Remote Similarity	NPD5778	Approved
0.6535	Remote Similarity	NPD5779	Approved
0.65	Remote Similarity	NPD7838	Discovery
0.6495	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD1694	Approved
0.6458	Remote Similarity	NPD7154	Phase 3
0.6452	Remote Similarity	NPD4268	Approved
0.6452	Remote Similarity	NPD4271	Approved
0.6442	Remote Similarity	NPD7902	Approved
0.6429	Remote Similarity	NPD5786	Approved
0.6429	Remote Similarity	NPD6882	Approved
0.6422	Remote Similarity	NPD6412	Phase 2
0.641	Remote Similarity	NPD8517	Approved
0.641	Remote Similarity	NPD8516	Approved
0.641	Remote Similarity	NPD8515	Approved
0.64	Remote Similarity	NPD6101	Approved
0.64	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4270	Approved
0.6354	Remote Similarity	NPD4269	Approved
0.6346	Remote Similarity	NPD7839	Suspended
0.6344	Remote Similarity	NPD4756	Discovery
0.6339	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7331	Phase 2
0.6316	Remote Similarity	NPD4820	Approved
0.6316	Remote Similarity	NPD4822	Approved
0.6316	Remote Similarity	NPD4821	Approved
0.6316	Remote Similarity	NPD4819	Approved
0.6316	Remote Similarity	NPD4252	Approved
0.6311	Remote Similarity	NPD7748	Approved
0.6289	Remote Similarity	NPD5362	Discontinued
0.6275	Remote Similarity	NPD6411	Approved
0.6275	Remote Similarity	NPD7983	Approved
0.6275	Remote Similarity	NPD7515	Phase 2
0.6275	Remote Similarity	NPD6079	Approved
0.6263	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD6371	Approved
0.6238	Remote Similarity	NPD5328	Approved
0.6235	Remote Similarity	NPD368	Approved
0.6224	Remote Similarity	NPD3665	Phase 1
0.6224	Remote Similarity	NPD3666	Approved
0.6224	Remote Similarity	NPD4786	Approved
0.6224	Remote Similarity	NPD3133	Approved
0.6216	Remote Similarity	NPD6881	Approved
0.6216	Remote Similarity	NPD6899	Approved
0.6204	Remote Similarity	NPD5211	Phase 2
0.62	Remote Similarity	NPD4251	Approved
0.62	Remote Similarity	NPD4250	Approved
0.6195	Remote Similarity	NPD6649	Approved
0.6195	Remote Similarity	NPD6650	Approved
0.6186	Remote Similarity	NPD6435	Approved
0.6186	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5209	Approved
0.6186	Remote Similarity	NPD3667	Approved
0.6182	Remote Similarity	NPD7128	Approved
0.6182	Remote Similarity	NPD6675	Approved
0.6182	Remote Similarity	NPD5739	Approved
0.6182	Remote Similarity	NPD6402	Approved
0.6162	Remote Similarity	NPD1696	Phase 3
0.6161	Remote Similarity	NPD6373	Approved
0.6161	Remote Similarity	NPD6372	Approved
0.6154	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7900	Approved
0.6148	Remote Similarity	NPD8074	Phase 3
0.6146	Remote Similarity	NPD4695	Discontinued
0.6146	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6084	Phase 2
0.6132	Remote Similarity	NPD6083	Phase 2
0.6126	Remote Similarity	NPD5697	Approved
0.6122	Remote Similarity	NPD5332	Approved
0.6122	Remote Similarity	NPD5331	Approved
0.6117	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5344	Discontinued
0.6106	Remote Similarity	NPD7290	Approved
0.6106	Remote Similarity	NPD6883	Approved
0.6106	Remote Similarity	NPD7102	Approved
0.6105	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7146	Approved
0.61	Remote Similarity	NPD5330	Approved
0.61	Remote Similarity	NPD6409	Approved
0.61	Remote Similarity	NPD4249	Approved
0.61	Remote Similarity	NPD7334	Approved
0.61	Remote Similarity	NPD7521	Approved
0.61	Remote Similarity	NPD6684	Approved
0.6098	Remote Similarity	NPD342	Phase 1
0.6091	Remote Similarity	NPD5141	Approved
0.6082	Remote Similarity	NPD5369	Approved
0.6082	Remote Similarity	NPD4790	Discontinued
0.6078	Remote Similarity	NPD5370	Suspended
0.6071	Remote Similarity	NPD6011	Approved
0.6071	Remote Similarity	NPD7320	Approved
0.6068	Remote Similarity	NPD7500	Approved
0.6055	Remote Similarity	NPD7632	Discontinued
0.6053	Remote Similarity	NPD6869	Approved
0.6053	Remote Similarity	NPD6847	Approved
0.6053	Remote Similarity	NPD6617	Approved
0.6053	Remote Similarity	NPD8130	Phase 1
0.605	Remote Similarity	NPD6054	Approved
0.6038	Remote Similarity	NPD5221	Approved
0.6038	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5222	Approved
0.6038	Remote Similarity	NPD4697	Phase 3
0.6023	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7341	Phase 2
0.6019	Remote Similarity	NPD5286	Approved
0.6019	Remote Similarity	NPD5285	Approved
0.6019	Remote Similarity	NPD4696	Approved
0.6018	Remote Similarity	NPD6012	Approved
0.6018	Remote Similarity	NPD6014	Approved
0.6018	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6647	Phase 2
0.6	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD8297	Approved
0.5982	Remote Similarity	NPD5701	Approved
0.5982	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4755	Approved
0.5981	Remote Similarity	NPD5173	Approved
0.598	Remote Similarity	NPD6903	Approved
0.598	Remote Similarity	NPD6672	Approved
0.598	Remote Similarity	NPD5737	Approved
0.598	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5368	Approved
0.5977	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5223	Approved
0.5962	Remote Similarity	NPD7637	Suspended
0.5957	Remote Similarity	NPD8039	Approved
0.5955	Remote Similarity	NPD3704	Approved
0.595	Remote Similarity	NPD6370	Approved
0.5943	Remote Similarity	NPD5210	Approved
0.5943	Remote Similarity	NPD5695	Phase 3
0.5943	Remote Similarity	NPD4629	Approved
0.5941	Remote Similarity	NPD4623	Approved
0.5941	Remote Similarity	NPD4519	Discontinued
0.5941	Remote Similarity	NPD5279	Phase 3
0.5941	Remote Similarity	NPD6422	Discontinued
0.5935	Remote Similarity	NPD7507	Approved
0.5932	Remote Similarity	NPD6009	Approved
0.593	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5696	Approved
0.5922	Remote Similarity	NPD4753	Phase 2
0.5917	Remote Similarity	NPD6059	Approved
0.5913	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5224	Approved
0.5909	Remote Similarity	NPD4633	Approved
0.5909	Remote Similarity	NPD5225	Approved
0.5909	Remote Similarity	NPD5226	Approved
0.5905	Remote Similarity	NPD4202	Approved
0.5902	Remote Similarity	NPD7830	Approved
0.5902	Remote Similarity	NPD7829	Approved
0.5902	Remote Similarity	NPD8328	Phase 3
0.5902	Remote Similarity	NPD7642	Approved
0.5889	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7641	Discontinued
0.5872	Remote Similarity	NPD4700	Approved
0.5872	Remote Similarity	NPD6648	Approved
0.5868	Remote Similarity	NPD6016	Approved
0.5868	Remote Similarity	NPD6015	Approved
0.5856	Remote Similarity	NPD5174	Approved
0.5856	Remote Similarity	NPD5175	Approved
0.5854	Remote Similarity	NPD7492	Approved
0.5849	Remote Similarity	NPD5282	Discontinued
0.5842	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7260	Phase 2
0.582	Remote Similarity	NPD7623	Phase 3
0.582	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.582	Remote Similarity	NPD5988	Approved
0.581	Remote Similarity	NPD5693	Phase 1
0.581	Remote Similarity	NPD5281	Approved
0.581	Remote Similarity	NPD5284	Approved
0.5806	Remote Similarity	NPD6616	Approved
0.5794	Remote Similarity	NPD7319	Approved
0.5789	Remote Similarity	NPD8264	Approved
0.5785	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6051	Approved
0.576	Remote Similarity	NPD7078	Approved
0.5752	Remote Similarity	NPD6008	Approved
0.575	Remote Similarity	NPD7327	Approved
0.575	Remote Similarity	NPD7328	Approved
0.575	Remote Similarity	NPD6335	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