NPASS Compound

Structure

NPC60765 OpenBabel07101718312D 28 30 0 0 1 0 0 0 0 0999 V2000 -3.7215 -3.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4253 -3.0984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5201 0.8483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0607 0.0071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5561 -1.2237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3163 0.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0619 -1.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3061 0.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4067 0.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3436 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -1.9010 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 -1.4067 -2.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3061 -2.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 -2.1235 0.0000 C 0 0 0 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3163 -2.7567 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0567 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0619 -0.0405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1740 -3.7465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0567 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2463 0.6828 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 16 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 15 2 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 23 1 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 17 24 1 6 0 0 0 18 22 2 0 0 0 0 19 25 1 1 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 24 5 1 6 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.23
Volume:	417.333
LogP:	4.032
LogD:	3.44
LogS:	-3.731
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.649
Synthetic Accessibility Score:	4.93
Fsp3:	0.542
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.702
MDCK Permeability:	2.3498510927311145e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.074
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.815
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	94.35941314697266%
Volume Distribution (VD):	0.302
Pgp-substrate:	1.0441899299621582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.148
CYP1A2-substrate:	0.874
CYP2C19-inhibitor:	0.409
CYP2C19-substrate:	0.742
CYP2C9-inhibitor:	0.448
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.729
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	3.139
Half-life (T1/2):	0.277

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.721
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.88
Carcinogencity:	0.042
Eye Corrosion:	0.004
Eye Irritation:	0.353
Respiratory Toxicity:	0.754

Download Data

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

Natural Product: NPC60765

Natural Product ID:	NPC60765
*Common Name:**	Epolone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	REJAHZFROGUZPE-CLMAGMTOSA-N
Standard InCHI:	InChI=1S/C24H32O4/c1-15-7-10-23(3,4)8-6-9-24(5)17(13-19(15)25)12-18-16(2)11-20(26)21(27)14-22(18)28-24/h6-8,11,14,17,19,25H,9-10,12-13H2,1-5H3,(H,26,27)/b8-6+,15-7+/t17-,19-,24-/m1/s1
SMILES:	C/C/1=CCC(C)(C)/C=C/C[C@@]2([C@@H](C[C@H]1O)Cc1c(O2)cc(c(=O)cc1C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513722
PubChem CID:	44575425
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004150] Hydrocarbon derivatives [CHEMONTID:0001650] Tropones [CHEMONTID:0001674] Tropolones

*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
NPO33026	os-f69284	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9644066]

☑ 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
Others	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
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Activity	=	1.5	uM	PMID[452447]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Activity	=	40.0	mU/ml	PMID[452447]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC90	>	40000.0	nM	PMID[452447]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	Ratio	=	22.0	n.a.	PMID[452447]

☑ 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 NPC60765 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	320
0.1-0.2	1306
0.2-0.3	3338
0.3-0.4	8315
0.4-0.5	10706
0.5-0.6	4636
0.6-0.7	9217
0.7-0.8	4809
0.8-0.85	43
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8617	High Similarity	NPC197447
0.8617	High Similarity	NPC169365
0.8132	Intermediate Similarity	NPC210216
0.8065	Intermediate Similarity	NPC189651
0.8065	Intermediate Similarity	NPC475098
0.8046	Intermediate Similarity	NPC112868
0.7865	Intermediate Similarity	NPC288281
0.7843	Intermediate Similarity	NPC228477
0.7843	Intermediate Similarity	NPC137911
0.7791	Intermediate Similarity	NPC315394
0.7791	Intermediate Similarity	NPC476007
0.7765	Intermediate Similarity	NPC474885
0.7717	Intermediate Similarity	NPC113370
0.7717	Intermediate Similarity	NPC476079
0.7717	Intermediate Similarity	NPC103743
0.77	Intermediate Similarity	NPC183570
0.766	Intermediate Similarity	NPC145666
0.7604	Intermediate Similarity	NPC65829
0.7604	Intermediate Similarity	NPC469491
0.7576	Intermediate Similarity	NPC227865
0.7576	Intermediate Similarity	NPC290802
0.7527	Intermediate Similarity	NPC199382
0.7525	Intermediate Similarity	NPC280566
0.75	Intermediate Similarity	NPC307112
0.75	Intermediate Similarity	NPC11804
0.75	Intermediate Similarity	NPC471223
0.75	Intermediate Similarity	NPC67081
0.7474	Intermediate Similarity	NPC212369
0.7473	Intermediate Similarity	NPC16488
0.7473	Intermediate Similarity	NPC161045
0.7473	Intermediate Similarity	NPC474809
0.7473	Intermediate Similarity	NPC475083
0.7451	Intermediate Similarity	NPC272632
0.7449	Intermediate Similarity	NPC288350
0.7449	Intermediate Similarity	NPC16967
0.7449	Intermediate Similarity	NPC173329
0.7444	Intermediate Similarity	NPC315731
0.7442	Intermediate Similarity	NPC144995
0.7442	Intermediate Similarity	NPC227814
0.7419	Intermediate Similarity	NPC315395
0.7419	Intermediate Similarity	NPC61527
0.7419	Intermediate Similarity	NPC316426
0.7416	Intermediate Similarity	NPC139712
0.7412	Intermediate Similarity	NPC95863
0.7396	Intermediate Similarity	NPC45579
0.7374	Intermediate Similarity	NPC202705
0.7374	Intermediate Similarity	NPC208094
0.7368	Intermediate Similarity	NPC307092
0.7368	Intermediate Similarity	NPC51358
0.7368	Intermediate Similarity	NPC212598
0.7347	Intermediate Similarity	NPC300710
0.734	Intermediate Similarity	NPC316138
0.734	Intermediate Similarity	NPC313658
0.7327	Intermediate Similarity	NPC469851
0.7312	Intermediate Similarity	NPC471795
0.7312	Intermediate Similarity	NPC470177
0.73	Intermediate Similarity	NPC166770
0.73	Intermediate Similarity	NPC475653
0.7294	Intermediate Similarity	NPC4299
0.7294	Intermediate Similarity	NPC286154
0.7292	Intermediate Similarity	NPC182136
0.7283	Intermediate Similarity	NPC23748
0.7283	Intermediate Similarity	NPC44261
0.7282	Intermediate Similarity	NPC309190
0.7273	Intermediate Similarity	NPC255410
0.7263	Intermediate Similarity	NPC7280
0.7263	Intermediate Similarity	NPC26078
0.7263	Intermediate Similarity	NPC260343
0.7263	Intermediate Similarity	NPC229612
0.7263	Intermediate Similarity	NPC473658
0.7253	Intermediate Similarity	NPC8538
0.7253	Intermediate Similarity	NPC475944
0.7253	Intermediate Similarity	NPC184208
0.7245	Intermediate Similarity	NPC166143
0.7245	Intermediate Similarity	NPC477241
0.7245	Intermediate Similarity	NPC191521
0.7245	Intermediate Similarity	NPC120351
0.7245	Intermediate Similarity	NPC471994
0.7241	Intermediate Similarity	NPC470686
0.7234	Intermediate Similarity	NPC311163
0.7234	Intermediate Similarity	NPC234038
0.7228	Intermediate Similarity	NPC185253
0.7228	Intermediate Similarity	NPC215253
0.7222	Intermediate Similarity	NPC471537
0.7212	Intermediate Similarity	NPC469852
0.7209	Intermediate Similarity	NPC474884
0.7209	Intermediate Similarity	NPC316185
0.7204	Intermediate Similarity	NPC160517
0.7204	Intermediate Similarity	NPC78673
0.7204	Intermediate Similarity	NPC186155
0.72	Intermediate Similarity	NPC120299
0.7196	Intermediate Similarity	NPC284162
0.7196	Intermediate Similarity	NPC255401
0.7195	Intermediate Similarity	NPC477456
0.7195	Intermediate Similarity	NPC477457
0.7191	Intermediate Similarity	NPC471225
0.7188	Intermediate Similarity	NPC471054
0.7188	Intermediate Similarity	NPC257485
0.7176	Intermediate Similarity	NPC101622
0.7176	Intermediate Similarity	NPC151481
0.7172	Intermediate Similarity	NPC295347
0.7172	Intermediate Similarity	NPC13924
0.7172	Intermediate Similarity	NPC91408
0.717	Intermediate Similarity	NPC75389
0.7159	Intermediate Similarity	NPC315552
0.7158	Intermediate Similarity	NPC478144
0.7158	Intermediate Similarity	NPC478145
0.7156	Intermediate Similarity	NPC82759
0.7143	Intermediate Similarity	NPC162615
0.7143	Intermediate Similarity	NPC59646
0.7143	Intermediate Similarity	NPC205034
0.7143	Intermediate Similarity	NPC474592
0.7143	Intermediate Similarity	NPC476049
0.7143	Intermediate Similarity	NPC152778
0.7143	Intermediate Similarity	NPC109406
0.7143	Intermediate Similarity	NPC469853
0.7129	Intermediate Similarity	NPC278673
0.7129	Intermediate Similarity	NPC316598
0.7128	Intermediate Similarity	NPC471494
0.7126	Intermediate Similarity	NPC316851
0.7113	Intermediate Similarity	NPC38952
0.7113	Intermediate Similarity	NPC3952
0.7113	Intermediate Similarity	NPC310479
0.7111	Intermediate Similarity	NPC231739
0.7111	Intermediate Similarity	NPC475994
0.7111	Intermediate Similarity	NPC326753
0.7111	Intermediate Similarity	NPC209135
0.7111	Intermediate Similarity	NPC474816
0.7111	Intermediate Similarity	NPC478122
0.7103	Intermediate Similarity	NPC181298
0.7103	Intermediate Similarity	NPC238850
0.71	Intermediate Similarity	NPC473153
0.71	Intermediate Similarity	NPC473291
0.7097	Intermediate Similarity	NPC49208
0.7093	Intermediate Similarity	NPC469660
0.7093	Intermediate Similarity	NPC315597
0.7093	Intermediate Similarity	NPC315285
0.7093	Intermediate Similarity	NPC59558
0.7093	Intermediate Similarity	NPC316029
0.7087	Intermediate Similarity	NPC197835
0.7087	Intermediate Similarity	NPC303653
0.7087	Intermediate Similarity	NPC473596
0.7087	Intermediate Similarity	NPC291500
0.7087	Intermediate Similarity	NPC140591
0.7087	Intermediate Similarity	NPC189609
0.7083	Intermediate Similarity	NPC106051
0.7075	Intermediate Similarity	NPC275060
0.7071	Intermediate Similarity	NPC470255
0.7071	Intermediate Similarity	NPC470521
0.7065	Intermediate Similarity	NPC474894
0.7065	Intermediate Similarity	NPC6663
0.7059	Intermediate Similarity	NPC117804
0.7053	Intermediate Similarity	NPC47220
0.7053	Intermediate Similarity	NPC116575
0.7053	Intermediate Similarity	NPC186332
0.7048	Intermediate Similarity	NPC266570
0.7048	Intermediate Similarity	NPC295843
0.7045	Intermediate Similarity	NPC315843
0.7041	Intermediate Similarity	NPC219874
0.7041	Intermediate Similarity	NPC476075
0.7041	Intermediate Similarity	NPC206679
0.7041	Intermediate Similarity	NPC476084
0.7041	Intermediate Similarity	NPC471324
0.7041	Intermediate Similarity	NPC114172
0.7041	Intermediate Similarity	NPC32552
0.7037	Intermediate Similarity	NPC471484
0.7037	Intermediate Similarity	NPC262083
0.7033	Intermediate Similarity	NPC226226
0.7033	Intermediate Similarity	NPC233295
0.7033	Intermediate Similarity	NPC55304
0.703	Intermediate Similarity	NPC134083
0.703	Intermediate Similarity	NPC239895
0.703	Intermediate Similarity	NPC53844
0.7021	Intermediate Similarity	NPC471302
0.7021	Intermediate Similarity	NPC471301
0.7021	Intermediate Similarity	NPC196487
0.7021	Intermediate Similarity	NPC14575
0.7019	Intermediate Similarity	NPC473144
0.7019	Intermediate Similarity	NPC473624
0.7019	Intermediate Similarity	NPC171014
0.7019	Intermediate Similarity	NPC297281
0.7011	Intermediate Similarity	NPC472254
0.701	Intermediate Similarity	NPC133450
0.701	Intermediate Similarity	NPC115179
0.701	Intermediate Similarity	NPC106040
0.7009	Intermediate Similarity	NPC475274
0.7009	Intermediate Similarity	NPC47951
0.7	Intermediate Similarity	NPC209355
0.7	Intermediate Similarity	NPC476439
0.7	Intermediate Similarity	NPC262747
0.7	Intermediate Similarity	NPC316324
0.7	Intermediate Similarity	NPC149550
0.7	Intermediate Similarity	NPC84360
0.7	Intermediate Similarity	NPC272050
0.7	Intermediate Similarity	NPC85105
0.6991	Remote Similarity	NPC19336
0.6991	Remote Similarity	NPC185876
0.699	Remote Similarity	NPC472637
0.699	Remote Similarity	NPC469657
0.699	Remote Similarity	NPC244456

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 NPC60765 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	924
0.2-0.3	1630
0.3-0.4	2544
0.4-0.5	2052
0.5-0.6	1189
0.6-0.7	431
0.7-0.8	94
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
0.6961	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7838	Discovery
0.6939	Remote Similarity	NPD5785	Approved
0.69	Remote Similarity	NPD5282	Discontinued
0.6842	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD8264	Approved
0.6774	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1696	Phase 3
0.6739	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6695	Phase 3
0.6731	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD6371	Approved
0.6632	Remote Similarity	NPD5209	Approved
0.663	Remote Similarity	NPD4756	Discovery
0.6596	Remote Similarity	NPD7514	Phase 3
0.6596	Remote Similarity	NPD7332	Phase 2
0.6562	Remote Similarity	NPD6110	Phase 1
0.6562	Remote Similarity	NPD7154	Phase 3
0.6535	Remote Similarity	NPD7637	Suspended
0.6484	Remote Similarity	NPD6926	Approved
0.6484	Remote Similarity	NPD6924	Approved
0.6476	Remote Similarity	NPD4225	Approved
0.6465	Remote Similarity	NPD7524	Approved
0.6465	Remote Similarity	NPD7750	Discontinued
0.6436	Remote Similarity	NPD46	Approved
0.6436	Remote Similarity	NPD6698	Approved
0.6429	Remote Similarity	NPD5363	Approved
0.6421	Remote Similarity	NPD4822	Approved
0.6421	Remote Similarity	NPD4695	Discontinued
0.6421	Remote Similarity	NPD4820	Approved
0.6421	Remote Similarity	NPD4821	Approved
0.6421	Remote Similarity	NPD6931	Approved
0.6421	Remote Similarity	NPD4819	Approved
0.6421	Remote Similarity	NPD6930	Phase 2
0.6421	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7145	Approved
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5279	Phase 3
0.6356	Remote Similarity	NPD7503	Approved
0.6354	Remote Similarity	NPD6902	Approved
0.6353	Remote Similarity	NPD368	Approved
0.6344	Remote Similarity	NPD6933	Approved
0.6333	Remote Similarity	NPD7144	Approved
0.6333	Remote Similarity	NPD7143	Approved
0.6322	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6929	Approved
0.6311	Remote Similarity	NPD5778	Approved
0.6311	Remote Similarity	NPD5779	Approved
0.63	Remote Similarity	NPD4251	Approved
0.63	Remote Similarity	NPD4250	Approved
0.6296	Remote Similarity	NPD5211	Phase 2
0.6293	Remote Similarity	NPD7115	Discovery
0.6277	Remote Similarity	NPD5776	Phase 2
0.6277	Remote Similarity	NPD6932	Approved
0.6277	Remote Similarity	NPD6925	Approved
0.6264	Remote Similarity	NPD7150	Approved
0.6264	Remote Similarity	NPD7152	Approved
0.6264	Remote Similarity	NPD7151	Approved
0.6263	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7639	Approved
0.6262	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7509	Discontinued
0.6237	Remote Similarity	NPD8039	Approved
0.6228	Remote Similarity	NPD6053	Discontinued
0.6224	Remote Similarity	NPD5362	Discontinued
0.6222	Remote Similarity	NPD6922	Approved
0.6222	Remote Similarity	NPD6923	Approved
0.6216	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6411	Approved
0.6214	Remote Similarity	NPD7983	Approved
0.6214	Remote Similarity	NPD7087	Discontinued
0.6211	Remote Similarity	NPD4271	Approved
0.6211	Remote Similarity	NPD4268	Approved
0.6207	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4249	Approved
0.6196	Remote Similarity	NPD4732	Discontinued
0.6186	Remote Similarity	NPD6898	Phase 1
0.6182	Remote Similarity	NPD5141	Approved
0.6168	Remote Similarity	NPD7638	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6132	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4270	Approved
0.6122	Remote Similarity	NPD4269	Approved
0.6122	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5285	Approved
0.6111	Remote Similarity	NPD5286	Approved
0.6111	Remote Similarity	NPD4696	Approved
0.61	Remote Similarity	NPD1694	Approved
0.61	Remote Similarity	NPD6893	Approved
0.6091	Remote Similarity	NPD6647	Phase 2
0.6075	Remote Similarity	NPD6084	Phase 2
0.6075	Remote Similarity	NPD6083	Phase 2
0.6071	Remote Similarity	NPD5697	Approved
0.6067	Remote Similarity	NPD3704	Approved
0.6067	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.6055	Remote Similarity	NPD5223	Approved
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.604	Remote Similarity	NPD5786	Approved
0.6038	Remote Similarity	NPD5210	Approved
0.6038	Remote Similarity	NPD4629	Approved
0.602	Remote Similarity	NPD5369	Approved
0.602	Remote Similarity	NPD4790	Discontinued
0.6019	Remote Similarity	NPD6101	Approved
0.6019	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4753	Phase 2
0.6019	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6686	Approved
0.6018	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6675	Approved
0.5982	Remote Similarity	NPD5739	Approved
0.5982	Remote Similarity	NPD7128	Approved
0.5982	Remote Similarity	NPD6402	Approved
0.5981	Remote Similarity	NPD5221	Approved
0.5981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7839	Suspended
0.5981	Remote Similarity	NPD5222	Approved
0.5979	Remote Similarity	NPD4195	Approved
0.5979	Remote Similarity	NPD6683	Phase 2
0.5977	Remote Similarity	NPD4192	Approved
0.5977	Remote Similarity	NPD4193	Approved
0.5977	Remote Similarity	NPD4194	Approved
0.5977	Remote Similarity	NPD4191	Approved
0.5965	Remote Similarity	NPD6013	Approved
0.5965	Remote Similarity	NPD6014	Approved
0.5965	Remote Similarity	NPD6012	Approved
0.596	Remote Similarity	NPD6435	Approved
0.5952	Remote Similarity	NPD4219	Approved
0.5948	Remote Similarity	NPD6882	Approved
0.5948	Remote Similarity	NPD8297	Approved
0.5946	Remote Similarity	NPD5175	Approved
0.5946	Remote Similarity	NPD5174	Approved
0.5926	Remote Similarity	NPD4755	Approved
0.5926	Remote Similarity	NPD5173	Approved
0.5918	Remote Similarity	NPD7525	Registered
0.5918	Remote Similarity	NPD4252	Approved
0.5909	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7260	Phase 2
0.5905	Remote Similarity	NPD6079	Approved
0.5889	Remote Similarity	NPD7331	Phase 2
0.5888	Remote Similarity	NPD5695	Phase 3
0.5882	Remote Similarity	NPD4623	Approved
0.5882	Remote Similarity	NPD5280	Approved
0.5882	Remote Similarity	NPD5690	Phase 2
0.5882	Remote Similarity	NPD4694	Approved
0.5882	Remote Similarity	NPD4519	Discontinued
0.5877	Remote Similarity	NPD7320	Approved
0.5865	Remote Similarity	NPD6051	Approved
0.5849	Remote Similarity	NPD6399	Phase 3
0.5842	Remote Similarity	NPD3666	Approved
0.5842	Remote Similarity	NPD4786	Approved
0.5842	Remote Similarity	NPD3133	Approved
0.5842	Remote Similarity	NPD3665	Phase 1
0.5841	Remote Similarity	NPD6640	Phase 3
0.5826	Remote Similarity	NPD6373	Approved
0.5826	Remote Similarity	NPD6372	Approved
0.5818	Remote Similarity	NPD4700	Approved
0.581	Remote Similarity	NPD7136	Phase 2
0.58	Remote Similarity	NPD3667	Approved
0.5794	Remote Similarity	NPD7748	Approved
0.5789	Remote Similarity	NPD5701	Approved
0.5784	Remote Similarity	NPD5329	Approved
0.578	Remote Similarity	NPD7902	Approved
0.5769	Remote Similarity	NPD5737	Approved
0.5769	Remote Similarity	NPD6672	Approved
0.5769	Remote Similarity	NPD4518	Approved
0.5758	Remote Similarity	NPD5368	Approved
0.5755	Remote Similarity	NPD5284	Approved
0.5755	Remote Similarity	NPD5694	Approved
0.5755	Remote Similarity	NPD5693	Phase 1
0.5755	Remote Similarity	NPD6050	Approved
0.5755	Remote Similarity	NPD7515	Phase 2
0.5755	Remote Similarity	NPD5281	Approved
0.575	Remote Similarity	NPD7500	Approved
0.575	Remote Similarity	NPD7505	Discontinued
0.5739	Remote Similarity	NPD4730	Approved
0.5739	Remote Similarity	NPD4729	Approved
0.5729	Remote Similarity	NPD6942	Approved
0.5729	Remote Similarity	NPD7339	Approved
0.5728	Remote Similarity	NPD3618	Phase 1

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