NPASS Compound

Structure

NPC59558 OpenBabel07101718312D 21 21 0 0 1 0 0 0 0 0999 V2000 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 -4.3301 -4.5000 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 -0.8660 -1.5000 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 1 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 6 1 0 0 0 0 2 10 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 11 3 1 6 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 1 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.17
Volume:	316.01
LogP:	2.348
LogD:	1.974
LogS:	-3.25
# Rotatable Bonds:	5
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.817
Synthetic Accessibility Score:	3.939
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.733
MDCK Permeability:	1.440002779418137e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.697
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	98.27281188964844%
Volume Distribution (VD):	1.159
Pgp-substrate:	4.031109809875488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.888
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.494
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.472
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.479
CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.276
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	5.767
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.638
Carcinogencity:	0.792
Eye Corrosion:	0.01
Eye Irritation:	0.195
Respiratory Toxicity:	0.346

Download Data

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

Natural Product: NPC59558

Natural Product ID:	NPC59558
*Common Name:**	Salinipyrone A
IUPAC Name:	4-hydroxy-6-[(1E,3E,5S,6R)-6-hydroxy-3,5-dimethylocta-1,3-dienyl]-3,5-dimethylpyran-2-one
Synonyms:
Standard InCHIKey:	ZAMAVOUZTQYUMR-MHQRDTTCSA-N
Standard InCHI:	InChI=1S/C17H24O4/c1-6-14(18)11(3)9-10(2)7-8-15-12(4)16(19)13(5)17(20)21-15/h7-9,11,14,18-19H,6H2,1-5H3/b8-7+,10-9+/t11-,14+/m0/s1
SMILES:	CC[C@H]([C@@H](C)/C=C(C)/C=C/c1c(C)c(c(C)c(=O)o1)O)O
Synthetic Gene Cluster:	BGC0001830;
ChEMBL Identifier:	CHEMBL465527
PubChem CID:	54733173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO6369	Salinispora pacifica	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18321059]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	50.0	%	PMID[475323]

☑ 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 NPC59558 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	279
0.1-0.2	1541
0.2-0.3	5166
0.3-0.4	10938
0.4-0.5	8184
0.5-0.6	6348
0.6-0.7	7927
0.7-0.8	2205
0.8-0.85	60
0.85-0.9	43
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8857	High Similarity	NPC316851
0.8657	High Similarity	NPC471566
0.8611	High Similarity	NPC315552
0.8451	Intermediate Similarity	NPC316185
0.8382	Intermediate Similarity	NPC471565
0.8378	Intermediate Similarity	NPC315394
0.8286	Intermediate Similarity	NPC238223
0.8219	Intermediate Similarity	NPC315843
0.8219	Intermediate Similarity	NPC470686
0.8169	Intermediate Similarity	NPC151481
0.8143	Intermediate Similarity	NPC132286
0.8116	Intermediate Similarity	NPC471556
0.8116	Intermediate Similarity	NPC273600
0.8116	Intermediate Similarity	NPC7940
0.8088	Intermediate Similarity	NPC2328
0.8	Intermediate Similarity	NPC315115
0.7973	Intermediate Similarity	NPC107654
0.7945	Intermediate Similarity	NPC178575
0.7941	Intermediate Similarity	NPC55376
0.7879	Intermediate Similarity	NPC135863
0.7826	Intermediate Similarity	NPC473737
0.7808	Intermediate Similarity	NPC473361
0.7808	Intermediate Similarity	NPC315597
0.7808	Intermediate Similarity	NPC329904
0.7808	Intermediate Similarity	NPC315285
0.7794	Intermediate Similarity	NPC130953
0.7794	Intermediate Similarity	NPC98519
0.7778	Intermediate Similarity	NPC313444
0.7761	Intermediate Similarity	NPC223679
0.7761	Intermediate Similarity	NPC254095
0.775	Intermediate Similarity	NPC16488
0.7746	Intermediate Similarity	NPC146811
0.7746	Intermediate Similarity	NPC470033
0.7746	Intermediate Similarity	NPC475555
0.7746	Intermediate Similarity	NPC475675
0.7727	Intermediate Similarity	NPC51846
0.7727	Intermediate Similarity	NPC221763
0.7692	Intermediate Similarity	NPC218486
0.7683	Intermediate Similarity	NPC315395
0.7683	Intermediate Similarity	NPC316426
0.7632	Intermediate Similarity	NPC478194
0.7632	Intermediate Similarity	NPC478195
0.7632	Intermediate Similarity	NPC478192
0.7632	Intermediate Similarity	NPC478191
0.7632	Intermediate Similarity	NPC478196
0.7632	Intermediate Similarity	NPC478193
0.7612	Intermediate Similarity	NPC249850
0.7612	Intermediate Similarity	NPC293437
0.7612	Intermediate Similarity	NPC129150
0.7606	Intermediate Similarity	NPC96414
0.7606	Intermediate Similarity	NPC282760
0.7568	Intermediate Similarity	NPC316029
0.7561	Intermediate Similarity	NPC471223
0.7561	Intermediate Similarity	NPC67081
0.7558	Intermediate Similarity	NPC282644
0.7558	Intermediate Similarity	NPC29798
0.7534	Intermediate Similarity	NPC474823
0.7534	Intermediate Similarity	NPC477117
0.7532	Intermediate Similarity	NPC470705
0.7531	Intermediate Similarity	NPC44261
0.75	Intermediate Similarity	NPC37382
0.75	Intermediate Similarity	NPC201356
0.75	Intermediate Similarity	NPC189700
0.7467	Intermediate Similarity	NPC293114
0.7463	Intermediate Similarity	NPC150717
0.7439	Intermediate Similarity	NPC161670
0.7432	Intermediate Similarity	NPC473277
0.7432	Intermediate Similarity	NPC475004
0.7429	Intermediate Similarity	NPC15193
0.7429	Intermediate Similarity	NPC26810
0.7407	Intermediate Similarity	NPC313677
0.7391	Intermediate Similarity	NPC82465
0.7391	Intermediate Similarity	NPC302564
0.7368	Intermediate Similarity	NPC284006
0.7361	Intermediate Similarity	NPC220766
0.7353	Intermediate Similarity	NPC294938
0.7342	Intermediate Similarity	NPC279532
0.7333	Intermediate Similarity	NPC476037
0.7333	Intermediate Similarity	NPC4299
0.7333	Intermediate Similarity	NPC202011
0.7324	Intermediate Similarity	NPC179087
0.7324	Intermediate Similarity	NPC210303
0.7324	Intermediate Similarity	NPC44343
0.7317	Intermediate Similarity	NPC315559
0.7308	Intermediate Similarity	NPC203277
0.7286	Intermediate Similarity	NPC309408
0.7284	Intermediate Similarity	NPC315731
0.7284	Intermediate Similarity	NPC112868
0.7273	Intermediate Similarity	NPC476590
0.7273	Intermediate Similarity	NPC114727
0.7262	Intermediate Similarity	NPC186332
0.7262	Intermediate Similarity	NPC47220
0.726	Intermediate Similarity	NPC191233
0.725	Intermediate Similarity	NPC271632
0.725	Intermediate Similarity	NPC139712
0.725	Intermediate Similarity	NPC99651
0.7246	Intermediate Similarity	NPC21946
0.7241	Intermediate Similarity	NPC32552
0.7237	Intermediate Similarity	NPC477087
0.7237	Intermediate Similarity	NPC477086
0.7229	Intermediate Similarity	NPC475706
0.7222	Intermediate Similarity	NPC471611
0.7215	Intermediate Similarity	NPC316324
0.7215	Intermediate Similarity	NPC471225
0.7215	Intermediate Similarity	NPC473825
0.7209	Intermediate Similarity	NPC307092
0.7209	Intermediate Similarity	NPC212598
0.7209	Intermediate Similarity	NPC51358
0.72	Intermediate Similarity	NPC470693
0.72	Intermediate Similarity	NPC101622
0.7179	Intermediate Similarity	NPC260396
0.7176	Intermediate Similarity	NPC316138
0.7176	Intermediate Similarity	NPC313658
0.7176	Intermediate Similarity	NPC45409
0.7164	Intermediate Similarity	NPC478120
0.7162	Intermediate Similarity	NPC122627
0.7143	Intermediate Similarity	NPC222852
0.7143	Intermediate Similarity	NPC133600
0.7143	Intermediate Similarity	NPC242233
0.7143	Intermediate Similarity	NPC97570
0.7143	Intermediate Similarity	NPC329890
0.7143	Intermediate Similarity	NPC477085
0.7143	Intermediate Similarity	NPC322186
0.7126	Intermediate Similarity	NPC327253
0.7125	Intermediate Similarity	NPC474816
0.7125	Intermediate Similarity	NPC93763
0.7125	Intermediate Similarity	NPC209135
0.7125	Intermediate Similarity	NPC108816
0.7123	Intermediate Similarity	NPC182794
0.7123	Intermediate Similarity	NPC478099
0.7123	Intermediate Similarity	NPC476589
0.7123	Intermediate Similarity	NPC478098
0.7123	Intermediate Similarity	NPC470123
0.7123	Intermediate Similarity	NPC19769
0.7121	Intermediate Similarity	NPC191643
0.7105	Intermediate Similarity	NPC476012
0.7101	Intermediate Similarity	NPC472445
0.7093	Intermediate Similarity	NPC26078
0.7093	Intermediate Similarity	NPC473658
0.7093	Intermediate Similarity	NPC260343
0.7093	Intermediate Similarity	NPC60765
0.7083	Intermediate Similarity	NPC68110
0.7073	Intermediate Similarity	NPC8538
0.7073	Intermediate Similarity	NPC184208
0.7067	Intermediate Similarity	NPC287705
0.7067	Intermediate Similarity	NPC79220
0.7067	Intermediate Similarity	NPC63873
0.7059	Intermediate Similarity	NPC173157
0.7059	Intermediate Similarity	NPC116575
0.7042	Intermediate Similarity	NPC476585
0.7042	Intermediate Similarity	NPC26223
0.7037	Intermediate Similarity	NPC471537
0.7013	Intermediate Similarity	NPC181587
0.7013	Intermediate Similarity	NPC472254
0.7	Intermediate Similarity	NPC116177
0.7	Intermediate Similarity	NPC320630
0.7	Intermediate Similarity	NPC475711
0.7	Intermediate Similarity	NPC7563
0.7	Intermediate Similarity	NPC262747
0.6988	Remote Similarity	NPC16321
0.6988	Remote Similarity	NPC324170
0.6988	Remote Similarity	NPC474439
0.6988	Remote Similarity	NPC474028
0.6977	Remote Similarity	NPC199382
0.6974	Remote Similarity	NPC236208
0.6974	Remote Similarity	NPC475982
0.697	Remote Similarity	NPC43053
0.6966	Remote Similarity	NPC59646
0.6966	Remote Similarity	NPC320552
0.6966	Remote Similarity	NPC159092
0.6966	Remote Similarity	NPC109406
0.6966	Remote Similarity	NPC476049
0.6962	Remote Similarity	NPC161038
0.6962	Remote Similarity	NPC147621
0.6962	Remote Similarity	NPC210258
0.6962	Remote Similarity	NPC206507
0.6957	Remote Similarity	NPC472808
0.6957	Remote Similarity	NPC324224
0.6941	Remote Similarity	NPC471494
0.6941	Remote Similarity	NPC474424
0.6933	Remote Similarity	NPC225272
0.6933	Remote Similarity	NPC478097
0.6932	Remote Similarity	NPC3436
0.6932	Remote Similarity	NPC182136
0.6932	Remote Similarity	NPC475879
0.6923	Remote Similarity	NPC185186
0.6923	Remote Similarity	NPC12815
0.6923	Remote Similarity	NPC327383
0.6923	Remote Similarity	NPC16967
0.6923	Remote Similarity	NPC238948
0.6923	Remote Similarity	NPC234084
0.6923	Remote Similarity	NPC126184
0.6923	Remote Similarity	NPC215745
0.6923	Remote Similarity	NPC329914
0.6914	Remote Similarity	NPC127526
0.6914	Remote Similarity	NPC264391
0.6914	Remote Similarity	NPC473471
0.6914	Remote Similarity	NPC315765
0.6914	Remote Similarity	NPC267231
0.6912	Remote Similarity	NPC474127

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 NPC59558 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	995
0.2-0.3	1964
0.3-0.4	2828
0.4-0.5	1855
0.5-0.6	960
0.6-0.7	254
0.7-0.8	55
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6923	Remote Similarity	NPD4220	Pre-registration
0.6824	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7838	Discovery
0.6706	Remote Similarity	NPD7154	Phase 3
0.6596	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4756	Discovery
0.6575	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4194	Approved
0.6486	Remote Similarity	NPD4193	Approved
0.6486	Remote Similarity	NPD4191	Approved
0.6486	Remote Similarity	NPD4192	Approved
0.6471	Remote Similarity	NPD6927	Phase 3
0.6447	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5209	Approved
0.6374	Remote Similarity	NPD46	Approved
0.6374	Remote Similarity	NPD6698	Approved
0.6353	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7637	Suspended
0.6292	Remote Similarity	NPD4249	Approved
0.6237	Remote Similarity	NPD5779	Approved
0.6237	Remote Similarity	NPD5778	Approved
0.6222	Remote Similarity	NPD4250	Approved
0.6222	Remote Similarity	NPD4251	Approved
0.6196	Remote Similarity	NPD5785	Approved
0.6136	Remote Similarity	NPD5362	Discontinued
0.6136	Remote Similarity	NPD6110	Phase 1
0.6129	Remote Similarity	NPD7983	Approved
0.6118	Remote Similarity	NPD4271	Approved
0.6118	Remote Similarity	NPD4268	Approved
0.6082	Remote Similarity	NPD4225	Approved
0.6081	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD1282	Approved
0.6042	Remote Similarity	NPD7839	Suspended
0.602	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5363	Approved
0.5977	Remote Similarity	NPD4819	Approved
0.5977	Remote Similarity	NPD4821	Approved
0.5977	Remote Similarity	NPD4252	Approved
0.5977	Remote Similarity	NPD4822	Approved
0.5977	Remote Similarity	NPD4820	Approved
0.596	Remote Similarity	NPD5344	Discontinued
0.5955	Remote Similarity	NPD5332	Approved
0.5955	Remote Similarity	NPD5331	Approved
0.5952	Remote Similarity	NPD8039	Approved
0.593	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD6101	Approved
0.5909	Remote Similarity	NPD4790	Discontinued
0.5867	Remote Similarity	NPD6109	Phase 1
0.5867	Remote Similarity	NPD9119	Approved
0.5867	Remote Similarity	NPD69	Approved
0.5859	Remote Similarity	NPD7639	Approved
0.5859	Remote Similarity	NPD7640	Approved
0.5843	Remote Similarity	NPD4269	Approved
0.5843	Remote Similarity	NPD4270	Approved
0.5842	Remote Similarity	NPD6647	Phase 2
0.5811	Remote Similarity	NPD4219	Approved
0.5795	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6411	Approved
0.5773	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD8264	Approved
0.5761	Remote Similarity	NPD5786	Approved
0.5758	Remote Similarity	NPD7638	Approved
0.5745	Remote Similarity	NPD689	Discontinued
0.5735	Remote Similarity	NPD4265	Approved
0.5733	Remote Similarity	NPD9118	Approved
0.5733	Remote Similarity	NPD8779	Phase 3
0.5714	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4732	Discontinued
0.5701	Remote Similarity	NPD6053	Discontinued
0.5672	Remote Similarity	NPD9411	Phase 1
0.5667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD368	Approved
0.5631	Remote Similarity	NPD5909	Discontinued
0.5625	Remote Similarity	NPD4810	Clinical (unspecified phase)

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