NPASS Compound

Structure

NPC273600 OpenBabel07101719522D 21 21 0 0 1 0 0 0 0 0999 V2000 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 4.5000 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 1.7321 1.0000 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 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 9 1 0 0 0 0 4 9 2 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 3 1 6 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 1 0 0 0 12 6 1 1 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 1 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.13
Volume:	298.999
LogP:	0.825
LogD:	1.179
LogS:	-1.721
# Rotatable Bonds:	6
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	4.685
Fsp3:	0.467
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:	-4.715
MDCK Permeability:	4.038173210574314e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.096
Human Intestinal Absorption (HIA):	0.865
20% Bioavailability (F20%):	0.173
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.923
Plasma Protein Binding (PPB):	71.611083984375%
Volume Distribution (VD):	0.306
Pgp-substrate:	23.07546615600586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.387
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.118
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	7.132
Half-life (T1/2):	0.854

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.647
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.714
Carcinogencity:	0.494
Eye Corrosion:	0.023
Eye Irritation:	0.046
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC273600

Natural Product ID:	NPC273600
*Common Name:**	Phomopsolide B
IUPAC Name:	[(2S,3S)-2-[(E,3S,4S)-3,4-dihydroxypent-1-enyl]-6-oxo-2,3-dihydropyran-3-yl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	JTHHOHSDOJJNFN-HIWLEQICSA-N
Standard InCHI:	InChI=1S/C15H20O6/c1-4-9(2)15(19)21-13-7-8-14(18)20-12(13)6-5-11(17)10(3)16/h4-8,10-13,16-17H,1-3H3/b6-5+,9-4+/t10-,11-,12-,13-/m0/s1
SMILES:	C/C=C(/C(=O)O[C@H]1C=CC(=O)O[C@H]1/C=C/[C@@H]([C@@H](O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464205
PubChem CID:	6442165
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	20.0	mm	PMID[489173]

☑ 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 NPC273600 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	171
0.1-0.2	2895
0.2-0.3	10301
0.3-0.4	18661
0.4-0.5	7117
0.5-0.6	2625
0.6-0.7	775
0.7-0.8	133
0.8-0.85	10
0.85-0.9	5
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9206	High Similarity	NPC475555
0.9206	High Similarity	NPC475675
0.9167	High Similarity	NPC302564
0.8906	High Similarity	NPC201356
0.875	High Similarity	NPC96414
0.8657	High Similarity	NPC202011
0.8462	Intermediate Similarity	NPC19769
0.8235	Intermediate Similarity	NPC475982
0.8226	Intermediate Similarity	NPC135863
0.8194	Intermediate Similarity	NPC475711
0.8116	Intermediate Similarity	NPC59558
0.8095	Intermediate Similarity	NPC223679
0.8095	Intermediate Similarity	NPC254095
0.8056	Intermediate Similarity	NPC203277
0.8056	Intermediate Similarity	NPC470705
0.7937	Intermediate Similarity	NPC129150
0.7937	Intermediate Similarity	NPC249850
0.7937	Intermediate Similarity	NPC293437
0.791	Intermediate Similarity	NPC470123
0.7879	Intermediate Similarity	NPC2328
0.7879	Intermediate Similarity	NPC473737
0.7846	Intermediate Similarity	NPC26223
0.7838	Intermediate Similarity	NPC279532
0.7838	Intermediate Similarity	NPC28049
0.7794	Intermediate Similarity	NPC276299
0.7778	Intermediate Similarity	NPC230296
0.7778	Intermediate Similarity	NPC315843
0.7778	Intermediate Similarity	NPC107654
0.7761	Intermediate Similarity	NPC470808
0.7727	Intermediate Similarity	NPC26810
0.7714	Intermediate Similarity	NPC151481
0.7692	Intermediate Similarity	NPC97570
0.7692	Intermediate Similarity	NPC82465
0.7681	Intermediate Similarity	NPC122627
0.7671	Intermediate Similarity	NPC478196
0.7671	Intermediate Similarity	NPC478193
0.7671	Intermediate Similarity	NPC161038
0.7671	Intermediate Similarity	NPC478194
0.7671	Intermediate Similarity	NPC478195
0.7671	Intermediate Similarity	NPC478191
0.7671	Intermediate Similarity	NPC478192
0.7667	Intermediate Similarity	NPC275316
0.7667	Intermediate Similarity	NPC15789
0.7656	Intermediate Similarity	NPC294938
0.7647	Intermediate Similarity	NPC478099
0.7647	Intermediate Similarity	NPC282760
0.7647	Intermediate Similarity	NPC478098
0.7632	Intermediate Similarity	NPC121374
0.7612	Intermediate Similarity	NPC475073
0.76	Intermediate Similarity	NPC248775
0.76	Intermediate Similarity	NPC473471
0.7576	Intermediate Similarity	NPC98519
0.7576	Intermediate Similarity	NPC130953
0.7571	Intermediate Similarity	NPC238223
0.7571	Intermediate Similarity	NPC63873
0.7568	Intermediate Similarity	NPC127118
0.7568	Intermediate Similarity	NPC301207
0.7568	Intermediate Similarity	NPC209113
0.7564	Intermediate Similarity	NPC44261
0.7538	Intermediate Similarity	NPC21946
0.7536	Intermediate Similarity	NPC146811
0.7536	Intermediate Similarity	NPC478101
0.75	Intermediate Similarity	NPC316185
0.75	Intermediate Similarity	NPC470148
0.75	Intermediate Similarity	NPC148233
0.75	Intermediate Similarity	NPC180725
0.75	Intermediate Similarity	NPC470149
0.75	Intermediate Similarity	NPC25747
0.75	Intermediate Similarity	NPC308457
0.75	Intermediate Similarity	NPC51846
0.7467	Intermediate Similarity	NPC125365
0.7467	Intermediate Similarity	NPC474818
0.7467	Intermediate Similarity	NPC176329
0.7467	Intermediate Similarity	NPC51809
0.7467	Intermediate Similarity	NPC49302
0.7467	Intermediate Similarity	NPC474026
0.7467	Intermediate Similarity	NPC275530
0.7463	Intermediate Similarity	NPC55376
0.7429	Intermediate Similarity	NPC478100
0.7429	Intermediate Similarity	NPC478097
0.7429	Intermediate Similarity	NPC132286
0.7403	Intermediate Similarity	NPC133226
0.7403	Intermediate Similarity	NPC470147
0.7391	Intermediate Similarity	NPC471566
0.7391	Intermediate Similarity	NPC471565
0.7377	Intermediate Similarity	NPC236338
0.7368	Intermediate Similarity	NPC279214
0.7368	Intermediate Similarity	NPC221095
0.7368	Intermediate Similarity	NPC318481
0.7353	Intermediate Similarity	NPC68110
0.7342	Intermediate Similarity	NPC161045
0.7342	Intermediate Similarity	NPC315559
0.7324	Intermediate Similarity	NPC474823
0.7308	Intermediate Similarity	NPC297440
0.7297	Intermediate Similarity	NPC476590
0.7297	Intermediate Similarity	NPC114727
0.7286	Intermediate Similarity	NPC124586
0.7286	Intermediate Similarity	NPC37382
0.7273	Intermediate Similarity	NPC99651
0.7273	Intermediate Similarity	NPC189700
0.726	Intermediate Similarity	NPC293114
0.725	Intermediate Similarity	NPC161670
0.725	Intermediate Similarity	NPC475035
0.725	Intermediate Similarity	NPC474251
0.7231	Intermediate Similarity	NPC221763
0.7231	Intermediate Similarity	NPC150717
0.7222	Intermediate Similarity	NPC475004
0.7215	Intermediate Similarity	NPC310450
0.7215	Intermediate Similarity	NPC11383
0.7215	Intermediate Similarity	NPC313677
0.7215	Intermediate Similarity	NPC475046
0.7215	Intermediate Similarity	NPC474959
0.7188	Intermediate Similarity	NPC218486
0.7183	Intermediate Similarity	NPC25298
0.7164	Intermediate Similarity	NPC322186
0.7164	Intermediate Similarity	NPC159650
0.7164	Intermediate Similarity	NPC22897
0.7162	Intermediate Similarity	NPC284006
0.7162	Intermediate Similarity	NPC185186
0.7162	Intermediate Similarity	NPC327383
0.7162	Intermediate Similarity	NPC316851
0.716	Intermediate Similarity	NPC475034
0.716	Intermediate Similarity	NPC470124
0.716	Intermediate Similarity	NPC11804
0.7143	Intermediate Similarity	NPC7940
0.7143	Intermediate Similarity	NPC476586
0.7143	Intermediate Similarity	NPC471556
0.7143	Intermediate Similarity	NPC476589
0.7143	Intermediate Similarity	NPC477314
0.7125	Intermediate Similarity	NPC229799
0.7125	Intermediate Similarity	NPC286770
0.7125	Intermediate Similarity	NPC284472
0.7123	Intermediate Similarity	NPC473361
0.7123	Intermediate Similarity	NPC329904
0.7123	Intermediate Similarity	NPC476037
0.7121	Intermediate Similarity	NPC71755
0.7101	Intermediate Similarity	NPC179087
0.7101	Intermediate Similarity	NPC210303
0.7101	Intermediate Similarity	NPC476584
0.7101	Intermediate Similarity	NPC44343
0.7089	Intermediate Similarity	NPC150502
0.7083	Intermediate Similarity	NPC310210
0.7083	Intermediate Similarity	NPC475760
0.7067	Intermediate Similarity	NPC474545
0.7059	Intermediate Similarity	NPC79756
0.7059	Intermediate Similarity	NPC309408
0.7051	Intermediate Similarity	NPC1180
0.7031	Intermediate Similarity	NPC477781
0.7031	Intermediate Similarity	NPC477780
0.7027	Intermediate Similarity	NPC178575
0.7015	Intermediate Similarity	NPC474084
0.7013	Intermediate Similarity	NPC315394
0.7013	Intermediate Similarity	NPC474278
0.6988	Remote Similarity	NPC475037
0.6986	Remote Similarity	NPC130618
0.6984	Remote Similarity	NPC43053
0.6974	Remote Similarity	NPC285840
0.6974	Remote Similarity	NPC473948
0.6974	Remote Similarity	NPC473582
0.6974	Remote Similarity	NPC327041
0.6974	Remote Similarity	NPC260396
0.6974	Remote Similarity	NPC315552
0.697	Remote Similarity	NPC472808
0.697	Remote Similarity	NPC324224
0.6957	Remote Similarity	NPC151648
0.6957	Remote Similarity	NPC263732
0.6951	Remote Similarity	NPC471494
0.6951	Remote Similarity	NPC182383
0.6944	Remote Similarity	NPC203335
0.6941	Remote Similarity	NPC3952
0.6933	Remote Similarity	NPC329890
0.6923	Remote Similarity	NPC478120
0.6923	Remote Similarity	NPC474127
0.6914	Remote Similarity	NPC16488
0.6914	Remote Similarity	NPC253801
0.6914	Remote Similarity	NPC142111
0.6914	Remote Similarity	NPC473315
0.6912	Remote Similarity	NPC286189
0.6901	Remote Similarity	NPC182794
0.6892	Remote Similarity	NPC476012
0.6883	Remote Similarity	NPC326661
0.6883	Remote Similarity	NPC68819
0.6875	Remote Similarity	NPC191643
0.6875	Remote Similarity	NPC474980
0.6867	Remote Similarity	NPC69082
0.6867	Remote Similarity	NPC316426
0.6867	Remote Similarity	NPC311163
0.6867	Remote Similarity	NPC47937
0.6867	Remote Similarity	NPC279267
0.6867	Remote Similarity	NPC315395
0.6866	Remote Similarity	NPC212730
0.6866	Remote Similarity	NPC265551
0.6866	Remote Similarity	NPC283502
0.6849	Remote Similarity	NPC477117
0.6842	Remote Similarity	NPC326504
0.6842	Remote Similarity	NPC474280
0.6842	Remote Similarity	NPC473489
0.6835	Remote Similarity	NPC139712
0.6835	Remote Similarity	NPC475210
0.6829	Remote Similarity	NPC473308

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 NPC273600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	3015
0.2-0.3	4134
0.3-0.4	1523
0.4-0.5	257
0.5-0.6	67
0.6-0.7	12
0.7-0.8	0
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
0.7015	Intermediate Similarity	NPD585	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD69	Approved
0.6765	Remote Similarity	NPD9119	Approved
0.6618	Remote Similarity	NPD9118	Approved
0.6552	Remote Similarity	NPD7838	Discovery
0.6522	Remote Similarity	NPD6109	Phase 1
0.6462	Remote Similarity	NPD6927	Phase 3
0.6429	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4220	Pre-registration
0.6364	Remote Similarity	NPD6698	Approved
0.6364	Remote Similarity	NPD46	Approved
0.6237	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4225	Approved
0.6129	Remote Similarity	NPD9411	Phase 1
0.6111	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5344	Discontinued
0.6053	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD4756	Discovery
0.5824	Remote Similarity	NPD5785	Approved
0.5811	Remote Similarity	NPD9418	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD6096	Approved
0.5781	Remote Similarity	NPD6097	Approved
0.5765	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7983	Approved
0.5747	Remote Similarity	NPD7154	Phase 3
0.5747	Remote Similarity	NPD205	Approved
0.5747	Remote Similarity	NPD6110	Phase 1
0.5692	Remote Similarity	NPD4265	Approved
0.5692	Remote Similarity	NPD9090	Phase 3
0.5684	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.567	Remote Similarity	NPD6648	Approved
0.5667	Remote Similarity	NPD9115	Approved
0.5658	Remote Similarity	NPD3197	Phase 1
0.5658	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD5209	Approved
0.5625	Remote Similarity	NPD5326	Phase 3
0.5618	Remote Similarity	NPD5363	Approved
0.5607	Remote Similarity	NPD7115	Discovery
0.56	Remote Similarity	NPD4192	Approved
0.56	Remote Similarity	NPD4191	Approved
0.56	Remote Similarity	NPD4193	Approved
0.56	Remote Similarity	NPD4194	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