NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.17
Volume:	271.981
LogP:	1.011
LogD:	1.148
LogS:	-0.952
# Rotatable Bonds:	3
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	4.77
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.567
MDCK Permeability:	7.752103556413203e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.615
Plasma Protein Binding (PPB):	56.732749938964844%
Volume Distribution (VD):	1.217
Pgp-substrate:	39.67109680175781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.79
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.861
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.196
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.403
CYP3A4-substrate:	0.464

ADMET: Excretion

Clearance (CL):	6.051
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.596
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.663
Skin Sensitization:	0.561
Carcinogencity:	0.396
Eye Corrosion:	0.469
Eye Irritation:	0.469
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC310608

Natural Product ID:	NPC310608
*Common Name:**	14-Hydroxy-5-Desoxy-2S,3S,9R-Illudosin
IUPAC Name:	(2E)-2-[(2S)-2-[(1S,2R,4S)-2-hydroxy-4-(hydroxymethyl)-4-methylcyclopentyl]-2-methylcyclobutylidene]propanal
Synonyms:
Standard InCHIKey:	AXEKOLRQAGIULX-JPPPHGFVSA-N
Standard InCHI:	InChI=1S/C15H24O3/c1-10(8-16)11-4-5-15(11,3)12-6-14(2,9-17)7-13(12)18/h8,12-13,17-18H,4-7,9H2,1-3H3/b11-10+/t12-,13-,14+,15-/m1/s1
SMILES:	C/C(=C1/CC[C@@]1(C)[C@@H]1C[C@@](C)(C[C@H]1O)CO)/C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172013
PubChem CID:	49798952
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols [CHEMONTID:0002938] Cyclopentanols

*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
NPO33262	coprinus cinereus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919060]
NPO33262	coprinus cinereus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20598551]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	5.3	ug ml-1	PMID[454974]

☑ 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 NPC310608 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	195
0.1-0.2	2115
0.2-0.3	11801
0.3-0.4	13788
0.4-0.5	8552
0.5-0.6	5669
0.6-0.7	562
0.7-0.8	13
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7927	Intermediate Similarity	NPC232156
0.76	Intermediate Similarity	NPC254845
0.75	Intermediate Similarity	NPC181195
0.75	Intermediate Similarity	NPC261125
0.7407	Intermediate Similarity	NPC471656
0.7397	Intermediate Similarity	NPC238352
0.7397	Intermediate Similarity	NPC477009
0.7342	Intermediate Similarity	NPC215481
0.7273	Intermediate Similarity	NPC41886
0.725	Intermediate Similarity	NPC276769
0.7241	Intermediate Similarity	NPC97032
0.7222	Intermediate Similarity	NPC63111
0.7176	Intermediate Similarity	NPC36350
0.7176	Intermediate Similarity	NPC280203
0.7162	Intermediate Similarity	NPC61503
0.7143	Intermediate Similarity	NPC474748
0.7143	Intermediate Similarity	NPC471781
0.7126	Intermediate Similarity	NPC477710
0.7125	Intermediate Similarity	NPC124289
0.7125	Intermediate Similarity	NPC473437
0.7125	Intermediate Similarity	NPC142759
0.7125	Intermediate Similarity	NPC141346
0.7125	Intermediate Similarity	NPC126969
0.7125	Intermediate Similarity	NPC310643
0.7125	Intermediate Similarity	NPC25908
0.7125	Intermediate Similarity	NPC115719
0.7089	Intermediate Similarity	NPC78527
0.7073	Intermediate Similarity	NPC470429
0.7059	Intermediate Similarity	NPC16887
0.7059	Intermediate Similarity	NPC53011
0.7059	Intermediate Similarity	NPC37005
0.7059	Intermediate Similarity	NPC154893
0.7045	Intermediate Similarity	NPC257485
0.7045	Intermediate Similarity	NPC232747
0.7037	Intermediate Similarity	NPC470428
0.7037	Intermediate Similarity	NPC211279
0.7027	Intermediate Similarity	NPC309300
0.7024	Intermediate Similarity	NPC472465
0.7024	Intermediate Similarity	NPC133844
0.6974	Remote Similarity	NPC477791
0.6966	Remote Similarity	NPC477711
0.6962	Remote Similarity	NPC234527
0.6962	Remote Similarity	NPC14352
0.6951	Remote Similarity	NPC321180
0.6951	Remote Similarity	NPC476949
0.6941	Remote Similarity	NPC472473
0.6933	Remote Similarity	NPC474329
0.6933	Remote Similarity	NPC261782
0.6933	Remote Similarity	NPC474304
0.6933	Remote Similarity	NPC469326
0.6933	Remote Similarity	NPC205618
0.6933	Remote Similarity	NPC300442
0.6923	Remote Similarity	NPC111015
0.6923	Remote Similarity	NPC298919
0.6914	Remote Similarity	NPC469646
0.6914	Remote Similarity	NPC472472
0.6905	Remote Similarity	NPC6434
0.6883	Remote Similarity	NPC167527
0.6875	Remote Similarity	NPC102313
0.6875	Remote Similarity	NPC199316
0.6867	Remote Similarity	NPC229204
0.686	Remote Similarity	NPC227064
0.686	Remote Similarity	NPC161423
0.686	Remote Similarity	NPC329043
0.686	Remote Similarity	NPC321187
0.686	Remote Similarity	NPC58841
0.6848	Remote Similarity	NPC37408
0.6848	Remote Similarity	NPC469873
0.6835	Remote Similarity	NPC469343
0.6829	Remote Similarity	NPC186109
0.6824	Remote Similarity	NPC470614
0.6824	Remote Similarity	NPC1272
0.6818	Remote Similarity	NPC89747
0.6818	Remote Similarity	NPC475772
0.6813	Remote Similarity	NPC250575
0.6795	Remote Similarity	NPC144647
0.6795	Remote Similarity	NPC22301
0.679	Remote Similarity	NPC113639
0.679	Remote Similarity	NPC114236
0.679	Remote Similarity	NPC77501
0.679	Remote Similarity	NPC251435
0.679	Remote Similarity	NPC313185
0.6786	Remote Similarity	NPC26117
0.6778	Remote Similarity	NPC472466
0.6753	Remote Similarity	NPC136813
0.675	Remote Similarity	NPC474140
0.6744	Remote Similarity	NPC110778
0.6744	Remote Similarity	NPC477667
0.6744	Remote Similarity	NPC477818
0.6744	Remote Similarity	NPC62214
0.6712	Remote Similarity	NPC52431
0.6712	Remote Similarity	NPC310228
0.6711	Remote Similarity	NPC471200
0.6709	Remote Similarity	NPC470041
0.6709	Remote Similarity	NPC280256
0.6709	Remote Similarity	NPC133873
0.6707	Remote Similarity	NPC250621
0.6706	Remote Similarity	NPC136150
0.6706	Remote Similarity	NPC472471
0.6705	Remote Similarity	NPC477668
0.6705	Remote Similarity	NPC212843
0.6703	Remote Similarity	NPC472468
0.6703	Remote Similarity	NPC473675
0.6702	Remote Similarity	NPC477949
0.6667	Remote Similarity	NPC471659
0.6667	Remote Similarity	NPC124172
0.6667	Remote Similarity	NPC214043
0.6667	Remote Similarity	NPC473759
0.6667	Remote Similarity	NPC329435
0.6667	Remote Similarity	NPC41217
0.6667	Remote Similarity	NPC473246
0.6667	Remote Similarity	NPC211291
0.6667	Remote Similarity	NPC133368
0.6667	Remote Similarity	NPC33913
0.6667	Remote Similarity	NPC477943
0.6667	Remote Similarity	NPC186688
0.6667	Remote Similarity	NPC469608
0.6667	Remote Similarity	NPC170775
0.6667	Remote Similarity	NPC82902
0.6667	Remote Similarity	NPC470299
0.6667	Remote Similarity	NPC85774
0.6667	Remote Similarity	NPC472265
0.6667	Remote Similarity	NPC258231
0.6667	Remote Similarity	NPC474155
0.6667	Remote Similarity	NPC224532
0.6667	Remote Similarity	NPC309178
0.6633	Remote Similarity	NPC470838
0.663	Remote Similarity	NPC125180
0.663	Remote Similarity	NPC109414
0.6629	Remote Similarity	NPC471657
0.6629	Remote Similarity	NPC312215
0.6629	Remote Similarity	NPC45957
0.6627	Remote Similarity	NPC476007
0.6627	Remote Similarity	NPC197659
0.6627	Remote Similarity	NPC86917
0.6625	Remote Similarity	NPC469737
0.6625	Remote Similarity	NPC471662
0.6622	Remote Similarity	NPC252809
0.6593	Remote Similarity	NPC2946
0.6593	Remote Similarity	NPC191684
0.6593	Remote Similarity	NPC183283
0.6591	Remote Similarity	NPC179006
0.6591	Remote Similarity	NPC197823
0.6591	Remote Similarity	NPC474218
0.6591	Remote Similarity	NPC474853
0.6591	Remote Similarity	NPC245434
0.6588	Remote Similarity	NPC471514
0.6588	Remote Similarity	NPC45495
0.6585	Remote Similarity	NPC60818
0.6585	Remote Similarity	NPC23231
0.6585	Remote Similarity	NPC328104
0.6585	Remote Similarity	NPC319090
0.6585	Remote Similarity	NPC474885
0.6585	Remote Similarity	NPC263698
0.6585	Remote Similarity	NPC474011
0.6582	Remote Similarity	NPC90115
0.6582	Remote Similarity	NPC217570
0.6579	Remote Similarity	NPC219940
0.6562	Remote Similarity	NPC154072
0.6559	Remote Similarity	NPC90453
0.6559	Remote Similarity	NPC472467
0.6556	Remote Similarity	NPC476704
0.6556	Remote Similarity	NPC183546
0.6556	Remote Similarity	NPC48866
0.6556	Remote Similarity	NPC247406
0.6556	Remote Similarity	NPC291665
0.6556	Remote Similarity	NPC294480
0.6552	Remote Similarity	NPC141941
0.6552	Remote Similarity	NPC321385
0.6552	Remote Similarity	NPC193870
0.6548	Remote Similarity	NPC477817
0.6548	Remote Similarity	NPC472502
0.6548	Remote Similarity	NPC477819
0.6548	Remote Similarity	NPC475
0.6548	Remote Similarity	NPC477514
0.6548	Remote Similarity	NPC475980
0.6548	Remote Similarity	NPC477522
0.6548	Remote Similarity	NPC87604
0.6543	Remote Similarity	NPC300940
0.6533	Remote Similarity	NPC260573
0.6533	Remote Similarity	NPC15152
0.6522	Remote Similarity	NPC233116
0.6517	Remote Similarity	NPC31564
0.6517	Remote Similarity	NPC201273
0.6517	Remote Similarity	NPC474732
0.6517	Remote Similarity	NPC469994
0.6517	Remote Similarity	NPC145879
0.6517	Remote Similarity	NPC94755
0.6517	Remote Similarity	NPC474778
0.6517	Remote Similarity	NPC474733
0.6517	Remote Similarity	NPC24277
0.6517	Remote Similarity	NPC327115
0.6517	Remote Similarity	NPC72133
0.6512	Remote Similarity	NPC471661
0.6506	Remote Similarity	NPC1973
0.6506	Remote Similarity	NPC471658
0.6506	Remote Similarity	NPC167873
0.6506	Remote Similarity	NPC470525
0.6506	Remote Similarity	NPC263582
0.6506	Remote Similarity	NPC96319

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 NPC310608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	2916
0.2-0.3	4242
0.3-0.4	1274
0.4-0.5	236
0.5-0.6	257
0.6-0.7	21
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
0.686	Remote Similarity	NPD3665	Phase 1
0.686	Remote Similarity	NPD3666	Approved
0.686	Remote Similarity	NPD3133	Approved
0.663	Remote Similarity	NPD4202	Approved
0.6517	Remote Similarity	NPD5279	Phase 3
0.6506	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4753	Phase 2
0.6471	Remote Similarity	NPD4195	Approved
0.6471	Remote Similarity	NPD6929	Approved
0.6463	Remote Similarity	NPD6924	Approved
0.6463	Remote Similarity	NPD6926	Approved
0.6437	Remote Similarity	NPD4223	Phase 3
0.6437	Remote Similarity	NPD4221	Approved
0.6395	Remote Similarity	NPD6931	Approved
0.6395	Remote Similarity	NPD4748	Discontinued
0.6395	Remote Similarity	NPD6930	Phase 2
0.6354	Remote Similarity	NPD4755	Approved
0.6333	Remote Similarity	NPD3618	Phase 1
0.631	Remote Similarity	NPD6933	Approved
0.6304	Remote Similarity	NPD5328	Approved
0.6292	Remote Similarity	NPD4786	Approved
0.6292	Remote Similarity	NPD4197	Approved
0.6292	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD3667	Approved
0.6235	Remote Similarity	NPD6932	Approved
0.6235	Remote Similarity	NPD6925	Approved
0.6235	Remote Similarity	NPD5776	Phase 2
0.6224	Remote Similarity	NPD5285	Approved
0.6224	Remote Similarity	NPD5286	Approved
0.6224	Remote Similarity	NPD4700	Approved
0.6224	Remote Similarity	NPD4696	Approved
0.6222	Remote Similarity	NPD5329	Approved
0.6222	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4821	Approved
0.6207	Remote Similarity	NPD7525	Registered
0.6207	Remote Similarity	NPD4819	Approved
0.6207	Remote Similarity	NPD4822	Approved
0.6207	Remote Similarity	NPD5368	Approved
0.6207	Remote Similarity	NPD4820	Approved
0.619	Remote Similarity	NPD6942	Approved
0.619	Remote Similarity	NPD7339	Approved
0.618	Remote Similarity	NPD5362	Discontinued
0.618	Remote Similarity	NPD6695	Phase 3
0.618	Remote Similarity	NPD5331	Approved
0.618	Remote Similarity	NPD5332	Approved
0.618	Remote Similarity	NPD4788	Approved
0.6173	Remote Similarity	NPD6923	Approved
0.6173	Remote Similarity	NPD6922	Approved
0.617	Remote Similarity	NPD6079	Approved
0.6163	Remote Similarity	NPD7145	Approved
0.6163	Remote Similarity	NPD4271	Approved
0.6163	Remote Similarity	NPD4268	Approved
0.6163	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD3617	Approved
0.6162	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD5280	Approved
0.6154	Remote Similarity	NPD4688	Approved
0.6154	Remote Similarity	NPD4693	Phase 3
0.6154	Remote Similarity	NPD4689	Approved
0.6154	Remote Similarity	NPD4690	Approved
0.6154	Remote Similarity	NPD5205	Approved
0.6154	Remote Similarity	NPD5690	Phase 2
0.6154	Remote Similarity	NPD4138	Approved
0.6154	Remote Similarity	NPD4694	Approved
0.6146	Remote Similarity	NPD4629	Approved
0.6146	Remote Similarity	NPD5210	Approved
0.6136	Remote Similarity	NPD4692	Approved
0.6136	Remote Similarity	NPD4790	Discontinued
0.6136	Remote Similarity	NPD4139	Approved
0.6122	Remote Similarity	NPD7638	Approved
0.61	Remote Similarity	NPD5225	Approved
0.61	Remote Similarity	NPD5226	Approved
0.61	Remote Similarity	NPD4633	Approved
0.61	Remote Similarity	NPD5211	Phase 2
0.61	Remote Similarity	NPD5224	Approved
0.6098	Remote Similarity	NPD7143	Approved
0.6098	Remote Similarity	NPD7144	Approved
0.6092	Remote Similarity	NPD6683	Phase 2
0.6076	Remote Similarity	NPD7341	Phase 2
0.6067	Remote Similarity	NPD6435	Approved
0.6064	Remote Similarity	NPD5785	Approved
0.6061	Remote Similarity	NPD7640	Approved
0.6061	Remote Similarity	NPD7639	Approved
0.6044	Remote Similarity	NPD5363	Approved
0.6044	Remote Similarity	NPD6893	Approved
0.6042	Remote Similarity	NPD5282	Discontinued
0.604	Remote Similarity	NPD4754	Approved
0.604	Remote Similarity	NPD5174	Approved
0.604	Remote Similarity	NPD5175	Approved
0.6024	Remote Similarity	NPD7152	Approved
0.6024	Remote Similarity	NPD7150	Approved
0.6024	Remote Similarity	NPD7151	Approved
0.6024	Remote Similarity	NPD4243	Approved
0.6023	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7514	Phase 3
0.6023	Remote Similarity	NPD7509	Discontinued
0.6022	Remote Similarity	NPD4518	Approved
0.602	Remote Similarity	NPD6084	Phase 2
0.602	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD5281	Approved
0.598	Remote Similarity	NPD5141	Approved
0.5979	Remote Similarity	NPD5695	Phase 3
0.5978	Remote Similarity	NPD4249	Approved
0.5978	Remote Similarity	NPD5330	Approved
0.5978	Remote Similarity	NPD6684	Approved
0.5978	Remote Similarity	NPD7334	Approved
0.5978	Remote Similarity	NPD7146	Approved
0.5978	Remote Similarity	NPD7521	Approved
0.5978	Remote Similarity	NPD6409	Approved
0.5955	Remote Similarity	NPD5369	Approved
0.5955	Remote Similarity	NPD6902	Approved
0.5941	Remote Similarity	NPD7632	Discontinued
0.5934	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5739	Approved
0.5922	Remote Similarity	NPD6675	Approved
0.5922	Remote Similarity	NPD4768	Approved
0.5922	Remote Similarity	NPD7128	Approved
0.5922	Remote Similarity	NPD6402	Approved
0.5922	Remote Similarity	NPD4767	Approved
0.5918	Remote Similarity	NPD5221	Approved
0.5918	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5222	Approved
0.5914	Remote Similarity	NPD4251	Approved
0.5914	Remote Similarity	NPD7750	Discontinued
0.5914	Remote Similarity	NPD7524	Approved
0.5914	Remote Similarity	NPD4250	Approved
0.5897	Remote Similarity	NPD368	Approved
0.5895	Remote Similarity	NPD4096	Approved
0.5889	Remote Similarity	NPD4269	Approved
0.5889	Remote Similarity	NPD4270	Approved
0.5882	Remote Similarity	NPD4785	Approved
0.5882	Remote Similarity	NPD4784	Approved
0.5865	Remote Similarity	NPD5701	Approved
0.5865	Remote Similarity	NPD5697	Approved
0.5859	Remote Similarity	NPD5173	Approved
0.5851	Remote Similarity	NPD6903	Approved
0.5851	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6371	Approved
0.5844	Remote Similarity	NPD3198	Approved
0.5843	Remote Similarity	NPD7332	Phase 2
0.5833	Remote Similarity	NPD7637	Suspended
0.5833	Remote Similarity	NPD4632	Approved
0.5816	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5275	Approved
0.5814	Remote Similarity	NPD4190	Phase 3
0.581	Remote Similarity	NPD6011	Approved
0.581	Remote Similarity	NPD5128	Approved
0.581	Remote Similarity	NPD7320	Approved
0.581	Remote Similarity	NPD6899	Approved
0.581	Remote Similarity	NPD6881	Approved
0.581	Remote Similarity	NPD4730	Approved
0.581	Remote Similarity	NPD4729	Approved
0.5806	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5696	Approved
0.5783	Remote Similarity	NPD3698	Phase 2
0.5778	Remote Similarity	NPD857	Phase 3
0.5778	Remote Similarity	NPD6898	Phase 1
0.5773	Remote Similarity	NPD6399	Phase 3
0.5773	Remote Similarity	NPD5133	Approved
0.5755	Remote Similarity	NPD6014	Approved
0.5755	Remote Similarity	NPD6012	Approved
0.5755	Remote Similarity	NPD6373	Approved
0.5755	Remote Similarity	NPD6013	Approved
0.5755	Remote Similarity	NPD6372	Approved
0.5729	Remote Similarity	NPD7838	Discovery
0.5714	Remote Similarity	NPD4245	Approved
0.5714	Remote Similarity	NPD4244	Approved
0.5701	Remote Similarity	NPD6883	Approved
0.5701	Remote Similarity	NPD5250	Approved
0.5701	Remote Similarity	NPD5247	Approved
0.5701	Remote Similarity	NPD5251	Approved
0.5701	Remote Similarity	NPD5248	Approved
0.5701	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5249	Phase 3
0.5701	Remote Similarity	NPD5135	Approved
0.5701	Remote Similarity	NPD7290	Approved
0.5701	Remote Similarity	NPD7102	Approved
0.5701	Remote Similarity	NPD5169	Approved
0.5699	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD1696	Phase 3
0.5679	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6009	Approved
0.567	Remote Similarity	NPD7087	Discontinued
0.567	Remote Similarity	NPD7515	Phase 2
0.5667	Remote Similarity	NPD4252	Approved
0.5667	Remote Similarity	NPD4695	Discontinued
0.5648	Remote Similarity	NPD6869	Approved
0.5648	Remote Similarity	NPD6617	Approved
0.5648	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6847	Approved
0.5648	Remote Similarity	NPD8130	Phase 1
0.5648	Remote Similarity	NPD5215	Approved
0.5648	Remote Similarity	NPD5217	Approved
0.5648	Remote Similarity	NPD6649	Approved
0.5648	Remote Similarity	NPD5216	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