NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.13
Volume:	240.622
LogP:	2.173
LogD:	1.694
LogS:	-3.612
# Rotatable Bonds:	0
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	4.382
Fsp3:	0.571
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:	-4.79
MDCK Permeability:	2.69624542852398e-05
Pgp-inhibitor:	0.833
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	85.569580078125%
Volume Distribution (VD):	0.491
Pgp-substrate:	12.91775894165039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.729
CYP2C19-inhibitor:	0.282
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.241
CYP2C9-substrate:	0.366
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.307
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.646

ADMET: Excretion

Clearance (CL):	6.497
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.724
Drug-inuced Liver Injury (DILI):	0.146
AMES Toxicity:	0.104
Rat Oral Acute Toxicity:	0.84
Maximum Recommended Daily Dose:	0.844
Skin Sensitization:	0.917
Carcinogencity:	0.926
Eye Corrosion:	0.141
Eye Irritation:	0.572
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC288253

Natural Product ID:	NPC288253
*Common Name:**	(R)-1,5,5-Trimethylspiro[5.5]Undeca-1,7-Diene-3,9-Dione
IUPAC Name:	(6R)-1,5,5-trimethylspiro[5.5]undeca-1,10-diene-3,9-dione
Synonyms:
Standard InCHIKey:	GLVZMJJTCUYPNA-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C14H18O2/c1-10-8-12(16)9-13(2,3)14(10)6-4-11(15)5-7-14/h4,6,8H,5,7,9H2,1-3H3/t14-/m1/s1
SMILES:	CC1=CC(=O)CC(C)(C)[C@]21C=CC(=O)CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492210
PubChem CID:	13918261
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO19629	Laurencia scoparia	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754610]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974618]
NPO19629	Laurencia scoparia	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872159]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27536968]
NPO19629	Laurencia scoparia	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Others	5

Activity Type	# Activity
NON-MOLECULAR	7
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3503	Organism	Nippostrongylus brasiliensis	Nippostrongylus brasiliensis	Activity	<	100.0	uM	PMID[475820]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>=	10000.0	nM	PMID[475821]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	4.0	%	PMID[475821]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	16.0	%	PMID[475821]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	18.0	%	PMID[475821]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	32.0	%	PMID[475821]

☑ 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 NPC288253 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	226
0.1-0.2	2369
0.2-0.3	13545
0.3-0.4	15127
0.4-0.5	7233
0.5-0.6	3240
0.6-0.7	750
0.7-0.8	172
0.8-0.85	23
0.85-0.9	7
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9344	High Similarity	NPC251118
0.9206	High Similarity	NPC87141
0.9206	High Similarity	NPC260474
0.9206	High Similarity	NPC188292
0.9062	High Similarity	NPC256846
0.9	High Similarity	NPC127582
0.8983	High Similarity	NPC311852
0.8871	High Similarity	NPC212210
0.8615	High Similarity	NPC310992
0.8615	High Similarity	NPC155198
0.8571	High Similarity	NPC4638
0.8571	High Similarity	NPC285371
0.8571	High Similarity	NPC475124
0.8548	High Similarity	NPC213152
0.8525	High Similarity	NPC472304
0.8525	High Similarity	NPC276764
0.8507	High Similarity	NPC5701
0.8507	High Similarity	NPC54123
0.8462	Intermediate Similarity	NPC475523
0.8413	Intermediate Similarity	NPC202118
0.8413	Intermediate Similarity	NPC32285
0.8413	Intermediate Similarity	NPC197238
0.8382	Intermediate Similarity	NPC470045
0.8382	Intermediate Similarity	NPC470044
0.8361	Intermediate Similarity	NPC27610
0.8361	Intermediate Similarity	NPC56905
0.8358	Intermediate Similarity	NPC265782
0.8358	Intermediate Similarity	NPC2634
0.8358	Intermediate Similarity	NPC251929
0.8286	Intermediate Similarity	NPC1254
0.8281	Intermediate Similarity	NPC6697
0.8281	Intermediate Similarity	NPC469662
0.8261	Intermediate Similarity	NPC309852
0.8235	Intermediate Similarity	NPC181204
0.8235	Intermediate Similarity	NPC474562
0.8209	Intermediate Similarity	NPC139397
0.8197	Intermediate Similarity	NPC115385
0.8182	Intermediate Similarity	NPC290350
0.8182	Intermediate Similarity	NPC4370
0.8154	Intermediate Similarity	NPC470329
0.8143	Intermediate Similarity	NPC476346
0.8136	Intermediate Similarity	NPC14002
0.8136	Intermediate Similarity	NPC23117
0.8125	Intermediate Similarity	NPC165695
0.8116	Intermediate Similarity	NPC303613
0.8116	Intermediate Similarity	NPC251705
0.8116	Intermediate Similarity	NPC474228
0.8103	Intermediate Similarity	NPC64866
0.8088	Intermediate Similarity	NPC307176
0.8088	Intermediate Similarity	NPC260040
0.8065	Intermediate Similarity	NPC170799
0.8065	Intermediate Similarity	NPC308108
0.8065	Intermediate Similarity	NPC60772
0.8028	Intermediate Similarity	NPC470525
0.8028	Intermediate Similarity	NPC69408
0.8	Intermediate Similarity	NPC474796
0.8	Intermediate Similarity	NPC5626
0.8	Intermediate Similarity	NPC474797
0.8	Intermediate Similarity	NPC329866
0.7971	Intermediate Similarity	NPC190035
0.7971	Intermediate Similarity	NPC234707
0.7971	Intermediate Similarity	NPC115023
0.7971	Intermediate Similarity	NPC305501
0.7971	Intermediate Similarity	NPC21944
0.7971	Intermediate Similarity	NPC225467
0.7969	Intermediate Similarity	NPC60565
0.7937	Intermediate Similarity	NPC96551
0.7937	Intermediate Similarity	NPC285594
0.7937	Intermediate Similarity	NPC259261
0.7931	Intermediate Similarity	NPC116906
0.7931	Intermediate Similarity	NPC228776
0.7903	Intermediate Similarity	NPC192427
0.7887	Intermediate Similarity	NPC293803
0.7887	Intermediate Similarity	NPC473171
0.7869	Intermediate Similarity	NPC200258
0.7857	Intermediate Similarity	NPC130016
0.7857	Intermediate Similarity	NPC180015
0.7857	Intermediate Similarity	NPC109576
0.7857	Intermediate Similarity	NPC56747
0.7833	Intermediate Similarity	NPC37644
0.7833	Intermediate Similarity	NPC268564
0.7833	Intermediate Similarity	NPC295777
0.7833	Intermediate Similarity	NPC296311
0.7833	Intermediate Similarity	NPC69898
0.7826	Intermediate Similarity	NPC282593
0.7826	Intermediate Similarity	NPC35734
0.7826	Intermediate Similarity	NPC159577
0.7812	Intermediate Similarity	NPC25853
0.7808	Intermediate Similarity	NPC74410
0.7808	Intermediate Similarity	NPC189485
0.7778	Intermediate Similarity	NPC266295
0.7778	Intermediate Similarity	NPC469793
0.7778	Intermediate Similarity	NPC94991
0.7778	Intermediate Similarity	NPC469796
0.7778	Intermediate Similarity	NPC30215
0.7761	Intermediate Similarity	NPC323005
0.7746	Intermediate Similarity	NPC20025
0.7746	Intermediate Similarity	NPC219232
0.7746	Intermediate Similarity	NPC128346
0.7746	Intermediate Similarity	NPC255021
0.7733	Intermediate Similarity	NPC475833
0.7714	Intermediate Similarity	NPC133253
0.7703	Intermediate Similarity	NPC90965
0.7703	Intermediate Similarity	NPC27817
0.7703	Intermediate Similarity	NPC170793
0.7703	Intermediate Similarity	NPC19900
0.7692	Intermediate Similarity	NPC97322
0.7692	Intermediate Similarity	NPC475795
0.7681	Intermediate Similarity	NPC182815
0.7681	Intermediate Similarity	NPC136473
0.7681	Intermediate Similarity	NPC286814
0.7671	Intermediate Similarity	NPC97377
0.7639	Intermediate Similarity	NPC255650
0.7639	Intermediate Similarity	NPC65650
0.7627	Intermediate Similarity	NPC118788
0.7627	Intermediate Similarity	NPC32351
0.7619	Intermediate Similarity	NPC193695
0.76	Intermediate Similarity	NPC476809
0.76	Intermediate Similarity	NPC474509
0.76	Intermediate Similarity	NPC108955
0.7581	Intermediate Similarity	NPC275472
0.7576	Intermediate Similarity	NPC167256
0.7571	Intermediate Similarity	NPC151045
0.7571	Intermediate Similarity	NPC246722
0.7568	Intermediate Similarity	NPC275494
0.7568	Intermediate Similarity	NPC115515
0.7568	Intermediate Similarity	NPC471409
0.7568	Intermediate Similarity	NPC62336
0.7541	Intermediate Similarity	NPC474141
0.7536	Intermediate Similarity	NPC39157
0.7536	Intermediate Similarity	NPC20610
0.7536	Intermediate Similarity	NPC296697
0.7536	Intermediate Similarity	NPC82477
0.7536	Intermediate Similarity	NPC142754
0.7534	Intermediate Similarity	NPC263582
0.7534	Intermediate Similarity	NPC180886
0.7534	Intermediate Similarity	NPC110725
0.75	Intermediate Similarity	NPC236623
0.75	Intermediate Similarity	NPC225515
0.75	Intermediate Similarity	NPC474085
0.75	Intermediate Similarity	NPC211641
0.75	Intermediate Similarity	NPC55869
0.75	Intermediate Similarity	NPC176171
0.75	Intermediate Similarity	NPC92327
0.75	Intermediate Similarity	NPC116797
0.75	Intermediate Similarity	NPC99308
0.7467	Intermediate Similarity	NPC476177
0.7465	Intermediate Similarity	NPC304983
0.7465	Intermediate Similarity	NPC470078
0.7465	Intermediate Similarity	NPC223187
0.7463	Intermediate Similarity	NPC473902
0.7463	Intermediate Similarity	NPC169275
0.7463	Intermediate Similarity	NPC150162
0.7463	Intermediate Similarity	NPC52449
0.746	Intermediate Similarity	NPC473733
0.7432	Intermediate Similarity	NPC266193
0.7432	Intermediate Similarity	NPC472300
0.7432	Intermediate Similarity	NPC257666
0.7432	Intermediate Similarity	NPC165711
0.7429	Intermediate Similarity	NPC474060
0.7419	Intermediate Similarity	NPC63396
0.7419	Intermediate Similarity	NPC250539
0.7419	Intermediate Similarity	NPC202850
0.7403	Intermediate Similarity	NPC103486
0.7403	Intermediate Similarity	NPC302661
0.7403	Intermediate Similarity	NPC3511
0.7403	Intermediate Similarity	NPC38796
0.7403	Intermediate Similarity	NPC158411
0.7403	Intermediate Similarity	NPC142253
0.7403	Intermediate Similarity	NPC238991
0.7397	Intermediate Similarity	NPC114236
0.7391	Intermediate Similarity	NPC176107
0.7391	Intermediate Similarity	NPC20181
0.7391	Intermediate Similarity	NPC220210
0.7391	Intermediate Similarity	NPC193770
0.7368	Intermediate Similarity	NPC26139
0.7361	Intermediate Similarity	NPC276336
0.7361	Intermediate Similarity	NPC247586
0.7361	Intermediate Similarity	NPC474488
0.7361	Intermediate Similarity	NPC153660
0.7353	Intermediate Similarity	NPC268039
0.7344	Intermediate Similarity	NPC55004
0.7344	Intermediate Similarity	NPC230823
0.7344	Intermediate Similarity	NPC267626
0.7344	Intermediate Similarity	NPC49575
0.7342	Intermediate Similarity	NPC474537
0.7333	Intermediate Similarity	NPC469996
0.7333	Intermediate Similarity	NPC163984
0.7333	Intermediate Similarity	NPC176819
0.7333	Intermediate Similarity	NPC58970
0.7333	Intermediate Similarity	NPC478246
0.7333	Intermediate Similarity	NPC478247
0.7333	Intermediate Similarity	NPC475994
0.7324	Intermediate Similarity	NPC40574
0.7313	Intermediate Similarity	NPC472306
0.7308	Intermediate Similarity	NPC49019
0.7308	Intermediate Similarity	NPC118423
0.7297	Intermediate Similarity	NPC186554
0.7297	Intermediate Similarity	NPC40353
0.7297	Intermediate Similarity	NPC26504

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 NPC288253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	2597
0.2-0.3	4309
0.3-0.4	1446
0.4-0.5	385
0.5-0.6	169
0.6-0.7	25
0.7-0.8	9
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8358	Intermediate Similarity	NPD4691	Approved
0.8261	Intermediate Similarity	NPD4058	Approved
0.8261	Intermediate Similarity	NPD4687	Approved
0.8235	Intermediate Similarity	NPD5276	Approved
0.8209	Intermediate Similarity	NPD4137	Phase 3
0.8088	Intermediate Similarity	NPD4747	Approved
0.8065	Intermediate Similarity	NPD287	Approved
0.8	Intermediate Similarity	NPD5733	Approved
0.7536	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4695	Discontinued
0.7273	Intermediate Similarity	NPD8028	Phase 2
0.725	Intermediate Similarity	NPD5690	Phase 2
0.7	Intermediate Similarity	NPD7331	Phase 2
0.6962	Remote Similarity	NPD4223	Phase 3
0.6962	Remote Similarity	NPD4221	Approved
0.6951	Remote Similarity	NPD3573	Approved
0.6923	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4519	Discontinued
0.6829	Remote Similarity	NPD4623	Approved
0.6829	Remote Similarity	NPD5279	Phase 3
0.6829	Remote Similarity	NPD5280	Approved
0.6829	Remote Similarity	NPD4694	Approved
0.679	Remote Similarity	NPD3133	Approved
0.679	Remote Similarity	NPD4197	Approved
0.679	Remote Similarity	NPD3665	Phase 1
0.679	Remote Similarity	NPD3666	Approved
0.6707	Remote Similarity	NPD5329	Approved
0.6706	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD4194	Approved
0.6667	Remote Similarity	NPD4192	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD4191	Approved
0.6667	Remote Similarity	NPD4193	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6628	Remote Similarity	NPD5281	Approved
0.6628	Remote Similarity	NPD5284	Approved
0.6628	Remote Similarity	NPD5694	Approved
0.6628	Remote Similarity	NPD6079	Approved
0.6627	Remote Similarity	NPD7521	Approved
0.6627	Remote Similarity	NPD4689	Approved
0.6627	Remote Similarity	NPD3618	Phase 1
0.6627	Remote Similarity	NPD5205	Approved
0.6627	Remote Similarity	NPD7334	Approved
0.6627	Remote Similarity	NPD6409	Approved
0.6627	Remote Similarity	NPD6684	Approved
0.6627	Remote Similarity	NPD4693	Phase 3
0.6627	Remote Similarity	NPD4690	Approved
0.6627	Remote Similarity	NPD7146	Approved
0.6627	Remote Similarity	NPD4688	Approved
0.6627	Remote Similarity	NPD4138	Approved
0.6627	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5330	Approved
0.6582	Remote Similarity	NPD4195	Approved
0.6543	Remote Similarity	NPD3667	Approved
0.6543	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5692	Phase 3
0.6512	Remote Similarity	NPD4096	Approved
0.6506	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD5208	Approved
0.6471	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6672	Approved
0.6471	Remote Similarity	NPD5737	Approved
0.6471	Remote Similarity	NPD6903	Approved
0.6437	Remote Similarity	NPD6050	Approved
0.6404	Remote Similarity	NPD4629	Approved
0.6404	Remote Similarity	NPD5210	Approved
0.6395	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5328	Approved
0.6395	Remote Similarity	NPD6904	Approved
0.6395	Remote Similarity	NPD4753	Phase 2
0.6395	Remote Similarity	NPD6673	Approved
0.6395	Remote Similarity	NPD6080	Approved
0.6389	Remote Similarity	NPD7341	Phase 2
0.6386	Remote Similarity	NPD4786	Approved
0.6386	Remote Similarity	NPD3668	Phase 3
0.6349	Remote Similarity	NPD8262	Approved
0.6338	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5221	Approved
0.6333	Remote Similarity	NPD5222	Approved
0.6333	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD8039	Approved
0.6269	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD3495	Discontinued
0.6264	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD7609	Phase 3
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD7515	Phase 2
0.6235	Remote Similarity	NPD6098	Approved
0.6222	Remote Similarity	NPD5695	Phase 3
0.622	Remote Similarity	NPD4139	Approved
0.622	Remote Similarity	NPD4692	Approved
0.618	Remote Similarity	NPD4202	Approved
0.618	Remote Similarity	NPD7631	Approved
0.618	Remote Similarity	NPD5133	Approved
0.6163	Remote Similarity	NPD650	Approved
0.6154	Remote Similarity	NPD7614	Phase 1
0.6154	Remote Similarity	NPD7732	Phase 3
0.6129	Remote Similarity	NPD4696	Approved
0.6129	Remote Similarity	NPD5285	Approved
0.6129	Remote Similarity	NPD5286	Approved
0.6118	Remote Similarity	NPD1696	Phase 3
0.6111	Remote Similarity	NPD7900	Approved
0.6111	Remote Similarity	NPD6001	Approved
0.6111	Remote Similarity	NPD7748	Approved
0.6111	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5223	Approved
0.6044	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5654	Approved
0.6027	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD5091	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD5224	Approved
0.5978	Remote Similarity	NPD4697	Phase 3
0.5942	Remote Similarity	NPD4219	Approved
0.5938	Remote Similarity	NPD5174	Approved
0.5938	Remote Similarity	NPD5175	Approved
0.5914	Remote Similarity	NPD4755	Approved
0.5914	Remote Similarity	NPD6084	Phase 2
0.5914	Remote Similarity	NPD5959	Approved
0.5914	Remote Similarity	NPD6083	Phase 2
0.5914	Remote Similarity	NPD7902	Approved
0.5902	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6411	Approved
0.5882	Remote Similarity	NPD4788	Approved
0.5876	Remote Similarity	NPD5141	Approved
0.5875	Remote Similarity	NPD8264	Approved
0.5854	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5696	Approved
0.5824	Remote Similarity	NPD6399	Phase 3
0.5789	Remote Similarity	NPD4700	Approved
0.5789	Remote Similarity	NPD6404	Discontinued
0.5765	Remote Similarity	NPD5209	Approved
0.5758	Remote Similarity	NPD5697	Approved
0.5758	Remote Similarity	NPD6614	Approved
0.5714	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5168	Approved
0.57	Remote Similarity	NPD4729	Approved
0.57	Remote Similarity	NPD6881	Approved
0.57	Remote Similarity	NPD6011	Approved
0.57	Remote Similarity	NPD6899	Approved
0.57	Remote Similarity	NPD4730	Approved
0.5672	Remote Similarity	NPD29	Approved
0.5672	Remote Similarity	NPD28	Approved
0.5667	Remote Similarity	NPD6101	Approved
0.5667	Remote Similarity	NPD5783	Phase 3
0.5667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD942	Approved
0.5644	Remote Similarity	NPD6014	Approved
0.5644	Remote Similarity	NPD6012	Approved
0.5644	Remote Similarity	NPD6013	Approved
0.5612	Remote Similarity	NPD6052	Approved
0.5612	Remote Similarity	NPD4754	Approved
0.5604	Remote Similarity	NPD5785	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