NPASS Compound

Structure

NPC308844 OpenBabel07101719242D 22 22 0 0 1 0 0 0 0 0999 V2000 -1.3090 4.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5135 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0577 -0.4666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6509 0.4469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3406 -0.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1180 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5316 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8090 2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1180 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2541 0.2257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 3.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0632 -0.3621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9586 -1.3566 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 17 2 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 15 2 0 0 0 0 9 17 1 0 0 0 0 10 16 2 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 17 19 1 0 0 0 0 18 16 1 1 0 0 0 19 21 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	352.954
LogP:	2.94
LogD:	3.063
LogS:	-3.97
# Rotatable Bonds:	3
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	4.603
Fsp3:	0.6
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:	-4.486
MDCK Permeability:	2.6644946046872064e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.607
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.792
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.821
Plasma Protein Binding (PPB):	85.14015197753906%
Volume Distribution (VD):	0.952
Pgp-substrate:	14.71414566040039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.096
CYP1A2-substrate:	0.24
CYP2C19-inhibitor:	0.203
CYP2C19-substrate:	0.452
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.368
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.148
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	4.683
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.579
Carcinogencity:	0.346
Eye Corrosion:	0.041
Eye Irritation:	0.721
Respiratory Toxicity:	0.595

Download Data

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

Natural Product: NPC308844

Natural Product ID:	NPC308844
*Common Name:**	Rel-Eunicidiol
IUPAC Name:	(1R,5E,9S)-9-[(2E,4E)-6-hydroxy-6-methylhepta-2,4-dien-2-yl]-6-methyl-2-methylidenecyclodec-5-en-1-ol
Synonyms:	Rel-Eunicidiol
Standard InCHIKey:	BONUHTOMAPQCIR-NGOVDTHNSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-15-8-6-9-17(3)19(21)14-18(12-11-15)16(2)10-7-13-20(4,5)22/h7-8,10,13,18-19,21-22H,3,6,9,11-12,14H2,1-2,4-5H3/b13-7+,15-8+,16-10+/t18-,19+/m0/s1
SMILES:	C/C/1=CCCC(=C)[C@@H](C[C@H](CC1)/C(=C/C=C/C(O)(C)C)/C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071304
PubChem CID:	60200859
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO27691	Eunicea fusca	Species	Plexauridae	Eukaryota	n.a.	Caribbean	n.a.	PMID[21865038]
NPO27691	Eunicea fusca	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22734800]
NPO27691	Eunicea fusca	Species	Plexauridae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	0.1	%	PMID[489614]

☑ 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 NPC308844 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	156
0.1-0.2	1400
0.2-0.3	8854
0.3-0.4	17596
0.4-0.5	9171
0.5-0.6	4296
0.6-0.7	1033
0.7-0.8	160
0.8-0.85	26
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC300593
0.8871	High Similarity	NPC225342
0.8852	High Similarity	NPC122239
0.8548	High Similarity	NPC475931
0.8507	High Similarity	NPC239373
0.8507	High Similarity	NPC329989
0.8438	Intermediate Similarity	NPC473508
0.8413	Intermediate Similarity	NPC99487
0.8387	Intermediate Similarity	NPC226848
0.8387	Intermediate Similarity	NPC155025
0.8387	Intermediate Similarity	NPC181872
0.8209	Intermediate Similarity	NPC73603
0.8209	Intermediate Similarity	NPC259299
0.8197	Intermediate Similarity	NPC329686
0.8143	Intermediate Similarity	NPC130665
0.8125	Intermediate Similarity	NPC240506
0.8088	Intermediate Similarity	NPC305698
0.8088	Intermediate Similarity	NPC224532
0.806	Intermediate Similarity	NPC311736
0.806	Intermediate Similarity	NPC267027
0.8	Intermediate Similarity	NPC208638
0.7941	Intermediate Similarity	NPC163290
0.7903	Intermediate Similarity	NPC227135
0.7869	Intermediate Similarity	NPC474496
0.7846	Intermediate Similarity	NPC66020
0.7833	Intermediate Similarity	NPC473672
0.7833	Intermediate Similarity	NPC474495
0.7808	Intermediate Similarity	NPC256720
0.7808	Intermediate Similarity	NPC236228
0.7761	Intermediate Similarity	NPC309300
0.7761	Intermediate Similarity	NPC110241
0.7746	Intermediate Similarity	NPC472254
0.7727	Intermediate Similarity	NPC321867
0.7727	Intermediate Similarity	NPC68679
0.7727	Intermediate Similarity	NPC207007
0.7727	Intermediate Similarity	NPC475251
0.7714	Intermediate Similarity	NPC74722
0.7714	Intermediate Similarity	NPC90115
0.7714	Intermediate Similarity	NPC217570
0.7714	Intermediate Similarity	NPC471560
0.7714	Intermediate Similarity	NPC304690
0.7705	Intermediate Similarity	NPC68014
0.7681	Intermediate Similarity	NPC114651
0.7681	Intermediate Similarity	NPC278895
0.7671	Intermediate Similarity	NPC313179
0.7671	Intermediate Similarity	NPC171148
0.7671	Intermediate Similarity	NPC69383
0.7667	Intermediate Similarity	NPC26960
0.7667	Intermediate Similarity	NPC182102
0.7667	Intermediate Similarity	NPC474460
0.7656	Intermediate Similarity	NPC52012
0.7647	Intermediate Similarity	NPC19569
0.7639	Intermediate Similarity	NPC329763
0.7619	Intermediate Similarity	NPC281590
0.7612	Intermediate Similarity	NPC474155
0.7612	Intermediate Similarity	NPC473759
0.7606	Intermediate Similarity	NPC4299
0.7606	Intermediate Similarity	NPC34834
0.7576	Intermediate Similarity	NPC471081
0.7576	Intermediate Similarity	NPC127824
0.7571	Intermediate Similarity	NPC272961
0.7568	Intermediate Similarity	NPC471658
0.7568	Intermediate Similarity	NPC310643
0.7536	Intermediate Similarity	NPC326310
0.7534	Intermediate Similarity	NPC190859
0.75	Intermediate Similarity	NPC471537
0.75	Intermediate Similarity	NPC474643
0.75	Intermediate Similarity	NPC473865
0.75	Intermediate Similarity	NPC24443
0.75	Intermediate Similarity	NPC471662
0.7465	Intermediate Similarity	NPC101622
0.7463	Intermediate Similarity	NPC210346
0.746	Intermediate Similarity	NPC49059
0.746	Intermediate Similarity	NPC110732
0.746	Intermediate Similarity	NPC256209
0.7432	Intermediate Similarity	NPC23231
0.7432	Intermediate Similarity	NPC60818
0.7429	Intermediate Similarity	NPC68703
0.7429	Intermediate Similarity	NPC472253
0.7429	Intermediate Similarity	NPC472255
0.7429	Intermediate Similarity	NPC136813
0.7429	Intermediate Similarity	NPC477791
0.7429	Intermediate Similarity	NPC82337
0.7429	Intermediate Similarity	NPC69649
0.7397	Intermediate Similarity	NPC68443
0.7397	Intermediate Similarity	NPC275098
0.7391	Intermediate Similarity	NPC61503
0.7377	Intermediate Similarity	NPC329773
0.7377	Intermediate Similarity	NPC131623
0.7368	Intermediate Similarity	NPC4436
0.7368	Intermediate Similarity	NPC475980
0.7353	Intermediate Similarity	NPC279200
0.7344	Intermediate Similarity	NPC251666
0.7344	Intermediate Similarity	NPC232247
0.7344	Intermediate Similarity	NPC148163
0.7344	Intermediate Similarity	NPC223604
0.7344	Intermediate Similarity	NPC477725
0.7344	Intermediate Similarity	NPC130209
0.7344	Intermediate Similarity	NPC477726
0.7344	Intermediate Similarity	NPC474644
0.7344	Intermediate Similarity	NPC148216
0.7333	Intermediate Similarity	NPC265588
0.7333	Intermediate Similarity	NPC170148
0.7324	Intermediate Similarity	NPC471238
0.7324	Intermediate Similarity	NPC167527
0.7302	Intermediate Similarity	NPC34577
0.7297	Intermediate Similarity	NPC201048
0.7297	Intermediate Similarity	NPC27395
0.7297	Intermediate Similarity	NPC471525
0.7297	Intermediate Similarity	NPC476366
0.7297	Intermediate Similarity	NPC471659
0.7297	Intermediate Similarity	NPC306727
0.7297	Intermediate Similarity	NPC329090
0.7286	Intermediate Similarity	NPC272125
0.7286	Intermediate Similarity	NPC476406
0.7286	Intermediate Similarity	NPC202017
0.7286	Intermediate Similarity	NPC149680
0.726	Intermediate Similarity	NPC95863
0.726	Intermediate Similarity	NPC471272
0.726	Intermediate Similarity	NPC23954
0.7258	Intermediate Similarity	NPC59408
0.7258	Intermediate Similarity	NPC71053
0.725	Intermediate Similarity	NPC238485
0.725	Intermediate Similarity	NPC231310
0.7246	Intermediate Similarity	NPC225415
0.7246	Intermediate Similarity	NPC96793
0.7246	Intermediate Similarity	NPC323424
0.7246	Intermediate Similarity	NPC290367
0.7237	Intermediate Similarity	NPC476007
0.7237	Intermediate Similarity	NPC477426
0.7237	Intermediate Similarity	NPC477425
0.7237	Intermediate Similarity	NPC477427
0.7237	Intermediate Similarity	NPC40049
0.7237	Intermediate Similarity	NPC474826
0.7237	Intermediate Similarity	NPC476703
0.7237	Intermediate Similarity	NPC84360
0.7237	Intermediate Similarity	NPC91594
0.7237	Intermediate Similarity	NPC476439
0.7237	Intermediate Similarity	NPC470758
0.7237	Intermediate Similarity	NPC470711
0.7231	Intermediate Similarity	NPC470969
0.7231	Intermediate Similarity	NPC249645
0.7231	Intermediate Similarity	NPC470966
0.7231	Intermediate Similarity	NPC473847
0.7231	Intermediate Similarity	NPC475384
0.7231	Intermediate Similarity	NPC161838
0.7231	Intermediate Similarity	NPC477661
0.7231	Intermediate Similarity	NPC48891
0.7231	Intermediate Similarity	NPC471960
0.7231	Intermediate Similarity	NPC55412
0.7231	Intermediate Similarity	NPC470968
0.7231	Intermediate Similarity	NPC470967
0.7222	Intermediate Similarity	NPC9942
0.7222	Intermediate Similarity	NPC473893
0.7215	Intermediate Similarity	NPC477390
0.7215	Intermediate Similarity	NPC477385
0.7206	Intermediate Similarity	NPC274704
0.72	Intermediate Similarity	NPC319090
0.72	Intermediate Similarity	NPC32832
0.72	Intermediate Similarity	NPC328104
0.7183	Intermediate Similarity	NPC45782
0.7179	Intermediate Similarity	NPC324772
0.7164	Intermediate Similarity	NPC278202
0.7162	Intermediate Similarity	NPC220939
0.7162	Intermediate Similarity	NPC477085
0.7162	Intermediate Similarity	NPC265485
0.7143	Intermediate Similarity	NPC238352
0.7143	Intermediate Similarity	NPC477009
0.7143	Intermediate Similarity	NPC294358
0.7143	Intermediate Similarity	NPC83351
0.7143	Intermediate Similarity	NPC255863
0.7143	Intermediate Similarity	NPC167891
0.7143	Intermediate Similarity	NPC35756
0.7143	Intermediate Similarity	NPC471200
0.7143	Intermediate Similarity	NPC40417
0.7143	Intermediate Similarity	NPC136164
0.7143	Intermediate Similarity	NPC245947
0.7125	Intermediate Similarity	NPC470384
0.7123	Intermediate Similarity	NPC473361
0.7123	Intermediate Similarity	NPC49422
0.7123	Intermediate Similarity	NPC329904
0.7123	Intermediate Similarity	NPC9161
0.7123	Intermediate Similarity	NPC129630
0.7123	Intermediate Similarity	NPC470041
0.7121	Intermediate Similarity	NPC470970
0.7105	Intermediate Similarity	NPC470749
0.7105	Intermediate Similarity	NPC279537
0.7105	Intermediate Similarity	NPC271070
0.7105	Intermediate Similarity	NPC253190
0.7105	Intermediate Similarity	NPC315261
0.7105	Intermediate Similarity	NPC268111
0.7101	Intermediate Similarity	NPC474480
0.7101	Intermediate Similarity	NPC174956
0.7089	Intermediate Similarity	NPC315731
0.7089	Intermediate Similarity	NPC249423
0.7089	Intermediate Similarity	NPC320525
0.7089	Intermediate Similarity	NPC264245
0.7089	Intermediate Similarity	NPC112868
0.7089	Intermediate Similarity	NPC474894
0.7083	Intermediate Similarity	NPC96484

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 NPC308844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1972
0.2-0.3	4083
0.3-0.4	2144
0.4-0.5	632
0.5-0.6	103
0.6-0.7	55
0.7-0.8	4
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7727	Intermediate Similarity	NPD368	Approved
0.7671	Intermediate Similarity	NPD8264	Approved
0.76	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7514	Phase 3
0.7403	Intermediate Similarity	NPD7332	Phase 2
0.7344	Intermediate Similarity	NPD342	Phase 1
0.7297	Intermediate Similarity	NPD6926	Approved
0.7297	Intermediate Similarity	NPD6924	Approved
0.7231	Intermediate Similarity	NPD4219	Approved
0.7179	Intermediate Similarity	NPD6930	Phase 2
0.7179	Intermediate Similarity	NPD6931	Approved
0.7162	Intermediate Similarity	NPD4732	Discontinued
0.7143	Intermediate Similarity	NPD7145	Approved
0.7123	Intermediate Similarity	NPD7144	Approved
0.7123	Intermediate Similarity	NPD7143	Approved
0.7105	Intermediate Similarity	NPD6933	Approved
0.7089	Intermediate Similarity	NPD6902	Approved
0.7059	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6929	Approved
0.7027	Intermediate Similarity	NPD7151	Approved
0.7027	Intermediate Similarity	NPD7152	Approved
0.7027	Intermediate Similarity	NPD7150	Approved
0.7013	Intermediate Similarity	NPD5776	Phase 2
0.7013	Intermediate Similarity	NPD6932	Approved
0.7013	Intermediate Similarity	NPD6925	Approved
0.7	Intermediate Similarity	NPD4265	Approved
0.6986	Remote Similarity	NPD6922	Approved
0.6986	Remote Similarity	NPD6923	Approved
0.6962	Remote Similarity	NPD4819	Approved
0.6962	Remote Similarity	NPD4820	Approved
0.6962	Remote Similarity	NPD4822	Approved
0.6962	Remote Similarity	NPD4821	Approved
0.6914	Remote Similarity	NPD6695	Phase 3
0.6875	Remote Similarity	NPD6898	Phase 1
0.6829	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7509	Discontinued
0.6747	Remote Similarity	NPD6893	Approved
0.6709	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4268	Approved
0.6709	Remote Similarity	NPD4271	Approved
0.6707	Remote Similarity	NPD7154	Phase 3
0.6707	Remote Similarity	NPD5331	Approved
0.6707	Remote Similarity	NPD5362	Discontinued
0.6707	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6625	Remote Similarity	NPD6683	Phase 2
0.6588	Remote Similarity	NPD7524	Approved
0.6588	Remote Similarity	NPD7750	Discontinued
0.6585	Remote Similarity	NPD4269	Approved
0.6585	Remote Similarity	NPD4270	Approved
0.6543	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7983	Approved
0.6438	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5778	Approved
0.6404	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD7838	Discovery
0.6353	Remote Similarity	NPD5363	Approved
0.6351	Remote Similarity	NPD7331	Phase 2
0.6341	Remote Similarity	NPD4252	Approved
0.6341	Remote Similarity	NPD7525	Registered
0.6329	Remote Similarity	NPD6942	Approved
0.6329	Remote Similarity	NPD7339	Approved
0.6292	Remote Similarity	NPD7637	Suspended
0.6292	Remote Similarity	NPD7087	Discontinued
0.6279	Remote Similarity	NPD5786	Approved
0.6267	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD4194	Approved
0.625	Remote Similarity	NPD4193	Approved
0.625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4191	Approved
0.625	Remote Similarity	NPD4192	Approved
0.6237	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7645	Phase 2
0.6207	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7839	Suspended
0.618	Remote Similarity	NPD7136	Phase 2
0.6164	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5368	Approved
0.6145	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD8039	Approved
0.6081	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD3197	Phase 1
0.6067	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6101	Approved
0.6023	Remote Similarity	NPD4251	Approved
0.6023	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD7341	Phase 2
0.6	Remote Similarity	NPD4784	Approved
0.6	Remote Similarity	NPD6435	Approved
0.6	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD4785	Approved
0.5977	Remote Similarity	NPD1696	Phase 3
0.5949	Remote Similarity	NPD4243	Approved
0.5934	Remote Similarity	NPD6411	Approved
0.5909	Remote Similarity	NPD5279	Phase 3
0.5909	Remote Similarity	NPD4249	Approved
0.5889	Remote Similarity	NPD5370	Suspended
0.5862	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4786	Approved
0.5833	Remote Similarity	NPD6648	Approved
0.5824	Remote Similarity	NPD46	Approved
0.5824	Remote Similarity	NPD6698	Approved
0.5814	Remote Similarity	NPD3667	Approved
0.5773	Remote Similarity	NPD5344	Discontinued
0.5761	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6110	Phase 1
0.573	Remote Similarity	NPD4519	Discontinued
0.573	Remote Similarity	NPD4623	Approved
0.5714	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD3195	Phase 2
0.5714	Remote Similarity	NPD4266	Approved
0.5714	Remote Similarity	NPD3194	Approved
0.5682	Remote Similarity	NPD3133	Approved
0.5682	Remote Similarity	NPD3666	Approved
0.5682	Remote Similarity	NPD3665	Phase 1
0.5672	Remote Similarity	NPD4220	Pre-registration
0.5657	Remote Similarity	NPD6647	Phase 2
0.5647	Remote Similarity	NPD4195	Approved
0.5632	Remote Similarity	NPD5209	Approved
0.5625	Remote Similarity	NPD3212	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