NPASS Compound

Structure

CID271282 OpenBabel06191716072D 24 23 0 0 1 0 0 0 0 0999 V2000 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 -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 -2.5981 1.5000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 -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 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 13 1 0 0 0 0 10 15 2 0 0 0 0 11 12 1 0 0 0 0 11 14 3 0 0 0 0 12 16 3 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 20 1 0 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 22 1 6 0 0 0 20 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	371.182
LogP:	3.499
LogD:	3.167
LogS:	-4.091
# Rotatable Bonds:	12
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.264
Synthetic Accessibility Score:	4.003
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.791
MDCK Permeability:	3.6961613659514114e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.825
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	100.3278579711914%
Volume Distribution (VD):	1.352
Pgp-substrate:	2.329489231109619%

ADMET: Metabolism

CYP1A2-inhibitor:	0.509
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.878
CYP2C19-substrate:	0.294
CYP2C9-inhibitor:	0.864
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.869
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	4.109
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.938
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.96
Carcinogencity:	0.087
Eye Corrosion:	0.934
Eye Irritation:	0.971
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC271282

Natural Product ID:	NPC271282
*Common Name:**	(9Z,11S,16R)-Dihydroxyoctadeca-9,17-Dien-12,14-Diyn-1-Yl Acetate
IUPAC Name:	[(9Z,11S,16R)-11,16-dihydroxyoctadeca-9,17-dien-12,14-diynyl] acetate
Synonyms:
Standard InCHIKey:	VVURZXYIXNNJCG-KOIKSQSCSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-3-19(22)14-11-12-16-20(23)15-10-8-6-4-5-7-9-13-17-24-18(2)21/h3,10,15,19-20,22-23H,1,4-9,13,17H2,2H3/b15-10-/t19-,20+/m1/s1
SMILES:	CC(=O)OCCCCCCCC/C=C[C@@H](C#CC#C[C@@H](C=C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490698
PubChem CID:	11652871
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain 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
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	exudates	n.a.	n.a.	PMID[16441065]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[18558745]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21824777]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[25891102]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21056	Angelica keiskei	Species	Apiaceae	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	2
Others	7

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	IC50	=	118100.0	nM	PMID[553732]
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Inhibition	=	49.0	%	PMID[553732]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[553733]
NPT2	Others	Unspecified		Activity	=	18.7	%	PMID[553733]
NPT2	Others	Unspecified		Activity	=	53.1	%	PMID[553733]
NPT2	Others	Unspecified		Activity	=	81.4	%	PMID[553733]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[553733]
NPT2	Others	Unspecified		IC50	=	511.0	molar ratio	PMID[553733]
NPT2	Others	Unspecified		Ratio	=	1.2	n.a.	PMID[553733]

☑ 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 NPC271282 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	152
0.1-0.2	2406
0.2-0.3	12673
0.3-0.4	15747
0.4-0.5	7631
0.5-0.6	3116
0.6-0.7	703
0.7-0.8	220
0.8-0.85	36
0.85-0.9	6
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC325929
1.0	High Similarity	NPC66460
0.9828	High Similarity	NPC29697
0.9	High Similarity	NPC475984
0.8983	High Similarity	NPC474267
0.8852	High Similarity	NPC470965
0.8644	High Similarity	NPC44542
0.8644	High Similarity	NPC212730
0.8644	High Similarity	NPC265551
0.8525	High Similarity	NPC471278
0.85	High Similarity	NPC469373
0.8448	Intermediate Similarity	NPC49059
0.8448	Intermediate Similarity	NPC256209
0.8413	Intermediate Similarity	NPC226592
0.8413	Intermediate Similarity	NPC470320
0.8333	Intermediate Similarity	NPC594
0.8333	Intermediate Similarity	NPC48968
0.8333	Intermediate Similarity	NPC472445
0.8305	Intermediate Similarity	NPC474513
0.8305	Intermediate Similarity	NPC470963
0.8305	Intermediate Similarity	NPC146551
0.8226	Intermediate Similarity	NPC299730
0.8167	Intermediate Similarity	NPC470964
0.8167	Intermediate Similarity	NPC311648
0.8065	Intermediate Similarity	NPC222852
0.806	Intermediate Similarity	NPC470436
0.8033	Intermediate Similarity	NPC193975
0.8033	Intermediate Similarity	NPC470970
0.8033	Intermediate Similarity	NPC471279
0.8033	Intermediate Similarity	NPC471277
0.8	Intermediate Similarity	NPC477726
0.8	Intermediate Similarity	NPC152668
0.8	Intermediate Similarity	NPC477725
0.7931	Intermediate Similarity	NPC151782
0.7931	Intermediate Similarity	NPC129263
0.7895	Intermediate Similarity	NPC207815
0.7895	Intermediate Similarity	NPC85079
0.7895	Intermediate Similarity	NPC31194
0.7895	Intermediate Similarity	NPC248884
0.7869	Intermediate Similarity	NPC473847
0.7869	Intermediate Similarity	NPC471960
0.7869	Intermediate Similarity	NPC470967
0.7869	Intermediate Similarity	NPC470966
0.7869	Intermediate Similarity	NPC470969
0.7869	Intermediate Similarity	NPC470968
0.7869	Intermediate Similarity	NPC475384
0.7869	Intermediate Similarity	NPC161838
0.7869	Intermediate Similarity	NPC477661
0.7833	Intermediate Similarity	NPC110732
0.7812	Intermediate Similarity	NPC477829
0.7812	Intermediate Similarity	NPC113293
0.7812	Intermediate Similarity	NPC26810
0.7797	Intermediate Similarity	NPC142092
0.7761	Intermediate Similarity	NPC473752
0.7761	Intermediate Similarity	NPC99619
0.7761	Intermediate Similarity	NPC26500
0.7759	Intermediate Similarity	NPC72699
0.7727	Intermediate Similarity	NPC245947
0.7727	Intermediate Similarity	NPC136164
0.7727	Intermediate Similarity	NPC255863
0.7714	Intermediate Similarity	NPC470435
0.7714	Intermediate Similarity	NPC329890
0.7705	Intermediate Similarity	NPC473725
0.7705	Intermediate Similarity	NPC474913
0.7705	Intermediate Similarity	NPC473910
0.7705	Intermediate Similarity	NPC52264
0.7705	Intermediate Similarity	NPC473896
0.7705	Intermediate Similarity	NPC473721
0.7705	Intermediate Similarity	NPC473735
0.7705	Intermediate Similarity	NPC475353
0.7681	Intermediate Similarity	NPC4299
0.7667	Intermediate Similarity	NPC34577
0.7656	Intermediate Similarity	NPC327112
0.7627	Intermediate Similarity	NPC55383
0.7586	Intermediate Similarity	NPC153538
0.7586	Intermediate Similarity	NPC125122
0.7586	Intermediate Similarity	NPC471275
0.7586	Intermediate Similarity	NPC471280
0.7586	Intermediate Similarity	NPC471276
0.7544	Intermediate Similarity	NPC55063
0.7544	Intermediate Similarity	NPC35141
0.7544	Intermediate Similarity	NPC124183
0.7544	Intermediate Similarity	NPC19834
0.7541	Intermediate Similarity	NPC48058
0.7541	Intermediate Similarity	NPC137538
0.7541	Intermediate Similarity	NPC269615
0.7541	Intermediate Similarity	NPC473532
0.7538	Intermediate Similarity	NPC201939
0.7538	Intermediate Similarity	NPC321838
0.7538	Intermediate Similarity	NPC328776
0.7538	Intermediate Similarity	NPC320305
0.7536	Intermediate Similarity	NPC143396
0.7536	Intermediate Similarity	NPC101622
0.75	Intermediate Similarity	NPC148192
0.75	Intermediate Similarity	NPC330426
0.75	Intermediate Similarity	NPC22101
0.75	Intermediate Similarity	NPC127091
0.75	Intermediate Similarity	NPC104537
0.75	Intermediate Similarity	NPC25298
0.75	Intermediate Similarity	NPC473829
0.75	Intermediate Similarity	NPC475443
0.75	Intermediate Similarity	NPC271921
0.7465	Intermediate Similarity	NPC327383
0.7465	Intermediate Similarity	NPC185186
0.7465	Intermediate Similarity	NPC329914
0.7465	Intermediate Similarity	NPC477085
0.7463	Intermediate Similarity	NPC318420
0.7463	Intermediate Similarity	NPC326268
0.7458	Intermediate Similarity	NPC474642
0.7458	Intermediate Similarity	NPC477727
0.7458	Intermediate Similarity	NPC249670
0.7458	Intermediate Similarity	NPC473913
0.7458	Intermediate Similarity	NPC471281
0.7458	Intermediate Similarity	NPC199286
0.7429	Intermediate Similarity	NPC476037
0.7419	Intermediate Similarity	NPC471239
0.7397	Intermediate Similarity	NPC188860
0.7391	Intermediate Similarity	NPC48218
0.7391	Intermediate Similarity	NPC324981
0.7391	Intermediate Similarity	NPC473559
0.7391	Intermediate Similarity	NPC141481
0.7385	Intermediate Similarity	NPC243532
0.7385	Intermediate Similarity	NPC328311
0.7377	Intermediate Similarity	NPC477724
0.7377	Intermediate Similarity	NPC187361
0.7377	Intermediate Similarity	NPC26102
0.7368	Intermediate Similarity	NPC269074
0.7353	Intermediate Similarity	NPC146811
0.7333	Intermediate Similarity	NPC170776
0.7333	Intermediate Similarity	NPC93639
0.7333	Intermediate Similarity	NPC471959
0.7333	Intermediate Similarity	NPC224148
0.7333	Intermediate Similarity	NPC71053
0.7333	Intermediate Similarity	NPC9273
0.7333	Intermediate Similarity	NPC256656
0.7333	Intermediate Similarity	NPC76198
0.7333	Intermediate Similarity	NPC59408
0.7333	Intermediate Similarity	NPC165447
0.7333	Intermediate Similarity	NPC477723
0.7333	Intermediate Similarity	NPC89824
0.7333	Intermediate Similarity	NPC197272
0.7333	Intermediate Similarity	NPC475477
0.7333	Intermediate Similarity	NPC294278
0.7333	Intermediate Similarity	NPC329608
0.7324	Intermediate Similarity	NPC477087
0.7324	Intermediate Similarity	NPC477086
0.7313	Intermediate Similarity	NPC68343
0.7313	Intermediate Similarity	NPC328089
0.7302	Intermediate Similarity	NPC179764
0.7302	Intermediate Similarity	NPC324224
0.7302	Intermediate Similarity	NPC472808
0.7302	Intermediate Similarity	NPC187777
0.7297	Intermediate Similarity	NPC233071
0.7286	Intermediate Similarity	NPC236208
0.7286	Intermediate Similarity	NPC475004
0.7286	Intermediate Similarity	NPC130618
0.7286	Intermediate Similarity	NPC473772
0.7273	Intermediate Similarity	NPC55376
0.726	Intermediate Similarity	NPC260396
0.726	Intermediate Similarity	NPC327041
0.726	Intermediate Similarity	NPC285840
0.7246	Intermediate Similarity	NPC478097
0.7231	Intermediate Similarity	NPC159650
0.7231	Intermediate Similarity	NPC318306
0.7231	Intermediate Similarity	NPC22897
0.7213	Intermediate Similarity	NPC106531
0.7206	Intermediate Similarity	NPC19769
0.7206	Intermediate Similarity	NPC476657
0.7206	Intermediate Similarity	NPC478099
0.7206	Intermediate Similarity	NPC476655
0.7206	Intermediate Similarity	NPC478098
0.7206	Intermediate Similarity	NPC96414
0.7206	Intermediate Similarity	NPC476654
0.72	Intermediate Similarity	NPC248775
0.7193	Intermediate Similarity	NPC101616
0.7188	Intermediate Similarity	NPC474577
0.7183	Intermediate Similarity	NPC476660
0.7183	Intermediate Similarity	NPC42526
0.7183	Intermediate Similarity	NPC476012
0.7167	Intermediate Similarity	NPC328784
0.7167	Intermediate Similarity	NPC291437
0.7164	Intermediate Similarity	NPC54925
0.7143	Intermediate Similarity	NPC28779
0.7143	Intermediate Similarity	NPC474823
0.7143	Intermediate Similarity	NPC274290
0.7143	Intermediate Similarity	NPC54766
0.7143	Intermediate Similarity	NPC223677
0.7143	Intermediate Similarity	NPC475760
0.7143	Intermediate Similarity	NPC10316
0.7143	Intermediate Similarity	NPC473863
0.7143	Intermediate Similarity	NPC317899
0.7143	Intermediate Similarity	NPC200845
0.7143	Intermediate Similarity	NPC128061
0.7123	Intermediate Similarity	NPC227396
0.7121	Intermediate Similarity	NPC81896
0.7121	Intermediate Similarity	NPC321919
0.7105	Intermediate Similarity	NPC470149
0.7105	Intermediate Similarity	NPC470148
0.7105	Intermediate Similarity	NPC55304
0.7105	Intermediate Similarity	NPC1180

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 NPC271282 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	123
0.1-0.2	2969
0.2-0.3	3935
0.3-0.4	1665
0.4-0.5	336
0.5-0.6	77
0.6-0.7	43
0.7-0.8	2
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
0.7656	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3197	Phase 1
0.7013	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5331	Approved
0.6962	Remote Similarity	NPD5332	Approved
0.6825	Remote Similarity	NPD3172	Approved
0.679	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4268	Approved
0.6753	Remote Similarity	NPD4271	Approved
0.675	Remote Similarity	NPD7154	Phase 3
0.6719	Remote Similarity	NPD4266	Approved
0.6719	Remote Similarity	NPD3196	Approved
0.6719	Remote Similarity	NPD3194	Approved
0.6719	Remote Similarity	NPD3195	Phase 2
0.6714	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4819	Approved
0.6582	Remote Similarity	NPD4822	Approved
0.6582	Remote Similarity	NPD4820	Approved
0.6582	Remote Similarity	NPD4821	Approved
0.6567	Remote Similarity	NPD6109	Phase 1
0.6557	Remote Similarity	NPD5343	Approved
0.6543	Remote Similarity	NPD5362	Discontinued
0.6538	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD28	Approved
0.6508	Remote Similarity	NPD29	Approved
0.6506	Remote Similarity	NPD4249	Approved
0.6452	Remote Similarity	NPD3173	Approved
0.6429	Remote Similarity	NPD4251	Approved
0.6429	Remote Similarity	NPD4250	Approved
0.642	Remote Similarity	NPD4269	Approved
0.642	Remote Similarity	NPD4270	Approved
0.6375	Remote Similarity	NPD4252	Approved
0.6333	Remote Similarity	NPD6097	Approved
0.6333	Remote Similarity	NPD6096	Approved
0.631	Remote Similarity	NPD5786	Approved
0.6296	Remote Similarity	NPD4790	Discontinued
0.625	Remote Similarity	NPD6927	Phase 3
0.623	Remote Similarity	NPD4222	Approved
0.623	Remote Similarity	NPD39	Approved
0.623	Remote Similarity	NPD3174	Discontinued
0.623	Remote Similarity	NPD4265	Approved
0.622	Remote Similarity	NPD6435	Approved
0.6203	Remote Similarity	NPD4756	Discovery
0.619	Remote Similarity	NPD5363	Approved
0.619	Remote Similarity	NPD4220	Pre-registration
0.6136	Remote Similarity	NPD7983	Approved
0.6098	Remote Similarity	NPD5369	Approved
0.6092	Remote Similarity	NPD5370	Suspended
0.6087	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5779	Approved
0.6067	Remote Similarity	NPD5778	Approved
0.6032	Remote Similarity	NPD622	Approved
0.6023	Remote Similarity	NPD5785	Approved
0.6023	Remote Similarity	NPD7838	Discovery
0.5976	Remote Similarity	NPD5368	Approved
0.5972	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7637	Suspended
0.5949	Remote Similarity	NPD8039	Approved
0.5909	Remote Similarity	NPD6051	Approved
0.5902	Remote Similarity	NPD5326	Phase 3
0.589	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD342	Phase 1
0.587	Remote Similarity	NPD7839	Suspended
0.587	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD46	Approved
0.5843	Remote Similarity	NPD6698	Approved
0.5833	Remote Similarity	NPD4192	Approved
0.5833	Remote Similarity	NPD5209	Approved
0.5833	Remote Similarity	NPD4191	Approved
0.5833	Remote Similarity	NPD368	Approved
0.5833	Remote Similarity	NPD4193	Approved
0.5833	Remote Similarity	NPD4194	Approved
0.5745	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD3728	Approved
0.5735	Remote Similarity	NPD3730	Approved
0.573	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.573	Remote Similarity	NPD6101	Approved
0.5682	Remote Similarity	NPD7750	Discontinued
0.5652	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5344	Discontinued
0.5604	Remote Similarity	NPD6411	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