NPASS Compound

Structure

CID289979 OpenBabel06191716092D 23 22 0 0 1 0 0 0 0 0999 V2000 8.6603 8.0000 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 7.7942 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 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 4.3301 4.5000 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 3.4641 3.0000 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 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 -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 1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 3 0 0 0 0 2 17 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 18 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 16 23 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.25
Volume:	364.432
LogP:	3.828
LogD:	2.701
LogS:	-3.832
# Rotatable Bonds:	16
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	3.231
Fsp3:	0.842
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.773
MDCK Permeability:	3.382117211003788e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.337
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.58
Plasma Protein Binding (PPB):	95.20003509521484%
Volume Distribution (VD):	1.09
Pgp-substrate:	2.3576648235321045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.387
CYP1A2-substrate:	0.312
CYP2C19-inhibitor:	0.442
CYP2C19-substrate:	0.427
CYP2C9-inhibitor:	0.359
CYP2C9-substrate:	0.726
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	5.935
Half-life (T1/2):	0.58

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.602
Skin Sensitization:	0.946
Carcinogencity:	0.299
Eye Corrosion:	0.015
Eye Irritation:	0.421
Respiratory Toxicity:	0.81

Download Data

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

Natural Product: NPC289979

Natural Product ID:	NPC289979
*Common Name:**	Avocadyne Acetate
IUPAC Name:	2,4-dihydroxyheptadec-16-ynyl acetate
Synonyms:
Standard InCHIKey:	JAKAZHIACKJNNB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H34O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-18(21)15-19(22)16-23-17(2)20/h1,18-19,21-22H,4-16H2,2H3
SMILES:	C#CCCCCCCCCCCCC(CC(COC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1396170
PubChem CID:	3952079
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
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	fruit	n.a.	PMID[10820058]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Unripe fruit	n.a.	n.a.	PMID[9644064]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO16519	Persea americana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16519	Persea americana	Species	Lauraceae	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	2
Potency	14

Activity Type	# Activity
Individual Protein	14
Protein-Protein Interaction	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	39810.7	nM	PMID[553606]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	5011.9	nM	PMID[553606]
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	15848.9	nM	PMID[553606]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	15848.9	nM	PMID[553606]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	39810.7	nM	PMID[553606]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[553606]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[553606]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[553606]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	32.6	nM	PMID[553606]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	8.2	nM	PMID[553606]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	14125.4	nM	PMID[553606]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	14125.4	nM	PMID[553606]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[553606]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	109.89	%	PMID[553607]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	144.59	%	PMID[553607]

☑ 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 NPC289979 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	1015
0.1-0.2	8241
0.2-0.3	17396
0.3-0.4	11429
0.4-0.5	3669
0.5-0.6	809
0.6-0.7	119
0.7-0.8	12
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.82	Intermediate Similarity	NPC62014
0.8182	Intermediate Similarity	NPC469937
0.8182	Intermediate Similarity	NPC23155
0.8182	Intermediate Similarity	NPC320588
0.8182	Intermediate Similarity	NPC53463
0.7885	Intermediate Similarity	NPC8597
0.7636	Intermediate Similarity	NPC100096
0.75	Intermediate Similarity	NPC470363
0.7273	Intermediate Similarity	NPC26253
0.7273	Intermediate Similarity	NPC304162
0.72	Intermediate Similarity	NPC471282
0.7188	Intermediate Similarity	NPC471761
0.7188	Intermediate Similarity	NPC190418
0.7188	Intermediate Similarity	NPC471760
0.7143	Intermediate Similarity	NPC55678
0.7121	Intermediate Similarity	NPC82315
0.7091	Intermediate Similarity	NPC106872
0.7059	Intermediate Similarity	NPC152008
0.7	Intermediate Similarity	NPC197039
0.7	Intermediate Similarity	NPC148424
0.697	Remote Similarity	NPC206601
0.697	Remote Similarity	NPC469925
0.6909	Remote Similarity	NPC324004
0.6909	Remote Similarity	NPC328497
0.6866	Remote Similarity	NPC50228
0.6866	Remote Similarity	NPC97736
0.6866	Remote Similarity	NPC67099
0.6842	Remote Similarity	NPC90904
0.68	Remote Similarity	NPC128996
0.6792	Remote Similarity	NPC144829
0.6765	Remote Similarity	NPC211428
0.6765	Remote Similarity	NPC241265
0.6765	Remote Similarity	NPC285003
0.6765	Remote Similarity	NPC28526
0.6727	Remote Similarity	NPC30195
0.6727	Remote Similarity	NPC12438
0.6724	Remote Similarity	NPC287811
0.6716	Remote Similarity	NPC22101
0.6716	Remote Similarity	NPC330426
0.6716	Remote Similarity	NPC148192
0.6716	Remote Similarity	NPC271921
0.6716	Remote Similarity	NPC127091
0.6716	Remote Similarity	NPC104537
0.6667	Remote Similarity	NPC52268
0.6667	Remote Similarity	NPC321873
0.6667	Remote Similarity	NPC53760
0.6618	Remote Similarity	NPC324981
0.6618	Remote Similarity	NPC48218
0.6618	Remote Similarity	NPC473559
0.6618	Remote Similarity	NPC141481
0.6615	Remote Similarity	NPC29697
0.6615	Remote Similarity	NPC325773
0.6613	Remote Similarity	NPC322148
0.6613	Remote Similarity	NPC474577
0.66	Remote Similarity	NPC474914
0.66	Remote Similarity	NPC474392
0.6571	Remote Similarity	NPC184550
0.6571	Remote Similarity	NPC185419
0.6562	Remote Similarity	NPC477753
0.6562	Remote Similarity	NPC477755
0.6562	Remote Similarity	NPC477763
0.6562	Remote Similarity	NPC477750
0.6562	Remote Similarity	NPC477757
0.6562	Remote Similarity	NPC477762
0.6545	Remote Similarity	NPC47363
0.6545	Remote Similarity	NPC215358
0.6545	Remote Similarity	NPC287231
0.6545	Remote Similarity	NPC8219
0.6508	Remote Similarity	NPC320032
0.6491	Remote Similarity	NPC200618
0.6491	Remote Similarity	NPC131770
0.6481	Remote Similarity	NPC301528
0.6481	Remote Similarity	NPC129972
0.6481	Remote Similarity	NPC71317
0.6479	Remote Similarity	NPC206823
0.6479	Remote Similarity	NPC291228
0.6479	Remote Similarity	NPC163812
0.6479	Remote Similarity	NPC39266
0.6479	Remote Similarity	NPC308096
0.6479	Remote Similarity	NPC9763
0.6479	Remote Similarity	NPC225748
0.6479	Remote Similarity	NPC169085
0.6471	Remote Similarity	NPC473357
0.6471	Remote Similarity	NPC193029
0.6471	Remote Similarity	NPC475443
0.6471	Remote Similarity	NPC473829
0.6462	Remote Similarity	NPC475984
0.6462	Remote Similarity	NPC271282
0.6462	Remote Similarity	NPC325929
0.6462	Remote Similarity	NPC66460
0.6429	Remote Similarity	NPC473914
0.6429	Remote Similarity	NPC470268
0.6429	Remote Similarity	NPC476660
0.6418	Remote Similarity	NPC476655
0.6418	Remote Similarity	NPC76881
0.6418	Remote Similarity	NPC476654
0.6418	Remote Similarity	NPC12040
0.6418	Remote Similarity	NPC476657
0.6406	Remote Similarity	NPC174485
0.6406	Remote Similarity	NPC17935
0.64	Remote Similarity	NPC86545
0.64	Remote Similarity	NPC223374
0.64	Remote Similarity	NPC301398
0.64	Remote Similarity	NPC97967
0.64	Remote Similarity	NPC196442
0.6389	Remote Similarity	NPC472944
0.6389	Remote Similarity	NPC472945
0.6379	Remote Similarity	NPC82512
0.6364	Remote Similarity	NPC19305
0.6364	Remote Similarity	NPC255837
0.6364	Remote Similarity	NPC470965
0.6364	Remote Similarity	NPC235788
0.6349	Remote Similarity	NPC472025
0.6324	Remote Similarity	NPC476656
0.6324	Remote Similarity	NPC476659
0.6308	Remote Similarity	NPC321919
0.6308	Remote Similarity	NPC81896
0.6296	Remote Similarity	NPC163746
0.6296	Remote Similarity	NPC103286
0.6286	Remote Similarity	NPC473772
0.6269	Remote Similarity	NPC476658
0.6269	Remote Similarity	NPC314103
0.625	Remote Similarity	NPC470435
0.625	Remote Similarity	NPC469781
0.6232	Remote Similarity	NPC286842
0.6226	Remote Similarity	NPC225963
0.6226	Remote Similarity	NPC474205
0.6216	Remote Similarity	NPC477350
0.6216	Remote Similarity	NPC136424
0.6216	Remote Similarity	NPC470899
0.6212	Remote Similarity	NPC321838
0.62	Remote Similarity	NPC286498
0.6197	Remote Similarity	NPC33267
0.6197	Remote Similarity	NPC114640
0.6197	Remote Similarity	NPC126366
0.6197	Remote Similarity	NPC324165
0.6197	Remote Similarity	NPC169976
0.6197	Remote Similarity	NPC42526
0.6197	Remote Similarity	NPC170963
0.6182	Remote Similarity	NPC203531
0.6182	Remote Similarity	NPC236579
0.6176	Remote Similarity	NPC476330
0.6167	Remote Similarity	NPC124963
0.6167	Remote Similarity	NPC233726
0.6167	Remote Similarity	NPC23134
0.6164	Remote Similarity	NPC474321
0.6154	Remote Similarity	NPC74352
0.6143	Remote Similarity	NPC250619
0.6143	Remote Similarity	NPC273508
0.6143	Remote Similarity	NPC209327
0.614	Remote Similarity	NPC201948
0.6133	Remote Similarity	NPC476782
0.6133	Remote Similarity	NPC476781
0.6133	Remote Similarity	NPC476783
0.6133	Remote Similarity	NPC216883
0.6119	Remote Similarity	NPC277570
0.6111	Remote Similarity	NPC266553
0.6111	Remote Similarity	NPC474403
0.6087	Remote Similarity	NPC477752
0.6087	Remote Similarity	NPC477764
0.6087	Remote Similarity	NPC477756
0.6087	Remote Similarity	NPC477751
0.6081	Remote Similarity	NPC228411
0.6071	Remote Similarity	NPC70756
0.6071	Remote Similarity	NPC74845
0.6071	Remote Similarity	NPC320240
0.6071	Remote Similarity	NPC29721
0.6061	Remote Similarity	NPC472026
0.6056	Remote Similarity	NPC470436
0.6053	Remote Similarity	NPC475425
0.6053	Remote Similarity	NPC477326
0.6053	Remote Similarity	NPC252483
0.6053	Remote Similarity	NPC477328
0.6053	Remote Similarity	NPC477323
0.6053	Remote Similarity	NPC109887
0.6053	Remote Similarity	NPC43463
0.6053	Remote Similarity	NPC191345
0.6053	Remote Similarity	NPC113745
0.6053	Remote Similarity	NPC477325
0.6053	Remote Similarity	NPC477329
0.6053	Remote Similarity	NPC281563
0.6053	Remote Similarity	NPC477330
0.6053	Remote Similarity	NPC248775
0.6053	Remote Similarity	NPC477320
0.6053	Remote Similarity	NPC146380
0.6034	Remote Similarity	NPC321087
0.6034	Remote Similarity	NPC230789
0.6034	Remote Similarity	NPC277475
0.6034	Remote Similarity	NPC252918
0.6029	Remote Similarity	NPC476702
0.6027	Remote Similarity	NPC51249
0.6027	Remote Similarity	NPC475232
0.6027	Remote Similarity	NPC473699
0.6027	Remote Similarity	NPC475260
0.6027	Remote Similarity	NPC473775
0.6027	Remote Similarity	NPC474100
0.6	Remote Similarity	NPC72324
0.6	Remote Similarity	NPC216630
0.6	Remote Similarity	NPC193062
0.6	Remote Similarity	NPC139131

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 NPC289979 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1382
0.1-0.2	4747
0.2-0.3	1993
0.3-0.4	676
0.4-0.5	250
0.5-0.6	96
0.6-0.7	4
0.7-0.8	1
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
0.8182	Intermediate Similarity	NPD3730	Approved
0.8182	Intermediate Similarity	NPD3728	Approved
0.7091	Intermediate Similarity	NPD6125	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7536	Approved
0.6545	Remote Similarity	NPD2699	Approved
0.6452	Remote Similarity	NPD2267	Suspended
0.6393	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD9006	Approved
0.6066	Remote Similarity	NPD2269	Approved
0.6029	Remote Similarity	NPD7909	Approved
0.6	Remote Similarity	NPD5383	Approved
0.6	Remote Similarity	NPD2270	Approved
0.6	Remote Similarity	NPD2272	Approved
0.5902	Remote Similarity	NPD1400	Approved
0.5902	Remote Similarity	NPD1399	Approved
0.5902	Remote Similarity	NPD905	Approved
0.5902	Remote Similarity	NPD904	Phase 3
0.5893	Remote Similarity	NPD8957	Approved
0.5862	Remote Similarity	NPD8993	Phase 1
0.5862	Remote Similarity	NPD8998	Phase 2
0.5862	Remote Similarity	NPD8997	Approved
0.5862	Remote Similarity	NPD9000	Phase 3
0.5862	Remote Similarity	NPD8999	Phase 3
0.5846	Remote Similarity	NPD8959	Approved
0.58	Remote Similarity	NPD9636	Phase 2
0.5797	Remote Similarity	NPD3197	Phase 1
0.5769	Remote Similarity	NPD9053	Approved
0.5769	Remote Similarity	NPD9051	Approved
0.5769	Remote Similarity	NPD9052	Approved
0.5714	Remote Similarity	NPD893	Approved
0.5714	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD888	Phase 3
0.5714	Remote Similarity	NPD889	Approved
0.5714	Remote Similarity	NPD887	Approved
0.5714	Remote Similarity	NPD891	Phase 3
0.5714	Remote Similarity	NPD892	Phase 3
0.5714	Remote Similarity	NPD895	Approved
0.5714	Remote Similarity	NPD894	Approved
0.5692	Remote Similarity	NPD73	Approved
0.569	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.569	Remote Similarity	NPD9219	Approved
0.569	Remote Similarity	NPD9218	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD3198	Approved
0.5667	Remote Similarity	NPD2266	Phase 2
0.5667	Remote Similarity	NPD8965	Approved
0.5667	Remote Similarity	NPD8966	Approved
0.5636	Remote Similarity	NPD633	Phase 3
0.5636	Remote Similarity	NPD9655	Approved
0.5636	Remote Similarity	NPD9448	Phase 2
0.5616	Remote Similarity	NPD8277	Approved
0.5614	Remote Similarity	NPD8788	Approved
0.5614	Remote Similarity	NPD8958	Phase 2

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