NPASS Compound

Structure

NPC473357 OpenBabel07101719512D 41 40 0 0 1 0 0 0 0 0999 V2000 4.6962 6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 7.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8923 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 2.0000 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 4.6962 8.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8301 8.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 5.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 8.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8301 7.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 5.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2942 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1603 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1603 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 7.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2942 4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0263 2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3660 1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8923 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3660 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0263 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8923 3.8660 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 -2.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 33 1 0 0 0 0 8 33 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 25 2 0 0 0 0 15 26 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 27 2 0 0 0 0 19 28 2 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 28 1 0 0 0 0 22 31 1 0 0 0 0 24 34 1 0 0 0 0 24 40 1 0 0 0 0 29 35 2 0 0 0 0 29 40 1 0 0 0 0 30 36 2 0 0 0 0 30 41 1 0 0 0 0 31 33 1 0 0 0 0 31 37 1 6 0 0 0 32 23 1 1 0 0 0 32 34 1 0 0 0 0 32 41 1 0 0 0 0 33 38 1 0 0 0 0 34 9 1 6 0 0 0 34 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.42
Volume:	642.333
LogP:	5.818
LogD:	4.313
LogS:	-3.593
# Rotatable Bonds:	22
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	0
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.081
Synthetic Accessibility Score:	4.559
Fsp3:	0.706
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.858
MDCK Permeability:	2.2305233869701624e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.853
20% Bioavailability (F20%):	0.656
30% Bioavailability (F30%):	0.568

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.583
Plasma Protein Binding (PPB):	90.18840789794922%
Volume Distribution (VD):	0.937
Pgp-substrate:	4.080086708068848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.127
CYP2C9-inhibitor:	0.195
CYP2C9-substrate:	0.681
CYP2D6-inhibitor:	0.565
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.616
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	3.263
Half-life (T1/2):	0.42

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.309
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.0
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.967
Carcinogencity:	0.006
Eye Corrosion:	0.004
Eye Irritation:	0.191
Respiratory Toxicity:	0.001

Download Data

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

Natural Product: NPC473357

Natural Product ID:	NPC473357
*Common Name:**	[(2S,3R,6E,10E,14E,18E,22R)-3-Acetyloxy-2,22,23-Trihydroxy-2,6,10,15,19,23-Hexamethyltetracosa-6,10,14,18-Tetraenyl] Acetate
IUPAC Name:	[(2S,3R,6E,10E,14E,18E,22R)-3-acetyloxy-2,22,23-trihydroxy-2,6,10,15,19,23-hexamethyltetracosa-6,10,14,18-tetraenyl] acetate
Synonyms:
Standard InCHIKey:	WVMDVHDOEYMXEG-JWJOUKKDSA-N
Standard InCHI:	InChI=1S/C34H58O7/c1-25(16-12-18-27(3)20-22-31(37)33(7,8)38)14-10-11-15-26(2)17-13-19-28(4)21-23-32(41-30(6)36)34(9,39)24-40-29(5)35/h14-15,18-19,31-32,37-39H,10-13,16-17,20-24H2,1-9H3/b25-14+,26-15+,27-18+,28-19+/t31-,32-,34+/m1/s1
SMILES:	CC(=CCCC=C(C)CCC=C(C)CCC(C(C)(COC(=O)C)O)OC(=O)C)CCC=C(C)CCC(C(C)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402771
PubChem CID:	44448270
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO9975	Ekebergia capensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220356]
NPO9975	Ekebergia capensis	Species	Meliaceae	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

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	113000.0	nM	PMID[508262]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	97000.0	nM	PMID[508262]

☑ 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 NPC473357 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	163
0.1-0.2	1944
0.2-0.3	7793
0.3-0.4	16467
0.4-0.5	8145
0.5-0.6	6529
0.6-0.7	1530
0.7-0.8	113
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC193029
0.8548	High Similarity	NPC52012
0.8382	Intermediate Similarity	NPC209327
0.8382	Intermediate Similarity	NPC273508
0.8356	Intermediate Similarity	NPC3852
0.8308	Intermediate Similarity	NPC64971
0.8226	Intermediate Similarity	NPC281590
0.8219	Intermediate Similarity	NPC40049
0.8116	Intermediate Similarity	NPC48218
0.8116	Intermediate Similarity	NPC473559
0.8116	Intermediate Similarity	NPC141481
0.8116	Intermediate Similarity	NPC324981
0.8056	Intermediate Similarity	NPC160540
0.8026	Intermediate Similarity	NPC474894
0.8	Intermediate Similarity	NPC101622
0.8	Intermediate Similarity	NPC278202
0.7971	Intermediate Similarity	NPC330426
0.7971	Intermediate Similarity	NPC104537
0.7971	Intermediate Similarity	NPC473829
0.7971	Intermediate Similarity	NPC127091
0.7971	Intermediate Similarity	NPC271921
0.7971	Intermediate Similarity	NPC148192
0.7971	Intermediate Similarity	NPC22101
0.7971	Intermediate Similarity	NPC475443
0.7895	Intermediate Similarity	NPC103634
0.7887	Intermediate Similarity	NPC329904
0.7887	Intermediate Similarity	NPC476660
0.7887	Intermediate Similarity	NPC473361
0.7887	Intermediate Similarity	NPC4299
0.7879	Intermediate Similarity	NPC81896
0.7879	Intermediate Similarity	NPC321919
0.7857	Intermediate Similarity	NPC310210
0.7838	Intermediate Similarity	NPC469880
0.7838	Intermediate Similarity	NPC477202
0.7826	Intermediate Similarity	NPC476656
0.7826	Intermediate Similarity	NPC476659
0.7794	Intermediate Similarity	NPC476658
0.7763	Intermediate Similarity	NPC471537
0.7746	Intermediate Similarity	NPC16964
0.7746	Intermediate Similarity	NPC329656
0.7746	Intermediate Similarity	NPC473772
0.7733	Intermediate Similarity	NPC477203
0.7681	Intermediate Similarity	NPC476657
0.7681	Intermediate Similarity	NPC476655
0.7681	Intermediate Similarity	NPC476654
0.7632	Intermediate Similarity	NPC218817
0.7632	Intermediate Similarity	NPC11796
0.76	Intermediate Similarity	NPC470899
0.7595	Intermediate Similarity	NPC231601
0.7571	Intermediate Similarity	NPC137163
0.7568	Intermediate Similarity	NPC107654
0.7534	Intermediate Similarity	NPC477087
0.7534	Intermediate Similarity	NPC477086
0.75	Intermediate Similarity	NPC55376
0.75	Intermediate Similarity	NPC321838
0.75	Intermediate Similarity	NPC78673
0.75	Intermediate Similarity	NPC9868
0.75	Intermediate Similarity	NPC186155
0.75	Intermediate Similarity	NPC84360
0.75	Intermediate Similarity	NPC160517
0.75	Intermediate Similarity	NPC472947
0.7432	Intermediate Similarity	NPC477085
0.7432	Intermediate Similarity	NPC476709
0.7407	Intermediate Similarity	NPC11804
0.7407	Intermediate Similarity	NPC471494
0.7407	Intermediate Similarity	NPC477747
0.7407	Intermediate Similarity	NPC477746
0.7397	Intermediate Similarity	NPC42526
0.7391	Intermediate Similarity	NPC54925
0.7385	Intermediate Similarity	NPC227135
0.7375	Intermediate Similarity	NPC49208
0.7375	Intermediate Similarity	NPC23748
0.7375	Intermediate Similarity	NPC161045
0.7368	Intermediate Similarity	NPC301525
0.7353	Intermediate Similarity	NPC469694
0.7349	Intermediate Similarity	NPC309656
0.7333	Intermediate Similarity	NPC471525
0.7333	Intermediate Similarity	NPC474321
0.7333	Intermediate Similarity	NPC315843
0.7333	Intermediate Similarity	NPC104644
0.7333	Intermediate Similarity	NPC474280
0.7317	Intermediate Similarity	NPC61527
0.7317	Intermediate Similarity	NPC311163
0.7308	Intermediate Similarity	NPC325869
0.7308	Intermediate Similarity	NPC86971
0.7297	Intermediate Similarity	NPC306085
0.7297	Intermediate Similarity	NPC472254
0.7284	Intermediate Similarity	NPC474776
0.7284	Intermediate Similarity	NPC243618
0.7284	Intermediate Similarity	NPC70424
0.7273	Intermediate Similarity	NPC476703
0.7273	Intermediate Similarity	NPC474278
0.725	Intermediate Similarity	NPC474291
0.7237	Intermediate Similarity	NPC93213
0.7237	Intermediate Similarity	NPC199445
0.7237	Intermediate Similarity	NPC113639
0.7229	Intermediate Similarity	NPC179659
0.7229	Intermediate Similarity	NPC248602
0.7222	Intermediate Similarity	NPC25298
0.7215	Intermediate Similarity	NPC233377
0.7215	Intermediate Similarity	NPC472948
0.7215	Intermediate Similarity	NPC200446
0.7209	Intermediate Similarity	NPC320089
0.7206	Intermediate Similarity	NPC475931
0.72	Intermediate Similarity	NPC470435
0.7195	Intermediate Similarity	NPC475206
0.7176	Intermediate Similarity	NPC478003
0.7176	Intermediate Similarity	NPC313670
0.7176	Intermediate Similarity	NPC478004
0.7176	Intermediate Similarity	NPC158388
0.7164	Intermediate Similarity	NPC323436
0.7162	Intermediate Similarity	NPC129630
0.716	Intermediate Similarity	NPC44261
0.716	Intermediate Similarity	NPC474809
0.716	Intermediate Similarity	NPC11620
0.7143	Intermediate Similarity	NPC217940
0.7143	Intermediate Similarity	NPC29697
0.7143	Intermediate Similarity	NPC201046
0.7125	Intermediate Similarity	NPC8538
0.7125	Intermediate Similarity	NPC315731
0.7125	Intermediate Similarity	NPC118116
0.7125	Intermediate Similarity	NPC112868
0.7125	Intermediate Similarity	NPC184208
0.7125	Intermediate Similarity	NPC475944
0.7123	Intermediate Similarity	NPC272961
0.7108	Intermediate Similarity	NPC472009
0.7105	Intermediate Similarity	NPC477204
0.7105	Intermediate Similarity	NPC474551
0.7093	Intermediate Similarity	NPC184463
0.7093	Intermediate Similarity	NPC472197
0.7093	Intermediate Similarity	NPC472199
0.7089	Intermediate Similarity	NPC476701
0.7089	Intermediate Similarity	NPC475210
0.7089	Intermediate Similarity	NPC209995
0.7089	Intermediate Similarity	NPC477088
0.7089	Intermediate Similarity	NPC470149
0.7089	Intermediate Similarity	NPC139712
0.7089	Intermediate Similarity	NPC470148
0.7083	Intermediate Similarity	NPC83965
0.7077	Intermediate Similarity	NPC474496
0.7073	Intermediate Similarity	NPC163093
0.7073	Intermediate Similarity	NPC72464
0.7067	Intermediate Similarity	NPC316185
0.7067	Intermediate Similarity	NPC477084
0.7067	Intermediate Similarity	NPC477981
0.7067	Intermediate Similarity	NPC477983
0.7059	Intermediate Similarity	NPC133450
0.7059	Intermediate Similarity	NPC477748
0.7051	Intermediate Similarity	NPC476439
0.7051	Intermediate Similarity	NPC283619
0.7037	Intermediate Similarity	NPC329829
0.7037	Intermediate Similarity	NPC65930
0.7037	Intermediate Similarity	NPC474252
0.7037	Intermediate Similarity	NPC180363
0.7037	Intermediate Similarity	NPC11332
0.7037	Intermediate Similarity	NPC73310
0.7037	Intermediate Similarity	NPC473712
0.7037	Intermediate Similarity	NPC94875
0.7037	Intermediate Similarity	NPC145914
0.7037	Intermediate Similarity	NPC473780
0.7037	Intermediate Similarity	NPC131002
0.7037	Intermediate Similarity	NPC473529
0.7037	Intermediate Similarity	NPC475159
0.7027	Intermediate Similarity	NPC329989
0.7027	Intermediate Similarity	NPC130618
0.7027	Intermediate Similarity	NPC239373
0.7027	Intermediate Similarity	NPC269841
0.7027	Intermediate Similarity	NPC470436
0.7024	Intermediate Similarity	NPC474765
0.7024	Intermediate Similarity	NPC245004
0.7024	Intermediate Similarity	NPC472007
0.7013	Intermediate Similarity	NPC329852
0.7011	Intermediate Similarity	NPC472195
0.7011	Intermediate Similarity	NPC238090
0.7011	Intermediate Similarity	NPC472196
0.7	Intermediate Similarity	NPC271282
0.7	Intermediate Similarity	NPC474739
0.7	Intermediate Similarity	NPC201939
0.7	Intermediate Similarity	NPC100697
0.7	Intermediate Similarity	NPC320305
0.7	Intermediate Similarity	NPC470147
0.7	Intermediate Similarity	NPC133226
0.7	Intermediate Similarity	NPC325929
0.7	Intermediate Similarity	NPC328776
0.7	Intermediate Similarity	NPC127295
0.7	Intermediate Similarity	NPC163362
0.7	Intermediate Similarity	NPC66460
0.7	Intermediate Similarity	NPC475251
0.6988	Remote Similarity	NPC137033
0.6988	Remote Similarity	NPC471567
0.6988	Remote Similarity	NPC242233
0.6988	Remote Similarity	NPC477014
0.6988	Remote Similarity	NPC477013
0.6988	Remote Similarity	NPC120398
0.6986	Remote Similarity	NPC26500
0.6986	Remote Similarity	NPC99619
0.6986	Remote Similarity	NPC472266
0.6986	Remote Similarity	NPC478100
0.6986	Remote Similarity	NPC259299
0.6977	Remote Similarity	NPC472466

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 NPC473357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	2476
0.2-0.3	3868
0.3-0.4	1863
0.4-0.5	586
0.5-0.6	190
0.6-0.7	34
0.7-0.8	1
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
0.7176	Intermediate Similarity	NPD7838	Discovery
0.7093	Intermediate Similarity	NPD7983	Approved
0.7059	Intermediate Similarity	NPD6109	Phase 1
0.7042	Intermediate Similarity	NPD3197	Phase 1
0.6977	Remote Similarity	NPD6698	Approved
0.6977	Remote Similarity	NPD46	Approved
0.6951	Remote Similarity	NPD7154	Phase 3
0.6944	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6435	Approved
0.679	Remote Similarity	NPD4821	Approved
0.679	Remote Similarity	NPD4819	Approved
0.679	Remote Similarity	NPD4822	Approved
0.679	Remote Similarity	NPD4820	Approved
0.679	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5369	Approved
0.662	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5368	Approved
0.6548	Remote Similarity	NPD5362	Discontinued
0.6543	Remote Similarity	NPD4268	Approved
0.6543	Remote Similarity	NPD4271	Approved
0.6489	Remote Similarity	NPD5344	Discontinued
0.6477	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6101	Approved
0.6471	Remote Similarity	NPD3730	Approved
0.6471	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3728	Approved
0.6452	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7524	Approved
0.6353	Remote Similarity	NPD5332	Approved
0.6353	Remote Similarity	NPD5331	Approved
0.6341	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6411	Approved
0.631	Remote Similarity	NPD4790	Discontinued
0.6301	Remote Similarity	NPD368	Approved
0.6296	Remote Similarity	NPD6933	Approved
0.6277	Remote Similarity	NPD4225	Approved
0.6264	Remote Similarity	NPD5778	Approved
0.6264	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD4251	Approved
0.6237	Remote Similarity	NPD7839	Suspended
0.6235	Remote Similarity	NPD4270	Approved
0.6235	Remote Similarity	NPD4269	Approved
0.6232	Remote Similarity	NPD4266	Approved
0.6232	Remote Similarity	NPD3196	Approved
0.6232	Remote Similarity	NPD3194	Approved
0.6232	Remote Similarity	NPD3195	Phase 2
0.6184	Remote Similarity	NPD7331	Phase 2
0.6173	Remote Similarity	NPD8039	Approved
0.6163	Remote Similarity	NPD6695	Phase 3
0.6162	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7637	Suspended
0.6145	Remote Similarity	NPD3732	Approved
0.6136	Remote Similarity	NPD4249	Approved
0.6136	Remote Similarity	NPD5786	Approved
0.6104	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3172	Approved
0.6078	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7750	Discontinued
0.6064	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5343	Approved
0.6049	Remote Similarity	NPD6926	Approved
0.6049	Remote Similarity	NPD6924	Approved
0.6042	Remote Similarity	NPD6648	Approved
0.6029	Remote Similarity	NPD6927	Phase 3
0.6023	Remote Similarity	NPD5363	Approved
0.6023	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD39	Approved
0.6	Remote Similarity	NPD4265	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6371	Approved
0.5977	Remote Similarity	NPD6110	Phase 1
0.597	Remote Similarity	NPD3173	Approved
0.5955	Remote Similarity	NPD6422	Discontinued
0.5941	Remote Similarity	NPD6686	Approved
0.5921	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD7909	Approved
0.5915	Remote Similarity	NPD342	Phase 1
0.5914	Remote Similarity	NPD6399	Phase 3
0.589	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7645	Phase 2
0.587	Remote Similarity	NPD5785	Approved
0.5865	Remote Similarity	NPD8297	Approved
0.5846	Remote Similarity	NPD6097	Approved
0.5846	Remote Similarity	NPD6096	Approved
0.5833	Remote Similarity	NPD6932	Approved
0.5833	Remote Similarity	NPD7902	Approved
0.5821	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6931	Approved
0.5814	Remote Similarity	NPD7525	Registered
0.5814	Remote Similarity	NPD6930	Phase 2
0.5806	Remote Similarity	NPD7515	Phase 2
0.5797	Remote Similarity	NPD28	Approved
0.5797	Remote Similarity	NPD29	Approved
0.5789	Remote Similarity	NPD5695	Phase 3
0.5789	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD8264	Approved
0.5773	Remote Similarity	NPD7638	Approved
0.5761	Remote Similarity	NPD5370	Suspended
0.5761	Remote Similarity	NPD6051	Approved
0.5758	Remote Similarity	NPD4222	Approved
0.575	Remote Similarity	NPD6922	Approved
0.575	Remote Similarity	NPD6923	Approved
0.5743	Remote Similarity	NPD6675	Approved
0.5743	Remote Similarity	NPD6402	Approved
0.5743	Remote Similarity	NPD5739	Approved
0.5743	Remote Similarity	NPD7128	Approved
0.5733	Remote Similarity	NPD1145	Discontinued
0.5732	Remote Similarity	NPD4732	Discontinued
0.5714	Remote Similarity	NPD818	Approved
0.5714	Remote Similarity	NPD819	Approved
0.5714	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD7640	Approved
0.5699	Remote Similarity	NPD3168	Discontinued
0.5698	Remote Similarity	NPD6683	Phase 2
0.5698	Remote Similarity	NPD6929	Approved
0.5692	Remote Similarity	NPD5326	Phase 3
0.5686	Remote Similarity	NPD6412	Phase 2
0.5679	Remote Similarity	NPD7143	Approved
0.5679	Remote Similarity	NPD7144	Approved
0.5648	Remote Similarity	NPD7115	Discovery
0.5647	Remote Similarity	NPD4756	Discovery
0.5647	Remote Similarity	NPD6925	Approved
0.5647	Remote Similarity	NPD5776	Phase 2
0.5641	Remote Similarity	NPD7341	Phase 2
0.5638	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD7087	Discontinued
0.5636	Remote Similarity	NPD8377	Approved
0.5636	Remote Similarity	NPD8294	Approved
0.5632	Remote Similarity	NPD7514	Phase 3
0.5632	Remote Similarity	NPD7332	Phase 2
0.5632	Remote Similarity	NPD7509	Discontinued
0.5631	Remote Similarity	NPD6899	Approved
0.5631	Remote Similarity	NPD6881	Approved
0.5631	Remote Similarity	NPD7320	Approved
0.5619	Remote Similarity	NPD8130	Phase 1
0.5612	Remote Similarity	NPD5696	Approved
0.561	Remote Similarity	NPD7152	Approved
0.561	Remote Similarity	NPD7151	Approved
0.561	Remote Similarity	NPD7150	Approved
0.5604	Remote Similarity	NPD7334	Approved
0.5604	Remote Similarity	NPD5330	Approved
0.5604	Remote Similarity	NPD7146	Approved
0.5604	Remote Similarity	NPD7521	Approved
0.5604	Remote Similarity	NPD6684	Approved
0.5604	Remote Similarity	NPD6409	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