NPASS Compound

Structure

NPC233003 OpenBabel07101719162D 54 59 0 0 1 0 0 0 0 0999 V2000 -3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.8660 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 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 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 2.0000 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 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 6.9282 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 1.0181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 2 0 0 0 0 5 39 1 0 0 0 0 6 39 1 0 0 0 0 8 41 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 29 1 0 0 0 0 13 17 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 30 1 0 0 0 0 16 40 1 0 0 0 0 17 41 1 0 0 0 0 18 42 1 0 0 0 0 19 43 1 0 0 0 0 20 27 1 0 0 0 0 20 51 1 0 0 0 0 21 22 1 0 0 0 0 23 4 1 1 0 0 0 23 24 1 0 0 0 0 24 41 1 1 0 0 0 25 26 2 0 0 0 0 25 40 1 0 0 0 0 26 42 1 0 0 0 0 27 31 1 0 0 0 0 27 44 1 6 0 0 0 28 19 1 6 0 0 0 28 32 1 0 0 0 0 28 52 1 0 0 0 0 29 39 1 0 0 0 0 29 40 1 1 0 0 0 30 39 1 0 0 0 0 30 53 1 1 0 0 0 31 35 1 0 0 0 0 31 45 1 6 0 0 0 32 33 1 0 0 0 0 32 46 1 6 0 0 0 33 34 1 0 0 0 0 33 47 1 6 0 0 0 34 36 1 0 0 0 0 34 48 1 1 0 0 0 35 37 1 0 0 0 0 35 54 1 1 0 0 0 36 52 1 0 0 0 0 36 54 1 6 0 0 0 37 51 1 0 0 0 0 37 53 1 6 0 0 0 38 49 2 0 0 0 0 38 50 1 0 0 0 0 40 7 1 1 0 0 0 41 42 1 1 0 0 0 42 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	764.47
Volume:	781.222
LogP:	4.339
LogD:	4.183
LogS:	-4.095
# Rotatable Bonds:	11
TPSA:	195.6
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.149
Synthetic Accessibility Score:	5.807
Fsp3:	0.881
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.695
MDCK Permeability:	1.2328180673648603e-05
Pgp-inhibitor:	0.768
Pgp-substrate:	0.082
Human Intestinal Absorption (HIA):	0.406
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.34

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	90.0953598022461%
Volume Distribution (VD):	0.765
Pgp-substrate:	3.786963939666748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.792
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	0.808
Half-life (T1/2):	0.331

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.241
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.584
Skin Sensitization:	0.034
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC233003

Natural Product ID:	NPC233003
*Common Name:**	Eryloside F1
IUPAC Name:	(3S,5R,10S,13R,14S,17R)-3-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,4,10,13-tetramethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid
Synonyms:	Eryloside F1
Standard InCHIKey:	SXNHMSNSEXAENW-RUQGLPSMSA-N
Standard InCHI:	InChI=1S/C42H68O12/c1-21(2)22(3)9-10-23(4)24-14-18-42(38(49)50)26-11-12-29-39(5,6)30(15-16-40(29,7)25(26)13-17-41(24,42)8)53-37-35(31(45)27(44)20-51-37)54-36-34(48)33(47)32(46)28(19-43)52-36/h21,23-24,27-37,43-48H,3,9-20H2,1-2,4-8H3,(H,49,50)/t23-,24-,27+,28-,29+,30+,31+,32+,33+,34-,35-,36+,37+,40-,41-,42+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC[C@@H]([C@@H]2O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CCC2=C3CC[C@]3([C@]2(CC[C@@H]3[C@@H](CCC(=C)C(C)C)C)C(=O)O)C)C)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL266770
PubChem CID:	16109764
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
NPO23881	Erylus formosus	Species	Geodiidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[17315957]
NPO23881	Erylus formosus	Species	Geodiidae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT610	Others	Molecular identity unknown		Activity	=	130.0	%	PMID[511334]

☑ 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 NPC233003 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	238
0.1-0.2	1514
0.2-0.3	4864
0.3-0.4	11410
0.4-0.5	9871
0.5-0.6	5861
0.6-0.7	4945
0.7-0.8	3092
0.8-0.85	571
0.85-0.9	299
0.9-0.95	25
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC251309
0.9712	High Similarity	NPC477073
0.9615	High Similarity	NPC129340
0.9612	High Similarity	NPC195708
0.9528	High Similarity	NPC477074
0.9519	High Similarity	NPC477069
0.9519	High Similarity	NPC265655
0.9519	High Similarity	NPC477070
0.9439	High Similarity	NPC473882
0.934	High Similarity	NPC250481
0.934	High Similarity	NPC292196
0.934	High Similarity	NPC285410
0.934	High Similarity	NPC263827
0.9252	High Similarity	NPC210420
0.9252	High Similarity	NPC474265
0.9245	High Similarity	NPC269095
0.9245	High Similarity	NPC78046
0.9238	High Similarity	NPC295389
0.9159	High Similarity	NPC108748
0.9159	High Similarity	NPC473481
0.9159	High Similarity	NPC297208
0.9159	High Similarity	NPC235841
0.9159	High Similarity	NPC211798
0.9159	High Similarity	NPC30397
0.9151	High Similarity	NPC51947
0.9151	High Similarity	NPC473844
0.9151	High Similarity	NPC137917
0.9135	High Similarity	NPC223741
0.9083	High Similarity	NPC116024
0.9083	High Similarity	NPC474557
0.9083	High Similarity	NPC220293
0.9074	High Similarity	NPC195132
0.9074	High Similarity	NPC256798
0.9074	High Similarity	NPC128925
0.9074	High Similarity	NPC161434
0.9065	High Similarity	NPC174679
0.9065	High Similarity	NPC56713
0.9065	High Similarity	NPC136877
0.9065	High Similarity	NPC114961
0.9065	High Similarity	NPC27551
0.9065	High Similarity	NPC475296
0.9065	High Similarity	NPC274507
0.9065	High Similarity	NPC474589
0.9065	High Similarity	NPC90856
0.9065	High Similarity	NPC52241
0.9065	High Similarity	NPC220984
0.9065	High Similarity	NPC279554
0.9065	High Similarity	NPC164194
0.9065	High Similarity	NPC475317
0.9065	High Similarity	NPC127056
0.9065	High Similarity	NPC29069
0.9065	High Similarity	NPC154856
0.9065	High Similarity	NPC270667
0.9065	High Similarity	NPC59804
0.9057	High Similarity	NPC88744
0.9048	High Similarity	NPC162033
0.9035	High Similarity	NPC130229
0.9	High Similarity	NPC279638
0.9	High Similarity	NPC244127
0.8991	High Similarity	NPC138334
0.8991	High Similarity	NPC189884
0.8991	High Similarity	NPC47063
0.8991	High Similarity	NPC258885
0.8991	High Similarity	NPC124296
0.8991	High Similarity	NPC204458
0.8981	High Similarity	NPC179434
0.8981	High Similarity	NPC91838
0.8981	High Similarity	NPC275668
0.8981	High Similarity	NPC164419
0.8981	High Similarity	NPC114188
0.8981	High Similarity	NPC240734
0.8981	High Similarity	NPC1876
0.8981	High Similarity	NPC204392
0.8981	High Similarity	NPC191763
0.8981	High Similarity	NPC190837
0.8981	High Similarity	NPC11035
0.8972	High Similarity	NPC91583
0.8972	High Similarity	NPC167383
0.8972	High Similarity	NPC57362
0.8972	High Similarity	NPC306746
0.8972	High Similarity	NPC204407
0.8972	High Similarity	NPC118225
0.8972	High Similarity	NPC237503
0.8972	High Similarity	NPC240125
0.8962	High Similarity	NPC293512
0.8962	High Similarity	NPC234160
0.8938	High Similarity	NPC202051
0.8919	High Similarity	NPC477252
0.8899	High Similarity	NPC475504
0.8899	High Similarity	NPC257468
0.8899	High Similarity	NPC104400
0.8899	High Similarity	NPC469946
0.8899	High Similarity	NPC104071
0.8899	High Similarity	NPC471383
0.8899	High Similarity	NPC46388
0.8899	High Similarity	NPC473383
0.8899	High Similarity	NPC116794
0.8899	High Similarity	NPC101744
0.8899	High Similarity	NPC109079
0.8899	High Similarity	NPC79718
0.8899	High Similarity	NPC212968
0.8899	High Similarity	NPC324875
0.8899	High Similarity	NPC80843
0.8899	High Similarity	NPC470543
0.8899	High Similarity	NPC102439
0.8899	High Similarity	NPC473373
0.8899	High Similarity	NPC65590
0.8899	High Similarity	NPC475516
0.8899	High Similarity	NPC1046
0.8899	High Similarity	NPC10320
0.8899	High Similarity	NPC125923
0.8899	High Similarity	NPC477253
0.8899	High Similarity	NPC37739
0.8899	High Similarity	NPC276093
0.8899	High Similarity	NPC139894
0.8899	High Similarity	NPC139044
0.8899	High Similarity	NPC292677
0.8899	High Similarity	NPC64106
0.8899	High Similarity	NPC130427
0.8889	High Similarity	NPC108709
0.8889	High Similarity	NPC476880
0.8889	High Similarity	NPC476884
0.8889	High Similarity	NPC7870
0.8889	High Similarity	NPC199457
0.8889	High Similarity	NPC476887
0.8889	High Similarity	NPC110139
0.8889	High Similarity	NPC101450
0.8889	High Similarity	NPC68419
0.8889	High Similarity	NPC476883
0.8889	High Similarity	NPC102914
0.8889	High Similarity	NPC476881
0.8889	High Similarity	NPC476882
0.8889	High Similarity	NPC476886
0.8889	High Similarity	NPC476885
0.8889	High Similarity	NPC75747
0.8879	High Similarity	NPC295980
0.8879	High Similarity	NPC38217
0.8879	High Similarity	NPC476123
0.8879	High Similarity	NPC285576
0.8879	High Similarity	NPC284807
0.8879	High Similarity	NPC28198
0.8879	High Similarity	NPC177246
0.8879	High Similarity	NPC472988
0.885	High Similarity	NPC471406
0.8839	High Similarity	NPC291564
0.8829	High Similarity	NPC161674
0.8829	High Similarity	NPC160415
0.8829	High Similarity	NPC471384
0.8829	High Similarity	NPC58448
0.8818	High Similarity	NPC200944
0.8818	High Similarity	NPC475287
0.8818	High Similarity	NPC475467
0.8818	High Similarity	NPC473343
0.8818	High Similarity	NPC146563
0.8818	High Similarity	NPC133818
0.8818	High Similarity	NPC134835
0.8818	High Similarity	NPC241909
0.8818	High Similarity	NPC219180
0.8818	High Similarity	NPC174720
0.8818	High Similarity	NPC192600
0.8818	High Similarity	NPC151543
0.8818	High Similarity	NPC323341
0.8818	High Similarity	NPC163183
0.8818	High Similarity	NPC251263
0.8818	High Similarity	NPC150400
0.8818	High Similarity	NPC46665
0.8818	High Similarity	NPC155410
0.8818	High Similarity	NPC114287
0.8818	High Similarity	NPC473826
0.8818	High Similarity	NPC73318
0.8818	High Similarity	NPC73455
0.8818	High Similarity	NPC260665
0.8818	High Similarity	NPC166422
0.8818	High Similarity	NPC295823
0.8818	High Similarity	NPC269315
0.8818	High Similarity	NPC238935
0.8818	High Similarity	NPC114304
0.8818	High Similarity	NPC271138
0.8818	High Similarity	NPC475208
0.8818	High Similarity	NPC96641
0.8818	High Similarity	NPC309714
0.8807	High Similarity	NPC31839
0.8807	High Similarity	NPC269466
0.8796	High Similarity	NPC125361
0.8796	High Similarity	NPC51925
0.8796	High Similarity	NPC127853
0.8796	High Similarity	NPC154085
0.8796	High Similarity	NPC296761
0.8796	High Similarity	NPC43976
0.8785	High Similarity	NPC287269
0.8785	High Similarity	NPC283849
0.8785	High Similarity	NPC473538
0.8783	High Similarity	NPC256983
0.8774	High Similarity	NPC470885
0.8774	High Similarity	NPC221562
0.8774	High Similarity	NPC187400
0.8772	High Similarity	NPC129434
0.8772	High Similarity	NPC475182
0.8762	High Similarity	NPC94919
0.8761	High Similarity	NPC232258

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 NPC233003 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1827
0.2-0.3	3946
0.3-0.4	2081
0.4-0.5	565
0.5-0.6	260
0.6-0.7	197
0.7-0.8	66
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8796	High Similarity	NPD8132	Clinical (unspecified phase)
0.8482	Intermediate Similarity	NPD8133	Approved
0.8421	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD6412	Phase 2
0.8151	Intermediate Similarity	NPD8328	Phase 3
0.8136	Intermediate Similarity	NPD8033	Approved
0.8051	Intermediate Similarity	NPD8294	Approved
0.8051	Intermediate Similarity	NPD8377	Approved
0.8017	Intermediate Similarity	NPD7507	Approved
0.7983	Intermediate Similarity	NPD8379	Approved
0.7983	Intermediate Similarity	NPD8335	Approved
0.7983	Intermediate Similarity	NPD8378	Approved
0.7983	Intermediate Similarity	NPD8296	Approved
0.7983	Intermediate Similarity	NPD8380	Approved
0.7876	Intermediate Similarity	NPD6686	Approved
0.7823	Intermediate Similarity	NPD7319	Approved
0.7742	Intermediate Similarity	NPD7736	Approved
0.7731	Intermediate Similarity	NPD7327	Approved
0.7731	Intermediate Similarity	NPD7328	Approved
0.7686	Intermediate Similarity	NPD8513	Phase 3
0.7686	Intermediate Similarity	NPD8516	Approved
0.7686	Intermediate Similarity	NPD8517	Approved
0.7686	Intermediate Similarity	NPD7503	Approved
0.7686	Intermediate Similarity	NPD8515	Approved
0.7667	Intermediate Similarity	NPD7516	Approved
0.7661	Intermediate Similarity	NPD8293	Discontinued
0.7611	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6399	Phase 3
0.748	Intermediate Similarity	NPD6370	Approved
0.7458	Intermediate Similarity	NPD8297	Approved
0.7458	Intermediate Similarity	NPD6882	Approved
0.7407	Intermediate Similarity	NPD8035	Phase 2
0.7407	Intermediate Similarity	NPD8034	Phase 2
0.736	Intermediate Similarity	NPD7492	Approved
0.7355	Intermediate Similarity	NPD6009	Approved
0.7317	Intermediate Similarity	NPD6054	Approved
0.7317	Intermediate Similarity	NPD6319	Approved
0.7317	Intermediate Similarity	NPD6059	Approved
0.7302	Intermediate Similarity	NPD6616	Approved
0.7273	Intermediate Similarity	NPD7748	Approved
0.725	Intermediate Similarity	NPD4632	Approved
0.7244	Intermediate Similarity	NPD7078	Approved
0.7241	Intermediate Similarity	NPD7128	Approved
0.7241	Intermediate Similarity	NPD6675	Approved
0.7241	Intermediate Similarity	NPD6402	Approved
0.7241	Intermediate Similarity	NPD5739	Approved
0.7232	Intermediate Similarity	NPD7902	Approved
0.7227	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7115	Discovery
0.7203	Intermediate Similarity	NPD6372	Approved
0.7203	Intermediate Similarity	NPD6373	Approved
0.7182	Intermediate Similarity	NPD8171	Discontinued
0.717	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD6067	Discontinued
0.712	Intermediate Similarity	NPD6016	Approved
0.712	Intermediate Similarity	NPD6015	Approved
0.7119	Intermediate Similarity	NPD7320	Approved
0.7119	Intermediate Similarity	NPD6899	Approved
0.7119	Intermediate Similarity	NPD6881	Approved
0.7105	Intermediate Similarity	NPD7639	Approved
0.7105	Intermediate Similarity	NPD7640	Approved
0.7091	Intermediate Similarity	NPD7515	Phase 2
0.7083	Intermediate Similarity	NPD6650	Approved
0.7083	Intermediate Similarity	NPD8130	Phase 1
0.7083	Intermediate Similarity	NPD6649	Approved
0.7075	Intermediate Similarity	NPD4786	Approved
0.7063	Intermediate Similarity	NPD5988	Approved
0.7059	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5697	Approved
0.7034	Intermediate Similarity	NPD5701	Approved
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6883	Approved
0.6964	Remote Similarity	NPD7900	Approved
0.6964	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6008	Approved
0.6942	Remote Similarity	NPD6869	Approved
0.6942	Remote Similarity	NPD6847	Approved
0.6942	Remote Similarity	NPD6617	Approved
0.6937	Remote Similarity	NPD6411	Approved
0.693	Remote Similarity	NPD6084	Phase 2
0.693	Remote Similarity	NPD6083	Phase 2
0.6917	Remote Similarity	NPD6012	Approved
0.6917	Remote Similarity	NPD6013	Approved
0.6917	Remote Similarity	NPD6014	Approved
0.6909	Remote Similarity	NPD5328	Approved
0.6903	Remote Similarity	NPD5695	Phase 3
0.6887	Remote Similarity	NPD3667	Approved
0.6875	Remote Similarity	NPD7604	Phase 2
0.686	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5983	Phase 2
0.6846	Remote Similarity	NPD8074	Phase 3
0.6842	Remote Similarity	NPD8449	Approved
0.6833	Remote Similarity	NPD6011	Approved
0.6803	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6033	Approved
0.6791	Remote Similarity	NPD8450	Suspended
0.6789	Remote Similarity	NPD3618	Phase 1
0.6786	Remote Similarity	NPD6079	Approved
0.6783	Remote Similarity	NPD4755	Approved
0.6769	Remote Similarity	NPD6336	Discontinued
0.6757	Remote Similarity	NPD6101	Approved
0.6757	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4202	Approved
0.6721	Remote Similarity	NPD4634	Approved
0.672	Remote Similarity	NPD6940	Discontinued
0.6696	Remote Similarity	NPD46	Approved
0.6696	Remote Similarity	NPD6698	Approved
0.6695	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD8336	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD8337	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6636	Remote Similarity	NPD5330	Approved
0.6636	Remote Similarity	NPD7521	Approved
0.6636	Remote Similarity	NPD7146	Approved
0.6636	Remote Similarity	NPD6409	Approved
0.6636	Remote Similarity	NPD6684	Approved
0.6636	Remote Similarity	NPD7334	Approved
0.6613	Remote Similarity	NPD6053	Discontinued
0.6612	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6274	Approved
0.6581	Remote Similarity	NPD5696	Approved
0.6581	Remote Similarity	NPD4225	Approved
0.6579	Remote Similarity	NPD5779	Approved
0.6579	Remote Similarity	NPD5778	Approved
0.6571	Remote Similarity	NPD6116	Phase 1
0.6562	Remote Similarity	NPD7101	Approved
0.6562	Remote Similarity	NPD7100	Approved
0.6555	Remote Similarity	NPD4633	Approved
0.6555	Remote Similarity	NPD5224	Approved
0.6555	Remote Similarity	NPD5211	Phase 2
0.6555	Remote Similarity	NPD5225	Approved
0.6555	Remote Similarity	NPD5226	Approved
0.6552	Remote Similarity	NPD4697	Phase 3
0.6552	Remote Similarity	NPD5221	Approved
0.6552	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5222	Approved
0.6542	Remote Similarity	NPD7525	Registered
0.6535	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4768	Approved
0.6529	Remote Similarity	NPD4767	Approved
0.6518	Remote Similarity	NPD6903	Approved
0.6514	Remote Similarity	NPD3669	Approved
0.6514	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD5175	Approved
0.6496	Remote Similarity	NPD5173	Approved
0.6491	Remote Similarity	NPD5284	Approved
0.6491	Remote Similarity	NPD7983	Approved
0.6491	Remote Similarity	NPD7637	Suspended
0.6491	Remote Similarity	NPD5281	Approved
0.6486	Remote Similarity	NPD5279	Phase 3
0.6484	Remote Similarity	NPD6335	Approved
0.6476	Remote Similarity	NPD6117	Approved
0.6471	Remote Similarity	NPD5223	Approved
0.6471	Remote Similarity	NPD8338	Approved
0.6466	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6908	Approved
0.6462	Remote Similarity	NPD6909	Approved
0.646	Remote Similarity	NPD4753	Phase 2
0.6458	Remote Similarity	NPD7625	Phase 1
0.6457	Remote Similarity	NPD6868	Approved
0.6455	Remote Similarity	NPD3133	Approved
0.6455	Remote Similarity	NPD3666	Approved
0.6455	Remote Similarity	NPD3665	Phase 1
0.6455	Remote Similarity	NPD3668	Phase 3
0.6449	Remote Similarity	NPD7645	Phase 2
0.6446	Remote Similarity	NPD5141	Approved
0.6441	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7524	Approved
0.6423	Remote Similarity	NPD4729	Approved
0.6423	Remote Similarity	NPD4730	Approved
0.6406	Remote Similarity	NPD6317	Approved
0.6397	Remote Similarity	NPD7260	Phase 2
0.6381	Remote Similarity	NPD6942	Approved
0.6381	Remote Similarity	NPD7339	Approved
0.6364	Remote Similarity	NPD4754	Approved
0.6364	Remote Similarity	NPD7122	Discontinued
0.6357	Remote Similarity	NPD6313	Approved
0.6357	Remote Similarity	NPD6314	Approved
0.6348	Remote Similarity	NPD6050	Approved
0.6339	Remote Similarity	NPD6098	Approved
0.6336	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.633	Remote Similarity	NPD1780	Approved
0.633	Remote Similarity	NPD1779	Approved
0.6324	Remote Similarity	NPD5956	Approved
0.632	Remote Similarity	NPD5250	Approved
0.632	Remote Similarity	NPD5248	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