NPASS Compound

Structure

NPC100383 OpenBabel07101719512D 43 48 0 0 1 0 0 0 0 0999 V2000 -4.4953 -0.4564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0189 1.0861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5246 -1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 -1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 -2.9388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 -2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2418 1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0901 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0349 -0.6210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5451 0.4898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9385 -1.4694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6967 -0.9796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5451 -2.4490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9385 -2.4490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0901 -2.9388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2418 -2.4490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5451 2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2418 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 -1.4694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5451 -1.4694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8484 0.4898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5451 1.4694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0144 -0.6210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7868 -0.9796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7868 -2.9388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0901 -3.9184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6967 2.9388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3934 2.9388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2418 -1.4694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3934 -2.9388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 30 1 0 0 0 0 5 33 1 0 0 0 0 7 8 1 0 0 0 0 7 20 2 0 0 0 0 8 24 1 0 0 0 0 9 12 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 31 1 0 0 0 0 12 34 1 0 0 0 0 13 15 1 0 0 0 0 13 30 1 0 0 0 0 14 16 1 0 0 0 0 14 33 1 0 0 0 0 15 35 1 0 0 0 0 16 35 1 0 0 0 0 17 21 1 0 0 0 0 17 30 1 0 0 0 0 18 22 1 0 0 0 0 18 42 1 0 0 0 0 19 32 1 0 0 0 0 19 36 2 0 0 0 0 20 21 1 0 0 0 0 20 33 1 0 0 0 0 21 35 1 6 0 0 0 22 26 1 0 0 0 0 22 37 1 6 0 0 0 23 31 1 1 0 0 0 23 32 1 0 0 0 0 24 31 1 1 0 0 0 24 34 1 0 0 0 0 25 32 1 1 0 0 0 25 43 1 0 0 0 0 26 27 1 0 0 0 0 26 38 1 6 0 0 0 27 28 1 0 0 0 0 27 39 1 1 0 0 0 28 42 1 0 0 0 0 28 43 1 6 0 0 0 29 40 2 0 0 0 0 29 41 1 0 0 0 0 31 3 1 1 0 0 0 32 4 1 1 0 0 0 33 34 1 1 0 0 0 34 6 1 1 0 0 0 35 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.38
Volume:	624.99
LogP:	4.022
LogD:	3.825
LogS:	-4.014
# Rotatable Bonds:	4
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	5.339
Fsp3:	0.886
Lipinski Rule-of-5:	Accepted
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:	-5.475
MDCK Permeability:	1.345948112430051e-05
Pgp-inhibitor:	0.485
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.394

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.894
Plasma Protein Binding (PPB):	76.8425521850586%
Volume Distribution (VD):	0.591
Pgp-substrate:	14.55083179473877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.406
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	0.939
Half-life (T1/2):	0.177

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.288
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.852
Skin Sensitization:	0.262
Carcinogencity:	0.193
Eye Corrosion:	0.027
Eye Irritation:	0.021
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC100383

Natural Product ID:	NPC100383
*Common Name:**	3Beta-[(Alpha-Larabinopyranosyl)Oxy]-23-Oxo-Olean-12-En-28-Oic Acid
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	QNJNYLJSUQIOBL-RITZIESXSA-N
Standard InCHI:	InChI=1S/C35H54O8/c1-30(2)13-15-35(29(40)41)16-14-33(5)20(21(35)17-30)7-8-24-31(3)11-10-25(43-28-27(39)26(38)22(37)18-42-28)32(4,19-36)23(31)9-12-34(24,33)6/h7,19,21-28,37-39H,8-18H2,1-6H3,(H,40,41)/t21-,22-,23+,24+,25-,26-,27+,28-,31-,32-,33+,34+,35-/m0/s1
SMILES:	O=C[C@]1(C)[C@H](CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL540458
PubChem CID:	44179589
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
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	Eukaryota	underground parts	n.a.	n.a.	PMID[19449879]
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4.8	ug.mL-1	PMID[477084]

☑ 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 NPC100383 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	266
0.1-0.2	1777
0.2-0.3	5231
0.3-0.4	11871
0.4-0.5	10627
0.5-0.6	6215
0.6-0.7	3868
0.7-0.8	1836
0.8-0.85	482
0.85-0.9	178
0.9-0.95	269
0.95-1	77

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC242611
0.9712	High Similarity	NPC31839
0.9626	High Similarity	NPC323359
0.9619	High Similarity	NPC80843
0.9619	High Similarity	NPC1046
0.9619	High Similarity	NPC48249
0.9612	High Similarity	NPC28198
0.9612	High Similarity	NPC284807
0.9612	High Similarity	NPC177246
0.9612	High Similarity	NPC476123
0.9537	High Similarity	NPC473459
0.9528	High Similarity	NPC475208
0.9528	High Similarity	NPC238935
0.9519	High Similarity	NPC127853
0.9519	High Similarity	NPC306746
0.9519	High Similarity	NPC167383
0.9519	High Similarity	NPC237503
0.9519	High Similarity	NPC204407
0.9519	High Similarity	NPC57362
0.9515	High Similarity	NPC283849
0.9515	High Similarity	NPC473538
0.945	High Similarity	NPC473386
0.9439	High Similarity	NPC164389
0.9439	High Similarity	NPC475486
0.9429	High Similarity	NPC476884
0.9429	High Similarity	NPC108709
0.9429	High Similarity	NPC270667
0.9429	High Similarity	NPC199457
0.9429	High Similarity	NPC476882
0.9429	High Similarity	NPC474589
0.9429	High Similarity	NPC102914
0.9429	High Similarity	NPC29069
0.9429	High Similarity	NPC75747
0.9429	High Similarity	NPC476880
0.9429	High Similarity	NPC476886
0.9429	High Similarity	NPC476883
0.9429	High Similarity	NPC476881
0.9429	High Similarity	NPC110139
0.9429	High Similarity	NPC164194
0.9429	High Similarity	NPC68419
0.9429	High Similarity	NPC127056
0.9429	High Similarity	NPC136877
0.9429	High Similarity	NPC56713
0.9429	High Similarity	NPC274507
0.9429	High Similarity	NPC476887
0.9429	High Similarity	NPC7870
0.9429	High Similarity	NPC475296
0.9429	High Similarity	NPC476885
0.9429	High Similarity	NPC59804
0.9429	High Similarity	NPC90856
0.9429	High Similarity	NPC174679
0.9429	High Similarity	NPC279554
0.9417	High Similarity	NPC475611
0.9364	High Similarity	NPC294112
0.9352	High Similarity	NPC26626
0.9352	High Similarity	NPC305267
0.9352	High Similarity	NPC291903
0.9352	High Similarity	NPC288205
0.9352	High Similarity	NPC51465
0.9352	High Similarity	NPC37134
0.9352	High Similarity	NPC75287
0.9352	High Similarity	NPC476992
0.934	High Similarity	NPC179434
0.934	High Similarity	NPC473481
0.934	High Similarity	NPC30397
0.934	High Similarity	NPC211798
0.934	High Similarity	NPC191763
0.934	High Similarity	NPC108748
0.934	High Similarity	NPC235841
0.934	High Similarity	NPC164419
0.934	High Similarity	NPC297208
0.9333	High Similarity	NPC137917
0.9279	High Similarity	NPC31193
0.9279	High Similarity	NPC242840
0.9266	High Similarity	NPC475209
0.9266	High Similarity	NPC69811
0.9266	High Similarity	NPC191827
0.9266	High Similarity	NPC475119
0.9266	High Similarity	NPC473452
0.9266	High Similarity	NPC8524
0.9266	High Similarity	NPC104137
0.9266	High Similarity	NPC300419
0.9266	High Similarity	NPC473824
0.9266	High Similarity	NPC102505
0.9266	High Similarity	NPC123522
0.9266	High Similarity	NPC220160
0.9266	High Similarity	NPC470876
0.9266	High Similarity	NPC286457
0.9266	High Similarity	NPC33012
0.9266	High Similarity	NPC85154
0.9266	High Similarity	NPC309223
0.9266	High Similarity	NPC475514
0.9252	High Similarity	NPC139044
0.9252	High Similarity	NPC102439
0.9252	High Similarity	NPC256798
0.9252	High Similarity	NPC257468
0.9252	High Similarity	NPC473383
0.9252	High Similarity	NPC104400
0.9252	High Similarity	NPC109079
0.9252	High Similarity	NPC471383
0.9252	High Similarity	NPC10320
0.9252	High Similarity	NPC46388
0.9252	High Similarity	NPC116794
0.9252	High Similarity	NPC128925
0.9252	High Similarity	NPC276093
0.9252	High Similarity	NPC79718
0.9252	High Similarity	NPC139894
0.9252	High Similarity	NPC471967
0.9252	High Similarity	NPC473373
0.9252	High Similarity	NPC37739
0.9252	High Similarity	NPC475516
0.9252	High Similarity	NPC101744
0.9252	High Similarity	NPC324875
0.9252	High Similarity	NPC292677
0.9252	High Similarity	NPC104071
0.9252	High Similarity	NPC475504
0.9252	High Similarity	NPC469946
0.9245	High Similarity	NPC269095
0.9245	High Similarity	NPC78046
0.9245	High Similarity	NPC220984
0.9182	High Similarity	NPC232237
0.9182	High Similarity	NPC105800
0.9182	High Similarity	NPC237191
0.9182	High Similarity	NPC286347
0.9167	High Similarity	NPC258885
0.9167	High Similarity	NPC133818
0.9167	High Similarity	NPC47063
0.9167	High Similarity	NPC138334
0.9167	High Similarity	NPC46665
0.9167	High Similarity	NPC114287
0.9167	High Similarity	NPC151543
0.9167	High Similarity	NPC271138
0.9167	High Similarity	NPC192600
0.9167	High Similarity	NPC475287
0.9167	High Similarity	NPC174720
0.9167	High Similarity	NPC251263
0.9167	High Similarity	NPC204458
0.9167	High Similarity	NPC150400
0.9167	High Similarity	NPC241909
0.9167	High Similarity	NPC124296
0.9167	High Similarity	NPC269315
0.9167	High Similarity	NPC134835
0.9167	High Similarity	NPC473826
0.9167	High Similarity	NPC114304
0.9167	High Similarity	NPC166422
0.9167	High Similarity	NPC219180
0.9167	High Similarity	NPC323341
0.9167	High Similarity	NPC96641
0.9167	High Similarity	NPC73318
0.9167	High Similarity	NPC163183
0.9167	High Similarity	NPC189884
0.9167	High Similarity	NPC155410
0.9167	High Similarity	NPC309714
0.9167	High Similarity	NPC473343
0.9167	High Similarity	NPC295823
0.9167	High Similarity	NPC475467
0.9115	High Similarity	NPC2370
0.9115	High Similarity	NPC44716
0.9099	High Similarity	NPC214484
0.9099	High Similarity	NPC475171
0.9099	High Similarity	NPC25663
0.9099	High Similarity	NPC114441
0.9099	High Similarity	NPC35405
0.9099	High Similarity	NPC51564
0.9099	High Similarity	NPC471577
0.9099	High Similarity	NPC11551
0.9099	High Similarity	NPC207738
0.9099	High Similarity	NPC39211
0.9099	High Similarity	NPC472949
0.9099	High Similarity	NPC180550
0.9099	High Similarity	NPC473884
0.9099	High Similarity	NPC309780
0.9099	High Similarity	NPC135849
0.9099	High Similarity	NPC208381
0.9099	High Similarity	NPC6377
0.9099	High Similarity	NPC469945
0.9099	High Similarity	NPC157868
0.9091	High Similarity	NPC224121
0.9091	High Similarity	NPC471580
0.9083	High Similarity	NPC475140
0.9083	High Similarity	NPC119592
0.9083	High Similarity	NPC309907
0.9083	High Similarity	NPC4328
0.9083	High Similarity	NPC305981
0.9083	High Similarity	NPC224381
0.9083	High Similarity	NPC161717
0.9083	High Similarity	NPC79643
0.9083	High Similarity	NPC476068
0.9083	High Similarity	NPC60557
0.9083	High Similarity	NPC294453
0.9083	High Similarity	NPC204414
0.9083	High Similarity	NPC473714
0.9083	High Similarity	NPC250247
0.9083	High Similarity	NPC43550
0.9083	High Similarity	NPC475633
0.9083	High Similarity	NPC71065
0.9083	High Similarity	NPC293330
0.9083	High Similarity	NPC67857
0.9083	High Similarity	NPC54636
0.9083	High Similarity	NPC471385

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 NPC100383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	2108
0.2-0.3	3869
0.3-0.4	1924
0.4-0.5	595
0.5-0.6	264
0.6-0.7	111
0.7-0.8	29
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8783	High Similarity	NPD8328	Phase 3
0.875	High Similarity	NPD8295	Clinical (unspecified phase)
0.8624	High Similarity	NPD8132	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD7319	Approved
0.8017	Intermediate Similarity	NPD7507	Approved
0.8	Intermediate Similarity	NPD8133	Approved
0.7946	Intermediate Similarity	NPD6412	Phase 2
0.7925	Intermediate Similarity	NPD7748	Approved
0.7876	Intermediate Similarity	NPD6686	Approved
0.787	Intermediate Similarity	NPD7902	Approved
0.7742	Intermediate Similarity	NPD7736	Approved
0.7736	Intermediate Similarity	NPD7515	Phase 2
0.7603	Intermediate Similarity	NPD8294	Approved
0.7603	Intermediate Similarity	NPD8377	Approved
0.7593	Intermediate Similarity	NPD7900	Approved
0.7593	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8296	Approved
0.7541	Intermediate Similarity	NPD8380	Approved
0.7541	Intermediate Similarity	NPD8517	Approved
0.7541	Intermediate Similarity	NPD8515	Approved
0.7541	Intermediate Similarity	NPD8378	Approved
0.7541	Intermediate Similarity	NPD8379	Approved
0.7541	Intermediate Similarity	NPD8516	Approved
0.7541	Intermediate Similarity	NPD8513	Phase 3
0.7541	Intermediate Similarity	NPD8033	Approved
0.7541	Intermediate Similarity	NPD8335	Approved
0.752	Intermediate Similarity	NPD8293	Discontinued
0.7438	Intermediate Similarity	NPD7327	Approved
0.7438	Intermediate Similarity	NPD7328	Approved
0.7377	Intermediate Similarity	NPD7516	Approved
0.7339	Intermediate Similarity	NPD6370	Approved
0.7258	Intermediate Similarity	NPD7503	Approved
0.7248	Intermediate Similarity	NPD8035	Phase 2
0.7248	Intermediate Similarity	NPD8034	Phase 2
0.7222	Intermediate Similarity	NPD7492	Approved
0.7177	Intermediate Similarity	NPD6319	Approved
0.7177	Intermediate Similarity	NPD6059	Approved
0.7177	Intermediate Similarity	NPD6054	Approved
0.7167	Intermediate Similarity	NPD6882	Approved
0.7167	Intermediate Similarity	NPD8297	Approved
0.7165	Intermediate Similarity	NPD6616	Approved
0.7119	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7078	Approved
0.7091	Intermediate Similarity	NPD6411	Approved
0.7087	Intermediate Similarity	NPD7645	Phase 2
0.7073	Intermediate Similarity	NPD7115	Discovery
0.7027	Intermediate Similarity	NPD6399	Phase 3
0.7018	Intermediate Similarity	NPD7638	Approved
0.7009	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6015	Approved
0.6984	Remote Similarity	NPD6016	Approved
0.6957	Remote Similarity	NPD7639	Approved
0.6957	Remote Similarity	NPD7640	Approved
0.6949	Remote Similarity	NPD6402	Approved
0.6949	Remote Similarity	NPD5739	Approved
0.6949	Remote Similarity	NPD6675	Approved
0.6949	Remote Similarity	NPD7128	Approved
0.6935	Remote Similarity	NPD6009	Approved
0.6929	Remote Similarity	NPD5988	Approved
0.6917	Remote Similarity	NPD6373	Approved
0.6917	Remote Similarity	NPD6372	Approved
0.6917	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6101	Approved
0.6875	Remote Similarity	NPD6067	Discontinued
0.687	Remote Similarity	NPD4225	Approved
0.6833	Remote Similarity	NPD6899	Approved
0.6833	Remote Similarity	NPD7320	Approved
0.6833	Remote Similarity	NPD6881	Approved
0.6829	Remote Similarity	NPD4632	Approved
0.6803	Remote Similarity	NPD6649	Approved
0.6803	Remote Similarity	NPD8130	Phase 1
0.6803	Remote Similarity	NPD6650	Approved
0.6803	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5697	Approved
0.675	Remote Similarity	NPD5701	Approved
0.6721	Remote Similarity	NPD7290	Approved
0.6721	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6883	Approved
0.6721	Remote Similarity	NPD7102	Approved
0.6718	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD6012	Approved
0.6639	Remote Similarity	NPD6013	Approved
0.6639	Remote Similarity	NPD6014	Approved
0.6638	Remote Similarity	NPD6084	Phase 2
0.6638	Remote Similarity	NPD6083	Phase 2
0.6637	Remote Similarity	NPD7983	Approved
0.6636	Remote Similarity	NPD3618	Phase 1
0.6607	Remote Similarity	NPD5328	Approved
0.6606	Remote Similarity	NPD4786	Approved
0.6589	Remote Similarity	NPD6921	Approved
0.6585	Remote Similarity	NPD4634	Approved
0.6579	Remote Similarity	NPD5778	Approved
0.6579	Remote Similarity	NPD5779	Approved
0.6579	Remote Similarity	NPD8171	Discontinued
0.6577	Remote Similarity	NPD3573	Approved
0.6574	Remote Similarity	NPD3667	Approved
0.6557	Remote Similarity	NPD6011	Approved
0.6552	Remote Similarity	NPD4697	Phase 3
0.6549	Remote Similarity	NPD46	Approved
0.6549	Remote Similarity	NPD6698	Approved
0.6532	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4755	Approved
0.6491	Remote Similarity	NPD6079	Approved
0.6489	Remote Similarity	NPD7604	Phase 2
0.6486	Remote Similarity	NPD6409	Approved
0.6486	Remote Similarity	NPD7334	Approved
0.6486	Remote Similarity	NPD7521	Approved
0.6486	Remote Similarity	NPD5330	Approved
0.6486	Remote Similarity	NPD6684	Approved
0.6486	Remote Similarity	NPD7146	Approved
0.6475	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5983	Phase 2
0.646	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD8299	Approved
0.6439	Remote Similarity	NPD8342	Approved
0.6439	Remote Similarity	NPD8340	Approved
0.6439	Remote Similarity	NPD8341	Approved
0.6435	Remote Similarity	NPD4202	Approved
0.6417	Remote Similarity	NPD7632	Discontinued
0.6393	Remote Similarity	NPD6008	Approved
0.6391	Remote Similarity	NPD8451	Approved
0.6391	Remote Similarity	NPD6336	Discontinued
0.6389	Remote Similarity	NPD7525	Registered
0.6387	Remote Similarity	NPD4700	Approved
0.6387	Remote Similarity	NPD4696	Approved
0.6387	Remote Similarity	NPD5286	Approved
0.6387	Remote Similarity	NPD5285	Approved
0.6372	Remote Similarity	NPD6672	Approved
0.6372	Remote Similarity	NPD6903	Approved
0.6372	Remote Similarity	NPD5737	Approved
0.6343	Remote Similarity	NPD8448	Approved
0.6328	Remote Similarity	NPD6940	Discontinued
0.6328	Remote Similarity	NPD6274	Approved
0.6325	Remote Similarity	NPD5695	Phase 3
0.6324	Remote Similarity	NPD8392	Approved
0.6324	Remote Similarity	NPD8390	Approved
0.6324	Remote Similarity	NPD8391	Approved
0.6308	Remote Similarity	NPD7101	Approved
0.6308	Remote Similarity	NPD7100	Approved
0.6306	Remote Similarity	NPD3666	Approved
0.6306	Remote Similarity	NPD3665	Phase 1
0.6306	Remote Similarity	NPD3133	Approved
0.6303	Remote Similarity	NPD5696	Approved
0.6296	Remote Similarity	NPD8336	Approved
0.6296	Remote Similarity	NPD8337	Approved
0.6281	Remote Similarity	NPD5225	Approved
0.6281	Remote Similarity	NPD5226	Approved
0.6281	Remote Similarity	NPD4633	Approved
0.6281	Remote Similarity	NPD5211	Phase 2
0.6281	Remote Similarity	NPD5224	Approved
0.6279	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7839	Suspended
0.6271	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5221	Approved
0.6271	Remote Similarity	NPD5222	Approved
0.6262	Remote Similarity	NPD6116	Phase 1
0.626	Remote Similarity	NPD4767	Approved
0.626	Remote Similarity	NPD4768	Approved
0.6232	Remote Similarity	NPD8338	Approved
0.6232	Remote Similarity	NPD8449	Approved
0.6231	Remote Similarity	NPD7641	Discontinued
0.6231	Remote Similarity	NPD6335	Approved
0.623	Remote Similarity	NPD5174	Approved
0.623	Remote Similarity	NPD5175	Approved
0.6218	Remote Similarity	NPD5173	Approved
0.6216	Remote Similarity	NPD3669	Approved
0.6216	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6909	Approved
0.6212	Remote Similarity	NPD6908	Approved
0.6207	Remote Similarity	NPD7637	Suspended
0.6204	Remote Similarity	NPD5956	Approved
0.6204	Remote Similarity	NPD6118	Approved
0.6204	Remote Similarity	NPD6115	Approved
0.6204	Remote Similarity	NPD6114	Approved
0.6204	Remote Similarity	NPD6697	Approved
0.6202	Remote Similarity	NPD6868	Approved
0.6198	Remote Similarity	NPD5223	Approved
0.6195	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD8450	Suspended
0.6186	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5141	Approved
0.6174	Remote Similarity	NPD4753	Phase 2
0.6168	Remote Similarity	NPD6117	Approved
0.6167	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD3668	Phase 3
0.616	Remote Similarity	NPD4729	Approved
0.616	Remote Similarity	NPD4730	Approved
0.6154	Remote Similarity	NPD6317	Approved
0.6134	Remote Similarity	NPD7614	Phase 1
0.6134	Remote Similarity	NPD7732	Phase 3
0.6122	Remote Similarity	NPD7625	Phase 1
0.6119	Remote Similarity	NPD7830	Approved
0.6119	Remote Similarity	NPD7122	Discontinued

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