NPASS Compound

Structure

NPC476123 OpenBabel07101718242D 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 3 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 4 32 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 1 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 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:	604.4
Volume:	627.626
LogP:	4.181
LogD:	3.856
LogS:	-3.912
# Rotatable Bonds:	4
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.231
Synthetic Accessibility Score:	5.269
Fsp3:	0.914
Lipinski Rule-of-5:	Accepted
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:	-5.425
MDCK Permeability:	1.156985126726795e-05
Pgp-inhibitor:	0.15
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.189

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	90.28629302978516%
Volume Distribution (VD):	0.531
Pgp-substrate:	6.190906524658203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.691
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.159
CYP3A4-substrate:	0.09

ADMET: Excretion

Clearance (CL):	1.036
Half-life (T1/2):	0.214

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.413
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.083
Carcinogencity:	0.189
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC476123

Natural Product ID:	NPC476123
*Common Name:**	3Beta-[(Alpha-L-Arabinopyranosyl)Oxy]-23-Hydroxyolean-12-En-28-Oic Acid
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-9-(hydroxymethyl)-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:	QUBNLZCADIYAFW-DRHKFHIJSA-N
Standard InCHI:	InChI=1S/C35H56O8/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/h7,21-28,36-39H,8-19H2,1-6H3,(H,40,41)/t21-,22-,23+,24+,25-,26-,27+,28-,31-,32?,33+,34+,35-/m0/s1
SMILES:	OCC1(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:	CHEMBL538200
PubChem CID:	25087737
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	=	12.5	ug.mL-1	PMID[567192]

☑ 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 NPC476123 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	255
0.1-0.2	1683
0.2-0.3	5021
0.3-0.4	12217
0.4-0.5	10213
0.5-0.6	5958
0.6-0.7	4152
0.7-0.8	1948
0.8-0.85	649
0.85-0.9	243
0.9-0.95	133
0.95-1	225

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC177246
1.0	High Similarity	NPC284807
1.0	High Similarity	NPC28198
0.99	High Similarity	NPC237503
0.99	High Similarity	NPC204407
0.99	High Similarity	NPC127853
0.99	High Similarity	NPC57362
0.99	High Similarity	NPC167383
0.99	High Similarity	NPC306746
0.9899	High Similarity	NPC283849
0.9899	High Similarity	NPC473538
0.9802	High Similarity	NPC174679
0.9802	High Similarity	NPC279554
0.9802	High Similarity	NPC102914
0.9802	High Similarity	NPC274507
0.9802	High Similarity	NPC476887
0.9802	High Similarity	NPC75747
0.9802	High Similarity	NPC90856
0.9802	High Similarity	NPC474589
0.9802	High Similarity	NPC59804
0.9802	High Similarity	NPC270667
0.9802	High Similarity	NPC242611
0.9802	High Similarity	NPC68419
0.9802	High Similarity	NPC199457
0.9802	High Similarity	NPC127056
0.9802	High Similarity	NPC475296
0.9802	High Similarity	NPC108709
0.9802	High Similarity	NPC136877
0.9802	High Similarity	NPC7870
0.9802	High Similarity	NPC476880
0.9802	High Similarity	NPC476882
0.9802	High Similarity	NPC476886
0.9802	High Similarity	NPC476881
0.9802	High Similarity	NPC29069
0.9802	High Similarity	NPC56713
0.9802	High Similarity	NPC476885
0.9802	High Similarity	NPC476883
0.9802	High Similarity	NPC476884
0.9802	High Similarity	NPC110139
0.9802	High Similarity	NPC164194
0.9798	High Similarity	NPC475611
0.9706	High Similarity	NPC179434
0.9706	High Similarity	NPC297208
0.9706	High Similarity	NPC164419
0.9706	High Similarity	NPC211798
0.9706	High Similarity	NPC191763
0.9706	High Similarity	NPC31839
0.9706	High Similarity	NPC235841
0.9706	High Similarity	NPC108748
0.9706	High Similarity	NPC473481
0.9706	High Similarity	NPC30397
0.9703	High Similarity	NPC137917
0.9612	High Similarity	NPC80843
0.9612	High Similarity	NPC1046
0.9612	High Similarity	NPC10320
0.9612	High Similarity	NPC46388
0.9612	High Similarity	NPC102439
0.9612	High Similarity	NPC128925
0.9612	High Similarity	NPC257468
0.9612	High Similarity	NPC48249
0.9612	High Similarity	NPC469946
0.9612	High Similarity	NPC139894
0.9612	High Similarity	NPC475516
0.9612	High Similarity	NPC100383
0.9612	High Similarity	NPC471383
0.9612	High Similarity	NPC104400
0.9612	High Similarity	NPC37739
0.9612	High Similarity	NPC104071
0.9612	High Similarity	NPC116794
0.9612	High Similarity	NPC324875
0.9612	High Similarity	NPC109079
0.9612	High Similarity	NPC101744
0.9612	High Similarity	NPC276093
0.9612	High Similarity	NPC292677
0.9612	High Similarity	NPC79718
0.9612	High Similarity	NPC139044
0.9612	High Similarity	NPC471967
0.9612	High Similarity	NPC256798
0.9612	High Similarity	NPC475504
0.9612	High Similarity	NPC473383
0.9612	High Similarity	NPC473373
0.9608	High Similarity	NPC78046
0.9608	High Similarity	NPC220984
0.9608	High Similarity	NPC269095
0.9519	High Similarity	NPC73318
0.9519	High Similarity	NPC271138
0.9519	High Similarity	NPC189884
0.9519	High Similarity	NPC309714
0.9519	High Similarity	NPC241909
0.9519	High Similarity	NPC134835
0.9519	High Similarity	NPC204458
0.9519	High Similarity	NPC138334
0.9519	High Similarity	NPC114304
0.9519	High Similarity	NPC46665
0.9519	High Similarity	NPC475287
0.9519	High Similarity	NPC473343
0.9519	High Similarity	NPC475467
0.9519	High Similarity	NPC47063
0.9519	High Similarity	NPC251263
0.9519	High Similarity	NPC219180
0.9519	High Similarity	NPC258885
0.9519	High Similarity	NPC133818
0.9519	High Similarity	NPC114287
0.9519	High Similarity	NPC151543
0.9519	High Similarity	NPC192600
0.9519	High Similarity	NPC323341
0.9519	High Similarity	NPC475208
0.9519	High Similarity	NPC150400
0.9519	High Similarity	NPC96641
0.9519	High Similarity	NPC155410
0.9519	High Similarity	NPC124296
0.9519	High Similarity	NPC174720
0.9519	High Similarity	NPC166422
0.9519	High Similarity	NPC295823
0.9519	High Similarity	NPC163183
0.9519	High Similarity	NPC238935
0.9519	High Similarity	NPC269315
0.9519	High Similarity	NPC473826
0.9429	High Similarity	NPC54636
0.9429	High Similarity	NPC71065
0.9429	High Similarity	NPC261506
0.9429	High Similarity	NPC57484
0.9429	High Similarity	NPC475140
0.9429	High Similarity	NPC475160
0.9429	High Similarity	NPC294453
0.9429	High Similarity	NPC60557
0.9429	High Similarity	NPC70809
0.9429	High Similarity	NPC65105
0.9429	High Similarity	NPC293330
0.9429	High Similarity	NPC471385
0.9429	High Similarity	NPC204414
0.9429	High Similarity	NPC76972
0.9429	High Similarity	NPC100639
0.9429	High Similarity	NPC298034
0.9429	High Similarity	NPC202828
0.9429	High Similarity	NPC224381
0.9429	High Similarity	NPC305981
0.9429	High Similarity	NPC309907
0.9429	High Similarity	NPC227551
0.9429	High Similarity	NPC119592
0.9429	High Similarity	NPC41061
0.9429	High Similarity	NPC4328
0.9429	High Similarity	NPC236638
0.9429	High Similarity	NPC43550
0.9429	High Similarity	NPC161717
0.9429	High Similarity	NPC250247
0.9429	High Similarity	NPC471550
0.9429	High Similarity	NPC475633
0.9429	High Similarity	NPC469782
0.9429	High Similarity	NPC67857
0.9429	High Similarity	NPC476068
0.9429	High Similarity	NPC123199
0.9429	High Similarity	NPC79643
0.9429	High Similarity	NPC473714
0.9429	High Similarity	NPC475486
0.9429	High Similarity	NPC164389
0.9412	High Similarity	NPC285576
0.934	High Similarity	NPC291903
0.934	High Similarity	NPC51465
0.934	High Similarity	NPC58448
0.934	High Similarity	NPC26626
0.934	High Similarity	NPC160415
0.934	High Similarity	NPC476992
0.934	High Similarity	NPC75287
0.934	High Similarity	NPC161674
0.934	High Similarity	NPC37134
0.934	High Similarity	NPC471384
0.934	High Similarity	NPC305267
0.934	High Similarity	NPC288205
0.9327	High Similarity	NPC190837
0.9307	High Similarity	NPC173583
0.9252	High Similarity	NPC110633
0.9252	High Similarity	NPC471547
0.9252	High Similarity	NPC220160
0.9252	High Similarity	NPC323359
0.9252	High Similarity	NPC470876
0.9252	High Similarity	NPC473405
0.9252	High Similarity	NPC286457
0.9252	High Similarity	NPC85154
0.9252	High Similarity	NPC309223
0.9252	High Similarity	NPC33012
0.9252	High Similarity	NPC475514
0.9252	High Similarity	NPC68175
0.9252	High Similarity	NPC475209
0.9252	High Similarity	NPC191827
0.9252	High Similarity	NPC69811
0.9252	High Similarity	NPC475119
0.9252	High Similarity	NPC473452
0.9252	High Similarity	NPC8524
0.9252	High Similarity	NPC148417
0.9252	High Similarity	NPC123522
0.9252	High Similarity	NPC104137
0.9252	High Similarity	NPC185466
0.9252	High Similarity	NPC300419
0.9252	High Similarity	NPC102505
0.9252	High Similarity	NPC136768
0.9252	High Similarity	NPC473824
0.9238	High Similarity	NPC212968
0.9238	High Similarity	NPC65590
0.9238	High Similarity	NPC64106

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 NPC476123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	1978
0.2-0.3	3878
0.3-0.4	2013
0.4-0.5	594
0.5-0.6	273
0.6-0.7	146
0.7-0.8	26
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8952	High Similarity	NPD8132	Clinical (unspecified phase)
0.8761	High Similarity	NPD8328	Phase 3
0.8727	High Similarity	NPD8295	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD8133	Approved
0.8241	Intermediate Similarity	NPD6412	Phase 2
0.8235	Intermediate Similarity	NPD7748	Approved
0.8173	Intermediate Similarity	NPD7902	Approved
0.8165	Intermediate Similarity	NPD6686	Approved
0.8039	Intermediate Similarity	NPD7515	Phase 2
0.7983	Intermediate Similarity	NPD7507	Approved
0.7885	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7900	Approved
0.7863	Intermediate Similarity	NPD8377	Approved
0.7863	Intermediate Similarity	NPD8294	Approved
0.7797	Intermediate Similarity	NPD8033	Approved
0.7797	Intermediate Similarity	NPD8380	Approved
0.7797	Intermediate Similarity	NPD8296	Approved
0.7797	Intermediate Similarity	NPD8378	Approved
0.7797	Intermediate Similarity	NPD8379	Approved
0.7797	Intermediate Similarity	NPD8335	Approved
0.7787	Intermediate Similarity	NPD7319	Approved
0.7705	Intermediate Similarity	NPD7736	Approved
0.7692	Intermediate Similarity	NPD7327	Approved
0.7692	Intermediate Similarity	NPD7328	Approved
0.7627	Intermediate Similarity	NPD7516	Approved
0.7524	Intermediate Similarity	NPD8034	Phase 2
0.7524	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD8513	Phase 3
0.75	Intermediate Similarity	NPD8516	Approved
0.75	Intermediate Similarity	NPD8515	Approved
0.75	Intermediate Similarity	NPD8517	Approved
0.748	Intermediate Similarity	NPD8293	Discontinued
0.7414	Intermediate Similarity	NPD6882	Approved
0.7414	Intermediate Similarity	NPD8297	Approved
0.7374	Intermediate Similarity	NPD7645	Phase 2
0.7295	Intermediate Similarity	NPD6370	Approved
0.729	Intermediate Similarity	NPD6399	Phase 3
0.7282	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7638	Approved
0.7257	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7640	Approved
0.7207	Intermediate Similarity	NPD7639	Approved
0.7193	Intermediate Similarity	NPD6675	Approved
0.7193	Intermediate Similarity	NPD6402	Approved
0.7193	Intermediate Similarity	NPD5739	Approved
0.7193	Intermediate Similarity	NPD7128	Approved
0.7177	Intermediate Similarity	NPD7492	Approved
0.7167	Intermediate Similarity	NPD6009	Approved
0.7155	Intermediate Similarity	NPD6373	Approved
0.7155	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6372	Approved
0.7131	Intermediate Similarity	NPD6319	Approved
0.7131	Intermediate Similarity	NPD6059	Approved
0.7131	Intermediate Similarity	NPD6054	Approved
0.712	Intermediate Similarity	NPD6616	Approved
0.7097	Intermediate Similarity	NPD6067	Discontinued
0.7069	Intermediate Similarity	NPD6881	Approved
0.7069	Intermediate Similarity	NPD7320	Approved
0.7069	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6899	Approved
0.7063	Intermediate Similarity	NPD7078	Approved
0.7059	Intermediate Similarity	NPD4632	Approved
0.7037	Intermediate Similarity	NPD6411	Approved
0.7034	Intermediate Similarity	NPD6650	Approved
0.7034	Intermediate Similarity	NPD8130	Phase 1
0.7034	Intermediate Similarity	NPD6649	Approved
0.7034	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7115	Discovery
0.6983	Remote Similarity	NPD5697	Approved
0.6983	Remote Similarity	NPD5701	Approved
0.6949	Remote Similarity	NPD7290	Approved
0.6949	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7102	Approved
0.6949	Remote Similarity	NPD6883	Approved
0.6935	Remote Similarity	NPD6016	Approved
0.6935	Remote Similarity	NPD6015	Approved
0.6916	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6617	Approved
0.6891	Remote Similarity	NPD6847	Approved
0.6891	Remote Similarity	NPD6869	Approved
0.6887	Remote Similarity	NPD3618	Phase 1
0.688	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD6084	Phase 2
0.6875	Remote Similarity	NPD6083	Phase 2
0.6864	Remote Similarity	NPD6013	Approved
0.6864	Remote Similarity	NPD6014	Approved
0.6864	Remote Similarity	NPD6012	Approved
0.6857	Remote Similarity	NPD4786	Approved
0.6852	Remote Similarity	NPD6101	Approved
0.6852	Remote Similarity	NPD5328	Approved
0.6852	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD3667	Approved
0.6822	Remote Similarity	NPD3573	Approved
0.6818	Remote Similarity	NPD8171	Discontinued
0.6814	Remote Similarity	NPD4225	Approved
0.6789	Remote Similarity	NPD46	Approved
0.6789	Remote Similarity	NPD6698	Approved
0.678	Remote Similarity	NPD6011	Approved
0.675	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6684	Approved
0.6729	Remote Similarity	NPD7334	Approved
0.6729	Remote Similarity	NPD6409	Approved
0.6729	Remote Similarity	NPD7521	Approved
0.6729	Remote Similarity	NPD7146	Approved
0.6729	Remote Similarity	NPD5330	Approved
0.6727	Remote Similarity	NPD6079	Approved
0.6726	Remote Similarity	NPD4755	Approved
0.6697	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD5983	Phase 2
0.6638	Remote Similarity	NPD7632	Discontinued
0.6635	Remote Similarity	NPD7525	Registered
0.6615	Remote Similarity	NPD6033	Approved
0.661	Remote Similarity	NPD6008	Approved
0.6609	Remote Similarity	NPD5286	Approved
0.6609	Remote Similarity	NPD4700	Approved
0.6609	Remote Similarity	NPD5285	Approved
0.6609	Remote Similarity	NPD4696	Approved
0.6606	Remote Similarity	NPD6672	Approved
0.6606	Remote Similarity	NPD6903	Approved
0.6606	Remote Similarity	NPD5737	Approved
0.6589	Remote Similarity	NPD6336	Discontinued
0.6577	Remote Similarity	NPD7983	Approved
0.6549	Remote Similarity	NPD5695	Phase 3
0.6542	Remote Similarity	NPD3665	Phase 1
0.6542	Remote Similarity	NPD3133	Approved
0.6542	Remote Similarity	NPD3666	Approved
0.6535	Remote Similarity	NPD6921	Approved
0.6532	Remote Similarity	NPD6940	Discontinued
0.6532	Remote Similarity	NPD6274	Approved
0.6529	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD5696	Approved
0.6518	Remote Similarity	NPD5779	Approved
0.6518	Remote Similarity	NPD5778	Approved
0.6508	Remote Similarity	NPD7100	Approved
0.6508	Remote Similarity	NPD7101	Approved
0.6505	Remote Similarity	NPD6116	Phase 1
0.6496	Remote Similarity	NPD5226	Approved
0.6496	Remote Similarity	NPD5211	Phase 2
0.6496	Remote Similarity	NPD5225	Approved
0.6496	Remote Similarity	NPD5224	Approved
0.6496	Remote Similarity	NPD4633	Approved
0.6491	Remote Similarity	NPD4697	Phase 3
0.6491	Remote Similarity	NPD5222	Approved
0.6491	Remote Similarity	NPD5221	Approved
0.6491	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4767	Approved
0.6471	Remote Similarity	NPD4768	Approved
0.6449	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD3669	Approved
0.6442	Remote Similarity	NPD6697	Approved
0.6442	Remote Similarity	NPD6114	Approved
0.6442	Remote Similarity	NPD6118	Approved
0.6442	Remote Similarity	NPD6115	Approved
0.6441	Remote Similarity	NPD5174	Approved
0.6441	Remote Similarity	NPD5175	Approved
0.6435	Remote Similarity	NPD5173	Approved
0.6429	Remote Similarity	NPD6335	Approved
0.6418	Remote Similarity	NPD8449	Approved
0.641	Remote Similarity	NPD5223	Approved
0.6408	Remote Similarity	NPD6117	Approved
0.6406	Remote Similarity	NPD6909	Approved
0.6406	Remote Similarity	NPD6908	Approved
0.6404	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6868	Approved
0.6396	Remote Similarity	NPD4753	Phase 2
0.6389	Remote Similarity	NPD3668	Phase 3
0.6387	Remote Similarity	NPD5141	Approved
0.6379	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.637	Remote Similarity	NPD8450	Suspended
0.6364	Remote Similarity	NPD4729	Approved
0.6364	Remote Similarity	NPD4730	Approved
0.6349	Remote Similarity	NPD6317	Approved
0.6348	Remote Similarity	NPD7732	Phase 3
0.6348	Remote Similarity	NPD7614	Phase 1
0.6303	Remote Similarity	NPD4754	Approved
0.6299	Remote Similarity	NPD6314	Approved
0.6299	Remote Similarity	NPD6313	Approved
0.6294	Remote Similarity	NPD7625	Phase 1
0.6273	Remote Similarity	NPD6098	Approved
0.6271	Remote Similarity	NPD5344	Discontinued
0.6262	Remote Similarity	NPD1780	Approved
0.6262	Remote Similarity	NPD1779	Approved
0.626	Remote Similarity	NPD5251	Approved
0.626	Remote Similarity	NPD5247	Approved
0.626	Remote Similarity	NPD5248	Approved
0.626	Remote Similarity	NPD5250	Approved
0.626	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD6673	Approved
0.625	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD6080	Approved
0.6241	Remote Similarity	NPD8336	Approved
0.6241	Remote Similarity	NPD8337	Approved
0.623	Remote Similarity	NPD5128	Approved
0.622	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6113	Clinical (unspecified phase)

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