NPASS Compound

Structure

NPC244356 OpenBabel07101718282D 36 40 0 0 1 0 0 0 0 0999 V2000 3.8734 1.4322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2663 1.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3552 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8674 1.1063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1911 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6177 -1.2771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9191 1.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6177 0.3015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3796 2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2930 -1.8669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 1.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 2 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 -3.3796 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 3.4146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3227 -1.9689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8664 -2.6562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 2 16 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 27 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 19 1 0 0 0 0 15 28 1 0 0 0 0 17 16 1 6 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 18 30 1 6 0 0 0 19 23 1 0 0 0 0 19 31 1 1 0 0 0 20 27 1 1 0 0 0 20 28 1 0 0 0 0 21 26 1 0 0 0 0 21 32 2 0 0 0 0 22 29 1 1 0 0 0 23 26 1 0 0 0 0 23 27 1 1 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 27 5 1 1 0 0 0 28 30 1 6 0 0 0 29 24 1 1 0 0 0 30 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.31
Volume:	526.849
LogP:	3.507
LogD:	3.236
LogS:	-3.404
# Rotatable Bonds:	3
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	5.084
Fsp3:	0.833
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:	-5.928
MDCK Permeability:	6.032396868249634e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.374
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	78.36626434326172%
Volume Distribution (VD):	0.472
Pgp-substrate:	12.270586967468262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.675
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	1.104
Half-life (T1/2):	0.797

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.328
Skin Sensitization:	0.033
Carcinogencity:	0.036
Eye Corrosion:	0.023
Eye Irritation:	0.093
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC244356

Natural Product ID:	NPC244356
*Common Name:**	6Beta-Hydroxylup-20(29)-En-3-Oxo-27,28-Dioic Acid
IUPAC Name:	(1R,3aS,5aS,5bR,7R,7aR,11aR,11bR,13aR,13bR)-7-hydroxy-5b,8,8,11a-tetramethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a,5a-dicarboxylic acid
Synonyms:
Standard InCHIKey:	BLMDUACVPBWIGN-WHXPFMOASA-N
Standard InCHI:	InChI=1S/C30H44O6/c1-16(2)17-9-12-29(24(33)34)13-14-30(25(35)36)18(22(17)29)7-8-20-27(5)11-10-21(32)26(3,4)23(27)19(31)15-28(20,30)6/h17-20,22-23,31H,1,7-15H2,2-6H3,(H,33,34)(H,35,36)/t17-,18+,19+,20+,22+,23-,27+,28+,29-,30+/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(CC[C@@]3([C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5[C@@H](C[C@@]34C)O)[C@@H]12)C(=O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509225
PubChem CID:	12040949
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
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141874]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	leaves and flowers	n.a.	n.a.	PMID[14738390]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4162	Cell Line	NUGC	Homo sapiens	Activity	=	20.0	%	PMID[505592]

☑ 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 NPC244356 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	212
0.1-0.2	1751
0.2-0.3	6326
0.3-0.4	14654
0.4-0.5	6968
0.5-0.6	5184
0.6-0.7	4498
0.7-0.8	2614
0.8-0.85	380
0.85-0.9	80
0.9-0.95	27
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC224060
0.9535	High Similarity	NPC474719
0.9302	High Similarity	NPC2783
0.9195	High Similarity	NPC33768
0.9195	High Similarity	NPC269360
0.9195	High Similarity	NPC264005
0.9186	High Similarity	NPC264317
0.9186	High Similarity	NPC294438
0.9121	High Similarity	NPC98639
0.9111	High Similarity	NPC291373
0.9091	High Similarity	NPC16377
0.908	High Similarity	NPC12774
0.907	High Similarity	NPC475745
0.907	High Similarity	NPC474482
0.9022	High Similarity	NPC200054
0.9022	High Similarity	NPC29410
0.9011	High Similarity	NPC303863
0.9011	High Similarity	NPC277399
0.9	High Similarity	NPC198242
0.9	High Similarity	NPC211403
0.8989	High Similarity	NPC213832
0.8989	High Similarity	NPC57954
0.8989	High Similarity	NPC220498
0.8977	High Similarity	NPC153604
0.8977	High Similarity	NPC4643
0.8977	High Similarity	NPC57469
0.8953	High Similarity	NPC472743
0.8953	High Similarity	NPC475726
0.8913	High Similarity	NPC263135
0.8913	High Similarity	NPC288906
0.8901	High Similarity	NPC294263
0.8889	High Similarity	NPC169933
0.8876	High Similarity	NPC4309
0.8876	High Similarity	NPC471900
0.8864	High Similarity	NPC472738
0.883	High Similarity	NPC28864
0.883	High Similarity	NPC38471
0.883	High Similarity	NPC38296
0.883	High Similarity	NPC20479
0.883	High Similarity	NPC98837
0.883	High Similarity	NPC471038
0.883	High Similarity	NPC162459
0.8817	High Similarity	NPC329910
0.8817	High Similarity	NPC234564
0.8804	High Similarity	NPC470385
0.8804	High Similarity	NPC470386
0.8791	High Similarity	NPC160506
0.8778	High Similarity	NPC247312
0.8778	High Similarity	NPC271974
0.875	High Similarity	NPC201655
0.875	High Similarity	NPC292553
0.8737	High Similarity	NPC293866
0.8723	High Similarity	NPC10864
0.871	High Similarity	NPC266431
0.871	High Similarity	NPC470232
0.871	High Similarity	NPC470229
0.8696	High Similarity	NPC471902
0.8696	High Similarity	NPC287118
0.8696	High Similarity	NPC473690
0.8696	High Similarity	NPC475061
0.8681	High Similarity	NPC100313
0.8681	High Similarity	NPC46758
0.8681	High Similarity	NPC80401
0.8667	High Similarity	NPC472739
0.8646	High Similarity	NPC52899
0.8646	High Similarity	NPC252614
0.8646	High Similarity	NPC71706
0.8646	High Similarity	NPC253886
0.8646	High Similarity	NPC121218
0.8646	High Similarity	NPC289148
0.8646	High Similarity	NPC46848
0.8646	High Similarity	NPC163963
0.8636	High Similarity	NPC146683
0.8636	High Similarity	NPC264665
0.8636	High Similarity	NPC74595
0.8636	High Similarity	NPC474233
0.8632	High Similarity	NPC89099
0.8617	High Similarity	NPC470387
0.8605	High Similarity	NPC164999
0.8602	High Similarity	NPC47853
0.8602	High Similarity	NPC475118
0.8587	High Similarity	NPC471901
0.8587	High Similarity	NPC475416
0.8587	High Similarity	NPC476168
0.8587	High Similarity	NPC250753
0.8557	High Similarity	NPC170615
0.8557	High Similarity	NPC246736
0.8557	High Similarity	NPC76866
0.8557	High Similarity	NPC214946
0.8557	High Similarity	NPC148628
0.8557	High Similarity	NPC304832
0.8557	High Similarity	NPC286519
0.8557	High Similarity	NPC88203
0.8557	High Similarity	NPC275990
0.8556	High Similarity	NPC259009
0.8556	High Similarity	NPC174619
0.8542	High Similarity	NPC37047
0.8542	High Similarity	NPC94906
0.8542	High Similarity	NPC180733
0.8542	High Similarity	NPC287676
0.8542	High Similarity	NPC470388
0.8542	High Similarity	NPC41971
0.8539	High Similarity	NPC98270
0.8526	High Similarity	NPC190554
0.8523	High Similarity	NPC118800
0.8523	High Similarity	NPC471037
0.8511	High Similarity	NPC48330
0.8511	High Similarity	NPC279974
0.8511	High Similarity	NPC473240
0.8495	Intermediate Similarity	NPC477855
0.8495	Intermediate Similarity	NPC181594
0.8495	Intermediate Similarity	NPC144739
0.8488	Intermediate Similarity	NPC320144
0.8488	Intermediate Similarity	NPC201459
0.8488	Intermediate Similarity	NPC192744
0.8485	Intermediate Similarity	NPC231530
0.8485	Intermediate Similarity	NPC278628
0.8478	Intermediate Similarity	NPC291028
0.8469	Intermediate Similarity	NPC312900
0.8469	Intermediate Similarity	NPC87927
0.8469	Intermediate Similarity	NPC277074
0.8469	Intermediate Similarity	NPC139347
0.8469	Intermediate Similarity	NPC122811
0.8469	Intermediate Similarity	NPC209298
0.8462	Intermediate Similarity	NPC146937
0.8462	Intermediate Similarity	NPC193360
0.8454	Intermediate Similarity	NPC295276
0.8454	Intermediate Similarity	NPC75941
0.8444	Intermediate Similarity	NPC471042
0.8444	Intermediate Similarity	NPC187545
0.8444	Intermediate Similarity	NPC98236
0.8444	Intermediate Similarity	NPC70661
0.8444	Intermediate Similarity	NPC269396
0.8438	Intermediate Similarity	NPC78427
0.8438	Intermediate Similarity	NPC114274
0.8438	Intermediate Similarity	NPC472028
0.8438	Intermediate Similarity	NPC474793
0.8438	Intermediate Similarity	NPC16911
0.8427	Intermediate Similarity	NPC475509
0.8421	Intermediate Similarity	NPC476327
0.8421	Intermediate Similarity	NPC104568
0.8421	Intermediate Similarity	NPC476318
0.8421	Intermediate Similarity	NPC13949
0.8421	Intermediate Similarity	NPC173272
0.8409	Intermediate Similarity	NPC289486
0.8409	Intermediate Similarity	NPC61107
0.8409	Intermediate Similarity	NPC30583
0.8404	Intermediate Similarity	NPC104371
0.8404	Intermediate Similarity	NPC101233
0.8404	Intermediate Similarity	NPC292374
0.8404	Intermediate Similarity	NPC153775
0.8404	Intermediate Similarity	NPC215271
0.8404	Intermediate Similarity	NPC302008
0.8404	Intermediate Similarity	NPC280804
0.8404	Intermediate Similarity	NPC469982
0.8404	Intermediate Similarity	NPC129004
0.8404	Intermediate Similarity	NPC111524
0.8404	Intermediate Similarity	NPC91772
0.8404	Intermediate Similarity	NPC289539
0.8404	Intermediate Similarity	NPC474529
0.8404	Intermediate Similarity	NPC191094
0.8404	Intermediate Similarity	NPC29247
0.8404	Intermediate Similarity	NPC261333
0.8404	Intermediate Similarity	NPC166906
0.8387	Intermediate Similarity	NPC470230
0.8387	Intermediate Similarity	NPC198054
0.8387	Intermediate Similarity	NPC105189
0.8387	Intermediate Similarity	NPC299185
0.8387	Intermediate Similarity	NPC86266
0.8387	Intermediate Similarity	NPC212301
0.8387	Intermediate Similarity	NPC110657
0.8384	Intermediate Similarity	NPC47281
0.8384	Intermediate Similarity	NPC29705
0.8384	Intermediate Similarity	NPC301787
0.8384	Intermediate Similarity	NPC98603
0.8372	Intermediate Similarity	NPC224802
0.8372	Intermediate Similarity	NPC34046
0.8372	Intermediate Similarity	NPC80089
0.8372	Intermediate Similarity	NPC324700
0.8372	Intermediate Similarity	NPC185465
0.8372	Intermediate Similarity	NPC171426
0.837	Intermediate Similarity	NPC474704
0.837	Intermediate Similarity	NPC475921
0.8367	Intermediate Similarity	NPC193934
0.8367	Intermediate Similarity	NPC124544
0.8367	Intermediate Similarity	NPC271980
0.8352	Intermediate Similarity	NPC142361
0.8352	Intermediate Similarity	NPC472495
0.8352	Intermediate Similarity	NPC472497
0.8352	Intermediate Similarity	NPC474684
0.8351	Intermediate Similarity	NPC15390
0.8333	Intermediate Similarity	NPC189880
0.8333	Intermediate Similarity	NPC76518
0.8333	Intermediate Similarity	NPC190704
0.8333	Intermediate Similarity	NPC170978
0.8333	Intermediate Similarity	NPC253586
0.8333	Intermediate Similarity	NPC471034
0.8333	Intermediate Similarity	NPC108078
0.8317	Intermediate Similarity	NPC211224
0.8317	Intermediate Similarity	NPC94529

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 NPC244356 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	2178
0.2-0.3	4084
0.3-0.4	1796
0.4-0.5	452
0.5-0.6	176
0.6-0.7	169
0.7-0.8	95
0.8-0.85	7
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9186	High Similarity	NPD7520	Clinical (unspecified phase)
0.8791	High Similarity	NPD8035	Phase 2
0.8791	High Similarity	NPD8034	Phase 2
0.8372	Intermediate Similarity	NPD6115	Approved
0.8372	Intermediate Similarity	NPD6114	Approved
0.8372	Intermediate Similarity	NPD6697	Approved
0.8372	Intermediate Similarity	NPD6118	Approved
0.8191	Intermediate Similarity	NPD7515	Phase 2
0.8172	Intermediate Similarity	NPD5328	Approved
0.814	Intermediate Similarity	NPD6117	Approved
0.8046	Intermediate Similarity	NPD6116	Phase 1
0.8023	Intermediate Similarity	NPD3703	Phase 2
0.8	Intermediate Similarity	NPD6079	Approved
0.7917	Intermediate Similarity	NPD6399	Phase 3
0.7907	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4697	Phase 3
0.7849	Intermediate Similarity	NPD3618	Phase 1
0.7835	Intermediate Similarity	NPD7748	Approved
0.7826	Intermediate Similarity	NPD4786	Approved
0.7778	Intermediate Similarity	NPD7902	Approved
0.7767	Intermediate Similarity	NPD5739	Approved
0.7767	Intermediate Similarity	NPD6675	Approved
0.7767	Intermediate Similarity	NPD7128	Approved
0.7767	Intermediate Similarity	NPD6402	Approved
0.7717	Intermediate Similarity	NPD4788	Approved
0.7714	Intermediate Similarity	NPD6372	Approved
0.7714	Intermediate Similarity	NPD6373	Approved
0.77	Intermediate Similarity	NPD7638	Approved
0.7677	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5221	Approved
0.7677	Intermediate Similarity	NPD5222	Approved
0.7674	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7640	Approved
0.7624	Intermediate Similarity	NPD7639	Approved
0.7619	Intermediate Similarity	NPD6881	Approved
0.7619	Intermediate Similarity	NPD6899	Approved
0.7619	Intermediate Similarity	NPD7320	Approved
0.7609	Intermediate Similarity	NPD3667	Approved
0.76	Intermediate Similarity	NPD5173	Approved
0.76	Intermediate Similarity	NPD4755	Approved
0.757	Intermediate Similarity	NPD6650	Approved
0.757	Intermediate Similarity	NPD6649	Approved
0.7524	Intermediate Similarity	NPD5697	Approved
0.7524	Intermediate Similarity	NPD5701	Approved
0.7477	Intermediate Similarity	NPD6883	Approved
0.7477	Intermediate Similarity	NPD7290	Approved
0.7477	Intermediate Similarity	NPD7102	Approved
0.7475	Intermediate Similarity	NPD7900	Approved
0.7475	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6011	Approved
0.7451	Intermediate Similarity	NPD5285	Approved
0.7451	Intermediate Similarity	NPD5286	Approved
0.7451	Intermediate Similarity	NPD4700	Approved
0.7451	Intermediate Similarity	NPD4696	Approved
0.7442	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4632	Approved
0.7429	Intermediate Similarity	NPD6008	Approved
0.7407	Intermediate Similarity	NPD8130	Phase 1
0.7407	Intermediate Similarity	NPD6869	Approved
0.7407	Intermediate Similarity	NPD6617	Approved
0.7407	Intermediate Similarity	NPD6847	Approved
0.7407	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7525	Registered
0.7383	Intermediate Similarity	NPD6013	Approved
0.7383	Intermediate Similarity	NPD6012	Approved
0.7383	Intermediate Similarity	NPD6014	Approved
0.7379	Intermediate Similarity	NPD5223	Approved
0.7374	Intermediate Similarity	NPD4202	Approved
0.7339	Intermediate Similarity	NPD6882	Approved
0.7339	Intermediate Similarity	NPD8297	Approved
0.732	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5225	Approved
0.7308	Intermediate Similarity	NPD4633	Approved
0.7308	Intermediate Similarity	NPD5226	Approved
0.7308	Intermediate Similarity	NPD5224	Approved
0.7308	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD6081	Approved
0.7263	Intermediate Similarity	NPD3133	Approved
0.7263	Intermediate Similarity	NPD3665	Phase 1
0.7263	Intermediate Similarity	NPD3666	Approved
0.7255	Intermediate Similarity	NPD6083	Phase 2
0.7255	Intermediate Similarity	NPD6084	Phase 2
0.7238	Intermediate Similarity	NPD4754	Approved
0.7238	Intermediate Similarity	NPD5174	Approved
0.7238	Intermediate Similarity	NPD5175	Approved
0.7232	Intermediate Similarity	NPD6009	Approved
0.717	Intermediate Similarity	NPD5141	Approved
0.7159	Intermediate Similarity	NPD4789	Approved
0.7159	Intermediate Similarity	NPD4245	Approved
0.7159	Intermediate Similarity	NPD4244	Approved
0.7156	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD6868	Approved
0.713	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5360	Phase 3
0.7126	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD8133	Approved
0.7113	Intermediate Similarity	NPD7146	Approved
0.7113	Intermediate Similarity	NPD6684	Approved
0.7113	Intermediate Similarity	NPD7521	Approved
0.7113	Intermediate Similarity	NPD7334	Approved
0.7113	Intermediate Similarity	NPD6409	Approved
0.7113	Intermediate Similarity	NPD5330	Approved
0.7103	Intermediate Similarity	NPD4767	Approved
0.7103	Intermediate Similarity	NPD4768	Approved
0.7093	Intermediate Similarity	NPD4224	Phase 2
0.7083	Intermediate Similarity	NPD3668	Phase 3
0.708	Intermediate Similarity	NPD7115	Discovery
0.7071	Intermediate Similarity	NPD4753	Phase 2
0.7059	Intermediate Similarity	NPD7736	Approved
0.7059	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3698	Phase 2
0.7043	Intermediate Similarity	NPD6319	Approved
0.7034	Intermediate Similarity	NPD7507	Approved
0.7019	Intermediate Similarity	NPD5696	Approved
0.7018	Intermediate Similarity	NPD6335	Approved
0.7009	Intermediate Similarity	NPD7604	Phase 2
0.7009	Intermediate Similarity	NPD8328	Phase 3
0.6991	Remote Similarity	NPD6274	Approved
0.6983	Remote Similarity	NPD5983	Phase 2
0.6977	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4729	Approved
0.6972	Remote Similarity	NPD5128	Approved
0.6972	Remote Similarity	NPD4730	Approved
0.6972	Remote Similarity	NPD5168	Approved
0.697	Remote Similarity	NPD6903	Approved
0.6957	Remote Similarity	NPD7100	Approved
0.6957	Remote Similarity	NPD7101	Approved
0.6949	Remote Similarity	NPD7492	Approved
0.6939	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5279	Phase 3
0.6931	Remote Similarity	NPD5281	Approved
0.6931	Remote Similarity	NPD5284	Approved
0.693	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6317	Approved
0.6915	Remote Similarity	NPD7645	Phase 2
0.6909	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6059	Approved
0.6897	Remote Similarity	NPD6054	Approved
0.6893	Remote Similarity	NPD5210	Approved
0.6893	Remote Similarity	NPD4629	Approved
0.6893	Remote Similarity	NPD5695	Phase 3
0.6891	Remote Similarity	NPD6336	Discontinued
0.6891	Remote Similarity	NPD6616	Approved
0.6889	Remote Similarity	NPD5777	Approved
0.6881	Remote Similarity	NPD6412	Phase 2
0.6875	Remote Similarity	NPD4221	Approved
0.6875	Remote Similarity	NPD4223	Phase 3
0.687	Remote Similarity	NPD6313	Approved
0.687	Remote Similarity	NPD6314	Approved
0.6869	Remote Similarity	NPD3573	Approved
0.686	Remote Similarity	NPD7319	Approved
0.6848	Remote Similarity	NPD3702	Approved
0.6848	Remote Similarity	NPD7339	Approved
0.6848	Remote Similarity	NPD6942	Approved
0.6847	Remote Similarity	NPD5248	Approved
0.6847	Remote Similarity	NPD5247	Approved
0.6847	Remote Similarity	NPD5135	Approved
0.6847	Remote Similarity	NPD5169	Approved
0.6847	Remote Similarity	NPD5249	Phase 3
0.6847	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5251	Approved
0.6847	Remote Similarity	NPD5250	Approved
0.6838	Remote Similarity	NPD6909	Approved
0.6838	Remote Similarity	NPD6908	Approved
0.6838	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5329	Approved
0.6833	Remote Similarity	NPD7078	Approved
0.6833	Remote Similarity	NPD8293	Discontinued
0.6809	Remote Similarity	NPD3671	Phase 1
0.6809	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8418	Phase 2
0.6786	Remote Similarity	NPD5127	Approved
0.6786	Remote Similarity	NPD5215	Approved
0.6786	Remote Similarity	NPD5216	Approved
0.6786	Remote Similarity	NPD5217	Approved
0.678	Remote Similarity	NPD6370	Approved
0.6768	Remote Similarity	NPD6098	Approved
0.6765	Remote Similarity	NPD6411	Approved
0.6735	Remote Similarity	NPD4197	Approved
0.6733	Remote Similarity	NPD6904	Approved
0.6733	Remote Similarity	NPD6673	Approved
0.6733	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6080	Approved
0.6703	Remote Similarity	NPD4758	Discontinued
0.6697	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6015	Approved
0.6695	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5988	Approved
0.6635	Remote Similarity	NPD6001	Approved
0.6632	Remote Similarity	NPD3617	Approved
0.6632	Remote Similarity	NPD5364	Discontinued
0.6609	Remote Similarity	NPD5167	Approved
0.6602	Remote Similarity	NPD7637	Suspended

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