NPASS Compound

Structure

NPC473690 OpenBabel07101719122D 38 42 0 0 1 0 0 0 0 0999 V2000 3.8779 -1.4338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2690 -1.9566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 -4.8837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2945 1.8690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3603 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8719 0.5842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1948 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 -3.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6207 1.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9225 -1.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2294 -4.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6207 -0.3018 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5377 -1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3835 -2.9302 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6918 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8719 -1.1076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6918 -1.9535 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8459 -0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3835 -1.9535 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 -1.6918 1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0753 -4.8837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8487 -1.1076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 -0.2617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2294 -3.4186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 6 31 1 0 0 0 0 8 37 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 21 35 2 0 0 0 0 21 38 1 0 0 0 0 22 20 1 1 0 0 0 22 27 1 0 0 0 0 23 27 1 0 0 0 0 23 33 1 1 0 0 0 24 30 1 6 0 0 0 24 31 1 0 0 0 0 25 30 1 6 0 0 0 25 32 1 0 0 0 0 26 32 1 1 0 0 0 26 38 1 0 0 0 0 27 29 1 6 0 0 0 28 32 1 0 0 0 0 28 36 2 0 0 0 0 28 37 1 0 0 0 0 29 4 1 6 0 0 0 30 5 1 6 0 0 0 31 33 1 1 0 0 0 32 7 1 1 0 0 0 33 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.38
Volume:	572.583
LogP:	4.961
LogD:	4.661
LogS:	-5.104
# Rotatable Bonds:	6
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	5.117
Fsp3:	0.879
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.277
MDCK Permeability:	4.397015072754584e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	90.07589721679688%
Volume Distribution (VD):	1.337
Pgp-substrate:	2.323204517364502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.934
CYP2C9-inhibitor:	0.207
CYP2C9-substrate:	0.344
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.558
CYP3A4-inhibitor:	0.804
CYP3A4-substrate:	0.581

ADMET: Excretion

Clearance (CL):	4.122
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.256
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.161
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.924
Carcinogencity:	0.008
Eye Corrosion:	0.371
Eye Irritation:	0.542
Respiratory Toxicity:	0.391

Download Data

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

Natural Product: NPC473690

Natural Product ID:	NPC473690
*Common Name:**	Methyl 3Alpha-Acetoxy-27-Hydroxylup-20(29)-En-24-Oate
IUPAC Name:	methyl (1R,3aR,5aS,5bR,7aR,8R,9R,11aR,11bR,13aR,13bR)-9-acetyloxy-5a-(hydroxymethyl)-3a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-carboxylate
Synonyms:
Standard InCHIKey:	OZFWHMKAQGWDTK-RPSYARDLSA-N
Standard InCHI:	InChI=1S/C33H52O5/c1-20(2)22-11-14-29(4)17-18-33(19-34)23(27(22)29)9-10-24-30(5)15-13-26(38-21(3)35)32(7,28(36)37-8)25(30)12-16-31(24,33)6/h22-27,34H,1,9-19H2,2-8H3/t22-,23+,24+,25+,26+,27+,29+,30+,31+,32+,33-/m0/s1
SMILES:	CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)CO)C)(C)C(=O)OC)OC(=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449310
PubChem CID:	44575408
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
NPO10628	Boswellia papyrifera	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730241]
NPO10628	Boswellia papyrifera	Species	Burseraceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1591	Individual Protein	Prolyl endopeptidase	Homo sapiens	IC50	=	57430.0	nM	PMID[515862]

☑ 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 NPC473690 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	1682
0.2-0.3	6101
0.3-0.4	14922
0.4-0.5	6883
0.5-0.6	5089
0.6-0.7	4563
0.7-0.8	2775
0.8-0.85	367
0.85-0.9	71
0.9-0.95	23
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC287118
1.0	High Similarity	NPC471902
0.9884	High Similarity	NPC475416
0.9884	High Similarity	NPC471901
0.9651	High Similarity	NPC213832
0.9651	High Similarity	NPC57954
0.9535	High Similarity	NPC4309
0.9535	High Similarity	NPC471900
0.9419	High Similarity	NPC269360
0.9419	High Similarity	NPC33768
0.9419	High Similarity	NPC264005
0.9318	High Similarity	NPC169933
0.9302	High Similarity	NPC12774
0.9302	High Similarity	NPC2783
0.9213	High Similarity	NPC160506
0.9186	High Similarity	NPC98270
0.9186	High Similarity	NPC294438
0.9186	High Similarity	NPC264317
0.9121	High Similarity	NPC205173
0.9091	High Similarity	NPC146937
0.9091	High Similarity	NPC474719
0.9091	High Similarity	NPC16377
0.907	High Similarity	NPC475509
0.9022	High Similarity	NPC327788
0.8989	High Similarity	NPC220498
0.8977	High Similarity	NPC134197
0.8966	High Similarity	NPC201655
0.8953	High Similarity	NPC471037
0.8953	High Similarity	NPC5280
0.8936	High Similarity	NPC94906
0.8925	High Similarity	NPC253586
0.8913	High Similarity	NPC210214
0.8864	High Similarity	NPC168231
0.8842	High Similarity	NPC75941
0.883	High Similarity	NPC472028
0.8817	High Similarity	NPC120708
0.8804	High Similarity	NPC184006
0.8804	High Similarity	NPC303863
0.8804	High Similarity	NPC277399
0.8804	High Similarity	NPC78580
0.8804	High Similarity	NPC47853
0.8804	High Similarity	NPC23621
0.8778	High Similarity	NPC271974
0.8778	High Similarity	NPC247312
0.8764	High Similarity	NPC57469
0.875	High Similarity	NPC124544
0.8737	High Similarity	NPC108371
0.8736	High Similarity	NPC475726
0.8736	High Similarity	NPC472743
0.871	High Similarity	NPC288906
0.871	High Similarity	NPC263135
0.871	High Similarity	NPC266431
0.871	High Similarity	NPC23241
0.871	High Similarity	NPC279974
0.871	High Similarity	NPC195715
0.8696	High Similarity	NPC244356
0.8696	High Similarity	NPC294263
0.8696	High Similarity	NPC86368
0.8696	High Similarity	NPC291373
0.8696	High Similarity	NPC475061
0.8696	High Similarity	NPC224060
0.8681	High Similarity	NPC471896
0.8667	High Similarity	NPC211162
0.8667	High Similarity	NPC183374
0.866	High Similarity	NPC470310
0.8636	High Similarity	NPC475745
0.8636	High Similarity	NPC264665
0.8636	High Similarity	NPC74595
0.8636	High Similarity	NPC474482
0.8632	High Similarity	NPC474092
0.8632	High Similarity	NPC78427
0.8632	High Similarity	NPC16911
0.8632	High Similarity	NPC119036
0.8632	High Similarity	NPC164349
0.8617	High Similarity	NPC329910
0.8617	High Similarity	NPC234564
0.8617	High Similarity	NPC13949
0.8605	High Similarity	NPC304194
0.8605	High Similarity	NPC261616
0.8602	High Similarity	NPC469982
0.8587	High Similarity	NPC966
0.8587	High Similarity	NPC228784
0.8587	High Similarity	NPC282616
0.8587	High Similarity	NPC250753
0.8587	High Similarity	NPC155120
0.8587	High Similarity	NPC288833
0.8587	High Similarity	NPC324341
0.8571	High Similarity	NPC474704
0.8571	High Similarity	NPC474889
0.8571	High Similarity	NPC475921
0.8556	High Similarity	NPC252714
0.8542	High Similarity	NPC180733
0.8542	High Similarity	NPC37047
0.8542	High Similarity	NPC287676
0.8542	High Similarity	NPC41971
0.8539	High Similarity	NPC292553
0.8526	High Similarity	NPC26413
0.8511	High Similarity	NPC470232
0.8511	High Similarity	NPC470229
0.8488	Intermediate Similarity	NPC305835
0.8485	Intermediate Similarity	NPC265127
0.8478	Intermediate Similarity	NPC175628
0.8478	Intermediate Similarity	NPC120840
0.8478	Intermediate Similarity	NPC86372
0.8478	Intermediate Similarity	NPC172361
0.8478	Intermediate Similarity	NPC113989
0.8478	Intermediate Similarity	NPC111585
0.8478	Intermediate Similarity	NPC148414
0.8454	Intermediate Similarity	NPC289148
0.8454	Intermediate Similarity	NPC163963
0.8454	Intermediate Similarity	NPC46848
0.8454	Intermediate Similarity	NPC52899
0.8444	Intermediate Similarity	NPC187545
0.8444	Intermediate Similarity	NPC98236
0.8444	Intermediate Similarity	NPC472738
0.8444	Intermediate Similarity	NPC269396
0.8444	Intermediate Similarity	NPC80590
0.8438	Intermediate Similarity	NPC474793
0.8438	Intermediate Similarity	NPC471038
0.8431	Intermediate Similarity	NPC11035
0.8427	Intermediate Similarity	NPC319909
0.8427	Intermediate Similarity	NPC299963
0.8427	Intermediate Similarity	NPC474233
0.8421	Intermediate Similarity	NPC98874
0.8409	Intermediate Similarity	NPC289486
0.8409	Intermediate Similarity	NPC61107
0.8404	Intermediate Similarity	NPC470385
0.8404	Intermediate Similarity	NPC475118
0.8404	Intermediate Similarity	NPC470386
0.8404	Intermediate Similarity	NPC222047
0.8391	Intermediate Similarity	NPC206735
0.8387	Intermediate Similarity	NPC77099
0.8387	Intermediate Similarity	NPC6255
0.8387	Intermediate Similarity	NPC470590
0.8387	Intermediate Similarity	NPC60755
0.8387	Intermediate Similarity	NPC26888
0.8387	Intermediate Similarity	NPC211403
0.8387	Intermediate Similarity	NPC471588
0.8387	Intermediate Similarity	NPC285184
0.8387	Intermediate Similarity	NPC198242
0.837	Intermediate Similarity	NPC225585
0.837	Intermediate Similarity	NPC263393
0.837	Intermediate Similarity	NPC471043
0.837	Intermediate Similarity	NPC130520
0.837	Intermediate Similarity	NPC59263
0.837	Intermediate Similarity	NPC30522
0.837	Intermediate Similarity	NPC24772
0.837	Intermediate Similarity	NPC474570
0.837	Intermediate Similarity	NPC127689
0.837	Intermediate Similarity	NPC121798
0.837	Intermediate Similarity	NPC116146
0.837	Intermediate Similarity	NPC234346
0.837	Intermediate Similarity	NPC61543
0.837	Intermediate Similarity	NPC293048
0.837	Intermediate Similarity	NPC77001
0.837	Intermediate Similarity	NPC270768
0.837	Intermediate Similarity	NPC253618
0.8367	Intermediate Similarity	NPC473788
0.8367	Intermediate Similarity	NPC76866
0.8367	Intermediate Similarity	NPC286519
0.8367	Intermediate Similarity	NPC475558
0.8367	Intermediate Similarity	NPC304832
0.8367	Intermediate Similarity	NPC214946
0.8367	Intermediate Similarity	NPC88203
0.8367	Intermediate Similarity	NPC148628
0.8367	Intermediate Similarity	NPC275990
0.8367	Intermediate Similarity	NPC246736
0.8352	Intermediate Similarity	NPC142361
0.8352	Intermediate Similarity	NPC4643
0.8352	Intermediate Similarity	NPC474684
0.8333	Intermediate Similarity	NPC469810
0.8333	Intermediate Similarity	NPC476878
0.8333	Intermediate Similarity	NPC476879
0.8317	Intermediate Similarity	NPC88744
0.8316	Intermediate Similarity	NPC184848
0.8316	Intermediate Similarity	NPC474727
0.8316	Intermediate Similarity	NPC69548
0.8316	Intermediate Similarity	NPC473648
0.8316	Intermediate Similarity	NPC148523
0.8316	Intermediate Similarity	NPC98639
0.8315	Intermediate Similarity	NPC471036
0.8315	Intermediate Similarity	NPC473742
0.8315	Intermediate Similarity	NPC291320
0.8315	Intermediate Similarity	NPC245866
0.8298	Intermediate Similarity	NPC298554
0.8298	Intermediate Similarity	NPC470224
0.8298	Intermediate Similarity	NPC63118
0.8298	Intermediate Similarity	NPC49776
0.8298	Intermediate Similarity	NPC474436
0.8283	Intermediate Similarity	NPC139347
0.8283	Intermediate Similarity	NPC87927
0.828	Intermediate Similarity	NPC111110
0.828	Intermediate Similarity	NPC470589
0.828	Intermediate Similarity	NPC126369
0.828	Intermediate Similarity	NPC130278
0.828	Intermediate Similarity	NPC474728
0.8276	Intermediate Similarity	NPC201459
0.8276	Intermediate Similarity	NPC192744
0.8269	Intermediate Similarity	NPC146563
0.8265	Intermediate Similarity	NPC71706

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 NPC473690 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	2041
0.2-0.3	4034
0.3-0.4	1939
0.4-0.5	478
0.5-0.6	193
0.6-0.7	182
0.7-0.8	89
0.8-0.85	2
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9213	High Similarity	NPD8035	Phase 2
0.9213	High Similarity	NPD8034	Phase 2
0.9186	High Similarity	NPD7520	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD7748	Approved
0.814	Intermediate Similarity	NPD6117	Approved
0.8046	Intermediate Similarity	NPD6116	Phase 1
0.8	Intermediate Similarity	NPD7515	Phase 2
0.7959	Intermediate Similarity	NPD7902	Approved
0.7955	Intermediate Similarity	NPD6118	Approved
0.7955	Intermediate Similarity	NPD6115	Approved
0.7955	Intermediate Similarity	NPD6114	Approved
0.7955	Intermediate Similarity	NPD6697	Approved
0.7917	Intermediate Similarity	NPD6399	Phase 3
0.7907	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD5739	Approved
0.7767	Intermediate Similarity	NPD6675	Approved
0.7767	Intermediate Similarity	NPD6402	Approved
0.7767	Intermediate Similarity	NPD7128	Approved
0.77	Intermediate Similarity	NPD7638	Approved
0.7653	Intermediate Similarity	NPD7900	Approved
0.7653	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4786	Approved
0.7624	Intermediate Similarity	NPD7640	Approved
0.7624	Intermediate Similarity	NPD7639	Approved
0.7619	Intermediate Similarity	NPD6881	Approved
0.7619	Intermediate Similarity	NPD7320	Approved
0.7619	Intermediate Similarity	NPD6899	Approved
0.7604	Intermediate Similarity	NPD5328	Approved
0.76	Intermediate Similarity	NPD6083	Phase 2
0.76	Intermediate Similarity	NPD6084	Phase 2
0.757	Intermediate Similarity	NPD8130	Phase 1
0.7547	Intermediate Similarity	NPD6372	Approved
0.7547	Intermediate Similarity	NPD6373	Approved
0.7545	Intermediate Similarity	NPD7115	Discovery
0.7527	Intermediate Similarity	NPD4788	Approved
0.7524	Intermediate Similarity	NPD5697	Approved
0.7524	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6883	Approved
0.7477	Intermediate Similarity	NPD7290	Approved
0.7477	Intermediate Similarity	NPD7102	Approved
0.7474	Intermediate Similarity	NPD3618	Phase 1
0.7471	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6079	Approved
0.7431	Intermediate Similarity	NPD8133	Approved
0.7419	Intermediate Similarity	NPD3667	Approved
0.7407	Intermediate Similarity	NPD6869	Approved
0.7407	Intermediate Similarity	NPD6649	Approved
0.7407	Intermediate Similarity	NPD6617	Approved
0.7407	Intermediate Similarity	NPD6847	Approved
0.7407	Intermediate Similarity	NPD6650	Approved
0.7391	Intermediate Similarity	NPD7525	Registered
0.7383	Intermediate Similarity	NPD6013	Approved
0.7383	Intermediate Similarity	NPD6012	Approved
0.7383	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6882	Approved
0.732	Intermediate Similarity	NPD6672	Approved
0.732	Intermediate Similarity	NPD5737	Approved
0.7292	Intermediate Similarity	NPD6684	Approved
0.7292	Intermediate Similarity	NPD5330	Approved
0.7292	Intermediate Similarity	NPD7146	Approved
0.7292	Intermediate Similarity	NPD6409	Approved
0.7292	Intermediate Similarity	NPD7334	Approved
0.7292	Intermediate Similarity	NPD7521	Approved
0.729	Intermediate Similarity	NPD6011	Approved
0.7283	Intermediate Similarity	NPD7645	Phase 2
0.7273	Intermediate Similarity	NPD6411	Approved
0.7255	Intermediate Similarity	NPD4755	Approved
0.7248	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5695	Phase 3
0.7203	Intermediate Similarity	NPD7736	Approved
0.72	Intermediate Similarity	NPD4202	Approved
0.7184	Intermediate Similarity	NPD5696	Approved
0.7157	Intermediate Similarity	NPD5222	Approved
0.7157	Intermediate Similarity	NPD5221	Approved
0.7157	Intermediate Similarity	NPD4697	Phase 3
0.7157	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD6903	Approved
0.7115	Intermediate Similarity	NPD5285	Approved
0.7115	Intermediate Similarity	NPD4700	Approved
0.7115	Intermediate Similarity	NPD5286	Approved
0.7115	Intermediate Similarity	NPD4696	Approved
0.71	Intermediate Similarity	NPD7637	Suspended
0.7087	Intermediate Similarity	NPD5173	Approved
0.7083	Intermediate Similarity	NPD3665	Phase 1
0.7083	Intermediate Similarity	NPD3666	Approved
0.7083	Intermediate Similarity	NPD3133	Approved
0.708	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5777	Approved
0.7079	Intermediate Similarity	NPD6081	Approved
0.7071	Intermediate Similarity	NPD4753	Phase 2
0.7071	Intermediate Similarity	NPD6101	Approved
0.7071	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6319	Approved
0.7033	Intermediate Similarity	NPD3702	Approved
0.7033	Intermediate Similarity	NPD3703	Phase 2
0.7019	Intermediate Similarity	NPD4225	Approved
0.7009	Intermediate Similarity	NPD8328	Phase 3
0.7	Intermediate Similarity	NPD7319	Approved
0.6991	Remote Similarity	NPD6274	Approved
0.6991	Remote Similarity	NPD6868	Approved
0.6981	Remote Similarity	NPD5211	Phase 2
0.6981	Remote Similarity	NPD5225	Approved
0.6981	Remote Similarity	NPD5226	Approved
0.6981	Remote Similarity	NPD4633	Approved
0.6981	Remote Similarity	NPD5224	Approved
0.6975	Remote Similarity	NPD8293	Discontinued
0.6972	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4245	Approved
0.6966	Remote Similarity	NPD4244	Approved
0.6966	Remote Similarity	NPD4789	Approved
0.6957	Remote Similarity	NPD7101	Approved
0.6957	Remote Similarity	NPD7100	Approved
0.6949	Remote Similarity	NPD7492	Approved
0.6939	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6098	Approved
0.6932	Remote Similarity	NPD5360	Phase 3
0.6932	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5175	Approved
0.6916	Remote Similarity	NPD5174	Approved
0.6909	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD3668	Phase 3
0.69	Remote Similarity	NPD6080	Approved
0.69	Remote Similarity	NPD6673	Approved
0.69	Remote Similarity	NPD6904	Approved
0.6897	Remote Similarity	NPD6059	Approved
0.6897	Remote Similarity	NPD4224	Phase 2
0.6897	Remote Similarity	NPD6054	Approved
0.6891	Remote Similarity	NPD7507	Approved
0.6891	Remote Similarity	NPD6616	Approved
0.6887	Remote Similarity	NPD5223	Approved
0.6881	Remote Similarity	NPD6412	Phase 2
0.687	Remote Similarity	NPD6335	Approved
0.6854	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3698	Phase 2
0.6852	Remote Similarity	NPD5141	Approved
0.6848	Remote Similarity	NPD6942	Approved
0.6848	Remote Similarity	NPD7339	Approved
0.6847	Remote Similarity	NPD4634	Approved
0.6838	Remote Similarity	NPD6909	Approved
0.6838	Remote Similarity	NPD6908	Approved
0.6833	Remote Similarity	NPD7078	Approved
0.6814	Remote Similarity	NPD4632	Approved
0.6789	Remote Similarity	NPD4768	Approved
0.6789	Remote Similarity	NPD6008	Approved
0.6789	Remote Similarity	NPD4767	Approved
0.6783	Remote Similarity	NPD6317	Approved
0.6782	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6370	Approved
0.6768	Remote Similarity	NPD5279	Phase 3
0.6759	Remote Similarity	NPD4754	Approved
0.6731	Remote Similarity	NPD5210	Approved
0.6731	Remote Similarity	NPD4629	Approved
0.6724	Remote Similarity	NPD6313	Approved
0.6724	Remote Similarity	NPD6314	Approved
0.6701	Remote Similarity	NPD4221	Approved
0.6701	Remote Similarity	NPD4223	Phase 3
0.67	Remote Similarity	NPD3573	Approved
0.6699	Remote Similarity	NPD5779	Approved
0.6699	Remote Similarity	NPD5778	Approved
0.6695	Remote Similarity	NPD6015	Approved
0.6695	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6639	Remote Similarity	NPD5988	Approved
0.6638	Remote Similarity	NPD6009	Approved
0.6636	Remote Similarity	NPD8418	Phase 2
0.6635	Remote Similarity	NPD6001	Approved
0.6634	Remote Similarity	NPD5208	Approved
0.6632	Remote Similarity	NPD3671	Phase 1
0.6632	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.661	Remote Similarity	NPD8294	Approved
0.661	Remote Similarity	NPD8377	Approved
0.6607	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6050	Approved
0.6602	Remote Similarity	NPD5693	Phase 1
0.6602	Remote Similarity	NPD5281	Approved
0.6602	Remote Similarity	NPD5284	Approved
0.6598	Remote Similarity	NPD5369	Approved
0.6596	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7604	Phase 2
0.6581	Remote Similarity	NPD7328	Approved
0.6581	Remote Similarity	NPD7327	Approved
0.6569	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6051	Approved
0.6566	Remote Similarity	NPD4197	Approved
0.6555	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8380	Approved
0.6555	Remote Similarity	NPD8335	Approved
0.6555	Remote Similarity	NPD8033	Approved
0.6555	Remote Similarity	NPD5983	Phase 2
0.6555	Remote Similarity	NPD8379	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