NPASS Compound

Structure

NPC38350 OpenBabel07101718182D 33 36 0 0 1 0 0 0 0 0999 V2000 4.8126 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5254 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8344 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 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 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 3.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 2 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 20 10 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 29 1 1 0 0 0 22 23 2 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 6 0 0 0 25 27 1 0 0 0 0 25 31 2 0 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	509.035
LogP:	7.139
LogD:	4.696
LogS:	-4.472
# Rotatable Bonds:	5
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.432
Synthetic Accessibility Score:	4.655
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.332
MDCK Permeability:	1.1538352737261448e-05
Pgp-inhibitor:	0.36
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.794
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163
Plasma Protein Binding (PPB):	92.14873504638672%
Volume Distribution (VD):	0.945
Pgp-substrate:	2.2993555068969727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.464
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.784

ADMET: Excretion

Clearance (CL):	19.0
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.634
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.236
Maximum Recommended Daily Dose:	0.537
Skin Sensitization:	0.06
Carcinogencity:	0.732
Eye Corrosion:	0.005
Eye Irritation:	0.058
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC38350

Natural Product ID:	NPC38350
*Common Name:**	Beta-Elemonic Acid
IUPAC Name:	(2S)-6-methyl-2-[(5S,10S,13S,14S,17R)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-5-enoic acid
Synonyms:	Beta-Elemonic Acid
Standard InCHIKey:	XLPAINGDLCDYQV-DXXDIINSSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,20-21,24H,8,10-18H2,1-7H3,(H,32,33)/t20-,21+,24+,28+,29-,30+/m0/s1
SMILES:	CC(=CCC[C@@H]([C@H]1CC[C@]2([C@@]1(C)CCC1=C2CC[C@H]2[C@]1(C)CCC(=O)C2(C)C)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL566929
PubChem CID:	24721570
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]
NPO33055	boswellia spp.	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24844534]
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
EC50	2
IC50	4
Others	4

Activity Type	# Activity
Individual Protein	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1591	Individual Protein	Prolyl endopeptidase	Homo sapiens	IC50	=	39740.0	nM	PMID[512648]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	0.0	nM	PMID[512649]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Activity	=	81.1	%	PMID[512650]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Activity	=	70.1	%	PMID[512650]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	10000.0	nM	PMID[512650]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	10000.0	nM	PMID[512650]
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	EC50	>	10000.0	nM	PMID[512649]
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Efficacy	=	0.0	%	PMID[512649]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	Activity	=	16.7	%	PMID[512650]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	900.0	nM	PMID[512650]

☑ 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 NPC38350 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	142
0.1-0.2	1012
0.2-0.3	6224
0.3-0.4	15857
0.4-0.5	7087
0.5-0.6	6686
0.6-0.7	4095
0.7-0.8	1261
0.8-0.85	259
0.85-0.9	53
0.9-0.95	15
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201912
0.9868	High Similarity	NPC260956
0.974	High Similarity	NPC69279
0.974	High Similarity	NPC83569
0.9737	High Similarity	NPC147066
0.9733	High Similarity	NPC477371
0.9481	High Similarity	NPC477372
0.9359	High Similarity	NPC133391
0.9359	High Similarity	NPC320514
0.925	High Similarity	NPC29447
0.9241	High Similarity	NPC168188
0.9241	High Similarity	NPC470015
0.9241	High Similarity	NPC477373
0.9024	High Similarity	NPC187376
0.9024	High Similarity	NPC159046
0.9024	High Similarity	NPC233836
0.9024	High Similarity	NPC96496
0.9024	High Similarity	NPC136948
0.9012	High Similarity	NPC311702
0.9012	High Similarity	NPC123319
0.9012	High Similarity	NPC94531
0.8974	High Similarity	NPC215843
0.8974	High Similarity	NPC196827
0.8974	High Similarity	NPC274996
0.8974	High Similarity	NPC158846
0.8902	High Similarity	NPC155011
0.8902	High Similarity	NPC28252
0.8902	High Similarity	NPC55309
0.8889	High Similarity	NPC165064
0.8889	High Similarity	NPC473246
0.8831	High Similarity	NPC309399
0.8824	High Similarity	NPC204341
0.881	High Similarity	NPC77168
0.881	High Similarity	NPC474570
0.881	High Similarity	NPC262043
0.881	High Similarity	NPC54689
0.881	High Similarity	NPC102414
0.881	High Similarity	NPC84271
0.88	High Similarity	NPC160817
0.8795	High Similarity	NPC474684
0.8795	High Similarity	NPC142361
0.878	High Similarity	NPC473038
0.878	High Similarity	NPC11711
0.878	High Similarity	NPC474083
0.8765	High Similarity	NPC477852
0.8765	High Similarity	NPC167103
0.8765	High Similarity	NPC310470
0.875	High Similarity	NPC278459
0.875	High Similarity	NPC274050
0.875	High Similarity	NPC263272
0.875	High Similarity	NPC162632
0.875	High Similarity	NPC267691
0.875	High Similarity	NPC471898
0.8734	High Similarity	NPC231431
0.8734	High Similarity	NPC192744
0.8721	High Similarity	NPC66429
0.8721	High Similarity	NPC152897
0.8718	High Similarity	NPC165711
0.8718	High Similarity	NPC471899
0.8718	High Similarity	NPC66105
0.8718	High Similarity	NPC107039
0.8718	High Similarity	NPC471897
0.8706	High Similarity	NPC111585
0.8706	High Similarity	NPC175628
0.8706	High Similarity	NPC148414
0.8701	High Similarity	NPC192540
0.8701	High Similarity	NPC279666
0.869	High Similarity	NPC242864
0.8659	High Similarity	NPC85774
0.8659	High Similarity	NPC209882
0.8659	High Similarity	NPC59453
0.8659	High Similarity	NPC221758
0.8659	High Similarity	NPC82902
0.8659	High Similarity	NPC214043
0.8659	High Similarity	NPC164577
0.8642	High Similarity	NPC251779
0.8642	High Similarity	NPC3511
0.8642	High Similarity	NPC327969
0.8642	High Similarity	NPC193347
0.8642	High Similarity	NPC142253
0.8642	High Similarity	NPC240302
0.8642	High Similarity	NPC69101
0.8642	High Similarity	NPC296367
0.8642	High Similarity	NPC321289
0.8625	High Similarity	NPC37038
0.8608	High Similarity	NPC260385
0.8608	High Similarity	NPC321514
0.8608	High Similarity	NPC74410
0.8608	High Similarity	NPC179028
0.8608	High Similarity	NPC110094
0.8608	High Similarity	NPC280654
0.8605	High Similarity	NPC297265
0.8605	High Similarity	NPC154101
0.8605	High Similarity	NPC26888
0.859	High Similarity	NPC20466
0.859	High Similarity	NPC69143
0.859	High Similarity	NPC180886
0.859	High Similarity	NPC246445
0.859	High Similarity	NPC89294
0.8588	High Similarity	NPC475921
0.8588	High Similarity	NPC474889
0.8588	High Similarity	NPC474704
0.8571	High Similarity	NPC183503
0.8571	High Similarity	NPC241854
0.8571	High Similarity	NPC283908
0.8571	High Similarity	NPC251970
0.8571	High Similarity	NPC312215
0.8571	High Similarity	NPC167877
0.8571	High Similarity	NPC301065
0.8571	High Similarity	NPC161923
0.8571	High Similarity	NPC103958
0.8571	High Similarity	NPC476046
0.8554	High Similarity	NPC470223
0.8554	High Similarity	NPC469948
0.8554	High Similarity	NPC474218
0.8554	High Similarity	NPC269638
0.8554	High Similarity	NPC471224
0.8554	High Similarity	NPC474537
0.8537	High Similarity	NPC70834
0.8537	High Similarity	NPC97913
0.8523	High Similarity	NPC171395
0.8523	High Similarity	NPC263347
0.8519	High Similarity	NPC142244
0.8506	High Similarity	NPC206810
0.8506	High Similarity	NPC243866
0.85	High Similarity	NPC199595
0.85	High Similarity	NPC16394
0.85	High Similarity	NPC472490
0.8488	Intermediate Similarity	NPC469400
0.8488	Intermediate Similarity	NPC471896
0.8481	Intermediate Similarity	NPC212661
0.8481	Intermediate Similarity	NPC68828
0.8481	Intermediate Similarity	NPC471035
0.8471	Intermediate Similarity	NPC294480
0.8471	Intermediate Similarity	NPC471722
0.8452	Intermediate Similarity	NPC212843
0.8452	Intermediate Similarity	NPC474732
0.8452	Intermediate Similarity	NPC51014
0.8452	Intermediate Similarity	NPC89077
0.8452	Intermediate Similarity	NPC94755
0.8452	Intermediate Similarity	NPC31564
0.8452	Intermediate Similarity	NPC474778
0.8452	Intermediate Similarity	NPC118648
0.8452	Intermediate Similarity	NPC474733
0.8452	Intermediate Similarity	NPC72133
0.8452	Intermediate Similarity	NPC145879
0.8452	Intermediate Similarity	NPC475022
0.8452	Intermediate Similarity	NPC469994
0.8452	Intermediate Similarity	NPC222613
0.8442	Intermediate Similarity	NPC161187
0.8442	Intermediate Similarity	NPC244708
0.8442	Intermediate Similarity	NPC330659
0.8434	Intermediate Similarity	NPC194937
0.8434	Intermediate Similarity	NPC472865
0.8434	Intermediate Similarity	NPC237712
0.8434	Intermediate Similarity	NPC144258
0.8434	Intermediate Similarity	NPC87552
0.8434	Intermediate Similarity	NPC96095
0.8434	Intermediate Similarity	NPC476038
0.8434	Intermediate Similarity	NPC320801
0.8427	Intermediate Similarity	NPC472941
0.8427	Intermediate Similarity	NPC456
0.8427	Intermediate Similarity	NPC155676
0.8415	Intermediate Similarity	NPC100297
0.8415	Intermediate Similarity	NPC472239
0.8415	Intermediate Similarity	NPC151519
0.8409	Intermediate Similarity	NPC469406
0.8409	Intermediate Similarity	NPC166906
0.8395	Intermediate Similarity	NPC104545
0.8395	Intermediate Similarity	NPC26139
0.8395	Intermediate Similarity	NPC472478
0.8391	Intermediate Similarity	NPC86266
0.8391	Intermediate Similarity	NPC23434
0.8391	Intermediate Similarity	NPC212301
0.8391	Intermediate Similarity	NPC110657
0.8391	Intermediate Similarity	NPC189520
0.8375	Intermediate Similarity	NPC469996
0.8375	Intermediate Similarity	NPC321690
0.8375	Intermediate Similarity	NPC82635
0.8372	Intermediate Similarity	NPC86319
0.8372	Intermediate Similarity	NPC215029
0.8372	Intermediate Similarity	NPC275740
0.8372	Intermediate Similarity	NPC214387
0.8372	Intermediate Similarity	NPC476733
0.8354	Intermediate Similarity	NPC899
0.8353	Intermediate Similarity	NPC128644
0.8353	Intermediate Similarity	NPC317590
0.8353	Intermediate Similarity	NPC93778
0.8353	Intermediate Similarity	NPC58063
0.8353	Intermediate Similarity	NPC90652
0.8353	Intermediate Similarity	NPC475740
0.8353	Intermediate Similarity	NPC136548
0.8333	Intermediate Similarity	NPC142649
0.8333	Intermediate Similarity	NPC283733
0.8333	Intermediate Similarity	NPC8571
0.8315	Intermediate Similarity	NPC174948
0.8315	Intermediate Similarity	NPC469599
0.8315	Intermediate Similarity	NPC317586
0.8315	Intermediate Similarity	NPC222845
0.8315	Intermediate Similarity	NPC45324

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 NPC38350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1451
0.2-0.3	4210
0.3-0.4	2243
0.4-0.5	601
0.5-0.6	206
0.6-0.7	175
0.7-0.8	94
0.8-0.85	28
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8659	High Similarity	NPD4786	Approved
0.8642	High Similarity	NPD4223	Phase 3
0.8642	High Similarity	NPD4221	Approved
0.8605	High Similarity	NPD5281	Approved
0.8605	High Similarity	NPD5284	Approved
0.8554	High Similarity	NPD5329	Approved
0.8506	High Similarity	NPD6399	Phase 3
0.8452	Intermediate Similarity	NPD5690	Phase 2
0.8452	Intermediate Similarity	NPD4694	Approved
0.8452	Intermediate Similarity	NPD5280	Approved
0.8452	Intermediate Similarity	NPD6098	Approved
0.8434	Intermediate Similarity	NPD4197	Approved
0.8415	Intermediate Similarity	NPD3667	Approved
0.8315	Intermediate Similarity	NPD5695	Phase 3
0.8293	Intermediate Similarity	NPD4692	Approved
0.8293	Intermediate Similarity	NPD4139	Approved
0.8256	Intermediate Similarity	NPD5737	Approved
0.8256	Intermediate Similarity	NPD6672	Approved
0.8235	Intermediate Similarity	NPD4689	Approved
0.8235	Intermediate Similarity	NPD5279	Phase 3
0.8235	Intermediate Similarity	NPD7521	Approved
0.8235	Intermediate Similarity	NPD6684	Approved
0.8235	Intermediate Similarity	NPD4690	Approved
0.8235	Intermediate Similarity	NPD6409	Approved
0.8235	Intermediate Similarity	NPD4693	Phase 3
0.8235	Intermediate Similarity	NPD4688	Approved
0.8235	Intermediate Similarity	NPD5205	Approved
0.8235	Intermediate Similarity	NPD5330	Approved
0.8235	Intermediate Similarity	NPD7146	Approved
0.8235	Intermediate Similarity	NPD7334	Approved
0.8235	Intermediate Similarity	NPD4138	Approved
0.8214	Intermediate Similarity	NPD3665	Phase 1
0.8214	Intermediate Similarity	NPD3666	Approved
0.8214	Intermediate Similarity	NPD3133	Approved
0.8182	Intermediate Similarity	NPD6050	Approved
0.8161	Intermediate Similarity	NPD6904	Approved
0.8161	Intermediate Similarity	NPD5328	Approved
0.8161	Intermediate Similarity	NPD6673	Approved
0.8161	Intermediate Similarity	NPD6080	Approved
0.8148	Intermediate Similarity	NPD3617	Approved
0.8132	Intermediate Similarity	NPD6083	Phase 2
0.8132	Intermediate Similarity	NPD6084	Phase 2
0.8101	Intermediate Similarity	NPD5733	Approved
0.8068	Intermediate Similarity	NPD5692	Phase 3
0.8068	Intermediate Similarity	NPD5207	Approved
0.8046	Intermediate Similarity	NPD5208	Approved
0.8046	Intermediate Similarity	NPD6903	Approved
0.8046	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD3618	Phase 1
0.7978	Intermediate Similarity	NPD6079	Approved
0.7978	Intermediate Similarity	NPD5694	Approved
0.7955	Intermediate Similarity	NPD4753	Phase 2
0.7955	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD4747	Approved
0.7907	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4687	Approved
0.7865	Intermediate Similarity	NPD4096	Approved
0.7849	Intermediate Similarity	NPD5696	Approved
0.7848	Intermediate Similarity	NPD5276	Approved
0.7848	Intermediate Similarity	NPD4243	Approved
0.7831	Intermediate Similarity	NPD4195	Approved
0.7821	Intermediate Similarity	NPD4137	Phase 3
0.7816	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3668	Phase 3
0.7778	Intermediate Similarity	NPD5693	Phase 1
0.7778	Intermediate Similarity	NPD7515	Phase 2
0.7766	Intermediate Similarity	NPD6404	Discontinued
0.7738	Intermediate Similarity	NPD4695	Discontinued
0.7722	Intermediate Similarity	NPD4691	Approved
0.7717	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4202	Approved
0.7692	Intermediate Similarity	NPD5133	Approved
0.7674	Intermediate Similarity	NPD4788	Approved
0.7662	Intermediate Similarity	NPD4224	Phase 2
0.7654	Intermediate Similarity	NPD4784	Approved
0.7654	Intermediate Similarity	NPD4785	Approved
0.764	Intermediate Similarity	NPD4518	Approved
0.7625	Intermediate Similarity	NPD6081	Approved
0.7614	Intermediate Similarity	NPD4519	Discontinued
0.7614	Intermediate Similarity	NPD4623	Approved
0.7609	Intermediate Similarity	NPD6001	Approved
0.7609	Intermediate Similarity	NPD7748	Approved
0.7561	Intermediate Similarity	NPD7339	Approved
0.7561	Intermediate Similarity	NPD6942	Approved
0.7551	Intermediate Similarity	NPD6675	Approved
0.7551	Intermediate Similarity	NPD6402	Approved
0.7551	Intermediate Similarity	NPD7128	Approved
0.7551	Intermediate Similarity	NPD5739	Approved
0.7527	Intermediate Similarity	NPD5210	Approved
0.7527	Intermediate Similarity	NPD4629	Approved
0.7527	Intermediate Similarity	NPD5654	Approved
0.75	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4697	Phase 3
0.7447	Intermediate Similarity	NPD5221	Approved
0.7447	Intermediate Similarity	NPD7614	Phase 1
0.7447	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5222	Approved
0.7439	Intermediate Similarity	NPD4058	Approved
0.74	Intermediate Similarity	NPD6881	Approved
0.74	Intermediate Similarity	NPD7320	Approved
0.74	Intermediate Similarity	NPD6899	Approved
0.7391	Intermediate Similarity	NPD8034	Phase 2
0.7391	Intermediate Similarity	NPD8035	Phase 2
0.7368	Intermediate Similarity	NPD5959	Approved
0.7368	Intermediate Similarity	NPD7902	Approved
0.7368	Intermediate Similarity	NPD5173	Approved
0.7368	Intermediate Similarity	NPD4755	Approved
0.7349	Intermediate Similarity	NPD5275	Approved
0.7349	Intermediate Similarity	NPD4190	Phase 3
0.7333	Intermediate Similarity	NPD3573	Approved
0.7327	Intermediate Similarity	NPD6373	Approved
0.7327	Intermediate Similarity	NPD6372	Approved
0.73	Intermediate Similarity	NPD5701	Approved
0.73	Intermediate Similarity	NPD5697	Approved
0.7262	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7102	Approved
0.7255	Intermediate Similarity	NPD7290	Approved
0.7255	Intermediate Similarity	NPD6883	Approved
0.725	Intermediate Similarity	NPD5360	Phase 3
0.725	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6011	Approved
0.7216	Intermediate Similarity	NPD5286	Approved
0.7216	Intermediate Similarity	NPD5285	Approved
0.7216	Intermediate Similarity	NPD4700	Approved
0.7216	Intermediate Similarity	NPD4696	Approved
0.7204	Intermediate Similarity	NPD6411	Approved
0.7184	Intermediate Similarity	NPD6649	Approved
0.7184	Intermediate Similarity	NPD6617	Approved
0.7184	Intermediate Similarity	NPD6847	Approved
0.7184	Intermediate Similarity	NPD6650	Approved
0.7184	Intermediate Similarity	NPD8130	Phase 1
0.7184	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6869	Approved
0.7172	Intermediate Similarity	NPD6052	Approved
0.7157	Intermediate Similarity	NPD6012	Approved
0.7157	Intermediate Similarity	NPD6013	Approved
0.7157	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD5223	Approved
0.7126	Intermediate Similarity	NPD7525	Registered
0.7115	Intermediate Similarity	NPD8297	Approved
0.7115	Intermediate Similarity	NPD6882	Approved
0.7113	Intermediate Similarity	NPD7638	Approved
0.7089	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4789	Approved
0.7071	Intermediate Similarity	NPD5211	Phase 2
0.7071	Intermediate Similarity	NPD4633	Approved
0.7071	Intermediate Similarity	NPD5225	Approved
0.7071	Intermediate Similarity	NPD5091	Approved
0.7071	Intermediate Similarity	NPD5226	Approved
0.7071	Intermediate Similarity	NPD5224	Approved
0.7059	Intermediate Similarity	NPD6117	Approved
0.7053	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7900	Approved
0.7041	Intermediate Similarity	NPD7639	Approved
0.7041	Intermediate Similarity	NPD7640	Approved
0.7024	Intermediate Similarity	NPD6924	Approved
0.7024	Intermediate Similarity	NPD6926	Approved
0.7	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD5174	Approved
0.7	Intermediate Similarity	NPD5175	Approved
0.7	Intermediate Similarity	NPD7331	Phase 2
0.6989	Remote Similarity	NPD6051	Approved
0.6989	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6101	Approved
0.6988	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6116	Phase 1
0.6966	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6614	Approved
0.6961	Remote Similarity	NPD6412	Phase 2
0.6941	Remote Similarity	NPD3702	Approved
0.6932	Remote Similarity	NPD5368	Approved
0.6931	Remote Similarity	NPD5141	Approved
0.6916	Remote Similarity	NPD6868	Approved
0.6907	Remote Similarity	NPD7732	Phase 3
0.6897	Remote Similarity	NPD6114	Approved
0.6897	Remote Similarity	NPD6697	Approved
0.6897	Remote Similarity	NPD6115	Approved
0.6897	Remote Similarity	NPD6118	Approved
0.6889	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5362	Discontinued
0.6887	Remote Similarity	NPD4632	Approved
0.6875	Remote Similarity	NPD7341	Phase 2
0.6867	Remote Similarity	NPD4245	Approved
0.6867	Remote Similarity	NPD4244	Approved
0.6863	Remote Similarity	NPD4767	Approved
0.6863	Remote Similarity	NPD4768	Approved
0.6863	Remote Similarity	NPD6008	Approved
0.686	Remote Similarity	NPD6933	Approved
0.6854	Remote Similarity	NPD5369	Approved
0.6852	Remote Similarity	NPD7115	Discovery
0.6789	Remote Similarity	NPD6335	Approved
0.6786	Remote Similarity	NPD4758	Discontinued
0.6786	Remote Similarity	NPD5777	Approved
0.6778	Remote Similarity	NPD4270	Approved
0.6778	Remote Similarity	NPD4269	Approved
0.6778	Remote Similarity	NPD6435	Approved
0.6759	Remote Similarity	NPD6274	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