NPASS Compound

Structure

NPC476282 OpenBabel07101719152D 34 38 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 0.5000 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 1.7321 1.0000 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 -1.5981 -1.2321 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 2.5981 0.5000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 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 2 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 5 29 1 0 0 0 0 7 34 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 22 2 0 0 0 0 10 11 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 20 28 1 0 0 0 0 21 24 2 0 0 0 0 21 31 1 0 0 0 0 22 28 1 0 0 0 0 22 29 1 0 0 0 0 23 26 1 6 0 0 0 23 30 1 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 2 1 1 0 0 0 27 3 1 1 0 0 0 28 4 1 1 0 0 0 29 30 1 1 0 0 0 30 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.31
Volume:	506.632
LogP:	5.869
LogD:	3.712
LogS:	-4.878
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	4.852
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.975
MDCK Permeability:	1.884483208414167e-05
Pgp-inhibitor:	0.708
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.96
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	99.23370361328125%
Volume Distribution (VD):	2.161
Pgp-substrate:	2.476466417312622%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.187
CYP2C9-substrate:	0.438
CYP2D6-inhibitor:	0.48
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	7.793
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.48
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.527
Skin Sensitization:	0.062
Carcinogencity:	0.28
Eye Corrosion:	0.003
Eye Irritation:	0.197
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC476282

Natural Product ID:	NPC476282
*Common Name:**	Pristimerol
IUPAC Name:	methyl (2R,4aS,6aS,6aS,14aS,14bR)-10,11-dihydroxy-2,4a,6a,6a,9,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1H-picene-2-carboxylate
Synonyms:	Pristimerol
Standard InCHIKey:	GAPWCQHXCIXKLV-WXPPGMDDSA-N
Standard InCHI:	InChI=1S/C30H42O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h9,16,23,31-32H,8,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1
SMILES:	COC(=O)[C@]1(C)CC[C@]2([C@@H](C1)[C@]1(C)CC[C@@]3(C(=CCc4c3cc(O)c(c4C)O)[C@]1(CC2)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL56163
PubChem CID:	24861846
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO26894	Kokoona zeylanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678653]
NPO26894	Kokoona zeylanica	Species	Celastraceae	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
Others	2

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		IC50	=	260.0	nM	PMID[559356]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	70.1	%	PMID[559358]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	86.64	%	PMID[559358]

☑ 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 NPC476282 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	310
0.1-0.2	1364
0.2-0.3	2879
0.3-0.4	7073
0.4-0.5	10261
0.5-0.6	10000
0.6-0.7	9663
0.7-0.8	992
0.8-0.85	127
0.85-0.9	21
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9841	High Similarity	NPC243305
0.9333	High Similarity	NPC184935
0.9098	High Similarity	NPC103082
0.8993	High Similarity	NPC470038
0.8963	High Similarity	NPC277559
0.8955	High Similarity	NPC43353
0.8913	High Similarity	NPC469447
0.8913	High Similarity	NPC477873
0.8905	High Similarity	NPC470035
0.8824	High Similarity	NPC49911
0.8824	High Similarity	NPC471152
0.8786	High Similarity	NPC53520
0.875	High Similarity	NPC162935
0.875	High Similarity	NPC249340
0.8741	High Similarity	NPC293454
0.8732	High Similarity	NPC10842
0.8682	High Similarity	NPC121168
0.8681	High Similarity	NPC470037
0.8594	High Similarity	NPC478121
0.8592	High Similarity	NPC8102
0.8592	High Similarity	NPC66894
0.8582	High Similarity	NPC477207
0.8582	High Similarity	NPC199936
0.855	High Similarity	NPC15127
0.8527	High Similarity	NPC241001
0.8519	High Similarity	NPC291001
0.8516	High Similarity	NPC42657
0.8504	High Similarity	NPC16030
0.85	High Similarity	NPC304110
0.85	High Similarity	NPC27518
0.8489	Intermediate Similarity	NPC182249
0.8462	Intermediate Similarity	NPC75295
0.8462	Intermediate Similarity	NPC258856
0.8462	Intermediate Similarity	NPC253627
0.8429	Intermediate Similarity	NPC155192
0.8429	Intermediate Similarity	NPC271494
0.8429	Intermediate Similarity	NPC473591
0.8425	Intermediate Similarity	NPC475311
0.8425	Intermediate Similarity	NPC475454
0.8425	Intermediate Similarity	NPC118033
0.8425	Intermediate Similarity	NPC473680
0.8425	Intermediate Similarity	NPC473579
0.8406	Intermediate Similarity	NPC173569
0.8406	Intermediate Similarity	NPC279463
0.8406	Intermediate Similarity	NPC477874
0.8406	Intermediate Similarity	NPC472804
0.8403	Intermediate Similarity	NPC474991
0.8397	Intermediate Similarity	NPC11250
0.8394	Intermediate Similarity	NPC475457
0.8394	Intermediate Similarity	NPC18982
0.8394	Intermediate Similarity	NPC475627
0.8394	Intermediate Similarity	NPC49742
0.8394	Intermediate Similarity	NPC475346
0.8392	Intermediate Similarity	NPC126707
0.8385	Intermediate Similarity	NPC259703
0.8385	Intermediate Similarity	NPC32322
0.8369	Intermediate Similarity	NPC3218
0.8367	Intermediate Similarity	NPC475579
0.8367	Intermediate Similarity	NPC473773
0.8356	Intermediate Similarity	NPC142654
0.8345	Intermediate Similarity	NPC470757
0.8345	Intermediate Similarity	NPC249817
0.8344	Intermediate Similarity	NPC185617
0.8333	Intermediate Similarity	NPC198014
0.8333	Intermediate Similarity	NPC84786
0.8333	Intermediate Similarity	NPC471187
0.8322	Intermediate Similarity	NPC25491
0.8321	Intermediate Similarity	NPC154696
0.831	Intermediate Similarity	NPC2681
0.831	Intermediate Similarity	NPC272907
0.8288	Intermediate Similarity	NPC477206
0.8286	Intermediate Similarity	NPC198621
0.8286	Intermediate Similarity	NPC216940
0.8286	Intermediate Similarity	NPC22676
0.8286	Intermediate Similarity	NPC475482
0.8276	Intermediate Similarity	NPC191899
0.8276	Intermediate Similarity	NPC58752
0.8276	Intermediate Similarity	NPC246229
0.8271	Intermediate Similarity	NPC181334
0.8261	Intermediate Similarity	NPC111845
0.8261	Intermediate Similarity	NPC138472
0.8258	Intermediate Similarity	NPC471794
0.8258	Intermediate Similarity	NPC478058
0.8252	Intermediate Similarity	NPC235557
0.8248	Intermediate Similarity	NPC258073
0.8244	Intermediate Similarity	NPC164852
0.8239	Intermediate Similarity	NPC473612
0.8231	Intermediate Similarity	NPC93071
0.8219	Intermediate Similarity	NPC127046
0.8209	Intermediate Similarity	NPC137750
0.8209	Intermediate Similarity	NPC87985
0.8194	Intermediate Similarity	NPC26045
0.8188	Intermediate Similarity	NPC105942
0.8188	Intermediate Similarity	NPC205392
0.8182	Intermediate Similarity	NPC35212
0.8148	Intermediate Similarity	NPC71610
0.8143	Intermediate Similarity	NPC153088
0.8143	Intermediate Similarity	NPC252343
0.814	Intermediate Similarity	NPC471668
0.8138	Intermediate Similarity	NPC307205
0.8125	Intermediate Similarity	NPC310621
0.8125	Intermediate Similarity	NPC252133
0.8121	Intermediate Similarity	NPC124842
0.812	Intermediate Similarity	NPC176208
0.8116	Intermediate Similarity	NPC18798
0.8112	Intermediate Similarity	NPC29599
0.8112	Intermediate Similarity	NPC472801
0.8112	Intermediate Similarity	NPC471853
0.8112	Intermediate Similarity	NPC172311
0.8112	Intermediate Similarity	NPC476534
0.8102	Intermediate Similarity	NPC131684
0.8099	Intermediate Similarity	NPC469680
0.8099	Intermediate Similarity	NPC230811
0.8099	Intermediate Similarity	NPC471974
0.8099	Intermediate Similarity	NPC469681
0.8099	Intermediate Similarity	NPC234548
0.8099	Intermediate Similarity	NPC248287
0.8092	Intermediate Similarity	NPC126002
0.8088	Intermediate Similarity	NPC476536
0.8074	Intermediate Similarity	NPC137416
0.8071	Intermediate Similarity	NPC27394
0.8047	Intermediate Similarity	NPC148969
0.8047	Intermediate Similarity	NPC317869
0.8042	Intermediate Similarity	NPC79372
0.803	Intermediate Similarity	NPC190501
0.803	Intermediate Similarity	NPC318552
0.8029	Intermediate Similarity	NPC201069
0.8013	Intermediate Similarity	NPC62051
0.8	Intermediate Similarity	NPC248068
0.8	Intermediate Similarity	NPC4170
0.8	Intermediate Similarity	NPC471927
0.7986	Intermediate Similarity	NPC312341
0.7984	Intermediate Similarity	NPC268160
0.7972	Intermediate Similarity	NPC132723
0.7972	Intermediate Similarity	NPC265335
0.7972	Intermediate Similarity	NPC116742
0.7972	Intermediate Similarity	NPC139243
0.7972	Intermediate Similarity	NPC76032
0.7971	Intermediate Similarity	NPC117899
0.7971	Intermediate Similarity	NPC86257
0.7969	Intermediate Similarity	NPC471179
0.7958	Intermediate Similarity	NPC7464
0.7956	Intermediate Similarity	NPC69424
0.7956	Intermediate Similarity	NPC78364
0.7956	Intermediate Similarity	NPC176130
0.7956	Intermediate Similarity	NPC84672
0.7956	Intermediate Similarity	NPC72667
0.7953	Intermediate Similarity	NPC141782
0.7945	Intermediate Similarity	NPC474599
0.7943	Intermediate Similarity	NPC213122
0.7943	Intermediate Similarity	NPC471913
0.7935	Intermediate Similarity	NPC266365
0.7929	Intermediate Similarity	NPC165612
0.7923	Intermediate Similarity	NPC147179
0.7923	Intermediate Similarity	NPC35797
0.7923	Intermediate Similarity	NPC192948
0.7919	Intermediate Similarity	NPC471852
0.7917	Intermediate Similarity	NPC470617
0.7917	Intermediate Similarity	NPC470616
0.7917	Intermediate Similarity	NPC471875
0.791	Intermediate Similarity	NPC474115
0.791	Intermediate Similarity	NPC472271
0.7899	Intermediate Similarity	NPC229894
0.7899	Intermediate Similarity	NPC193203
0.7895	Intermediate Similarity	NPC260832
0.7895	Intermediate Similarity	NPC135467
0.7891	Intermediate Similarity	NPC309169
0.7891	Intermediate Similarity	NPC196941
0.7891	Intermediate Similarity	NPC260323
0.7891	Intermediate Similarity	NPC176279
0.7883	Intermediate Similarity	NPC254492
0.7879	Intermediate Similarity	NPC328694
0.7877	Intermediate Similarity	NPC477209
0.7868	Intermediate Similarity	NPC199273
0.7868	Intermediate Similarity	NPC265413
0.7868	Intermediate Similarity	NPC10154
0.7867	Intermediate Similarity	NPC470618
0.7867	Intermediate Similarity	NPC327962
0.7867	Intermediate Similarity	NPC470619
0.7867	Intermediate Similarity	NPC208785
0.7867	Intermediate Similarity	NPC145527
0.7863	Intermediate Similarity	NPC308828
0.7863	Intermediate Similarity	NPC308311
0.7863	Intermediate Similarity	NPC477137
0.7863	Intermediate Similarity	NPC219112
0.7863	Intermediate Similarity	NPC38893
0.7857	Intermediate Similarity	NPC471851
0.7852	Intermediate Similarity	NPC52692
0.7852	Intermediate Similarity	NPC321402
0.7847	Intermediate Similarity	NPC114333
0.7847	Intermediate Similarity	NPC289358
0.7847	Intermediate Similarity	NPC477849
0.7847	Intermediate Similarity	NPC50615
0.7847	Intermediate Similarity	NPC469857
0.7847	Intermediate Similarity	NPC5014
0.7847	Intermediate Similarity	NPC51531
0.7847	Intermediate Similarity	NPC91887
0.7847	Intermediate Similarity	NPC42384
0.7847	Intermediate Similarity	NPC245760
0.7847	Intermediate Similarity	NPC157284

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 NPC476282 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	874
0.2-0.3	1533
0.3-0.4	2785
0.4-0.5	2119
0.5-0.6	1162
0.6-0.7	382
0.7-0.8	25
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8841	High Similarity	NPD8166	Discontinued
0.8116	Intermediate Similarity	NPD6663	Approved
0.8088	Intermediate Similarity	NPD5736	Approved
0.803	Intermediate Similarity	NPD2932	Approved
0.803	Intermediate Similarity	NPD3019	Approved
0.7838	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD7003	Approved
0.7597	Intermediate Similarity	NPD3021	Approved
0.7597	Intermediate Similarity	NPD3022	Approved
0.7574	Intermediate Similarity	NPD3023	Approved
0.7574	Intermediate Similarity	NPD3026	Approved
0.7556	Intermediate Similarity	NPD3025	Approved
0.7556	Intermediate Similarity	NPD3024	Approved
0.7534	Intermediate Similarity	NPD5408	Approved
0.7534	Intermediate Similarity	NPD5404	Approved
0.7534	Intermediate Similarity	NPD5405	Approved
0.7534	Intermediate Similarity	NPD5406	Approved
0.7516	Intermediate Similarity	NPD7458	Discontinued
0.7482	Intermediate Similarity	NPD1283	Approved
0.7431	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3620	Phase 2
0.7431	Intermediate Similarity	NPD4060	Phase 1
0.7391	Intermediate Similarity	NPD3092	Approved
0.7362	Intermediate Similarity	NPD7228	Approved
0.7361	Intermediate Similarity	NPD8032	Phase 2
0.7358	Intermediate Similarity	NPD6234	Discontinued
0.7353	Intermediate Similarity	NPD3091	Approved
0.7305	Intermediate Similarity	NPD3094	Phase 2
0.7267	Intermediate Similarity	NPD8127	Discontinued
0.7266	Intermediate Similarity	NPD1281	Approved
0.7261	Intermediate Similarity	NPD37	Approved
0.7246	Intermediate Similarity	NPD4626	Approved
0.723	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7095	Approved
0.7219	Intermediate Similarity	NPD4110	Phase 3
0.7219	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6273	Approved
0.7195	Intermediate Similarity	NPD7473	Discontinued
0.7193	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD825	Approved
0.7192	Intermediate Similarity	NPD826	Approved
0.719	Intermediate Similarity	NPD7390	Discontinued
0.7164	Intermediate Similarity	NPD7635	Approved
0.7143	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD1201	Approved
0.7134	Intermediate Similarity	NPD7028	Phase 2
0.7133	Intermediate Similarity	NPD257	Approved
0.7133	Intermediate Similarity	NPD258	Approved
0.7125	Intermediate Similarity	NPD4967	Phase 2
0.7125	Intermediate Similarity	NPD4966	Approved
0.7125	Intermediate Similarity	NPD4965	Approved
0.7122	Intermediate Similarity	NPD3095	Discontinued
0.7122	Intermediate Similarity	NPD4059	Approved
0.7117	Intermediate Similarity	NPD6232	Discontinued
0.7111	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2979	Phase 3
0.7075	Intermediate Similarity	NPD4140	Approved
0.7067	Intermediate Similarity	NPD2935	Discontinued
0.7063	Intermediate Similarity	NPD1470	Approved
0.7059	Intermediate Similarity	NPD5951	Approved
0.7059	Intermediate Similarity	NPD2629	Approved
0.7059	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.705	Intermediate Similarity	NPD1651	Approved
0.7045	Intermediate Similarity	NPD2342	Discontinued
0.7042	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3300	Phase 2
0.7007	Intermediate Similarity	NPD259	Phase 1
0.7	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6099	Approved
0.6954	Remote Similarity	NPD6100	Approved
0.6954	Remote Similarity	NPD2438	Suspended
0.6948	Remote Similarity	NPD6190	Approved
0.6939	Remote Similarity	NPD3764	Approved
0.6933	Remote Similarity	NPD7097	Phase 1
0.6929	Remote Similarity	NPD5691	Approved
0.6929	Remote Similarity	NPD1809	Phase 2
0.6929	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6674	Discontinued
0.6923	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD555	Phase 2
0.6908	Remote Similarity	NPD7266	Discontinued
0.6905	Remote Similarity	NPD5844	Phase 1
0.6901	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3020	Approved
0.6882	Remote Similarity	NPD7240	Approved
0.6871	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7008	Discontinued
0.6867	Remote Similarity	NPD4097	Suspended
0.6866	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD9569	Approved
0.6848	Remote Similarity	NPD7199	Phase 2
0.6846	Remote Similarity	NPD943	Approved
0.6842	Remote Similarity	NPD2531	Phase 2
0.6842	Remote Similarity	NPD4477	Approved
0.6842	Remote Similarity	NPD4476	Approved
0.6838	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1164	Approved
0.6828	Remote Similarity	NPD2797	Approved
0.6821	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4750	Phase 3
0.6815	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.68	Remote Similarity	NPD275	Approved
0.68	Remote Similarity	NPD230	Phase 1
0.68	Remote Similarity	NPD5735	Approved
0.68	Remote Similarity	NPD274	Approved
0.6797	Remote Similarity	NPD5762	Approved
0.6797	Remote Similarity	NPD5763	Approved
0.6797	Remote Similarity	NPD2346	Discontinued
0.679	Remote Similarity	NPD8455	Phase 2
0.679	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1465	Phase 2
0.6782	Remote Similarity	NPD8150	Discontinued
0.6781	Remote Similarity	NPD4624	Approved
0.6776	Remote Similarity	NPD2799	Discontinued
0.6774	Remote Similarity	NPD4628	Phase 3
0.6774	Remote Similarity	NPD3750	Approved
0.6766	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4198	Discontinued
0.6757	Remote Similarity	NPD9537	Phase 1
0.6757	Remote Similarity	NPD9536	Phase 1
0.6753	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2420	Approved
0.6752	Remote Similarity	NPD2421	Approved
0.6747	Remote Similarity	NPD6959	Discontinued
0.6744	Remote Similarity	NPD288	Approved
0.6739	Remote Similarity	NPD5283	Phase 1
0.6739	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD9269	Phase 2
0.673	Remote Similarity	NPD7427	Discontinued
0.6719	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD228	Approved
0.6714	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7985	Registered
0.6711	Remote Similarity	NPD3268	Approved
0.671	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3645	Discontinued
0.6707	Remote Similarity	NPD7768	Phase 2
0.6705	Remote Similarity	NPD8312	Approved
0.6705	Remote Similarity	NPD8313	Approved
0.669	Remote Similarity	NPD5327	Phase 3
0.669	Remote Similarity	NPD4093	Discontinued
0.6689	Remote Similarity	NPD2605	Approved
0.6689	Remote Similarity	NPD3657	Discovery
0.6689	Remote Similarity	NPD2606	Approved
0.6687	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD6873	Phase 2
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6677	Suspended
0.6667	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD844	Approved
0.6646	Remote Similarity	NPD3455	Phase 2
0.6646	Remote Similarity	NPD3226	Approved
0.6645	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5155	Approved
0.6644	Remote Similarity	NPD6696	Suspended
0.6644	Remote Similarity	NPD5156	Approved
0.6643	Remote Similarity	NPD1778	Approved
0.6643	Remote Similarity	NPD2286	Discontinued
0.6643	Remote Similarity	NPD1751	Approved
0.6641	Remote Similarity	NPD845	Approved
0.6628	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1608	Approved
0.6607	Remote Similarity	NPD7229	Phase 3
0.6604	Remote Similarity	NPD2532	Approved
0.6604	Remote Similarity	NPD2533	Approved
0.6604	Remote Similarity	NPD2534	Approved
0.66	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3847	Discontinued
0.6596	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD2933	Approved
0.6589	Remote Similarity	NPD2934	Approved
0.6582	Remote Similarity	NPD7236	Approved
0.6581	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3594	Approved
0.6577	Remote Similarity	NPD3595	Approved
0.6573	Remote Similarity	NPD2490	Approved
0.6573	Remote Similarity	NPD5585	Approved
0.6573	Remote Similarity	NPD2488	Approved
0.6568	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3400	Discontinued
0.6558	Remote Similarity	NPD7743	Approved
0.6558	Remote Similarity	NPD7742	Approved
0.6556	Remote Similarity	NPD4248	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data