NPASS Compound

Structure

NPC267242 OpenBabel07101718292D 31 34 0 0 1 0 0 0 0 0999 V2000 0.8413 -3.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1960 -0.0377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3651 -1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3651 -1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5238 -4.3714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3364 1.8930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 -2.9143 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2458 0.1643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5238 -1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5238 -1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5238 -3.4000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8506 1.0517 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8413 -1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 -1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5238 -0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 -0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 -1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5238 -0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 -1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8413 -0.4857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3651 -2.9143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3651 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 -2.9143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7165 0.1015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 1.4571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8845 0.9502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 7 29 1 0 0 0 0 8 16 1 0 0 0 0 8 17 2 0 0 0 0 9 18 2 0 0 0 0 9 19 1 0 0 0 0 10 1 1 1 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 2 1 6 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 20 2 0 0 0 0 13 21 2 0 0 0 0 13 22 1 0 0 0 0 14 5 1 6 0 0 0 14 25 1 0 0 0 0 15 6 1 1 0 0 0 15 30 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 19 31 1 0 0 0 0 21 23 1 0 0 0 0 22 27 2 0 0 0 0 23 24 1 1 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 29 1 1 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.2
Volume:	435.147
LogP:	3.251
LogD:	2.521
LogS:	-3.861
# Rotatable Bonds:	2
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	5.549
Fsp3:	0.542
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.361
MDCK Permeability:	5.363241143641062e-06
Pgp-inhibitor:	0.087
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.818

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	90.93306732177734%
Volume Distribution (VD):	1.52
Pgp-substrate:	5.98648738861084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.928
CYP1A2-substrate:	0.587
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.121
CYP3A4-substrate:	0.656

ADMET: Excretion

Clearance (CL):	7.351
Half-life (T1/2):	0.694

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.646
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.494
Rat Oral Acute Toxicity:	0.418
Maximum Recommended Daily Dose:	0.474
Skin Sensitization:	0.136
Carcinogencity:	0.161
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC267242

Natural Product ID:	NPC267242
*Common Name:**	Penicitrinol G
IUPAC Name:	(2R,3S,11aR,11bR)-9,11b-dihydroxy-7-[(2S,3R)-3-hydroxybutan-2-yl]-11a-methoxy-2,3,4,8-tetramethyl-2,3-dihydrofuro[3,2-c]xanthen-5-one
Synonyms:	Penicitrinol G
Standard InCHIKey:	LGUTZFLPGGSLQR-QITNJACESA-N
Standard InCHI:	InChI=1S/C24H30O7/c1-10(14(5)25)20-12(3)18(26)9-19-16(20)8-17-22(27)13(4)21-11(2)15(6)30-23(21,28)24(17,29-7)31-19/h8-11,14-15,25-26,28H,1-7H3/t10-,11-,14-,15-,23-,24-/m1/s1
SMILES:	C[C@H]([C@@H](C)O)c1c(C)c(cc2c1C=C1C(=O)C(=C3[C@H](C)[C@@H](C)O[C@]3([C@]1(OC)O2)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1822985
PubChem CID:	53466283
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO33186	penicillium citrinum hgy1-5	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21761866]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[503802]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[503802]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[503802]

☑ 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 NPC267242 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	366
0.1-0.2	1331
0.2-0.3	2947
0.3-0.4	6465
0.4-0.5	11095
0.5-0.6	5387
0.6-0.7	5830
0.7-0.8	8658
0.8-0.85	600
0.85-0.9	14
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC60084
0.9156	High Similarity	NPC164244
0.878	High Similarity	NPC98776
0.8734	High Similarity	NPC470606
0.8679	High Similarity	NPC470607
0.8675	High Similarity	NPC475233
0.8659	High Similarity	NPC313717
0.8659	High Similarity	NPC315306
0.8634	High Similarity	NPC472402
0.8625	High Similarity	NPC470810
0.8623	High Similarity	NPC5671
0.8608	High Similarity	NPC470603
0.8608	High Similarity	NPC470604
0.8608	High Similarity	NPC470605
0.8606	High Similarity	NPC111536
0.8606	High Similarity	NPC5029
0.8606	High Similarity	NPC271385
0.8606	High Similarity	NPC76128
0.8606	High Similarity	NPC30432
0.8599	High Similarity	NPC470340
0.8598	High Similarity	NPC259905
0.859	High Similarity	NPC179178
0.8589	High Similarity	NPC178851
0.858	High Similarity	NPC471286
0.8571	High Similarity	NPC117985
0.8553	High Similarity	NPC17521
0.8544	High Similarity	NPC211158
0.8544	High Similarity	NPC78021
0.8544	High Similarity	NPC87304
0.8544	High Similarity	NPC268950
0.8544	High Similarity	NPC108706
0.8526	High Similarity	NPC139966
0.8526	High Similarity	NPC307052
0.8516	High Similarity	NPC202494
0.8506	High Similarity	NPC297788
0.8506	High Similarity	NPC212697
0.8503	High Similarity	NPC68381
0.8494	Intermediate Similarity	NPC472620
0.8485	Intermediate Similarity	NPC222455
0.8485	Intermediate Similarity	NPC473202
0.8485	Intermediate Similarity	NPC191653
0.8481	Intermediate Similarity	NPC327269
0.8481	Intermediate Similarity	NPC285623
0.8481	Intermediate Similarity	NPC31627
0.8481	Intermediate Similarity	NPC256141
0.8481	Intermediate Similarity	NPC180944
0.8481	Intermediate Similarity	NPC476238
0.8466	Intermediate Similarity	NPC469518
0.8466	Intermediate Similarity	NPC469475
0.8462	Intermediate Similarity	NPC10097
0.8457	Intermediate Similarity	NPC478222
0.8457	Intermediate Similarity	NPC74854
0.8457	Intermediate Similarity	NPC45124
0.8457	Intermediate Similarity	NPC30655
0.8452	Intermediate Similarity	NPC475246
0.8452	Intermediate Similarity	NPC46958
0.8447	Intermediate Similarity	NPC218818
0.8447	Intermediate Similarity	NPC4950
0.8447	Intermediate Similarity	NPC279732
0.8447	Intermediate Similarity	NPC470339
0.8443	Intermediate Similarity	NPC213052
0.8438	Intermediate Similarity	NPC472050
0.8438	Intermediate Similarity	NPC164427
0.8434	Intermediate Similarity	NPC298778
0.8428	Intermediate Similarity	NPC469405
0.8428	Intermediate Similarity	NPC155686
0.8428	Intermediate Similarity	NPC303950
0.8418	Intermediate Similarity	NPC474772
0.8418	Intermediate Similarity	NPC472423
0.8418	Intermediate Similarity	NPC474744
0.8418	Intermediate Similarity	NPC132990
0.8418	Intermediate Similarity	NPC46882
0.8418	Intermediate Similarity	NPC134819
0.8418	Intermediate Similarity	NPC190217
0.8418	Intermediate Similarity	NPC471675
0.8418	Intermediate Similarity	NPC240768
0.8418	Intermediate Similarity	NPC200773
0.8415	Intermediate Similarity	NPC316262
0.8415	Intermediate Similarity	NPC326520
0.8415	Intermediate Similarity	NPC314653
0.8415	Intermediate Similarity	NPC294722
0.8412	Intermediate Similarity	NPC170203
0.8408	Intermediate Similarity	NPC317492
0.8405	Intermediate Similarity	NPC215612
0.8405	Intermediate Similarity	NPC473961
0.8405	Intermediate Similarity	NPC125991
0.8405	Intermediate Similarity	NPC81679
0.8397	Intermediate Similarity	NPC470670
0.8397	Intermediate Similarity	NPC47388
0.8397	Intermediate Similarity	NPC85773
0.8397	Intermediate Similarity	NPC473133
0.8395	Intermediate Similarity	NPC328102
0.8395	Intermediate Similarity	NPC306978
0.8395	Intermediate Similarity	NPC472055
0.8395	Intermediate Similarity	NPC470358
0.8395	Intermediate Similarity	NPC313368
0.8393	Intermediate Similarity	NPC199533
0.8393	Intermediate Similarity	NPC294149
0.8393	Intermediate Similarity	NPC3718
0.8393	Intermediate Similarity	NPC474345
0.8393	Intermediate Similarity	NPC470454
0.8385	Intermediate Similarity	NPC220462
0.8385	Intermediate Similarity	NPC246466
0.8385	Intermediate Similarity	NPC177742
0.8385	Intermediate Similarity	NPC23817
0.8385	Intermediate Similarity	NPC158542
0.8383	Intermediate Similarity	NPC223375
0.8383	Intermediate Similarity	NPC475825
0.8377	Intermediate Similarity	NPC130206
0.8373	Intermediate Similarity	NPC472619
0.8365	Intermediate Similarity	NPC473996
0.8365	Intermediate Similarity	NPC275878
0.8365	Intermediate Similarity	NPC51824
0.8365	Intermediate Similarity	NPC268992
0.8365	Intermediate Similarity	NPC470338
0.8365	Intermediate Similarity	NPC113608
0.8365	Intermediate Similarity	NPC470337
0.8364	Intermediate Similarity	NPC207575
0.8364	Intermediate Similarity	NPC472452
0.8364	Intermediate Similarity	NPC13481
0.8364	Intermediate Similarity	NPC178173
0.8364	Intermediate Similarity	NPC53640
0.8364	Intermediate Similarity	NPC170245
0.8354	Intermediate Similarity	NPC18100
0.8354	Intermediate Similarity	NPC477240
0.8354	Intermediate Similarity	NPC180351
0.8354	Intermediate Similarity	NPC205265
0.8354	Intermediate Similarity	NPC472281
0.8354	Intermediate Similarity	NPC124038
0.8354	Intermediate Similarity	NPC472421
0.8354	Intermediate Similarity	NPC100849
0.8354	Intermediate Similarity	NPC38775
0.8354	Intermediate Similarity	NPC106025
0.8354	Intermediate Similarity	NPC214454
0.8354	Intermediate Similarity	NPC225854
0.8354	Intermediate Similarity	NPC191154
0.8354	Intermediate Similarity	NPC470908
0.8354	Intermediate Similarity	NPC91288
0.8353	Intermediate Similarity	NPC299149
0.8353	Intermediate Similarity	NPC212290
0.8353	Intermediate Similarity	NPC277710
0.8353	Intermediate Similarity	NPC114257
0.8353	Intermediate Similarity	NPC153578
0.8344	Intermediate Similarity	NPC191634
0.8344	Intermediate Similarity	NPC168085
0.8344	Intermediate Similarity	NPC94155
0.8344	Intermediate Similarity	NPC92589
0.8344	Intermediate Similarity	NPC65746
0.8344	Intermediate Similarity	NPC309452
0.8344	Intermediate Similarity	NPC96031
0.8343	Intermediate Similarity	NPC312630
0.8343	Intermediate Similarity	NPC324220
0.8333	Intermediate Similarity	NPC186113
0.8333	Intermediate Similarity	NPC73511
0.8333	Intermediate Similarity	NPC239118
0.8333	Intermediate Similarity	NPC474302
0.8333	Intermediate Similarity	NPC125969
0.8323	Intermediate Similarity	NPC241874
0.8323	Intermediate Similarity	NPC212748
0.8323	Intermediate Similarity	NPC78492
0.8323	Intermediate Similarity	NPC477573
0.8323	Intermediate Similarity	NPC208152
0.8323	Intermediate Similarity	NPC477571
0.8323	Intermediate Similarity	NPC78554
0.8323	Intermediate Similarity	NPC474738
0.8323	Intermediate Similarity	NPC321372
0.8323	Intermediate Similarity	NPC474609
0.8323	Intermediate Similarity	NPC469936
0.8323	Intermediate Similarity	NPC478223
0.8323	Intermediate Similarity	NPC477572
0.8323	Intermediate Similarity	NPC109967
0.8323	Intermediate Similarity	NPC261866
0.8323	Intermediate Similarity	NPC129053
0.8323	Intermediate Similarity	NPC475797
0.8322	Intermediate Similarity	NPC177712
0.8322	Intermediate Similarity	NPC24913
0.8313	Intermediate Similarity	NPC472583
0.8313	Intermediate Similarity	NPC135522
0.8313	Intermediate Similarity	NPC192189
0.8313	Intermediate Similarity	NPC470331
0.8313	Intermediate Similarity	NPC7989
0.8313	Intermediate Similarity	NPC223701
0.8312	Intermediate Similarity	NPC171870
0.8304	Intermediate Similarity	NPC475161
0.8304	Intermediate Similarity	NPC6709
0.8304	Intermediate Similarity	NPC477860
0.8303	Intermediate Similarity	NPC475738
0.8303	Intermediate Similarity	NPC7752
0.8303	Intermediate Similarity	NPC475979
0.8303	Intermediate Similarity	NPC472277
0.8303	Intermediate Similarity	NPC473286
0.8302	Intermediate Similarity	NPC472420
0.8302	Intermediate Similarity	NPC70016
0.8302	Intermediate Similarity	NPC471676
0.8302	Intermediate Similarity	NPC215921
0.8302	Intermediate Similarity	NPC472580
0.8302	Intermediate Similarity	NPC46564
0.8302	Intermediate Similarity	NPC263384
0.8302	Intermediate Similarity	NPC472636
0.8302	Intermediate Similarity	NPC318424

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 NPC267242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	843
0.2-0.3	1909
0.3-0.4	2529
0.4-0.5	1966
0.5-0.6	1007
0.6-0.7	422
0.7-0.8	150
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8424	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD6559	Discontinued
0.8272	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD37	Approved
0.8221	Intermediate Similarity	NPD6234	Discontinued
0.821	Intermediate Similarity	NPD4965	Approved
0.821	Intermediate Similarity	NPD4967	Phase 2
0.821	Intermediate Similarity	NPD4966	Approved
0.8125	Intermediate Similarity	NPD4380	Phase 2
0.8086	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2533	Approved
0.8038	Intermediate Similarity	NPD2534	Approved
0.8038	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD6801	Discontinued
0.7988	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD3751	Discontinued
0.7975	Intermediate Similarity	NPD7819	Suspended
0.7952	Intermediate Similarity	NPD5494	Approved
0.7949	Intermediate Similarity	NPD2800	Approved
0.7941	Intermediate Similarity	NPD7054	Approved
0.7939	Intermediate Similarity	NPD7075	Discontinued
0.7925	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1934	Approved
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7904	Intermediate Similarity	NPD7199	Phase 2
0.7898	Intermediate Similarity	NPD3750	Approved
0.7898	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7074	Phase 3
0.7895	Intermediate Similarity	NPD7472	Approved
0.7885	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD3882	Suspended
0.7866	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD2801	Approved
0.7849	Intermediate Similarity	NPD6797	Phase 2
0.7818	Intermediate Similarity	NPD5402	Approved
0.7816	Intermediate Similarity	NPD8312	Approved
0.7816	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD7251	Discontinued
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7808	Phase 3
0.7759	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD3787	Discontinued
0.7733	Intermediate Similarity	NPD5844	Phase 1
0.7719	Intermediate Similarity	NPD7473	Discontinued
0.7711	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1653	Approved
0.7661	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6166	Phase 2
0.7658	Intermediate Similarity	NPD1549	Phase 2
0.7647	Intermediate Similarity	NPD6232	Discontinued
0.7643	Intermediate Similarity	NPD2796	Approved
0.764	Intermediate Similarity	NPD1511	Approved
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5403	Approved
0.7607	Intermediate Similarity	NPD920	Approved
0.7605	Intermediate Similarity	NPD3817	Phase 2
0.76	Intermediate Similarity	NPD7240	Approved
0.7595	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3748	Approved
0.758	Intermediate Similarity	NPD1510	Phase 2
0.756	Intermediate Similarity	NPD7768	Phase 2
0.7546	Intermediate Similarity	NPD1512	Approved
0.7545	Intermediate Similarity	NPD1465	Phase 2
0.7544	Intermediate Similarity	NPD7229	Phase 3
0.7532	Intermediate Similarity	NPD6100	Approved
0.7532	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6099	Approved
0.7531	Intermediate Similarity	NPD6799	Approved
0.753	Intermediate Similarity	NPD7411	Suspended
0.7528	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5401	Approved
0.747	Intermediate Similarity	NPD6599	Discontinued
0.7443	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5710	Approved
0.7442	Intermediate Similarity	NPD5711	Approved
0.7438	Intermediate Similarity	NPD2424	Discontinued
0.7436	Intermediate Similarity	NPD1613	Approved
0.7436	Intermediate Similarity	NPD4060	Phase 1
0.7436	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2935	Discontinued
0.7419	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3226	Approved
0.7391	Intermediate Similarity	NPD6674	Discontinued
0.7391	Intermediate Similarity	NPD1243	Approved
0.7389	Intermediate Similarity	NPD8434	Phase 2
0.7384	Intermediate Similarity	NPD1247	Approved
0.7378	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6005	Phase 3
0.7375	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6002	Phase 3
0.7375	Intermediate Similarity	NPD6004	Phase 3
0.7375	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7368	Intermediate Similarity	NPD919	Approved
0.736	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2799	Discontinued
0.7356	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4628	Phase 3
0.7342	Intermediate Similarity	NPD6651	Approved
0.7337	Intermediate Similarity	NPD8455	Phase 2
0.7326	Intermediate Similarity	NPD6776	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD6780	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7326	Intermediate Similarity	NPD6779	Approved
0.7325	Intermediate Similarity	NPD1240	Approved
0.7321	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4749	Approved
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD4908	Phase 1
0.7289	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1652	Phase 2
0.7284	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6355	Discontinued
0.7256	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7033	Discontinued
0.725	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6823	Phase 2
0.7244	Intermediate Similarity	NPD4625	Phase 3
0.7244	Intermediate Similarity	NPD3027	Phase 3
0.7233	Intermediate Similarity	NPD1607	Approved
0.7226	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7208	Intermediate Similarity	NPD2797	Approved
0.7205	Intermediate Similarity	NPD1551	Phase 2
0.7197	Intermediate Similarity	NPD2313	Discontinued
0.7197	Intermediate Similarity	NPD3268	Approved
0.7184	Intermediate Similarity	NPD8127	Discontinued
0.7181	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1610	Phase 2
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7171	Intermediate Similarity	NPD1091	Approved
0.717	Intermediate Similarity	NPD230	Phase 1
0.7169	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2798	Approved
0.7161	Intermediate Similarity	NPD5647	Approved
0.7161	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5762	Approved
0.716	Intermediate Similarity	NPD5763	Approved
0.7135	Intermediate Similarity	NPD7286	Phase 2
0.7126	Intermediate Similarity	NPD6273	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7698	Approved
0.7115	Intermediate Similarity	NPD2861	Phase 2
0.7111	Intermediate Similarity	NPD7685	Pre-registration
0.7104	Intermediate Similarity	NPD8150	Discontinued
0.7102	Intermediate Similarity	NPD3926	Phase 2
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7098	Intermediate Similarity	NPD7584	Approved
0.7089	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD7871	Phase 2
0.7083	Intermediate Similarity	NPD7870	Phase 2
0.7063	Intermediate Similarity	NPD447	Suspended
0.7062	Intermediate Similarity	NPD2403	Approved
0.7062	Intermediate Similarity	NPD7701	Phase 2
0.7059	Intermediate Similarity	NPD6535	Approved
0.7059	Intermediate Similarity	NPD7028	Phase 2
0.7059	Intermediate Similarity	NPD6534	Approved
0.7059	Intermediate Similarity	NPD3705	Approved
0.7056	Intermediate Similarity	NPD5953	Discontinued
0.7055	Intermediate Similarity	NPD2344	Approved
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5058	Phase 3
0.7041	Intermediate Similarity	NPD7783	Phase 2
0.7041	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7801	Approved
0.7035	Intermediate Similarity	NPD5760	Phase 2
0.7035	Intermediate Similarity	NPD5761	Phase 2
0.7032	Intermediate Similarity	NPD8651	Approved
0.7032	Intermediate Similarity	NPD6696	Suspended
0.7031	Intermediate Similarity	NPD7680	Approved
0.702	Intermediate Similarity	NPD1548	Phase 1
0.7019	Intermediate Similarity	NPD6653	Approved
0.7017	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7390	Discontinued
0.6994	Remote Similarity	NPD4288	Approved
0.699	Remote Similarity	NPD7874	Approved
0.699	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6190	Approved
0.6984	Remote Similarity	NPD8090	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data