NPASS Compound

Structure

NPC45760 OpenBabel07101718312D 28 32 0 0 1 0 0 0 0 0999 V2000 4.0940 0.3410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -3.7601 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 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 -1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -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 3.1631 -0.0243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -0.7930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 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 0.8660 0.5000 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 -0.8660 -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 0.8660 -1.5000 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 1.7321 -1.0000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -1.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 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 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 7 15 2 0 0 0 0 8 1 1 6 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 5 1 1 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 24 2 0 0 0 0 15 18 1 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 17 22 1 0 0 0 0 18 21 2 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.15
Volume:	386.441
LogP:	6.276
LogD:	3.651
LogS:	-5.584
# Rotatable Bonds:	0
TPSA:	72.81
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.411
Synthetic Accessibility Score:	4.208
Fsp3:	0.348
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:	-4.817
MDCK Permeability:	2.1408368411357515e-05
Pgp-inhibitor:	0.145
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.168
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	90.0259017944336%
Volume Distribution (VD):	0.461
Pgp-substrate:	8.431354522705078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.557
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.547
CYP2C19-substrate:	0.484
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.539
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	3.147
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.674
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.375
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.394
Carcinogencity:	0.877
Eye Corrosion:	0.003
Eye Irritation:	0.331
Respiratory Toxicity:	0.164

Download Data

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

Natural Product: NPC45760

Natural Product ID:	NPC45760
*Common Name:**	Penicitrinone B
IUPAC Name:	n.a.
Synonyms:	Penicitrinone B
Standard InCHIKey:	WEDPJEXRPYHODY-PRHODGIISA-N
Standard InCHI:	InChI=1S/C23H22O5/c1-8-12(5)26-21-18-15(7-14(24)10(3)16(8)18)28-23-19(21)20(25)11(4)17-9(2)13(6)27-22(17)23/h7-8,12,25H,1-6H3/t8-,12-/m1/s1
SMILES:	C[C@H]1Oc2c3c([C@@H]1C)c(C)c(=O)cc3oc1c2c(O)c(C)c2c1oc(c2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1822987
PubChem CID:	56668327
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[495887]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[495887]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[495887]

☑ 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 NPC45760 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	454
0.1-0.2	1908
0.2-0.3	4287
0.3-0.4	11062
0.4-0.5	7486
0.5-0.6	3961
0.6-0.7	5522
0.7-0.8	5587
0.8-0.85	2011
0.85-0.9	396
0.9-0.95	21
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9107	High Similarity	NPC246877
0.8917	High Similarity	NPC261502
0.8848	High Similarity	NPC173587
0.8848	High Similarity	NPC475055
0.8848	High Similarity	NPC208120
0.8802	High Similarity	NPC232936
0.8795	High Similarity	NPC25361
0.8795	High Similarity	NPC21016
0.8795	High Similarity	NPC146584
0.875	High Similarity	NPC213416
0.8743	High Similarity	NPC191012
0.8735	High Similarity	NPC197168
0.8728	High Similarity	NPC8927
0.8728	High Similarity	NPC228209
0.8727	High Similarity	NPC66288
0.8706	High Similarity	NPC65885
0.8686	High Similarity	NPC240808
0.8663	High Similarity	NPC221820
0.8663	High Similarity	NPC77179
0.8663	High Similarity	NPC23553
0.8639	High Similarity	NPC475805
0.8625	High Similarity	NPC10010
0.8623	High Similarity	NPC273959
0.8623	High Similarity	NPC270837
0.8621	High Similarity	NPC246153
0.8613	High Similarity	NPC476273
0.8605	High Similarity	NPC49667
0.8605	High Similarity	NPC8127
0.8596	High Similarity	NPC30550
0.8588	High Similarity	NPC101107
0.8588	High Similarity	NPC476641
0.858	High Similarity	NPC126204
0.8571	High Similarity	NPC102372
0.8571	High Similarity	NPC326520
0.8563	High Similarity	NPC294965
0.8555	High Similarity	NPC5671
0.8547	High Similarity	NPC287243
0.8547	High Similarity	NPC289244
0.8547	High Similarity	NPC227906
0.8529	High Similarity	NPC476637
0.8529	High Similarity	NPC247136
0.8521	High Similarity	NPC170245
0.8521	High Similarity	NPC272502
0.8514	High Similarity	NPC240508
0.8503	High Similarity	NPC474186
0.8488	Intermediate Similarity	NPC476640
0.8488	Intermediate Similarity	NPC82217
0.8488	Intermediate Similarity	NPC310794
0.8488	Intermediate Similarity	NPC216842
0.8483	Intermediate Similarity	NPC295436
0.848	Intermediate Similarity	NPC28042
0.8475	Intermediate Similarity	NPC174486
0.8471	Intermediate Similarity	NPC95715
0.8471	Intermediate Similarity	NPC470456
0.8462	Intermediate Similarity	NPC45449
0.8462	Intermediate Similarity	NPC470457
0.8452	Intermediate Similarity	NPC472402
0.8452	Intermediate Similarity	NPC81679
0.8452	Intermediate Similarity	NPC229632
0.8444	Intermediate Similarity	NPC314020
0.8443	Intermediate Similarity	NPC475886
0.8443	Intermediate Similarity	NPC474287
0.8443	Intermediate Similarity	NPC246478
0.8439	Intermediate Similarity	NPC245975
0.8436	Intermediate Similarity	NPC60848
0.8434	Intermediate Similarity	NPC165977
0.8434	Intermediate Similarity	NPC217677
0.843	Intermediate Similarity	NPC54098
0.843	Intermediate Similarity	NPC230619
0.8421	Intermediate Similarity	NPC152477
0.8421	Intermediate Similarity	NPC177480
0.8421	Intermediate Similarity	NPC242395
0.8421	Intermediate Similarity	NPC165456
0.8412	Intermediate Similarity	NPC472452
0.8412	Intermediate Similarity	NPC43319
0.8412	Intermediate Similarity	NPC128293
0.8412	Intermediate Similarity	NPC470462
0.8412	Intermediate Similarity	NPC37870
0.8412	Intermediate Similarity	NPC120593
0.8412	Intermediate Similarity	NPC298071
0.8402	Intermediate Similarity	NPC132054
0.8402	Intermediate Similarity	NPC29055
0.8402	Intermediate Similarity	NPC133065
0.8402	Intermediate Similarity	NPC475985
0.8402	Intermediate Similarity	NPC470459
0.8402	Intermediate Similarity	NPC236132
0.8393	Intermediate Similarity	NPC474351
0.8393	Intermediate Similarity	NPC278427
0.8393	Intermediate Similarity	NPC475883
0.8393	Intermediate Similarity	NPC65746
0.8393	Intermediate Similarity	NPC474187
0.8393	Intermediate Similarity	NPC40037
0.8391	Intermediate Similarity	NPC107244
0.8383	Intermediate Similarity	NPC104876
0.8383	Intermediate Similarity	NPC245891
0.8382	Intermediate Similarity	NPC470942
0.8372	Intermediate Similarity	NPC313717
0.8372	Intermediate Similarity	NPC472276
0.8372	Intermediate Similarity	NPC315306
0.8363	Intermediate Similarity	NPC8965
0.8363	Intermediate Similarity	NPC477154
0.8363	Intermediate Similarity	NPC158761
0.8363	Intermediate Similarity	NPC150131
0.8363	Intermediate Similarity	NPC218226
0.8363	Intermediate Similarity	NPC117854
0.8363	Intermediate Similarity	NPC247973
0.8363	Intermediate Similarity	NPC6588
0.8362	Intermediate Similarity	NPC476170
0.8354	Intermediate Similarity	NPC115869
0.8353	Intermediate Similarity	NPC36320
0.8353	Intermediate Similarity	NPC37183
0.8353	Intermediate Similarity	NPC473286
0.8353	Intermediate Similarity	NPC472450
0.8353	Intermediate Similarity	NPC303174
0.8353	Intermediate Similarity	NPC316262
0.8353	Intermediate Similarity	NPC239752
0.8353	Intermediate Similarity	NPC39306
0.8353	Intermediate Similarity	NPC156432
0.8353	Intermediate Similarity	NPC314653
0.8353	Intermediate Similarity	NPC275780
0.8343	Intermediate Similarity	NPC52204
0.8343	Intermediate Similarity	NPC238995
0.8343	Intermediate Similarity	NPC261470
0.8333	Intermediate Similarity	NPC313368
0.8333	Intermediate Similarity	NPC56085
0.8333	Intermediate Similarity	NPC53917
0.8333	Intermediate Similarity	NPC14353
0.8333	Intermediate Similarity	NPC228785
0.8333	Intermediate Similarity	NPC224165
0.8333	Intermediate Similarity	NPC470810
0.8324	Intermediate Similarity	NPC476159
0.8324	Intermediate Similarity	NPC169018
0.8324	Intermediate Similarity	NPC121333
0.8324	Intermediate Similarity	NPC223375
0.8324	Intermediate Similarity	NPC475825
0.8323	Intermediate Similarity	NPC19097
0.8314	Intermediate Similarity	NPC473096
0.8314	Intermediate Similarity	NPC473095
0.8314	Intermediate Similarity	NPC326877
0.8313	Intermediate Similarity	NPC32557
0.8313	Intermediate Similarity	NPC189960
0.8305	Intermediate Similarity	NPC182693
0.8304	Intermediate Similarity	NPC173292
0.8304	Intermediate Similarity	NPC277480
0.8304	Intermediate Similarity	NPC39091
0.8304	Intermediate Similarity	NPC62444
0.8304	Intermediate Similarity	NPC477517
0.8295	Intermediate Similarity	NPC244903
0.8295	Intermediate Similarity	NPC104682
0.8294	Intermediate Similarity	NPC39305
0.8294	Intermediate Similarity	NPC23298
0.8294	Intermediate Similarity	NPC41301
0.8294	Intermediate Similarity	NPC152659
0.8294	Intermediate Similarity	NPC59295
0.8294	Intermediate Similarity	NPC474240
0.8294	Intermediate Similarity	NPC1706
0.8294	Intermediate Similarity	NPC1755
0.8294	Intermediate Similarity	NPC476822
0.8294	Intermediate Similarity	NPC248638
0.8294	Intermediate Similarity	NPC186686
0.8294	Intermediate Similarity	NPC189473
0.8294	Intermediate Similarity	NPC263092
0.8294	Intermediate Similarity	NPC236521
0.8294	Intermediate Similarity	NPC7483
0.8294	Intermediate Similarity	NPC207690
0.8293	Intermediate Similarity	NPC216917
0.8286	Intermediate Similarity	NPC216307
0.8284	Intermediate Similarity	NPC61010
0.8284	Intermediate Similarity	NPC269117
0.8284	Intermediate Similarity	NPC278052
0.8284	Intermediate Similarity	NPC40491
0.8284	Intermediate Similarity	NPC117985
0.8284	Intermediate Similarity	NPC187354
0.8276	Intermediate Similarity	NPC233956
0.8276	Intermediate Similarity	NPC277510
0.8274	Intermediate Similarity	NPC469658
0.8274	Intermediate Similarity	NPC250214
0.8274	Intermediate Similarity	NPC125969
0.8274	Intermediate Similarity	NPC315157
0.8274	Intermediate Similarity	NPC100123
0.8274	Intermediate Similarity	NPC95936
0.8274	Intermediate Similarity	NPC85121
0.8274	Intermediate Similarity	NPC250076
0.8266	Intermediate Similarity	NPC102277
0.8266	Intermediate Similarity	NPC131866
0.8266	Intermediate Similarity	NPC281835
0.8266	Intermediate Similarity	NPC279209
0.8266	Intermediate Similarity	NPC17219
0.8263	Intermediate Similarity	NPC45131
0.8263	Intermediate Similarity	NPC178854
0.8263	Intermediate Similarity	NPC268161
0.8263	Intermediate Similarity	NPC292107
0.8263	Intermediate Similarity	NPC180924
0.8263	Intermediate Similarity	NPC164244
0.8256	Intermediate Similarity	NPC470704
0.8256	Intermediate Similarity	NPC473094
0.8256	Intermediate Similarity	NPC223413
0.8256	Intermediate Similarity	NPC225419
0.8256	Intermediate Similarity	NPC474024
0.8253	Intermediate Similarity	NPC273248

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 NPC45760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	1044
0.2-0.3	2006
0.3-0.4	2698
0.4-0.5	1711
0.5-0.6	824
0.6-0.7	319
0.7-0.8	112
0.8-0.85	23
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8314	Intermediate Similarity	NPD5844	Phase 1
0.8225	Intermediate Similarity	NPD5494	Approved
0.8176	Intermediate Similarity	NPD1247	Approved
0.8047	Intermediate Similarity	NPD3882	Suspended
0.8036	Intermediate Similarity	NPD2801	Approved
0.7989	Intermediate Similarity	NPD7473	Discontinued
0.7988	Intermediate Similarity	NPD2533	Approved
0.7988	Intermediate Similarity	NPD2534	Approved
0.7988	Intermediate Similarity	NPD2532	Approved
0.7965	Intermediate Similarity	NPD6959	Discontinued
0.7929	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6232	Discontinued
0.787	Intermediate Similarity	NPD1934	Approved
0.7849	Intermediate Similarity	NPD919	Approved
0.7829	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6166	Phase 2
0.7821	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2800	Approved
0.7778	Intermediate Similarity	NPD3817	Phase 2
0.7771	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3818	Discontinued
0.7733	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD1465	Phase 2
0.7624	Intermediate Similarity	NPD7808	Phase 3
0.7619	Intermediate Similarity	NPD1512	Approved
0.7611	Intermediate Similarity	NPD6797	Phase 2
0.7586	Intermediate Similarity	NPD7075	Discontinued
0.7572	Intermediate Similarity	NPD5402	Approved
0.7571	Intermediate Similarity	NPD3926	Phase 2
0.7569	Intermediate Similarity	NPD6559	Discontinued
0.7569	Intermediate Similarity	NPD7251	Discontinued
0.7558	Intermediate Similarity	NPD6801	Discontinued
0.7558	Intermediate Similarity	NPD37	Approved
0.7544	Intermediate Similarity	NPD4380	Phase 2
0.7543	Intermediate Similarity	NPD6234	Discontinued
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.7514	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7472	Approved
0.7459	Intermediate Similarity	NPD7074	Phase 3
0.7425	Intermediate Similarity	NPD3750	Approved
0.7416	Intermediate Similarity	NPD5711	Approved
0.7416	Intermediate Similarity	NPD5710	Approved
0.7414	Intermediate Similarity	NPD7819	Suspended
0.7394	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3749	Approved
0.7368	Intermediate Similarity	NPD920	Approved
0.7366	Intermediate Similarity	NPD8434	Phase 2
0.7353	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3751	Discontinued
0.7348	Intermediate Similarity	NPD7228	Approved
0.7341	Intermediate Similarity	NPD6599	Discontinued
0.7305	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7199	Phase 2
0.7246	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3787	Discontinued
0.7212	Intermediate Similarity	NPD6651	Approved
0.7202	Intermediate Similarity	NPD1549	Phase 2
0.7193	Intermediate Similarity	NPD6799	Approved
0.7186	Intermediate Similarity	NPD6099	Approved
0.7186	Intermediate Similarity	NPD6100	Approved
0.7186	Intermediate Similarity	NPD2796	Approved
0.7178	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5403	Approved
0.716	Intermediate Similarity	NPD1243	Approved
0.7151	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7229	Phase 3
0.7126	Intermediate Similarity	NPD1510	Phase 2
0.7126	Intermediate Similarity	NPD3748	Approved
0.7118	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7411	Suspended
0.7093	Intermediate Similarity	NPD7390	Discontinued
0.709	Intermediate Similarity	NPD8150	Discontinued
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6674	Discontinued
0.7056	Intermediate Similarity	NPD3057	Approved
0.7053	Intermediate Similarity	NPD7907	Approved
0.7052	Intermediate Similarity	NPD5401	Approved
0.7052	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2403	Approved
0.7048	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5124	Phase 1
0.7041	Intermediate Similarity	NPD6777	Approved
0.7041	Intermediate Similarity	NPD6778	Approved
0.7041	Intermediate Similarity	NPD6776	Approved
0.7041	Intermediate Similarity	NPD6780	Approved
0.7041	Intermediate Similarity	NPD6781	Approved
0.7041	Intermediate Similarity	NPD6782	Approved
0.7041	Intermediate Similarity	NPD6779	Approved
0.7039	Intermediate Similarity	NPD4111	Phase 1
0.7039	Intermediate Similarity	NPD7768	Phase 2
0.7039	Intermediate Similarity	NPD4665	Approved
0.7035	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7435	Discontinued
0.7018	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD1607	Approved
0.7005	Intermediate Similarity	NPD7240	Approved
0.6989	Remote Similarity	NPD3226	Approved
0.697	Remote Similarity	NPD2972	Approved
0.697	Remote Similarity	NPD3533	Approved
0.6968	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD230	Phase 1
0.6941	Remote Similarity	NPD2344	Approved
0.6941	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2346	Discontinued
0.6935	Remote Similarity	NPD7697	Approved
0.6935	Remote Similarity	NPD7698	Approved
0.6935	Remote Similarity	NPD7696	Phase 3
0.6931	Remote Similarity	NPD8313	Approved
0.6931	Remote Similarity	NPD8312	Approved
0.6919	Remote Similarity	NPD2494	Approved
0.6919	Remote Similarity	NPD2493	Approved
0.6909	Remote Similarity	NPD4625	Phase 3
0.69	Remote Similarity	NPD7870	Phase 2
0.69	Remote Similarity	NPD7871	Phase 2
0.69	Remote Similarity	NPD4583	Approved
0.69	Remote Similarity	NPD4582	Approved
0.6897	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD2974	Approved
0.6888	Remote Similarity	NPD2973	Approved
0.6888	Remote Similarity	NPD2975	Approved
0.6886	Remote Similarity	NPD1613	Approved
0.6886	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4060	Phase 1
0.6886	Remote Similarity	NPD1240	Approved
0.6884	Remote Similarity	NPD2491	Approved
0.6882	Remote Similarity	NPD2163	Approved
0.6882	Remote Similarity	NPD2935	Discontinued
0.6879	Remote Similarity	NPD6190	Approved
0.6872	Remote Similarity	NPD6535	Approved
0.6872	Remote Similarity	NPD6534	Approved
0.6869	Remote Similarity	NPD4107	Approved
0.6869	Remote Similarity	NPD4580	Approved
0.6867	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.685	Remote Similarity	NPD4004	Approved
0.685	Remote Similarity	NPD4002	Approved
0.6847	Remote Similarity	NPD8151	Discontinued
0.6842	Remote Similarity	NPD1471	Phase 3
0.6836	Remote Similarity	NPD1653	Approved
0.6834	Remote Similarity	NPD3450	Approved
0.6834	Remote Similarity	NPD3452	Approved
0.6825	Remote Similarity	NPD7685	Pre-registration
0.6824	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7874	Approved
0.6807	Remote Similarity	NPD3027	Phase 3
0.6804	Remote Similarity	NPD2490	Approved
0.6804	Remote Similarity	NPD2488	Approved
0.68	Remote Similarity	NPD3448	Approved
0.6798	Remote Similarity	NPD7458	Discontinued
0.6798	Remote Similarity	NPD7701	Phase 2
0.6793	Remote Similarity	NPD8127	Discontinued
0.6788	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2309	Approved
0.678	Remote Similarity	NPD7801	Approved
0.678	Remote Similarity	NPD7783	Phase 2
0.678	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5676	Approved
0.6768	Remote Similarity	NPD7699	Phase 2
0.6768	Remote Similarity	NPD7700	Phase 2
0.6766	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4482	Phase 3
0.6748	Remote Similarity	NPD4749	Approved
0.6747	Remote Similarity	NPD4908	Phase 1
0.6747	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6355	Discontinued
0.6745	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5760	Phase 2
0.674	Remote Similarity	NPD5761	Phase 2
0.6737	Remote Similarity	NPD6764	Approved
0.6737	Remote Similarity	NPD6765	Approved
0.6737	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8366	Approved
0.6724	Remote Similarity	NPD7003	Approved
0.6724	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6273	Approved
0.6719	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6696	Suspended
0.6703	Remote Similarity	NPD5353	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