NPASS Compound

Structure

NPC251160 OpenBabel07101718222D 24 28 0 0 0 0 0 0 0 0999 V2000 -0.6722 -2.1824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0487 -1.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0628 -4.3494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0058 -2.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0634 -1.6857 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 -2.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 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 -2.3113 -2.7889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4265 -1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.5860 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 -1.7321 -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 -3.4641 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 -1.0376 -1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2366 -3.7861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 21 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 11 16 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	319.12
Volume:	327.97
LogP:	5.017
LogD:	3.66
LogS:	-6.396
# Rotatable Bonds:	1
TPSA:	40.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.671
Synthetic Accessibility Score:	2.793
Fsp3:	0.25
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:	-5.162
MDCK Permeability:	2.192550164181739e-05
Pgp-inhibitor:	0.621
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	98.13789367675781%
Volume Distribution (VD):	3.179
Pgp-substrate:	1.50237238407135%

ADMET: Metabolism

CYP1A2-inhibitor:	0.941
CYP1A2-substrate:	0.639
CYP2C19-inhibitor:	0.973
CYP2C19-substrate:	0.397
CYP2C9-inhibitor:	0.889
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.874
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.64

ADMET: Excretion

Clearance (CL):	4.121
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.717
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.506
Carcinogencity:	0.903
Eye Corrosion:	0.004
Eye Irritation:	0.192
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC251160

Natural Product ID:	NPC251160
*Common Name:**	GLMROMLEFUHTEP-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GLMROMLEFUHTEP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H17NO3/c1-20(2)14-9-12(22-3)4-5-13(14)17-16-11(6-7-21-19(16)20)8-15-18(17)24-10-23-15/h4-9H,10H2,1-3H3
SMILES:	CC1(C)c2cc(ccc2-c2c3c(ccnc13)cc1c2OCO1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593299
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO27037	Hornschuchia obliqua	Species	Annonaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[26135746]
NPO27037	Hornschuchia obliqua	Species	Annonaceae	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	3

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	4700.0	nM	PMID[489961]
NPT2	Others	Unspecified	Ratio IC50	=	40.0	n.a.	PMID[489961]
NPT27	Others	Unspecified	Activity	=	95.7	%	PMID[489961]
NPT27	Others	Unspecified	Activity	=	86.7	%	PMID[489961]

☑ 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 NPC251160 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	652
0.1-0.2	3198
0.2-0.3	12611
0.3-0.4	5376
0.4-0.5	14043
0.5-0.6	4608
0.6-0.7	1851
0.7-0.8	281
0.8-0.85	34
0.85-0.9	31
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC477019
0.9188	High Similarity	NPC235076
0.9179	High Similarity	NPC188420
0.9146	High Similarity	NPC100079
0.9146	High Similarity	NPC23614
0.9137	High Similarity	NPC149471
0.9137	High Similarity	NPC271215
0.911	High Similarity	NPC234197
0.9086	High Similarity	NPC202768
0.9086	High Similarity	NPC296482
0.9086	High Similarity	NPC53069
0.9026	High Similarity	NPC313189
0.9005	High Similarity	NPC46451
0.8942	High Similarity	NPC133140
0.8942	High Similarity	NPC195268
0.8894	High Similarity	NPC96405
0.8894	High Similarity	NPC171409
0.8889	High Similarity	NPC278525
0.8873	High Similarity	NPC118121
0.8873	High Similarity	NPC122463
0.8861	High Similarity	NPC204446
0.8852	High Similarity	NPC22481
0.8832	High Similarity	NPC135549
0.8768	High Similarity	NPC108342
0.8731	High Similarity	NPC16452
0.8731	High Similarity	NPC36229
0.8731	High Similarity	NPC476581
0.8726	High Similarity	NPC182907
0.8726	High Similarity	NPC189903
0.8685	High Similarity	NPC166722
0.8667	High Similarity	NPC4071
0.8667	High Similarity	NPC476578
0.8667	High Similarity	NPC476582
0.8599	High Similarity	NPC210434
0.8579	High Similarity	NPC31930
0.8519	High Similarity	NPC210296
0.8486	Intermediate Similarity	NPC124313
0.8479	Intermediate Similarity	NPC84164
0.8479	Intermediate Similarity	NPC207283
0.8443	Intermediate Similarity	NPC24019
0.8431	Intermediate Similarity	NPC202605
0.8431	Intermediate Similarity	NPC112206
0.8424	Intermediate Similarity	NPC290689
0.8296	Intermediate Similarity	NPC183537
0.829	Intermediate Similarity	NPC204385
0.8272	Intermediate Similarity	NPC206201
0.8238	Intermediate Similarity	NPC174049
0.8214	Intermediate Similarity	NPC77878
0.8203	Intermediate Similarity	NPC90875
0.8194	Intermediate Similarity	NPC233334
0.8155	Intermediate Similarity	NPC470020
0.8144	Intermediate Similarity	NPC249405
0.8125	Intermediate Similarity	NPC236668
0.8119	Intermediate Similarity	NPC253675
0.8116	Intermediate Similarity	NPC208284
0.8086	Intermediate Similarity	NPC146976
0.8057	Intermediate Similarity	NPC473822
0.801	Intermediate Similarity	NPC312872
0.8	Intermediate Similarity	NPC179704
0.798	Intermediate Similarity	NPC312531
0.7946	Intermediate Similarity	NPC15406
0.7938	Intermediate Similarity	NPC287588
0.7909	Intermediate Similarity	NPC255800
0.7909	Intermediate Similarity	NPC96584
0.79	Intermediate Similarity	NPC201508
0.79	Intermediate Similarity	NPC280964
0.79	Intermediate Similarity	NPC114335
0.79	Intermediate Similarity	NPC141915
0.7889	Intermediate Similarity	NPC474904
0.7885	Intermediate Similarity	NPC270515
0.7867	Intermediate Similarity	NPC162530
0.7867	Intermediate Similarity	NPC266931
0.7843	Intermediate Similarity	NPC287437
0.7835	Intermediate Similarity	NPC285941
0.7833	Intermediate Similarity	NPC224928
0.7778	Intermediate Similarity	NPC217554
0.7758	Intermediate Similarity	NPC295228
0.7757	Intermediate Similarity	NPC473513
0.774	Intermediate Similarity	NPC285558
0.7737	Intermediate Similarity	NPC266753
0.7737	Intermediate Similarity	NPC232924
0.7737	Intermediate Similarity	NPC306902
0.7737	Intermediate Similarity	NPC477559
0.7737	Intermediate Similarity	NPC160298
0.7721	Intermediate Similarity	NPC173080
0.7717	Intermediate Similarity	NPC470018
0.7703	Intermediate Similarity	NPC323345
0.7703	Intermediate Similarity	NPC470164
0.7696	Intermediate Similarity	NPC24954
0.7689	Intermediate Similarity	NPC11408
0.7685	Intermediate Similarity	NPC302001
0.7682	Intermediate Similarity	NPC74575
0.7675	Intermediate Similarity	NPC284141
0.7633	Intermediate Similarity	NPC11017
0.7626	Intermediate Similarity	NPC322482
0.7626	Intermediate Similarity	NPC190461
0.7623	Intermediate Similarity	NPC49547
0.7617	Intermediate Similarity	NPC225774
0.7585	Intermediate Similarity	NPC212163
0.758	Intermediate Similarity	NPC280272
0.7577	Intermediate Similarity	NPC219341
0.7577	Intermediate Similarity	NPC476432
0.7577	Intermediate Similarity	NPC24264
0.7577	Intermediate Similarity	NPC86144
0.7577	Intermediate Similarity	NPC304659
0.757	Intermediate Similarity	NPC316981
0.7562	Intermediate Similarity	NPC33902
0.7562	Intermediate Similarity	NPC276674
0.7548	Intermediate Similarity	NPC176538
0.7547	Intermediate Similarity	NPC470931
0.7546	Intermediate Similarity	NPC170114
0.7538	Intermediate Similarity	NPC247389
0.7538	Intermediate Similarity	NPC298979
0.7537	Intermediate Similarity	NPC76748
0.7536	Intermediate Similarity	NPC193906
0.7536	Intermediate Similarity	NPC23080
0.7526	Intermediate Similarity	NPC302527
0.7526	Intermediate Similarity	NPC167546
0.7526	Intermediate Similarity	NPC16805
0.7524	Intermediate Similarity	NPC162653
0.7512	Intermediate Similarity	NPC295676
0.7512	Intermediate Similarity	NPC201697
0.7512	Intermediate Similarity	NPC307963
0.7512	Intermediate Similarity	NPC267423
0.75	Intermediate Similarity	NPC193777
0.75	Intermediate Similarity	NPC470549
0.75	Intermediate Similarity	NPC241055
0.75	Intermediate Similarity	NPC474595
0.75	Intermediate Similarity	NPC92111
0.75	Intermediate Similarity	NPC476999
0.749	Intermediate Similarity	NPC132385
0.7489	Intermediate Similarity	NPC476997
0.7488	Intermediate Similarity	NPC164374
0.7488	Intermediate Similarity	NPC296527
0.7488	Intermediate Similarity	NPC137929
0.7477	Intermediate Similarity	NPC123976
0.7477	Intermediate Similarity	NPC11464
0.7477	Intermediate Similarity	NPC167860
0.7477	Intermediate Similarity	NPC200888
0.7476	Intermediate Similarity	NPC131017
0.7474	Intermediate Similarity	NPC189470
0.7465	Intermediate Similarity	NPC82548
0.7455	Intermediate Similarity	NPC476998
0.7455	Intermediate Similarity	NPC476996
0.7449	Intermediate Similarity	NPC210918
0.7445	Intermediate Similarity	NPC470017
0.7443	Intermediate Similarity	NPC148409
0.7441	Intermediate Similarity	NPC475774
0.7441	Intermediate Similarity	NPC162484
0.744	Intermediate Similarity	NPC251090
0.7436	Intermediate Similarity	NPC168409
0.7429	Intermediate Similarity	NPC232727
0.7412	Intermediate Similarity	NPC473183
0.7412	Intermediate Similarity	NPC470022
0.7411	Intermediate Similarity	NPC476994
0.7406	Intermediate Similarity	NPC244606
0.7406	Intermediate Similarity	NPC156728
0.7402	Intermediate Similarity	NPC320088
0.7399	Intermediate Similarity	NPC214980
0.7391	Intermediate Similarity	NPC119134
0.7378	Intermediate Similarity	NPC469792
0.7374	Intermediate Similarity	NPC6152
0.7373	Intermediate Similarity	NPC474594
0.7371	Intermediate Similarity	NPC304183
0.7368	Intermediate Similarity	NPC81733
0.7368	Intermediate Similarity	NPC72211
0.7368	Intermediate Similarity	NPC326316
0.7366	Intermediate Similarity	NPC296742
0.7364	Intermediate Similarity	NPC193267
0.7364	Intermediate Similarity	NPC213530
0.7357	Intermediate Similarity	NPC473182
0.7353	Intermediate Similarity	NPC69213
0.7349	Intermediate Similarity	NPC174672
0.7349	Intermediate Similarity	NPC174758
0.7337	Intermediate Similarity	NPC149090
0.7337	Intermediate Similarity	NPC19520
0.7327	Intermediate Similarity	NPC94157
0.7327	Intermediate Similarity	NPC473180
0.7327	Intermediate Similarity	NPC48353
0.7325	Intermediate Similarity	NPC473184
0.7324	Intermediate Similarity	NPC118832
0.7324	Intermediate Similarity	NPC47059
0.7324	Intermediate Similarity	NPC329708
0.7324	Intermediate Similarity	NPC165349
0.7324	Intermediate Similarity	NPC264166
0.7324	Intermediate Similarity	NPC274291
0.7321	Intermediate Similarity	NPC70956
0.7321	Intermediate Similarity	NPC243834
0.7317	Intermediate Similarity	NPC224293
0.7315	Intermediate Similarity	NPC199667
0.7311	Intermediate Similarity	NPC199277
0.7311	Intermediate Similarity	NPC135887
0.7299	Intermediate Similarity	NPC329747
0.7299	Intermediate Similarity	NPC315957
0.7299	Intermediate Similarity	NPC329793
0.7296	Intermediate Similarity	NPC208522
0.7294	Intermediate Similarity	NPC478074
0.7286	Intermediate Similarity	NPC152212
0.7285	Intermediate Similarity	NPC17565
0.7282	Intermediate Similarity	NPC112676

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 NPC251160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	666
0.2-0.3	895
0.3-0.4	1517
0.4-0.5	2736
0.5-0.6	2161
0.6-0.7	713
0.7-0.8	86
0.8-0.85	2
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9086	High Similarity	NPD3815	Phase 1
0.9086	High Similarity	NPD3816	Phase 1
0.9005	High Similarity	NPD3763	Approved
0.8942	High Similarity	NPD3924	Approved
0.8942	High Similarity	NPD3923	Approved
0.8942	High Similarity	NPD3922	Approved
0.8942	High Similarity	NPD3921	Approved
0.8457	Intermediate Similarity	NPD3920	Phase 2
0.8154	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD6494	Phase 2
0.7799	Intermediate Similarity	NPD5658	Approved
0.7783	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4889	Approved
0.7736	Intermediate Similarity	NPD7069	Discontinued
0.7732	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7729	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6219	Discontinued
0.765	Intermediate Similarity	NPD7169	Suspended
0.7635	Intermediate Similarity	NPD6569	Phase 2
0.7629	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD6281	Approved
0.7619	Intermediate Similarity	NPD5530	Phase 1
0.7598	Intermediate Similarity	NPD6230	Discontinued
0.7583	Intermediate Similarity	NPD7222	Phase 2
0.7563	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4418	Discontinued
0.7545	Intermediate Similarity	NPD4885	Approved
0.7538	Intermediate Similarity	NPD3386	Phase 2
0.7526	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD1038	Approved
0.75	Intermediate Similarity	NPD2334	Discontinued
0.7478	Intermediate Similarity	NPD6963	Approved
0.7478	Intermediate Similarity	NPD6964	Approved
0.7453	Intermediate Similarity	NPD2060	Approved
0.7436	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7555	Discontinued
0.7406	Intermediate Similarity	NPD4795	Phase 2
0.7397	Intermediate Similarity	NPD6568	Discontinued
0.7389	Intermediate Similarity	NPD4375	Approved
0.7385	Intermediate Similarity	NPD5612	Discontinued
0.7378	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7567	Approved
0.7357	Intermediate Similarity	NPD7558	Phase 2
0.7343	Intermediate Similarity	NPD4551	Phase 2
0.7339	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD7453	Approved
0.7336	Intermediate Similarity	NPD7452	Approved
0.7333	Intermediate Similarity	NPD2780	Approved
0.7333	Intermediate Similarity	NPD2782	Approved
0.733	Intermediate Similarity	NPD5930	Phase 3
0.733	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4039	Approved
0.7324	Intermediate Similarity	NPD4034	Approved
0.7324	Intermediate Similarity	NPD4038	Approved
0.7324	Intermediate Similarity	NPD4035	Approved
0.7324	Intermediate Similarity	NPD4033	Approved
0.7324	Intermediate Similarity	NPD31	Approved
0.7324	Intermediate Similarity	NPD32	Approved
0.7324	Intermediate Similarity	NPD4037	Approved
0.7324	Intermediate Similarity	NPD4036	Approved
0.7324	Intermediate Similarity	NPD4122	Approved
0.7311	Intermediate Similarity	NPD6975	Discontinued
0.7302	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1739	Approved
0.7299	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1740	Approved
0.7286	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3477	Phase 2
0.7273	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5903	Approved
0.726	Intermediate Similarity	NPD5902	Approved
0.7259	Intermediate Similarity	NPD2781	Approved
0.7256	Intermediate Similarity	NPD5429	Discontinued
0.7251	Intermediate Similarity	NPD3825	Phase 3
0.7244	Intermediate Similarity	NPD7674	Phase 3
0.7244	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7675	Phase 3
0.7243	Intermediate Similarity	NPD3397	Phase 2
0.7229	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5601	Phase 2
0.7208	Intermediate Similarity	NPD8091	Phase 3
0.7184	Intermediate Similarity	NPD1034	Phase 3
0.7184	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6361	Phase 2
0.7162	Intermediate Similarity	NPD3354	Phase 2
0.7156	Intermediate Similarity	NPD6262	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3395	Approved
0.7143	Intermediate Similarity	NPD3396	Approved
0.7143	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD4875	Phase 3
0.7137	Intermediate Similarity	NPD4876	Phase 3
0.7137	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD8016	Phase 3
0.7124	Intermediate Similarity	NPD7719	Discontinued
0.7123	Intermediate Similarity	NPD5066	Phase 2
0.7123	Intermediate Similarity	NPD4131	Phase 3
0.7123	Intermediate Similarity	NPD5067	Phase 2
0.7123	Intermediate Similarity	NPD4502	Phase 2
0.7117	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD4044	Discontinued
0.7112	Intermediate Similarity	NPD5805	Approved
0.7098	Intermediate Similarity	NPD6242	Discontinued
0.7097	Intermediate Similarity	NPD1392	Approved
0.7094	Intermediate Similarity	NPD6790	Phase 1
0.7093	Intermediate Similarity	NPD7426	Phase 1
0.7089	Intermediate Similarity	NPD4548	Discontinued
0.7087	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5147	Discontinued
0.7064	Intermediate Similarity	NPD2187	Approved
0.7064	Intermediate Similarity	NPD6517	Phase 3
0.7064	Intermediate Similarity	NPD7672	Approved
0.7064	Intermediate Similarity	NPD7671	Approved
0.7064	Intermediate Similarity	NPD2189	Approved
0.7062	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6501	Approved
0.7054	Intermediate Similarity	NPD6500	Approved
0.7053	Intermediate Similarity	NPD4919	Phase 3
0.7053	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2917	Approved
0.7053	Intermediate Similarity	NPD4921	Phase 3
0.7051	Intermediate Similarity	NPD3003	Approved
0.7048	Intermediate Similarity	NPD4372	Phase 1
0.7046	Intermediate Similarity	NPD8100	Phase 3
0.7044	Intermediate Similarity	NPD4071	Approved
0.7044	Intermediate Similarity	NPD4072	Approved
0.7044	Intermediate Similarity	NPD1032	Phase 2
0.7042	Intermediate Similarity	NPD7859	Phase 2
0.7039	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1856	Discontinued
0.7035	Intermediate Similarity	NPD1954	Phase 1
0.7032	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5559	Phase 2
0.7031	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4204	Approved
0.7024	Intermediate Similarity	NPD4203	Approved
0.7022	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7051	Phase 3
0.7018	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6727	Phase 2
0.7009	Intermediate Similarity	NPD7395	Discontinued
0.7005	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2952	Discontinued
0.6995	Remote Similarity	NPD5100	Phase 3
0.6995	Remote Similarity	NPD7948	Phase 1
0.6995	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6298	Discontinued
0.6986	Remote Similarity	NPD3349	Phase 2
0.6986	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5529	Phase 1
0.6983	Remote Similarity	NPD8442	Discontinued
0.6981	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD2600	Approved
0.6976	Remote Similarity	NPD2599	Approved
0.6976	Remote Similarity	NPD2601	Approved
0.697	Remote Similarity	NPD4995	Approved
0.697	Remote Similarity	NPD4996	Approved
0.6968	Remote Similarity	NPD6220	Phase 3
0.6958	Remote Similarity	NPD8101	Phase 3
0.6957	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD8063	Discontinued
0.6948	Remote Similarity	NPD6550	Discontinued
0.6948	Remote Similarity	NPD2482	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5999	Phase 2
0.6926	Remote Similarity	NPD6968	Phase 2
0.6926	Remote Similarity	NPD4925	Approved
0.6926	Remote Similarity	NPD6969	Phase 2
0.692	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD9705	Discontinued
0.6919	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD112	Approved
0.6912	Remote Similarity	NPD6208	Discontinued
0.6906	Remote Similarity	NPD5945	Phase 1
0.6906	Remote Similarity	NPD5944	Phase 1
0.6904	Remote Similarity	NPD5488	Discontinued
0.6904	Remote Similarity	NPD2582	Approved
0.6904	Remote Similarity	NPD2581	Approved
0.6903	Remote Similarity	NPD3402	Phase 1
0.6903	Remote Similarity	NPD7194	Discontinued
0.6898	Remote Similarity	NPD7956	Approved
0.6898	Remote Similarity	NPD7955	Approved
0.6892	Remote Similarity	NPD5936	Approved
0.6892	Remote Similarity	NPD5939	Approved
0.689	Remote Similarity	NPD5256	Discontinued
0.6881	Remote Similarity	NPD6991	Approved
0.6878	Remote Similarity	NPD4437	Phase 3

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