NPASS Compound

Structure

NPC472952 OpenBabel07101718242D 24 27 0 0 1 0 0 0 0 0999 V2000 -6.6369 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9456 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5878 0.8090 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 1 17 1 0 0 0 0 2 17 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 6 0 0 0 14 18 1 6 0 0 0 14 19 1 0 0 0 0 15 10 1 6 0 0 0 15 20 1 0 0 0 0 15 23 1 0 0 0 0 16 20 1 6 0 0 0 16 24 1 0 0 0 0 18 3 1 6 0 0 0 19 4 1 6 0 0 0 19 23 1 0 0 0 0 20 12 1 1 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.25
Volume:	355.411
LogP:	3.543
LogD:	3.062
LogS:	-4.243
# Rotatable Bonds:	3
TPSA:	62.22
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.777
Synthetic Accessibility Score:	4.858
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.734
MDCK Permeability:	1.843062818807084e-05
Pgp-inhibitor:	0.801
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.319

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.182
Plasma Protein Binding (PPB):	86.1495590209961%
Volume Distribution (VD):	1.578
Pgp-substrate:	15.99763298034668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.336
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.668
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	10.119
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.451
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.463
Maximum Recommended Daily Dose:	0.204
Skin Sensitization:	0.588
Carcinogencity:	0.413
Eye Corrosion:	0.708
Eye Irritation:	0.472
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC472952

Natural Product ID:	NPC472952
*Common Name:**	XFQYFHPEWOWCKX-DYAQGPOSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XFQYFHPEWOWCKX-DYAQGPOSSA-N
Standard InCHI:	InChI=1S/C20H34O4/c1-17(2)7-5-8-18(3)13(17)6-9-19(4)14(18)10-15(23-19)20(12-22)16(11-21)24-20/h13-16,21-22H,5-12H2,1-4H3/t13-,14+,15-,16+,18-,19+,20-/m0/s1
SMILES:	OC[C@H]1O[C@@]1(CO)[C@@H]1C[C@H]2[C@@](O1)(C)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594172
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO33325	silphium laciniatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26287548]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	10000.0	nM	PMID[507933]

☑ 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 NPC472952 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	401
0.1-0.2	3946
0.2-0.3	12216
0.3-0.4	12051
0.4-0.5	5525
0.5-0.6	5681
0.6-0.7	2393
0.7-0.8	426
0.8-0.85	47
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472950
0.9324	High Similarity	NPC472951
0.9324	High Similarity	NPC472943
0.9028	High Similarity	NPC470151
0.8816	High Similarity	NPC16449
0.8816	High Similarity	NPC186588
0.8684	High Similarity	NPC477282
0.8684	High Similarity	NPC81074
0.8667	High Similarity	NPC474574
0.8667	High Similarity	NPC64081
0.8667	High Similarity	NPC11907
0.8667	High Similarity	NPC133596
0.859	High Similarity	NPC475388
0.859	High Similarity	NPC477447
0.859	High Similarity	NPC470155
0.859	High Similarity	NPC477446
0.8472	Intermediate Similarity	NPC470833
0.8462	Intermediate Similarity	NPC470156
0.8462	Intermediate Similarity	NPC470154
0.8421	Intermediate Similarity	NPC476233
0.84	Intermediate Similarity	NPC231680
0.84	Intermediate Similarity	NPC270306
0.84	Intermediate Similarity	NPC91387
0.8375	Intermediate Similarity	NPC18953
0.8312	Intermediate Similarity	NPC471769
0.8312	Intermediate Similarity	NPC177343
0.8289	Intermediate Similarity	NPC136424
0.8289	Intermediate Similarity	NPC470145
0.8289	Intermediate Similarity	NPC107963
0.8243	Intermediate Similarity	NPC131506
0.8243	Intermediate Similarity	NPC187471
0.8243	Intermediate Similarity	NPC127283
0.8243	Intermediate Similarity	NPC470071
0.8243	Intermediate Similarity	NPC252182
0.8243	Intermediate Similarity	NPC8004
0.8243	Intermediate Similarity	NPC1340
0.8243	Intermediate Similarity	NPC157777
0.8228	Intermediate Similarity	NPC473257
0.8193	Intermediate Similarity	NPC470872
0.8171	Intermediate Similarity	NPC155531
0.8171	Intermediate Similarity	NPC471411
0.8171	Intermediate Similarity	NPC215968
0.8171	Intermediate Similarity	NPC471410
0.8158	Intermediate Similarity	NPC158208
0.8158	Intermediate Similarity	NPC196136
0.8158	Intermediate Similarity	NPC317242
0.8158	Intermediate Similarity	NPC243027
0.8148	Intermediate Similarity	NPC320824
0.8101	Intermediate Similarity	NPC186594
0.8101	Intermediate Similarity	NPC66766
0.8101	Intermediate Similarity	NPC117137
0.8077	Intermediate Similarity	NPC272841
0.8077	Intermediate Similarity	NPC43463
0.8077	Intermediate Similarity	NPC252483
0.8077	Intermediate Similarity	NPC147993
0.8077	Intermediate Similarity	NPC191345
0.8072	Intermediate Similarity	NPC161928
0.8072	Intermediate Similarity	NPC62202
0.8072	Intermediate Similarity	NPC213658
0.8072	Intermediate Similarity	NPC110365
0.8072	Intermediate Similarity	NPC45833
0.8072	Intermediate Similarity	NPC210658
0.8052	Intermediate Similarity	NPC163597
0.8049	Intermediate Similarity	NPC290612
0.8049	Intermediate Similarity	NPC235402
0.8028	Intermediate Similarity	NPC476702
0.8026	Intermediate Similarity	NPC10476
0.8026	Intermediate Similarity	NPC308489
0.8026	Intermediate Similarity	NPC228994
0.8026	Intermediate Similarity	NPC475458
0.8026	Intermediate Similarity	NPC192501
0.8025	Intermediate Similarity	NPC477978
0.8025	Intermediate Similarity	NPC241959
0.8025	Intermediate Similarity	NPC111582
0.8025	Intermediate Similarity	NPC477285
0.8025	Intermediate Similarity	NPC470070
0.8023	Intermediate Similarity	NPC475307
0.7976	Intermediate Similarity	NPC476379
0.7976	Intermediate Similarity	NPC128475
0.7975	Intermediate Similarity	NPC287452
0.7975	Intermediate Similarity	NPC269333
0.7973	Intermediate Similarity	NPC107919
0.7973	Intermediate Similarity	NPC66407
0.7952	Intermediate Similarity	NPC477283
0.7949	Intermediate Similarity	NPC476719
0.7949	Intermediate Similarity	NPC105208
0.7949	Intermediate Similarity	NPC185915
0.7949	Intermediate Similarity	NPC128951
0.7949	Intermediate Similarity	NPC192046
0.7949	Intermediate Similarity	NPC302578
0.7949	Intermediate Similarity	NPC477227
0.7931	Intermediate Similarity	NPC30687
0.7927	Intermediate Similarity	NPC474156
0.7917	Intermediate Similarity	NPC472946
0.7907	Intermediate Similarity	NPC59006
0.7907	Intermediate Similarity	NPC473066
0.7901	Intermediate Similarity	NPC60018
0.7901	Intermediate Similarity	NPC477286
0.7901	Intermediate Similarity	NPC470611
0.7901	Intermediate Similarity	NPC154043
0.7901	Intermediate Similarity	NPC202688
0.7901	Intermediate Similarity	NPC216800
0.7901	Intermediate Similarity	NPC286719
0.7895	Intermediate Similarity	NPC472341
0.7895	Intermediate Similarity	NPC470610
0.7895	Intermediate Similarity	NPC153719
0.7895	Intermediate Similarity	NPC253805
0.7895	Intermediate Similarity	NPC473238
0.7882	Intermediate Similarity	NPC82955
0.7882	Intermediate Similarity	NPC228059
0.7857	Intermediate Similarity	NPC202937
0.7857	Intermediate Similarity	NPC140446
0.7857	Intermediate Similarity	NPC5943
0.7857	Intermediate Similarity	NPC43912
0.7848	Intermediate Similarity	NPC67657
0.7848	Intermediate Similarity	NPC18857
0.7831	Intermediate Similarity	NPC266651
0.7792	Intermediate Similarity	NPC304499
0.7792	Intermediate Similarity	NPC472944
0.7792	Intermediate Similarity	NPC48795
0.7792	Intermediate Similarity	NPC472945
0.7778	Intermediate Similarity	NPC94897
0.7778	Intermediate Similarity	NPC211049
0.7778	Intermediate Similarity	NPC190940
0.7765	Intermediate Similarity	NPC471221
0.7765	Intermediate Similarity	NPC476435
0.7765	Intermediate Similarity	NPC473436
0.7763	Intermediate Similarity	NPC157422
0.7763	Intermediate Similarity	NPC195530
0.7763	Intermediate Similarity	NPC100586
0.7763	Intermediate Similarity	NPC109457
0.7763	Intermediate Similarity	NPC127094
0.775	Intermediate Similarity	NPC476367
0.775	Intermediate Similarity	NPC72755
0.7738	Intermediate Similarity	NPC471240
0.7738	Intermediate Similarity	NPC131365
0.7738	Intermediate Similarity	NPC268633
0.7733	Intermediate Similarity	NPC470830
0.7733	Intermediate Similarity	NPC299948
0.7733	Intermediate Similarity	NPC241085
0.7727	Intermediate Similarity	NPC175
0.7711	Intermediate Similarity	NPC86238
0.7703	Intermediate Similarity	NPC476928
0.7701	Intermediate Similarity	NPC229801
0.7701	Intermediate Similarity	NPC307167
0.7701	Intermediate Similarity	NPC210759
0.7692	Intermediate Similarity	NPC186851
0.7683	Intermediate Similarity	NPC2096
0.7683	Intermediate Similarity	NPC208912
0.7681	Intermediate Similarity	NPC236588
0.7681	Intermediate Similarity	NPC135438
0.7674	Intermediate Similarity	NPC20822
0.7674	Intermediate Similarity	NPC131466
0.7671	Intermediate Similarity	NPC260116
0.7662	Intermediate Similarity	NPC123122
0.7654	Intermediate Similarity	NPC474714
0.7654	Intermediate Similarity	NPC471216
0.7654	Intermediate Similarity	NPC471217
0.7647	Intermediate Similarity	NPC472396
0.764	Intermediate Similarity	NPC473067
0.764	Intermediate Similarity	NPC17336
0.764	Intermediate Similarity	NPC473065
0.764	Intermediate Similarity	NPC473064
0.7632	Intermediate Similarity	NPC63588
0.7632	Intermediate Similarity	NPC192192
0.7632	Intermediate Similarity	NPC282454
0.7632	Intermediate Similarity	NPC251201
0.7632	Intermediate Similarity	NPC232925
0.7625	Intermediate Similarity	NPC52755
0.7619	Intermediate Similarity	NPC232044
0.7619	Intermediate Similarity	NPC273290
0.7614	Intermediate Similarity	NPC323231
0.7614	Intermediate Similarity	NPC256104
0.7614	Intermediate Similarity	NPC182740
0.7614	Intermediate Similarity	NPC224003
0.7614	Intermediate Similarity	NPC311246
0.7614	Intermediate Similarity	NPC122083
0.7614	Intermediate Similarity	NPC167644
0.7614	Intermediate Similarity	NPC171741
0.7614	Intermediate Similarity	NPC18724
0.7614	Intermediate Similarity	NPC211845
0.7614	Intermediate Similarity	NPC470623
0.76	Intermediate Similarity	NPC474756
0.759	Intermediate Similarity	NPC475820
0.759	Intermediate Similarity	NPC213737
0.759	Intermediate Similarity	NPC227170
0.759	Intermediate Similarity	NPC474253
0.759	Intermediate Similarity	NPC474346
0.759	Intermediate Similarity	NPC474284
0.7586	Intermediate Similarity	NPC279329
0.7586	Intermediate Similarity	NPC473542
0.7571	Intermediate Similarity	NPC47663
0.7564	Intermediate Similarity	NPC166250
0.7561	Intermediate Similarity	NPC71541
0.7561	Intermediate Similarity	NPC119922
0.7561	Intermediate Similarity	NPC116320
0.7561	Intermediate Similarity	NPC73515
0.7558	Intermediate Similarity	NPC281004
0.7558	Intermediate Similarity	NPC477614
0.7558	Intermediate Similarity	NPC56777

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 NPC472952 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	4128
0.2-0.3	3141
0.3-0.4	846
0.4-0.5	329
0.5-0.6	254
0.6-0.7	44
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7973	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD371	Approved
0.7229	Intermediate Similarity	NPD6928	Phase 2
0.7222	Intermediate Similarity	NPD8171	Discontinued
0.6962	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1811	Approved
0.6914	Remote Similarity	NPD1810	Approved
0.6786	Remote Similarity	NPD6115	Approved
0.6786	Remote Similarity	NPD6118	Approved
0.6786	Remote Similarity	NPD6114	Approved
0.6786	Remote Similarity	NPD6697	Approved
0.675	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD6116	Phase 1
0.6628	Remote Similarity	NPD7525	Registered
0.6627	Remote Similarity	NPD3703	Phase 2
0.6569	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6117	Approved
0.6543	Remote Similarity	NPD2686	Approved
0.6543	Remote Similarity	NPD2687	Approved
0.6543	Remote Similarity	NPD2254	Approved
0.65	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7524	Approved
0.6463	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1700	Approved
0.6333	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7645	Phase 2
0.6311	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.631	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD384	Approved
0.6232	Remote Similarity	NPD385	Approved
0.6222	Remote Similarity	NPD6695	Phase 3
0.6222	Remote Similarity	NPD3669	Approved
0.6222	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4159	Approved
0.619	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7991	Discontinued
0.6145	Remote Similarity	NPD4245	Approved
0.6145	Remote Similarity	NPD4244	Approved
0.6125	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD5360	Phase 3
0.6098	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD386	Approved
0.6087	Remote Similarity	NPD388	Approved
0.604	Remote Similarity	NPD5344	Discontinued
0.6024	Remote Similarity	NPD3698	Phase 2
0.6019	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD4225	Approved
0.5977	Remote Similarity	NPD6933	Approved
0.5957	Remote Similarity	NPD7750	Discontinued
0.5952	Remote Similarity	NPD4789	Approved
0.5946	Remote Similarity	NPD7328	Approved
0.5946	Remote Similarity	NPD7327	Approved
0.5941	Remote Similarity	NPD7640	Approved
0.5941	Remote Similarity	NPD7639	Approved
0.5938	Remote Similarity	NPD3168	Discontinued
0.5938	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6700	Approved
0.5905	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6412	Phase 2
0.5904	Remote Similarity	NPD6705	Phase 1
0.5893	Remote Similarity	NPD7516	Approved
0.5889	Remote Similarity	NPD6931	Approved
0.5889	Remote Similarity	NPD6930	Phase 2
0.5876	Remote Similarity	NPD6702	Approved
0.5876	Remote Similarity	NPD6703	Approved
0.5876	Remote Similarity	NPD8034	Phase 2
0.5876	Remote Similarity	NPD8035	Phase 2
0.5862	Remote Similarity	NPD6942	Approved
0.5862	Remote Similarity	NPD7339	Approved
0.5862	Remote Similarity	NPD3702	Approved
0.5851	Remote Similarity	NPD8308	Discontinued
0.5843	Remote Similarity	NPD3671	Phase 1
0.5841	Remote Similarity	NPD8377	Approved
0.5841	Remote Similarity	NPD6054	Approved
0.5841	Remote Similarity	NPD6059	Approved
0.5841	Remote Similarity	NPD8294	Approved
0.5825	Remote Similarity	NPD7632	Discontinued
0.5795	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD8380	Approved
0.5789	Remote Similarity	NPD8296	Approved
0.5789	Remote Similarity	NPD8379	Approved
0.5789	Remote Similarity	NPD8335	Approved
0.5789	Remote Similarity	NPD8033	Approved
0.5789	Remote Similarity	NPD8378	Approved
0.5778	Remote Similarity	NPD6929	Approved
0.5766	Remote Similarity	NPD6940	Discontinued
0.5747	Remote Similarity	NPD6924	Approved
0.5747	Remote Similarity	NPD6926	Approved
0.5745	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6370	Approved
0.573	Remote Similarity	NPD6932	Approved
0.5727	Remote Similarity	NPD4632	Approved
0.5714	Remote Similarity	NPD4748	Discontinued
0.5714	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7087	Discontinued
0.5714	Remote Similarity	NPD7509	Discontinued
0.5714	Remote Similarity	NPD2267	Suspended
0.5702	Remote Similarity	NPD6319	Approved
0.5701	Remote Similarity	NPD8174	Phase 2
0.5701	Remote Similarity	NPD6686	Approved
0.5698	Remote Similarity	NPD4758	Discontinued
0.5698	Remote Similarity	NPD5777	Approved
0.5667	Remote Similarity	NPD5364	Discontinued
0.566	Remote Similarity	NPD6402	Approved
0.566	Remote Similarity	NPD6008	Approved
0.566	Remote Similarity	NPD7128	Approved
0.566	Remote Similarity	NPD5739	Approved
0.566	Remote Similarity	NPD6675	Approved
0.5652	Remote Similarity	NPD6921	Approved
0.5652	Remote Similarity	NPD6015	Approved
0.5652	Remote Similarity	NPD6016	Approved
0.5652	Remote Similarity	NPD1779	Approved
0.5652	Remote Similarity	NPD1780	Approved
0.5652	Remote Similarity	NPD7503	Approved
0.5641	Remote Similarity	NPD7492	Approved
0.5636	Remote Similarity	NPD8297	Approved
0.5631	Remote Similarity	NPD6648	Approved
0.5625	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD6683	Phase 2
0.5603	Remote Similarity	NPD5988	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