NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	734.26
Volume:	696.87
LogP:	2.78
LogD:	1.18
LogS:	-4.269
# Rotatable Bonds:	0
TPSA:	212.42
# H-Bond Aceptor:	14
# H-Bond Donor:	4
# Rings:	10
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.157
Synthetic Accessibility Score:	6.836
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.34
MDCK Permeability:	8.220286690630019e-05
Pgp-inhibitor:	0.895
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.846
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	43.011268615722656%
Volume Distribution (VD):	0.424
Pgp-substrate:	43.298736572265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.61
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.762
CYP3A4-substrate:	0.641

ADMET: Excretion

Clearance (CL):	1.665
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.504
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.536
Carcinogencity:	0.332
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC476824

Natural Product ID:	NPC476824
*Common Name:**	(1S,2S,4S,5S,7R,8S,9R,10S,16R,28E,33S,34S,36S,37R)-4,9,10,33-tetrahydroxy-1,8,13,28-tetramethyl-11,17,21,26,31-pentaoxadecacyclo[17.17.3.14,8.02,16.05,7.010,14.016,39.033,37.034,36.015,40]tetraconta-13,15(40),19(39),28-tetraene-12,18,22,25,30-pentone
IUPAC Name:	(1S,2S,4S,5S,7R,8S,9R,10S,16R,28E,33S,34S,36S,37R)-4,9,10,33-tetrahydroxy-1,8,13,28-tetramethyl-11,17,21,26,31-pentaoxadecacyclo[17.17.3.14,8.02,16.05,7.010,14.016,39.033,37.034,36.015,40]tetraconta-13,15(40),19(39),28-tetraene-12,18,22,25,30-pentone
Synonyms:
Standard InCHIKey:	SHDVXCYXBYXGAR-SALMQSNDSA-N
Standard InCHI:	InChI=1S/C39H42O14/c1-15-7-27(42)51-14-37(47)22-8-19(22)34(3)23(37)10-18-17(13-50-26(41)6-5-25(40)49-12-15)32(44)52-38(18)24(34)11-36(46)21-9-20(21)35(4)30(36)29(38)28-16(2)31(43)53-39(28,48)33(35)45/h7,19-24,33,45-48H,5-6,8-14H2,1-4H3/b15-7+/t19-,20+,21-,22-,23+,24-,33+,34-,35-,36-,37-,38-,39-/m0/s1
SMILES:	C/C/1=C\C(=O)OC[C@@]2([C@H]3C[C@@H]3[C@]4([C@H]2CC5=C(COC(=O)CCC(=O)OC1)C(=O)O[C@]56[C@H]4C[C@@]7([C@H]8C[C@H]8[C@]9(C7=C6C1=C(C(=O)O[C@@]1([C@@H]9O)O)C)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44445574
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO14995	Chloranthus spicatus	Species	Chloranthaceae	Eukaryota	whole plant	n.a.	n.a.	PMID[18044839]
NPO14995	Chloranthus spicatus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14995	Chloranthus spicatus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14995	Chloranthus spicatus	Species	Chloranthaceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	68	nM	PMID[18044839]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	68	nM	PMID[18044839]

☑ 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 NPC476824 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	295
0.1-0.2	1646
0.2-0.3	4951
0.3-0.4	9806
0.4-0.5	12934
0.5-0.6	8030
0.6-0.7	4292
0.7-0.8	686
0.8-0.85	25
0.85-0.9	11
0.9-0.95	8
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC327664
0.9917	High Similarity	NPC470427
0.9917	High Similarity	NPC476097
0.9836	High Similarity	NPC60150
0.9836	High Similarity	NPC192334
0.9754	High Similarity	NPC24599
0.9669	High Similarity	NPC134902
0.959	High Similarity	NPC254823
0.95	High Similarity	NPC226049
0.9417	High Similarity	NPC84865
0.9174	High Similarity	NPC27335
0.9147	High Similarity	NPC476825
0.9077	High Similarity	NPC25887
0.9008	High Similarity	NPC470426
0.8682	High Similarity	NPC469674
0.8682	High Similarity	NPC469673
0.8672	High Similarity	NPC241935
0.8672	High Similarity	NPC279478
0.8615	High Similarity	NPC476823
0.8605	High Similarity	NPC34963
0.8538	High Similarity	NPC58029
0.8527	High Similarity	NPC196921
0.8527	High Similarity	NPC220757
0.845	Intermediate Similarity	NPC35109
0.8217	Intermediate Similarity	NPC15095
0.8217	Intermediate Similarity	NPC63186
0.8016	Intermediate Similarity	NPC203862
0.7969	Intermediate Similarity	NPC17938
0.7955	Intermediate Similarity	NPC311534
0.7937	Intermediate Similarity	NPC470075
0.7923	Intermediate Similarity	NPC129992
0.7891	Intermediate Similarity	NPC44899
0.7891	Intermediate Similarity	NPC304260
0.7891	Intermediate Similarity	NPC5883
0.7891	Intermediate Similarity	NPC29639
0.7879	Intermediate Similarity	NPC287423
0.7874	Intermediate Similarity	NPC93883
0.7863	Intermediate Similarity	NPC8374
0.7857	Intermediate Similarity	NPC106446
0.7846	Intermediate Similarity	NPC269642
0.7846	Intermediate Similarity	NPC115349
0.7846	Intermediate Similarity	NPC470265
0.7846	Intermediate Similarity	NPC23786
0.7829	Intermediate Similarity	NPC107607
0.7812	Intermediate Similarity	NPC218093
0.7795	Intermediate Similarity	NPC5311
0.7795	Intermediate Similarity	NPC193382
0.7795	Intermediate Similarity	NPC310341
0.7795	Intermediate Similarity	NPC199428
0.7795	Intermediate Similarity	NPC99620
0.7778	Intermediate Similarity	NPC231240
0.7769	Intermediate Similarity	NPC67569
0.7769	Intermediate Similarity	NPC231518
0.7769	Intermediate Similarity	NPC46570
0.7769	Intermediate Similarity	NPC40749
0.7769	Intermediate Similarity	NPC85742
0.7769	Intermediate Similarity	NPC475219
0.7761	Intermediate Similarity	NPC231529
0.7761	Intermediate Similarity	NPC473593
0.7752	Intermediate Similarity	NPC55532
0.7752	Intermediate Similarity	NPC292467
0.7752	Intermediate Similarity	NPC30483
0.7752	Intermediate Similarity	NPC236973
0.7752	Intermediate Similarity	NPC469756
0.7752	Intermediate Similarity	NPC291820
0.7752	Intermediate Similarity	NPC268326
0.7752	Intermediate Similarity	NPC32177
0.7752	Intermediate Similarity	NPC470897
0.7752	Intermediate Similarity	NPC153085
0.7752	Intermediate Similarity	NPC81222
0.7744	Intermediate Similarity	NPC42399
0.7744	Intermediate Similarity	NPC117702
0.7744	Intermediate Similarity	NPC469757
0.7744	Intermediate Similarity	NPC471357
0.7744	Intermediate Similarity	NPC146456
0.7734	Intermediate Similarity	NPC471355
0.7734	Intermediate Similarity	NPC87250
0.7734	Intermediate Similarity	NPC158344
0.7734	Intermediate Similarity	NPC244402
0.7734	Intermediate Similarity	NPC473852
0.7734	Intermediate Similarity	NPC27507
0.7734	Intermediate Similarity	NPC243196
0.7734	Intermediate Similarity	NPC142066
0.7734	Intermediate Similarity	NPC471351
0.7734	Intermediate Similarity	NPC309034
0.7734	Intermediate Similarity	NPC50305
0.7734	Intermediate Similarity	NPC34390
0.7734	Intermediate Similarity	NPC157376
0.7734	Intermediate Similarity	NPC471354
0.7734	Intermediate Similarity	NPC196429
0.7734	Intermediate Similarity	NPC84987
0.7734	Intermediate Similarity	NPC77319
0.7734	Intermediate Similarity	NPC152615
0.7734	Intermediate Similarity	NPC474418
0.7734	Intermediate Similarity	NPC99728
0.7734	Intermediate Similarity	NPC290693
0.7734	Intermediate Similarity	NPC471353
0.7724	Intermediate Similarity	NPC472820
0.7721	Intermediate Similarity	NPC88668
0.7721	Intermediate Similarity	NPC316915
0.7717	Intermediate Similarity	NPC84949
0.7717	Intermediate Similarity	NPC31354
0.7717	Intermediate Similarity	NPC471633
0.7717	Intermediate Similarity	NPC69576
0.771	Intermediate Similarity	NPC88326
0.771	Intermediate Similarity	NPC193893
0.771	Intermediate Similarity	NPC107493
0.771	Intermediate Similarity	NPC153700
0.7705	Intermediate Similarity	NPC473543
0.7705	Intermediate Similarity	NPC475585
0.7705	Intermediate Similarity	NPC161775
0.7705	Intermediate Similarity	NPC473577
0.7705	Intermediate Similarity	NPC474550
0.7704	Intermediate Similarity	NPC173347
0.7692	Intermediate Similarity	NPC474370
0.7692	Intermediate Similarity	NPC475556
0.7692	Intermediate Similarity	NPC475629
0.7692	Intermediate Similarity	NPC72260
0.7687	Intermediate Similarity	NPC470850
0.7687	Intermediate Similarity	NPC473888
0.768	Intermediate Similarity	NPC177047
0.7676	Intermediate Similarity	NPC471172
0.7674	Intermediate Similarity	NPC83287
0.7674	Intermediate Similarity	NPC475372
0.7669	Intermediate Similarity	NPC174367
0.7669	Intermediate Similarity	NPC47113
0.7664	Intermediate Similarity	NPC478072
0.7664	Intermediate Similarity	NPC471234
0.7661	Intermediate Similarity	NPC88701
0.766	Intermediate Similarity	NPC48414
0.766	Intermediate Similarity	NPC5153
0.7656	Intermediate Similarity	NPC138372
0.7656	Intermediate Similarity	NPC106228
0.7652	Intermediate Similarity	NPC469789
0.7652	Intermediate Similarity	NPC27363
0.7652	Intermediate Similarity	NPC41129
0.7642	Intermediate Similarity	NPC472818
0.7642	Intermediate Similarity	NPC119855
0.7642	Intermediate Similarity	NPC475290
0.7642	Intermediate Similarity	NPC470980
0.7642	Intermediate Similarity	NPC220217
0.7638	Intermediate Similarity	NPC471204
0.7638	Intermediate Similarity	NPC264153
0.7634	Intermediate Similarity	NPC475419
0.7634	Intermediate Similarity	NPC314535
0.7634	Intermediate Similarity	NPC233500
0.7634	Intermediate Similarity	NPC129434
0.7634	Intermediate Similarity	NPC474908
0.7634	Intermediate Similarity	NPC120390
0.7634	Intermediate Similarity	NPC470418
0.7634	Intermediate Similarity	NPC475590
0.7634	Intermediate Similarity	NPC173555
0.7634	Intermediate Similarity	NPC312481
0.763	Intermediate Similarity	NPC104382
0.763	Intermediate Similarity	NPC219085
0.763	Intermediate Similarity	NPC70542
0.763	Intermediate Similarity	NPC469752
0.763	Intermediate Similarity	NPC180079
0.763	Intermediate Similarity	NPC6108
0.763	Intermediate Similarity	NPC476966
0.763	Intermediate Similarity	NPC197707
0.763	Intermediate Similarity	NPC471407
0.763	Intermediate Similarity	NPC251866
0.763	Intermediate Similarity	NPC89514
0.763	Intermediate Similarity	NPC469755
0.763	Intermediate Similarity	NPC471361
0.763	Intermediate Similarity	NPC284406
0.763	Intermediate Similarity	NPC469754
0.763	Intermediate Similarity	NPC471360
0.763	Intermediate Similarity	NPC471359
0.763	Intermediate Similarity	NPC86159
0.763	Intermediate Similarity	NPC469751
0.763	Intermediate Similarity	NPC9499
0.763	Intermediate Similarity	NPC17896
0.763	Intermediate Similarity	NPC470880
0.763	Intermediate Similarity	NPC469753
0.763	Intermediate Similarity	NPC471352
0.763	Intermediate Similarity	NPC10823
0.763	Intermediate Similarity	NPC471358
0.7623	Intermediate Similarity	NPC473694
0.7623	Intermediate Similarity	NPC474124
0.7623	Intermediate Similarity	NPC475334
0.7623	Intermediate Similarity	NPC475623
0.7623	Intermediate Similarity	NPC472821
0.7623	Intermediate Similarity	NPC473523
0.7619	Intermediate Similarity	NPC470076
0.7615	Intermediate Similarity	NPC477071
0.7615	Intermediate Similarity	NPC475041
0.7615	Intermediate Similarity	NPC9674
0.7615	Intermediate Similarity	NPC219656
0.7615	Intermediate Similarity	NPC312536
0.7615	Intermediate Similarity	NPC329905
0.7615	Intermediate Similarity	NPC264954
0.7615	Intermediate Similarity	NPC305260
0.7615	Intermediate Similarity	NPC19028
0.7615	Intermediate Similarity	NPC270850
0.7612	Intermediate Similarity	NPC473253
0.7612	Intermediate Similarity	NPC240070
0.7612	Intermediate Similarity	NPC470882
0.7612	Intermediate Similarity	NPC473265

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 NPC476824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1814
0.2-0.3	4009
0.3-0.4	2123
0.4-0.5	586
0.5-0.6	269
0.6-0.7	97
0.7-0.8	7
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
0.7769	Intermediate Similarity	NPD8033	Approved
0.7692	Intermediate Similarity	NPD8377	Approved
0.7692	Intermediate Similarity	NPD8294	Approved
0.7674	Intermediate Similarity	NPD7328	Approved
0.7674	Intermediate Similarity	NPD7327	Approved
0.7634	Intermediate Similarity	NPD8379	Approved
0.7634	Intermediate Similarity	NPD8378	Approved
0.7634	Intermediate Similarity	NPD8296	Approved
0.7634	Intermediate Similarity	NPD8380	Approved
0.7634	Intermediate Similarity	NPD8335	Approved
0.763	Intermediate Similarity	NPD7319	Approved
0.7615	Intermediate Similarity	NPD7516	Approved
0.7537	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD7503	Approved
0.7462	Intermediate Similarity	NPD7115	Discovery
0.7236	Intermediate Similarity	NPD7640	Approved
0.7236	Intermediate Similarity	NPD7639	Approved
0.7226	Intermediate Similarity	NPD7078	Approved
0.7154	Intermediate Similarity	NPD4225	Approved
0.7154	Intermediate Similarity	NPD7638	Approved
0.7132	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8293	Discontinued
0.708	Intermediate Similarity	NPD7492	Approved
0.7054	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7736	Approved
0.7037	Intermediate Similarity	NPD6059	Approved
0.7037	Intermediate Similarity	NPD6054	Approved
0.7037	Intermediate Similarity	NPD6319	Approved
0.7029	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD6371	Approved
0.6985	Remote Similarity	NPD8513	Phase 3
0.6985	Remote Similarity	NPD8515	Approved
0.6985	Remote Similarity	NPD8516	Approved
0.6985	Remote Similarity	NPD8517	Approved
0.6977	Remote Similarity	NPD6686	Approved
0.6934	Remote Similarity	NPD6370	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD6373	Approved
0.6899	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6053	Discontinued
0.6894	Remote Similarity	NPD8297	Approved
0.688	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6015	Approved
0.6861	Remote Similarity	NPD6016	Approved
0.6846	Remote Similarity	NPD7320	Approved
0.6822	Remote Similarity	NPD6008	Approved
0.6818	Remote Similarity	NPD6649	Approved
0.6818	Remote Similarity	NPD6650	Approved
0.6812	Remote Similarity	NPD5988	Approved
0.6772	Remote Similarity	NPD5344	Discontinued
0.6769	Remote Similarity	NPD6412	Phase 2
0.6769	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6882	Approved
0.6738	Remote Similarity	NPD8074	Phase 3
0.6719	Remote Similarity	NPD7632	Discontinued
0.6716	Remote Similarity	NPD8133	Approved
0.6716	Remote Similarity	NPD4632	Approved
0.6693	Remote Similarity	NPD6648	Approved
0.6692	Remote Similarity	NPD6675	Approved
0.6692	Remote Similarity	NPD7128	Approved
0.6692	Remote Similarity	NPD6402	Approved
0.6692	Remote Similarity	NPD5739	Approved
0.6691	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7604	Phase 2
0.6643	Remote Similarity	NPD8328	Phase 3
0.6591	Remote Similarity	NPD6881	Approved
0.6591	Remote Similarity	NPD6899	Approved
0.6585	Remote Similarity	NPD7838	Discovery
0.6573	Remote Similarity	NPD6033	Approved
0.6567	Remote Similarity	NPD8130	Phase 1
0.6515	Remote Similarity	NPD5697	Approved
0.6515	Remote Similarity	NPD5701	Approved
0.6508	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7625	Phase 1
0.6493	Remote Similarity	NPD7102	Approved
0.6493	Remote Similarity	NPD4634	Approved
0.6493	Remote Similarity	NPD7290	Approved
0.6493	Remote Similarity	NPD6883	Approved
0.648	Remote Similarity	NPD6399	Phase 3
0.6449	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6869	Approved
0.6444	Remote Similarity	NPD6617	Approved
0.6444	Remote Similarity	NPD6847	Approved
0.6429	Remote Similarity	NPD6001	Approved
0.6418	Remote Similarity	NPD6012	Approved
0.6418	Remote Similarity	NPD6014	Approved
0.6418	Remote Similarity	NPD6013	Approved
0.6406	Remote Similarity	NPD6084	Phase 2
0.6406	Remote Similarity	NPD6083	Phase 2
0.64	Remote Similarity	NPD5281	Approved
0.64	Remote Similarity	NPD5284	Approved
0.6383	Remote Similarity	NPD5983	Phase 2
0.6378	Remote Similarity	NPD5695	Phase 3
0.6349	Remote Similarity	NPD5778	Approved
0.6349	Remote Similarity	NPD5779	Approved
0.6343	Remote Similarity	NPD6011	Approved
0.6343	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7524	Approved
0.6336	Remote Similarity	NPD5211	Phase 2
0.6327	Remote Similarity	NPD7260	Phase 2
0.6324	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6698	Approved
0.632	Remote Similarity	NPD46	Approved
0.6319	Remote Similarity	NPD6336	Discontinued
0.6294	Remote Similarity	NPD6067	Discontinued
0.6279	Remote Similarity	NPD4755	Approved
0.6279	Remote Similarity	NPD7902	Approved
0.627	Remote Similarity	NPD7983	Approved
0.6241	Remote Similarity	NPD5141	Approved
0.624	Remote Similarity	NPD6051	Approved
0.6231	Remote Similarity	NPD5696	Approved
0.623	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4202	Approved
0.6199	Remote Similarity	NPD7799	Discontinued
0.619	Remote Similarity	NPD5207	Approved
0.619	Remote Similarity	NPD5785	Approved
0.6183	Remote Similarity	NPD5286	Approved
0.6183	Remote Similarity	NPD4700	Approved
0.6183	Remote Similarity	NPD4696	Approved
0.6183	Remote Similarity	NPD5285	Approved
0.6179	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6845	Suspended
0.616	Remote Similarity	NPD6903	Approved
0.6149	Remote Similarity	NPD5956	Approved
0.6148	Remote Similarity	NPD6695	Phase 3
0.6143	Remote Similarity	NPD6274	Approved
0.6142	Remote Similarity	NPD6050	Approved
0.6142	Remote Similarity	NPD8035	Phase 2
0.6142	Remote Similarity	NPD6411	Approved
0.6142	Remote Similarity	NPD8034	Phase 2
0.6127	Remote Similarity	NPD7100	Approved
0.6127	Remote Similarity	NPD7101	Approved
0.6098	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.609	Remote Similarity	NPD5225	Approved
0.609	Remote Similarity	NPD5224	Approved
0.609	Remote Similarity	NPD5226	Approved
0.609	Remote Similarity	NPD4633	Approved
0.608	Remote Similarity	NPD7750	Discontinued
0.608	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD4768	Approved
0.6074	Remote Similarity	NPD4767	Approved
0.6063	Remote Similarity	NPD5692	Phase 3
0.6056	Remote Similarity	NPD6335	Approved
0.6047	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7748	Approved
0.6047	Remote Similarity	NPD7900	Approved
0.6045	Remote Similarity	NPD5175	Approved
0.6045	Remote Similarity	NPD5174	Approved
0.6042	Remote Similarity	NPD6908	Approved
0.6042	Remote Similarity	NPD6909	Approved
0.6042	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5693	Phase 1
0.6016	Remote Similarity	NPD5694	Approved
0.6015	Remote Similarity	NPD4159	Approved
0.6015	Remote Similarity	NPD5223	Approved
0.6013	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.5986	Remote Similarity	NPD6317	Approved
0.5985	Remote Similarity	NPD4730	Approved
0.5985	Remote Similarity	NPD4729	Approved
0.5984	Remote Similarity	NPD6101	Approved
0.5984	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD4753	Phase 2
0.5984	Remote Similarity	NPD5328	Approved
0.5954	Remote Similarity	NPD4697	Phase 3
0.5952	Remote Similarity	NPD4250	Approved
0.5952	Remote Similarity	NPD4251	Approved
0.5944	Remote Similarity	NPD6313	Approved
0.5944	Remote Similarity	NPD6314	Approved
0.5931	Remote Similarity	NPD6921	Approved
0.5926	Remote Similarity	NPD4754	Approved
0.5909	Remote Similarity	NPD5959	Approved
0.5906	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6930	Phase 2
0.5902	Remote Similarity	NPD6931	Approved
0.5902	Remote Similarity	NPD7525	Registered
0.5899	Remote Similarity	NPD5251	Approved
0.5899	Remote Similarity	NPD5250	Approved
0.5899	Remote Similarity	NPD5248	Approved
0.5899	Remote Similarity	NPD5247	Approved
0.5899	Remote Similarity	NPD5249	Phase 3
0.5891	Remote Similarity	NPD7515	Phase 2
0.5891	Remote Similarity	NPD6079	Approved
0.5878	Remote Similarity	NPD4629	Approved
0.5878	Remote Similarity	NPD5210	Approved
0.5873	Remote Similarity	NPD4249	Approved
0.5873	Remote Similarity	NPD4694	Approved
0.5873	Remote Similarity	NPD5279	Phase 3
0.5873	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD5280	Approved
0.5871	Remote Similarity	NPD6333	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