NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	952.5
Volume:	941.206
LogP:	3.493
LogD:	2.302
LogS:	-3.25
# Rotatable Bonds:	11
TPSA:	288.66
# H-Bond Aceptor:	18
# H-Bond Donor:	9
# Rings:	7
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.069
Synthetic Accessibility Score:	6.482
Fsp3:	0.857
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.844
MDCK Permeability:	0.00012500479351729155
Pgp-inhibitor:	0.957
Pgp-substrate:	0.4
Human Intestinal Absorption (HIA):	0.889
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	79.04446411132812%
Volume Distribution (VD):	0.411
Pgp-substrate:	8.348073959350586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.191
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	0.8
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.331
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.033
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC477077

Natural Product ID:	NPC477077
*Common Name:**	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-10-acetyloxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-10-acetyloxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:
Standard InCHIKey:	UWIBPMODOUWPBX-AJIDHCQLSA-N
Standard InCHI:	InChI=1S/C49H76O18/c1-12-21(2)41(61)67-39-38(63-23(4)51)44(5,6)19-25-24-13-14-27-46(9)17-16-28(45(7,8)26(46)15-18-47(27,10)48(24,11)36(57)37(58)49(25,39)20-50)64-43-35(32(55)31(54)34(65-43)40(59)60)66-42-33(56)30(53)29(52)22(3)62-42/h12-13,22,25-39,42-43,50,52-58H,14-20H2,1-11H3,(H,59,60)/b21-12-/t22-,25+,26+,27-,28+,29-,30+,31+,32+,33+,34+,35-,36+,37-,38+,39+,42-,43-,46+,47-,48+,49+/m1/s1
SMILES:	C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H]([C@@H]([C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O[C@@H]7[C@H]([C@H]([C@@H]([C@H](O7)C)O)O)O)C)C)C)O)O)CO)(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44583929
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[16872157]
NPO12661	Eryngium campestre	Species	Apiaceae	Eukaryota	roots	Balkesir-Edremit, Turkey	2003-AUG	PMID[16872157]
NPO12661	Eryngium campestre	Species	Apiaceae	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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	40	ug/ml	PMID[16872157]
NPT2	Others	Unspecified		IC50	=	40	ug/ml	PMID[16872157]

☑ 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 NPC477077 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	322
0.1-0.2	1889
0.2-0.3	4796
0.3-0.4	8013
0.4-0.5	12035
0.5-0.6	8491
0.6-0.7	4375
0.7-0.8	1933
0.8-0.85	318
0.85-0.9	310
0.9-0.95	123
0.95-1	92

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477079
1.0	High Similarity	NPC477076
1.0	High Similarity	NPC470913
0.9916	High Similarity	NPC477197
0.9915	High Similarity	NPC475281
0.9915	High Similarity	NPC477075
0.9915	High Similarity	NPC477078
0.9915	High Similarity	NPC477192
0.9915	High Similarity	NPC477191
0.9915	High Similarity	NPC329923
0.9915	High Similarity	NPC477193
0.9915	High Similarity	NPC477194
0.9833	High Similarity	NPC30279
0.9833	High Similarity	NPC192765
0.9833	High Similarity	NPC277212
0.9833	High Similarity	NPC71391
0.9833	High Similarity	NPC46823
0.9833	High Similarity	NPC178264
0.9833	High Similarity	NPC478153
0.9833	High Similarity	NPC478150
0.9833	High Similarity	NPC473918
0.9833	High Similarity	NPC478152
0.9832	High Similarity	NPC82380
0.9832	High Similarity	NPC115656
0.9832	High Similarity	NPC88311
0.9832	High Similarity	NPC470912
0.9832	High Similarity	NPC11577
0.9832	High Similarity	NPC269484
0.9832	High Similarity	NPC477196
0.9832	High Similarity	NPC107536
0.9832	High Similarity	NPC470518
0.9832	High Similarity	NPC252289
0.9832	High Similarity	NPC97918
0.9832	High Similarity	NPC1314
0.9832	High Similarity	NPC273878
0.9832	High Similarity	NPC244296
0.9832	High Similarity	NPC9470
0.9832	High Similarity	NPC252657
0.9832	High Similarity	NPC305793
0.9832	High Similarity	NPC472267
0.9832	High Similarity	NPC141600
0.9832	High Similarity	NPC280029
0.9752	High Similarity	NPC478151
0.9752	High Similarity	NPC225791
0.975	High Similarity	NPC45346
0.975	High Similarity	NPC264566
0.975	High Similarity	NPC475167
0.975	High Similarity	NPC271610
0.975	High Similarity	NPC476775
0.975	High Similarity	NPC475377
0.975	High Similarity	NPC476780
0.975	High Similarity	NPC478155
0.975	High Similarity	NPC134914
0.975	High Similarity	NPC476774
0.975	High Similarity	NPC262796
0.975	High Similarity	NPC25998
0.975	High Similarity	NPC173435
0.975	High Similarity	NPC478065
0.975	High Similarity	NPC478064
0.975	High Similarity	NPC476074
0.975	High Similarity	NPC172374
0.975	High Similarity	NPC329993
0.975	High Similarity	NPC301639
0.9669	High Similarity	NPC476776
0.9669	High Similarity	NPC312650
0.9669	High Similarity	NPC478154
0.9669	High Similarity	NPC477195
0.9667	High Similarity	NPC265841
0.9667	High Similarity	NPC47995
0.9512	High Similarity	NPC476778
0.9512	High Similarity	NPC476777
0.9435	High Similarity	NPC110700
0.9435	High Similarity	NPC279915
0.9431	High Similarity	NPC476779
0.9262	High Similarity	NPC470475
0.925	High Similarity	NPC262199
0.925	High Similarity	NPC478066
0.925	High Similarity	NPC14617
0.925	High Similarity	NPC471961
0.925	High Similarity	NPC471964
0.925	High Similarity	NPC202666
0.918	High Similarity	NPC470516
0.9174	High Similarity	NPC471962
0.9174	High Similarity	NPC471963
0.9174	High Similarity	NPC247315
0.9174	High Similarity	NPC23275
0.9167	High Similarity	NPC471965
0.9167	High Similarity	NPC213952
0.916	High Similarity	NPC236657
0.916	High Similarity	NPC118440
0.9134	High Similarity	NPC596
0.9106	High Similarity	NPC470476
0.9098	High Similarity	NPC285091
0.9091	High Similarity	NPC257211
0.9083	High Similarity	NPC31838
0.9083	High Similarity	NPC302887
0.9083	High Similarity	NPC86222
0.9083	High Similarity	NPC222580
0.9083	High Similarity	NPC114484
0.9083	High Similarity	NPC22956
0.9083	High Similarity	NPC64715
0.9083	High Similarity	NPC171544
0.9083	High Similarity	NPC223301
0.9083	High Similarity	NPC301449
0.9083	High Similarity	NPC104372
0.9083	High Similarity	NPC62725
0.9083	High Similarity	NPC297263
0.9083	High Similarity	NPC187618
0.9083	High Similarity	NPC75417
0.9083	High Similarity	NPC11242
0.9083	High Similarity	NPC159309
0.9076	High Similarity	NPC214484
0.9076	High Similarity	NPC469945
0.9076	High Similarity	NPC114441
0.9076	High Similarity	NPC39211
0.9076	High Similarity	NPC35405
0.9076	High Similarity	NPC11551
0.9076	High Similarity	NPC473884
0.9076	High Similarity	NPC472949
0.9076	High Similarity	NPC157868
0.9076	High Similarity	NPC6377
0.9076	High Similarity	NPC208381
0.9076	High Similarity	NPC180550
0.9076	High Similarity	NPC475171
0.9076	High Similarity	NPC309780
0.9068	High Similarity	NPC224121
0.9055	High Similarity	NPC141215
0.9055	High Similarity	NPC190065
0.9055	High Similarity	NPC471089
0.9016	High Similarity	NPC33068
0.9016	High Similarity	NPC470477
0.9008	High Similarity	NPC21691
0.9008	High Similarity	NPC4749
0.9008	High Similarity	NPC80986
0.9008	High Similarity	NPC187290
0.9008	High Similarity	NPC40775
0.9008	High Similarity	NPC107966
0.9008	High Similarity	NPC249848
0.9008	High Similarity	NPC236870
0.9008	High Similarity	NPC10607
0.9008	High Similarity	NPC162574
0.9008	High Similarity	NPC475591
0.9008	High Similarity	NPC235438
0.9008	High Similarity	NPC131469
0.9008	High Similarity	NPC313110
0.8992	High Similarity	NPC286347
0.8984	High Similarity	NPC295885
0.8984	High Similarity	NPC140045
0.8976	High Similarity	NPC262813
0.8943	High Similarity	NPC181066
0.8943	High Similarity	NPC469947
0.8943	High Similarity	NPC284449
0.8934	High Similarity	NPC302543
0.8934	High Similarity	NPC283417
0.8934	High Similarity	NPC281148
0.8934	High Similarity	NPC200049
0.8934	High Similarity	NPC258617
0.8934	High Similarity	NPC235405
0.8934	High Similarity	NPC30735
0.8934	High Similarity	NPC2370
0.8934	High Similarity	NPC44716
0.8926	High Similarity	NPC242840
0.8926	High Similarity	NPC31193
0.8917	High Similarity	NPC192791
0.8917	High Similarity	NPC470914
0.8908	High Similarity	NPC473405
0.8906	High Similarity	NPC251998
0.8871	High Similarity	NPC470780
0.8862	High Similarity	NPC160452
0.8843	High Similarity	NPC294112
0.8833	High Similarity	NPC470515
0.8833	High Similarity	NPC471548
0.8824	High Similarity	NPC44170
0.8824	High Similarity	NPC268954
0.881	High Similarity	NPC300655
0.881	High Similarity	NPC222951
0.881	High Similarity	NPC311178
0.881	High Similarity	NPC43589
0.88	High Similarity	NPC23020
0.88	High Similarity	NPC472268
0.88	High Similarity	NPC112492
0.88	High Similarity	NPC472269
0.88	High Similarity	NPC472270
0.879	High Similarity	NPC470218
0.879	High Similarity	NPC475368
0.877	High Similarity	NPC170084
0.877	High Similarity	NPC476204
0.876	High Similarity	NPC470517
0.876	High Similarity	NPC470915
0.876	High Similarity	NPC473401
0.876	High Similarity	NPC470911
0.875	High Similarity	NPC300419
0.875	High Similarity	NPC309433
0.874	High Similarity	NPC322904
0.874	High Similarity	NPC233223
0.874	High Similarity	NPC475444
0.874	High Similarity	NPC183816
0.874	High Similarity	NPC324933
0.874	High Similarity	NPC319719
0.874	High Similarity	NPC196874

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 NPC477077 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	2077
0.2-0.3	3712
0.3-0.4	1962
0.4-0.5	658
0.5-0.6	284
0.6-0.7	120
0.7-0.8	29
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.925	High Similarity	NPD8328	Phase 3
0.8908	High Similarity	NPD8295	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD7319	Approved
0.7939	Intermediate Similarity	NPD7736	Approved
0.7934	Intermediate Similarity	NPD6686	Approved
0.7923	Intermediate Similarity	NPD7507	Approved
0.7891	Intermediate Similarity	NPD8513	Phase 3
0.7891	Intermediate Similarity	NPD8517	Approved
0.7891	Intermediate Similarity	NPD8515	Approved
0.7891	Intermediate Similarity	NPD8033	Approved
0.7891	Intermediate Similarity	NPD8516	Approved
0.7869	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD8377	Approved
0.7812	Intermediate Similarity	NPD8294	Approved
0.776	Intermediate Similarity	NPD8133	Approved
0.7752	Intermediate Similarity	NPD8378	Approved
0.7752	Intermediate Similarity	NPD8296	Approved
0.7752	Intermediate Similarity	NPD8380	Approved
0.7752	Intermediate Similarity	NPD8335	Approved
0.7752	Intermediate Similarity	NPD8379	Approved
0.7597	Intermediate Similarity	NPD7516	Approved
0.7594	Intermediate Similarity	NPD8293	Discontinued
0.7557	Intermediate Similarity	NPD6370	Approved
0.7519	Intermediate Similarity	NPD7327	Approved
0.7519	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD7503	Approved
0.7444	Intermediate Similarity	NPD7492	Approved
0.7405	Intermediate Similarity	NPD6054	Approved
0.7405	Intermediate Similarity	NPD6319	Approved
0.7388	Intermediate Similarity	NPD6616	Approved
0.7333	Intermediate Similarity	NPD7078	Approved
0.7308	Intermediate Similarity	NPD7115	Discovery
0.728	Intermediate Similarity	NPD6412	Phase 2
0.7273	Intermediate Similarity	NPD4225	Approved
0.7273	Intermediate Similarity	NPD6059	Approved
0.7266	Intermediate Similarity	NPD8297	Approved
0.7266	Intermediate Similarity	NPD6882	Approved
0.7218	Intermediate Similarity	NPD6016	Approved
0.7218	Intermediate Similarity	NPD6015	Approved
0.719	Intermediate Similarity	NPD7902	Approved
0.7188	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6009	Approved
0.7164	Intermediate Similarity	NPD5988	Approved
0.7131	Intermediate Similarity	NPD7638	Approved
0.7083	Intermediate Similarity	NPD7748	Approved
0.708	Intermediate Similarity	NPD8074	Phase 3
0.7073	Intermediate Similarity	NPD7640	Approved
0.7073	Intermediate Similarity	NPD7639	Approved
0.7054	Intermediate Similarity	NPD6649	Approved
0.7054	Intermediate Similarity	NPD6650	Approved
0.7031	Intermediate Similarity	NPD6373	Approved
0.7031	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6372	Approved
0.6977	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6921	Approved
0.6953	Remote Similarity	NPD6881	Approved
0.6953	Remote Similarity	NPD6899	Approved
0.6947	Remote Similarity	NPD4632	Approved
0.6942	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7900	Approved
0.6929	Remote Similarity	NPD5739	Approved
0.6929	Remote Similarity	NPD6402	Approved
0.6929	Remote Similarity	NPD7128	Approved
0.6929	Remote Similarity	NPD6675	Approved
0.6923	Remote Similarity	NPD8130	Phase 1
0.6917	Remote Similarity	NPD7515	Phase 2
0.6875	Remote Similarity	NPD5697	Approved
0.6855	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6883	Approved
0.6846	Remote Similarity	NPD7290	Approved
0.6846	Remote Similarity	NPD7102	Approved
0.6822	Remote Similarity	NPD7320	Approved
0.6794	Remote Similarity	NPD6617	Approved
0.6794	Remote Similarity	NPD6869	Approved
0.6794	Remote Similarity	NPD6847	Approved
0.6786	Remote Similarity	NPD6033	Approved
0.6769	Remote Similarity	NPD6014	Approved
0.6769	Remote Similarity	NPD6012	Approved
0.6769	Remote Similarity	NPD6013	Approved
0.6744	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5701	Approved
0.6744	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7829	Approved
0.6739	Remote Similarity	NPD7604	Phase 2
0.6739	Remote Similarity	NPD7830	Approved
0.6718	Remote Similarity	NPD4634	Approved
0.6715	Remote Similarity	NPD5983	Phase 2
0.6694	Remote Similarity	NPD46	Approved
0.6694	Remote Similarity	NPD6698	Approved
0.6692	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7799	Discontinued
0.6644	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6336	Discontinued
0.6643	Remote Similarity	NPD7260	Phase 2
0.6614	Remote Similarity	NPD5344	Discontinued
0.6596	Remote Similarity	NPD8448	Approved
0.6589	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7632	Discontinued
0.6541	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8451	Approved
0.6509	Remote Similarity	NPD8368	Discontinued
0.6507	Remote Similarity	NPD8415	Approved
0.6504	Remote Similarity	NPD6411	Approved
0.6504	Remote Similarity	NPD7983	Approved
0.6471	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD7625	Phase 1
0.6466	Remote Similarity	NPD6371	Approved
0.6458	Remote Similarity	NPD8392	Approved
0.6458	Remote Similarity	NPD8391	Approved
0.6458	Remote Similarity	NPD8390	Approved
0.6452	Remote Similarity	NPD5778	Approved
0.6452	Remote Similarity	NPD5779	Approved
0.6449	Remote Similarity	NPD7101	Approved
0.6449	Remote Similarity	NPD7100	Approved
0.6434	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD8080	Discontinued
0.6423	Remote Similarity	NPD7838	Discovery
0.6412	Remote Similarity	NPD6008	Approved
0.6406	Remote Similarity	NPD4696	Approved
0.6406	Remote Similarity	NPD5285	Approved
0.6406	Remote Similarity	NPD5286	Approved
0.6395	Remote Similarity	NPD8407	Phase 2
0.6383	Remote Similarity	NPD7642	Approved
0.6383	Remote Similarity	NPD6067	Discontinued
0.6378	Remote Similarity	NPD4755	Approved
0.6378	Remote Similarity	NPD6083	Phase 2
0.6378	Remote Similarity	NPD6084	Phase 2
0.6377	Remote Similarity	NPD6335	Approved
0.6371	Remote Similarity	NPD8034	Phase 2
0.6371	Remote Similarity	NPD8035	Phase 2
0.637	Remote Similarity	NPD6845	Suspended
0.637	Remote Similarity	NPD6053	Discontinued
0.6357	Remote Similarity	NPD8444	Approved
0.635	Remote Similarity	NPD6868	Approved
0.6341	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6101	Approved
0.6338	Remote Similarity	NPD8299	Approved
0.6338	Remote Similarity	NPD8342	Approved
0.6338	Remote Similarity	NPD8340	Approved
0.6338	Remote Similarity	NPD8341	Approved
0.6336	Remote Similarity	NPD5141	Approved
0.6331	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6399	Phase 3
0.6311	Remote Similarity	NPD3573	Approved
0.6308	Remote Similarity	NPD5225	Approved
0.6308	Remote Similarity	NPD4633	Approved
0.6308	Remote Similarity	NPD5226	Approved
0.6308	Remote Similarity	NPD5224	Approved
0.6304	Remote Similarity	NPD6317	Approved
0.6299	Remote Similarity	NPD4697	Phase 3
0.6299	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5222	Approved
0.6299	Remote Similarity	NPD5221	Approved
0.6279	Remote Similarity	NPD6648	Approved
0.6279	Remote Similarity	NPD4700	Approved
0.6271	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5174	Approved
0.626	Remote Similarity	NPD5175	Approved
0.6259	Remote Similarity	NPD6314	Approved
0.6259	Remote Similarity	NPD6313	Approved
0.625	Remote Similarity	NPD8435	Approved
0.625	Remote Similarity	NPD5173	Approved
0.6241	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD6908	Approved
0.6241	Remote Similarity	NPD6909	Approved
0.624	Remote Similarity	NPD6079	Approved
0.6233	Remote Similarity	NPD5956	Approved
0.6231	Remote Similarity	NPD5223	Approved
0.622	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5328	Approved
0.621	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8336	Approved
0.6207	Remote Similarity	NPD8337	Approved
0.6202	Remote Similarity	NPD5696	Approved
0.6194	Remote Similarity	NPD4730	Approved
0.6194	Remote Similarity	NPD4729	Approved
0.6186	Remote Similarity	NPD7645	Phase 2
0.6172	Remote Similarity	NPD7839	Suspended
0.6165	Remote Similarity	NPD4767	Approved
0.6165	Remote Similarity	NPD4768	Approved
0.6158	Remote Similarity	NPD8361	Approved
0.6158	Remote Similarity	NPD8360	Approved
0.6149	Remote Similarity	NPD8338	Approved
0.6149	Remote Similarity	NPD8312	Approved
0.6149	Remote Similarity	NPD8313	Approved
0.6143	Remote Similarity	NPD7641	Discontinued
0.6136	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6672	Approved
0.6129	Remote Similarity	NPD5737	Approved
0.6127	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD5247	Approved
0.6103	Remote Similarity	NPD5248	Approved
0.6103	Remote Similarity	NPD5250	Approved
0.6103	Remote Similarity	NPD5249	Phase 3
0.6103	Remote Similarity	NPD5251	Approved
0.6098	Remote Similarity	NPD3618	Phase 1
0.6094	Remote Similarity	NPD5695	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