NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1126.56
Volume:	1095.036
LogP:	1.609
LogD:	0.909
LogS:	-2.87
# Rotatable Bonds:	16
TPSA:	367.81
# H-Bond Aceptor:	23
# H-Bond Donor:	12
# Rings:	8
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.047
Synthetic Accessibility Score:	7.047
Fsp3:	0.839
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:	-6.237
MDCK Permeability:	0.0002462704142089933
Pgp-inhibitor:	0.876
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.984
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	67.34593963623047%
Volume Distribution (VD):	0.28
Pgp-substrate:	8.524797439575195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.011

ADMET: Excretion

Clearance (CL):	0.565
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.137
Human Hepatotoxicity (H-HT):	0.411
Drug-inuced Liver Injury (DILI):	0.461
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.133
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.249

Download Data

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

Natural Product: NPC478154

Natural Product ID:	NPC478154
*Common Name:**	xanifolia-Y8
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-4,8-dihydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-9,10-bis[[(Z)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:	xanifolia-Y8
Standard InCHIKey:	RKXRAFFAJLEWCU-DMTBMMKBSA-N
Standard InCHI:	InChI=1S/C56H86O23/c1-11-24(3)46(69)78-43-44(79-47(70)25(4)12-2)56(23-59)27(19-51(43,5)6)26-13-14-30-52(7)17-16-33(55(10,71)31(52)15-18-53(30,8)54(26,9)20-32(56)60)74-50-42(77-49-38(65)36(63)34(61)28(21-57)72-49)40(39(66)41(76-50)45(67)68)75-48-37(64)35(62)29(22-58)73-48/h11-13,27-44,48-50,57-66,71H,14-23H2,1-10H3,(H,67,68)/b24-11-,25-12-/t27-,28+,29-,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,40-,41-,42+,43-,44-,48-,49-,50+,52+,53+,54+,55+,56-/m0/s1
SMILES:	C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@]5(C)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)C)O)CO)(C)C)OC(=O)/C(=C\C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44560531
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
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]

☑ 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
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	8900	nM	PMID[18549275]

☑ 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 NPC478154 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	313
0.1-0.2	1792
0.2-0.3	5019
0.3-0.4	8592
0.4-0.5	11241
0.5-0.6	7969
0.6-0.7	4603
0.7-0.8	2020
0.8-0.85	734
0.85-0.9	261
0.9-0.95	75
0.95-1	78

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC25998
0.9917	High Similarity	NPC478155
0.9917	High Similarity	NPC478151
0.9835	High Similarity	NPC478150
0.9835	High Similarity	NPC478153
0.9835	High Similarity	NPC478152
0.9752	High Similarity	NPC172374
0.9752	High Similarity	NPC45346
0.9752	High Similarity	NPC475377
0.9752	High Similarity	NPC329993
0.9752	High Similarity	NPC475167
0.9752	High Similarity	NPC476074
0.9752	High Similarity	NPC264566
0.9752	High Similarity	NPC134914
0.9752	High Similarity	NPC478064
0.9752	High Similarity	NPC301639
0.9752	High Similarity	NPC173435
0.9752	High Similarity	NPC478065
0.9752	High Similarity	NPC262796
0.975	High Similarity	NPC477193
0.975	High Similarity	NPC477192
0.975	High Similarity	NPC477191
0.975	High Similarity	NPC477194
0.9669	High Similarity	NPC472267
0.9669	High Similarity	NPC305793
0.9669	High Similarity	NPC82380
0.9669	High Similarity	NPC470913
0.9669	High Similarity	NPC141600
0.9669	High Similarity	NPC477077
0.9669	High Similarity	NPC477196
0.9669	High Similarity	NPC273878
0.9669	High Similarity	NPC269484
0.9669	High Similarity	NPC11577
0.9669	High Similarity	NPC252289
0.9669	High Similarity	NPC107536
0.9669	High Similarity	NPC88311
0.9669	High Similarity	NPC244296
0.9669	High Similarity	NPC477076
0.9669	High Similarity	NPC1314
0.9669	High Similarity	NPC252657
0.9669	High Similarity	NPC477079
0.9669	High Similarity	NPC280029
0.9669	High Similarity	NPC97918
0.9669	High Similarity	NPC470518
0.9669	High Similarity	NPC115656
0.9669	High Similarity	NPC9470
0.959	High Similarity	NPC476774
0.959	High Similarity	NPC271610
0.959	High Similarity	NPC476775
0.959	High Similarity	NPC476780
0.959	High Similarity	NPC477197
0.9587	High Similarity	NPC477075
0.9587	High Similarity	NPC475281
0.9587	High Similarity	NPC329923
0.9587	High Similarity	NPC477078
0.9512	High Similarity	NPC312650
0.9512	High Similarity	NPC277212
0.9512	High Similarity	NPC30279
0.9512	High Similarity	NPC71391
0.9512	High Similarity	NPC473918
0.9512	High Similarity	NPC476776
0.9512	High Similarity	NPC477195
0.9512	High Similarity	NPC178264
0.9512	High Similarity	NPC46823
0.9512	High Similarity	NPC192765
0.9508	High Similarity	NPC47995
0.9508	High Similarity	NPC265841
0.9508	High Similarity	NPC470912
0.9435	High Similarity	NPC225791
0.9365	High Similarity	NPC190065
0.9365	High Similarity	NPC141215
0.9365	High Similarity	NPC471089
0.936	High Similarity	NPC476777
0.936	High Similarity	NPC476778
0.9291	High Similarity	NPC140045
0.9291	High Similarity	NPC295885
0.9291	High Similarity	NPC596
0.9286	High Similarity	NPC262813
0.9286	High Similarity	NPC279915
0.9286	High Similarity	NPC110700
0.928	High Similarity	NPC476779
0.9268	High Similarity	NPC470475
0.9262	High Similarity	NPC285091
0.9256	High Similarity	NPC478066
0.9213	High Similarity	NPC251998
0.9174	High Similarity	NPC107966
0.9174	High Similarity	NPC235438
0.9174	High Similarity	NPC40775
0.9174	High Similarity	NPC249848
0.912	High Similarity	NPC43589
0.912	High Similarity	NPC222951
0.912	High Similarity	NPC311178
0.912	High Similarity	NPC300655
0.9113	High Similarity	NPC470476
0.9098	High Similarity	NPC262199
0.9098	High Similarity	NPC30735
0.9098	High Similarity	NPC202666
0.9098	High Similarity	NPC281148
0.9098	High Similarity	NPC471964
0.9098	High Similarity	NPC235405
0.9098	High Similarity	NPC14617
0.9098	High Similarity	NPC471961
0.9048	High Similarity	NPC475177
0.9048	High Similarity	NPC319719
0.9048	High Similarity	NPC322904
0.9048	High Similarity	NPC233223
0.9048	High Similarity	NPC324933
0.9048	High Similarity	NPC196874
0.9048	High Similarity	NPC473679
0.9048	High Similarity	NPC475444
0.9048	High Similarity	NPC183816
0.9032	High Similarity	NPC470780
0.9032	High Similarity	NPC470516
0.9024	High Similarity	NPC470477
0.9024	High Similarity	NPC23275
0.9024	High Similarity	NPC471963
0.9024	High Similarity	NPC471962
0.9024	High Similarity	NPC247315
0.9016	High Similarity	NPC471965
0.9016	High Similarity	NPC213952
0.9008	High Similarity	NPC236657
0.9008	High Similarity	NPC118440
0.896	High Similarity	NPC220838
0.896	High Similarity	NPC45606
0.8952	High Similarity	NPC470218
0.8943	High Similarity	NPC257211
0.8934	High Similarity	NPC11242
0.8934	High Similarity	NPC302887
0.8934	High Similarity	NPC222580
0.8934	High Similarity	NPC86222
0.8934	High Similarity	NPC159309
0.8934	High Similarity	NPC104372
0.8934	High Similarity	NPC22956
0.8934	High Similarity	NPC31838
0.8934	High Similarity	NPC223301
0.8934	High Similarity	NPC62725
0.8934	High Similarity	NPC301449
0.8934	High Similarity	NPC187618
0.8934	High Similarity	NPC297263
0.8934	High Similarity	NPC64715
0.8934	High Similarity	NPC75417
0.8934	High Similarity	NPC171544
0.8934	High Similarity	NPC114484
0.8926	High Similarity	NPC208381
0.8926	High Similarity	NPC469945
0.8926	High Similarity	NPC35405
0.8926	High Similarity	NPC6377
0.8926	High Similarity	NPC309780
0.8926	High Similarity	NPC11551
0.8926	High Similarity	NPC180550
0.8926	High Similarity	NPC473884
0.8926	High Similarity	NPC475171
0.8926	High Similarity	NPC39211
0.8926	High Similarity	NPC214484
0.8926	High Similarity	NPC157868
0.8926	High Similarity	NPC472949
0.8926	High Similarity	NPC114441
0.8926	High Similarity	NPC470914
0.8917	High Similarity	NPC224121
0.8889	High Similarity	NPC54614
0.8889	High Similarity	NPC309096
0.8871	High Similarity	NPC470922
0.8871	High Similarity	NPC33068
0.8862	High Similarity	NPC4749
0.8862	High Similarity	NPC80986
0.8862	High Similarity	NPC187290
0.8862	High Similarity	NPC236870
0.8862	High Similarity	NPC313110
0.8862	High Similarity	NPC10607
0.8862	High Similarity	NPC475591
0.8862	High Similarity	NPC131469
0.8862	High Similarity	NPC162574
0.8862	High Similarity	NPC21691
0.8852	High Similarity	NPC473645
0.8843	High Similarity	NPC286347
0.881	High Similarity	NPC472270
0.881	High Similarity	NPC472268
0.881	High Similarity	NPC295220
0.881	High Similarity	NPC23020
0.881	High Similarity	NPC472269
0.881	High Similarity	NPC475636
0.881	High Similarity	NPC112492
0.88	High Similarity	NPC469947
0.88	High Similarity	NPC181066
0.88	High Similarity	NPC284449
0.879	High Similarity	NPC302543
0.879	High Similarity	NPC258617
0.879	High Similarity	NPC200049
0.879	High Similarity	NPC44716
0.879	High Similarity	NPC283417
0.879	High Similarity	NPC2370
0.878	High Similarity	NPC31193
0.878	High Similarity	NPC242840
0.877	High Similarity	NPC192791
0.876	High Similarity	NPC473405
0.872	High Similarity	NPC160452
0.8699	High Similarity	NPC142151
0.8699	High Similarity	NPC153673
0.8699	High Similarity	NPC294112
0.8699	High Similarity	NPC476150

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 NPC478154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	1978
0.2-0.3	3942
0.3-0.4	1908
0.4-0.5	591
0.5-0.6	271
0.6-0.7	135
0.7-0.8	38
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9098	High Similarity	NPD8328	Phase 3
0.8607	High Similarity	NPD8295	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD7736	Approved
0.8168	Intermediate Similarity	NPD7319	Approved
0.8077	Intermediate Similarity	NPD7507	Approved
0.8047	Intermediate Similarity	NPD8513	Phase 3
0.8047	Intermediate Similarity	NPD8515	Approved
0.8047	Intermediate Similarity	NPD8517	Approved
0.8047	Intermediate Similarity	NPD8516	Approved
0.7969	Intermediate Similarity	NPD8377	Approved
0.7969	Intermediate Similarity	NPD8294	Approved
0.7951	Intermediate Similarity	NPD6686	Approved
0.792	Intermediate Similarity	NPD8133	Approved
0.7907	Intermediate Similarity	NPD8378	Approved
0.7907	Intermediate Similarity	NPD8380	Approved
0.7907	Intermediate Similarity	NPD8379	Approved
0.7907	Intermediate Similarity	NPD8335	Approved
0.7907	Intermediate Similarity	NPD8033	Approved
0.7907	Intermediate Similarity	NPD8296	Approved
0.7879	Intermediate Similarity	NPD8293	Discontinued
0.7846	Intermediate Similarity	NPD6370	Approved
0.7752	Intermediate Similarity	NPD7516	Approved
0.7742	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7492	Approved
0.7692	Intermediate Similarity	NPD6054	Approved
0.7674	Intermediate Similarity	NPD7328	Approved
0.7674	Intermediate Similarity	NPD7327	Approved
0.7669	Intermediate Similarity	NPD6616	Approved
0.7634	Intermediate Similarity	NPD7503	Approved
0.7612	Intermediate Similarity	NPD7078	Approved
0.7557	Intermediate Similarity	NPD6319	Approved
0.7557	Intermediate Similarity	NPD6059	Approved
0.752	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD6015	Approved
0.7444	Intermediate Similarity	NPD5988	Approved
0.7422	Intermediate Similarity	NPD8297	Approved
0.7422	Intermediate Similarity	NPD6882	Approved
0.7344	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6009	Approved
0.7328	Intermediate Similarity	NPD7115	Discovery
0.7302	Intermediate Similarity	NPD6412	Phase 2
0.7295	Intermediate Similarity	NPD4225	Approved
0.7226	Intermediate Similarity	NPD8074	Phase 3
0.7209	Intermediate Similarity	NPD6649	Approved
0.7209	Intermediate Similarity	NPD6650	Approved
0.7188	Intermediate Similarity	NPD6372	Approved
0.7188	Intermediate Similarity	NPD6373	Approved
0.7188	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7638	Approved
0.7132	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6881	Approved
0.7109	Intermediate Similarity	NPD6899	Approved
0.7099	Intermediate Similarity	NPD4632	Approved
0.7097	Intermediate Similarity	NPD7640	Approved
0.7097	Intermediate Similarity	NPD7639	Approved
0.7087	Intermediate Similarity	NPD6402	Approved
0.7087	Intermediate Similarity	NPD5739	Approved
0.7087	Intermediate Similarity	NPD6675	Approved
0.7087	Intermediate Similarity	NPD7128	Approved
0.7077	Intermediate Similarity	NPD8130	Phase 1
0.7073	Intermediate Similarity	NPD7902	Approved
0.705	Intermediate Similarity	NPD6033	Approved
0.7031	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6883	Approved
0.6985	Remote Similarity	NPD6921	Approved
0.6977	Remote Similarity	NPD7320	Approved
0.6967	Remote Similarity	NPD7748	Approved
0.6947	Remote Similarity	NPD6869	Approved
0.6947	Remote Similarity	NPD6847	Approved
0.6947	Remote Similarity	NPD6617	Approved
0.6923	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6012	Approved
0.6923	Remote Similarity	NPD6013	Approved
0.6899	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5701	Approved
0.6897	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7604	Phase 2
0.687	Remote Similarity	NPD4634	Approved
0.6861	Remote Similarity	NPD5983	Phase 2
0.6846	Remote Similarity	NPD6011	Approved
0.6829	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7900	Approved
0.6803	Remote Similarity	NPD7515	Phase 2
0.6788	Remote Similarity	NPD7799	Discontinued
0.6786	Remote Similarity	NPD6336	Discontinued
0.6746	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6274	Approved
0.6601	Remote Similarity	NPD7625	Phase 1
0.6594	Remote Similarity	NPD7100	Approved
0.6594	Remote Similarity	NPD7101	Approved
0.6589	Remote Similarity	NPD7632	Discontinued
0.6589	Remote Similarity	NPD5211	Phase 2
0.6565	Remote Similarity	NPD6008	Approved
0.6562	Remote Similarity	NPD5286	Approved
0.6562	Remote Similarity	NPD5285	Approved
0.6562	Remote Similarity	NPD4696	Approved
0.6552	Remote Similarity	NPD7260	Phase 2
0.6535	Remote Similarity	NPD4755	Approved
0.6535	Remote Similarity	NPD6083	Phase 2
0.6535	Remote Similarity	NPD6084	Phase 2
0.6525	Remote Similarity	NPD6067	Discontinued
0.6525	Remote Similarity	NPD7830	Approved
0.6525	Remote Similarity	NPD7829	Approved
0.6522	Remote Similarity	NPD6335	Approved
0.6512	Remote Similarity	NPD5344	Discontinued
0.6512	Remote Similarity	NPD8407	Phase 2
0.6503	Remote Similarity	NPD8448	Approved
0.6493	Remote Similarity	NPD6371	Approved
0.6489	Remote Similarity	NPD5141	Approved
0.6486	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD5956	Approved
0.6462	Remote Similarity	NPD4633	Approved
0.6462	Remote Similarity	NPD5225	Approved
0.6462	Remote Similarity	NPD5224	Approved
0.6462	Remote Similarity	NPD5226	Approved
0.6454	Remote Similarity	NPD8080	Discontinued
0.6452	Remote Similarity	NPD46	Approved
0.6452	Remote Similarity	NPD6698	Approved
0.6449	Remote Similarity	NPD6317	Approved
0.6434	Remote Similarity	NPD8451	Approved
0.6434	Remote Similarity	NPD4700	Approved
0.6433	Remote Similarity	NPD8368	Discontinued
0.6419	Remote Similarity	NPD8415	Approved
0.6412	Remote Similarity	NPD5175	Approved
0.6412	Remote Similarity	NPD5174	Approved
0.6403	Remote Similarity	NPD6313	Approved
0.6403	Remote Similarity	NPD6314	Approved
0.64	Remote Similarity	NPD8034	Phase 2
0.64	Remote Similarity	NPD8035	Phase 2
0.6397	Remote Similarity	NPD6053	Discontinued
0.6395	Remote Similarity	NPD6845	Suspended
0.6385	Remote Similarity	NPD5223	Approved
0.6383	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6908	Approved
0.6383	Remote Similarity	NPD6909	Approved
0.6377	Remote Similarity	NPD6868	Approved
0.637	Remote Similarity	NPD8391	Approved
0.637	Remote Similarity	NPD8390	Approved
0.637	Remote Similarity	NPD8392	Approved
0.6357	Remote Similarity	NPD5696	Approved
0.6343	Remote Similarity	NPD4730	Approved
0.6343	Remote Similarity	NPD4729	Approved
0.6341	Remote Similarity	NPD3573	Approved
0.6328	Remote Similarity	NPD5221	Approved
0.6328	Remote Similarity	NPD4697	Phase 3
0.6328	Remote Similarity	NPD5222	Approved
0.6328	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4767	Approved
0.6316	Remote Similarity	NPD4768	Approved
0.6294	Remote Similarity	NPD7642	Approved
0.6279	Remote Similarity	NPD5173	Approved
0.627	Remote Similarity	NPD7983	Approved
0.627	Remote Similarity	NPD6079	Approved
0.627	Remote Similarity	NPD6411	Approved
0.6268	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD8340	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD8342	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD8341	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD8299	Approved
0.624	Remote Similarity	NPD5328	Approved
0.6233	Remote Similarity	NPD8336	Approved
0.6233	Remote Similarity	NPD8337	Approved
0.6222	Remote Similarity	NPD5128	Approved
0.622	Remote Similarity	NPD6399	Phase 3
0.622	Remote Similarity	NPD5779	Approved
0.622	Remote Similarity	NPD8171	Discontinued
0.622	Remote Similarity	NPD5778	Approved
0.6201	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7838	Discovery
0.6183	Remote Similarity	NPD6648	Approved
0.618	Remote Similarity	NPD8435	Approved
0.6179	Remote Similarity	NPD1694	Approved
0.6174	Remote Similarity	NPD8338	Approved
0.6172	Remote Similarity	NPD5282	Discontinued
0.6165	Remote Similarity	NPD4754	Approved
0.616	Remote Similarity	NPD6672	Approved
0.616	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD8444	Approved
0.6142	Remote Similarity	NPD5693	Phase 1
0.6141	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3618	Phase 1
0.6111	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6101	Approved
0.6101	Remote Similarity	NPD7236	Approved
0.6099	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD8360	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