NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	926.49
Volume:	897.411
LogP:	3.267
LogD:	1.82
LogS:	-3.859
# Rotatable Bonds:	9
TPSA:	261.98
# H-Bond Aceptor:	18
# H-Bond Donor:	8
# Rings:	9
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.124
Synthetic Accessibility Score:	6.866
Fsp3:	0.936
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:	-5.83
MDCK Permeability:	0.0003270548186264932
Pgp-inhibitor:	0.086
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.662
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.508

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	73.65457916259766%
Volume Distribution (VD):	0.137
Pgp-substrate:	8.793285369873047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.904
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.425
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	0.659
Half-life (T1/2):	0.669

ADMET: Toxicity

hERG Blockers:	0.882
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.212
Rat Oral Acute Toxicity:	0.632
Maximum Recommended Daily Dose:	0.302
Skin Sensitization:	0.937
Carcinogencity:	0.3
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC477031

Natural Product ID:	NPC477031
*Common Name:**	[(2R,3R,4S,5R,6R)-3-hydroxy-6-[(1R,2S,4S,5'R,6S,7S,8S,9S,12S,13R,16S)-8-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-4,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]methyl acetate
IUPAC Name:	[(2R,3R,4S,5R,6R)-3-hydroxy-6-[(1R,2S,4S,5'R,6S,7S,8S,9S,12S,13R,16S)-8-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-4,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]methyl acetate
Synonyms:
Standard InCHIKey:	QDDSBAJXSRKHDX-SRXZHTBESA-N
Standard InCHI:	InChI=1S/C47H74O18/c1-20-10-15-46(58-18-20)23(4)47(56)31(65-46)17-29-27-9-8-25-16-26(11-13-44(25,6)28(27)12-14-45(29,47)7)61-43-40(64-42-38(55)36(53)33(50)22(3)60-42)39(34(51)30(62-43)19-57-24(5)48)63-41-37(54)35(52)32(49)21(2)59-41/h8,20-23,26-43,49-56H,9-19H2,1-7H3/t20-,21+,22+,23-,26+,27-,28+,29+,30-,31+,32+,33+,34-,35-,36-,37-,38-,39+,40-,41+,42+,43-,44+,45+,46+,47-/m1/s1
SMILES:	C[C@@H]1CC[C@]2([C@H]([C@]3([C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)COC(=O)C)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)O)C)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49799043
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal 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
NPO22180	Dracaena mannii	Species	Asparagaceae	Eukaryota	n.a.	stem	n.a.	PMID[18481024]
NPO22180	Dracaena mannii	Species	Asparagaceae	Eukaryota	stems	Yaound, village of Bangoua, near Bangangt	2007-APR	PMID[20553003]
NPO22180	Dracaena mannii	Species	Asparagaceae	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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	8540	nM	PMID[20553003]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	7600	nM	PMID[20553003]

☑ 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 NPC477031 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	263
0.1-0.2	1972
0.2-0.3	6814
0.3-0.4	13874
0.4-0.5	7986
0.5-0.6	5937
0.6-0.7	3382
0.7-0.8	1404
0.8-0.85	712
0.85-0.9	231
0.9-0.95	110
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC477808
0.963	High Similarity	NPC63609
0.9623	High Similarity	NPC124677
0.9623	High Similarity	NPC477028
0.9623	High Similarity	NPC477032
0.9623	High Similarity	NPC470748
0.9541	High Similarity	NPC477807
0.9439	High Similarity	NPC13193
0.9434	High Similarity	NPC470433
0.9434	High Similarity	NPC309278
0.9434	High Similarity	NPC477809
0.9434	High Similarity	NPC46190
0.9434	High Similarity	NPC244086
0.9434	High Similarity	NPC6806
0.9434	High Similarity	NPC194207
0.9434	High Similarity	NPC40440
0.9434	High Similarity	NPC249265
0.9434	High Similarity	NPC232054
0.9434	High Similarity	NPC218571
0.9434	High Similarity	NPC248746
0.9434	High Similarity	NPC42482
0.9434	High Similarity	NPC84956
0.9434	High Similarity	NPC150372
0.9434	High Similarity	NPC475333
0.9434	High Similarity	NPC95051
0.9434	High Similarity	NPC102016
0.9434	High Similarity	NPC22779
0.9434	High Similarity	NPC73243
0.9434	High Similarity	NPC171073
0.9434	High Similarity	NPC224098
0.9434	High Similarity	NPC208383
0.9434	High Similarity	NPC300557
0.9434	High Similarity	NPC475550
0.9369	High Similarity	NPC195560
0.9369	High Similarity	NPC229962
0.9358	High Similarity	NPC167183
0.9358	High Similarity	NPC32707
0.9352	High Similarity	NPC254255
0.9346	High Similarity	NPC222202
0.9346	High Similarity	NPC23808
0.9346	High Similarity	NPC269297
0.9346	High Similarity	NPC477811
0.9346	High Similarity	NPC87998
0.9346	High Similarity	NPC224314
0.934	High Similarity	NPC98696
0.934	High Similarity	NPC295980
0.9292	High Similarity	NPC43842
0.9286	High Similarity	NPC207243
0.9286	High Similarity	NPC198325
0.9286	High Similarity	NPC233391
0.9286	High Similarity	NPC50689
0.9279	High Similarity	NPC475357
0.9266	High Similarity	NPC79900
0.9259	High Similarity	NPC197231
0.9259	High Similarity	NPC475247
0.9259	High Similarity	NPC294129
0.9259	High Similarity	NPC476547
0.9245	High Similarity	NPC283829
0.9245	High Similarity	NPC94272
0.9245	High Similarity	NPC305423
0.9245	High Similarity	NPC230507
0.9245	High Similarity	NPC161676
0.9245	High Similarity	NPC470432
0.9245	High Similarity	NPC14704
0.9245	High Similarity	NPC113044
0.9211	High Similarity	NPC295133
0.9211	High Similarity	NPC106589
0.9211	High Similarity	NPC257207
0.9211	High Similarity	NPC202261
0.9196	High Similarity	NPC473633
0.9196	High Similarity	NPC476085
0.9182	High Similarity	NPC477810
0.9174	High Similarity	NPC42171
0.9174	High Similarity	NPC210569
0.9174	High Similarity	NPC32361
0.9174	High Similarity	NPC244431
0.9174	High Similarity	NPC19888
0.9174	High Similarity	NPC263359
0.9174	High Similarity	NPC31896
0.9167	High Similarity	NPC247037
0.9151	High Similarity	NPC474569
0.9151	High Similarity	NPC181845
0.9115	High Similarity	NPC475358
0.9115	High Similarity	NPC473566
0.9107	High Similarity	NPC475403
0.9107	High Similarity	NPC160888
0.9099	High Similarity	NPC146652
0.9091	High Similarity	NPC469347
0.9091	High Similarity	NPC144068
0.9091	High Similarity	NPC469348
0.9083	High Similarity	NPC114188
0.9074	High Similarity	NPC477027
0.9074	High Similarity	NPC306131
0.9074	High Similarity	NPC70204
0.9074	High Similarity	NPC475670
0.9074	High Similarity	NPC477026
0.9043	High Similarity	NPC160084
0.9043	High Similarity	NPC256983
0.9009	High Similarity	NPC11548
0.9	High Similarity	NPC308140
0.8991	High Similarity	NPC141433
0.8981	High Similarity	NPC476539
0.8981	High Similarity	NPC476538
0.8981	High Similarity	NPC476540
0.8981	High Similarity	NPC476541
0.8972	High Similarity	NPC26798
0.8972	High Similarity	NPC309448
0.8966	High Similarity	NPC473474
0.8957	High Similarity	NPC156789
0.8929	High Similarity	NPC212660
0.8929	High Similarity	NPC477030
0.8929	High Similarity	NPC477029
0.8919	High Similarity	NPC476693
0.8919	High Similarity	NPC476546
0.8909	High Similarity	NPC65167
0.8899	High Similarity	NPC302057
0.8889	High Similarity	NPC190395
0.8889	High Similarity	NPC226642
0.887	High Similarity	NPC249553
0.887	High Similarity	NPC182900
0.887	High Similarity	NPC475182
0.887	High Similarity	NPC476544
0.887	High Similarity	NPC476543
0.887	High Similarity	NPC476545
0.8839	High Similarity	NPC208832
0.8829	High Similarity	NPC112274
0.8807	High Similarity	NPC472988
0.8807	High Similarity	NPC38217
0.8807	High Similarity	NPC220427
0.8796	High Similarity	NPC473476
0.8796	High Similarity	NPC242748
0.8796	High Similarity	NPC473923
0.8793	High Similarity	NPC305771
0.8793	High Similarity	NPC74259
0.8793	High Similarity	NPC15918
0.8793	High Similarity	NPC474423
0.8793	High Similarity	NPC94072
0.8793	High Similarity	NPC169816
0.8783	High Similarity	NPC475187
0.8761	High Similarity	NPC279638
0.875	High Similarity	NPC51154
0.875	High Similarity	NPC307642
0.875	High Similarity	NPC476671
0.8739	High Similarity	NPC13190
0.8727	High Similarity	NPC154085
0.8727	High Similarity	NPC43976
0.8727	High Similarity	NPC296761
0.8727	High Similarity	NPC476835
0.8727	High Similarity	NPC125361
0.8727	High Similarity	NPC51925
0.8718	High Similarity	NPC208193
0.8718	High Similarity	NPC308262
0.8718	High Similarity	NPC117445
0.8716	High Similarity	NPC234160
0.8716	High Similarity	NPC63368
0.8716	High Similarity	NPC14946
0.8716	High Similarity	NPC208650
0.8707	High Similarity	NPC120390
0.8707	High Similarity	NPC475590
0.8707	High Similarity	NPC475419
0.8707	High Similarity	NPC474908
0.8704	High Similarity	NPC221562
0.8704	High Similarity	NPC85593
0.8704	High Similarity	NPC187400
0.8704	High Similarity	NPC31430
0.8704	High Similarity	NPC470885
0.8696	High Similarity	NPC161738
0.8692	High Similarity	NPC272015
0.8692	High Similarity	NPC154452
0.8684	High Similarity	NPC20979
0.8673	High Similarity	NPC473882
0.8644	High Similarity	NPC248202
0.8636	High Similarity	NPC6931
0.8636	High Similarity	NPC180183
0.8636	High Similarity	NPC246124
0.8636	High Similarity	NPC159005
0.8632	High Similarity	NPC193893
0.8624	High Similarity	NPC269627
0.8624	High Similarity	NPC160816
0.8624	High Similarity	NPC127801
0.8624	High Similarity	NPC208477
0.8624	High Similarity	NPC208594
0.8624	High Similarity	NPC194842
0.8624	High Similarity	NPC152584
0.8624	High Similarity	NPC69737
0.8624	High Similarity	NPC473199
0.8621	High Similarity	NPC107607
0.8621	High Similarity	NPC72260
0.8611	High Similarity	NPC475701
0.8609	High Similarity	NPC475632
0.8609	High Similarity	NPC10366
0.8609	High Similarity	NPC86020
0.8609	High Similarity	NPC476691
0.8609	High Similarity	NPC476692
0.8609	High Similarity	NPC218093
0.8598	High Similarity	NPC21064
0.8598	High Similarity	NPC121072
0.8596	High Similarity	NPC148965
0.8559	High Similarity	NPC476542
0.8547	High Similarity	NPC314535

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 NPC477031 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	2186
0.2-0.3	4362
0.3-0.4	1567
0.4-0.5	404
0.5-0.6	277
0.6-0.7	97
0.7-0.8	21
0.8-0.85	6
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8621	High Similarity	NPD8294	Approved
0.8621	High Similarity	NPD8377	Approved
0.8547	High Similarity	NPD8296	Approved
0.8547	High Similarity	NPD8335	Approved
0.8547	High Similarity	NPD8380	Approved
0.8547	High Similarity	NPD8378	Approved
0.8547	High Similarity	NPD8379	Approved
0.8547	High Similarity	NPD8033	Approved
0.8136	Intermediate Similarity	NPD7328	Approved
0.8136	Intermediate Similarity	NPD7327	Approved
0.8103	Intermediate Similarity	NPD8133	Approved
0.8067	Intermediate Similarity	NPD7516	Approved
0.7934	Intermediate Similarity	NPD7503	Approved
0.7895	Intermediate Similarity	NPD6412	Phase 2
0.7812	Intermediate Similarity	NPD8450	Suspended
0.7778	Intermediate Similarity	NPD8171	Discontinued
0.7734	Intermediate Similarity	NPD8449	Approved
0.7698	Intermediate Similarity	NPD7736	Approved
0.768	Intermediate Similarity	NPD7507	Approved
0.7619	Intermediate Similarity	NPD8293	Discontinued
0.75	Intermediate Similarity	NPD7319	Approved
0.7458	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6370	Approved
0.7414	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD8328	Phase 3
0.7323	Intermediate Similarity	NPD7492	Approved
0.7317	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD6059	Approved
0.728	Intermediate Similarity	NPD6054	Approved
0.7266	Intermediate Similarity	NPD6616	Approved
0.7227	Intermediate Similarity	NPD6686	Approved
0.7222	Intermediate Similarity	NPD8515	Approved
0.7222	Intermediate Similarity	NPD8517	Approved
0.7222	Intermediate Similarity	NPD8516	Approved
0.7209	Intermediate Similarity	NPD7078	Approved
0.7087	Intermediate Similarity	NPD6015	Approved
0.7087	Intermediate Similarity	NPD6016	Approved
0.7087	Intermediate Similarity	NPD8513	Phase 3
0.7049	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5988	Approved
0.7008	Intermediate Similarity	NPD6319	Approved
0.6992	Remote Similarity	NPD8297	Approved
0.6992	Remote Similarity	NPD6882	Approved
0.6977	Remote Similarity	NPD6067	Discontinued
0.6905	Remote Similarity	NPD6009	Approved
0.6842	Remote Similarity	NPD6399	Phase 3
0.6803	Remote Similarity	NPD7320	Approved
0.68	Remote Similarity	NPD4632	Approved
0.6783	Remote Similarity	NPD7625	Phase 1
0.6777	Remote Similarity	NPD7128	Approved
0.6777	Remote Similarity	NPD5739	Approved
0.6777	Remote Similarity	NPD6675	Approved
0.6777	Remote Similarity	NPD6402	Approved
0.6777	Remote Similarity	NPD6008	Approved
0.6767	Remote Similarity	NPD6033	Approved
0.6752	Remote Similarity	NPD6083	Phase 2
0.6752	Remote Similarity	NPD6084	Phase 2
0.6748	Remote Similarity	NPD6372	Approved
0.6748	Remote Similarity	NPD6373	Approved
0.6696	Remote Similarity	NPD7524	Approved
0.6695	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6928	Phase 2
0.6667	Remote Similarity	NPD6899	Approved
0.664	Remote Similarity	NPD8130	Phase 1
0.664	Remote Similarity	NPD6650	Approved
0.664	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD7640	Approved
0.6639	Remote Similarity	NPD7639	Approved
0.6604	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5697	Approved
0.6585	Remote Similarity	NPD5701	Approved
0.6579	Remote Similarity	NPD6051	Approved
0.6577	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7102	Approved
0.656	Remote Similarity	NPD6883	Approved
0.656	Remote Similarity	NPD7290	Approved
0.6549	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5956	Approved
0.6514	Remote Similarity	NPD7525	Registered
0.6512	Remote Similarity	NPD7115	Discovery
0.6509	Remote Similarity	NPD7339	Approved
0.6509	Remote Similarity	NPD6942	Approved
0.6508	Remote Similarity	NPD6869	Approved
0.6508	Remote Similarity	NPD6847	Approved
0.6508	Remote Similarity	NPD6617	Approved
0.6486	Remote Similarity	NPD6695	Phase 3
0.648	Remote Similarity	NPD6013	Approved
0.648	Remote Similarity	NPD6014	Approved
0.648	Remote Similarity	NPD6012	Approved
0.6466	Remote Similarity	NPD7604	Phase 2
0.6457	Remote Similarity	NPD6053	Discontinued
0.6441	Remote Similarity	NPD5695	Phase 3
0.6439	Remote Similarity	NPD5983	Phase 2
0.6429	Remote Similarity	NPD4786	Approved
0.6429	Remote Similarity	NPD4634	Approved
0.6417	Remote Similarity	NPD5696	Approved
0.6404	Remote Similarity	NPD7750	Discontinued
0.64	Remote Similarity	NPD6011	Approved
0.6378	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6336	Discontinued
0.6356	Remote Similarity	NPD7748	Approved
0.6348	Remote Similarity	NPD6903	Approved
0.6348	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7902	Approved
0.6333	Remote Similarity	NPD4755	Approved
0.6325	Remote Similarity	NPD7637	Suspended
0.6325	Remote Similarity	NPD8034	Phase 2
0.6325	Remote Similarity	NPD8035	Phase 2
0.6316	Remote Similarity	NPD7521	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6303	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6933	Approved
0.6293	Remote Similarity	NPD4753	Phase 2
0.6281	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD4225	Approved
0.6277	Remote Similarity	NPD8337	Approved
0.6277	Remote Similarity	NPD8336	Approved
0.6273	Remote Similarity	NPD7645	Phase 2
0.6271	Remote Similarity	NPD4202	Approved
0.6262	Remote Similarity	NPD4784	Approved
0.6262	Remote Similarity	NPD4785	Approved
0.625	Remote Similarity	NPD3667	Approved
0.623	Remote Similarity	NPD5285	Approved
0.623	Remote Similarity	NPD4696	Approved
0.623	Remote Similarity	NPD5286	Approved
0.623	Remote Similarity	NPD4700	Approved
0.6226	Remote Similarity	NPD4243	Approved
0.622	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6931	Approved
0.6216	Remote Similarity	NPD6930	Phase 2
0.6204	Remote Similarity	NPD8074	Phase 3
0.619	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7515	Phase 2
0.6183	Remote Similarity	NPD6274	Approved
0.6174	Remote Similarity	NPD6098	Approved
0.6165	Remote Similarity	NPD7101	Approved
0.6165	Remote Similarity	NPD7100	Approved
0.6154	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD6904	Approved
0.6154	Remote Similarity	NPD6080	Approved
0.614	Remote Similarity	NPD3665	Phase 1
0.614	Remote Similarity	NPD3666	Approved
0.614	Remote Similarity	NPD3133	Approved
0.6129	Remote Similarity	NPD7632	Discontinued
0.6129	Remote Similarity	NPD5211	Phase 2
0.6129	Remote Similarity	NPD4633	Approved
0.6129	Remote Similarity	NPD5226	Approved
0.6129	Remote Similarity	NPD5224	Approved
0.6129	Remote Similarity	NPD5225	Approved
0.6126	Remote Similarity	NPD4195	Approved
0.6126	Remote Similarity	NPD6929	Approved
0.6121	Remote Similarity	NPD4250	Approved
0.6121	Remote Similarity	NPD4251	Approved
0.6111	Remote Similarity	NPD4767	Approved
0.6111	Remote Similarity	NPD6926	Approved
0.6111	Remote Similarity	NPD6924	Approved
0.6111	Remote Similarity	NPD4768	Approved
0.6091	Remote Similarity	NPD6932	Approved
0.609	Remote Similarity	NPD6335	Approved
0.6087	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7900	Approved
0.608	Remote Similarity	NPD5174	Approved
0.608	Remote Similarity	NPD5175	Approved
0.6074	Remote Similarity	NPD6908	Approved
0.6074	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD6909	Approved
0.6071	Remote Similarity	NPD4748	Discontinued
0.6068	Remote Similarity	NPD6672	Approved
0.6068	Remote Similarity	NPD5737	Approved
0.605	Remote Similarity	NPD7087	Discontinued
0.605	Remote Similarity	NPD5281	Approved
0.605	Remote Similarity	NPD5284	Approved
0.6048	Remote Similarity	NPD5223	Approved
0.6048	Remote Similarity	NPD5344	Discontinued
0.6047	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD7799	Discontinued
0.6034	Remote Similarity	NPD4249	Approved
0.6033	Remote Similarity	NPD5210	Approved
0.6033	Remote Similarity	NPD4629	Approved
0.6033	Remote Similarity	NPD7991	Discontinued
0.6032	Remote Similarity	NPD5141	Approved
0.6017	Remote Similarity	NPD5328	Approved
0.6016	Remote Similarity	NPD4729	Approved
0.6016	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD4730	Approved
0.6015	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6683	Phase 2
0.597	Remote Similarity	NPD6313	Approved
0.597	Remote Similarity	NPD6314	Approved
0.5966	Remote Similarity	NPD7838	Discovery
0.5966	Remote Similarity	NPD6698	Approved
0.5966	Remote Similarity	NPD46	Approved
0.5966	Remote Similarity	NPD5207	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